HU203099B - Process for producing condensed quinolinium- and isoquinolinium derivatives and pharmaceutical compositions containing them - Google Patents
Process for producing condensed quinolinium- and isoquinolinium derivatives and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HU203099B HU203099B HU874436A HU443687A HU203099B HU 203099 B HU203099 B HU 203099B HU 874436 A HU874436 A HU 874436A HU 443687 A HU443687 A HU 443687A HU 203099 B HU203099 B HU 203099B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- triazino
- compound
- defined above
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 47
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- ZSVHUITUMSDFCK-UHFFFAOYSA-N isoquinoline;quinoline Chemical class C1=NC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 ZSVHUITUMSDFCK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 238000002360 preparation method Methods 0.000 claims abstract description 82
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 120
- -1 oxo compound Chemical class 0.000 claims description 49
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical class C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 45
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 23
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [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 15
- 239000000203 mixture Substances 0.000 claims description 14
- 150000001450 anions Chemical class 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 150000001449 anionic compounds Chemical class 0.000 claims description 7
- 150000002891 organic anions Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 230000029936 alkylation Effects 0.000 claims description 6
- 125000005594 diketone group Chemical group 0.000 claims description 6
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 5
- 150000002390 heteroarenes Chemical class 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 abstract description 5
- 239000003589 local anesthetic agent Substances 0.000 abstract description 5
- 230000000202 analgesic effect Effects 0.000 abstract description 4
- 239000000935 antidepressant agent Substances 0.000 abstract description 4
- 229940005513 antidepressants Drugs 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 239000000050 smooth muscle relaxant Substances 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 35
- 239000002244 precipitate Substances 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- XDRQUYSQQDJVAW-UHFFFAOYSA-N C(C)S(=O)(=O)[O-].C1=[NH+]C=CC2=CC=CC=C12 Chemical compound C(C)S(=O)(=O)[O-].C1=[NH+]C=CC2=CC=CC=C12 XDRQUYSQQDJVAW-UHFFFAOYSA-N 0.000 description 23
- KLJOVDQWQVYFFR-UHFFFAOYSA-N perchloric acid;quinoline Chemical compound [O-]Cl(=O)(=O)=O.[NH+]1=CC=CC2=CC=CC=C21 KLJOVDQWQVYFFR-UHFFFAOYSA-N 0.000 description 23
- 239000007858 starting material Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000013078 crystal Substances 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- 239000005457 ice water Substances 0.000 description 10
- IFSTXIFJFABXJL-UHFFFAOYSA-N isoquinoline;perchloric acid Chemical compound [O-]Cl(=O)(=O)=O.C1=[NH+]C=CC2=CC=CC=C21 IFSTXIFJFABXJL-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 231100001274 therapeutic index Toxicity 0.000 description 8
- 241000699666 Mus <mouse, genus> Species 0.000 description 7
- GYRVPKXEKRPIGJ-UHFFFAOYSA-N ethanesulfonate;quinolin-1-ium Chemical compound CCS([O-])(=O)=O.[NH+]1=CC=CC2=CC=CC=C21 GYRVPKXEKRPIGJ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 5
- 206010015995 Eyelid ptosis Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 201000003004 ptosis Diseases 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229960005333 tetrabenazine Drugs 0.000 description 5
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 4
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002178 crystalline material Substances 0.000 description 4
- 229960004194 lidocaine Drugs 0.000 description 4
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 4
- 229960003147 reserpine Drugs 0.000 description 4
- 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 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 3
- 229960000836 amitriptyline Drugs 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- JKKHUNQXHNZFFL-UHFFFAOYSA-M ethanesulfonate;tetrabutylazanium Chemical compound CCS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC JKKHUNQXHNZFFL-UHFFFAOYSA-M 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- FVXQITVSRLUPLD-UHFFFAOYSA-N isoquinolin-2-ium-1,2-diamine;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=C2C(N)=[N+](N)C=CC2=C1 FVXQITVSRLUPLD-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 2
- 229960002456 hexobarbital Drugs 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000003533 narcotic effect Effects 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
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- 210000002460 smooth muscle Anatomy 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- WVGMJQNJTWAARQ-UHFFFAOYSA-N 1-aminoquinolin-2-one Chemical compound C1=CC=C2C=CC(=O)N(N)C2=C1 WVGMJQNJTWAARQ-UHFFFAOYSA-N 0.000 description 1
- NGXSHCKRGQPHDL-UHFFFAOYSA-N 2,4-dihydro-1h-quinolin-3-one Chemical compound C1=CC=C2CC(=O)CNC2=C1 NGXSHCKRGQPHDL-UHFFFAOYSA-N 0.000 description 1
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- YQBLQKZERMAVDO-UHFFFAOYSA-N 2-oxo-2-phenylacetaldehyde;hydrate Chemical compound O.O=CC(=O)C1=CC=CC=C1 YQBLQKZERMAVDO-UHFFFAOYSA-N 0.000 description 1
- KDVFRMMRZOCFLS-UHFFFAOYSA-N 2-oxopentanoic acid Chemical compound CCCC(=O)C(O)=O KDVFRMMRZOCFLS-UHFFFAOYSA-N 0.000 description 1
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- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000003257 anti-anginal effect Effects 0.000 description 1
- 230000000539 anti-peristaltic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 230000003594 anti-tremorine Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- QKLCQKPAECHXCQ-UHFFFAOYSA-N ethyl phenylglyoxylate Chemical compound CCOC(=O)C(=O)C1=CC=CC=C1 QKLCQKPAECHXCQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- SHLPPXXKRFINFY-UHFFFAOYSA-N isoquinolin-2-ium;bromide Chemical compound Br.C1=NC=CC2=CC=CC=C21 SHLPPXXKRFINFY-UHFFFAOYSA-N 0.000 description 1
- PNVXLEZHGVTRFM-UHFFFAOYSA-N isoquinoline;sulfuric acid Chemical compound OS(O)(=O)=O.C1=NC=CC2=CC=CC=C21 PNVXLEZHGVTRFM-UHFFFAOYSA-N 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 238000007280 thionation reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU874436A HU203099B (en) | 1987-10-02 | 1987-10-02 | Process for producing condensed quinolinium- and isoquinolinium derivatives and pharmaceutical compositions containing them |
| CH3626/88A CH676847A5 (en, 2012) | 1987-10-02 | 1988-09-29 | |
| IL87875A IL87875A0 (en) | 1987-10-02 | 1988-09-29 | Condensed quinolinium and isoquinolinium derivatives,their preparation and pharmaceutical compositions containing them |
| YU01822/88A YU182288A (en) | 1987-10-02 | 1988-09-29 | Process for obtaining condensed quinolinium and izoquinolinium derivatives |
| US07/251,445 US4994448A (en) | 1987-10-02 | 1988-09-30 | Condensed quinolinium and isoquinolinium derivatives |
| GR880100650A GR880100650A (el) | 1987-10-02 | 1988-09-30 | Μεθοδος παρασκευης νεων συμπυκνωμενων παραγωγων κινολινιου & ισοκινολινιου |
| SE8803484A SE8803484L (sv) | 1987-10-02 | 1988-09-30 | Nya kinolin- och isokinolinderivat och foerfarande foer framstaellning daerav |
| FR888812801A FR2621314B1 (fr) | 1987-10-02 | 1988-09-30 | Nouveaux derives de quinoleinium et d'isoquinoleinium, procede pour leur preparation et compositions pharmaceutiques les contenant |
| NL8802405A NL8802405A (nl) | 1987-10-02 | 1988-09-30 | Gecondenseerde chinolinium en isochinoliniumderivaten. |
| BE8801118A BE1002518A4 (fr) | 1987-10-02 | 1988-09-30 | Nouveaux derives de quinoleinium et d'isoquinoleinium et procede pour leur preparation. |
| AU23345/88A AU608066B2 (en) | 1987-10-02 | 1988-09-30 | Condensed quinolinium and isoquinolinium derivatives |
| JP63244722A JPH01163178A (ja) | 1987-10-02 | 1988-09-30 | 縮合キノリニウム及びイソキノリニウム誘導体 |
| GB8823011A GB2210369B (en) | 1987-10-02 | 1988-09-30 | Condensed quinolinium and isoquinolinium derivatives |
| DD88320333A DD273632A5 (de) | 1987-10-02 | 1988-09-30 | Verfahren zur herstellung kondensierter chinolinium- und isochinolinium-derivate |
| DK549588A DK549588A (da) | 1987-10-02 | 1988-09-30 | Quinoliniumderivater |
| KR1019880012757A KR890006601A (ko) | 1987-10-02 | 1988-09-30 | 퀴놀리늄과 이소퀴놀리늄 유도체 및 그의 제조방법 |
| PL27498988A PL274989A1 (en) | 1987-10-02 | 1988-09-30 | Method of manufacture of new condensed derivatives of quinoline and isoquinoline |
| IT8822146A IT8822146A0 (it) | 1987-10-02 | 1988-09-30 | Derivati di chinolinio ed isochinolinio condensati |
| ES8803448A ES2012567A6 (es) | 1987-10-02 | 1988-09-30 | Procedimiento de preparacion de derivados de quinolinio e isoquinolinio condensados. |
| FI884535A FI884535A7 (fi) | 1987-10-02 | 1988-09-30 | Foerfarande foer framstaellning av nya kinolinium- och isokinoliniumderivat. |
| DE3833615A DE3833615A1 (de) | 1987-10-02 | 1988-10-03 | As-triazino(2,3-a)chinolinium- beziehungsweise as-triazino(3,2-a)isochinoliniumderivate, verfahren und zwischenprodukte zu ihrer herstellung und die ersteren enthaltende arzneimittel |
| YU02155/89A YU215589A (en) | 1987-10-02 | 1989-11-13 | Process for obtaining condensed quinolinium and izoquinolinium derivatives |
| YU02156/89A YU215689A (en) | 1987-10-02 | 1989-11-13 | Process for obtaining condensed quinoline and izoquinoline derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU874436A HU203099B (en) | 1987-10-02 | 1987-10-02 | Process for producing condensed quinolinium- and isoquinolinium derivatives and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT48626A HUT48626A (en) | 1989-06-28 |
| HU203099B true HU203099B (en) | 1991-05-28 |
Family
ID=10967954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU874436A HU203099B (en) | 1987-10-02 | 1987-10-02 | Process for producing condensed quinolinium- and isoquinolinium derivatives and pharmaceutical compositions containing them |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4994448A (en, 2012) |
| JP (1) | JPH01163178A (en, 2012) |
| KR (1) | KR890006601A (en, 2012) |
| AU (1) | AU608066B2 (en, 2012) |
| BE (1) | BE1002518A4 (en, 2012) |
| CH (1) | CH676847A5 (en, 2012) |
| DD (1) | DD273632A5 (en, 2012) |
| DE (1) | DE3833615A1 (en, 2012) |
| DK (1) | DK549588A (en, 2012) |
| ES (1) | ES2012567A6 (en, 2012) |
| FI (1) | FI884535A7 (en, 2012) |
| FR (1) | FR2621314B1 (en, 2012) |
| GB (1) | GB2210369B (en, 2012) |
| GR (1) | GR880100650A (en, 2012) |
| HU (1) | HU203099B (en, 2012) |
| IL (1) | IL87875A0 (en, 2012) |
| IT (1) | IT8822146A0 (en, 2012) |
| NL (1) | NL8802405A (en, 2012) |
| PL (1) | PL274989A1 (en, 2012) |
| SE (1) | SE8803484L (en, 2012) |
| YU (3) | YU182288A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4753499B2 (ja) * | 2001-07-31 | 2011-08-24 | ホリゾン・インターナショナル株式会社 | コイル綴じ製本用表紙及びその表紙付コイル綴じ冊子 |
| CN109438439B (zh) * | 2018-10-08 | 2021-04-13 | 安徽大学 | 四氢异喹啉并1,2,4-三唑类衍生物及其制备方法 |
| US20230416209A1 (en) * | 2020-11-23 | 2023-12-28 | Health Research, Inc. | Compounds and methods to target glucose-stimulated phosphohistidine signaling and esophageal cancer growth |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR255086A (en, 2012) * | ||||
| HU187305B (en) * | 1980-07-18 | 1985-12-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing condensed as-triazine derivatives |
| HU190503B (en) * | 1983-09-20 | 1986-09-29 | Egyt Gyogyszervegyeszetei Gyar,Hu | Process for production of condensated as-triazine derivatives |
| HU190505B (en) * | 1983-09-20 | 1986-09-29 | Egis Gyogyszergyar,Hu | Process for preparing condensed as-triazine-derivatives of twin ion type |
| HU190504B (en) * | 1983-09-20 | 1986-09-29 | Egis Gyogyszergyar,Hu | Process for preparing condensed as-triazinium-derivatives |
-
1987
- 1987-10-02 HU HU874436A patent/HU203099B/hu not_active IP Right Cessation
-
1988
- 1988-09-29 IL IL87875A patent/IL87875A0/xx unknown
- 1988-09-29 CH CH3626/88A patent/CH676847A5/de not_active IP Right Cessation
- 1988-09-29 YU YU01822/88A patent/YU182288A/xx unknown
- 1988-09-30 DD DD88320333A patent/DD273632A5/de not_active IP Right Cessation
- 1988-09-30 AU AU23345/88A patent/AU608066B2/en not_active Ceased
- 1988-09-30 ES ES8803448A patent/ES2012567A6/es not_active Expired - Lifetime
- 1988-09-30 US US07/251,445 patent/US4994448A/en not_active Expired - Fee Related
- 1988-09-30 SE SE8803484A patent/SE8803484L/xx not_active Application Discontinuation
- 1988-09-30 PL PL27498988A patent/PL274989A1/xx unknown
- 1988-09-30 GR GR880100650A patent/GR880100650A/el unknown
- 1988-09-30 GB GB8823011A patent/GB2210369B/en not_active Expired - Lifetime
- 1988-09-30 BE BE8801118A patent/BE1002518A4/fr not_active IP Right Cessation
- 1988-09-30 IT IT8822146A patent/IT8822146A0/it unknown
- 1988-09-30 DK DK549588A patent/DK549588A/da not_active Application Discontinuation
- 1988-09-30 KR KR1019880012757A patent/KR890006601A/ko not_active Withdrawn
- 1988-09-30 FR FR888812801A patent/FR2621314B1/fr not_active Expired - Lifetime
- 1988-09-30 JP JP63244722A patent/JPH01163178A/ja active Pending
- 1988-09-30 FI FI884535A patent/FI884535A7/fi not_active Application Discontinuation
- 1988-09-30 NL NL8802405A patent/NL8802405A/nl not_active Application Discontinuation
- 1988-10-03 DE DE3833615A patent/DE3833615A1/de not_active Withdrawn
-
1989
- 1989-11-13 YU YU02155/89A patent/YU215589A/xx unknown
- 1989-11-13 YU YU02156/89A patent/YU215689A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL8802405A (nl) | 1989-05-01 |
| DK549588D0 (da) | 1988-09-30 |
| FR2621314B1 (fr) | 1990-10-26 |
| YU182288A (en) | 1990-04-30 |
| DD273632A5 (de) | 1989-11-22 |
| IT8822146A0 (it) | 1988-09-30 |
| YU215689A (en) | 1991-02-28 |
| GB2210369B (en) | 1991-03-20 |
| BE1002518A4 (fr) | 1991-03-12 |
| JPH01163178A (ja) | 1989-06-27 |
| HUT48626A (en) | 1989-06-28 |
| DK549588A (da) | 1989-04-03 |
| PL274989A1 (en) | 1989-05-02 |
| AU2334588A (en) | 1989-04-06 |
| FI884535A7 (fi) | 1989-04-03 |
| SE8803484D0 (sv) | 1988-09-30 |
| AU608066B2 (en) | 1991-03-21 |
| KR890006601A (ko) | 1989-06-14 |
| GR880100650A (el) | 1989-09-29 |
| FI884535A0 (fi) | 1988-09-30 |
| DE3833615A1 (de) | 1989-04-13 |
| GB2210369A (en) | 1989-06-07 |
| CH676847A5 (en, 2012) | 1991-03-15 |
| SE8803484L (sv) | 1989-04-03 |
| FR2621314A1 (fr) | 1989-04-07 |
| US4994448A (en) | 1991-02-19 |
| GB8823011D0 (en) | 1988-11-09 |
| ES2012567A6 (es) | 1990-04-01 |
| IL87875A0 (en) | 1989-03-31 |
| YU215589A (en) | 1990-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |