US4241067A
Expired / Lapsed
US
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14-Amino derivatives of morphine, methods of making them and analgesic compositions containing them
Assignee: Reckitt Benckiser Healthcare UK Ltd
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Filing: 1978-03-15
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Granted: 1980-12-23
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Expires: 1998-03-15
Abstract
Abstract Novel derivatives of morphine having the general formula: ##STR1## wherein R 2 , R 3 , R 4 , R 5 and R 6 are certain specified values, and their pharmaceutically acceptable salts. The compounds exhibit activity in the central nervous system and may be presented in the form of pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable salt thereof, in association with a pharmaceutically acceptable diluent or carrier.
Inventors
- 👤 Ryszard J. Kobylecki
- 👤 Ian G. Guest
- 👤 John W. Lewis
- 👤 Gordon W. Kirby
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 08:29
CPC Classifications
C; C07; C07D; C07D489/00; C07D489/06; A; A61; A61P; A61P1/00; A61P1/12; A61P25/00; A61P25/04
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
155 words
A compound of the general formula: ##STR8## wherein R 2 is methyl or Ar-alkyl C 1-5 ; R 3 is hydrogen, alkyl C 1-12 , alkenyl C 3-8 , cycloalkyl C 3-7 alkyl C 1-4 , Ar-alkyl C 1-5 or Ar-alkenyl C 3-5 , provided that R 3 does not contain the system --CH═CH--attached to the nitrogen atom at position 14; R 4 is hydrogen, alkyl C 1-8 or the group COR 7 in which R 7 is hydrogen, alkyl C 1-11 , alkenyl C 2-7 , Ar, Ar-alkyl C 1-5 , Ar-alkenyl C 2-5 , cycloalkyl C 3-8 or cycloalkyl C 3-8 alkyl C 1-3 ; Ar is phenyl or phenyl subtituted by halogen, alkyl C 1-3 , hydroxy or alkoxy C 1-3 ; R 5 is hydrogen and R 6 is hydroxy; or R 5 and R 6 are together oxygen; the dotted line indicates an optional bond; and its pharmaceutically acceptable salts.
Claim 2
Dependent Claim
155 words
A compound of the general formula: ##STR8## wherein R 2 is methyl or Ar-alkyl C 1-5 ; R 3 is hydrogen, alkyl C 1-12 , alkenyl C 3-8 , cycloalkyl C 3-7 alkyl C 1-4 , Ar-alkyl C 1-5 or Ar-alkenyl C 3-5 , provided that R 3 does not contain the system --CH═CH--attached to the nitrogen atom at position 14; R 4 is hydrogen, alkyl C 1-8 or the group COR 7 in which R 7 is hydrogen, alkyl C 1-11 , alkenyl C 2-7 , Ar, Ar-alkyl C 1-5 , Ar-alkenyl C 2-5 , cycloalkyl C 3-8 or cycloalkyl C 3-8 alkyl C 1-3 ; Ar is phenyl or phenyl subtituted by halogen, alkyl C 1-3 , hydroxy or alkoxy C 1-3 ; R 5 is hydrogen and R 6 is hydroxy; or R 5 and R 6 are together oxygen; the dotted line indicates an optional bond; and its pharmaceutically acceptable salts.
Claim 3
Dependent Claim
8 words
The compound of claim 1 which is 14-β-aminomorphinone.
Claim 4
Dependent Claim
8 words
The compound of claim 1 which is 14-β-pentanoylaminomorphinone.
Claim 5
Dependent Claim
8 words
The compound of claim 1 which is 14-β-hexanoylaminomorphinone.
Claim 6
Dependent Claim
8 words
The compound of claim 1 which is 14-β-heptanoylaminomorphinone.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is 14-β-octanoylaminomorphinone.
Claim 8
Dependent Claim
8 words
The compound of claim 1 which is 14-β-butylaminomorphinone.
Claim 9
Dependent Claim
8 words
The compound of claim 1 which is 14-β-pentylaminomorphinone.
Claim 10
Dependent Claim
8 words
The compound of claim 1 which is 14-β-hexylaminomorphinone.
Claim 11
Dependent Claim
8 words
The compound of claim 1 which is 14-β-heptylaminomorphinone.
Claim 12
Dependent Claim
8 words
The compound of claim 1 which is 14-β-octylaminomorphinone.
Claim 13
Dependent Claim
62 words
A process for the preparation of a compound as claimed in claim 1 which process comprises treating a compound of the general Formula II: ##STR9## in which R 2 ,R 3 ,R 4 ,R 5 ,R 6 and the dotted line are as defined in claim 1. with boron tribromide at a temperature in the range of from -30° to -10° C.
Claim 14
Dependent Claim
80 words
A process for the preparation of a compound of Formula I as claimed in claim 1 wherein R 5 and R 6 are together oxygen which process comprises treating the compound of the general Formula II in which R 2 ,R 3 ,R 4 and the dotted line are as defined in claim 1 and in which both R 5 and R 6 are methoxy, with boron tribromide at a temperature in the range of from -30° to -10° C.
Claim 15
Dependent Claim
42 words
A process for the preparation of 14-β-aminomorphinone which process comprises treating 14-β-nitrocodeinone or its dimethyl ketal in methylene chloride with boron tribromide at a temperature in the range of from -30° to -10° C., and reducing the resultant 14-β-nitromorphinone with sodium dithionite.
Claim 16
Dependent Claim
42 words
A process for the preparation of 14-β-aminomorphinone which process comprises treating 14-β-nitrocodeinone or its dimethyl ketal in methylene chloride with boron tribromide at a temperature in the range of from -30° to -10° C., and reducing the resultant 14-β-nitromorphinone with sodium dithionite.
Claim 17
Dependent Claim
33 words
A pharmaceutical composition for the relief of pain which comprises at least one compound as claimed in claim 1, or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable diluent or carrier.
Claim 18
Dependent Claim
36 words
A pharmaceutical composition for the relief of pain according to claim 15 in unit dosage form for oral administration which contains from 0.1 to 10 mg of the said compound or salt thereof per unit dosage.
Claim 19
Dependent Claim
39 words
A pharmaceutical composition for the relief of pain according to claim 16 in unit dosage form for parenteral administration which contains from 0.1 to 10 mg of the said compound or salt thereof per 1 ml of the composition.
References Cited (Backward Citations)
US3819635A
Cited
US4017497A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-12-23 | 1984-06-23 | 1984-12-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-23 | 1988-06-23 | 1988-12-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-23 | 1992-06-23 | 1992-12-23 | $7700.00 | Window Closed / Lapsed |