CH533123A - Verfahren zur Herstellung von Chinolinderivaten - Google Patents
Verfahren zur Herstellung von ChinolinderivatenInfo
- Publication number
- CH533123A CH533123A CH1402971A CH1402971A CH533123A CH 533123 A CH533123 A CH 533123A CH 1402971 A CH1402971 A CH 1402971A CH 1402971 A CH1402971 A CH 1402971A CH 533123 A CH533123 A CH 533123A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- ethyl
- dependent
- quinoline
- piperidyl
- Prior art date
Links
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 title abstract 4
- 235000001258 Cinchona calisaya Nutrition 0.000 title abstract 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 title abstract 2
- 229960000948 quinine Drugs 0.000 title abstract 2
- -1 methylene- dioxy Chemical group 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 7
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 150000003248 quinolines Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- BJGICVZPZVYOLR-LSDHHAIUSA-N 3-[(3r,4r)-1-chloro-3-ethylpiperidin-4-yl]-1-(6,7-dimethoxyquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(Cl)CC[C@H]1CCC(=O)C1=CC=NC2=CC(OC)=C(OC)C=C12 BJGICVZPZVYOLR-LSDHHAIUSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- WKWXJVSQCAAVPE-LSDHHAIUSA-N 3-[(3r,4r)-1-chloro-3-ethenylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one Chemical compound C12=CC(OC)=CC=C2N=CC=C1C(=O)CC[C@@H]1CCN(Cl)C[C@@H]1C=C WKWXJVSQCAAVPE-LSDHHAIUSA-N 0.000 claims description 2
- VMROKBJPEDVMPH-UONOGXRCSA-N 3-[(3r,4r)-1-chloro-3-ethenylpiperidin-4-yl]-1-(7-chloroquinolin-4-yl)propan-1-one Chemical compound C=C[C@H]1CN(Cl)CC[C@H]1CCC(=O)C1=CC=NC2=CC(Cl)=CC=C12 VMROKBJPEDVMPH-UONOGXRCSA-N 0.000 claims description 2
- AXNNWKDTYCMCPB-LSDHHAIUSA-N 3-[(3r,4r)-1-chloro-3-ethylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(Cl)CC[C@H]1CCC(=O)C1=CC=NC2=CC=C(OC)C=C12 AXNNWKDTYCMCPB-LSDHHAIUSA-N 0.000 claims description 2
- CBSRVASDHVWTPS-JKSUJKDBSA-N 3-[(3r,4r)-1-chloro-3-ethylpiperidin-4-yl]-1-(6-methylquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(Cl)CC[C@H]1CCC(=O)C1=CC=NC2=CC=C(C)C=C12 CBSRVASDHVWTPS-JKSUJKDBSA-N 0.000 claims description 2
- ZCBIAHANERSVKJ-UONOGXRCSA-N 3-[(3r,4r)-1-chloro-3-ethylpiperidin-4-yl]-1-(7-chloroquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(Cl)CC[C@H]1CCC(=O)C1=CC=NC2=CC(Cl)=CC=C12 ZCBIAHANERSVKJ-UONOGXRCSA-N 0.000 claims description 2
- ZJNGVGWQHVJIFV-LSDHHAIUSA-N 3-[(3r,4r)-1-chloro-3-ethylpiperidin-4-yl]-1-(7-methoxyquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(Cl)CC[C@H]1CCC(=O)C1=CC=NC2=CC(OC)=CC=C12 ZJNGVGWQHVJIFV-LSDHHAIUSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 14
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 2
- 230000000078 anti-malarial effect Effects 0.000 abstract description 2
- 239000003430 antimalarial agent Substances 0.000 abstract description 2
- 239000003638 chemical reducing agent Substances 0.000 abstract description 2
- 230000000707 stereoselective effect Effects 0.000 abstract description 2
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 229940033495 antimalarials Drugs 0.000 abstract 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 abstract 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 abstract 1
- 229910000071 diazene Inorganic materials 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 102
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 89
- 239000000243 solution Substances 0.000 description 86
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 239000000203 mixture Substances 0.000 description 76
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 description 17
- 239000007788 liquid Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000005708 Sodium hypochlorite Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000010828 elution Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YTWYJCFQNOZVEC-ZETCQYMHSA-N (2s)-2-piperidin-1-ylpropanoic acid Chemical compound OC(=O)[C@H](C)N1CCCCC1 YTWYJCFQNOZVEC-ZETCQYMHSA-N 0.000 description 5
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- YTWYJCFQNOZVEC-SSDOTTSWSA-N (2r)-2-piperidin-1-ylpropanoic acid Chemical class OC(=O)[C@@H](C)N1CCCCC1 YTWYJCFQNOZVEC-SSDOTTSWSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- SRFCUPVBYYAMIL-UHFFFAOYSA-N Quinidinon Natural products C1C(C(C2)C=C)CCN2C1C(=O)C1=CC=NC2=CC=C(OC)C=C21 SRFCUPVBYYAMIL-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- SRFCUPVBYYAMIL-CKFHNAJUSA-N [(2r,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanone Chemical compound C([C@H]([C@H](C1)C=C)C2)CN1[C@H]2C(=O)C1=CC=NC2=CC=C(OC)C=C21 SRFCUPVBYYAMIL-CKFHNAJUSA-N 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- VJVMBNUFZOTNFE-UHFFFAOYSA-N ethyl 7-methoxyquinoline-4-carboxylate Chemical compound COC1=CC=C2C(C(=O)OCC)=CC=NC2=C1 VJVMBNUFZOTNFE-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229940096017 silver fluoride Drugs 0.000 description 4
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- NTBIYBAYFBNTCD-KBPBESRZSA-N dibenzoyl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound O=C([C@@H](O)[C@H](O)C(=O)OC(=O)C=1C=CC=CC=1)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-KBPBESRZSA-N 0.000 description 3
- 238000011067 equilibration Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LJOQGZACKSYWCH-LHHVKLHASA-N (s)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol Chemical compound C1=C(OC)C=C2C([C@H](O)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 LJOQGZACKSYWCH-LHHVKLHASA-N 0.000 description 2
- JDQNYWYMNFRKNQ-UHFFFAOYSA-N 3-ethyl-4-methylpyridine Chemical compound CCC1=CN=CC=C1C JDQNYWYMNFRKNQ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- DKRSEIPLAZTSFD-UHFFFAOYSA-N d-quinotoxine Natural products C12=CC(OC)=CC=C2N=CC=C1C(=O)CCC1CCNCC1C=C DKRSEIPLAZTSFD-UHFFFAOYSA-N 0.000 description 2
- LJOQGZACKSYWCH-UHFFFAOYSA-N dihydro quinine Natural products C1=C(OC)C=C2C(C(O)C3CC4CCN3CC4CC)=CC=NC2=C1 LJOQGZACKSYWCH-UHFFFAOYSA-N 0.000 description 2
- GWMMXAJFIHZMJR-UHFFFAOYSA-N ethyl 6,7-dimethoxyquinoline-4-carboxylate Chemical compound COC=1C=C2C(=CC=NC2=CC1OC)C(=O)OCC GWMMXAJFIHZMJR-UHFFFAOYSA-N 0.000 description 2
- SKWBFZJHHKPNSX-UHFFFAOYSA-N ethyl 6-chloroquinoline-4-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OCC)=CC=NC2=C1 SKWBFZJHHKPNSX-UHFFFAOYSA-N 0.000 description 2
- OFGBYJPXRHRTPM-UHFFFAOYSA-N ethyl 6-methylquinoline-4-carboxylate Chemical compound C1=C(C)C=C2C(C(=O)OCC)=CC=NC2=C1 OFGBYJPXRHRTPM-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229960000811 hydroquinidine Drugs 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 150000003151 propanoic acid esters Chemical class 0.000 description 2
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DKRSEIPLAZTSFD-LSDHHAIUSA-N viquidil Chemical compound C12=CC(OC)=CC=C2N=CC=C1C(=O)CC[C@@H]1CCNC[C@@H]1C=C DKRSEIPLAZTSFD-LSDHHAIUSA-N 0.000 description 2
- 229960003353 viquidil Drugs 0.000 description 2
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- VVIBXFFNZABSJQ-LSDHHAIUSA-N 1-(6,7-dimethoxyquinolin-4-yl)-3-[(3r,4r)-3-ethylpiperidin-4-yl]propan-1-one Chemical compound CC[C@H]1CNCC[C@H]1CCC(=O)C1=CC=NC2=CC(OC)=C(OC)C=C12 VVIBXFFNZABSJQ-LSDHHAIUSA-N 0.000 description 1
- CNWZPVZWTAJHGY-HIFRSBDPSA-N 3-[(3R,4R)-1-benzoyl-3-(2-chloroethyl)piperidin-4-yl]propanoic acid Chemical class C1[C@H](CCCl)[C@H](CCC(=O)O)CCN1C(=O)C1=CC=CC=C1 CNWZPVZWTAJHGY-HIFRSBDPSA-N 0.000 description 1
- QSBNGAHNMYOKII-HIFRSBDPSA-N 3-[(3R,4R)-1-benzoyl-3-(2-iodoethyl)piperidin-4-yl]propanoic acid Chemical class C1[C@H](CCI)[C@H](CCC(=O)O)CCN1C(=O)C1=CC=CC=C1 QSBNGAHNMYOKII-HIFRSBDPSA-N 0.000 description 1
- YOBXWPBOYSYNOF-UONOGXRCSA-N 3-[(3r,4r)-1-chloro-3-ethylpiperidin-4-yl]-1-(6-chloroquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(Cl)CC[C@H]1CCC(=O)C1=CC=NC2=CC=C(Cl)C=C12 YOBXWPBOYSYNOF-UONOGXRCSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CMARBNQOJIBVQH-MNOVXSKESA-N C(C)OC(CC[C@@H]1[C@@H](CN(CC1)Cl)CC)=O Chemical compound C(C)OC(CC[C@@H]1[C@@H](CN(CC1)Cl)CC)=O CMARBNQOJIBVQH-MNOVXSKESA-N 0.000 description 1
- JUHACJRLIDHIIK-DTWKUNHWSA-N CC[C@@H](C1)[C@H](CCC(O)=O)CCN1Cl Chemical compound CC[C@@H](C1)[C@H](CCC(O)=O)CCN1Cl JUHACJRLIDHIIK-DTWKUNHWSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RNSXYRQCNALSEZ-UHFFFAOYSA-N [C].C1CCOC1 Chemical compound [C].C1CCOC1 RNSXYRQCNALSEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 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
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 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
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ITYAIFQYIIUEEY-VIFPVBQESA-N ethyl (2s)-2-piperidin-1-ylpropanoate Chemical compound CCOC(=O)[C@H](C)N1CCCCC1 ITYAIFQYIIUEEY-VIFPVBQESA-N 0.000 description 1
- CMARBNQOJIBVQH-WDEREUQCSA-N ethyl 3-[(3R,4R)-1-chloro-3-ethylpiperidin-4-yl]propanoate Chemical compound C(C)OC(CC[C@H]1[C@H](CN(CC1)Cl)CC)=O CMARBNQOJIBVQH-WDEREUQCSA-N 0.000 description 1
- OUNFNVMQTMVFLY-DOTOQJQBSA-N ethyl 3-[(3S,4S)-1-benzoyl-3-(2-chloroethyl)piperidin-4-yl]propanoate Chemical compound C(C)OC(CC[C@@H]1[C@@H](CN(CC1)C(C1=CC=CC=C1)=O)CCCl)=O OUNFNVMQTMVFLY-DOTOQJQBSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74191368A | 1968-07-02 | 1968-07-02 | |
| CH977369A CH521975A (de) | 1968-07-02 | 1969-06-26 | Verfahren zur Herstellung von Chinolinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH533123A true CH533123A (de) | 1973-01-31 |
Family
ID=24982727
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1402971A CH533123A (de) | 1968-07-02 | 1969-06-26 | Verfahren zur Herstellung von Chinolinderivaten |
| CH977369A CH521975A (de) | 1968-07-02 | 1969-06-26 | Verfahren zur Herstellung von Chinolinderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH977369A CH521975A (de) | 1968-07-02 | 1969-06-26 | Verfahren zur Herstellung von Chinolinderivaten |
Country Status (14)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2578579A1 (en) | 2010-07-14 | 2013-04-10 | National Institute of Immunology | Benzothiophene carboxamide compounds, composition and applications thereof |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH590275A5 (enrdf_load_stackoverflow) * | 1970-03-16 | 1977-07-29 | Hoffmann La Roche | |
| GB1441244A (en) * | 1972-11-17 | 1976-06-30 | Rech Et Dapplications Scient S | Derivatives of quinoline and method of preparing the same |
| NL7908031A (nl) * | 1979-11-01 | 1981-06-01 | Acf Chemiefarma Nv | Nieuwe chinolinederivaten en farmaceutische preparaten die een dergelijke verbinding bevatten, alsmede werk- wijze voor het bereiden van deze verbindingen. |
| FR2844270B1 (fr) | 2002-09-11 | 2006-05-19 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leur procede et intermediaires de preparation et les compositions qui les contiennent |
-
1969
- 1969-06-26 CH CH1402971A patent/CH533123A/de not_active IP Right Cessation
- 1969-06-26 CH CH977369A patent/CH521975A/de not_active IP Right Cessation
- 1969-07-01 FR FR6922135A patent/FR2012151A1/fr not_active Withdrawn
- 1969-07-01 AT AT626969A patent/AT319481B/de not_active IP Right Cessation
- 1969-07-01 BE BE735450D patent/BE735450A/xx not_active IP Right Cessation
- 1969-07-02 DK DK359169AA patent/DK136069B/da not_active IP Right Cessation
- 1969-07-02 GB GB33311/69A patent/GB1253741A/en not_active Expired
- 1969-07-02 IE IE903/69A patent/IE33474B1/xx unknown
- 1969-07-02 CA CA055,885A patent/CA956312A/en not_active Expired
- 1969-07-02 SE SE941269A patent/SE367823B/xx unknown
- 1969-07-02 NL NL6910144.A patent/NL166475C/xx not_active IP Right Cessation
- 1969-07-02 DE DE19691933599 patent/DE1933599A1/de not_active Ceased
- 1969-07-02 DE DE1967178A patent/DE1967178C2/de not_active Expired
- 1969-07-02 SE SE7206590A patent/SE375775B/xx unknown
- 1969-07-02 IL IL32534A patent/IL32534A/xx unknown
-
1971
- 1971-01-21 AT AT49171A patent/AT341115B/de not_active IP Right Cessation
- 1971-06-04 JP JP46039235A patent/JPS4915278B1/ja active Pending
- 1971-06-23 DK DK308971AA patent/DK136982B/da unknown
- 1971-11-01 CA CA126,551A patent/CA962682A/en not_active Expired
- 1971-12-16 PH PH13115A patent/PH12608A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2578579A1 (en) | 2010-07-14 | 2013-04-10 | National Institute of Immunology | Benzothiophene carboxamide compounds, composition and applications thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| IE33474L (en) | 1970-01-02 |
| NL6910144A (enrdf_load_stackoverflow) | 1970-01-06 |
| DK136982B (da) | 1977-12-27 |
| DE1967178C2 (de) | 1984-11-22 |
| IL32534A0 (en) | 1969-09-25 |
| NL166475B (nl) | 1981-03-16 |
| GB1253741A (en) | 1971-11-17 |
| FR2012151A1 (enrdf_load_stackoverflow) | 1970-03-13 |
| DK136982C (enrdf_load_stackoverflow) | 1978-07-10 |
| IL32534A (en) | 1975-07-28 |
| DK136069C (enrdf_load_stackoverflow) | 1978-01-16 |
| AT319481B (de) | 1974-12-27 |
| AT341115B (de) | 1978-01-25 |
| CA962682A (en) | 1975-02-11 |
| NL166475C (nl) | 1981-08-17 |
| DE1933599A1 (de) | 1970-02-26 |
| ATA49171A (de) | 1977-05-15 |
| SE375775B (enrdf_load_stackoverflow) | 1975-04-28 |
| IE33474B1 (en) | 1974-07-10 |
| CA956312A (en) | 1974-10-15 |
| JPS4915278B1 (enrdf_load_stackoverflow) | 1974-04-13 |
| SE367823B (enrdf_load_stackoverflow) | 1974-06-10 |
| CH521975A (de) | 1972-04-30 |
| PH12608A (en) | 1979-06-27 |
| BE735450A (enrdf_load_stackoverflow) | 1970-01-02 |
| DK136069B (da) | 1977-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |