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Claims for Patent: 4,237,126

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Claims for Patent: 4,237,126

Title: 2.beta., 16.beta.-bis-piperidino-androstanes
Abstract:New and pharmacologically useful pharmaceutically acceptable acid addition salts are disclosed for the 16.beta.-mono-quaternary ammonium derivatives of either the 2.beta., 16.beta.-bis-piperdino-3-.alpha., 17.beta.-dihydroxy-5.alpha.-androstane 3.alpha., 17.beta.-di-lower aliphatic esters of the 2.beta., 16.beta.-bis-piperidino-3.alpha.-hydroxy-5.alpha.-androstane-3.alpha.-lowe r aliphatic esters, which salts are surprisingly relatively stable in aqueous solutions, so that they provide stable aqueous injection preparations.
Inventor(s): Carlyle; Ian C. (Hamilton, GB6), Sleigh; Thomas (Wishaw, GB6), Savage; David S. (Glasgow, GB6)
Assignee: Akzona Incorporated (Asheville, NC)
Application Number:06/067,878
Patent Claims: 1. A pharmaceutically acceptable acid addition salt of the 16.beta.-mono-quaternary ammonium derivative of either a 3.alpha.,17.beta.-di-lower aliphatic ester of 2.beta.,16.beta.-dipiperidino-3.alpha.,17.beta.-dihydroxy-5.alpha.-androst ane or a 3.alpha.-lower aliphatic ester of 2.beta.,16.beta.-dipiperidino-3.alpha.-hydroxy-5.alpha.-androstane.

2. Acid addition salt according to claim 1 of a compound of the general formula: ##STR2## wherein: (a) R represents hydrogen or the moiety --OR.sub.2 ;

(b) R.sub.1 and R.sub.2 each represent an unsubstituted acyl group derived from a lower aliphatic carboxylic acid of one to about six carbons;

(c) ALK is an alkyl, alkenyl or alkynyl group of one to about four carbon atoms; and

(d) A.sup..crclbar. represents a pharmaceutically acceptable organic or inorganic anion.

3. The acid addition salt of a compound of claim 2 wherein at least one of R.sub.1 and R.sub.2 is acetyl.

4. The acid addition salt of a compound of claim 2 wherein A.sup..crclbar. is selected from the group consisting of methyl-sulfate, p-toluene sulfonate, chloride, bromide and iodide.

5. The acid addition salt of a compound of claim 2 wherein ALK is methyl.

6. The acid addition salt of a compound of claim 1 wherein the salt is derived from one of the acids selected from the group consisting of hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, sulphuric acid, phosphoric acid, acetic acid, propronic acid, butyric acid, caproic acid, malonic acid, succinic acid, glutaric acid, maleic acid, fumaric acid, tartaric acid, malic acid, pyruvic acid, lactic acid, and citric acid.

7. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane-3.alpha.,17.beta.-diol diacetate 16.beta.N-methobromide hydrochloride.

8. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane-3.alpha.,17.beta.-diol 3.alpha.-proprionate 17.beta.-acetate 16.beta.N-methobromide hydrochloride.

9. 2.beta.,16.beta.-dipiperdino-5.alpha.-androstane-3.alpha.-ol 3.alpha.-acetate 16.beta.N-methobromide hydrochloride.

10. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane-3.alpha.-ol 3.alpha.-acetate 16.beta.N-allylobromide hydrochloride.

11. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane-3.alpha.-ol 3.alpha.-acetate 16.beta.N-propargylobromide hydrochloride.

12. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane 3.alpha.,17.beta.-diol diacetate 16.beta.N-methobromide hydrobromide.

13. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane-3.alpha.,17.beta .-diol 3.alpha.-butyrate 17.beta.-acetate 16.beta.N-methobromide hydrobromide.

14. 2.beta.,16 .beta.-dipiperidino-5.alpha.-androstane-3.alpha.,17.beta.-diol diacetate 16.beta.N-methobromide maleate.

15. 2.beta.,16.beta.-dipiperidin o-5.alpha.-androstane-3.alpha.,17.beta.-diol, 3.alpha.-butyrate 17.beta.-acetate 16.beta.N-methobromide maleate.

16. 2.beta.,16.beta.-dipiperidino-5.alpha.-andros tane-3.alpha.,17.beta.-diol diacetate 16.beta.N-methobromide citrate.

17. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane-3.alpha.,17.bet a.-diol 3.alpha.-propionate 17.beta.-acetate 16.beta.N-methobromide citrate.

18. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane-3.alpha.,17.beta.-dio l diacetate 16.beta.N-methobromide phosphate.

19. 2.beta.,16.beta.-dipiperidino-5.alpha.-an drostane-3.alpha.,17.beta.-diol 3.alpha. pivalate 17.beta.-acetate 16.beta.N-methobromide phosphate.

20. 2.beta.,16.beta.-dipiperidino- 5.alpha.-androstane-3.alpha.,17.beta.-diol 3.alpha. pivalate 17.beta.-acetate 16.beta.N-methobromide tartrate.

21. A pharmaceutical composition useful as a neuromuscular blocking agent, comprising:

(A) a pharmaceutically effective amount of a pharmaceutically acceptable acid addition salt of the 16.beta.-mono-quaternary ammonium derivative of either a 3.alpha.,17.beta.-di-lower aliphatic ester of a 3.alpha.-lower aliphatic ester of 2.beta.,16.beta.-dipiperidino-3.alpha.-hydroxy-5.alpha.-androstane;

and

(B) water,

whereby the acid addition salt is formed in situ.

22. The composition of claim 21, wherein a pharmaceutically acceptable buffer system is added to buffer the composition in the range of from about pH 3 to about pH 4.5.

23. The composition of claim 21 or 22, wherein a pharmaceutically acceptable amount of an acid addition salt of 2.beta.,16.beta.-dipiperidino-3.alpha.,17.beta.-dihydroxy-5.alpha.-androst ane 3.alpha.,17.beta.-diacetate 16.beta.-methobromide is present.

24. The composition of claim 21, wherein the acid addition salt is of a compound of the formula: ##STR3## wherein: (a) R represents hydrogen or the moiety --OR.sub.2 ;

(b) R.sub.1 and R.sub.2 each represent an unsubstituted acyl group derived from a lower aliphatic carboxylic acid of one to about six carbons;

(c) ALK is an alkyl, alkenyl, or alkynyl group of one to about four carbon atoms; and

(d) A.sup..crclbar. represents a pharmaceutically acceptable organic or inorganic anion;

is present.

25. Acid addition salt according to claim 1 having the general formula: ##STR4## wherein:

(a) R represents hydrogen or the moiety --OR.sub.2 ;

(b) R.sub.1 and R.sub.2 each represent an unsubstituted acyl group derived from a lower aliphatic carboxylic acid of one to about six carbons;

(c) ALK is an alkyl, alkenyl or alkynyl group of one to about four carbon atoms; and

(d) A.sup..crclbar. and X.sup..crclbar. each represents a pharmaceutically acceptable organic or inorganic anion.

26. The salt of claim 25 where X.sup..crclbar. is the same anion as A.sup..crclbar..

27. A pharmaceutical composition useful as a neuromuscular blocking agent comprising

(a) a neuromuscular blocking effective amount of a pharmaceutically acceptable acid addition salt of the 16.beta.-monoquaternary ammonium derivative of either a 3.alpha.,17.beta.-di-lower aliphatic ester or a 3.alpha.-lower aliphatic ester of 2.beta.,16.beta.-dipiperidino-3.alpha.-hydroxy-5.alpha.-androstane, and

(b) water.

28. The composition of claim 27 further comprising a pharmaceutically acceptable buffer system to buffer the composition to a pH ranging from about 3 to about 4.5.

29. The composition of claim 27 or 28 wherein said acid addition salt is an acid addition salt of 2.beta.,16.beta.-dipiperidino-3.alpha.,17.beta.-dihydroxy-5.alpha.-androst ane 3.alpha.,17.beta.-diacetate 16.beta.-methobromide.

30. The composition of claim 27 wherein said acid addition salt is of a compound of the formula: ##STR5## wherein: (a) R is hydrogen or the moiety --OR.sub.2 ;

(b) R.sub.1 and R.sub.2 each represent an unsubstituted acyl group derived from a lower aliphatic carboxylic acid of one to about six carbons;

(c) ALK is an alkyl, alkenyl, or alkynyl group of one to about four carbon atoms; and

(d) A.sup..crclbar. represents a pharmaceutically acceptable organic or inorganic anion.
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