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US4272540A
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14-Methoxymorphinan-6-one compounds and therapeutic methods of treating pain and drug dependence with them
Assignee: Sisa Inc
•
Filing: 1979-04-24
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Granted: 1981-06-09
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Expires: 1999-04-24
Abstract
Abstract Disclosed are 14-methoxy substituted 3-hydroxy or 3-methoxy -6-one morphinans characterized by the structural formula: <IMAGE> wherein R is H or methyl; R1 is H, alpha methyl or beta methyl; and R2 is cyclobutylmethyl, cyclopropylmethyl, tetrahydrofurfuryl or dimethylallyl. The compounds of the present invention are variously useful as analgesics, narcotic antagonists and mixed analgesics/narcotic antagonists.
Inventors
- 👤 Raj K. Razdan
- 👤 Anil C. Ghosh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 16:22
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/22; C07D221/28; A; A61; A61P; A61P25/00; A61P25/04
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
44 words
14-methoxy substituted 3-hydroxy or 3-methoxy-6-one morphinans characterized by the formula: ##STR13## where R is H or methyl; R 1 is H, α-methyl or β-methyl, and R 2 is cyclobutylmethyl, cyclopropylmethyl, tetrahydrofurfuryl or dimethylallyl, provided that when R 2 is dimethylallyl, R 1 is methyl.
Claim 2
Dependent Claim
44 words
14-methoxy substituted 3-hydroxy or 3-methoxy-6-one morphinans characterized by the formula: ##STR13## where R is H or methyl; R 1 is H, α-methyl or β-methyl, and R 2 is cyclobutylmethyl, cyclopropylmethyl, tetrahydrofurfuryl or dimethylallyl, provided that when R 2 is dimethylallyl, R 1 is methyl.
Claim 3
Dependent Claim
16 words
The morphinans of claim 1 in the form of their pharmacologically acceptable, non-toxic acid addition salts.
Claim 4
Dependent Claim
22 words
A compound as defined by claim 1 wherein R is C 3 , R 1 is H and R 2 is cyclobutylmethyl.
Claim 5
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 3.
Claim 6
Dependent Claim
22 words
A compound as defined by claim 1 wherein R is CH 3 , R 1 is H and R 2 is cyclopropylmethyl.
Claim 7
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 5.
Claim 8
Dependent Claim
20 words
A compound as defined by claim 1 wherein R is H, R 1 is H and R 2 is cyclobutylmethyl.
Claim 9
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 7.
Claim 10
Dependent Claim
20 words
A compound as defined by claim 1 wherein R is H, R 1 is H and R 2 is cyclopropylmethyl.
Claim 11
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 9.
Claim 12
Dependent Claim
20 words
A compound as defined by claim 1 wherein R is H, R 1 is α-methyl and R 2 is cyclopropylmethyl.
Claim 13
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 11.
Claim 14
Dependent Claim
20 words
A compound as defined by claim 1 wherein R is H, R 1 is α-methyl and R 2 is cyclobutylmethyl.
Claim 15
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 13.
Claim 16
Dependent Claim
20 words
A compound as defined by claim 1 wherein R is H, R 1 is H and R 2 is tetrahydrofurfuryl.
Claim 17
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 15.
Claim 18
Dependent Claim
22 words
A compound as defined by claim 1 wherein R is CH 3 , R 1 is H and R 2 is tetrahydrofurfuryl.
Claim 19
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 17.
Claim 20
Dependent Claim
21 words
A compound as defined by claim 1 wherein R is H, R 1 is α-CH 3 and R 2 is dimethylallyl.
Claim 21
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 19.
Claim 22
Dependent Claim
22 words
A compound as defined by claim 1 wherein R is CH 3 , R 1 is α-methyl and R 2 is tetrahydrofurfuryl.
Claim 23
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 21.
Claim 24
Dependent Claim
22 words
A compound as defined by claim 1 wherein R is CH 3 , R 1 is β-methyl and R 2 is cyclopropylmethyl.
Claim 25
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 23.
Claim 26
Dependent Claim
23 words
A compound as defined by claim 1 wherein R is CH 3 , R 1 is β-CH 3 and R 2 is cyclobutylmethyl.
Claim 27
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 25.
Claim 28
Dependent Claim
21 words
A compound as defined by claim 1 wherein R is H, R 1 is β-CH 3 and R 2 is cyclobutylmethyl.
Claim 29
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 27.
Claim 30
Dependent Claim
21 words
A compound as defined by claim 1 wherein R is H, R 1 is β-CH 3 and R 2 is cyclopropylmethyl.
Claim 31
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 29.
Claim 32
Dependent Claim
7 words
As a composition of matter 17-cyclopropylmethyl-14-methoxy-8β-methyl-morphinan-3,6-diol hydrochloride.
Claim 33
Dependent Claim
7 words
As a composition of matter 17-cyclopropylmethyl-14-methoxy-8β-methyl-morphinan-3,6-diol hydrochloride.
Claim 34
Dependent Claim
49 words
A therapeutic method for treating pain in an individual for whom such therapy is indicated, which method comprises administering to the individual an effective analgesic amount of a compound selected from the group of 17-cyclobutylmethyl-3,14-dimethoxymorphinan-6-one, 17-cyclobutylmethyl-3-hydroxy-14-methoxymorphinan-6-one, 17-tetrahydrofurfuryl-3-hydroxy-14-methoxymorphinan-6-one, 17-tetrahydrofurfuryl-3,14-dimethoxymorphinan-6-one, 17-dimethylallyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one, 17-tetrahydrofurfuryl-3,14-dimethoxy-8α-methylmorphinan-6-one or a pharmacological acceptable, non-toxic acid addition salt thereof.
Claim 35
Dependent Claim
49 words
A therapeutic method for treating pain in an individual for whom such therapy is indicated, which method comprises administering to the individual an effective analgesic amount of a compound selected from the group of 17-cyclobutylmethyl-3,14-dimethoxymorphinan-6-one, 17-cyclobutylmethyl-3-hydroxy-14-methoxymorphinan-6-one, 17-tetrahydrofurfuryl-3-hydroxy-14-methoxymorphinan-6-one, 17-tetrahydrofurfuryl-3,14-dimethoxymorphinan-6-one, 17-dimethylallyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one, 17-tetrahydrofurfuryl-3,14-dimethoxy-8α-methylmorphinan-6-one or a pharmacological acceptable, non-toxic acid addition salt thereof.
Claim 36
Dependent Claim
20 words
The method of claim 32 wherein the compound is administered is in the form of its hydrochloric acid addition salt.
Claim 37
Dependent Claim
51 words
A therapeutic method for treating drug dependence in an individual for whom such therapy is indicated, which method comprises administering to the individual an effective narcotic antagonist amount of a compound selected from the group of 17-cyclopropylmethyl-3,14-dimethoxy-8β-methylmophinan-6-one; 17-cyclopropylmethyl-3-hydroxy-14-methoxy-8β-methylmorphinan-6-one; 17-cyclobutylmethyl-3,14-dimethoxy-8β-methylmorphinan-6-one; 17-cyclobutylmethyl-3-hydroxy-14-methoxy-8β-methylmorphinan-6-one; 17-cyclopropylmethyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one; 17-cyclopropylmethyl-14-methoxy-8β-methylmorphinan-3,6-diol or a pharmacologically acceptable, non-toxic acid addition salt thereof.
Claim 38
Dependent Claim
51 words
A therapeutic method for treating drug dependence in an individual for whom such therapy is indicated, which method comprises administering to the individual an effective narcotic antagonist amount of a compound selected from the group of 17-cyclopropylmethyl-3,14-dimethoxy-8β-methylmophinan-6-one; 17-cyclopropylmethyl-3-hydroxy-14-methoxy-8β-methylmorphinan-6-one; 17-cyclobutylmethyl-3,14-dimethoxy-8β-methylmorphinan-6-one; 17-cyclobutylmethyl-3-hydroxy-14-methoxy-8β-methylmorphinan-6-one; 17-cyclopropylmethyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one; 17-cyclopropylmethyl-14-methoxy-8β-methylmorphinan-3,6-diol or a pharmacologically acceptable, non-toxic acid addition salt thereof.
Claim 39
Dependent Claim
19 words
The method of claim 34 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 40
Dependent Claim
10 words
The method of claim 34 wherein the compound is 17-cyclopropylmethyl-3-hydroxy-14-methoxy-8β-methylmorphinan-6-one.
Claim 41
Dependent Claim
19 words
The method of claim 36 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 42
Dependent Claim
51 words
A therapeutic method for treating pain without liability of drug dependence in an individual for whom such therapy is indicated which method comprises administering to the individual an effective analgesic amount of a compound selected from the group of 17-cyclopropylmethyl-3,14-dimethoxymorphinan-6-one, 17-cyclopropylmethyl-3-hydroxy-14-methoxymorphinan-6-one, 17-cyclobutylmethyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one or a pharmacologically acceptable, non-toxic acid addition salt thereof.
Claim 43
Dependent Claim
51 words
A therapeutic method for treating pain without liability of drug dependence in an individual for whom such therapy is indicated which method comprises administering to the individual an effective analgesic amount of a compound selected from the group of 17-cyclopropylmethyl-3,14-dimethoxymorphinan-6-one, 17-cyclopropylmethyl-3-hydroxy-14-methoxymorphinan-6-one, 17-cyclobutylmethyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one or a pharmacologically acceptable, non-toxic acid addition salt thereof.
Claim 44
Dependent Claim
19 words
The method of claim 38 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 45
Dependent Claim
11 words
The method of claim 38 wherein the compound administered is 17-cyclopropylmethyl-3,14-dimethoxymorphinan-6-one.
Claim 46
Dependent Claim
19 words
The method of claim 40 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 47
Dependent Claim
11 words
The method of claim 38 wherein the compound administered is 17-cyclopropylmethyl-3-hydroxy-14-methoxymorphinan-6-one.
Claim 48
Dependent Claim
20 words
The method of claim 42 wherein the compound i is administered in the form of its hydrochloric acid addition salt.
Claim 49
Dependent Claim
11 words
The method of claim 38 wherein the compound administered is 17-cyclobutylmethyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one.
Claim 50
Dependent Claim
19 words
The method of claim 44 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 51
Dependent Claim
12 words
The morphinans of claim 2 in the form of their tartrate salts.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-06-08 | 1984-12-08 | 1985-06-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-08 | 1988-12-08 | 1989-06-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-08 | 1992-12-08 | 1993-06-09 | $7700.00 | Window Closed / Lapsed |