US4608374A
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11-substituted 5H,11H-pyrrolo[2,1-c][1,4]benzoxazepines as antipsychotic and analgesic agents
Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1983-11-07
•
Granted: 1986-08-26
•
Expires: 2003-11-07
Abstract
Abstract There are described to novel 11-substituted 5H,11H-pyrrolo[2,1-c][1,4]benzoxazepines of the general formula ##STR1## where m and n are each independently 0, 1 or 2 and m+n is 1 or 2, X and Y are each independently hydrogen, loweralkyl or halogen, and R is hydrogen, cyano, --C(NH 2 )NOH, ##STR2## unsubstituted loweralkyl, or substituted loweralkyl having one to three substituents each of which being independently cyano, hydroxy, cyclohexyl, furyl, thienyl, ##STR3## k being 1, 2 or 3, W being each independently hydrogen, halogen, hydroxy, loweralkyl, trifluoromethyl, loweralkoxy, nitro, amino, diloweralkylamino, phenoxy, or benzyloxy, and Z being hydrogen, loweralkyl or halogen, which are useful as antipsychotic and analgesic agents; novel intermediate compounds therefor; and methods of synthesizing the foregoing compounds.
Inventors
- 👤 Richard C. Effland
- 👤 Larry Davis
- 👤 Kevin J. Kapples
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 16:46
CPC Classifications
C; C07; C07D; C07D491/00; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/33; C07D207/333; A; A61; A61P; A61P25/00; A61P25/04; A61P25/18; A61P25/24; A61P25/26; C07D401/00; C07D401/02; C07D401/06
Claims Analysis
Total Claims: 101
Claim 1
Independent Claim
100 words
A compound of the formula ##STR35## where m and n are each independently 0, 1 or 2 and m+n is 1 or 2, X and Y are each independently hydrogen, loweralkyl or halogen, and R is hydrogen, cyano, --C(NH 2 )NOH, ##STR36## unsubstituted loweralkyl, or substituted loweralkyl having one to three substituents each of which being independently cyano, hydroxy, cyclohexyl, furyl, thienyl, ##STR37## k being 1, 2 or 3, W being each independently hydrogen, halogen, hydroxy, loweralkyl, trifluoromethyl, loweralkoxy, nitro, amino, diloweralkylamino, phenoxy, or benzyloxy, and Z being hydrogen, loweralkyl or halogen, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
100 words
A compound of the formula ##STR35## where m and n are each independently 0, 1 or 2 and m+n is 1 or 2, X and Y are each independently hydrogen, loweralkyl or halogen, and R is hydrogen, cyano, --C(NH 2 )NOH, ##STR36## unsubstituted loweralkyl, or substituted loweralkyl having one to three substituents each of which being independently cyano, hydroxy, cyclohexyl, furyl, thienyl, ##STR37## k being 1, 2 or 3, W being each independently hydrogen, halogen, hydroxy, loweralkyl, trifluoromethyl, loweralkoxy, nitro, amino, diloweralkylamino, phenoxy, or benzyloxy, and Z being hydrogen, loweralkyl or halogen, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
15 words
The compound as defined in claim 1, where m is 1 and n is 1.
Claim 4
Dependent Claim
11 words
The compound as defined in claim 2, where Y is methyl.
Claim 5
Dependent Claim
11 words
The compound as defined in claim 3, where X is hydrogen.
Claim 6
Dependent Claim
11 words
The compound as defined in claim 4, where R is methyl.
Claim 7
Dependent Claim
10 words
The compound as defined in claim 5, which is 3-methyl-11-[(1-methyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 8
Dependent Claim
11 words
The compound as defined in claim 2, where Y is hydrogen.
Claim 9
Dependent Claim
11 words
The compound as defined in claim 7, where X is chlorine.
Claim 10
Dependent Claim
11 words
The compound as defined in claim 8, where R is methyl.
Claim 11
Dependent Claim
10 words
The compound as defined in claim 9, which is 8-chloro-11-[(1-methyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 12
Dependent Claim
10 words
The compound as defined in claim 9, which is 7-chloro-11-[(1-methyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 13
Dependent Claim
11 words
The compound as defined in claim 8, where R is hydrogen.
Claim 14
Dependent Claim
10 words
The compound as defined in claim 12, which is 7-chloro-11-(piperidin-4-yl)-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 15
Dependent Claim
11 words
The compound as defined in claim 7, where X is hydrogen.
Claim 16
Dependent Claim
14 words
The compound as defined in claim 14, where R is hydrogen, which is 11-(piperidin-4-yl)-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 17
Dependent Claim
14 words
The compound as defined in claim 14, where R is cyano, which is 11-[(1-cyano)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 18
Dependent Claim
16 words
The compound as defined in claim 14, where R is --C(NH 2 )NOH, which is 11-[(1-carboxamidoxime)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 19
Dependent Claim
15 words
The compound as defined in claim 14, where R is ##STR38## which is N-phenyl-4-(5H,11-pyrrolo[2,1-c][1,4]benzoxazepine-11-yl)-1-piperidine carboxamide.
Claim 20
Dependent Claim
13 words
The compound as defined in claim 14, where R is an unsubstituted loweralkyl.
Claim 21
Dependent Claim
14 words
The compound as defined in claim 19, where R is methyl, which is 11-[(1-methyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 22
Dependent Claim
14 words
The compound as defined in claim 19, where R is ethyl, which is 11-[(1-ethyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazpine.
Claim 23
Dependent Claim
14 words
The compound as defined in claim 19, where R is propyl, which is 11-[(1-propyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 24
Dependent Claim
14 words
The compound as defined in claim 19, where R is isopropyl, which is 11-[1-(1-methylethyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 25
Dependent Claim
14 words
The compound as defined in claim 19, where R is butyl, which is 11-[(1-butyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 26
Dependent Claim
29 words
The compound as defined in claim 14, wherein R is a substituted loweralkyl having one to three substituents each of which being independently cyano, hydroxy, cyclohexyl, furyl, thienyl, ##STR39##
Claim 27
Dependent Claim
14 words
The compound as defined in claim 25, where the substituted loweralkyl has three substituents.
Claim 28
Dependent Claim
14 words
The compound as defined in claim 26, where R is ##STR40## which is 11-{1-[(3-cyano-3,3-diphenyl)-propyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 29
Dependent Claim
14 words
The compound as defined in claim 26, where R is ##STR41## which is 11-{1-[(3-cyclohexyl-3-hydroxy-3-phenyl)propyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 30
Dependent Claim
14 words
The compound as defined in claim 25, where the substituted loweralkyl has two substituents.
Claim 31
Dependent Claim
14 words
The compound as defined in claim 29, where R is ##STR42## which is 11-{[1-(4-bis-4-fluorophenyl)-butyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 32
Dependent Claim
14 words
The compound as defined in claim 29, where R is ##STR43## which is 11-{1-[4-(4-fluorophenyl)-butan-4-ol]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 33
Dependent Claim
15 words
The compound as defined in claim 25, where the substituted loweralkyl has a single substituent.
Claim 34
Dependent Claim
16 words
The compound as defined in claim 32 where the single substituent on the loweralkyl is phenyl.
Claim 35
Dependent Claim
14 words
The compound as defined in claim 33, where R is benzyl, which is 11-[(1-benzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 36
Dependent Claim
14 words
The compound as defined in claim 33, where R is ##STR44## which is 11-{1-[2-(phenyl)ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 37
Dependent Claim
14 words
The compound as defined in claim 33, where R is ##STR45## which is 11-{1-[3-(phenyl)propyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 38
Dependent Claim
14 words
The compound as defined in claim 33, where R is ##STR46## which is 11-{1-[(2-phenyl)propyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 39
Dependent Claim
17 words
The compound as defined in claim 25, where the single substituent on the loweralkyl is a phenoxy.
Claim 40
Dependent Claim
14 words
The compound as defined in claim 38, where R is ##STR47## which is 11-{1-[2-(phenoxy)ethyl]piperidin-4-yl}-5H,11-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 41
Dependent Claim
14 words
The compound as defined in claim 38, where R is ##STR48## which is 11-{1-[3-(phenoxy)propyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 42
Dependent Claim
38 words
The compound as defined in claim 25, where R is a loweralkyl substituted with a phenyl group having one to three substituents each of which being independently halogen, hydroxy, loweralkyl, trifluoromethyl, loweralkoxy, nitro, amino, diloweralkylamino, phenoxy, or benzyloxy.
Claim 43
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR49## which is 11-[1-(4-methoxybenzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 44
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR50## which is 11-[1-(4-chlorobenzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 45
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR51## which is 11-[1-(2-fluorobenzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 46
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR52## which is 11-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 47
Dependent Claim
14 words
Th compound as defined in claim 41, where R is ##STR53## which is 11-[1-(3-trifluoromethylbenzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 48
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR54## which is 11-[1-(2,4,6-trimethylbenzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 49
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR55## which is 11-{1-[2-(4-methoxyphenyl)ethyl]-piperdin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 50
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR56## which is 11-{1-[2-(4-fluorophenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 51
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR57## which is 11-{1-[2-(4-methylphenyl)-ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 52
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR58## which is 11-{1-[2-(4-ethoxyphenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 53
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR59## which is 11-{1-[2-(4-chlorophenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 54
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR60## which is 11-{1-[2-(4-nitrophenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 55
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR61## which is 11-{1-[2-(4-benzyloxyphenyl)-ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 56
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR62## which is 11-{1-[2-(3,4-dichlorophenyl)-ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 57
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR63## which is 11-{1-[2-(3,4-dimethoxyphenyl)-ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 58
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR64## which is 11-{1-[2-(4-dimethylaminophenyl)ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 59
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR65## which is 11-{1-[2-(2-methoxyphenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 60
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR66## which is 11-{1-[2-(4-hydroxyphenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 61
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR67## which is 11-{1-[2-(3-methoxyphenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo{2,1-c][1,4]benzoxazepine.
Claim 62
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR68## which is 11-{1-[2-(2,3-dimethoxyphenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 63
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR69## which is 11-{1-[2-(3-trifluoromethylphenyl)-ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 64
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR70## which is 11-{1-[2-(3-chlorophenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 65
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR71## which is 11-{1-[2-(3,4,5-trimethoxyphenyl)-ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 66
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR72## which is 11-{1-[2-(4-hydroxy-3-methoxyphenyl)ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 67
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR73## which is 11-{1-[2-(4-trifluoromethylphenyl)-ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 68
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR74## which is 11-{1-[2-(2-fluorophenyl)ethyl]-piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 69
Dependent Claim
14 words
The compound as defined in claim 41, where R is ##STR75## which is 11-{1-[2-(2-trifluoromethylphenyl)-ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxamide.
Claim 70
Dependent Claim
17 words
The compound as defined in claim 25, where R is a loweralkyl substituted with furyl, thienyl, ##STR76##
Claim 71
Dependent Claim
15 words
The compound as defined in claim 69, where R is ##STR77## which is 11-{1-[2-(1,3-dihydro-2-oxo-2H-benzimidazol-1yl)ethyl]piperidin-4-yl}-5H,11H, pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 72
Dependent Claim
15 words
The compound as defined in claim 69, where R is ##STR78## which is 11-{1-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl}piperidin -4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 73
Dependent Claim
14 words
The compound as defined in claim 69, where R is ##STR79## which is 11-{1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 74
Dependent Claim
14 words
The compound as defined in claim 69, where R is ##STR80## which is 11-{1-[3-(2-methylindol-3-yl)-propyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 75
Dependent Claim
14 words
The compound as defined in claim 69, where R is ##STR81## which is 11-[1-(2-furanylmethyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 76
Dependent Claim
14 words
The compound as defined in claim 69, where R is ##STR82## which is 11-{1-[2-(2-thienyl)ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 77
Dependent Claim
14 words
The compound as defined in claim 69, where R is ##STR83## which is 11-[1-(3-phenylpropan-3-one)-piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 78
Dependent Claim
14 words
The compound as defined in claim 69, where R is ##STR84## which is 11-{1-[3-(4-chlorophenyl)-propan-3-one)]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 79
Dependent Claim
14 words
The compound as defined in claim 69, where R is ##STR85## which is 11-{1-[3-(4-fluorophenyl)-propan-3-one]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzxazepine.
Claim 80
Dependent Claim
11 words
The compound as defined in claim 14, where R is ##STR86##
Claim 81
Dependent Claim
14 words
The compound as defined in claim 79, where R is ##STR87## which is 11-[1-(3,4-dichlorobenzoyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine.
Claim 82
Dependent Claim
15 words
The compound as defined in claim 1, where m is 1 and n is 0.
Claim 83
Dependent Claim
11 words
The compound as defined in claim 81, where Y is hydrogen.
Claim 84
Dependent Claim
11 words
The compound as defined in claim 82, where X is hydrogen.
Claim 85
Dependent Claim
15 words
The compound as defined in claim 1, where m is 2 and n is 0.
Claim 86
Dependent Claim
94 words
A compound of the formula ##STR88## where m and n are each independently 0, 1 or 2 and m+n is 1 or 2, X and Y are each independently hydrogen, loweralkyl or halogen, and R"'CO-- is such that if it is reduced to R"'CH 2 --, the latter is an unsubstituted loweralkyl, or substituted loweralkyl having one to three substituents each of which being independently cyano, hydroxy, cyclohexyl, furyl, thienyl, ##STR89## k being 1, 2 or 3 and W being each independently hydrogen, halogen, hydroxy, loweralkyl, trifluoromethyl, loweralkoxy, nitro, amino, diloweralkylamino, phenoxy, or benzyloxy.
Claim 87
Dependent Claim
94 words
A compound of the formula ##STR88## where m and n are each independently 0, 1 or 2 and m+n is 1 or 2, X and Y are each independently hydrogen, loweralkyl or halogen, and R"'CO-- is such that if it is reduced to R"'CH 2 --, the latter is an unsubstituted loweralkyl, or substituted loweralkyl having one to three substituents each of which being independently cyano, hydroxy, cyclohexyl, furyl, thienyl, ##STR89## k being 1, 2 or 3 and W being each independently hydrogen, halogen, hydroxy, loweralkyl, trifluoromethyl, loweralkoxy, nitro, amino, diloweralkylamino, phenoxy, or benzyloxy.
Claim 88
Dependent Claim
15 words
The compound as defined in claim 85 where m is 1 and n is 1.
Claim 89
Dependent Claim
11 words
The compound as defined in claim 86, where Y is methyl.
Claim 90
Dependent Claim
11 words
The compound as defined in claim 87, where X is hydrogen.
Claim 91
Dependent Claim
11 words
The compound as defined in claim 86, where Y is hydrogen.
Claim 92
Dependent Claim
11 words
The compound as defined in claim 89, where X is chlorine.
Claim 93
Dependent Claim
11 words
The compound as defined in claim 89, where X is hydrogen.
Claim 94
Dependent Claim
110 words
An analgesic or anti-psychotic composition comprising an effective amount of a compound of the formula ##STR90## where m and n are each independently 0, 1 or 2 and m+n is 1 or 2, X and Y are each independently hydrogen, loweralkyl or halogen, and R is hydrogen, cyano, --C(NH 2 )NOH, ##STR91## unsubstituted loweralkyl, or substituted loweralkyl having one to three substituents each of which being independently cyano, hydroxy, cyclohexyl, furyl, thienyl, ##STR92## k being 1, 2 or 3, W being each independently hydrogen, halogen, hydroxy, loweralkyl, trifluoromethyl, loweralkoxy, nitro, amino, diloweralkylamino, phenoxy, or benzyloxy, and Z being hydrogen, loweralkyl or halogen, or a pharmaceutically acceptable acid addition salt thereof.
Claim 95
Dependent Claim
110 words
An analgesic or anti-psychotic composition comprising an effective amount of a compound of the formula ##STR90## where m and n are each independently 0, 1 or 2 and m+n is 1 or 2, X and Y are each independently hydrogen, loweralkyl or halogen, and R is hydrogen, cyano, --C(NH 2 )NOH, ##STR91## unsubstituted loweralkyl, or substituted loweralkyl having one to three substituents each of which being independently cyano, hydroxy, cyclohexyl, furyl, thienyl, ##STR92## k being 1, 2 or 3, W being each independently hydrogen, halogen, hydroxy, loweralkyl, trifluoromethyl, loweralkoxy, nitro, amino, diloweralkylamino, phenoxy, or benzyloxy, and Z being hydrogen, loweralkyl or halogen, or a pharmaceutically acceptable acid addition salt thereof.
Claim 96
Dependent Claim
18 words
The analgesic or anti-psychotic composition as defined in claim 92, where m is 1 and n is 1.
Claim 97
Dependent Claim
14 words
The analgesic or anti-psychotic composition as defined in claim 93, where Y is methyl.
Claim 98
Dependent Claim
14 words
The analgesic or anti-psychotic composition as defined in claim 94, where X is hydrogen.
Claim 99
Dependent Claim
13 words
The analgesic anti-psychotic composition as defined in claim 93, where Y is hydrogen.
Claim 100
Dependent Claim
14 words
The analgesic or anti-psychotic composition as defined in claim 96, where X is chlorine.
Claim 101
Dependent Claim
14 words
The analgesic or anti-psychotic composition as defined in claim 96, where X is hydrogen.
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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) | 1989-08-25 | 1990-02-24 | 1990-08-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-25 | 1994-02-24 | 1994-08-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-25 | 1998-02-24 | 1998-08-26 | $7700.00 | Window Closed / Lapsed |