US2004214823A1PendingUtilityA1
Method of treating sexual disturbances
Est. expiryJan 6, 2019(expired)· nominal 20-yr term from priority
A61P 9/08A61P 15/10A61P 15/00A61P 21/02A61K 31/485A61K 31/47A61K 31/4745A61K 31/535A61K 31/52A61K 38/2278A61K 31/475A61K 31/557
60
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Claims
Abstract
The present invention is a method of treating sexual disturbances in humans and inducing mating in non-human mammals using the compounds of formula (A) in a dosage range where the sexually therapeutic amount is from about 0.2 thru 8 mg/person/dose and where the sexually mating amount is from about 0.003 thru 0.2 mg/kg/dose.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A method of treating sexual disturbances in a human who is in need of such treatment which comprises administering a sexually therapeutically effective amount of a compound of the formula (A)
where
R 1 , R 2 and R 3 are the same or different and are:
—H,
C 1 -C 6 alkyl,
C 3 -C 5 alkenyl,
C 3 -C 5 alkynyl,
C 3 -C 5 cycloalkyl,
C 4 -C 10 cycloalkyl,
phenyl substituted C 1 -C 6 alkyl,
—NR 1 R 2 where R 1 and R 2 are cyclized with the attached nitrogen atom to produce pyrrolidiyl, piperidinyl, morphoninyl, 4-methyl piperazinyl or imidazolyl;
X is:
—H,
C 1 -C 6 alkyl,
—F, —Cl, —Br, —I,
—OH,
C 1 -C 6 alkoxy,
cyano,
carboxamide,
carboxyl,
(C 1 -C 6 alkoxy)carbonyl,
A is:
CH,
CH 2 ,
CH-(halogen) where halogen is —F, —Cl, —Br, —I,
CHCH 3 ,
C═O,
C═S,
C—SCH 3 ,
C═NH,
C—NH 2 ,
C—NHCH 3 ,
C—NHCOOCH 3 ,
C—NHCN,
SO 2 ,
N;
B is:
CH 2 ,
CH,
CH-(halogen) where halogen is as defined above,
C═O,
N,
NH,
N—CH 3 ,
D is:
CH,
CH 2 ,
CH-(halogen) where halogen is as defined above,
C═O,
O,
N,
NH,
N—CH 3 :
and n is 0 or 1, and where is a single or double bond, with the provisos:
(1) that when n is 0, and
A is CH 2 , CH-(halogen) where halogen is as defined above, CHCH 3 , C═O, C═S, C═NH, SO 2 ,
then D is CH 2 , CH-(halogen) where hallogen is as defined above, C═O, O, NH, N—CH 3 ;
(2) that when n is 0, and
A is CH, C—SCH 3 , C—NH 2 , C—NHCH 3 , C—NHCOOCH 3 , C—NHCN, N; then
D is CH, N;
(3) that when n is 1, and
A is CH 2 , CH-(halogen) where halogen is as defined above, CHCH 3 , C═O, C═S, C═NH, SO 2 ; and
B is CH 2 , CH-(halogen) where halogen is as defined above, C═O, NH, N—CH 3 ; then
D is CH 2 , C═O, O, NH, N—CH 3 ;
(4) that when n is 1, and
A is CH, C—SCH 3 , C—NH 2 , C—NHCH 3 , C—NHCOOCH 3 , C—NHCN, N; and
B is CH, N; then
D is CH 2 , C═O, O, NH, N—CH 3 ;
(5) that when n is 1, and
A is CH 2 , CHCH 3 , C═O, C═S, C═NH, SO 2 , and
B is CH, N; then
D is CH, N; and pharmaceutically acceptable salts thereof to the human.
2 . A method of treating sexual disturbances according to claim 1 where the compound of formula (A) is (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione.
3 . A method of inducing mating a non-human mammal which comprises administering a sexually mating amount of a compound of the formula (A)
where
R 1 , R 2 and R 3 are the same or different and are:
—H,
C 1 -C 6 alkyl,
C 3 -C 5 alkenyl,
C 3 -C 5 alkynyl,
C 3 -C 5 cycloalkyl,
C 4 -C 10 cycloalkyl,
phenyl substituted C 1 -C 6 alkyl,
—NR 1 R 2 where R 1 and R 2 are cyclized with the attached nitrogen atom to produce pyrrolidiyl, piperidinyl, morphoninyl, 4-methyl piperazinyl or imidazolyl;
X is:
—H,
C 1 -C 6 alkyl,
—F, —Cl, —Br, —I,
—OH,
C 1 -C 6 alkoxy,
cyano,
carboxamide,
carboxyl,
(C 1 -C 6 alkoxy)carbonyl,
A is:
CH,
CH 2 ,
CH-(halogen) where halogen is —F, —Cl, —Br, —I,
CHCH 3 ,
C═O,
C═S,
C—SCH 3 ,
C═NH,
C—NH 2 ,
C—NHCH 3 ,
C—NHCOOCH 3 ,
C—NHCN,
SO 2 ,
N;
B is:
CH 2 ,
CH,
CH-(halogen) where halogen is as defined above,
C═O,
N,
NH,
N—CH 3 ,
D is:
CH,
CH 2 ,
CH-(halogen) where halogen is as defined above,
C═O,
O,
N,
NH,
N—CH 3 ;
and n is 0 or 1, and where is a single or double bond, with the provisos:
(1) that when n is 0, and
A is CH 2 , CH-(halogen) where halogen is as defined above, CHCH 3 , C═O, C═S, C═NH, SO 2 ;
then D is CH 2 , CH-(halogen) where halogen is as defined above, C═O, O, NH, N—CH 3 ;
(2) that when n is 0, and
A is CH, C—SCH 3 , C—NH 2 , C—NHCH 3 , C—NHCOOCH 3 , C—NHCN, N; then
D is CH, N;
(3) that when n is 1, and
A is CH 2 , CH-(halogen) where halogen is as defined above, CHCH 3 , C═O, C═S, C═NH, SO 2 ; and
B is CH 2 , CH-(halogen) where halogen is as defined above, C═O, NH, N—CH 3 ; then
D is CH 2 , C═O, O, NH, N—CH 3 ,
(4) that when n is 1, and
A is CH, C—SCH 3 , C—NH 2 , C—NHCH 3 , C—NHCOOCH 3 , C—NHCN, N; and
B is CH, N; then
D is CH 2 , C═O, O, NH, N—CH 3 ;
(5) that when n is 1, and
A is CH 2 , CHCH 3 , C═O, C═S, C═NH, SO 2 , and
B is CH, N; then
D is CH, N; and pharmaceutically acceptable salts thereof.
4 . A method of inducing mating according to claim 3 where the compound of formula (A) is (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione.
5 . A method of treating a sexual deficiency state in a human who has epilepsy, craniopharyngioma, hypogonadism or who has had a hysterectomyoophorectomy, hysterectomy or oophorectomy which comprises administering a sexually therapeutically effective amount of a compound of the formula (A)
where
R 1 , R 2 and R 3 are the same or different and are:
—H,
C 1 -C 6 alkyl,
C 3 -C 5 alkenyl,
C 3 -C 5 alkynyl,
C 3 -C 5 cycloalkyl,
C 4 -C 10 cycloalkyl,
phenyl substituted C 1 -C 6 alkyl,
—NR 1 R 2 where R 1 and R 2 are cyclized with the attached nitrogen atom to produce pyrrolidiyl, piperidinyl, morphoninyl, 4-methyl piperazinyl or imidazolyl;
X is:
—H,
C 1 -C 6 alkyl,
—F, —Cl, —Br, —I,
—OH,
C 1 -C 6 alkoxy,
cyano,
carboxamide,
carboxyl,
(C 1 -C 6 alkoxy)carbonyl,
A is:
CH,
CH 2 ,
CH-(halogen) where halogen is —F, —Cl, —Br, —I,
CHCH 3 ,
C═O,
C═S,
C—SCH 3 ,
C═NH,
C—NH 2 ,
C—NHCH 3 ,
C—NHCOOCH 3 ,
C—NHCN,
SO 2 ,
N;
B is:
CH 2 ,
CH,
CH-(halogen) where halogen is as defined above,
C═O,
N,
NH,
N—CH 3 ,
D is:
CH,
CH 2 ,
CH-(halogen) where halogen is as defined above,
C═O,
O,
N,
NH,
N—CH 3 ;
and n is 0 or 1, and where is a single or double bond, with the provisos:
(1) that when n is 0, and
A is CH 2 , CH-(halogen) where halogen is as defined above, CHCH 3 , C═O, C═S, C═NH, SO 2 ;
then D is CH 2 , CH-(halogen) where halogen is as defined above, C═O, O, NH, N—CH 3 ;
(2) that when n is 0, and
A is CH, C—SCH 3 , C—NH 2 , C—NHCH 3 , C—NHCOOCH 3 , C—NHCN, N; then
D is CH, N;
(3) that when n is 1, and
A is CH 2 , CH-(halogen) where halogen is as defined above, CHCH 3 , C═O, C═S, C═NH, SO 2 ; and
B is CH 2 , CH-(halogen) where halogen is as defined above, C═O, NH, N—CH 3 ; then
D is CH 2 , C═O, O, NH, N—CH 3 ;
(4) that when n is 1, and
A is CH, C—SCH 3 , C—NH 2 , C—NHCH 3 , C—NHCOOCH 3 , C—NHCN, N; and
B is CH, N; then
D is CH 2 , C═O, O, NH, N—CH 3 ,
(5) that when n is 1, and
A is CH 2 , CHCH 3 , C═O, C═S, C═NH, SO 2 , and
B is CH, N; then
D is CH, N; and pharmaceutically acceptable salts thereof to the human.
6 . A method of treating a sexual deficiency state according to claim 5 where the compound of formula (A) is (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione.
7 . A method of increasing sexual desire, interest or performance in a human who is desirous thereof which comprises administering a sexually useful effective amount of a compound of the formula (A)
where
R 1 , R 2 and R 3 are the same or different and are:
—H,
C 1 -C 6 alkyl,
C 3 -C 5 alkenyl,
C 3 -C 5 alkynyl,
C 3 -C 5 cycloalkyl,
C 4 -C 10 cycloalkyl,
phenyl substituted C 1 -C 6 alkyl,
—NR 1 R 2 where R 1 and R 2 are cyclized with the attached nitrogen atom to produce pyrrolidiyl, piperidinyl, morphoninyl, 4-methyl piperazinyl or imidazolyl;
X is:
—H,
C 1 -C 6 alkyl,
—F, —Cl, —Br, —I,
—OH,
C 1 -C 6 alkoxy,
cyano,
carboxamide,
carboxyl,
(C 1 -C 6 alkoxy)carbonyl,
A is:
CH,
CH 2 ,
CH-(halogen) where halogen is —F, —Cl, —Br, —I,
CHCH 3 ,
C═O,
C═S,
C—SCH 3 ,
C═NH,
C—NH 2 ,
C—NHCH 3 ,
C—NHCOOCH 3 ,
C—NHCN,
SO 2 ,
N;
B is:
CH 2 ,
CH,
CH-(halogen) where halogen is as defined above,
C═O,
N,
NH,
N—CH 3 ,
D is:
CH,
CH 2 ,
CH-(halogen) where halogen is as defined above,
C═O,
O,
N,
NH,
N—CH 3 ;
and n is 0 or 1, and where is a single or double bond, with the provisos:
(1) that when n is 0, and
A is CH 2 , CH-(halogen) where halogen is as defined above, CHCH 3 , C═O, C═S, C═NH, SO 2 ;
then D is CH 2 , CH-(halogen) where halogen is as defined above, C═O, O, NH, N—CH 3 ,
(2) that when n is 0, and
A is CH, C—SCH 3 , C—NH 2 , C—NHCH 3 , C—NHCOOCH 3 , C—NHCN, N; then
D is CH, N;
(3) that when n is 1, and
A is CH 2 , CH-(halogen) where halogen is as defined above, CHCH 3 , C═O, C═S, C═NH, SO 2 ; and
B is CH 2 , CH-(halogen) where halogen is as defined above, C═O, NH, N—CH 3 ; then
D is CH 2 , C═O, O, NH, N—CH 3 ;
(4) that when n is 1, and
A is CH, C—SCH 3 , C—NH 2 , C—NHCH 3 , C—NHCOOCH 3 , C—NHCN, N; and
B is CH, N; then
D is CH 2 , C═O, O, NH, N—CH 3 ;
(5) that when n is 1, and
A is CH 2 , CHCH 3 , C═O, C═S, C═NH, SO 2 , and
B is CH, N; then
D is CH, N; and pharmaceutically acceptable salts thereof to the human.
8 . A method of increasing sexual desire, interest or performance in a human who is desirous thereof according to claim 7 where the compound of formula (A) is (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione.
9 . (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione and pharmaceutically acceptable salts thereof.
10 . A compound according to claim 9 which is (5R)-5-(Methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione malate.Join the waitlist — get patent alerts
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