DD238793A5 - Verfahren zur herstellung von amin-derivaten des pyrazins - Google Patents
Verfahren zur herstellung von amin-derivaten des pyrazins Download PDFInfo
- Publication number
- DD238793A5 DD238793A5 DD84259545A DD25954584A DD238793A5 DD 238793 A5 DD238793 A5 DD 238793A5 DD 84259545 A DD84259545 A DD 84259545A DD 25954584 A DD25954584 A DD 25954584A DD 238793 A5 DD238793 A5 DD 238793A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- thienyl
- pyridazine
- acid
- formula
- derivatives
- Prior art date
Links
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 150000001412 amines Chemical class 0.000 claims description 8
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 abstract description 5
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical class ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 abstract description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 150000004892 pyridazines Chemical class 0.000 abstract description 2
- 150000001334 alicyclic compounds Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 206010015995 Eyelid ptosis Diseases 0.000 description 5
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 201000003004 ptosis Diseases 0.000 description 5
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound 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 5
- 229960003147 reserpine Drugs 0.000 description 5
- 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 5
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010028347 Muscle twitching Diseases 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- -1 amine derivatives of pyridazine Chemical class 0.000 description 4
- 230000036461 convulsion Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- 102000010909 Monoamine Oxidase Human genes 0.000 description 3
- 108010062431 Monoamine oxidase Proteins 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 210000001577 neostriatum Anatomy 0.000 description 3
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
- VPNGLLJBAXZKOA-UHFFFAOYSA-N 3-chloro-4-methyl-6-thiophen-2-ylpyridazine Chemical group N1=C(Cl)C(C)=CC(C=2SC=CC=2)=N1 VPNGLLJBAXZKOA-UHFFFAOYSA-N 0.000 description 2
- CMMUAXBNDNEYSF-UHFFFAOYSA-N 3-chloro-4-methyl-6-thiophen-3-ylpyridazine Chemical group N1=C(Cl)C(C)=CC(C2=CSC=C2)=N1 CMMUAXBNDNEYSF-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000003291 dopaminomimetic effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000003902 lesion Effects 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 description 2
- 235000011151 potassium sulphates Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AMGIFCXCVQRLNU-UHFFFAOYSA-N 2-(3-hydroxy-3-methylcyclohexyl)propanoic acid Chemical compound OC(=O)C(C)C1CCCC(C)(O)C1 AMGIFCXCVQRLNU-UHFFFAOYSA-N 0.000 description 1
- CQZTVVMHCHAVEG-UHFFFAOYSA-N 2-hydroxy-2-methyl-4-oxo-4-thiophen-2-ylbutanoic acid Chemical compound OC(=O)C(O)(C)CC(=O)C1=CC=CS1 CQZTVVMHCHAVEG-UHFFFAOYSA-N 0.000 description 1
- RNIDWJDZNNVFDY-UHFFFAOYSA-N 3-Acetylthiophene Chemical compound CC(=O)C=1C=CSC=1 RNIDWJDZNNVFDY-UHFFFAOYSA-N 0.000 description 1
- BBVXPJDXIWNCJV-UHFFFAOYSA-N 3-cyclohexyl-5-methyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=CC(C2CCCCC2)=N1 BBVXPJDXIWNCJV-UHFFFAOYSA-N 0.000 description 1
- OWNCAJBLUVKXDY-UHFFFAOYSA-N 4-methyl-n-(2-morpholin-4-ylethyl)-6-thiophen-3-ylpyridazin-3-amine Chemical compound CC1=CC(C2=CSC=C2)=NN=C1NCCN1CCOCC1 OWNCAJBLUVKXDY-UHFFFAOYSA-N 0.000 description 1
- VZRMTEYDZZKZDV-UHFFFAOYSA-N 5-methyl-3-thiophen-2-yl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=CC(C=2SC=CC=2)=N1 VZRMTEYDZZKZDV-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 102100028661 Amine oxidase [flavin-containing] A Human genes 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 108010009685 Cholinergic Receptors Proteins 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 101000694718 Homo sapiens Amine oxidase [flavin-containing] A Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 102000034337 acetylcholine receptors Human genes 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 210000001638 cerebellum Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 230000000718 cholinopositive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000003447 ipsilateral effect Effects 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- LDMWSLGGVTVJPG-UHFFFAOYSA-N minaprine Chemical compound CC1=CC(C=2C=CC=CC=2)=NN=C1NCCN1CCOCC1 LDMWSLGGVTVJPG-UHFFFAOYSA-N 0.000 description 1
- 229960004758 minaprine Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8301029A FR2539742B1 (fr) | 1983-01-24 | 1983-01-24 | Derives amines de la pyridazine substitues en position 6 par un heterocycle ou un alicycle, lesdits derives etant actifs sur le systeme nerveux central |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD238793A5 true DD238793A5 (de) | 1986-09-03 |
Family
ID=9285222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84259545A DD238793A5 (de) | 1983-01-24 | 1984-01-23 | Verfahren zur herstellung von amin-derivaten des pyrazins |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4524070A (cs) |
| EP (1) | EP0117171B1 (cs) |
| JP (1) | JPS59139367A (cs) |
| KR (1) | KR910000641B1 (cs) |
| AT (1) | ATE28077T1 (cs) |
| AU (1) | AU560542B2 (cs) |
| CA (1) | CA1218063A (cs) |
| CS (1) | CS241539B2 (cs) |
| DD (1) | DD238793A5 (cs) |
| DE (1) | DE3464491D1 (cs) |
| DK (1) | DK31584A (cs) |
| ES (1) | ES529007A0 (cs) |
| FI (1) | FI840268A7 (cs) |
| FR (1) | FR2539742B1 (cs) |
| GR (1) | GR81717B (cs) |
| HU (1) | HU192390B (cs) |
| IE (1) | IE840150L (cs) |
| IL (1) | IL70757A (cs) |
| NO (1) | NO840244L (cs) |
| NZ (1) | NZ206907A (cs) |
| PT (1) | PT77982B (cs) |
| SU (1) | SU1189345A3 (cs) |
| YU (1) | YU12384A (cs) |
| ZA (1) | ZA84501B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5141628A (en) * | 1987-08-19 | 1992-08-25 | Rwe-Entsorgung Aktiengesellschaft | Method of cleaning and regenerating used oils |
| US5656631A (en) * | 1989-02-07 | 1997-08-12 | Sanofi | Pyridazine derivatives |
| FR2665442B1 (fr) * | 1990-07-31 | 1992-12-04 | Sanofi Sa | Derives d'alkyl-6 pyridazine, procede de preparation et compositions pharmaceutiques en contenant. |
| US5461053A (en) * | 1989-02-07 | 1995-10-24 | Sanofi | Pyridazine derivatives |
| PT93060B (pt) | 1989-02-07 | 1995-12-29 | Sanofi Sa | Processo para a obtencao de derivados de piridazina e de composicoes farmaceuticas que os contem |
| AU2005260102A1 (en) * | 2004-05-08 | 2006-01-12 | Novartis International Pharmaceutical Ltd. | 3-aryl-5,6-disubstituted pyridazines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1292443A (en) * | 1968-11-01 | 1972-10-11 | Ct D Etudes Experimentales Et | New pyridazine derivatives and process for their preparation |
| GB1345880A (en) * | 1971-06-18 | 1974-02-06 | Cepbepe | Pyridazine derivatives |
-
1983
- 1983-01-24 FR FR8301029A patent/FR2539742B1/fr not_active Expired
-
1984
- 1984-01-18 AT AT84400102T patent/ATE28077T1/de active
- 1984-01-18 EP EP84400102A patent/EP0117171B1/fr not_active Expired
- 1984-01-18 US US06/571,698 patent/US4524070A/en not_active Expired - Fee Related
- 1984-01-18 DE DE8484400102T patent/DE3464491D1/de not_active Expired
- 1984-01-18 CA CA000445483A patent/CA1218063A/en not_active Expired
- 1984-01-19 ES ES529007A patent/ES529007A0/es active Granted
- 1984-01-20 NZ NZ206907A patent/NZ206907A/en unknown
- 1984-01-20 PT PT77982A patent/PT77982B/pt not_active IP Right Cessation
- 1984-01-23 SU SU843694357A patent/SU1189345A3/ru active
- 1984-01-23 KR KR1019840000274A patent/KR910000641B1/ko not_active Expired
- 1984-01-23 FI FI840268A patent/FI840268A7/fi not_active Application Discontinuation
- 1984-01-23 GR GR73585A patent/GR81717B/el unknown
- 1984-01-23 ZA ZA84501A patent/ZA84501B/xx unknown
- 1984-01-23 IL IL70757A patent/IL70757A/xx unknown
- 1984-01-23 NO NO840244A patent/NO840244L/no unknown
- 1984-01-23 IE IE840150A patent/IE840150L/xx unknown
- 1984-01-23 DD DD84259545A patent/DD238793A5/de unknown
- 1984-01-24 JP JP59010903A patent/JPS59139367A/ja active Pending
- 1984-01-24 CS CS84530A patent/CS241539B2/cs unknown
- 1984-01-24 YU YU00123/84A patent/YU12384A/xx unknown
- 1984-01-24 AU AU23727/84A patent/AU560542B2/en not_active Ceased
- 1984-01-24 DK DK31584A patent/DK31584A/da unknown
- 1984-01-24 HU HU84294A patent/HU192390B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE840150L (en) | 1984-07-24 |
| PT77982B (fr) | 1986-04-10 |
| NZ206907A (en) | 1987-03-31 |
| KR840007409A (ko) | 1984-12-07 |
| HU192390B (en) | 1987-06-29 |
| CS53084A2 (en) | 1985-07-16 |
| NO840244L (no) | 1984-07-25 |
| EP0117171B1 (fr) | 1987-07-01 |
| IL70757A0 (en) | 1984-04-30 |
| IL70757A (en) | 1986-12-31 |
| ZA84501B (en) | 1984-09-26 |
| KR910000641B1 (ko) | 1991-01-31 |
| FI840268A0 (fi) | 1984-01-23 |
| DK31584A (da) | 1984-07-25 |
| ES8407043A1 (es) | 1984-09-01 |
| CA1218063A (en) | 1987-02-17 |
| DK31584D0 (da) | 1984-01-24 |
| EP0117171A1 (fr) | 1984-08-29 |
| DE3464491D1 (en) | 1987-08-06 |
| FI840268A7 (fi) | 1984-07-25 |
| GR81717B (cs) | 1984-12-12 |
| ATE28077T1 (de) | 1987-07-15 |
| US4524070A (en) | 1985-06-18 |
| SU1189345A3 (ru) | 1985-10-30 |
| AU560542B2 (en) | 1987-04-09 |
| YU12384A (en) | 1986-10-31 |
| PT77982A (fr) | 1984-02-01 |
| AU2372784A (en) | 1984-07-26 |
| JPS59139367A (ja) | 1984-08-10 |
| FR2539742A1 (fr) | 1984-07-27 |
| FR2539742B1 (fr) | 1986-09-05 |
| CS241539B2 (en) | 1986-03-13 |
| ES529007A0 (es) | 1984-09-01 |
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