US2012269902A1PendingUtilityA1
Thiazole Compounds, and Compositions and Methods Using Same
Est. expiryJun 13, 2028(~1.9 yrs left)· nominal 20-yr term from priority
Inventors:Bassam Damaj
A61P 35/04A61P 35/00A61P 35/02A61K 31/282A61K 45/06A61K 31/428A61P 1/00A61K 31/505A61K 33/243
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Claims
Abstract
The present invention provides, in part, compounds and compositions including a thiazole moiety, that may be useful, for example, for treating cancers, for example kidney cancer.
Claims
exact text as granted — not AI-modified1 . A composition suitable for administering to a patient, comprising:
a) a compound represented by
wherein R 1 is selected from the group consisting of: -alkylene-R 5 -R 6 -R 2 , —R 6 —C(O)-phenyl, —R 6 -phenyl, alkyl, alkenyl or alkynyl, wherein the phenyl, independently for each occurrence, is optionally substituted by one or two moieties selected from the group consisting of halo, alkyl, CN, or NO 2 ;
R 2 is a heteroaryl optionally substituted by at one, two or three positions by halo, CN or alkyl;
R 3 , independently for each occurrence, is selected from the group consisting of H, halo, CN, and NO 2 ;
R 4 is selected from the group consisting of thio, sulfonyl, or sulfinyl;
R 5 is selected from the group consisting of thio, sulfonyl, or sulfinyl; and
R 6 is alkylene or a bond;
or pharmaceutically acceptable salts thereof; and
b) a pharmaceutically acceptable excipient.
2 . The composition of claim 1 , wherein the R 2 is a bicyclic or monocyclic heteroaryl.
3 . The composition of claim 1 or 2 , wherein R 2 is selected from the group consisting of benzothiazole, benzooxazole, isoquinoline, and pyridine.
4 . The composition of claim 1 wherein at least one R 3 is NO 2 and R 1 is alkyl or -alkylene-phenyl.
5 . The composition of claim 4 , wherein R 1 is methylbenzene, optionally substituted at one position by halo.
6 . The composition of claim 4 , wherein R 1 is ethyl or methyl.
7 . The composition of any one of claims 1 - 5 , wherein at least one R 3 is H.
8 . The composition of claim 2 or 3 , wherein R 6 is a bond.
9 . The composition of claim 2 , 3 or 8 , wherein R 5 is S.
10 . The composition of claim 2 , 3 , 8 or 9 , wherein R 4 is sulfonyl.
11 . The composition of any one of claims 1 - 9 , further comprising a chemotherapeutic agent.
12 . The composition of claim 10 , wherein the chemotherapeutic agent is selected from the group consisting of cisplatin, 5-fluorouracil, and vinblastine.
13 . A composition comprising:
a) a compound represented by:
wherein R 3 is chosen from H or NO 2 ;
and R 1 is chosen from: t-butyl, ethyl, methyl
; or pharmaceutically acceptable salts thereof; and
and
b) a pharmaceutically acceptable excipient.
14 . An article of manufacture comprising packaging material and a pharmaceutical composition contained within the packaging material, wherein the packaging material comprises a label which indicates that the pharmaceutical composition can be used for treatment of cancer and/or gastrointestinal symptoms, alone or in conjunction with administration of chemotherapeutics, and wherein the pharmaceutical composition comprises at least one compound of formula I:
wherein R 1 is selected from the group consisting of: -alkylene-R 5 -R 6 -R 2 , —R 6 —C(O)-phenyl, —R 6 -phenyl, alkyl, alkenyl or alkynyl, wherein the phenyl, independently for each occurrence, is optionally substituted by one or two moieties selected from the group consisting of halo, alkyl, CN, or NO 2 ;
R 2 is a heteroaryl optionally substituted by at one, two or three positions by halo, CN or alkyl;
R 3 , independently for each occurrence, is selected from the group consisting of H, halo, CN, and NO 2 ;
R 4 is selected from the group consisting of thio, sulfonyl, or sulfinyl;
R 5 is selected from the group consisting of thio, sulfonyl, or sulfinyl; and
R 6 is alkylene or a bond;
or pharmaceutically acceptable salts thereof.
15 . A method of treating cancer in a patient in need thereof, comprising administering an effective amount of at least one compound represented by formula II:
wherein
X is selected from the group of O, NR′ and S; wherein R′ is H or alkyl;
R 1 is selected from the group consisting of: -alkylene-R 5 -R 6 -R 12 , —R 6 —C(O)—R 12 , —R 6 -R 12 , alkyl, alkenyl, or alkynyl;
R 4 is selected from the group consisting of thio, sulfonyl, or sulfinyl;
R 5 is selected from the group consisting of thio, sulfonyl, or sulfinyl;
R 6 is alkylene or a bond;
R 12 is an aryl or heteroaryl optionally substituted by at one, two or three positions by halo, hydroxyl, mercapto, nitro, formyl, formamido, carboxy, cyano, amino, amido, carbamoyl, sulphamoyl, ureido, alkyl, alkenyl, alkynyl, alkoxy, alkanoyl, or alkoxycarbonyl, and
R 3 , independently for each occurrence, is selected from the group consisting of H, halo, cyano, hydroxyl, carboxy, alkyl, alkoxy, and nitro;
or pharmaceutically acceptable salts thereof.
16 . The method of claim 15 , further comprising administering another chemotherapeutic agent.
17 . The method of claim 16 wherein the chemotherapeutic agent and a compound of formula II are administered together in the same dosage form.
18 . The method of claim 16 wherein the chemotherapeutic agent and a compound of formula II are administered together in the separate dosage forms.
19 . The method of anyone of claims 16 - 18 , wherein the chemotherapeutic agent is selected from the group consisting of cisplatin, 5-fluorouracil, and vinblastine.
20 . The method of claim 15 , wherein R 12 is a heteroaryl optionally substituted by at one, two or three positions by halo, CN or alkyl.
21 . The method of claim 15 , wherein R 12 is a bicyclic or monocyclic heteroaryl.
22 . The method of claim 21 , wherein R 12 is selected from the group consisting of benzothiazole, benzooxazole, isoquinoline, and pyridine.
23 . The method of claim 15 , wherein at least one R 3 is NO 2 and R 1 is alkyl or -alkylene-phenyl.
24 . The method of claim 15 , wherein R 1 is methylbenzene, optionally substituted at one position by halo.
25 . The method of claim 15 , wherein R 1 is ethyl or methyl.
26 . The method of any one of claims 15 - 25 , wherein at least one R 3 is H.
27 . The method of claim 16 or 17 , wherein R 6 is a bond.
28 . The method of claim 16 or 17 , wherein R 5 is S.
29 . The method of claim 16 or 17 , wherein R 4 is sulfonyl.
30 . The method of any one of claims 15 - 29 , wherein X is S.
31 . The method of any one of claims 15 - 30 , wherein the cancer is selected from group consisting of kidney cancer, ovarian cancer, leukemia, lung cancer, bladder cancer, breast cancer, liver cancer, or thyroid cancer.
31 . A method of improving therapeutic efficacy of a chemotherapeutic agent, comprising administering to a patient in need thereof a compound represented by formula II:
wherein R 3 , R 4 , and R 1 are defined in claim 15 .
32 . A method of inhibiting tumor growth comprising administering to a patient in need thereof a compound represented by formula II:
wherein R 3 , R 4 , and R 1 are defined in claim 15 .Join the waitlist — get patent alerts
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