SK72002A3 - Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition comprising same - Google Patents

Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition comprising same Download PDF

Info

Publication number: SK72002A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; solvates; physiologically acceptable; phenyl
Prior art date: 1999-07-10

Application number

SK7-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Rochus Jonas

Michael Wolf

Norbert Beier

Original Assignee

Merck Patent Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-07-10

Filing date

2000-06-27

Publication date

2002-05-09

2000-06-27 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2002-05-09 Publication of SK72002A3 publication Critical patent/SK72002A3/sk

Links

238000000034 method Methods 0.000 title claims description 8
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 7
VDWSVBMVZLRATD-UHFFFAOYSA-N phenyl(pyridazin-3-yl)methanone Chemical class C=1C=CN=NC=1C(=O)C1=CC=CC=C1 VDWSVBMVZLRATD-UHFFFAOYSA-N 0.000 title claims description 3
150000003839 salts Chemical class 0.000 claims abstract description 27
239000012453 solvate Substances 0.000 claims abstract description 21
238000006243 chemical reaction Methods 0.000 claims abstract description 18
206010006895 Cachexia Diseases 0.000 claims abstract description 8
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 7
206010040047 Sepsis Diseases 0.000 claims abstract description 7
208000006673 asthma Diseases 0.000 claims abstract description 7
208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
208000030507 AIDS Diseases 0.000 claims abstract description 6
206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 6
208000026935 allergic disease Diseases 0.000 claims abstract description 6
201000008937 atopic dermatitis Diseases 0.000 claims abstract description 6
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 6
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 6
206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 5
208000011231 Crohn disease Diseases 0.000 claims abstract description 5
206010027476 Metastases Diseases 0.000 claims abstract description 5
208000001132 Osteoporosis Diseases 0.000 claims abstract description 5
201000004681 Psoriasis Diseases 0.000 claims abstract description 5
206010052779 Transplant rejections Diseases 0.000 claims abstract description 5
201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 5
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
206010006458 Bronchitis chronic Diseases 0.000 claims abstract description 4
206010006451 bronchitis Diseases 0.000 claims abstract description 4
208000007451 chronic bronchitis Diseases 0.000 claims abstract description 4
208000017520 skin disease Diseases 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 86
229910052801 chlorine Inorganic materials 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
229910004013 NO 2 Inorganic materials 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
208000026139 Memory disease Diseases 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
230000009401 metastasis Effects 0.000 claims description 4
230000004614 tumor growth Effects 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 2
238000010306 acid treatment Methods 0.000 claims description 2
150000007514 bases Chemical class 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
TWZVLXFMQLLANO-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-4-[(4-nitrobenzoyl)amino]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=CC(NC(=O)C=4C=CC(=CC=4)[N+]([O-])=O)=CC=3)C=CC=2)=C1 TWZVLXFMQLLANO-UHFFFAOYSA-N 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 1
208000035475 disorder Diseases 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 abstract description 3
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 abstract description 3
230000001173 tumoral effect Effects 0.000 abstract 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
230000007547 defect Effects 0.000 abstract 1
208000013223 septicemia Diseases 0.000 abstract 1
-1 n-decyl Chemical group 0.000 description 55
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 9
239000002253 acid Substances 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000007858 starting material Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000003826 tablet Substances 0.000 description 6
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 4
USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000010422 painting Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 3
RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 3
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000000000 cycloalkoxy group Chemical group 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
102000003390 tumor necrosis factor Human genes 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000003086 colorant Substances 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000002674 ointment Substances 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
AKEZGUVOXRSZTO-UHFFFAOYSA-N 2,4-dichloro-n-[3-[[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamoyl]phenyl]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=C(NC(=O)C=4C(=CC(Cl)=CC=4)Cl)C=CC=3)C=CC=2)=C1 AKEZGUVOXRSZTO-UHFFFAOYSA-N 0.000 description 1
PACCSLWSSRHNFA-UHFFFAOYSA-N 2,4-dichloro-n-[4-[[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamoyl]phenyl]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=CC(NC(=O)C=4C(=CC(Cl)=CC=4)Cl)=CC=3)C=CC=2)=C1 PACCSLWSSRHNFA-UHFFFAOYSA-N 0.000 description 1
CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
HETVWNJEAWTHHK-UHFFFAOYSA-N 2,4-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C([N+]([O-])=O)=C1 HETVWNJEAWTHHK-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000005979 2-naphthyloxy group Chemical group 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 1
VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 description 1
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
XNZGNKJDTAKYKN-UHFFFAOYSA-N 3-[(3-chlorobenzoyl)amino]-n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=C(NC(=O)C=4C=C(Cl)C=CC=4)C=CC=3)C=CC=2)=C1 XNZGNKJDTAKYKN-UHFFFAOYSA-N 0.000 description 1
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NGULXOAWSLYEQV-UHFFFAOYSA-N 3-[(4-chlorobenzoyl)amino]-n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=C(NC(=O)C=4C=CC(Cl)=CC=4)C=CC=3)C=CC=2)=C1 NGULXOAWSLYEQV-UHFFFAOYSA-N 0.000 description 1
LFHHQPHFRUCKHR-UHFFFAOYSA-N 3-[(4-chlorobenzoyl)amino]-n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3C=C(NC(=O)C=4C=CC(Cl)=CC=4)C=CC=3)=CC=2)=C1 LFHHQPHFRUCKHR-UHFFFAOYSA-N 0.000 description 1
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IOOWNWWCLKMNSU-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-3-[(3-nitrobenzoyl)amino]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3C=C(NC(=O)C=4C=C(C=CC=4)[N+]([O-])=O)C=CC=3)=CC=2)=C1 IOOWNWWCLKMNSU-UHFFFAOYSA-N 0.000 description 1
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
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230000002265 prevention Effects 0.000 description 1
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QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
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238000001953 recrystallisation Methods 0.000 description 1
HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
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XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Oncology (AREA)
Diabetes (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Communicable Diseases (AREA)
Dermatology (AREA)
Virology (AREA)
Tropical Medicine & Parasitology (AREA)
Neurology (AREA)
Hematology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Biomedical Technology (AREA)
AIDS & HIV (AREA)
Neurosurgery (AREA)
Molecular Biology (AREA)
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Pain & Pain Management (AREA)
Transplantation (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
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SK7-2002A 1999-07-10 2000-06-27 Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition comprising same SK72002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19932315A DE19932315A1 (de)	1999-07-10	1999-07-10	Benzoylpyridazine
PCT/EP2000/005933 WO2001004099A1 (de)	1999-07-10	2000-06-27	Benzoylpyridazine

Publications (1)

Publication Number	Publication Date
SK72002A3 true SK72002A3 (en)	2002-05-09

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ID=7914352

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK7-2002A SK72002A3 (en)	1999-07-10	2000-06-27	Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition comprising same

Country Status (24)

Country	Link
US (1)	US6696446B1 (pl)
EP (1)	EP1194411B1 (pl)
JP (1)	JP2003504358A (pl)
KR (1)	KR20020019923A (pl)
CN (1)	CN1146545C (pl)
AR (1)	AR024672A1 (pl)
AT (1)	ATE269311T1 (pl)
AU (1)	AU763005B2 (pl)
BR (1)	BR0012328A (pl)
CA (1)	CA2378595A1 (pl)
CZ (1)	CZ200212A3 (pl)
DE (2)	DE19932315A1 (pl)
DK (1)	DK1194411T3 (pl)
ES (1)	ES2220513T3 (pl)
HK (1)	HK1048116A1 (pl)
HU (1)	HUP0201828A3 (pl)
MX (1)	MXPA02000317A (pl)
NO (1)	NO20020096D0 (pl)
PL (1)	PL353175A1 (pl)
PT (1)	PT1194411E (pl)
SI (1)	SI1194411T1 (pl)
SK (1)	SK72002A3 (pl)
WO (1)	WO2001004099A1 (pl)
ZA (1)	ZA200201087B (pl)

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Publication number	Priority date	Publication date	Assignee	Title
EP1368035A1 (en) *	2001-02-12	2003-12-10	MERCK PATENT GmbH	Use of type 4 phosphodiesterase inhibitors in myocardial diseases
MXPA04003668A (es) *	2001-10-31	2004-07-22	Merck Patent Gmbh	Inhibidores de fosfodiesteresa de tipo 4 y usos de los mismos.
PL369738A1 (pl)	2001-11-05	2005-05-02	Merck Patent Gmbh	Hydrazono-malonitryle
US9389796B1 (en) *	2015-02-23	2016-07-12	International Business Machines Corporation	Efficient register preservation on processors

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3704879A1 (de)	1987-02-17	1988-08-25	Merck Patent Gmbh	Pyridazinonderivate
DE19632549A1 (de)	1996-08-13	1998-02-19	Merck Patent Gmbh	Arylalkanoylpyridazine
DE19826841A1 (de) *	1998-06-16	1999-12-23	Merck Patent Gmbh	Arylalkanoylpyridazine

1999
- 1999-07-10 DE DE19932315A patent/DE19932315A1/de not_active Withdrawn
2000
- 2000-06-27 KR KR1020017015566A patent/KR20020019923A/ko not_active Ceased
- 2000-06-27 HK HK03100260.0A patent/HK1048116A1/zh unknown
- 2000-06-27 US US10/030,477 patent/US6696446B1/en not_active Expired - Fee Related
- 2000-06-27 PL PL00353175A patent/PL353175A1/pl unknown
- 2000-06-27 EP EP00954422A patent/EP1194411B1/de not_active Expired - Lifetime
- 2000-06-27 MX MXPA02000317A patent/MXPA02000317A/es active IP Right Grant
- 2000-06-27 DK DK00954422T patent/DK1194411T3/da active
- 2000-06-27 AT AT00954422T patent/ATE269311T1/de not_active IP Right Cessation
- 2000-06-27 PT PT00954422T patent/PT1194411E/pt unknown
- 2000-06-27 WO PCT/EP2000/005933 patent/WO2001004099A1/de not_active Ceased
- 2000-06-27 BR BRPI0012328-5A patent/BR0012328A/pt not_active IP Right Cessation
- 2000-06-27 CZ CZ200212A patent/CZ200212A3/cs unknown
- 2000-06-27 JP JP2001509710A patent/JP2003504358A/ja active Pending
- 2000-06-27 SI SI200030426T patent/SI1194411T1/xx unknown
- 2000-06-27 HU HU0201828A patent/HUP0201828A3/hu unknown
- 2000-06-27 CN CNB008100306A patent/CN1146545C/zh not_active Expired - Fee Related
- 2000-06-27 AU AU66883/00A patent/AU763005B2/en not_active Ceased
- 2000-06-27 ES ES00954422T patent/ES2220513T3/es not_active Expired - Lifetime
- 2000-06-27 DE DE50006829T patent/DE50006829D1/de not_active Expired - Fee Related
- 2000-06-27 SK SK7-2002A patent/SK72002A3/sk unknown
- 2000-06-27 CA CA002378595A patent/CA2378595A1/en not_active Abandoned
- 2000-07-07 AR ARP000103466A patent/AR024672A1/es not_active Application Discontinuation
2002
- 2002-01-09 NO NO20020096A patent/NO20020096D0/no not_active Application Discontinuation
- 2002-02-07 ZA ZA200201087A patent/ZA200201087B/en unknown

Also Published As

Publication number	Publication date
DE50006829D1 (de)	2004-07-22
EP1194411B1 (de)	2004-06-16
PL353175A1 (pl)	2003-11-03
NO20020096L (no)	2002-01-09
BR0012328A (pt)	2007-01-02
HK1048116A1 (zh)	2003-03-21
ATE269311T1 (de)	2004-07-15
SI1194411T1 (en)	2004-10-31
CA2378595A1 (en)	2001-01-18
CZ200212A3 (cs)	2002-04-17
DE19932315A1 (de)	2001-01-11
AU763005B2 (en)	2003-07-10
CN1360581A (zh)	2002-07-24
CN1146545C (zh)	2004-04-21
JP2003504358A (ja)	2003-02-04
ES2220513T3 (es)	2004-12-16
AR024672A1 (es)	2002-10-23
AU6688300A (en)	2001-01-30
DK1194411T3 (da)	2004-10-18
HUP0201828A2 (hu)	2002-12-28
KR20020019923A (ko)	2002-03-13
WO2001004099A1 (de)	2001-01-18
US6696446B1 (en)	2004-02-24
EP1194411A1 (de)	2002-04-10
MXPA02000317A (es)	2002-07-30
NO20020096D0 (no)	2002-01-09
PT1194411E (pt)	2004-11-30
ZA200201087B (en)	2003-07-30
HUP0201828A3 (en)	2003-02-28

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CZ291851B6 (cs)	2003-06-18	Derivát arylalkanoylpyridazinu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
PL190685B1 (pl)	2005-12-30	Nowe pochodne tetrazolu, środek farmaceutyczny oraz zastosowanie
SK5782001A3 (en)	2001-11-06	Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition containing same
JP2007500685A (ja)	2007-01-18	新規の６−フェニルフェナントリジン
AU763005B2 (en)	2003-07-10	Benzoylpyridazines
JP4198755B6 (ja)	2009-04-15	アリールアルカノイルピリダジン誘導体
MXPA00012592A (en)	2001-09-07	Aryl alkanoylpyridazines