GB1202747A - 0,3-disubstituted pyrrolidines - Google Patents
0,3-disubstituted pyrrolidinesInfo
- Publication number
- GB1202747A GB1202747A GB50259/67A GB5025967A GB1202747A GB 1202747 A GB1202747 A GB 1202747A GB 50259/67 A GB50259/67 A GB 50259/67A GB 5025967 A GB5025967 A GB 5025967A GB 1202747 A GB1202747 A GB 1202747A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- pyrrolidinyl
- pyrrolidine
- phenyl
- benzoxazepine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003235 pyrrolidines Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- -1 CF 3 Chemical group 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- LHITVXRBQDLEJF-JAMMHHFISA-N (3S)-3-amino-4-anilinopyrrolidine-2,5-dione Chemical compound N(C1=CC=CC=C1)C1[C@H](N)C(=O)NC1=O LHITVXRBQDLEJF-JAMMHHFISA-N 0.000 abstract 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- BVAWVWGNGDHBJO-UHFFFAOYSA-N 1-(1-benzyl-4-methylpyrrolidin-3-yl)-1-phenylpropan-1-ol Chemical compound C(C1=CC=CC=C1)N1CC(C(C1)C)C(O)(C1=CC=CC=C1)CC BVAWVWGNGDHBJO-UHFFFAOYSA-N 0.000 abstract 1
- ZLOBNKYLUQPGEZ-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-3-yl)-1-[4-(trifluoromethyl)phenyl]ethanol Chemical compound C(C1=CC=CC=C1)N1CC(CC1)C(O)(C1=CC=C(C=C1)C(F)(F)F)C ZLOBNKYLUQPGEZ-UHFFFAOYSA-N 0.000 abstract 1
- QOWMIVXPJYFLMQ-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-3-yl)-1-phenylpropan-1-ol Chemical compound C(C1=CC=CC=C1)N1CC(CC1)C(O)(C1=CC=CC=C1)CC QOWMIVXPJYFLMQ-UHFFFAOYSA-N 0.000 abstract 1
- DUWPTTFXFPHJQZ-UHFFFAOYSA-N 1-(2-methylphenyl)pyrrolidin-3-ol Chemical compound CC1=CC=CC=C1N1CC(O)CC1 DUWPTTFXFPHJQZ-UHFFFAOYSA-N 0.000 abstract 1
- KAGUYPQFCBPBBF-UHFFFAOYSA-N 1-benzyl-3-(2-methoxyphenoxy)pyrrolidine Chemical compound COC1=CC=CC=C1OC1CN(CC=2C=CC=CC=2)CC1 KAGUYPQFCBPBBF-UHFFFAOYSA-N 0.000 abstract 1
- PVGKRIVTZOPYDN-UHFFFAOYSA-N 1-benzyl-3-(2-methylphenyl)pyrrolidin-3-ol Chemical compound CC1=CC=CC=C1C1(O)CN(CC=2C=CC=CC=2)CC1 PVGKRIVTZOPYDN-UHFFFAOYSA-N 0.000 abstract 1
- PBEAYUMWBYJURU-UHFFFAOYSA-N 1-benzyl-3-[3-(trifluoromethyl)phenoxy]pyrrolidine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(OC2CN(CC=3C=CC=CC=3)CC2)=C1 PBEAYUMWBYJURU-UHFFFAOYSA-N 0.000 abstract 1
- YMTSOJGEQVRFFT-UHFFFAOYSA-N 1-benzyl-3-[4-(diethylamino)phenyl]pyrrolidin-3-ol Chemical compound C(C1=CC=CC=C1)N1CC(CC1)(O)C1=CC=C(C=C1)N(CC)CC YMTSOJGEQVRFFT-UHFFFAOYSA-N 0.000 abstract 1
- SSVQHINBCDDYNL-WLHGVMLRSA-N 1-benzyl-3-phenoxypyrrolidine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=CC=1CN(C1)CCC1OC1=CC=CC=C1 SSVQHINBCDDYNL-WLHGVMLRSA-N 0.000 abstract 1
- SKCZWPHHDTZNIV-UHFFFAOYSA-N 1-chloro-3-[3-(trifluoromethyl)phenyl]pyrrolidine Chemical compound FC(C=1C=C(C=CC1)C1CN(CC1)Cl)(F)F SKCZWPHHDTZNIV-UHFFFAOYSA-N 0.000 abstract 1
- LYJSURCAUBFCEY-UHFFFAOYSA-N 1-phenyl-1-pyrrolidin-3-ylethanol Chemical compound CC(O)(C1CNCC1)C1=CC=CC=C1 LYJSURCAUBFCEY-UHFFFAOYSA-N 0.000 abstract 1
- DIAVOCCGZXPLMO-UHFFFAOYSA-N 1-phenyl-1-pyrrolidin-3-ylpropan-1-ol Chemical compound C(C)C(O)(C1CNCC1)C1=CC=CC=C1 DIAVOCCGZXPLMO-UHFFFAOYSA-N 0.000 abstract 1
- OYAUROXDKWTXHV-UHFFFAOYSA-N 1-phenyl-2-pyrrolidin-3-ylbutan-2-ol Chemical compound C(C1=CC=CC=C1)C(O)(C1CNCC1)CC OYAUROXDKWTXHV-UHFFFAOYSA-N 0.000 abstract 1
- RMYZWQSQMIXWEN-UHFFFAOYSA-N 1-pyrrolidin-3-yl-1-[4-(trifluoromethyl)phenyl]ethanol Chemical compound CC(O)(C1CNCC1)C1=CC=C(C=C1)C(F)(F)F RMYZWQSQMIXWEN-UHFFFAOYSA-N 0.000 abstract 1
- OWVPCUZYAAYLLV-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1,4-benzoxazepine;hydrochloride Chemical compound Cl.C1NCCOC2=CC=CC=C21 OWVPCUZYAAYLLV-UHFFFAOYSA-N 0.000 abstract 1
- JWSLRPIYZOXPSF-UHFFFAOYSA-N 2-(1-benzylpyrrolidin-3-yl)-1,3-dihydroisoindole dihydrochloride Chemical compound Cl.Cl.C(C1=CC=CC=C1)N1CC(CC1)N1CC2=CC=CC=C2C1 JWSLRPIYZOXPSF-UHFFFAOYSA-N 0.000 abstract 1
- ZILCRMAYDFNREU-UHFFFAOYSA-N 2-(1-benzylpyrrolidin-3-yl)-1h-benzimidazole Chemical compound C1CC(C=2NC3=CC=CC=C3N=2)CN1CC1=CC=CC=C1 ZILCRMAYDFNREU-UHFFFAOYSA-N 0.000 abstract 1
- VZUGAFLCEUCRRS-UHFFFAOYSA-N 2-(1-benzylpyrrolidin-3-yl)-4,5-dimethoxy-1,3-dihydroisoindole Chemical compound COC1=C2CN(CC2=CC=C1OC)C1CN(CC1)CC1=CC=CC=C1 VZUGAFLCEUCRRS-UHFFFAOYSA-N 0.000 abstract 1
- NBLDRRTUBLYRMY-UHFFFAOYSA-N 2-(1-benzylpyrrolidin-3-yl)-4-(trifluoromethyl)-1,3-dihydroisoindole Chemical compound FC(C1=C2CN(CC2=CC=C1)C1CN(CC1)CC1=CC=CC=C1)(F)F NBLDRRTUBLYRMY-UHFFFAOYSA-N 0.000 abstract 1
- AYLGSTZFRLAEGQ-UHFFFAOYSA-N 2-(1-benzylpyrrolidin-3-yl)-5,6-dimethoxyisoindole-1,3-dione Chemical compound COC=1C=C2C(C(=O)N(C2=O)C2CN(CC2)CC2=CC=CC=C2)=CC1OC AYLGSTZFRLAEGQ-UHFFFAOYSA-N 0.000 abstract 1
- DLEHBGFKTMKLGO-UHFFFAOYSA-N 2-(1-benzylpyrrolidin-3-yl)-5-(trifluoromethyl)isoindole-1,3-dione Chemical compound FC(C=1C=C2C(C(=O)N(C2=O)C2CN(CC2)CC2=CC=CC=C2)=CC1)(F)F DLEHBGFKTMKLGO-UHFFFAOYSA-N 0.000 abstract 1
- NMGHGRJGKQIDEY-UHFFFAOYSA-N 2-(1-benzylpyrrolidin-3-yl)-5-methylisoindole-1,3-dione Chemical compound CC=1C=C2C(C(=O)N(C2=O)C2CN(CC2)CC2=CC=CC=C2)=CC1 NMGHGRJGKQIDEY-UHFFFAOYSA-N 0.000 abstract 1
- LBPDTAFHCUGAQN-UHFFFAOYSA-N 2-(1-benzylpyrrolidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C1)CCN1CC1=CC=CC=C1 LBPDTAFHCUGAQN-UHFFFAOYSA-N 0.000 abstract 1
- WEIAIYZTCNPZJN-UHFFFAOYSA-N 2-[[(1-benzylpyrrolidin-3-yl)amino]methyl]-5-(diethylamino)phenol Chemical compound C(C1=CC=CC=C1)N1CC(CC1)NCC1=C(C=C(C=C1)N(CC)CC)O WEIAIYZTCNPZJN-UHFFFAOYSA-N 0.000 abstract 1
- QEYSFAWRXLKKCV-UHFFFAOYSA-N 2-[[(1-benzylpyrrolidin-3-yl)amino]methyl]-6-methoxyphenol Chemical compound C(C1=CC=CC=C1)N1CC(CC1)NCC1=C(C(=CC=C1)OC)O QEYSFAWRXLKKCV-UHFFFAOYSA-N 0.000 abstract 1
- IOBUCSZFTJFULZ-UHFFFAOYSA-N 2-[[(1-benzylpyrrolidin-3-yl)amino]methyl]phenol hydrochloride Chemical compound Cl.C(C1=CC=CC=C1)N1CC(CC1)NCC1=C(C=CC=C1)O IOBUCSZFTJFULZ-UHFFFAOYSA-N 0.000 abstract 1
- SXRYRTQBFDKDBD-UHFFFAOYSA-N 2-pyrrolidin-3-yl-1H-benzimidazole dihydrochloride Chemical compound Cl.Cl.N1CC(CC1)C=1NC2=C(N1)C=CC=C2 SXRYRTQBFDKDBD-UHFFFAOYSA-N 0.000 abstract 1
- ORTGDZQMCONZCG-UHFFFAOYSA-N 2-pyrrolidin-3-yl-4-(trifluoromethyl)-1,3-dihydroisoindole Chemical compound N1CC(CC1)N1CC2=CC=CC(=C2C1)C(F)(F)F ORTGDZQMCONZCG-UHFFFAOYSA-N 0.000 abstract 1
- NUPVGPCMRJIIPJ-UHFFFAOYSA-N 3-(2-bromophenoxy)pyrrolidine Chemical compound BrC1=CC=CC=C1OC1CNCC1 NUPVGPCMRJIIPJ-UHFFFAOYSA-N 0.000 abstract 1
- XPZIJQMOVSHKOL-UHFFFAOYSA-N 3-(2-methylphenyl)pyrrolidine Chemical compound CC1=CC=CC=C1C1CNCC1 XPZIJQMOVSHKOL-UHFFFAOYSA-N 0.000 abstract 1
- YVMMOOGWEOMGPN-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenoxy]pyrrolidine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(OC2CNCC2)=C1 YVMMOOGWEOMGPN-UHFFFAOYSA-N 0.000 abstract 1
- FEZHIKGQODPJMI-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]pyrrolidin-3-ol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(O)CCNC1 FEZHIKGQODPJMI-UHFFFAOYSA-N 0.000 abstract 1
- UUTJZCKPWWZRAG-UHFFFAOYSA-N 3-[4-(diethylamino)phenyl]pyrrolidin-3-ol Chemical compound C(C)N(C1=CC=C(C=C1)C1(CNCC1)O)CC UUTJZCKPWWZRAG-UHFFFAOYSA-N 0.000 abstract 1
- NHLZTNBPPGIUMZ-UHFFFAOYSA-N 3-phenoxypyrrolidine;hydrochloride Chemical compound Cl.C1NCCC1OC1=CC=CC=C1 NHLZTNBPPGIUMZ-UHFFFAOYSA-N 0.000 abstract 1
- XHARQIFVCGCMPZ-UHFFFAOYSA-N 4,5-dimethoxy-2-pyrrolidin-3-yl-1,3-dihydroisoindole Chemical compound N1CC(CC1)N1CC2=CC=C(C(=C2C1)OC)OC XHARQIFVCGCMPZ-UHFFFAOYSA-N 0.000 abstract 1
- HQBLOZIFDXWSKK-UHFFFAOYSA-N 4-(1-benzylpyrrolidin-3-yl)-5H-1,4-benzoxazepine Chemical compound C(C1=CC=CC=C1)N1CC(CC1)N1C=COC2=C(C1)C=CC=C2 HQBLOZIFDXWSKK-UHFFFAOYSA-N 0.000 abstract 1
- VEIDFRATXWBVNN-UHFFFAOYSA-N 4-(1-benzylpyrrolidin-3-yl)-9-methoxy-3,5-dihydro-2H-1,4-benzoxazepine Chemical compound C(C1=CC=CC=C1)N1CC(CC1)N1CCOC2=C(C1)C=CC=C2OC VEIDFRATXWBVNN-UHFFFAOYSA-N 0.000 abstract 1
- UUVWRDUWNNKTLD-UHFFFAOYSA-N 4-(1-benzylpyrrolidin-3-yl)-9-methoxy-5H-1,4-benzoxazepine Chemical compound C(C1=CC=CC=C1)N1CC(CC1)N1C=COC2=C(C1)C=CC=C2OC UUVWRDUWNNKTLD-UHFFFAOYSA-N 0.000 abstract 1
- XWVAPDYBLXUOPI-UHFFFAOYSA-N 4-(1-benzylpyrrolidin-3-yl)-N,N-diethyl-3,5-dihydro-2H-1,4-benzoxazepin-8-amine Chemical compound C(C1=CC=CC=C1)N1CC(CC1)N1CCOC2=C(C1)C=CC(=C2)N(CC)CC XWVAPDYBLXUOPI-UHFFFAOYSA-N 0.000 abstract 1
- IHQXRCUWTQSDKJ-UHFFFAOYSA-N 4-(3-hydroxypyrrolidin-1-yl)-1-phenylbutan-1-one Chemical compound C1C(O)CCN1CCCC(=O)C1=CC=CC=C1 IHQXRCUWTQSDKJ-UHFFFAOYSA-N 0.000 abstract 1
- ONFAMZNVSNABFK-UHFFFAOYSA-N 4-benzyl-5H-1,4-benzoxazepine Chemical compound C(C1=CC=CC=C1)N1C=COC2=C(C1)C=CC=C2 ONFAMZNVSNABFK-UHFFFAOYSA-N 0.000 abstract 1
- NNIFECIXEZUSGG-UHFFFAOYSA-N 4-benzyl-N,N-diethyl-5H-1,4-benzoxazepin-8-amine Chemical compound C(C1=CC=CC=C1)N1C=COC2=C(C1)C=CC(=C2)N(CC)CC NNIFECIXEZUSGG-UHFFFAOYSA-N 0.000 abstract 1
- QFNGTIBLZCKGAF-UHFFFAOYSA-N 4-methyl-2-pyrrolidin-3-yl-1,3-dihydroisoindole Chemical compound N1CC(CC1)N1CC2=CC=CC(=C2C1)C QFNGTIBLZCKGAF-UHFFFAOYSA-N 0.000 abstract 1
- HPKMHHKDGJUENI-UHFFFAOYSA-N 4-pyrrolidin-3-yl-5H-1,4-benzoxazepine Chemical compound N1CC(CC1)N1C=COC2=C(C1)C=CC=C2 HPKMHHKDGJUENI-UHFFFAOYSA-N 0.000 abstract 1
- MMGSSGIIFHIFJD-UHFFFAOYSA-N 9-methoxy-2,3,4,5-tetrahydro-1,4-benzoxazepine Chemical compound C1NCCOC2=C1C=CC=C2OC MMGSSGIIFHIFJD-UHFFFAOYSA-N 0.000 abstract 1
- SLUFBCIROQAWCZ-UHFFFAOYSA-N 9-methoxy-4-pyrrolidin-3-yl-3,5-dihydro-2H-1,4-benzoxazepine Chemical compound N1CC(CC1)N1CCOC2=C(C1)C=CC=C2OC SLUFBCIROQAWCZ-UHFFFAOYSA-N 0.000 abstract 1
- FSWGIIUHQCWANT-UHFFFAOYSA-N 9-methoxy-4-pyrrolidin-3-yl-5H-1,4-benzoxazepine Chemical compound N1CC(CC1)N1C=COC2=C(C1)C=CC=C2OC FSWGIIUHQCWANT-UHFFFAOYSA-N 0.000 abstract 1
- ULGDGONGMVYBDY-UHFFFAOYSA-N C(C1=CC=CC=C1)N1C=COC2=C(C1)C=CC=C2OC Chemical compound C(C1=CC=CC=C1)N1C=COC2=C(C1)C=CC=C2OC ULGDGONGMVYBDY-UHFFFAOYSA-N 0.000 abstract 1
- AXIYGCZBYDVXRT-UHFFFAOYSA-N C(C1=CC=CC=C1)N1CC(CC1)C(O)(C1=CC=CC=C1)C Chemical compound C(C1=CC=CC=C1)N1CC(CC1)C(O)(C1=CC=CC=C1)C AXIYGCZBYDVXRT-UHFFFAOYSA-N 0.000 abstract 1
- HIQGNPHOBUXERW-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.C(C1=CC=CC=C1)N1CC(CC1)NC1=C(C=CC=C1)OC Chemical compound C(C=CC(=O)O)(=O)O.C(C1=CC=CC=C1)N1CC(CC1)NC1=C(C=CC=C1)OC HIQGNPHOBUXERW-UHFFFAOYSA-N 0.000 abstract 1
- VYHOBRZCHKIZDV-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.C(C=CC(=O)O)(=O)O.C(C1=CC=CC=C1)N1CC(CC1)N1CCOC2=C(C1)C=CC=C2 Chemical compound C(C=CC(=O)O)(=O)O.C(C=CC(=O)O)(=O)O.C(C1=CC=CC=C1)N1CC(CC1)N1CCOC2=C(C1)C=CC=C2 VYHOBRZCHKIZDV-UHFFFAOYSA-N 0.000 abstract 1
- RJOHOXURLIPYHQ-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.C(C=CC(=O)O)(=O)O.N1CC(CC1)N1CCOC2=C(C1)C=CC=C2 Chemical compound C(C=CC(=O)O)(=O)O.C(C=CC(=O)O)(=O)O.N1CC(CC1)N1CCOC2=C(C1)C=CC=C2 RJOHOXURLIPYHQ-UHFFFAOYSA-N 0.000 abstract 1
- FTBHBDKEYANQSJ-UHFFFAOYSA-N Cl.C(C1=CC=CC=C1)N1CCOC2=C(C1)C=CC=C2 Chemical compound Cl.C(C1=CC=CC=C1)N1CCOC2=C(C1)C=CC=C2 FTBHBDKEYANQSJ-UHFFFAOYSA-N 0.000 abstract 1
- XNAQOQXWGKETPK-UHFFFAOYSA-N Cl.Cl.N1CC(CC1)N1CC2=CC=CC=C2C1 Chemical compound Cl.Cl.N1CC(CC1)N1CC2=CC=CC=C2C1 XNAQOQXWGKETPK-UHFFFAOYSA-N 0.000 abstract 1
- RPFPUWYFKBMCDI-UHFFFAOYSA-N N,N-diethyl-4-pyrrolidin-3-yl-3,5-dihydro-2H-1,4-benzoxazepin-8-amine Chemical compound N1CC(CC1)N1CCOC2=C(C1)C=CC(=C2)N(CC)CC RPFPUWYFKBMCDI-UHFFFAOYSA-N 0.000 abstract 1
- VVCLJPZGFNZOON-UHFFFAOYSA-N N,N-diethyl-4-pyrrolidin-3-yl-5H-1,4-benzoxazepin-8-amine Chemical compound N1CC(CC1)N1C=COC2=C(C1)C=CC(=C2)N(CC)CC VVCLJPZGFNZOON-UHFFFAOYSA-N 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- JCRFTCBLQYLROG-UHFFFAOYSA-N cyclohexyl-phenyl-pyrrolidin-3-ylmethanol Chemical compound C1(CCCCC1)C(O)(C1CNCC1)C1=CC=CC=C1 JCRFTCBLQYLROG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- IGFVSRAMYPHRFF-UHFFFAOYSA-N n,n-diethyl-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-amine Chemical compound C1NCCOC2=CC(N(CC)CC)=CC=C21 IGFVSRAMYPHRFF-UHFFFAOYSA-N 0.000 abstract 1
- JGBRWOFWXRFLEG-UHFFFAOYSA-N n,n-diethyl-4-pyrrolidin-3-ylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1CNCC1 JGBRWOFWXRFLEG-UHFFFAOYSA-N 0.000 abstract 1
- GBQSYPAVGIYPLU-UHFFFAOYSA-N n-(2-methoxyphenyl)pyrrolidin-3-amine Chemical compound COC1=CC=CC=C1NC1CNCC1 GBQSYPAVGIYPLU-UHFFFAOYSA-N 0.000 abstract 1
- AAFUQJGCJNFFRT-UHFFFAOYSA-N n-phenylpyrrolidin-3-amine Chemical compound C1NCCC1NC1=CC=CC=C1 AAFUQJGCJNFFRT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- BVSOVZODSKMZJF-UHFFFAOYSA-N phenyl(pyrrolidin-3-yl)methanol Chemical compound C=1C=CC=CC=1C(O)C1CCNC1 BVSOVZODSKMZJF-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59226366A | 1966-11-07 | 1966-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1202747A true GB1202747A (en) | 1970-08-19 |
Family
ID=24369972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB50259/67A Expired GB1202747A (en) | 1966-11-07 | 1967-11-06 | 0,3-disubstituted pyrrolidines |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT272331B (enExample) |
| BE (1) | BE704683A (enExample) |
| CA (1) | CA955936A (enExample) |
| CH (1) | CH511834A (enExample) |
| DE (1) | DE1695652A1 (enExample) |
| DK (1) | DK133942B (enExample) |
| ES (1) | ES346816A1 (enExample) |
| FR (2) | FR1575543A (enExample) |
| GB (1) | GB1202747A (enExample) |
| IL (1) | IL28811A (enExample) |
| NL (1) | NL6714553A (enExample) |
| SE (1) | SE315594B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991010651A1 (en) * | 1990-01-06 | 1991-07-25 | Pfizer Limited | Anticholinergic agents |
| US8188301B2 (en) | 2007-06-05 | 2012-05-29 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54151990A (en) * | 1978-04-17 | 1979-11-29 | Beiersdorf Ag | Novel condensated nitrogenncontained heterocyclic compound and its manufacture |
-
1967
- 1967-10-04 BE BE704683D patent/BE704683A/xx unknown
- 1967-10-24 IL IL2881167A patent/IL28811A/xx unknown
- 1967-10-26 NL NL6714553A patent/NL6714553A/xx unknown
- 1967-11-02 CH CH1536867A patent/CH511834A/de not_active IP Right Cessation
- 1967-11-06 ES ES346816A patent/ES346816A1/es not_active Expired
- 1967-11-06 CA CA004,409A patent/CA955936A/en not_active Expired
- 1967-11-06 DK DK551967A patent/DK133942B/da unknown
- 1967-11-06 SE SE1517767A patent/SE315594B/xx unknown
- 1967-11-06 GB GB50259/67A patent/GB1202747A/en not_active Expired
- 1967-11-07 AT AT1003667A patent/AT272331B/de active
- 1967-11-07 DE DE19671695652 patent/DE1695652A1/de active Pending
- 1967-11-07 FR FR1575543D patent/FR1575543A/fr not_active Expired
-
1968
- 1968-02-06 FR FR138852A patent/FR7535M/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991010651A1 (en) * | 1990-01-06 | 1991-07-25 | Pfizer Limited | Anticholinergic agents |
| US8188301B2 (en) | 2007-06-05 | 2012-05-29 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission |
Also Published As
| Publication number | Publication date |
|---|---|
| CA955936A (en) | 1974-10-08 |
| DK133942B (da) | 1976-08-16 |
| FR1575543A (enExample) | 1969-07-25 |
| AT272331B (de) | 1969-07-10 |
| BE704683A (enExample) | 1968-02-15 |
| DE1695652A1 (de) | 1971-04-29 |
| ES346816A1 (es) | 1969-04-16 |
| FR7535M (enExample) | 1969-12-22 |
| CH511834A (de) | 1971-08-31 |
| SE315594B (enExample) | 1969-10-06 |
| NL6714553A (enExample) | 1968-05-08 |
| DK133942C (enExample) | 1977-01-24 |
| IL28811A (en) | 1971-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |