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Claims for Patent: 5,604,213

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Claims for Patent: 5,604,213

Title: 17-substituted steroids useful in cancer treatment
Abstract:Compounds of the general formula (1) ##STR1## wherein X represents the residue of the A, B and C rings of a steroid, R represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, R.sup.14 represents a hydrogen atom and R.sup.15 represents a hydrogen atom or an alkyl or alkoxy group of 1-4 carbon atoms, or a hydroxy or alkylcarbonyloxy group of 2 to 5 carbon atoms or R.sup.14 and R.sup.15 together represent a double bond, and R.sup.16 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, in the form of the free bases or phannaceutically acceptable acid addition salts, are useful for treatment of androgen-dependent disorders, especially prostatic cancer, and also oestrogen-dependent disorders such as breast cancer.
Inventor(s): Barrie; Susan E. (Kent, GB3), Jarman; Michael (London, GB3), Potter; Gerard A. (Cheshire, GB3), Hardcastle; Ian R. (Sutton, GB3)
Assignee: British Technology Group Limited (London, GB2)
Application Number:08/315,882
Patent Claims: 1. A compound of the formula (I) ##STR27## wherein X represents the residue of the A, B and C rings of a steroid selected from the group consisting of

androstan-3.alpha.- or 3.beta.-ol,

androst-5-en-3.alpha.- or 3.beta.-ol,

androst-4-en-3-one,

androst-2-ene,

androst-4-ene,

androst-5-ene,

androsta-5,7-dien-3.alpha. or 3.beta.-ol,

androsta-1,4-dien-3-one,

estra-1,3,5[10]-trien-3-ol,

.alpha. -androstan-3-one,

androst-4-ene-3,11-dione,

6-fluoroandrost-4-ene-3-one,

androstan-4-ene-3,6-dione,

each of which, where structurally permissible, can be further derivatised in one or more of the following ways:

to form 3-esters

to have one or more carbon to carbon ring double bonds in any of the 5,6-, 6,7-, 7,8-, 9,11- and 11,12-positions

as 3-oximes

as 3-methylenes

as 3-carboxylates

as 3-nitriles

as 3-nitros

as 3-desoxy derivatives

to have one or more hydroxy, halo, C.sub.1-4 -alkyl, trifluoro-methyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkanoyloxy, benzoyloxy, oxo, methylene or alkenyl substituents in the A, B, or C-ring

to be 19-nor;

R represents a hydrogen atom or an alkyl group of 1-4 carbon atoms;

androsta-3,5-diene,

androsta-3,5-diene-3-ol,

estra-1,3,5[10]-triene and

estra-1,3,5[10]-trien-3-ol,

.alpha. -androstan-3-one:

androst-4-ene-3,11-dione,

6-fluoroandrost-4-ene-3-one,

androstan-4-ene-3,6-dione,

each of which, where structurally permissible, can be further derivatised in one or more of the following ways:

to form 3-esters

to have one or more carbon or carbon ring double bonds in any of the 5,6-, 6,7-, 7,8-, 9,11- and 11,12-positions

as 3-oximes

as 3-methylenes

as 3-carboxylates

as 3-nitriles

as 3-nitros

as 3-desoxy derivatives

to have one or more hydroxy, halo, C.sub.1-4 -alkyl, trifluoro-methyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkanoyloxy, benzoyloxy, oxo, methylene or alkenyl substituents in the A, B, or C-ring

to be 19-nor;

R represents a hydrogen atom or an alkyl group of 1-4 carbon atoms;

R.sup.14 represents a hydrogen atom, a halogen atom or an alkyl group of 1 to 4 carbon atoms;

each of the R.sup.15 substituents independently represents a hydrogen atom or an alkyl or alkoxy group of 1-4 carbon atoms, a hydroxy group or an alkylcarbonyloxy group of 2 to 5 carbon atoms or together represent an oxo or methylene group or R.sup.14 and one of the R.sup.15 groups together represent a double bond and the other R.sup.15 group represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms; and

R.sup.16 represents a hydrogen atom, halogen atom, or an alkyl group of 1 to 4 carbon atoms, in the form of the free bases or pharmaceutically acceptable acid addition salts, but excluding 3.beta.-acetoxy-17-(3-pyridyl)androsta-5,14,16-triene, 3.beta.,15.alpha.- and 3.beta.,15.beta.-diacetoxy-17-(3-pyridyl)androsta-5,16-diene and 3.beta.-methoxy-17-(3-pyridyl-5.alpha.-androst-16-ene.

2. A method of treating an androgen-dependent or estrogen-dependent disorder which comprises administering to a patient in a therapeutically effective dose a compound of the formula (1): ##STR28## wherein X represents the residue of the A, B and C rings of asteroid selected from the group consisting of

androstan-3.alpha.- or 3.beta.-ol,

androst-5-en-3.alpha.- or 3.beta.-ol,

androst-4-en-3-one,

androst-2-ene,

androst-4-ene,

androst-5-ene,

androsta-5,7-dien-3.alpha. or 3.beta.-ol,

androsta-1,4-dien-3-one,

androsta-3,5-diene,

androsta-3,5-dien-3-ol,

estra-1,3,5[10]-triene and

R.sup.14 represents a hydrogen atom, a halogen atom or an alkyl group of 1 to 4 carbon atoms;

each of the R.sup.15 substituents independently represents a hydrogen atom or an alkyl or alkoxy group of 1-4 carbon atoms, a hydroxy group or an alkylcarbonyloxy group of 2 to 5 carbon atoms or together represent an oxo or methylene group or R.sup.14 and one of the R.sup.15 groups together represent a double bond and the other R.sup.15 group represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms; and

R.sup.16 represents a hydrogen atom, halogen atom, or an alkyl group of 1 to 4 carbon atoms, in the form of the free bases or pharmaceutically acceptable acid addition salts.

3. A compound according to claim 1, which is saturated and unsubstituted at the 11- and 12-positions.

4.

17-(3-Pyridyl)androsta-5,16-dien-3.beta.-ol,

17-(3-pyridyl)androsta-3,5,16-triene,

17-(3-pyridyl)androsta-4,16-dien-3-one,

17-(3-pyridyl)estra-1,3,5[10],16-tetraen-3-ol,

17-(3-pyridyl)-5.alpha.-androst-16-en-3.alpha.-ol

and their acid addition salts and 3-esters.

5. A compound according to claim 1 wherein R represents a hydrogen atom.

6.

17-(3-Pyridyl)-5.alpha.-androst-16-en-3-one,

17-(3-pyridyl)-androsta-4,16-diene-3,11-dione,

17-(3-pyridyl)-androsta-3,5,16-trien-3-ol,

6.alpha.- and 6.beta.-fluoro-17-(3-pyridyl)androsta-4,16-dien-3-one,

17-(3-pyridyl)androsta-4,16-dien-3,6-dione,

3.alpha.-trifluoromethyl-17-(3-pyridyl)androst-16-en-3.beta.-ol

and their acid addition salts and 3-esters.

7. 3.beta.-Alkanoyloxy-17-(3-pyridyl)androsta-5,16-dienes in which the alkanoyloxy group has from 2 to 4 carbon atoms.

8. 3.beta.-Acetoxy-17-(3-pyridyl)androsta-5,16-diene.

9. A pharmaceutical composition comprising a compound of claim 1 in association with a pharmaceutically acceptable carrier or diluent.

10. A pharmaceutical composition comprising a compound of claim 3 in association with a pharmaceutically acceptable carrier or diluent.

11. A pharmaceutical composition comprising a compound of claim 1 wherein R represent a hydrogen atom in association with a pharmaceutically acceptable carrier or diluent.

12. A pharmaceutical composition comprising a compound of claim 4 in association with a pharmaceutically acceptable carrier or diluent.

13. A pharmaceutical composition comprising a compound of claim 6 in association with a pharmaceutically acceptable carrier or diluent.

14. A pharmaceutical composition comprising a compound of claim 7 in association with a pharmaceutically acceptable carrier or diluent.

15. A pharmaceutical composition comprising a compound of claim 8 in association with a pharmaceutically acceptable carrier or diluent.

16. A method according to claim 2 wherein the patient has prostatic cancer.

17. A method according to claim 2 wherein the patient has breast cancer.

18. A method according to claim 2 wherein the compound defined in claim 2 is saturated and unsubstituted at the 11- and 12-positions.

19. A method according to claim 2 wherein the compound is selected from the group consisting of:

17-(3-pyridyl)androsta-5,16-dien-3.beta.-ol,

17-(3-pyridyl)androsta-3,5,16-triene,

17-(3-pyridyl)androsta-4,16-dien-3-one,

17-(3-pyridyl)estra-1,3,5[10],16-tetraen-3-ol,

17-(3-pyridyl)-5.alpha.-androst-16-en-3.alpha.-ol

and their acid addition salts and 3-esters.

20. A method according to claim 2 wherein the compound is a 3.beta.-alkanoyloxy-17-(3-pyridyl)androsta-5,16-diene wherein the alkanoyloxy group has 2 to 4 carbon atoms.

21. A method according to claim 2 wherein the compound is 3.beta.-acetoxy-17-(3-pyridyl)androsta-5,16-diene.

22. An orally ingestible solid composition or a sterile injectable liquid composition comprising respectively a solid or liquid pharmaceutically acceptable carrier or diluent and a compound as defined by general formula (1) of claim 2.
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