← Back to Patent Explorer
US4126620A Expired / Lapsed US ⏱️ 0.0 years remaining

Cyclopenta (c) pyrrole derivatives

Assignee: Sanofi SA
•
Filing: 1977-02-25
•
Granted: 1978-11-21
•
Expires: 1997-02-25
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as antisecretory 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 2026-11-05 22:37
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D209/00; C07D209/02; C07D209/52; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D307/46; C07D487/00; C07D487/02; C07D487/10; C07D491/00; C07D491/02; C07D491/04

Claims Analysis

Total Claims: 62
Claim 1
Independent Claim 324 words
A compound having the formula: ##STR13## where X is O or S; R 1 is hydrogen, lower-alkyl or di-lower-alkylamino-lower-alkyl; R 2 is hydrogen or lower-alkyl; 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, carbo-lower-alkoxy-lower-alkyl, carbo-lower-alkoxy-lower alkenyl, carboxy-lower-alkyl, carboxy-lower-alkenyl, methyl, lower-alkenyl or a group of the formula: ##STR14## where R 8 is hydrogen, lower-alkyl, lower-alkenyl, lower-alkynyl, phenyl or phenyl-lower-alkyl; R 9 is hydrogen, cyano, lower-alkyl, lower-alkenyl, lower-alkynyl, phenyl, phenyl-lower-alkyl, carboxy, carbo-lower-alkoxy, carbamyl, aminomethyl, lower-alkanoyl, trichloromethyl, carbo-lower-alkoxy-lower-alkyl or carbo-lower-alkoxy-lower-alkynyl; R 10 is hydrogen, benzoyl, lower-alkanoyl, carboxy-lower-alkanoyl and ammonium salts thereof, or lower-alkyl, R 10 being other than hydrogen only when either one or both of R 8 and R 9 are hydrogen and R 9 being cyano only when R 10 is hydrogen; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, lower-alkynyl, di-lower-alkylamino-lower-alkyl, carbo-lower-alkoxy-lower-alkyl, carboxy-lower-alkyl, carboxamido-lower-alkyl, thiocarboxamido-lower-alkyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, lower-alkythio-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl, phenyl-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, benzoyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single methylene-dioxy or lower-alkoxy group or by from one to three, the same or different, members of the group consisting of lower-alkyl, halogen, hydroxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino, di-lower-alkylaminomethyl, carboxy, carboxamido, carbo-lower-alkoxy, lower-alkylmercapto, lower-alkylsulfinyl, lower-alkylsulfonyl, nitro and sulfamoyl, and wherein lower-alkyl and lower-alkoxy, each occurrence, contains from one to four carbon atoms; lower-alkane, lower-alkenyl and lower-alkynyl, each occurrence, contain from three to six carbon atoms; lower-alkanoyl, each occurrence, contains from two to five carbon atoms, and lower-alkylene, each occurrence, contains from one to eight carbon atoms, except that both R 6 groups are not simultaneously hydrogen and further except that when R 7 is unsubstituted phenyl and R 6 at the 3-position and R 8 are both hydrogen, R 9 is not unsubstituted-phenyl.
Claim 2
Dependent Claim 324 words
A compound having the formula: ##STR13## where X is O or S; R 1 is hydrogen, lower-alkyl or di-lower-alkylamino-lower-alkyl; R 2 is hydrogen or lower-alkyl; 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, carbo-lower-alkoxy-lower-alkyl, carbo-lower-alkoxy-lower alkenyl, carboxy-lower-alkyl, carboxy-lower-alkenyl, methyl, lower-alkenyl or a group of the formula: ##STR14## where R 8 is hydrogen, lower-alkyl, lower-alkenyl, lower-alkynyl, phenyl or phenyl-lower-alkyl; R 9 is hydrogen, cyano, lower-alkyl, lower-alkenyl, lower-alkynyl, phenyl, phenyl-lower-alkyl, carboxy, carbo-lower-alkoxy, carbamyl, aminomethyl, lower-alkanoyl, trichloromethyl, carbo-lower-alkoxy-lower-alkyl or carbo-lower-alkoxy-lower-alkynyl; R 10 is hydrogen, benzoyl, lower-alkanoyl, carboxy-lower-alkanoyl and ammonium salts thereof, or lower-alkyl, R 10 being other than hydrogen only when either one or both of R 8 and R 9 are hydrogen and R 9 being cyano only when R 10 is hydrogen; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, lower-alkynyl, di-lower-alkylamino-lower-alkyl, carbo-lower-alkoxy-lower-alkyl, carboxy-lower-alkyl, carboxamido-lower-alkyl, thiocarboxamido-lower-alkyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, lower-alkythio-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl, phenyl-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, benzoyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single methylene-dioxy or lower-alkoxy group or by from one to three, the same or different, members of the group consisting of lower-alkyl, halogen, hydroxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino, di-lower-alkylaminomethyl, carboxy, carboxamido, carbo-lower-alkoxy, lower-alkylmercapto, lower-alkylsulfinyl, lower-alkylsulfonyl, nitro and sulfamoyl, and wherein lower-alkyl and lower-alkoxy, each occurrence, contains from one to four carbon atoms; lower-alkane, lower-alkenyl and lower-alkynyl, each occurrence, contain from three to six carbon atoms; lower-alkanoyl, each occurrence, contains from two to five carbon atoms, and lower-alkylene, each occurrence, contains from one to eight carbon atoms, except that both R 6 groups are not simultaneously hydrogen and further except that when R 7 is unsubstituted phenyl and R 6 at the 3-position and R 8 are both hydrogen, R 9 is not unsubstituted-phenyl.
Claim 3
Dependent Claim 277 words
A compound having the formula: ##STR15## where R 1 is hydrogen, lower-alkyl or di-lower-alkylamino-lower-alkyl; R 2 is hydrogen or lower-alkyl; each R 6 group is the same or different hydrogen, formyl, and lower-alkane-1,3-diol ketals thereof, carboxy, carbo-lower-alkoxy, carbo-lower-alkoxy-lower-alkyl, carbo-lower-alkoxy-lower-alkenyl, carboxy-lower-alkyl, carboxy-lower-alkenyl, methyl, lower-alkenyl, or a group of the formula ##STR16## where R 8 is hydrogen, lower-alkyl, lower-alkenyl, lower-alkynyl or phenyl; R 9 is hydrogen, cyano, lower-alkyl, carbamyl, carbo-lower-alkoxy-alkynyl; R 10 is hydrogen, benzoyl, lower-alkanoyl, carbo-lower-alkoxy-lower-alkyl, carboxy-lower-alkanoyl and ammonium salts thereof, or lower-alkyl, R 10 being other than hydrogen only when either or both of R 8 and R 9 are hydrogen and R 9 being cyano only when R 10 is hydrogen; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, lower-alkynyl, di-lower-alkylamino-lower-alkyl, carbo-lower-alkoxy-lower-alkyl, carboxamido-lower-alkyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl, phenyl-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, benzoyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single lower-alkoxy group or by from one to two members of the group consisting of lower-alkyl, halogen, hydroxy, methylenedioxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino, di-lower-alkylaminomethyl, carboxy, carbo-lower-alkoxy and sulfamoyl, and wherein lower-alkyl and lower-alkoxy, each occurrence, contain from one to four carbon atoms; lower-alkane, lower-alkenyl and lower-alkynyl, each occurrence, contain from three to six carbon atoms; lower-alkanoyl, each occurrence, contains from two to five carbon atoms; and lower-alkylene, each occurrence, contains from one to eight carbon atoms, except that both R 6 groups are not simultaneously hydrogen and further except that when R 7 is unsubstituted-phenyl and R 6 at the 3-position and R 8 are both hydrogen, R 9 is not unsubstituted-phenyl.
Claim 4
Dependent Claim 277 words
A compound having the formula: ##STR15## where R 1 is hydrogen, lower-alkyl or di-lower-alkylamino-lower-alkyl; R 2 is hydrogen or lower-alkyl; each R 6 group is the same or different hydrogen, formyl, and lower-alkane-1,3-diol ketals thereof, carboxy, carbo-lower-alkoxy, carbo-lower-alkoxy-lower-alkyl, carbo-lower-alkoxy-lower-alkenyl, carboxy-lower-alkyl, carboxy-lower-alkenyl, methyl, lower-alkenyl, or a group of the formula ##STR16## where R 8 is hydrogen, lower-alkyl, lower-alkenyl, lower-alkynyl or phenyl; R 9 is hydrogen, cyano, lower-alkyl, carbamyl, carbo-lower-alkoxy-alkynyl; R 10 is hydrogen, benzoyl, lower-alkanoyl, carbo-lower-alkoxy-lower-alkyl, carboxy-lower-alkanoyl and ammonium salts thereof, or lower-alkyl, R 10 being other than hydrogen only when either or both of R 8 and R 9 are hydrogen and R 9 being cyano only when R 10 is hydrogen; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, lower-alkynyl, di-lower-alkylamino-lower-alkyl, carbo-lower-alkoxy-lower-alkyl, carboxamido-lower-alkyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl, phenyl-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, benzoyl or phenyl-lower-alkyl groups can be further substituted in the phenyl nucleus by a single lower-alkoxy group or by from one to two members of the group consisting of lower-alkyl, halogen, hydroxy, methylenedioxy, trifluoromethyl, lower-alkanoylamino, amino, di-lower-alkylamino, di-lower-alkylaminomethyl, carboxy, carbo-lower-alkoxy and sulfamoyl, and wherein lower-alkyl and lower-alkoxy, each occurrence, contain from one to four carbon atoms; lower-alkane, lower-alkenyl and lower-alkynyl, each occurrence, contain from three to six carbon atoms; lower-alkanoyl, each occurrence, contains from two to five carbon atoms; and lower-alkylene, each occurrence, contains from one to eight carbon atoms, except that both R 6 groups are not simultaneously hydrogen and further except that when R 7 is unsubstituted-phenyl and R 6 at the 3-position and R 8 are both hydrogen, R 9 is not unsubstituted-phenyl.
Claim 5
Dependent Claim 64 words
A compound according to claim 2 where each of R 1 and R 2 is hydrogen; each R 6 group is a different hydrogen or lower-alkyl group or a group of the formula ##STR17## where R 8 is hydrogen, lower-alkyl, lower-alkenyl or lower-alkynyl; R 9 is hydrogen; R 10 is hydrogen or carboxy-lower-alkanoyl and ammonium salts thereof; and R 7 is lower-alkyl or phenyl.
Claim 6
Dependent Claim 60 words
A compound according to claim 3 where the R 6 group at the 1-position is hydrogen, lower-alkyl, or a group of the formula ##STR18## where R 8 is hydrogen, lower-alkyl, lower-alkenyl or lower-alkynyl; R 10 is hydrogen or carboxy-lower-alkanoyl and ammonium salts thereof; the R 6 group at the 3-position is hydrogen, lower-alkyl or hydroxymethyl; and R 7 is phenyl.
Claim 7
Dependent Claim 52 words
A compound according to claim 2 where each of R 1 and R 2 is hydrogen or lower-alkyl; both R 6 groups are simultaneously lower-alkyl; and R 7 is hydrogen, lower-alkyl, halo-lower-alkyl, lower-alkenyl, 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 8
Dependent Claim 67 words
A compound according to claim 2 where each of R 1 and R 2 is hydrogen or lower-alkyl; 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 9
Dependent Claim 35 words
A compound according to claim 2 where each of R 1 and R 2 is hydrogen or lower-alkyl; both R 6 groups are simultaneously lower-alkyl; and R 7 is di-lower-alkylamino-lower-alkyl, carbo-lower-alkoxy-lower-alkyl, carboxamido-lower-alkyl, lower-alkoxy-lower-alkyl or hydroxy-lower-alkyl.
Claim 10
Dependent Claim 58 words
A compound according to claim 2 where each of R 1 and R 2 is hydrogen or lower-alkyl; both R 6 groups are simultaneously formyl or hydroxymethyl; 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 11
Dependent Claim 16 words
A compound according to claim 5 where each of R 1 and R 2 is hydrogen.
Claim 12
Dependent Claim 16 words
A compound according to claim 6 where each of R 1 and R 2 is hydrogen.
Claim 13
Dependent Claim 16 words
A compound according to claim 7 where each of R 1 and R 2 is hydrogen.
Claim 14
Dependent Claim 16 words
A compound according to claim 8 where each of R 1 and R 2 is hydrogen.
Claim 15
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1-hydroxymethyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide according to claim 4.
Claim 16
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1-hydroxymethyl-3,4,6,6-tetramethylcyclopenta[c]pyrrole-4-carboxamide according to claim 4.
Claim 17
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-3-hydroxymethyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide according to claim 4.
Claim 18
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-3-hydroxymethyl-1,4,6,6-tetramethylcyclopenta[c]pyrrole-4-carboxamide according to claim 4.
Claim 19
Dependent Claim 5 words
2-Phenyl-1-(1-hydroxymethyl)-2,4,5,6-tetrahydro-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide according to claim 4.
Claim 20
Dependent Claim 5 words
2-Phenyl-1-(1-hydroxy-2-propenyl)-2,4,5,6-tetrahydro-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide according to claim 4.
Claim 21
Dependent Claim 5 words
2-Phenyl-1-(1-hydroxypentyl)-2,4,5,6-tetrahydro-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide according to claim 4.
Claim 22
Dependent Claim 5 words
2-Phenyl-1-(1-hydroxypropyl)-2,4,5,6-tetrahydro-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide according to claim 4.
Claim 23
Dependent Claim 8 words
2-Phenyl-2,4,5,6-tetrahydro-1-hydroxymethyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide butanedioate half ester according to claim 4.
Claim 24
Dependent Claim 9 words
Ammonium 2-phenyl-2,4,5,6-tetrahydro-1-hydroxymethyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide butanedioate half ester according to claim 4.
Claim 25
Dependent Claim 5 words
2,4,5,6-Tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 26
Dependent Claim 5 words
2,4,5,6-Tetrahydro-1,2,3,4,6,6-hexamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 27
Dependent Claim 5 words
2-Ethyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 28
Dependent Claim 5 words
2-Propyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 29
Dependent Claim 5 words
2-Butyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 30
Dependent Claim 5 words
2-Isopropyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 31
Dependent Claim 5 words
2-Allyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 32
Dependent Claim 5 words
2-Cyclohexyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 33
Dependent Claim 5 words
2-Cyclopropyl-2,4,5,6-tetahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 34
Dependent Claim 5 words
2-Cyclopentyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 35
Dependent Claim 5 words
2-Cyclobutyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 36
Dependent Claim 5 words
2-Cyclopropylmethyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 37
Dependent Claim 5 words
2,2'-Hexamethylenebis[2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide] according to claim 9.
Claim 38
Dependent Claim 5 words
2-(2-Fluroroethyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 9.
Claim 39
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-N,N-dimethylcarboxamide according to claim 6.
Claim 40
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 41
Dependent Claim 5 words
2-(4-Methoxyphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 42
Dependent Claim 5 words
2-(4-Methylphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 43
Dependent Claim 5 words
2-(4-Chlorophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 44
Dependent Claim 5 words
2-(3-Chlorophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 45
Dependent Claim 5 words
2-(3-Methylphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 46
Dependent Claim 5 words
2-(2-Chlorophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 47
Dependent Claim 5 words
2-(2-Methylphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 48
Dependent Claim 5 words
2-(4-Fluorophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 49
Dependent Claim 5 words
2-(4-Hydroxyphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 50
Dependent Claim 5 words
2-(4-Acetylaminophenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 51
Dependent Claim 5 words
2-(4-Dimethylaminophenyl)-2,4,5,6-tetrahydro1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 52
Dependent Claim 5 words
2-(4-Sulfamylphenyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 53
Dependent Claim 5 words
2-(2-Phenethyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 54
Dependent Claim 5 words
2-Benzyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 10.
Claim 55
Dependent Claim 5 words
2-[3-(Dimethylamino)propyl]-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 11.
Claim 56
Dependent Claim 5 words
2-(2-Dimethylaminoethyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 11.
Claim 57
Dependent Claim 6 words
Ethyl 4-carbamoyl-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-2-acetate according to claim 11.
Claim 58
Dependent Claim 5 words
2-(2-Carboxamidoethyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 11.
Claim 59
Dependent Claim 5 words
2-(2-Ethoxyethyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 11.
Claim 60
Dependent Claim 5 words
2-(3-Hydroxypropyl)-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carboxamide according to claim 11.
Claim 61
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1,3-diformyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide according to claim 12.
Claim 62
Dependent Claim 5 words
2-Phenyl-2,4,5,6-tetrahydro-1,3-bis-hydroxymethyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carboxamide according to claim 12.

References Cited (Backward Citations)

US3696117A Cited
US3928380A Cited
US4008250A Cited
US3972994A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-11-20 1982-05-22 1982-11-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-11-20 1986-05-22 1986-11-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-11-20 1990-05-22 1990-11-21 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag