7-Methyl-8.beta.-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
AssigneeMiles Laboratories, Inc.
InventorsMichael P. Kotick, Robert N. Schut, Joseph O. Polazzi, David L. Leland
Life of this patent
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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: ##STR1## Specific compounds, included within the scope of the foregoing general formula wherein R.sub.1 is H or methyl, R.sub.2 is cyclopropylmethyl or cyclobutylmethyl, R.sub.3 is H, methyl, ethyl or n-propyl and R.sub.4 is H or methyl are useful as mixed analgesics/narcotic antagonists.
Claims44
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:
- ##STR19## ##STR20## wherein R.sub.1 is H or methyl, R.sub.2 is cyclopropylmethyl or cyclobutylmethyl, R.sub.3 is H, methyl, ethyl or n-propyl and R.sub.4 is H or methyl, provided that:
- A. when the molecule is in the B/C cis configuration and R.sub.2 is cyclobutylmethyl,
- i. R.sub.3 is .beta.-methyl, .beta.-ethyl or .beta.-n-propyl when R.sub.1 and R.sub.4 are H,
- ii. R.sub.1 is methyl only when R.sub.4 is H and R.sub.3 is .beta.-methyl, and
- iii. when R.sub.4 is .alpha.-methyl, R.sub.1 is H and R.sub.3 is .beta.-methyl or .beta.-ethyl,
- B. when the molecule is in the B/C cis configuration and R.sub.2 is cyclopropylmethyl,
- i. R.sub.3 is .beta.-methyl and R.sub.4 is H or .alpha.-methyl when R.sub.1 is methyl, and
- ii. R.sub.3 is H and R.sub.4 is .alpha.-methyl when R.sub.1 is H;
- and
- C. when the molecule is in the B/C trans configuration, R.sub.1 is H and R.sub.2 is cyclopropylmethyl,
- i. R.sub.3 is either .alpha.-methyl or H, and
- ii. R.sub.4 is .beta.-methyl.
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.sub.1 is H or methyl, R.sub.2 is cyclopropylmethyl or cyclobutylmethyl, R.sub.3 is H, methyl, ethyl or n-propyl and R.sub.4 is H or methyl, provided that:
- A. when the molecule is in the B/C cis configuration and R.sub.2 is cyclobutylmethyl,
- i. R.sub.3 is .beta.-methyl, .beta.-ethyl or .beta.-n-propyl when R.sub.1 and R.sub.4 are H,
- ii. R.sub.1 is methyl only when R.sub.4 is H and R.sub.3 is .beta.-methyl, and
- iii. when R.sub.4 is .alpha.-methyl, R.sub.1 is H and R.sub.3 is .beta.-methyl or .beta.-ethyl;
- B. when the molecule is in the B/C cis configuration and R.sub.2 is cyclopropylmethyl,
- i. R.sub.3 is .beta.-methyl and R.sub.4 is H or .alpha.-methyl when R.sub.1 is methyl, and
- ii. R.sub.3 is H and R.sub.4 is .alpha.-methyl when R.sub.1 is H, and
- C. when the molecule is in the B/C trans configuration, R.sub.1 is H and R.sub.2 is cyclopropylmethyl,
- i. R.sub.3 is either .alpha.-methyl or H, and
- ii. R.sub.4 is .beta.-methyl.
Dependencies are inferred from the claim text.