CH649548A5 - 4-phenyl-4,5,6,7-tetrahydro-pyrrolo(2,3-c)pyridine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die diese verbindungen enthalten. - Google Patents
4-phenyl-4,5,6,7-tetrahydro-pyrrolo(2,3-c)pyridine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die diese verbindungen enthalten. Download PDFInfo
- Publication number
- CH649548A5 CH649548A5 CH5125/80A CH512580A CH649548A5 CH 649548 A5 CH649548 A5 CH 649548A5 CH 5125/80 A CH5125/80 A CH 5125/80A CH 512580 A CH512580 A CH 512580A CH 649548 A5 CH649548 A5 CH 649548A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- pyrrolo
- tetrahydro
- pyridine
- compounds
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 8
- YYLVBYQDRJYOTK-UHFFFAOYSA-N 4-phenyl-4,5,6,7-tetrahydro-1h-pyrrolo[2,3-c]pyridine Chemical compound C1NCC=2NC=CC=2C1C1=CC=CC=C1 YYLVBYQDRJYOTK-UHFFFAOYSA-N 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- CWLOFLFPSNCBFN-UHFFFAOYSA-N 2-bromo-4-(4-bromophenyl)-1,6-dimethyl-5,7-dihydro-4h-pyrrolo[2,3-c]pyridine Chemical compound C1=2C=C(Br)N(C)C=2CN(C)CC1C1=CC=C(Br)C=C1 CWLOFLFPSNCBFN-UHFFFAOYSA-N 0.000 claims 1
- LNVJOEISRQDAHH-UHFFFAOYSA-N 4-(4-bromophenyl)-1,3,6-trimethyl-2-pyrrolidin-1-yl-5,7-dihydro-4H-pyrrolo[2,3-c]pyridine Chemical compound CN1C(=C(C2=C1CN(CC2C2=CC=C(C=C2)Br)C)C)N2CCCC2 LNVJOEISRQDAHH-UHFFFAOYSA-N 0.000 claims 1
- HQVOLDSMHIXLGI-UHFFFAOYSA-N 4-(4-bromophenyl)-1-methyl-4,5,6,7-tetrahydropyrrolo[2,3-c]pyridine Chemical compound C1NCC=2N(C)C=CC=2C1C1=CC=C(Br)C=C1 HQVOLDSMHIXLGI-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 6
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- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical group O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 6
- 229960003147 reserpine Drugs 0.000 description 6
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229960002748 norepinephrine Drugs 0.000 description 5
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 230000005764 inhibitory process Effects 0.000 description 4
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
- -1 pyrrolo- [2,3-c] pyridine maleinate Chemical compound 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- QLSJOGIENLKPTF-BTJKTKAUSA-N (z)-but-2-enedioic acid;pyridine Chemical compound C1=CC=NC=C1.OC(=O)\C=C/C(O)=O QLSJOGIENLKPTF-BTJKTKAUSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- WIBUSVGJVAYNBU-UHFFFAOYSA-N 4-(4-bromophenyl)-1,6-dimethyl-5,7-dihydro-4h-pyrrolo[2,3-c]pyridine Chemical compound C1=2C=CN(C)C=2CN(C)CC1C1=CC=C(Br)C=C1 WIBUSVGJVAYNBU-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
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- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
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- 229920000084 Gum arabic Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZFKXZALCMBWUCH-UHFFFAOYSA-N N-[[4-(4-bromophenyl)-1,6-dimethyl-5,7-dihydro-4H-pyrrolo[2,3-c]pyridin-2-yl]methyl]-N-ethylethanamine Chemical compound C1N(C)CC=2N(C)C(CN(CC)CC)=CC=2C1C1=CC=C(Br)C=C1 ZFKXZALCMBWUCH-UHFFFAOYSA-N 0.000 description 1
- SFIZFKDGZSAOKQ-UHFFFAOYSA-N N1CCC2C1=CN=CC2 Chemical compound N1CCC2C1=CN=CC2 SFIZFKDGZSAOKQ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- IQYABPVWEDBKPI-UHFFFAOYSA-N [4-(4-chlorophenyl)-1,6-dimethyl-5,7-dihydro-4h-pyrrolo[2,3-c]pyridin-2-yl]methanol Chemical compound C1=2C=C(CO)N(C)C=2CN(C)CC1C1=CC=C(Cl)C=C1 IQYABPVWEDBKPI-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 210000004720 cerebrum Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229950006768 phenylethanolamine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (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)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792927294 DE2927294A1 (de) | 1979-07-06 | 1979-07-06 | Neue 4-phenyl-4,5,6,7-tetrahydropyrrolo eckige klammer auf 2,3-c eckige klammer zu pyridine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH649548A5 true CH649548A5 (de) | 1985-05-31 |
Family
ID=6075042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5125/80A CH649548A5 (de) | 1979-07-06 | 1980-07-03 | 4-phenyl-4,5,6,7-tetrahydro-pyrrolo(2,3-c)pyridine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die diese verbindungen enthalten. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4315938A (OSRAM) |
| JP (1) | JPS5610184A (OSRAM) |
| AT (1) | AT375077B (OSRAM) |
| AU (1) | AU536336B2 (OSRAM) |
| BE (1) | BE884193A (OSRAM) |
| CA (1) | CA1138864A (OSRAM) |
| CH (1) | CH649548A5 (OSRAM) |
| DE (1) | DE2927294A1 (OSRAM) |
| DK (1) | DK290380A (OSRAM) |
| ES (1) | ES8201019A1 (OSRAM) |
| FI (1) | FI802148A7 (OSRAM) |
| FR (1) | FR2460950A1 (OSRAM) |
| GB (1) | GB2054580B (OSRAM) |
| GR (1) | GR69327B (OSRAM) |
| HU (1) | HU182152B (OSRAM) |
| IL (1) | IL60499A (OSRAM) |
| IT (1) | IT1150024B (OSRAM) |
| LU (1) | LU82582A1 (OSRAM) |
| NL (1) | NL8003879A (OSRAM) |
| NO (1) | NO802014L (OSRAM) |
| NZ (1) | NZ194245A (OSRAM) |
| PH (1) | PH15756A (OSRAM) |
| PT (1) | PT71500B (OSRAM) |
| SE (1) | SE436747B (OSRAM) |
| YU (1) | YU174780A (OSRAM) |
| ZA (1) | ZA804031B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5890951A (ja) * | 1981-11-26 | 1983-05-30 | 住友金属工業株式会社 | 耐食性にすぐれた積層板 |
| JPS59193175A (ja) * | 1983-04-19 | 1984-11-01 | Toa Nenryo Kogyo Kk | 積層物 |
| US4572911A (en) * | 1984-08-02 | 1986-02-25 | Mcneilab, Inc. | Hexahydroindolinzine compounds, pharmaceutical compositions and methods and intermediates |
| WO2021021953A2 (en) * | 2019-07-30 | 2021-02-04 | Sanford Burnham Prebys Medical Discovery Institute | Dopamine receptor d1 agonists and methods of use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1484140A (en) * | 1974-04-24 | 1977-08-24 | Wyeth John & Brother Ltd | Pyrrolopyridine derivatives |
| AT368504B (de) * | 1977-10-15 | 1982-10-25 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer 4-phenyl-thieno- (2,3-c)-piperidine |
-
1979
- 1979-07-06 DE DE19792927294 patent/DE2927294A1/de not_active Withdrawn
-
1980
- 1980-06-30 US US06/163,969 patent/US4315938A/en not_active Expired - Lifetime
- 1980-06-30 IT IT23120/80A patent/IT1150024B/it active
- 1980-07-02 AT AT0344680A patent/AT375077B/de not_active IP Right Cessation
- 1980-07-03 YU YU01747/80A patent/YU174780A/xx unknown
- 1980-07-03 GR GR62353A patent/GR69327B/el unknown
- 1980-07-03 CH CH5125/80A patent/CH649548A5/de not_active IP Right Cessation
- 1980-07-04 LU LU82582A patent/LU82582A1/de unknown
- 1980-07-04 FI FI802148A patent/FI802148A7/fi not_active Application Discontinuation
- 1980-07-04 ES ES493104A patent/ES8201019A1/es not_active Expired
- 1980-07-04 NZ NZ194245A patent/NZ194245A/en unknown
- 1980-07-04 BE BE0/201313A patent/BE884193A/fr not_active IP Right Cessation
- 1980-07-04 HU HU801678A patent/HU182152B/hu unknown
- 1980-07-04 FR FR8015010A patent/FR2460950A1/fr active Granted
- 1980-07-04 GB GB8022046A patent/GB2054580B/en not_active Expired
- 1980-07-04 JP JP9161580A patent/JPS5610184A/ja active Pending
- 1980-07-04 NO NO802014A patent/NO802014L/no unknown
- 1980-07-04 IL IL60499A patent/IL60499A/xx unknown
- 1980-07-04 NL NL8003879A patent/NL8003879A/nl not_active Application Discontinuation
- 1980-07-04 AU AU60138/80A patent/AU536336B2/en not_active Ceased
- 1980-07-04 DK DK290380A patent/DK290380A/da not_active Application Discontinuation
- 1980-07-04 SE SE8004976A patent/SE436747B/sv unknown
- 1980-07-04 PT PT71500A patent/PT71500B/pt unknown
- 1980-07-04 CA CA000355540A patent/CA1138864A/en not_active Expired
- 1980-07-04 ZA ZA00804031A patent/ZA804031B/xx unknown
- 1980-07-07 PH PH24246A patent/PH15756A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2460950B1 (OSRAM) | 1983-06-24 |
| CA1138864A (en) | 1983-01-04 |
| HU182152B (en) | 1983-12-28 |
| ES493104A0 (es) | 1981-11-01 |
| ZA804031B (en) | 1982-03-31 |
| GB2054580B (en) | 1983-04-07 |
| ATA344680A (de) | 1983-11-15 |
| LU82582A1 (de) | 1981-09-10 |
| IL60499A0 (en) | 1980-09-16 |
| IT1150024B (it) | 1986-12-10 |
| IL60499A (en) | 1984-02-29 |
| GB2054580A (en) | 1981-02-18 |
| AU6013880A (en) | 1981-01-15 |
| PT71500A (de) | 1980-08-01 |
| DE2927294A1 (de) | 1981-01-08 |
| US4315938A (en) | 1982-02-16 |
| PH15756A (en) | 1983-03-18 |
| JPS5610184A (en) | 1981-02-02 |
| SE8004976L (sv) | 1981-01-07 |
| NL8003879A (nl) | 1981-01-08 |
| DK290380A (da) | 1981-01-07 |
| ES8201019A1 (es) | 1981-11-01 |
| AT375077B (de) | 1984-06-25 |
| NZ194245A (en) | 1984-07-06 |
| FI802148A7 (fi) | 1981-01-01 |
| GR69327B (OSRAM) | 1982-05-17 |
| PT71500B (de) | 1981-12-11 |
| IT8023120A0 (it) | 1980-06-30 |
| BE884193A (fr) | 1981-01-05 |
| NO802014L (no) | 1981-01-07 |
| SE436747B (sv) | 1985-01-21 |
| FR2460950A1 (fr) | 1981-01-30 |
| YU174780A (en) | 1983-02-28 |
| AU536336B2 (en) | 1984-05-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |