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US4008250A Expired / Lapsed US ⏱️ 0.0 years remaining

Cyclopenta[c]pyrrole derivatives

Assignee: STWB Inc
•
Filing: 1975-03-17
•
Granted: 1977-02-15
•
Expires: 1995-03-17
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Abstract

Abstract 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as anti-secretory and anti-ulcer agents are prepared by hydrolysis or thiohydrolysis of the corresponding 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitriles or, in the case of the thiocarboxamides, by reaction of the 4-carboxamide with phosphorus pentasulfide.

Inventors

  • 👤 Malcolm R. Bell
  • 👤 Rudolf Oesterlin

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 00:57
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07C; C07C255/00; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D209/00; C07D209/02; C07D209/52; C07D307/46; C07D487/00; C07D487/02; C07D487/10

Claims Analysis

Total Claims: 40
Claim 1
Independent Claim 128 words
A compound having the formula ##STR28## where each of R 3 , R 4 and R 5 is hydrogen or methyl; each R 6 group is the same or different hydrogen, formyl, and lower-alkane-1,3-diol ketals thereof, phenyl-lower-alkyl, carboxy, carbo-lower-alkoxy, chloromethyl, dichloromethyl, trichloromethyl, hydroxymethyl, hydroxycyanomethyl or lower-alkyl; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, lower-alkylthio-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl, phenyl-lower-alkyl, cyano-lower-alkyl, or divalent-lower-alkylene having its valences on different carbon atoms and joining two of the 2,4,5,6-tetrahydrocyclopenta-[c]pyrrole moieties together, and wherein the phenyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single methylenedioxy or by from one to three members of the group consisting of lower-alkyl, lower-alkoxy, halogen, hydroxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino, carboxyl, carboxamido, carbo-lower-alkoxy, lower-alkylmercapto, lower-alkylsulfinyl, lower-alkylsulfonyl, nitro and sulfamoyl.
Claim 2
Dependent Claim 128 words
A compound having the formula ##STR28## where each of R 3 , R 4 and R 5 is hydrogen or methyl; each R 6 group is the same or different hydrogen, formyl, and lower-alkane-1,3-diol ketals thereof, phenyl-lower-alkyl, carboxy, carbo-lower-alkoxy, chloromethyl, dichloromethyl, trichloromethyl, hydroxymethyl, hydroxycyanomethyl or lower-alkyl; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, lower-alkylthio-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl, phenyl-lower-alkyl, cyano-lower-alkyl, or divalent-lower-alkylene having its valences on different carbon atoms and joining two of the 2,4,5,6-tetrahydrocyclopenta-[c]pyrrole moieties together, and wherein the phenyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single methylenedioxy or by from one to three members of the group consisting of lower-alkyl, lower-alkoxy, halogen, hydroxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino, carboxyl, carboxamido, carbo-lower-alkoxy, lower-alkylmercapto, lower-alkylsulfinyl, lower-alkylsulfonyl, nitro and sulfamoyl.
Claim 3
Dependent Claim 120 words
A compound having the formula ##STR29## where each of R 3 , R 4 and R 5 is hydrogen or methyl; each R 6 group is the same or different hydrogen, formyl, and lower-alkane-1,3-diol ketals thereof, hydroxymethyl, carboxy, carbo-lower-alkoxy, chloromethyl, dichloromethyl, trichloromethyl, hydroxycyanomethyl or lower-alkyl; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl, phenyl-lower-alkyl, cyano-lower-alkyl, or divalent-lower-alkylene having its valences on different carbon atoms and joining two of the 2,4,5,6-tetrahydrocyclopenta[c]pyrrole moieties together, and wherein the phenyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single methylenedioxy or by from one to three members of the group consisting of lower-alkyl, lower-alkoxy, halogen, hydroxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino, nitro and sulfamoyl.
Claim 4
Dependent Claim 120 words
A compound having the formula ##STR29## where each of R 3 , R 4 and R 5 is hydrogen or methyl; each R 6 group is the same or different hydrogen, formyl, and lower-alkane-1,3-diol ketals thereof, hydroxymethyl, carboxy, carbo-lower-alkoxy, chloromethyl, dichloromethyl, trichloromethyl, hydroxycyanomethyl or lower-alkyl; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl, phenyl-lower-alkyl, cyano-lower-alkyl, or divalent-lower-alkylene having its valences on different carbon atoms and joining two of the 2,4,5,6-tetrahydrocyclopenta[c]pyrrole moieties together, and wherein the phenyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single methylenedioxy or by from one to three members of the group consisting of lower-alkyl, lower-alkoxy, halogen, hydroxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino, nitro and sulfamoyl.
Claim 5
Dependent Claim 57 words
A compound according to claim 2 having the formula ##STR30## where each of R 3 , R 4 and R 5 is hydrogen or methyl; both R 6 groups are simultaneously lower-alkyl; and R 7 is hydrogen, lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, or divalent-lower-alkylene having its valences on different carbon atoms and joining two of the 2,4,5,6-tetrahydrocyclopenta[c]pyrrole moieties together.
Claim 6
Dependent Claim 74 words
A compound according to claim 2 having the formula ##STR31## where each of R 3 , R 4 and R 5 is hydrogen or methyl; both R 6 groups are simultaneously lower-alkyl; and R 7 is phenyl, or phenyl-lower-alkyl, and wherein the phenyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single member of the group consisting of lower-alkyl, lower-alkoxy, halogen, hydroxy, methylenedioxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino and sulfamoyl.
Claim 7
Dependent Claim 40 words
A compound according to claim 2 having the formula ##STR32## where each of R 3 , R 4 and R 5 is hydrogen or methyl; both R 6 groups are simultaneously lower-alkyl; and R 7 is lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl or cyano-lower-alkyl.
Claim 8
Dependent Claim 67 words
A compound according to claim 2 having the formula ##STR33## where each of R 3 , R 4 and R 5 is hydrogen or methyl; both R 6 groups are simultaneously hydrogen, formyl, dichloromethyl, or lower-alkyl; and R 7 is phenyl or phenyl-substituted in the phenyl nucleus by a single member of the group consisting of lower-alkyl, lower-alkoxy, halogen, hydroxy, methylenedioxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino and sulfamoyl.
Claim 9
Dependent Claim 5 words
2,4,5,6-Tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 10
Dependent Claim 5 words
2,4,5,6-Tetrahydro-1,2,3,4,6,6-hexamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 11
Dependent Claim 5 words
2-Ethyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 12
Dependent Claim 5 words
2-Propyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 13
Dependent Claim 5 words
2-Butyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 14
Dependent Claim 5 words
2-Isopropyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 15
Dependent Claim 5 words
2-Cyclohexyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 16
Dependent Claim 5 words
2-Cyclopropyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 17
Dependent Claim 5 words
2-Cyclopentyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 18
Dependent Claim 5 words
2-Cyclobutyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 3.
Claim 19
Dependent Claim 4 words
2,2'-Hexamethylenebis[2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile]according to claim 3.
Claim 20
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 21
Dependent Claim 5 words
2-(4-Methoxyphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 22
Dependent Claim 5 words
2-(4-Methylphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 23
Dependent Claim 5 words
2-(4-Chlorophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 24
Dependent Claim 5 words
2-(3-Chlorophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 25
Dependent Claim 5 words
2-(3-Methylphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 26
Dependent Claim 5 words
2-(2-Chlorophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 27
Dependent Claim 5 words
2-(2-Methylphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 28
Dependent Claim 5 words
2-(4-Fluorophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 29
Dependent Claim 5 words
2-(4-Dimethylaminophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 30
Dependent Claim 5 words
2-(4-Hydroxyphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 31
Dependent Claim 5 words
2-(4-Acetylaminophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 32
Dependent Claim 5 words
2-(4-Sulfamylphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 33
Dependent Claim 5 words
2-(2-Phenethyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 34
Dependent Claim 5 words
2-Benzyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 4.
Claim 35
Dependent Claim 5 words
2-(2-Cyanoethyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 5.
Claim 36
Dependent Claim 5 words
2-(2-Ethoxyethyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 5.
Claim 37
Dependent Claim 5 words
2-(3-Hydroxypropyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 5.
Claim 38
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1,3-diformyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 6.
Claim 39
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1,3-bis-dichloromethyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 6.
Claim 40
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-4,6,6-trimethylcyclopenta[c]pyrrole-4-carbonitrile according to claim 6.

References Cited (Backward Citations)

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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) 1980-02-15 1980-08-16 1981-02-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-02-15 1984-08-16 1985-02-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-02-15 1988-08-16 1989-02-15 $7700.00 Window Closed / Lapsed

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