US4230712A
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7-Methyl-8β-lower alkyl or 7-methyl-8-lower alkyl B/C cis or trans morphinan-6-one compounds and therapeutic method of treating pain employing them
Assignee: Bayer Corp
•
Filing: 1979-05-21
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Granted: 1980-10-28
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Expires: 1999-05-21
Abstract
Abstract Disclosed are 7-methyl, 8 beta -lower alkyl and 7 methyl-8-lower alkyl substituted B/C Cis or Trans morphinan-6-one compounds characterized by the structural formula: <IMAGE> I Specific compounds, included within the scope of the foregoing general formula wherein R1 is H or methyl, R2 is cyclopropylmethyl or cyclobutylmethyl, R3 is H, methyl, ethyl or n-propyl and R4 is H or methyl are useful as mixed analgesics/narcotic antagonists.
Inventors
- 👤 Michael P. Kotick
- 👤 Robert N. Schut
- 👤 Joseph O. Polazzi
- 👤 David L. Leland
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 14:36
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/08; A; A61; A61P; A61P25/00; A61P25/04; C07D221/00; C07D221/02; C07D221/22; C07D221/28
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
197 words
7-methyl, 8β-lower alkyl and 7-methyl-8-lower alkyl substituted B/C cis or trans morphinan-6-one compounds characterized by the structural formula: ##STR19## ##STR20## wherein R 1 is H or methyl, R 2 is cyclopropylmethyl or cyclobutylmethyl, R 3 is H, methyl, ethyl or n-propyl and R 4 is H or methyl, provided that: A. when the molecule is in the B/C cis configuration and R 2 is cyclobutylmethyl, i. R 3 is β-methyl, β-ethyl or β-n-propyl when R 1 and R 4 are H, ii. R 1 is methyl only when R 4 is H and R 3 is β-methyl, and iii. when R 4 is α-methyl, R 1 is H and R 3 is β-methyl or β-ethyl, B. when the molecule is in the B/C cis configuration and R 2 is cyclopropylmethyl, i. R 3 is β-methyl and R 4 is H or α-methyl when R 1 is methyl, and ii. R 3 is H and R 4 is α-methyl when R 1 is H; and C. when the molecule is in the B/C trans configuration, R 1 is H and R 2 is cyclopropylmethyl, i. R 3 is either α-methyl or H, and ii. R 4 is β-methyl.
Claim 2
Dependent Claim
197 words
7-methyl, 8β-lower alkyl and 7-methyl-8-lower alkyl substituted B/C cis or trans morphinan-6-one compounds characterized by the structural formula: ##STR19## ##STR20## wherein R 1 is H or methyl, R 2 is cyclopropylmethyl or cyclobutylmethyl, R 3 is H, methyl, ethyl or n-propyl and R 4 is H or methyl, provided that: A. when the molecule is in the B/C cis configuration and R 2 is cyclobutylmethyl, i. R 3 is β-methyl, β-ethyl or β-n-propyl when R 1 and R 4 are H, ii. R 1 is methyl only when R 4 is H and R 3 is β-methyl, and iii. when R 4 is α-methyl, R 1 is H and R 3 is β-methyl or β-ethyl, B. when the molecule is in the B/C cis configuration and R 2 is cyclopropylmethyl, i. R 3 is β-methyl and R 4 is H or α-methyl when R 1 is methyl, and ii. R 3 is H and R 4 is α-methyl when R 1 is H; and C. when the molecule is in the B/C trans configuration, R 1 is H and R 2 is cyclopropylmethyl, i. R 3 is either α-methyl or H, and ii. R 4 is β-methyl.
Claim 3
Dependent Claim
18 words
The compounds of claim 1 in the form of their organic or inorganic pharmaceutically acceptable acid addition salts.
Claim 4
Dependent Claim
32 words
A compound as defined by claim 1 wherein R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-methyl and R 4 is H and is in the B/C cis configuration.
Claim 5
Dependent Claim
14 words
The hydrochloric acid and tartaric acid salts of the compound defined by claim 3.
Claim 6
Dependent Claim
35 words
A compound as defined by claim 1 wherein R 1 is CH 3 , R 2 is cyclobutylmethyl, R 3 is β-methyl and R 4 is H and which is in the B/C cis configuration.
Claim 7
Dependent Claim
11 words
The hydrochloric acid salt of the compound defined by claim 5.
Claim 8
Dependent Claim
32 words
A compound as defined by claim 1 wherein R 1 is methyl, R 2 is cyclopropylmethyl, R 3 is β-methyl and R 4 is H and is in the B/C cis configuration.
Claim 9
Dependent Claim
11 words
The hydrochloric acid salt of the compound defined by claim 7.
Claim 10
Dependent Claim
32 words
A compound as defined by claim 1 wherein R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-ethyl and R 4 is H and is in the B/C cis configuration.
Claim 11
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 9.
Claim 12
Dependent Claim
33 words
A compound as defined by claim 1 wherein R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-n-propyl and R 4 is H and which is in the B/C cis configuration.
Claim 13
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 11.
Claim 14
Dependent Claim
33 words
A compound as defined by claim 1 wherein R 1 is H, R 2 is cyclopropylmethyl, R 3 is α-methyl and R 4 is β-methyl and which is in the B/C trans configuration.
Claim 15
Dependent Claim
12 words
The hydrobromic acid addition salt of the compound defined by claim 13.
Claim 16
Dependent Claim
33 words
A compound as defined by claim 1 wherein R 1 is H, R 2 is cyclopropylmethyl, R 3 is H and R 4 is β-methyl and which is in the B/C trans configuration.
Claim 17
Dependent Claim
12 words
The hydrobromic acid addition salt of the compound defined by claim 15.
Claim 18
Dependent Claim
33 words
A compound as defined by claim 1 wherein R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-ethyl and R 4 is α-methyl and which is in the B/C cis configuration.
Claim 19
Dependent Claim
33 words
A compound as defined by claim 1 wherein R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-methyl and R 4 is α-methyl and which is in the B/C cis configuration.
Claim 20
Dependent Claim
33 words
A compound as defined by claim 1 wherein R 1 is H, R 2 is cyclopropylmethyl, R 3 is H and R 4 is α-methyl and which is in the B/C cis configuration.
Claim 21
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 19.
Claim 22
Dependent Claim
33 words
A compound as defined by claim 1 wherein R 1 is methyl, R 2 is cyclopropylmethyl, R 3 is β-methyl and R 4 is α-methyl and which is in the B/C cis configuration.
Claim 23
Dependent Claim
12 words
The hydrochloric acid addition salt of the compound defined by claim 21.
Claim 24
Dependent Claim
206 words
A therapeutic method of treating pain in an individual requiring such treatment which comprises administering to such individual an effective amount of a compound characterized by the formula: ##STR21## wherein R 1 is H or methyl, R 2 is cyclopropylmethyl or cyclobutylmethyl, R 3 is H, methyl, ethyl or n-propyl and R 4 is H or methyl, provided that: A. when the molecule is in the B/C cis configuration and R 2 is cyclobutylmethyl, i. R 3 is β-methyl, β-ethyl or β-n-propyl when R 1 and R 4 are H, ii. R 1 is methyl only when R 4 is H and R 3 is β-methyl, and iii. when R 4 is α-methyl, R 1 is H and R 3 is β-methyl or β-ethyl; B. when the molecule is in the B/C cis configuration and R 2 is cyclopropylmethyl, i. R 3 is β-methyl and R 4 is H or α-methyl when R 1 is methyl, and ii. R 3 is H and R 4 is α-methyl when R 1 is H, and C. when the molecule is in the B/C trans configuration, R 1 is H and R 2 is cyclopropylmethyl, i. R 3 is either α-methyl or H, and ii. R 4 is β-methyl.
Claim 25
Dependent Claim
206 words
A therapeutic method of treating pain in an individual requiring such treatment which comprises administering to such individual an effective amount of a compound characterized by the formula: ##STR21## wherein R 1 is H or methyl, R 2 is cyclopropylmethyl or cyclobutylmethyl, R 3 is H, methyl, ethyl or n-propyl and R 4 is H or methyl, provided that: A. when the molecule is in the B/C cis configuration and R 2 is cyclobutylmethyl, i. R 3 is β-methyl, β-ethyl or β-n-propyl when R 1 and R 4 are H, ii. R 1 is methyl only when R 4 is H and R 3 is β-methyl, and iii. when R 4 is α-methyl, R 1 is H and R 3 is β-methyl or β-ethyl; B. when the molecule is in the B/C cis configuration and R 2 is cyclopropylmethyl, i. R 3 is β-methyl and R 4 is H or α-methyl when R 1 is methyl, and ii. R 3 is H and R 4 is α-methyl when R 1 is H, and C. when the molecule is in the B/C trans configuration, R 1 is H and R 2 is cyclopropylmethyl, i. R 3 is either α-methyl or H, and ii. R 4 is β-methyl.
Claim 26
Dependent Claim
23 words
The method of claim 23 wherein the compound is administered in the form of its organic or inorganic pharmaceutically acceptable acid addition salt.
Claim 27
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-methyl and R 4 is H and is in the B/C cis configuration.
Claim 28
Dependent Claim
19 words
The method of claim 25 wherein the compound administered is in the form of its hydrochloric acid addition salt.
Claim 29
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is methyl, R 2 is cyclobutylmethyl, R 3 is β-methyl and R 4 is H and is in the B/C cis configuration.
Claim 30
Dependent Claim
19 words
The method of claim 27 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 31
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-ethyl and R 4 is H and is in the B/C cis configuration.
Claim 32
Dependent Claim
19 words
The method of claim 29 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 33
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-n-propyl and R 4 is H and is in the B/C cis configuration.
Claim 34
Dependent Claim
19 words
The method of claim 31 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 35
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is H, R 2 is cyclopropylmethyl, R 3 is α-methyl and R 4 is β-methyl and is in the B/C trans configuration.
Claim 36
Dependent Claim
21 words
The method as defined by claim 33 wherein the compound is administered in the form of its hydrobromic acid addition salt.
Claim 37
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is H, R 2 is cyclopropylmethyl, R 3 is H and R 4 is β-methyl and is in the B/C trans configuration.
Claim 38
Dependent Claim
21 words
The method as defined by claim 35 wherein the compound is administered in the form of its hydrobromic acid addition salt.
Claim 39
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-ethyl and R 4 is α-methyl and is in the B/C cis configuration.
Claim 40
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is H, R 2 is cyclobutylmethyl, R 3 is β-methyl and R 4 is α-methyl and is in the B/C cis configuration.
Claim 41
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is H, R 2 is cyclopropylmethyl, R 3 is H and R 4 is α-methyl and is in the B/C cis configuration.
Claim 42
Dependent Claim
21 words
The method as defined by claim 39 wherein the compound is administered in the form of its hydrobromic acid addition salt.
Claim 43
Dependent Claim
40 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is methyl, R 2 is cyclopropyl methyl, R 3 is β-methyl and R 4 is H and is in the B/C cis configuration.
Claim 44
Dependent Claim
21 words
The method as defined by claim 41 wherein the compound is administered in the form of its hydrochloric acid addition salt.
Claim 45
Dependent Claim
39 words
The method as defined by claim 23 wherein the compound administered is characterized in that R 1 is methyl, R 2 is cyclopropylmethyl, R 3 is β-methyl and R 4 is α-methyl and is in the B/C cis configuration.
Claim 46
Dependent Claim
21 words
The method as defined by claim 4 wherein the compound is administered in the form of its hydrochloric acid addition salt.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-28 | 1984-04-28 | 1984-10-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-28 | 1988-04-28 | 1988-10-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-28 | 1992-04-28 | 1992-10-28 | $7700.00 | Window Closed / Lapsed |