CN1136275A - 芳杂环基哌啶类、吡咯烷类及哌嗪类及其作为抗精神病药和止痛药的用途 - Google Patents
芳杂环基哌啶类、吡咯烷类及哌嗪类及其作为抗精神病药和止痛药的用途 Download PDFInfo
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- CN1136275A CN1136275A CN94194302A CN94194302A CN1136275A CN 1136275 A CN1136275 A CN 1136275A CN 94194302 A CN94194302 A CN 94194302A CN 94194302 A CN94194302 A CN 94194302A CN 1136275 A CN1136275 A CN 1136275A
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- chemical compound
- fluoro
- acid addition
- addition salt
- piperidino
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- 230000000202 analgesic effect Effects 0.000 title claims description 10
- 150000003235 pyrrolidines Chemical class 0.000 title abstract description 12
- 239000000164 antipsychotic agent Substances 0.000 title abstract 2
- 229940005529 antipsychotics Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 337
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 18
- 230000000561 anti-psychotic effect Effects 0.000 claims abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims abstract 18
- -1 alkanoyl oxygen Chemical compound 0.000 claims description 375
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 341
- 229910052739 hydrogen Inorganic materials 0.000 claims description 299
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 299
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 228
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 227
- 229910052799 carbon Inorganic materials 0.000 claims description 204
- 229910052757 nitrogen Inorganic materials 0.000 claims description 193
- 125000000217 alkyl group Chemical group 0.000 claims description 167
- 239000000203 mixture Substances 0.000 claims description 166
- 150000003839 salts Chemical class 0.000 claims description 163
- 239000002253 acid Substances 0.000 claims description 136
- 239000001257 hydrogen Substances 0.000 claims description 129
- 229910052760 oxygen Inorganic materials 0.000 claims description 106
- 239000003921 oil Substances 0.000 claims description 98
- 235000019198 oils Nutrition 0.000 claims description 98
- 239000001301 oxygen Substances 0.000 claims description 92
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 80
- 150000002431 hydrogen Chemical group 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 66
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 239000000460 chlorine Substances 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 45
- 229910052794 bromium Inorganic materials 0.000 claims description 44
- 229910052731 fluorine Inorganic materials 0.000 claims description 44
- 239000011737 fluorine Substances 0.000 claims description 41
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 38
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 35
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 34
- 125000002252 acyl group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 31
- 230000009471 action Effects 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 229910052740 iodine Inorganic materials 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 16
- 239000003937 drug carrier Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 239000011630 iodine Substances 0.000 claims description 16
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 16
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 14
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 14
- 150000003053 piperidines Chemical class 0.000 claims description 14
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 238000003860 storage Methods 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000004519 grease Substances 0.000 claims description 8
- 210000000582 semen Anatomy 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical group CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000005936 piperidyl group Chemical group 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- QXNCRJVBIMSYRT-UHFFFAOYSA-N isoindole-1,3-dione;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)NC(=O)C2=C1 QXNCRJVBIMSYRT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000002333 glycines Chemical class 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 5
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 4
- GQBONCZDJQXPLV-UHFFFAOYSA-N 4-aminoisoindole-1,3-dione Chemical compound NC1=CC=CC2=C1C(=O)NC2=O GQBONCZDJQXPLV-UHFFFAOYSA-N 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- 239000004006 olive oil Substances 0.000 claims 2
- 235000008390 olive oil Nutrition 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- HVECBZCDZNZAFL-LLVKDONJSA-N (2r)-4-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]butan-2-ol Chemical group C1CN(CC[C@H](O)C)CCC1C1=NOC2=CC(F)=CC=C12 HVECBZCDZNZAFL-LLVKDONJSA-N 0.000 claims 1
- HVECBZCDZNZAFL-NSHDSACASA-N (2s)-4-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]butan-2-ol Chemical group C1CN(CC[C@@H](O)C)CCC1C1=NOC2=CC(F)=CC=C12 HVECBZCDZNZAFL-NSHDSACASA-N 0.000 claims 1
- RJEMYCPJFRNHRU-UHFFFAOYSA-N 1-amino-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propan-2-ol Chemical group C1CN(CC(O)CN)CCC1C1=NOC2=CC(F)=CC=C12 RJEMYCPJFRNHRU-UHFFFAOYSA-N 0.000 claims 1
- WLHXSZZQMFFRTO-UHFFFAOYSA-N 2-[2-[4-(1-benzoyl-6-fluoroindazol-3-yl)piperazin-1-yl]ethyl]isoindole-1,3-dione Chemical group C12=CC(F)=CC=C2C(N2CCN(CCN3C(C4=CC=CC=C4C3=O)=O)CC2)=NN1C(=O)C1=CC=CC=C1 WLHXSZZQMFFRTO-UHFFFAOYSA-N 0.000 claims 1
- VVBQNUZMWLJARD-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1,2-benzothiazol-3-yl)piperidin-1-yl]ethyl]-5-methylisoindole-1,3-dione Chemical group FC1=CC=C2C(C3CCN(CC3)CCN3C(=O)C4=CC=C(C=C4C3=O)C)=NSC2=C1 VVBQNUZMWLJARD-UHFFFAOYSA-N 0.000 claims 1
- FDAOKFMMTDFDFV-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1,2-benzothiazol-3-yl)piperidin-1-yl]ethyl]isoindole-1,3-dione Chemical group O=C1C2=CC=CC=C2C(=O)N1CCN(CC1)CCC1C1=NSC2=CC(F)=CC=C21 FDAOKFMMTDFDFV-UHFFFAOYSA-N 0.000 claims 1
- ZQABIPHXILSLFR-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]butyl]isoindole-1,3-dione Chemical group FC1=CC=C2C(C3CCN(CC3)C(CN3C(C4=CC=CC=C4C3=O)=O)CC)=NOC2=C1 ZQABIPHXILSLFR-UHFFFAOYSA-N 0.000 claims 1
- XMYYXPYJRGYDIG-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-4-hydroxyisoindole-1,3-dione Chemical group FC1=CC=C2C(C3CCN(CC3)CCN3C(=O)C=4C=CC=C(C=4C3=O)O)=NOC2=C1 XMYYXPYJRGYDIG-UHFFFAOYSA-N 0.000 claims 1
- NCJTZDRJVQAVRP-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-4-nitroisoindole-1,3-dione Chemical group FC1=CC=C2C(C3CCN(CC3)CCN3C(=O)C=4C=CC=C(C=4C3=O)[N+](=O)[O-])=NOC2=C1 NCJTZDRJVQAVRP-UHFFFAOYSA-N 0.000 claims 1
- CUEBXHBBMACBBC-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-5-hydroxyisoindole-1,3-dione Chemical group FC1=CC=C2C(C3CCN(CC3)CCN3C(=O)C4=CC=C(C=C4C3=O)O)=NOC2=C1 CUEBXHBBMACBBC-UHFFFAOYSA-N 0.000 claims 1
- LLWNTMGOXQCUAE-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1h-indazol-3-yl)piperazin-1-yl]ethyl]-4-methylisoindole-1,3-dione Chemical group FC1=CC=C2C(N3CCN(CC3)CCN3C(=O)C=4C=CC=C(C=4C3=O)C)=NNC2=C1 LLWNTMGOXQCUAE-UHFFFAOYSA-N 0.000 claims 1
- ZRZHCSZFTOPAPM-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1h-indazol-3-yl)piperazin-1-yl]ethyl]-5-methylisoindole-1,3-dione Chemical group FC1=CC=C2C(N3CCN(CC3)CCN3C(=O)C4=CC=C(C=C4C3=O)C)=NNC2=C1 ZRZHCSZFTOPAPM-UHFFFAOYSA-N 0.000 claims 1
- REKLAPNBPQEPIU-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1h-indazol-3-yl)piperazin-1-yl]ethyl]isoindole-1,3-dione Chemical group O=C1C2=CC=CC=C2C(=O)N1CCN(CC1)CCN1C1=NNC2=CC(F)=CC=C21 REKLAPNBPQEPIU-UHFFFAOYSA-N 0.000 claims 1
- WVLVJXKALIXYPE-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-2h-indazol-3-yl)piperidin-1-yl]ethyl]isoindole-1,3-dione Chemical group O=C1C2=CC=CC=C2C(=O)N1CCN(CC1)CCC1C1=C2C=CC(F)=CC2=NN1 WVLVJXKALIXYPE-UHFFFAOYSA-N 0.000 claims 1
- GBMAXGZOXDNXPP-UHFFFAOYSA-N 2-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]butyl]isoindole-1,3-dione Chemical group FC1=CC=C2C(C3CCN(CC3)C(CCN3C(C4=CC=CC=C4C3=O)=O)C)=NOC2=C1 GBMAXGZOXDNXPP-UHFFFAOYSA-N 0.000 claims 1
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- ZBDHXTPKIBKYLI-UHFFFAOYSA-N 3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-2-methylquinazolin-4-one Chemical group FC1=CC=C2C(C3CCN(CC3)CCN3C(=O)C4=CC=CC=C4N=C3C)=NOC2=C1 ZBDHXTPKIBKYLI-UHFFFAOYSA-N 0.000 claims 1
- KJICBAZHEXJVRC-UHFFFAOYSA-N 3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propanenitrile Chemical compound N=1OC2=CC(F)=CC=C2C=1C1CCN(CCC#N)CC1 KJICBAZHEXJVRC-UHFFFAOYSA-N 0.000 claims 1
- ZLKNBGLWGAEYFP-UHFFFAOYSA-N 4,7-difluoro-2-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]isoindole-1,3-dione Chemical group O=C1C(C(=CC=C2F)F)=C2C(=O)N1CCN(CC1)CCC1C1=NOC2=CC(F)=CC=C21 ZLKNBGLWGAEYFP-UHFFFAOYSA-N 0.000 claims 1
- SKZDKWLLMXCFBI-UHFFFAOYSA-N 4-[4-(6-fluoro-1,2-benzothiazol-3-yl)piperidin-1-yl]-2-methylbutan-2-ol Chemical group C1CN(CCC(C)(O)C)CCC1C1=NSC2=CC(F)=CC=C12 SKZDKWLLMXCFBI-UHFFFAOYSA-N 0.000 claims 1
- HVECBZCDZNZAFL-UHFFFAOYSA-N 4-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]butan-2-ol Chemical group C1CN(CCC(O)C)CCC1C1=NOC2=CC(F)=CC=C12 HVECBZCDZNZAFL-UHFFFAOYSA-N 0.000 claims 1
- ZSNZZYJALRMOOI-UHFFFAOYSA-N 4-[4-(6-fluoro-1h-indazol-3-yl)piperazin-1-yl]-2-methylbutan-2-ol Chemical group C1CN(CCC(C)(O)C)CCN1C1=NNC2=CC(F)=CC=C12 ZSNZZYJALRMOOI-UHFFFAOYSA-N 0.000 claims 1
- KUJCQABMBAJNKG-UHFFFAOYSA-N 5-amino-2-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]isoindole-1,3-dione Chemical group FC1=CC=C2C(C3CCN(CC3)CCN3C(=O)C4=CC=C(C=C4C3=O)N)=NOC2=C1 KUJCQABMBAJNKG-UHFFFAOYSA-N 0.000 claims 1
- WDEWAYFLWYXJDG-UHFFFAOYSA-N 5-fluoro-2-[2-[4-(6-fluoro-1h-indazol-3-yl)piperazin-1-yl]ethyl]isoindole-1,3-dione Chemical group FC1=CC=C2C(N3CCN(CC3)CCN3C(=O)C4=CC=C(C=C4C3=O)F)=NNC2=C1 WDEWAYFLWYXJDG-UHFFFAOYSA-N 0.000 claims 1
- MBFSMBVSSNWKPI-UHFFFAOYSA-N 5-fluoro-2-[2-[4-(6-fluoro-2h-indazol-3-yl)piperidin-1-yl]ethyl]isoindole-1,3-dione Chemical group FC1=CC=C2C(C3CCN(CC3)CCN3C(=O)C4=CC=C(C=C4C3=O)F)=NNC2=C1 MBFSMBVSSNWKPI-UHFFFAOYSA-N 0.000 claims 1
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- BAMBWNHYCALWDP-UHFFFAOYSA-N n-[3-[3-[4-(6-fluoro-1,2-benzothiazol-3-yl)piperidin-1-yl]propoxy]-4-methoxyphenyl]acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3SN=2)CC1 BAMBWNHYCALWDP-UHFFFAOYSA-N 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- DJDBLBBSUAQYAA-UHFFFAOYSA-N piperazine-1-carbonitrile Chemical compound N#CN1CCNCC1 DJDBLBBSUAQYAA-UHFFFAOYSA-N 0.000 description 1
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- 150000003334 secondary amides Chemical class 0.000 description 1
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 1
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- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
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- 230000001954 sterilising effect Effects 0.000 description 1
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- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
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- 230000002123 temporal effect Effects 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
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Classifications
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- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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- 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
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- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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Abstract
Description
Claims (227)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US14426593A | 1993-10-28 | 1993-10-28 | |
US144265 | 1993-10-28 | ||
US08/329,000 US5776963A (en) | 1989-05-19 | 1994-10-25 | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
US329000 | 1994-10-25 | ||
US08/329,000 | 1994-10-25 |
Publications (2)
Publication Number | Publication Date |
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CN1136275A true CN1136275A (zh) | 1996-11-20 |
CN1143675C CN1143675C (zh) | 2004-03-31 |
Family
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Application Number | Title | Priority Date | Filing Date |
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CNB94194302XA Expired - Lifetime CN1143675C (zh) | 1993-10-28 | 1994-10-27 | 芳杂环基哌啶类、吡咯烷类及哌嗪类及其作为抗精神病药和止痛药的用途 |
Country Status (14)
Country | Link |
---|---|
US (66) | US5776963A (zh) |
EP (2) | EP0730452A4 (zh) |
JP (1) | JPH09511215A (zh) |
KR (2) | KR100795867B1 (zh) |
CN (1) | CN1143675C (zh) |
AU (1) | AU8122894A (zh) |
CA (1) | CA2175212C (zh) |
CZ (1) | CZ295927B6 (zh) |
NO (1) | NO306994B1 (zh) |
NZ (1) | NZ275941A (zh) |
PL (1) | PL181059B1 (zh) |
RO (1) | RO120341B1 (zh) |
RU (1) | RU2216545C2 (zh) |
WO (1) | WO1995011680A1 (zh) |
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