US2006270845A1PendingUtilityA1
16-Hydroxyestratrienes as selectively active estrogens

Assignee: KUENZER HERMANNPriority: Feb 9, 1999Filed: Aug 3, 2006Published: Nov 30, 2006
Est. expiryFeb 9, 2019(expired)· nominal 20-yr term from priority
Inventors:Hermann Kuenzer Rudolf Knauthe Monika Lessl Karl-Heinrich Fritzemeier Christa Hegele-Hartung Ulf Boemer Gerd Mueller Dirk Kosemund
C07J 9/00C07J 1/00C07J 41/00A61K 31/565
PatentIndex Score
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References
Claims
Abstract

The invention describes new compounds as pharmaceutical active ingredients, which have in vitro a higher affinity to estrogen receptor preparations from rat prostates than to estrogen receptor preparations from rat uteri and in vivo a preferential action on bone rather than the uterus, their production, their therapeutic use and pharmaceutical dispensing forms that contain the new compounds. The new compounds are 16α- and 16β-hydroxy-estra-1,3,5(10)-estratrienes, which carry additional substituents on the steroid skeleton and can have one or more additional double bonds in the B-, C- and/or D-rings.
Claims

exact text as granted — not AI-modified
1 .- 52 . (canceled)  
     
     
         53 . A method for the treatment of an estrogen-deficiency-induced disease in a female or male patient which comprises administering an effective amount of 3,16-dihydroxyestra-1,3,5(10)-triene compound of formula I:  
       
         
           
           
               
               
           
         
       
       in which radicals R 1  to R 17 , independently of one another, have the following meanings: 
 R 1  means a halogen atom, a hydroxyl group, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group or a hydrogen atom;  
 R 2  means a halogen atom, a hydroxyl group, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with up to 6 carbon atoms or a hydrogen atoms;  
 R 4  means a halogen atom, a straight-chain or branched-chain, saturated or unsaturated alkyl group with 1 to 10 carbon atoms, a trifluoromethyl or pentafluoroethyl group, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with 1 to 6 carbon atoms or a hydrogen atom;  
 R 7  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with 1 to 6 carbon atoms, an optionally substituted aryl or heteroaryl radical or a hydrogen atom;  
 R 8  means a hydrogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position or a cyano group in α- or β-position;  
 R 9  means a hydrogen atom in α- or β-position, a methyl, ethyl, trifluoromethyl or pentafluoroethyl group in α- or β-position;  
 R 11  means a nitrooxy group in α- or β-position, a hydroxyl or mercapto group in α- or β-position, a halogen atom in α- or β-position, a chloromethyl group in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy or alkylthio group with 1 to 6 carbon atoms, an optionally substituted aryl or heteroaryl radical or a hydrogen atom;  
 R 13  means a methyl, ethyl, trifluoromethyl or pentafluoroethyl group in β-position;  
 and either  
 R 14  means a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position or a hydrogen atom in α- or β-position,  
 and  
 R 15  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position that can be interrupted by one or more oxygen atoms, sulfur atoms, sulfoxide or sulfone groups or imino groups=NR 15′  (R 15′ =hydrogen atom, methyl, ethyl, propyl, i-propyl) or a hydrogen atom,  
 or  
 R 14  and R 15  together mean a 14α,15α-methylene or 14β,15β-methylene group that is optionally substituted with one or two halogen atoms;  
 R 16  means a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a trifluoromethyl or pentafluoroethyl group, a cyanomethyl group or a hydrogen atom in α- or β-position; and  
 R 17  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a hydrogen atom or a hydroxyl group;  
 wherein one or both hydroxyl groups at C atoms 3 and 16 are optionally esterified with an aliphatic, straight-chain or branched-chain, saturated or unsaturated C 1 -C 14  mono- or polycarboxylic acid or an aromatic carboxylic acid or with an α- or β-amino acid;  
 wherein the   bonds in rings B, C and D optionally mean a single bond or optionally a double bond, and the wavy lines mean the arrangement of the respective substituent in α- or β-position; and  
 wherein the following compounds are excluded: estra-1,3,5(10)-triene-3,16α-diol, estra-1,3,5(10)-triene-3,16β-diol, estra-1,3,5(10),7-tetraene-3,16α-diol, estra-1,3,5(10),7-tetraene-3,16β-diol and estriol.  
 
     
     
         54 . The method of  claim 53 , wherein the disease is a peri- or post-menopausal symptom.  
     
     
         55 . The method of  claim 53 , wherein the disease is a peri- or post-male-menopausal symptom.  
     
     
         56 . The method of  claim 53 , wherein the disease is hot flashes, a sleep disturbance, irritability, mood swings, incontinence, vaginal atrophy, or a hormone-deficiency-induced emotional disease.  
     
     
         57 . The method of  claim 53 , wherein the disease is a disease in the urogenital tract.  
     
     
         58 . The method of  claim 53 , wherein the disease is a gastrointestinal disease.  
     
     
         59 . The method of  claim 53 , wherein the disease is an ulcer or hemorrhagic diatheses in the gastrointestinal tract.  
     
     
         60 . The method of  claim 53 , wherein the disease is a neoplasias.  
     
     
         61 . The method of  claim 53 , wherein the disease is a male infertility and the administration is in-vitro.  
     
     
         62 . The method of  claim 53 , wherein the disease is male infertility and the treatment is in-vivo.  
     
     
         63 . The method of  claim 53 , wherein the disease is female infertility and the treatment is in-vitro.  
     
     
         64 . The method of  claim 53 , wherein the disease is female infertility and the treatment is in-vivo.  
     
     
         65 . The method of  claim 53 , wherein the treatment is a hormone replacement therapy (HRT).  
     
     
         66 . The method of  claim 53 , wherein the disease is a hormone-deficiency-induced symptom due to surgery or medical treatment or from ovarian dysfunction.  
     
     
         67 . The method of  claim 53 , wherein the disease is hormone-deficiency-induced bone mass loss.  
     
     
         68 . The method of  claim 53 , wherein the disease is osteoporosis.  
     
     
         69 . The method of  claim 53 , wherein the disease is a cardiovascular disease.  
     
     
         70 . The method of  claim 53 , wherein the disease is a vascular disease.  
     
     
         71 . The method of  claim 53 , wherein the disease is arteriosclerosis.  
     
     
         72 . The method of  claim 53 , wherein the disease is neointimal hyperplasias.  
     
     
         73 . The method of  claim 53 , wherein the disease is a hormone-deficiency-induced neurodegenerative disease.  
     
     
         74 . The method of  claim 53 , wherein the disease is Alzheimer&#39;s disease or hormone-deficiency-induced impairment of memory and learning capacity.  
     
     
         75 . The method of  claim 53 , wherein the disease is an inflammatory disease or disease of the immune system.  
     
     
         76 . The method of  claim 53 , wherein the disease is benign prostate hyperplasia (BPH).  
     
     
         77 . The method of  claim 53 , wherein, in the compound of formula I, radicals R 1  to R 17 , independently of one another, have the following meanings 
 R 1  means a fluorine atom, a hydroxyl group, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group or a hydrogen atom;    R 2  means a fluorine atom, a hydroxyl group, a methoxy or ethoxy group or a hydrogen atom;    R 4  means a fluorine atom, a methyl, ethyl, trifluoromethyl, methoxy or ethoxy group or a hydrogen atom;    R 7  means a fluorine atom in α- or β-position, a methyl, ethyl, propyl or i-propyl group in α- or β-position, an optionally substituted aryl radical, a trifluoromethyl group in α- or β-position or a hydrogen atom;    R 8  means a hydrogen atom in α- or β-position, a methyl or ethyl group in α- or β-position;    R 9  means a hydrogen atom in α- or β-position, a methyl, ethyl, trifluoromethyl or pentafluoroethyl group in α- or β-position;    R 11  means a nitrooxy group in α- or β-position, a hydroxyl group in α- or β-position, a fluorine atom in α- or β-position, a choromethyl group in α- or β-position, a methyl group in α- or β-position, a methoxy group in α- or β-position, a phenyl- or 3-methylthien-2-yl radical in α- or β-position or a hydrogen atom;    R 13  means a methyl or ethyl group in β-position;    and either    R 14  means a hydrogen atom in α- or β-position or a methyl group in α- or β-position,    and    R 15  means a fluorine atom in α- or β-position, a methyl group in α- or β-position, or a hydrogen atom,    or    R 14  and R 15  together mean a 14α,15α-methylene group or a 14β,15β-methylene group;    R 16  means a methyl, ethyl, ethinyl, propinyl or trifluoromethyl group;    R 17  means a fluorine atom in α- or β-position, a methyl group, a hydrogen atom or a hydroxyl group,    and the   bonds in rings B, C and D are single bonds and the   bond between carbon atoms 9 and 11 means either a single or a double bond.    
     
     
         78 . The method of  claim 53 , wherein, in the compound of formula I: 
 R 7  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with 1 to 6 carbon atoms, or an optionally substituted aryl or heteroaryl radical    and    R 1 , R 2 , R 4 , R 8 , R 9 , R 11 , R 14 , R 15 , R 16  and R 17  in each case mean a hydrogen atom.    
     
     
         79 . The method of  claim 53 , wherein, in the compound of formula I: 
 R 11  means a nitrooxy group in α- or β-position, a hydroxyl or mercapto group in α- or β-position, a halogen atom in α- or β-position, a chloromethyl group in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy or alkylthio group with up to 6 carbon atoms, or an optionally substituted aryl or heteroaryl radical, and    R 1 , R 2 , R 4 , R 7 , R 8 , R 9 , R 14 , R 15 , R 16  and R 17  in each case mean a hydrogen atom.    
     
     
         80 . The method of  claim 53 , wherein, in the compound of formula I: 
 R 15  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position that can be interrupted by one or more oxygen atoms, sulfur atoms, sulfoxide or sulfone groups or imino groups=NR 15′  (R 15′ =hydrogen atom, methyl, ethyl, propyl, i-propyl), and    R 1 , R 2 , R 4 , R 7 , R 8 , R 9 , R 11 , R 14 , R 16  and R 17  in each case mean a hydrogen atom.    
     
     
         81 . The method of  claim 53 , wherein, in the compound of formula I: 
 R 7  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with 1 to 6 carbon atoms or an optionally substituted aryl or heteroaryl radical,    R 11  means a nitrooxy group in α- or β-position, a hydroxyl or mercapto group in α- or β-position, a halogen atom in α- or β-position, a chloromethyl group in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy or alkylthio group with 1 to 6 carbon atoms or an optionally substituted aryl or heteroaryl radical, and    R 1 , R 2 , R 4 , R 8 , R 9 , R 14 , R 15 , R 16  and R 17  in each case mean a hydrogen atom.    
     
     
         82 . The method of  claim 53 , wherein, in the compound of formula I; 
 R 7  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with 1 to 6 carbon atoms or an optionally substituted aryl or heteroaryl radical,    R 15  means a halogen atom in α- or β-position or a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position that can be interrupted by one or more oxygen atoms, sulfur atoms, sulfoxide or sulfone groups or imino groups=NR 15′  (R 15′ =hydrogen atom, methyl, ethyl, propyl, i-propyl), and    R 1 , R 2 , R 4 , R 8 , R 9 , R 11 , R 14 , R 16  and R 17  in each case mean a hydrogen atom.    
     
     
         83 . The method of  claim 53 , wherein, in the compound of formula I: 
 R 11  means a nitrooxy group in Ca- or β-position, a hydroxy or mercapto group in α- or β-position, a halogen atom in α- or β-position, a chloromethyl group in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy or alkylthio group with 1 to 6 carbon atoms or an optionally substituted aryl or heteroaryl radical,    R 15  means a halogen atom in α- or β-position or a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position that can be interrupted by one or more oxygen atoms, sulfur atoms, sulfoxide or sulfone groups or imino groups=NR 15′  (R 15′ =hydrogen atom, methyl, ethyl, propyl, i-propyl), and    R 1 , R 2 , R 4 , R 7 , R 8 , R 9 , R 14 , R 16 , and R 17  in each case mean a hydrogen atom.    
     
     
         84 . The method of  claim 53 , wherein, in the compound of formula I: 
 R 7  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with 1 to 6 carbon atoms or an optionally substituted aryl or heteroaryl radical,    R 11  means a nitrooxy group in α- or β-position, a hydroxyl or mercapto group in α- or β-position, a halogen atom in α- or β-position, a chloromethyl group in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy or alkylthio group with 1 to 6 carbon atoms or an optionally substituted aryl or heteroaryl radical,    R 15  means a halogen atom in α- or β-position, or a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position that can be interrupted by one or more oxygen atoms, sulfur atoms, sulfoxide or sulfone groups or imino groups=NR 15′  (R 15′ =hydrogen atom, methyl, ethyl, propyl, i-propyl), and    R 1 , R 2 , R 4 , R 8 , R 9 , R 14 , R 16  and R 17  in each case mean a hydrogen atom.    
     
     
         84 . The method of  claim 53 , wherein, in the compound of formula I, one or both hydroxyl groups is (are) esterified at C atoms 3 and 16 with an aliphatic or aromatic carboxylic acid or with an α- or β-amino acid.  
     
     
         85 . The method of  claim 53 , wherein the compound of formula I is selected from: 
 14α,15α-Methylen-estra-1,3,5(10)-triene-3,16α-diol,    14β,15β-Methylen-estra-1,3,5(10)-triene-3,16α-diol,    14β,15β-Methylen-estra-1,3,5(10),8(9)-tetraene-3,16α-diol,    Estra-1,3,5(10),8(9)-tetraene-3,16α-diol,    Estra-1,3,5(10),8(14)-tetraene-3,16α-diol,    Estra-1,3,5(10),6,8-pentaene-3,16α-diol,    7α-Fluoro-estra-1,3,5(10)-triene-3,16α-diol,    11β-Methoxy-estra-1,3,5(10)-triene-3,16α-diol,    7α-Methyl-estra-1,3,5(10)-triene-3,16α-diol    11β-Fluoro-estra-1,3,5(10)-triene-3,16α-diol,    8a-Estra-1,3,5(10)-triene-3,16α-diol    Estra-1,3,5(10)-triene-2,3,16α-triol    17β-Fluoro-estra-1,3,5(10)-triene-3,16α-diol,    18a-Homo-estra-1,3,5(10)-triene-3,16α-diol,    18a-Homo-estra-1,3,5(10),8(9)-tetraene-3,16α-diol,    18a-Homo-14α,15α-methylen-estra-1,3,5(10)triene-3,16α-diol,    18a-Homo-14α,15α-methylen-estra-1,3,5(10),8(9)-tetraene-3,16α-diol,    18a-Homo-14α,15α-methylen-estra-1,3,5(10),6,8-pentaene-3,16α-diol.    14α,15α-Methylen-estra-1,3,5(10)-triene-3,16β-diol    14β,15β-Methylen-estra-1,3,5(10)-triene-3,16β-diol    14β,15β-Methylen-estra-1,3,5(10),8(9)-tetraene-3,16β-diol,    Estra-1,3,5(10),8(9)-tetraene-3,16β-diol,    Estra-1,3,5(10),8(14)-tetraene-3,16β-diol,    Estra-1,3,5(10),6,8-pentaene-3,16β-diol,    7α-Fluoro-estra-1,3,5(10)-triene-3,16β-diol,    11β-Methoxy-estra-1,3,5(10)-triene-3,16β-diol,    7α-Methyl-estra-1,3,5(10)-triene-3,16β-diol    11β-Fluoro-estra-1,3,5(10)-triene-3,16β-diol,    8α-Estra-1,3,5(10)-triene-3,16β-diol    Estra-1,3,5(10)-triene-2,3,16α-triol    17β-Fluoro-estra-1,3,5(10)-triene-3,16β-diol,    18a-Homo-estra-1,3,5(10)-triene-3,16β-diol,    18a-Homoestra-1,3,5(10),8(9)-tetraene-3,16β-diol,    18a-Homo-14α,15αa-methylen-estra-1,3,5(10)-triene-3,16β-diol,    18a-Homo-14α,15α-methylen-estra-1,3,5(10),8(9)-tetraene-3,16β-diol,    18a-Homo-14α,15α-methylen-estra-1,3,5(10),6,8-pentaene-3,16β-diol,    7α-Ethyl-estra-1,3,5(10)-triene-3,16α-diol,    7α-Propyl-estra-1,3,5(10)-triene-3,16α-diol,    7α-i-Propyl-estra-1,3,5(10)-triene-3,16α-diol,    7α-i-Propenyl-estra-1,3,5(10)-triene-3,16α-diol,    7α-Phenyl-estra-1,3,5(10)-triene-3,16α-diol,    7α-Methoxy-estra-1,3,5(10)-triene-3,16α-diol,    7α-Thiomethyl-estra-1,3,5(10)-triene-3,16α-diol,    7α-Cyanomethyl-estra-1,3,5(10)-triene-3,16α-diol,    7β-Ethyl-estra-1,3,5(10)-triene-3,16α-diol,    70β-Propyl-estra-1,3,5(10)-triene-3,16α-diol,    70β-i-Propyl-estra-1,3,5(10)-triene-3,16α-diol,      7 β-i-Propenyl-estra-1,3,5(10)-triene-3,16α-diol,    7β-Phenyl-estra-1,3,5(10)-triene-3,16α-diol,    7β-Methoxy-estra-1,3,5(10)-triene-3,16α-diol,    70β-Thiomethyl-estra-1,3,5(10)-triene-3,16α-diol,    7β-Cyanomethyl-estra-1,3,5(10)-triene-3,16α-diol,    7α-Ethyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-Propyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-i-Propyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-i-Propenyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-Phenyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-Methoxy-estra-1,3,5(10)-triene-3,16β-diol,    7α-Thiomethyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-Cyanomethyl-estra-1,3,5(10)-triene-3,16β-diol,    70β-Ethyl-estra-1,3,5(10)-triene-3,16,β-diol,    7β-Propyl-estra-1,3,5(10)-triene-3,16β-diol,    70β-Propyl-estra-1,3,5(10)-triene-3,16β-diol,    7β-i-Propenyl-estra-1,3,5(10)-triene-3,16β-diol,    70β-Phenyl-estra-1,3,5(10)-triene-3,16β-diol,    7β-Methoxy-estra-1,3,5(10)-triene-3,16β-diol,    7β-Thiomethyl-estra-1,3,5(10)-triene-3,16β-diol,    7β-Cyanomethyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Methyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Ethyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Propyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Allyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-i-Propyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-i-Propenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Methoxy-estra-1,3,5(10)-triene-3,16α-diol,    15α-Thiomethyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Methyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Ethyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Propyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Allyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-i-Propyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-i-Propenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Methoxy-estra-1,3,5(10)-triene-3,16β-diol,    15α-Thiomethyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Methyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Ethyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Propyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Allyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-i-Propyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-i-Propenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Methoxy-estra-1,3,5(10)-triene-3,16α-diol,    15β-Thiomethyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Methyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Ethyl-estra-1,3,5(10)triene-3,16β-di    15β-Propyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Allyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-i-Propyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-i-Propenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Methoxy-estra-1,3,5(10)triene-3,16β-diol,    15β-Thiomethyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-Trifluoromethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-Pentafluoroethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-Ethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-i-Propyl-11-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-i-Propenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-Phenyl-11β-Fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-Methoxy-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-Thiomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,      7 α-Cyanomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7β-Ethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7β-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7β-i-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7β-i-Propenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7β-Phenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7β-Methoxy-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7β-Thiomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7β-Cyanomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-Ethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7α-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7α-i-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7α-i-Propenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7α-Phenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7α-Methoxy-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7α-Thiomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7α-Cyanomethyl-11β-fluoroestra-1,3,5(10)-triene-3,16β-diol,    7β-Ethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7β-Propyl-11β-fluoro-estra-1,3,5(10)triene-3,16β-diol,    7β-i-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7β-i-Propenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7β-Phenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7β-Methoxy-11β-fluoro-estra-1,3,5(10)triene-3,16β-diol,    7β-Thiomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    7β-Cyanomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15α-Methyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-Ethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-Allyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-i-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-i-Propenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-Methoxy-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-Thiomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-Methyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15α-Ethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15α-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15α-Allyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15α-i-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-i-Propenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-Methoxy-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15α-Thiomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15β-Methyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15β-Ethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15β-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15β-Allyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15β-i-Propyl-11β-fluoro-estra-1,3,5(10)triene-3,16α-diol,    15β-i-Propenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15β-Methoxy-11β-fluoro-estra-1,3,5(10)triene-3,16α-diol,    15β-Thiomethyl-11β-fluoro-estra-1,3,5(10)-triene-3,16α-diol,    15β-Methyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15β-Ethyl-11-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15β-Propyl-11β-fluoro-estra-1,3,5(10)triene-3,16β-diol,    15β-Allyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15β-i-Propyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15β-i-Propenyl-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15β-Methoxy-11β-fluoro-estra-1,3,5(10)-triene-3,16β-diol,    15β-Thiomethyl-11β-fluoro-estra-1,3,5(10)triene-3,16β-diol,    14α,15α-Methylene-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    14β,15β-Methylene-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    14β,15β-Methylene-7α-phenyl-estra-1,3,5(10),8(9)-tetraene-3,16α-diol,    7α-phenyl-estra-1,3,5(10),8(9)-tetraene-3,16α-diol,    7α-Phenyl-estra-1,3,5(10),8(14)-tetraene-3,16α-diol,    7α-Phenyl-estra-1,3,5(10),6,8-pentaene-3,16α-diol,    11β-Methoxy-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    11β-Fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    7α-Phenyl-8α-estra-1,3,5(10)-triene-3,16α-diol,    7α-Phenyl-estra-1,3,5(10)-triene-2,3,16α-triol,    17β-Fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    18a-Homo-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    18a-Homo-7α-phenyl-estra-1,3,5(10),8(9)-tetraene-3,16α-diol,    18a-Homo-14α,15α-methylene-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    18a-Homo-14α,15α-methylene-7α-phenyl-estra-1,3,5(10),8(9)-tetraene-3,16α-diol,    18a-Homo-14α,15α-methylene-7α-phenyl-estra-1,3,5(10),6,8-pentaene-3,16α-diol,    14α,15α-Methylene-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    14β,15β-Methylene-7α-phenyl-estra-1,3,5(10)triene-3,16β-diol,    14β,15β-Methylene-7α-phenyl-estra-1,3,5(10),8(9)-tetraene-3,16β-diol,    7α-Phenyl-estra-1,3,5(10),8(9)-tetraene-3,16β-diol,    7α-Phenyl-estra-1,3,5(10),8(14)-tetraene-3,16β-diol,    7α-Phenyl-estra-1,3,5(10),6,8-pentaene-3,16β-diol,    11β-Methoxy-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    11β-Fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-Phenyl-8α-estra-1,3,5(10)-triene-3,16β-diol,    7α-Phenyl-estra-1,3,5(10)-triene-2,3,16α-triol,    17β-Fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    18a-Homo-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    18a-Homo-7α-phenyl-estra-1,3,5(10),8(9)-tetraene-3,16β-diol,    18a-Homo-14α,15α-methylene-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    18a-Homo-14α,15α-methylene-7α-phenyl-estra-1,3,5(10),8(9)-tetraene-3,16β-diol,    18a-Homo-14α,15α-methylene-7α-phenyl-estra-1,3,5(10),6,8-pentaene-3,16β-diol,    15α-Methyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Ethyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Propyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Allyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-i-Propyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-i-Propenyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Methoxy-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Thiomethyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Methyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Ethyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Propyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Allyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-i-Propyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-i-Propenyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Methoxy-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Thiomethyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Methyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Ethyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Propyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol    15β-Allyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-i-Propyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-i-Propenyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Methoxy-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Thiomethyl-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Methyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Ethyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Propyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Allyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-i-Propyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-i-Propenyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Methoxy-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Thiomethyl-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Methyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Ethyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Propyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Allyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-i-Propyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)triene-3,16α-diol,    15α-i-Propenyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)triene-3,16α-diol,    15α-Methoxy-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Thiomethyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15α-Methyl-11-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Ethyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Propyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Allyl-11β-fluoro7α-phenyl-estra-1,3,5(10)-triene-3,16β,-diol,    15α-i-Propyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-i-Propenyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Methoxy-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15α-Thiomethyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Methyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Ethyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Propyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Allyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-i-Propyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-i-Propenyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Methoxy-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Thiomethyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16α-diol,    15β-Methyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)triene-3,16β-diol,    15β-Ethyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Propyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Allyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-i-Propyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-i-Propenyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Methoxy-11β-fluoro-7α-phenyl-estra-1,3,5(10)-triene-3,16β-diol,    15β-Thiomethyl-11β-fluoro-7α-phenyl-estra-1,3,5(10)triene-3,16β-diol,    11β-[2-(3-Methylthien)-yl)estra-1,3,5(10)-triene-3,16α-diol,    11β-[2-(3-Methylthien)-yl)-estra-1,3,5(10)-triene-3,16β-diol.    11β-methylestra-1,3,5(10)-triene-3,16α-diol,    11β-methylestra-1,3,5(10)-triene-3,16β-diol,    11β-methyl-18a-homoestra-1,3,5(10)-triene-3,16α-diol,    11β-methyl-18a-homoestra-1,3,5(10)-triene-3,16β-diol,    11β-ethylestra-1,3,5(10)-triene-3,16α-diol,    11β-ethylestra-1,3,5(10)-triene-3,16β-diol,    11β-ethyl-18a-homoestra-1,3,5(10)-triene-3,16α-diol,    11β-ethyl-18a-homoestra-1,3,5(10)-triene-3,16β-diol,    9α-methylestra-1,3,5(10)-triene-3,16α-diol, or    9α-methyl-18a-homoestra-1,3,5(10)triene-3,16α-diol.    
     
     
         86 . The method of  claim 53 , wherein the compound of formula I is selected from: 
 7α-Fluoro-estra-1,3,5(10)-triene-3,16α-diol,    7α-Methyl-estra-1,3,5(10)-triene-3,16β-diol,    7α-Methyl-estra-1,3,5(10-triene-3,16α-diol, or    18α-Homo-estra-1,3,5(10)-triene-3,16α-diol.    
     
     
         87  . The method of  claim 53 , wherein the compound f formula I has a dissociation in favor of its estrogenic action on bone rather than on the uterus.  
     
     
         88 . A 3,16-dihydroxyestra-1,3,5(10)-triene compound of formula I:  
       
         
           
           
               
               
           
         
       
       in which radicals R 1  to R 17 , independently of one another, have the following meanings: 
 R 1  means a halogen atom, a hydroxyl group, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group or a hydrogen atom;  
 R 2  means a halogen atom, a hydroxyl group, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with up to 6 carbon atoms or a hydrogen atom;  
 R 4  means a halogen atom, a straight-chain or branched-chain, saturated or unsaturated alkyl group with 1 to 10 carbon atoms, a trifluoromethyl or pentafluoroethyl group, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with 1 to 6 carbon atoms or a hydrogen atom;  
 R 7  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy group with 1 to 6 carbon atoms, an optionally substituted aryl or heteroaryl radical or a hydrogen atom;  
 R 8  means a hydrogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position or a cyano group in α- or β-position;  
 R 9  means a hydrogen atom in α- or β-position, a methyl, ethyl, trifluoromethyl or pentafluoroethyl group in αor β-position;  
 R 11  means a nitrooxy group in α- or β-position, a hydroxyl or mercapto group in α- or β-position, a halogen atom in α- or β-position, a chloromethyl group in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated alkoxy or alkylthio group with 1 to 6 carbon atoms, an optionally substituted aryl or heteroaryl radical or a hydrogen atom;  
 R 13  means a methyl, ethyl, trifluoromethyl or pentafluoroethyl group in β-position;  
 and either  
 R 14  means a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position or a hydrogen atom in α- or β-position,  
 and  
 R 15  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position that can be interrupted by one or more oxygen atoms, sulfur atoms, sulfoxide or sulfone groups or imino groups=NR 15′  (R 15′ =hydrogen atom, methyl, ethyl, propyl, i-propyl) or a hydrogen atom, or  
 R 14  and R 15  together mean a 14α,15α-methylene or 14β,15β-methylene group that is optionally substituted with one or two halogen atoms;  
 R 16  means a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a trifluoromethyl or pentafluoroethyl group, a cyanomethyl group or a hydrogen atom in α- or β-position;  
 R 17  means a halogen atom in α- or β-position, a straight-chain or branched-chain, saturated or unsaturated, optionally partially or completely fluorinated alkyl group with 1 to 10 carbon atoms in α- or β-position, a hydrogen atom or a hydroxyl group;  
 wherein one or both hydroxyl groups at C atoms 3 and 16 are optionally esterified with an aliphatic, straight-chain or branched-chain, saturated or unsaturated C 1 -C 14  mono- or polycarboxylic acid or an aromatic carboxylic acid or with an α- or β-amino acid;  
 wherein the   bonds in rings B, C and D mean a single bond or optionally a double bond, provided that at least one of the   bonds is a double bond, and the wavy lines mean the arrangement of the respective substituent in α- or β-position; and  
 wherein the following compounds are excluded: estra-1,3,5(10),7-tetraene-3,16α-diol, and estra-1,3,5(10),7-tetraene-3,16β-diol.  
 
     
     
         89 . A compound according to  claim 88 , wherein there is a double bond between C atoms 6 and 7.  
     
     
         90 . A compound according to  claim 88 , wherein there is a double bond between C atoms 7 and 8.  
     
     
         91 . A compound according to  claim 88 , wherein there is a double bond between C atoms 8 and 9.  
     
     
         92 . A compound according to  claim 88 , wherein there is a double bond between C atoms 9 and 11.  
     
     
         93 . A compound according to  claim 88 , wherein there is a double bond between C atoms 8 and 14.  
     
     
         94 . A compound according to  claim 88 , wherein there is a double bond between C atoms 11 and 12.  
     
     
         95 . A compound according to  claim 88 , wherein there is a double bond between C atoms 14 and 15.  
     
     
         96 . A compound according to  claim 88 , wherein there are double bonds between C atoms 6 and 7 and C atoms 8 and 9.  
     
     
         98 . A compound according to  claim 88 , wherein there are double bonds between C atoms 8 and 9 and C atoms 14 and 15.  
     
     
         99 . A compound according to  claim 88 , wherein there are double bonds between C atoms 6 and 7, C atoms 8 and 9 and C atoms 11 and 12.  
     
     
         100 . A compound according to  claim 88 , wherein there are double bonds between C atoms 6 and 7, C atoms 8 and 9 and C atoms 14 and 15.  
     
     
         101 . A compound according to  claim 88 , wherein there are double bonds between C atoms 6 and 7, C atoms 8 and 9, C atoms 11 and 12 and C atoms 14 and 15.
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