DE3000625A1 - Cis- und trans-isomere von 3-aryloxy- 4-hydroxypyrrolidinen und deren derivaten, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
Cis- und trans-isomere von 3-aryloxy- 4-hydroxypyrrolidinen und deren derivaten, verfahren zu ihrer herstellung und ihre verwendungInfo
- Publication number
- DE3000625A1 DE3000625A1 DE19803000625 DE3000625A DE3000625A1 DE 3000625 A1 DE3000625 A1 DE 3000625A1 DE 19803000625 DE19803000625 DE 19803000625 DE 3000625 A DE3000625 A DE 3000625A DE 3000625 A1 DE3000625 A1 DE 3000625A1
- Authority
- DE
- Germany
- Prior art keywords
- trans
- pyrrolidinol
- phenylmethyl
- deep
- ethyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 title description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 161
- 150000001875 compounds Chemical class 0.000 claims description 44
- -1 1-indenyl Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- AJLQKQUQJWEGMJ-IAGOWNOFSA-N (3r,4r)-1-benzyl-4-phenoxypyrrolidin-3-ol Chemical compound C([C@H]([C@@H](C1)OC=2C=CC=CC=2)O)N1CC1=CC=CC=C1 AJLQKQUQJWEGMJ-IAGOWNOFSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- MIFWKCCGJDJZPL-FOUVGRNNSA-M (3r,4r)-1-benzyl-1-methyl-4-phenoxypyrrolidin-1-ium-3-ol;iodide Chemical compound [I-].C([C@H]([C@H](O)C1)OC=2C=CC=CC=2)[N+]1(C)CC1=CC=CC=C1 MIFWKCCGJDJZPL-FOUVGRNNSA-M 0.000 claims description 3
- PBEDDLTYYGZKHB-VNYZMKMESA-N (3r,4r)-1-benzyl-4-(2,3-dichlorophenoxy)pyrrolidin-3-ol;hydrochloride Chemical compound Cl.C([C@H]([C@@H](C1)OC=2C(=C(Cl)C=CC=2)Cl)O)N1CC1=CC=CC=C1 PBEDDLTYYGZKHB-VNYZMKMESA-N 0.000 claims description 3
- XDRXBSMOERBHAQ-IEBWSBKVSA-N (3r,4r)-1-benzyl-4-(2,3-dimethylphenoxy)pyrrolidin-3-ol Chemical compound CC1=CC=CC(O[C@H]2[C@@H](CN(CC=3C=CC=CC=3)C2)O)=C1C XDRXBSMOERBHAQ-IEBWSBKVSA-N 0.000 claims description 3
- AHQFGIPCABOHHT-HZPDHXFCSA-N (3r,4r)-1-benzyl-4-(2,6-dichlorophenoxy)pyrrolidin-3-ol Chemical compound C([C@H]([C@@H](C1)OC=2C(=CC=CC=2Cl)Cl)O)N1CC1=CC=CC=C1 AHQFGIPCABOHHT-HZPDHXFCSA-N 0.000 claims description 3
- IWYRSDQVKDZTBL-VQIMIIECSA-N (3r,4r)-1-benzyl-4-(2-ethoxyphenoxy)pyrrolidin-3-ol Chemical compound CCOC1=CC=CC=C1O[C@H]1[C@H](O)CN(CC=2C=CC=CC=2)C1 IWYRSDQVKDZTBL-VQIMIIECSA-N 0.000 claims description 3
- UJVPOESHSNJQGX-IAGOWNOFSA-N (3r,4r)-1-benzyl-4-(4-chlorophenoxy)pyrrolidin-3-ol Chemical compound C([C@H]([C@@H](C1)OC=2C=CC(Cl)=CC=2)O)N1CC1=CC=CC=C1 UJVPOESHSNJQGX-IAGOWNOFSA-N 0.000 claims description 3
- KWIOFOMLPVXQCZ-QZTJIDSGSA-N (3r,4r)-1-benzyl-4-(4-methoxyphenoxy)pyrrolidin-3-ol Chemical compound C1=CC(OC)=CC=C1O[C@H]1[C@H](O)CN(CC=2C=CC=CC=2)C1 KWIOFOMLPVXQCZ-QZTJIDSGSA-N 0.000 claims description 3
- NFCMJWSHOFAWTH-VXGBXAGGSA-N (3r,4r)-3-(4-chlorophenoxy)-4-hydroxy-n,n-dimethylpyrrolidine-1-carboxamide Chemical compound C1N(C(=O)N(C)C)C[C@@H](O)[C@@H]1OC1=CC=C(Cl)C=C1 NFCMJWSHOFAWTH-VXGBXAGGSA-N 0.000 claims description 3
- KHEMRQFZQZAUDH-NXEZZACHSA-N (3r,4r)-4-(4-hydroxyphenoxy)pyrrolidin-3-ol Chemical compound O[C@@H]1CNC[C@H]1OC1=CC=C(O)C=C1 KHEMRQFZQZAUDH-NXEZZACHSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- LANQZGYGBHWTLH-VXGBXAGGSA-N n-[4-[(3r,4r)-4-hydroxypyrrolidin-3-yl]oxyphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1O[C@H]1[C@H](O)CNC1 LANQZGYGBHWTLH-VXGBXAGGSA-N 0.000 claims description 3
- LHWYGEZMXLGDJV-OJERSXHUSA-N (3R,4R)-1-ethyl-4-(3-methylphenoxy)pyrrolidin-3-ol oxalic acid Chemical compound OC(=O)C(O)=O.C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC(C)=C1 LHWYGEZMXLGDJV-OJERSXHUSA-N 0.000 claims description 2
- RNQPFBVNJMEXMP-GHMZBOCLSA-N (3R,4R)-3-(4-chlorophenoxy)-4-hydroxy-N-methylpyrrolidine-1-carboxamide Chemical compound C1N(C(=O)NC)C[C@@H](O)[C@@H]1OC1=CC=C(Cl)C=C1 RNQPFBVNJMEXMP-GHMZBOCLSA-N 0.000 claims description 2
- PMFUUDXGHFFZTA-JAXOOIEVSA-N (3r,4r)-1-benzyl-3-methoxy-4-phenoxypyrrolidine;oxalic acid Chemical compound OC(=O)C(O)=O.C([C@H]([C@@H](C1)OC=2C=CC=CC=2)OC)N1CC1=CC=CC=C1 PMFUUDXGHFFZTA-JAXOOIEVSA-N 0.000 claims description 2
- QHFFIZJTQMPRFA-GZJHNZOKSA-N (3r,4r)-1-benzyl-4-(2,3-dihydro-1h-inden-5-yloxy)pyrrolidin-3-ol;hydrochloride Chemical compound Cl.C([C@H]([C@@H](C1)OC=2C=C3CCCC3=CC=2)O)N1CC1=CC=CC=C1 QHFFIZJTQMPRFA-GZJHNZOKSA-N 0.000 claims description 2
- HBSADWOCIZZUMN-CRAIPNDOSA-N (3r,4r)-1-benzyl-4-(2-methoxyphenoxy)pyrrolidin-3-ol Chemical compound COC1=CC=CC=C1O[C@H]1[C@H](O)CN(CC=2C=CC=CC=2)C1 HBSADWOCIZZUMN-CRAIPNDOSA-N 0.000 claims description 2
- FXXAQQLSLHYSBX-JAXOOIEVSA-N (3r,4r)-1-benzyl-4-(3-methylphenoxy)pyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1=CC=CC(O[C@H]2[C@@H](CN(CC=3C=CC=CC=3)C2)O)=C1 FXXAQQLSLHYSBX-JAXOOIEVSA-N 0.000 claims description 2
- VGQAXYKSPUSVOM-DNQXCXABSA-N (3r,4r)-1-benzyl-4-(4-phenylmethoxyphenoxy)pyrrolidin-3-ol Chemical compound C([C@H]([C@@H](C1)OC=2C=CC(OCC=3C=CC=CC=3)=CC=2)O)N1CC1=CC=CC=C1 VGQAXYKSPUSVOM-DNQXCXABSA-N 0.000 claims description 2
- AHWUNRIRDXQYFE-IAGOWNOFSA-N (3r,4r)-1-benzyl-4-[3-(trifluoromethyl)phenoxy]pyrrolidin-3-ol Chemical compound C([C@H]([C@@H](C1)OC=2C=C(C=CC=2)C(F)(F)F)O)N1CC1=CC=CC=C1 AHWUNRIRDXQYFE-IAGOWNOFSA-N 0.000 claims description 2
- YOVYVWUZPUTOSI-GBNZRNLASA-N (3r,4r)-1-benzyl-4-[3-(trifluoromethyl)phenoxy]pyrrolidin-3-ol;oxalic acid Chemical compound OC(=O)C(O)=O.C([C@H]([C@@H](C1)OC=2C=C(C=CC=2)C(F)(F)F)O)N1CC1=CC=CC=C1 YOVYVWUZPUTOSI-GBNZRNLASA-N 0.000 claims description 2
- YLGWDNXLWSRKND-GNGUGDOWSA-N (3r,4r)-1-benzyl-4-naphthalen-1-yloxypyrrolidin-3-ol;oxalic acid Chemical compound OC(=O)C(O)=O.C([C@H]([C@@H](C1)OC=2C3=CC=CC=C3C=CC=2)O)N1CC1=CC=CC=C1 YLGWDNXLWSRKND-GNGUGDOWSA-N 0.000 claims description 2
- KRUHYUORPUDVNQ-UKRRQHHQSA-N (3r,4r)-1-ethyl-4-(2-prop-2-enylphenoxy)pyrrolidin-3-ol Chemical compound C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC=C1CC=C KRUHYUORPUDVNQ-UKRRQHHQSA-N 0.000 claims description 2
- YMJGRBHQKMNQQR-SWYZXDRTSA-N (3r,4r)-1-ethyl-4-(2-prop-2-enylphenoxy)pyrrolidin-3-ol;oxalic acid Chemical compound OC(=O)C(O)=O.C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC=C1CC=C YMJGRBHQKMNQQR-SWYZXDRTSA-N 0.000 claims description 2
- ZJVXBJDRCMGOSH-VNYZMKMESA-N (3r,4r)-1-ethyl-4-naphthalen-1-yloxypyrrolidin-3-ol;hydrochloride Chemical compound Cl.C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC2=CC=CC=C12 ZJVXBJDRCMGOSH-VNYZMKMESA-N 0.000 claims description 2
- KOYSMNHLBIJMFS-GHMZBOCLSA-N (3r,4r)-1-methyl-4-phenoxypyrrolidin-3-ol Chemical compound C1N(C)C[C@@H](O)[C@@H]1OC1=CC=CC=C1 KOYSMNHLBIJMFS-GHMZBOCLSA-N 0.000 claims description 2
- XIUSPFPZUQUUBR-OJERSXHUSA-N (3r,4r)-4-(2,3-dihydro-1h-inden-5-yloxy)pyrrolidin-3-ol;oxalic acid Chemical compound OC(=O)C(O)=O.O[C@@H]1CNC[C@H]1OC1=CC=C(CCC2)C2=C1 XIUSPFPZUQUUBR-OJERSXHUSA-N 0.000 claims description 2
- RSDIYSLVUYXFHZ-MHDYBILJSA-N (3r,4r)-4-(2,3-dimethylphenoxy)pyrrolidin-3-ol;hydrobromide Chemical compound Br.CC1=CC=CC(O[C@H]2[C@@H](CNC2)O)=C1C RSDIYSLVUYXFHZ-MHDYBILJSA-N 0.000 claims description 2
- MECYPUPCCKBGSU-NDXYWBNTSA-N (3r,4r)-4-(2,6-dichlorophenoxy)-1-ethylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.C1N(CC)C[C@@H](O)[C@@H]1OC1=C(Cl)C=CC=C1Cl MECYPUPCCKBGSU-NDXYWBNTSA-N 0.000 claims description 2
- JHFAGQNTDUJDRD-MHDYBILJSA-N (3r,4r)-4-(2-chlorophenoxy)-1-ethylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC=C1Cl JHFAGQNTDUJDRD-MHDYBILJSA-N 0.000 claims description 2
- XWQXOWUBFRSUBR-BXUZGUMPSA-N (3r,4r)-4-(2-ethoxyphenoxy)-1-ethylpyrrolidin-3-ol Chemical compound CCOC1=CC=CC=C1O[C@H]1[C@H](O)CN(CC)C1 XWQXOWUBFRSUBR-BXUZGUMPSA-N 0.000 claims description 2
- ZCSJAJCLFSFOLS-NDXYWBNTSA-N (3r,4r)-4-(3-methylphenoxy)pyrrolidin-3-ol;oxalic acid Chemical compound OC(=O)C(O)=O.CC1=CC=CC(O[C@H]2[C@@H](CNC2)O)=C1 ZCSJAJCLFSFOLS-NDXYWBNTSA-N 0.000 claims description 2
- GOIMBJDPXKLUBW-NDXYWBNTSA-N (3r,4r)-4-(4-methoxyphenoxy)pyrrolidin-3-ol;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OC)=CC=C1O[C@H]1[C@H](O)CNC1 GOIMBJDPXKLUBW-NDXYWBNTSA-N 0.000 claims description 2
- CTSOJIDXHXPAKX-DHTOPLTISA-N (3r,4r)-4-[3-(trifluoromethyl)phenoxy]pyrrolidin-3-ol;hydrochloride Chemical compound Cl.O[C@@H]1CNC[C@H]1OC1=CC=CC(C(F)(F)F)=C1 CTSOJIDXHXPAKX-DHTOPLTISA-N 0.000 claims description 2
- QRDWNJTVUHULPK-TZMCWYRMSA-N (3r,4r)-4-naphthalen-1-yloxypyrrolidin-3-ol Chemical compound O[C@@H]1CNC[C@H]1OC1=CC=CC2=CC=CC=C12 QRDWNJTVUHULPK-TZMCWYRMSA-N 0.000 claims description 2
- MOAJANUWVDXXRK-PPECYIBVSA-N (e)-but-2-enedioic acid;(3r,4r)-3-methoxy-4-phenoxypyrrolidine Chemical compound OC(=O)\C=C\C(O)=O.CO[C@@H]1CNC[C@H]1OC1=CC=CC=C1 MOAJANUWVDXXRK-PPECYIBVSA-N 0.000 claims description 2
- SFIFRXRXKZMHAV-KORILMBXSA-N (e)-but-2-enedioic acid;(3r,4r)-4-(2-ethoxyphenoxy)pyrrolidin-3-ol Chemical compound OC(=O)\C=C\C(O)=O.CCOC1=CC=CC=C1O[C@H]1[C@H](O)CNC1 SFIFRXRXKZMHAV-KORILMBXSA-N 0.000 claims description 2
- XTACKTGKYRPLPX-ZBHVTWHQSA-N (e)-but-2-enedioic acid;(3r,4r)-4-(2-methoxyphenoxy)pyrrolidin-3-ol Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC=CC=C1O[C@H]1[C@H](O)CNC1 XTACKTGKYRPLPX-ZBHVTWHQSA-N 0.000 claims description 2
- SNMGDSFQRAWQEI-BZALSJTCSA-N (e)-but-2-enedioic acid;(3r,4r)-4-phenoxypyrrolidin-3-ol Chemical compound OC(=O)\C=C\C(O)=O.O[C@@H]1CNC[C@H]1OC1=CC=CC=C1 SNMGDSFQRAWQEI-BZALSJTCSA-N 0.000 claims description 2
- MHYKQTUWSKONNC-RTBURBONSA-N 1-(4-fluorophenyl)-3-[(3r,4r)-3-hydroxy-4-phenoxypyrrolidin-1-yl]propan-1-one Chemical compound C([C@H]([C@@H](C1)OC=2C=CC=CC=2)O)N1CCC(=O)C1=CC=C(F)C=C1 MHYKQTUWSKONNC-RTBURBONSA-N 0.000 claims description 2
- TXCKGARMKCWFGR-IAGOWNOFSA-N 4-[(3r,4r)-1-benzyl-4-hydroxypyrrolidin-3-yl]oxybenzamide Chemical compound C1=CC(C(=O)N)=CC=C1O[C@H]1[C@H](O)CN(CC=2C=CC=CC=2)C1 TXCKGARMKCWFGR-IAGOWNOFSA-N 0.000 claims description 2
- WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 claims description 2
- ITXSEDNGSWPYPJ-DHTOPLTISA-N Br.O[C@@H]1CNC[C@H]1OC1=CC=C(Cl)C=C1 Chemical compound Br.O[C@@H]1CNC[C@H]1OC1=CC=C(Cl)C=C1 ITXSEDNGSWPYPJ-DHTOPLTISA-N 0.000 claims description 2
- BMGXQZNZTGCBGX-PRCZDLBKSA-N Br.O[C@@H]1CNC[C@H]1OC1=CC=CC(Cl)=C1Cl Chemical compound Br.O[C@@H]1CNC[C@H]1OC1=CC=CC(Cl)=C1Cl BMGXQZNZTGCBGX-PRCZDLBKSA-N 0.000 claims description 2
- VCGXJDLOUSEVLE-IAGOWNOFSA-N [(3R,4R)-1-ethyl-4-(2-prop-2-enylphenoxy)pyrrolidin-3-yl] N-ethylcarbamate Chemical compound C(C)NC(=O)O[C@@H]1CN(C[C@H]1OC1=C(C=CC=C1)CC=C)CC VCGXJDLOUSEVLE-IAGOWNOFSA-N 0.000 claims description 2
- FNDWRKAOKRBPPZ-CHWSQXEVSA-N [(3r,4r)-4-(4-chlorophenoxy)-1-(dimethylcarbamoyl)pyrrolidin-3-yl] n-methylcarbamate Chemical compound CNC(=O)O[C@@H]1CN(C(=O)N(C)C)C[C@H]1OC1=CC=C(Cl)C=C1 FNDWRKAOKRBPPZ-CHWSQXEVSA-N 0.000 claims description 2
- XJUBUSOLKIQZFD-GDBMZVCRSA-N benzyl (3r,4r)-3-(2,3-dichlorophenoxy)-4-hydroxypyrrolidine-1-carboxylate Chemical compound O([C@@H]1CN(C[C@H]1O)C(=O)OCC=1C=CC=CC=1)C1=CC=CC(Cl)=C1Cl XJUBUSOLKIQZFD-GDBMZVCRSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- ZXIDMMHTXZOWDR-RKDXNWHRSA-N (3r,4r)-4-(2,6-dichlorophenoxy)pyrrolidin-3-ol Chemical compound O[C@@H]1CNC[C@H]1OC1=C(Cl)C=CC=C1Cl ZXIDMMHTXZOWDR-RKDXNWHRSA-N 0.000 claims 2
- HTANDCOSJQNAFZ-CHWSQXEVSA-N (3R,4R)-1-ethyl-4-(3-methylphenoxy)pyrrolidin-3-ol Chemical compound C(C)N1C[C@H]([C@@H](C1)OC1=CC(=CC=C1)C)O HTANDCOSJQNAFZ-CHWSQXEVSA-N 0.000 claims 1
- CXLGZWGTLCSHCE-QZTJIDSGSA-N (3r,4r)-1-benzyl-3-methoxy-4-phenoxypyrrolidine Chemical compound C([C@H]([C@@H](C1)OC=2C=CC=CC=2)OC)N1CC1=CC=CC=C1 CXLGZWGTLCSHCE-QZTJIDSGSA-N 0.000 claims 1
- JPZRTQQKFWBUMM-GDBMZVCRSA-N (3r,4r)-1-benzyl-4-(2,3-dichlorophenoxy)pyrrolidin-3-ol Chemical compound C([C@H]([C@@H](C1)OC=2C(=C(Cl)C=CC=2)Cl)O)N1CC1=CC=CC=C1 JPZRTQQKFWBUMM-GDBMZVCRSA-N 0.000 claims 1
- WKFSADCIFQLBMD-WOJBJXKFSA-N (3r,4r)-1-benzyl-4-(2,3-dihydro-1h-inden-5-yloxy)pyrrolidin-3-ol Chemical compound C([C@H]([C@@H](C1)OC=2C=C3CCCC3=CC=2)O)N1CC1=CC=CC=C1 WKFSADCIFQLBMD-WOJBJXKFSA-N 0.000 claims 1
- JAWUAQLRGZILKQ-QZTJIDSGSA-N (3r,4r)-1-benzyl-4-(3-methylphenoxy)pyrrolidin-3-ol Chemical compound CC1=CC=CC(O[C@H]2[C@@H](CN(CC=3C=CC=CC=3)C2)O)=C1 JAWUAQLRGZILKQ-QZTJIDSGSA-N 0.000 claims 1
- PLUAOBUHCZJLJM-TZIWHRDSSA-N (3r,4r)-1-benzyl-4-naphthalen-1-yloxypyrrolidin-3-ol Chemical compound C([C@H]([C@@H](C1)OC=2C3=CC=CC=C3C=CC=2)O)N1CC1=CC=CC=C1 PLUAOBUHCZJLJM-TZIWHRDSSA-N 0.000 claims 1
- XHYQABMLPDAYEI-HZPDHXFCSA-N (3r,4r)-1-cyclohexyl-4-phenoxypyrrolidin-3-ol Chemical compound O([C@@H]1CN(C[C@H]1O)C1CCCCC1)C1=CC=CC=C1 XHYQABMLPDAYEI-HZPDHXFCSA-N 0.000 claims 1
- LVMACDSVFPQQER-GDBMZVCRSA-N (3r,4r)-1-ethyl-4-naphthalen-1-yloxypyrrolidin-3-ol Chemical compound C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC2=CC=CC=C12 LVMACDSVFPQQER-GDBMZVCRSA-N 0.000 claims 1
- XHMHZEARAIFOJZ-VXGBXAGGSA-N (3r,4r)-1-ethyl-4-phenoxypyrrolidin-3-ol Chemical compound C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC=C1 XHMHZEARAIFOJZ-VXGBXAGGSA-N 0.000 claims 1
- XKTRSTQLVUNLBA-MBORUXJMSA-N (3r,4r)-1-ethyl-4-phenoxypyrrolidin-3-ol;oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O.C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC=C1 XKTRSTQLVUNLBA-MBORUXJMSA-N 0.000 claims 1
- BPPRLMDOEBFYOJ-NXEZZACHSA-N (3r,4r)-3-(4-chlorophenoxy)-4-hydroxypyrrolidine-1-carboxamide Chemical compound C1N(C(=O)N)C[C@@H](O)[C@@H]1OC1=CC=C(Cl)C=C1 BPPRLMDOEBFYOJ-NXEZZACHSA-N 0.000 claims 1
- RSLMLWKSZKKJOY-GHMZBOCLSA-N (3r,4r)-3-methoxy-4-phenoxypyrrolidine Chemical compound CO[C@@H]1CNC[C@H]1OC1=CC=CC=C1 RSLMLWKSZKKJOY-GHMZBOCLSA-N 0.000 claims 1
- PZKKEUJEOIHRBY-VXNVDRBHSA-N (3r,4r)-4-(2,3-dichlorophenoxy)pyrrolidin-3-ol Chemical compound O[C@@H]1CNC[C@H]1OC1=CC=CC(Cl)=C1Cl PZKKEUJEOIHRBY-VXNVDRBHSA-N 0.000 claims 1
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- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 description 1
- NTBZGZFMDADSMQ-UHFFFAOYSA-N 3-benzyl-6-oxa-3-azabicyclo[3.1.0]hexane;oxalic acid Chemical compound OC(=O)C(O)=O.C1C2OC2CN1CC1=CC=CC=C1 NTBZGZFMDADSMQ-UHFFFAOYSA-N 0.000 description 1
- VYGBFVRBIUSTSM-UHFFFAOYSA-N 3-cyclohexyl-6-oxa-3-azabicyclo[3.1.0]hexane;oxalic acid Chemical compound OC(=O)C(O)=O.C1C2OC2CN1C1CCCCC1 VYGBFVRBIUSTSM-UHFFFAOYSA-N 0.000 description 1
- RDPWBWXKWOYYID-UHFFFAOYSA-N 3-ethyl-6-oxa-3-azabicyclo[3.1.0]hexane;oxalic acid Chemical compound OC(=O)C(O)=O.C1N(CC)CC2OC21 RDPWBWXKWOYYID-UHFFFAOYSA-N 0.000 description 1
- JJMHAOLFRDELQE-UHFFFAOYSA-N 4-(2-chlorophenoxy)pyrrolidin-3-ol Chemical compound OC1CNCC1OC1=CC=CC=C1Cl JJMHAOLFRDELQE-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- KSSRVICONDWLSU-UHFFFAOYSA-N 4-phenoxypyrrolidin-3-ol Chemical compound OC1CNCC1OC1=CC=CC=C1 KSSRVICONDWLSU-UHFFFAOYSA-N 0.000 description 1
- MKJIEFSOBYUXJB-UHFFFAOYSA-N 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2CC(CC(C)C)C(=O)CC2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- ZWIRGQILIYJWPM-VTLYIQCISA-N Br.O[C@@H]1CNC[C@H]1OC1=C(Cl)C=CC=C1Cl Chemical compound Br.O[C@@H]1CNC[C@H]1OC1=C(Cl)C=CC=C1Cl ZWIRGQILIYJWPM-VTLYIQCISA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 244000018764 Nyssa sylvatica Species 0.000 description 1
- 235000003339 Nyssa sylvatica Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- YWZUEPMOWCDZAA-UHFFFAOYSA-N [3-(4-fluorophenyl)-3-oxopropyl]-dimethylazanium;chloride Chemical compound Cl.CN(C)CCC(=O)C1=CC=C(F)C=C1 YWZUEPMOWCDZAA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 239000002220 antihypertensive agent Substances 0.000 description 1
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- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- YGGAXGOLDSWWRG-UHFFFAOYSA-N n-[4-(1-benzyl-4-hydroxypyrrolidin-3-yl)oxyphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OC1C(O)CN(CC=2C=CC=CC=2)C1 YGGAXGOLDSWWRG-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 229960003343 ouabain Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003236 pyrrolines Chemical class 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US215179A | 1979-01-09 | 1979-01-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3000625A1 true DE3000625A1 (de) | 1980-07-17 |
| DE3000625C2 DE3000625C2 (enrdf_load_stackoverflow) | 1989-04-20 |
Family
ID=21699450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803000625 Granted DE3000625A1 (de) | 1979-01-09 | 1980-01-09 | Cis- und trans-isomere von 3-aryloxy- 4-hydroxypyrrolidinen und deren derivaten, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5598160A (enrdf_load_stackoverflow) |
| CA (1) | CA1133495A (enrdf_load_stackoverflow) |
| CH (1) | CH643243A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3000625A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2446279B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2040933B (enrdf_load_stackoverflow) |
| IT (1) | IT1127967B (enrdf_load_stackoverflow) |
| MX (1) | MX6634E (enrdf_load_stackoverflow) |
| SE (1) | SE435927B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4320137A (en) | 1976-09-01 | 1982-03-16 | Ciba-Geigy Corporation | Derivatives of perhydro-aza-heterocycles |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547514A (en) * | 1983-12-05 | 1985-10-15 | A. H. Robins Company, Incorporated | Aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides having antiarrhythmic activity |
| JPS60178860A (ja) * | 1984-02-24 | 1985-09-12 | Sankyo Co Ltd | ３−メルカプトピロリジンまたはその塩の製法 |
| JPS6157552A (ja) * | 1984-08-29 | 1986-03-24 | Toyama Chem Co Ltd | ３−アミノピロリジンまたはその塩の製法 |
| DE3813416A1 (de) * | 1988-04-21 | 1989-11-02 | Hoechst Ag | 3,4-dihydroxypyrrolidin-2-on-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte |
| EP0407701A3 (en) * | 1989-05-15 | 1992-04-22 | Fujisawa Pharmaceutical Co., Ltd. | Antiretroviral pyrroline and pyrrolidine sulfonic acid derivatives |
| WO2008150470A1 (en) | 2007-05-31 | 2008-12-11 | Shionogi & Co., Ltd. | Oxyimino compounds and the use thereof |
| US8518934B2 (en) | 2008-06-11 | 2013-08-27 | Shonogi & Co., Ltd. | Oxycarbamoyl compounds and the use thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3577415A (en) * | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-substituted phenoxypyrrolidines |
| DE2738477A1 (de) * | 1976-09-01 | 1978-03-02 | Ciba Geigy Ag | Neue derivate von perhydro-aza- heterocyclen und verfahren zu ihrer herstellung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1000308A (fr) * | 1949-05-28 | 1952-02-11 | Basf Ag | Procédé pour la production de 3. 4-dioxypyrrolidines |
| FR1000310A (fr) * | 1949-06-18 | 1952-02-11 | Basf Ag | Procédé pour la production de dérivés de pyrrolidine |
| FR1532221A (fr) * | 1963-10-22 | 1968-07-12 | Robins Co Inc A H | Procédé de production de n, n-di (aryl monocarbocyclique)-carbamates de 1-(alkylinférieur)-3-pyrrolidyle |
| CH521338A (de) * | 1967-03-13 | 1972-04-15 | Robins Co Inc A H | Verfahren zur Herstellung von neuen Pyrrolidinderivaten |
-
1980
- 1980-01-03 MX MX808576U patent/MX6634E/es unknown
- 1980-01-07 SE SE8000085A patent/SE435927B/sv not_active IP Right Cessation
- 1980-01-08 IT IT67020/80A patent/IT1127967B/it active
- 1980-01-08 FR FR8000272A patent/FR2446279B1/fr not_active Expired
- 1980-01-08 CH CH10280A patent/CH643243A5/fr not_active IP Right Cessation
- 1980-01-09 CA CA343,328A patent/CA1133495A/en not_active Expired
- 1980-01-09 DE DE19803000625 patent/DE3000625A1/de active Granted
- 1980-01-09 JP JP123280A patent/JPS5598160A/ja active Granted
- 1980-01-09 GB GB8000709A patent/GB2040933B/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3577415A (en) * | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-substituted phenoxypyrrolidines |
| DE2738477A1 (de) * | 1976-09-01 | 1978-03-02 | Ciba Geigy Ag | Neue derivate von perhydro-aza- heterocyclen und verfahren zu ihrer herstellung |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4320137A (en) | 1976-09-01 | 1982-03-16 | Ciba-Geigy Corporation | Derivatives of perhydro-aza-heterocycles |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2040933A (en) | 1980-09-03 |
| SE8000085L (sv) | 1980-08-26 |
| MX6634E (es) | 1985-09-12 |
| IT8067020A0 (it) | 1980-01-08 |
| DE3000625C2 (enrdf_load_stackoverflow) | 1989-04-20 |
| FR2446279A1 (fr) | 1980-08-08 |
| CA1133495A (en) | 1982-10-12 |
| GB2040933B (en) | 1983-07-20 |
| SE435927B (sv) | 1984-10-29 |
| FR2446279B1 (fr) | 1985-10-31 |
| IT1127967B (it) | 1986-05-28 |
| JPS5598160A (en) | 1980-07-25 |
| CH643243A5 (fr) | 1984-05-30 |
| JPS648621B2 (enrdf_load_stackoverflow) | 1989-02-14 |
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