CA2367051A1 - Utilisation d'arylalcanoylpyridazines - Google Patents
Utilisation d'arylalcanoylpyridazines Download PDFInfo
- Publication number
- CA2367051A1 CA2367051A1 CA002367051A CA2367051A CA2367051A1 CA 2367051 A1 CA2367051 A1 CA 2367051A1 CA 002367051 A CA002367051 A CA 002367051A CA 2367051 A CA2367051 A CA 2367051A CA 2367051 A1 CA2367051 A1 CA 2367051A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydropyridazine
- methoxyphenyl
- benzoyl
- carbonylamino
- pyridazine
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 7
- 208000030507 AIDS Diseases 0.000 claims abstract description 5
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 abstract 1
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract 1
- -1 methylenecyclopropyl Chemical group 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 238000002360 preparation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 125000000842 isoxazolyl group Chemical group 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- LIIAHUBAEAMYIF-UHFFFAOYSA-N (4-aminophenyl)-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(N)=CC=2)CCC1 LIIAHUBAEAMYIF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010012438 Dermatitis atopic Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 208000006673 asthma Diseases 0.000 description 3
- 201000008937 atopic dermatitis Diseases 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- PSOOLGWZIDQSCW-UHFFFAOYSA-N (2-aminophenyl)-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)N)CCC1 PSOOLGWZIDQSCW-UHFFFAOYSA-N 0.000 description 2
- YWXBTQYFJSXXIN-UHFFFAOYSA-N (3-aminophenyl)-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(N)C=CC=2)CCC1 YWXBTQYFJSXXIN-UHFFFAOYSA-N 0.000 description 2
- MMMSCVHAJVYWJL-UHFFFAOYSA-N (3-aminophenyl)-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(N)C=CC=2)C=C1OC1CCCC1 MMMSCVHAJVYWJL-UHFFFAOYSA-N 0.000 description 2
- WJYJIQCZORDKSE-UHFFFAOYSA-N (3-aminophenyl)-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(N)C=CC=2)=C1 WJYJIQCZORDKSE-UHFFFAOYSA-N 0.000 description 2
- OTWPKCFAMVFCEG-UHFFFAOYSA-N (4-aminophenyl)-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(N)=CC=2)C=C1OC1CCCC1 OTWPKCFAMVFCEG-UHFFFAOYSA-N 0.000 description 2
- PLSBERZNVIRBKE-UHFFFAOYSA-N (4-aminophenyl)-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(N)=CC=2)=C1 PLSBERZNVIRBKE-UHFFFAOYSA-N 0.000 description 2
- FFWHXOMXRWFLGV-UHFFFAOYSA-N (4-aminophenyl)-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(N)=CC=2)CCC1 FFWHXOMXRWFLGV-UHFFFAOYSA-N 0.000 description 2
- KFVCLUHRNKMMML-UHFFFAOYSA-N 2-(4-aminophenyl)-1-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)CC=2C=CC(N)=CC=2)CCC1 KFVCLUHRNKMMML-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 102000018594 Tumour necrosis factor Human genes 0.000 description 2
- 108050007852 Tumour necrosis factor Proteins 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010265 fast atom bombardment Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- UQNKTWFEVHSRNZ-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2C=NC=CC=2)CCC1 UQNKTWFEVHSRNZ-UHFFFAOYSA-N 0.000 description 2
- XONFRAAUOSFROR-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2C=CN=CC=2)CCC1 XONFRAAUOSFROR-UHFFFAOYSA-N 0.000 description 2
- RLSSHCRYYPLVOB-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)CCC1 RLSSHCRYYPLVOB-UHFFFAOYSA-N 0.000 description 2
- SKAJNAKRAXUINO-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3C=CN=CC=3)=CC=2)CCC1 SKAJNAKRAXUINO-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 2
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 230000000699 topical effect Effects 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HBSRBFZHPDAGEL-UHFFFAOYSA-N (4-aminophenyl)-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound C1=CC(N)=CC=C1C(=O)N1N=C(C=2C=C3OCOC3=CC=2)CCC1 HBSRBFZHPDAGEL-UHFFFAOYSA-N 0.000 description 1
- AKBMHHXENJLQOL-UHFFFAOYSA-N (4-aminophenyl)-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazin-2-yl]methanone Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(N)=CC=2)=C1 AKBMHHXENJLQOL-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DIKAUBKIDNXNNW-UHFFFAOYSA-N 1,1,1-triethoxypentane Chemical compound CCCCC(OCC)(OCC)OCC DIKAUBKIDNXNNW-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NASLINFISOTVJJ-UHFFFAOYSA-N 1,2-oxazole-5-carbonyl chloride Chemical compound ClC(=O)C1=CC=NO1 NASLINFISOTVJJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NOUDGPISLXECAJ-UHFFFAOYSA-N 1h-imidazole-5-carbonyl chloride Chemical compound ClC(=O)C1=CNC=N1 NOUDGPISLXECAJ-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- JTOMQXXKQNNQIM-UHFFFAOYSA-N 2,4-dimethyl-1,3-thiazole-5-carbonyl chloride Chemical compound CC1=NC(C)=C(C(Cl)=O)S1 JTOMQXXKQNNQIM-UHFFFAOYSA-N 0.000 description 1
- YZMBBJLCICTYLM-UHFFFAOYSA-N 2-(2-aminophenyl)-1-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)CC=2C(=CC=CC=2)N)CCC1 YZMBBJLCICTYLM-UHFFFAOYSA-N 0.000 description 1
- OSSDLVYZZRRFKO-UHFFFAOYSA-N 2-(3-aminophenyl)-1-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)CC=2C=C(N)C=CC=2)CCC1 OSSDLVYZZRRFKO-UHFFFAOYSA-N 0.000 description 1
- CUZVLXFAAWTQCU-UHFFFAOYSA-N 2-(3-aminophenyl)-1-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)CC=2C=C(N)C=CC=2)C=C1OC1CCCC1 CUZVLXFAAWTQCU-UHFFFAOYSA-N 0.000 description 1
- OUGSNOUVXGRRCT-UHFFFAOYSA-N 2-(3-aminophenyl)-1-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)CC=2C=C(N)C=CC=2)=C1 OUGSNOUVXGRRCT-UHFFFAOYSA-N 0.000 description 1
- VGVKNRXMLDVJQV-UHFFFAOYSA-N 2-(4-aminophenyl)-1-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound C1=CC(N)=CC=C1CC(=O)N1N=C(C=2C=C3OCOC3=CC=2)CCC1 VGVKNRXMLDVJQV-UHFFFAOYSA-N 0.000 description 1
- BGEBOODYSJZJLX-UHFFFAOYSA-N 2-(4-aminophenyl)-1-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)CC=2C=CC(N)=CC=2)C=C1OC1CCCC1 BGEBOODYSJZJLX-UHFFFAOYSA-N 0.000 description 1
- KLDHHJVQXGHXGC-UHFFFAOYSA-N 2-(4-aminophenyl)-1-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)CC=2C=CC(N)=CC=2)=C1 KLDHHJVQXGHXGC-UHFFFAOYSA-N 0.000 description 1
- MNFUSKCJBZFNER-UHFFFAOYSA-N 2-(4-aminophenyl)-1-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)CC=2C=CC(N)=CC=2)=C1 MNFUSKCJBZFNER-UHFFFAOYSA-N 0.000 description 1
- QNANQPDEDOGONY-UHFFFAOYSA-N 2-(4-aminophenyl)-1-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazin-2-yl]ethanone Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)CC=2C=CC(N)=CC=2)CCC1 QNANQPDEDOGONY-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- PAUYHIAYDSDBIU-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-1,4,5,6-tetrahydropyridazine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NNCCC1 PAUYHIAYDSDBIU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OYYQGBCCGQJUIO-UHFFFAOYSA-N 4-(pyridine-4-carbonylamino)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1NC(=O)C1=CC=NC=C1 OYYQGBCCGQJUIO-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- QMORNPYFTKKLHK-UHFFFAOYSA-N NC1=CC=C(C(=O)N2N=C(CCC2)C2=CC(=C(C=C2)S(=O)(=O)C)OC)C=C1.NC1=CC=C(C(=O)N2N=C(CCC2)C2=CC3=C(C=C2)OCO3)C=C1 Chemical compound NC1=CC=C(C(=O)N2N=C(CCC2)C2=CC(=C(C=C2)S(=O)(=O)C)OC)C=C1.NC1=CC=C(C(=O)N2N=C(CCC2)C2=CC3=C(C=C2)OCO3)C=C1 QMORNPYFTKKLHK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000012658 Skin autoimmune disease Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
- PNTUIMQZUGCMLI-UHFFFAOYSA-N [2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]-5-ethylphenyl]urea Chemical compound NC(=O)NC1=CC(CC)=CC=C1C(=O)N1N=C(C=2C=C(OC)C(OC)=CC=2)CCC1 PNTUIMQZUGCMLI-UHFFFAOYSA-N 0.000 description 1
- AOXNCGBBKGTMEE-UHFFFAOYSA-N [6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-(4-nitrophenyl)methanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)CCC1 AOXNCGBBKGTMEE-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- MKZRYHJQHATKLV-UHFFFAOYSA-N diazinan-1-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCCCN1 MKZRYHJQHATKLV-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GKIGETLDVAHOJG-UHFFFAOYSA-N ethyl n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC=C1C(=O)N1N=C(C=2C=C(OC)C(OC)=CC=2)CCC1 GKIGETLDVAHOJG-UHFFFAOYSA-N 0.000 description 1
- ZHPBSMNDJPBJSG-UHFFFAOYSA-N ethyl n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C(=O)N2N=C(CCC2)C=2C=C(OC)C(OC)=CC=2)=C1 ZHPBSMNDJPBJSG-UHFFFAOYSA-N 0.000 description 1
- VAMLGVJLRNMIKN-UHFFFAOYSA-N ethyl n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C(=O)N2N=C(CCC2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=C1 VAMLGVJLRNMIKN-UHFFFAOYSA-N 0.000 description 1
- GLYPRGIJDFVSAF-UHFFFAOYSA-N ethyl n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C(=O)N2N=C(CCC2)C=2C=C(OCC)C(OC)=CC=2)=C1 GLYPRGIJDFVSAF-UHFFFAOYSA-N 0.000 description 1
- NSGQBSCYMVJBTC-UHFFFAOYSA-N ethyl n-[4-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CC(=O)N1N=C(C=2C=C(OC)C(OC)=CC=2)CCC1 NSGQBSCYMVJBTC-UHFFFAOYSA-N 0.000 description 1
- JBOOVPMFKCFZJB-UHFFFAOYSA-N ethyl n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)N1N=C(C=2C=C(OC)C(OC)=CC=2)CCC1 JBOOVPMFKCFZJB-UHFFFAOYSA-N 0.000 description 1
- AKPJSFRKAAXLDC-UHFFFAOYSA-N ethyl n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)N1N=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)CCC1 AKPJSFRKAAXLDC-UHFFFAOYSA-N 0.000 description 1
- XZIQAKIJYXEIAQ-UHFFFAOYSA-N ethyl n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)N1N=C(C=2C=C(OCC)C(OC)=CC=2)CCC1 XZIQAKIJYXEIAQ-UHFFFAOYSA-N 0.000 description 1
- TZJIXHOCPSVRRY-UHFFFAOYSA-N ethyl n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)N1N=C(C=2C=C(OC)C(=CC=2)S(C)(=O)=O)CCC1 TZJIXHOCPSVRRY-UHFFFAOYSA-N 0.000 description 1
- CEHHNSHUODDYSI-UHFFFAOYSA-N ethyl n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)N1N=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)CCC1 CEHHNSHUODDYSI-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- DXMZKDGCMHVIOY-UHFFFAOYSA-N methyl n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC=C1C(=O)N1N=C(C=2C=C(OC)C(OC)=CC=2)CCC1 DXMZKDGCMHVIOY-UHFFFAOYSA-N 0.000 description 1
- UHQUYIZETNWTPY-UHFFFAOYSA-N methyl n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C(=O)N2N=C(CCC2)C=2C=C(OC)C(OC)=CC=2)=C1 UHQUYIZETNWTPY-UHFFFAOYSA-N 0.000 description 1
- BVQAHSQZNZGDCG-UHFFFAOYSA-N methyl n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C(=O)N2N=C(CCC2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=C1 BVQAHSQZNZGDCG-UHFFFAOYSA-N 0.000 description 1
- FRBUKNPSPAOYPE-UHFFFAOYSA-N methyl n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)OC)C=CC=2)=C1 FRBUKNPSPAOYPE-UHFFFAOYSA-N 0.000 description 1
- UPQJWUAFVRWDJM-UHFFFAOYSA-N methyl n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(=O)N1N=C(C=2C=C3OCOC3=CC=2)CCC1 UPQJWUAFVRWDJM-UHFFFAOYSA-N 0.000 description 1
- IBFVVGPHIPDSPN-UHFFFAOYSA-N methyl n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(=O)N1N=C(C=2C=C(OC)C(OC)=CC=2)CCC1 IBFVVGPHIPDSPN-UHFFFAOYSA-N 0.000 description 1
- NCRQKUUQMKVMGF-UHFFFAOYSA-N methyl n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(=O)N1N=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)CCC1 NCRQKUUQMKVMGF-UHFFFAOYSA-N 0.000 description 1
- FZDZSBCHUPMPIL-UHFFFAOYSA-N methyl n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)OC)=CC=2)=C1 FZDZSBCHUPMPIL-UHFFFAOYSA-N 0.000 description 1
- QNAQQPCPBLFWSK-UHFFFAOYSA-N methyl n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(=O)N1N=C(C=2C=C(OC)C(=CC=2)S(C)(=O)=O)CCC1 QNAQQPCPBLFWSK-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- DKYOGOXHBZXTJW-UHFFFAOYSA-N n-[2-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)CC=2C(=CC=CC=2)NC(=O)C=2C=NC=CC=2)CCC1 DKYOGOXHBZXTJW-UHFFFAOYSA-N 0.000 description 1
- AEDUPPJCIRANGO-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2ON=CC=2)CCC1 AEDUPPJCIRANGO-UHFFFAOYSA-N 0.000 description 1
- ZLQAMIVWNMOEKC-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2NC=NC=2)CCC1 ZLQAMIVWNMOEKC-UHFFFAOYSA-N 0.000 description 1
- RMAXTLXWBQVAMX-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C2=C(N=C(C)S2)C)CCC1 RMAXTLXWBQVAMX-UHFFFAOYSA-N 0.000 description 1
- IPJLDLQUTUZBMZ-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(C)=O)CCC1 IPJLDLQUTUZBMZ-UHFFFAOYSA-N 0.000 description 1
- OVNWPXXEJVOHNN-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2OC=CC=2)CCC1 OVNWPXXEJVOHNN-UHFFFAOYSA-N 0.000 description 1
- VRJBXKGOCZBYAG-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2N=CC=NC=2)CCC1 VRJBXKGOCZBYAG-UHFFFAOYSA-N 0.000 description 1
- YJDLLXGLGNAOMI-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2N=CC=CC=2)CCC1 YJDLLXGLGNAOMI-UHFFFAOYSA-N 0.000 description 1
- WDJLDKDQLDCOQT-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2N=CC=CN=2)CCC1 WDJLDKDQLDCOQT-UHFFFAOYSA-N 0.000 description 1
- WFBWQEXBWJLJSL-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2N=CN=CC=2)CCC1 WFBWQEXBWJLJSL-UHFFFAOYSA-N 0.000 description 1
- SHJBTADQFFXZOH-UHFFFAOYSA-N n-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C(=CC=CC=2)NC(=O)C=2SC=CC=2)CCC1 SHJBTADQFFXZOH-UHFFFAOYSA-N 0.000 description 1
- FHGBBMUGNBUSPT-UHFFFAOYSA-N n-[2-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C(=CC=CC=2)NC(=O)C=2C=NC=CC=2)C=C1OC1CCCC1 FHGBBMUGNBUSPT-UHFFFAOYSA-N 0.000 description 1
- IHTSUYMYXYJGNM-UHFFFAOYSA-N n-[2-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C(=CC=CC=2)NC(=O)C=2C=CN=CC=2)C=C1OC1CCCC1 IHTSUYMYXYJGNM-UHFFFAOYSA-N 0.000 description 1
- DHAQEXQRWLRABB-UHFFFAOYSA-N n-[2-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C(=CC=CC=2)NC(=O)C=2C=NC=CC=2)=C1 DHAQEXQRWLRABB-UHFFFAOYSA-N 0.000 description 1
- DPJFYCYENBYTRU-UHFFFAOYSA-N n-[2-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C(=CC=CC=2)NC(=O)C=2C=CN=CC=2)=C1 DPJFYCYENBYTRU-UHFFFAOYSA-N 0.000 description 1
- MDXMFJABWGIBSZ-UHFFFAOYSA-N n-[2-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C(=CC=CC=2)NC(=O)C=2C=CN=CC=2)=C1 MDXMFJABWGIBSZ-UHFFFAOYSA-N 0.000 description 1
- OTRLUSKTPUYIDV-UHFFFAOYSA-N n-[3-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)CC=2C=C(NC(=O)C=3C=NC=CC=3)C=CC=2)CCC1 OTRLUSKTPUYIDV-UHFFFAOYSA-N 0.000 description 1
- XGKVIZFVGASOSK-UHFFFAOYSA-N n-[3-[2-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)CC=2C=C(NC(=O)C=3C=NC=CC=3)C=CC=2)C=C1OC1CCCC1 XGKVIZFVGASOSK-UHFFFAOYSA-N 0.000 description 1
- MPPGDKGTWYSJND-UHFFFAOYSA-N n-[3-[2-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)CC=2C=C(NC(=O)C=3C=NC=CC=3)C=CC=2)=C1 MPPGDKGTWYSJND-UHFFFAOYSA-N 0.000 description 1
- OYTYETJYALERSR-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3ON=CC=3)C=CC=2)CCC1 OYTYETJYALERSR-UHFFFAOYSA-N 0.000 description 1
- HBKNHPKCNFOOSU-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3NC=NC=3)C=CC=2)CCC1 HBKNHPKCNFOOSU-UHFFFAOYSA-N 0.000 description 1
- GJSRUDOSVRVLEB-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C3=C(N=C(C)S3)C)C=CC=2)CCC1 GJSRUDOSVRVLEB-UHFFFAOYSA-N 0.000 description 1
- MWNYMOMOUOUOPX-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(C)=O)C=CC=2)CCC1 MWNYMOMOUOUOPX-UHFFFAOYSA-N 0.000 description 1
- CZWZJXHRYBZBDL-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3OC=CC=3)C=CC=2)CCC1 CZWZJXHRYBZBDL-UHFFFAOYSA-N 0.000 description 1
- FMHABHMWHMUEHH-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3N=CC=NC=3)C=CC=2)CCC1 FMHABHMWHMUEHH-UHFFFAOYSA-N 0.000 description 1
- PZGBOJRCOAPLAM-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3C=NC=CC=3)C=CC=2)CCC1 PZGBOJRCOAPLAM-UHFFFAOYSA-N 0.000 description 1
- JMDRAHLEWUQYRH-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3C=CN=CC=3)C=CC=2)CCC1 JMDRAHLEWUQYRH-UHFFFAOYSA-N 0.000 description 1
- HZKIUNHYDIOWIO-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3N=CC=CN=3)C=CC=2)CCC1 HZKIUNHYDIOWIO-UHFFFAOYSA-N 0.000 description 1
- ZNEMKPOYWHKKJD-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3N=CN=CC=3)C=CC=2)CCC1 ZNEMKPOYWHKKJD-UHFFFAOYSA-N 0.000 description 1
- VWNDJGZAXMSCGR-UHFFFAOYSA-N n-[3-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=C(NC(=O)C=3SC=CC=3)C=CC=2)CCC1 VWNDJGZAXMSCGR-UHFFFAOYSA-N 0.000 description 1
- OBEYYQJYXHBPER-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3ON=CC=3)C=CC=2)C=C1OC1CCCC1 OBEYYQJYXHBPER-UHFFFAOYSA-N 0.000 description 1
- UQPIUAQFGYWUMV-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3N=CNC=3)C=CC=2)C=C1OC1CCCC1 UQPIUAQFGYWUMV-UHFFFAOYSA-N 0.000 description 1
- CSSBTAPNLARNIR-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C3=C(N=C(C)S3)C)C=CC=2)C=C1OC1CCCC1 CSSBTAPNLARNIR-UHFFFAOYSA-N 0.000 description 1
- ZOAVSYHOXCMYTK-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(C)=O)C=CC=2)C=C1OC1CCCC1 ZOAVSYHOXCMYTK-UHFFFAOYSA-N 0.000 description 1
- WQIBIFPHYRDGDB-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3OC=CC=3)C=CC=2)C=C1OC1CCCC1 WQIBIFPHYRDGDB-UHFFFAOYSA-N 0.000 description 1
- YCHYBGWGMCZLFD-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3N=CC=NC=3)C=CC=2)C=C1OC1CCCC1 YCHYBGWGMCZLFD-UHFFFAOYSA-N 0.000 description 1
- OQIQVDDILAXSSO-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=NC=CC=3)C=CC=2)C=C1OC1CCCC1 OQIQVDDILAXSSO-UHFFFAOYSA-N 0.000 description 1
- HBOBDXDXVGVKRZ-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=CN=CC=3)C=CC=2)C=C1OC1CCCC1 HBOBDXDXVGVKRZ-UHFFFAOYSA-N 0.000 description 1
- LYGQICVKJZALHK-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3N=CC=CN=3)C=CC=2)C=C1OC1CCCC1 LYGQICVKJZALHK-UHFFFAOYSA-N 0.000 description 1
- NDIDHFYVJOHCSC-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3N=CN=CC=3)C=CC=2)C=C1OC1CCCC1 NDIDHFYVJOHCSC-UHFFFAOYSA-N 0.000 description 1
- TTZRFMBYTBUOIR-UHFFFAOYSA-N n-[3-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3SC=CC=3)C=CC=2)C=C1OC1CCCC1 TTZRFMBYTBUOIR-UHFFFAOYSA-N 0.000 description 1
- MCGNFKYGPJIKLY-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3ON=CC=3)C=CC=2)=C1 MCGNFKYGPJIKLY-UHFFFAOYSA-N 0.000 description 1
- WPOYAOHQKVHTQG-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3N=CNC=3)C=CC=2)=C1 WPOYAOHQKVHTQG-UHFFFAOYSA-N 0.000 description 1
- XHMYZIBXJZPBNF-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C3=C(N=C(C)S3)C)C=CC=2)=C1 XHMYZIBXJZPBNF-UHFFFAOYSA-N 0.000 description 1
- ITRLATXNCLRFSQ-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(C)=O)C=CC=2)=C1 ITRLATXNCLRFSQ-UHFFFAOYSA-N 0.000 description 1
- WIAWHJQTPUOQEJ-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3OC=CC=3)C=CC=2)=C1 WIAWHJQTPUOQEJ-UHFFFAOYSA-N 0.000 description 1
- GFZDJGKCNCNDPU-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3N=CC=NC=3)C=CC=2)=C1 GFZDJGKCNCNDPU-UHFFFAOYSA-N 0.000 description 1
- XZJFAIFBVFFNTF-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=NC=CC=3)C=CC=2)=C1 XZJFAIFBVFFNTF-UHFFFAOYSA-N 0.000 description 1
- UQQZPXUQNXTAFF-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3C=CN=CC=3)C=CC=2)=C1 UQQZPXUQNXTAFF-UHFFFAOYSA-N 0.000 description 1
- GMRZYDNWROZZMN-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3N=CC=CN=3)C=CC=2)=C1 GMRZYDNWROZZMN-UHFFFAOYSA-N 0.000 description 1
- JCNSIYJSFUQDRE-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3N=CN=CC=3)C=CC=2)=C1 JCNSIYJSFUQDRE-UHFFFAOYSA-N 0.000 description 1
- SMLBOFVOVARETK-UHFFFAOYSA-N n-[3-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=C(NC(=O)C=3SC=CC=3)C=CC=2)=C1 SMLBOFVOVARETK-UHFFFAOYSA-N 0.000 description 1
- OHCAVRGWQXWLRT-UHFFFAOYSA-N n-[4-[2-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound C1CCC(C=2C=C3OCOC3=CC=2)=NN1C(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 OHCAVRGWQXWLRT-UHFFFAOYSA-N 0.000 description 1
- PNUMBPCHDBYVSI-UHFFFAOYSA-N n-[4-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)CC=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)CCC1 PNUMBPCHDBYVSI-UHFFFAOYSA-N 0.000 description 1
- IYYYTIXTZZUVNQ-UHFFFAOYSA-N n-[4-[2-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)CC=2C=CC(NC(=O)C=3C=CN=CC=3)=CC=2)CCC1 IYYYTIXTZZUVNQ-UHFFFAOYSA-N 0.000 description 1
- WRPMSLVQPVPZSG-UHFFFAOYSA-N n-[4-[2-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)CC=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)C=C1OC1CCCC1 WRPMSLVQPVPZSG-UHFFFAOYSA-N 0.000 description 1
- QKJBEPRDFSOGFF-UHFFFAOYSA-N n-[4-[2-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)CC=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)=C1 QKJBEPRDFSOGFF-UHFFFAOYSA-N 0.000 description 1
- MVYXZPWOGWDJFD-UHFFFAOYSA-N n-[4-[2-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)CC=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)=C1 MVYXZPWOGWDJFD-UHFFFAOYSA-N 0.000 description 1
- WFCSSXBPTKLBCC-UHFFFAOYSA-N n-[4-[2-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazin-2-yl]-2-oxoethyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)CC=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)CCC1 WFCSSXBPTKLBCC-UHFFFAOYSA-N 0.000 description 1
- QYSIWVXKNJUFPC-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C=1C=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CC=NO1 QYSIWVXKNJUFPC-UHFFFAOYSA-N 0.000 description 1
- PBQMAMMOFXUARZ-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C=1C=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CNC=N1 PBQMAMMOFXUARZ-UHFFFAOYSA-N 0.000 description 1
- GLPZNHXVHAOYDW-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C)=C1C(=O)NC1=CC=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=C1 GLPZNHXVHAOYDW-UHFFFAOYSA-N 0.000 description 1
- BEHBUVWIFSZEFI-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)N1N=C(C=2C=C3OCOC3=CC=2)CCC1 BEHBUVWIFSZEFI-UHFFFAOYSA-N 0.000 description 1
- RYEUDQZLNIUDBU-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound C=1C=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CC=CO1 RYEUDQZLNIUDBU-UHFFFAOYSA-N 0.000 description 1
- UZDBQRQYKRVDLZ-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound C=1C=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CN=CC=N1 UZDBQRQYKRVDLZ-UHFFFAOYSA-N 0.000 description 1
- YUFUYYSIKNKGEQ-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CC=CN=C1 YUFUYYSIKNKGEQ-UHFFFAOYSA-N 0.000 description 1
- BEFGRAOTBSHKOG-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound C=1C=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=NC=CC=N1 BEFGRAOTBSHKOG-UHFFFAOYSA-N 0.000 description 1
- ZUMQKDTWPNXUFK-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound C=1C=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CC=NC=N1 ZUMQKDTWPNXUFK-UHFFFAOYSA-N 0.000 description 1
- WPKYASLBZORLOR-UHFFFAOYSA-N n-[4-[6-(1,3-benzodioxol-5-yl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)N2N=C(CCC2)C=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CC=CS1 WPKYASLBZORLOR-UHFFFAOYSA-N 0.000 description 1
- MIYCJYNAPGGAEV-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3ON=CC=3)=CC=2)CCC1 MIYCJYNAPGGAEV-UHFFFAOYSA-N 0.000 description 1
- PCBSJXSWUNFEAW-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3NC=NC=3)=CC=2)CCC1 PCBSJXSWUNFEAW-UHFFFAOYSA-N 0.000 description 1
- MYYJGKXLXKWTHB-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C3=C(N=C(C)S3)C)=CC=2)CCC1 MYYJGKXLXKWTHB-UHFFFAOYSA-N 0.000 description 1
- IJJBJNLARIXCQR-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(C)=O)=CC=2)CCC1 IJJBJNLARIXCQR-UHFFFAOYSA-N 0.000 description 1
- WDVQJZBKLVQRFJ-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)CCC1 WDVQJZBKLVQRFJ-UHFFFAOYSA-N 0.000 description 1
- JQADVWXRFVQNQJ-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3N=CC=NC=3)=CC=2)CCC1 JQADVWXRFVQNQJ-UHFFFAOYSA-N 0.000 description 1
- ZCYDINFDQPIOJN-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3N=CC=CN=3)=CC=2)CCC1 ZCYDINFDQPIOJN-UHFFFAOYSA-N 0.000 description 1
- CCPCXYSMLOVMQV-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3N=CN=CC=3)=CC=2)CCC1 CCPCXYSMLOVMQV-UHFFFAOYSA-N 0.000 description 1
- KZRKVPUALYWSNV-UHFFFAOYSA-N n-[4-[6-(3,4-dimethoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3SC=CC=3)=CC=2)CCC1 KZRKVPUALYWSNV-UHFFFAOYSA-N 0.000 description 1
- AHPYYEPGIJKIDK-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3ON=CC=3)=CC=2)C=C1OC1CCCC1 AHPYYEPGIJKIDK-UHFFFAOYSA-N 0.000 description 1
- HUKQWTWCHJGFRD-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CNC=3)=CC=2)C=C1OC1CCCC1 HUKQWTWCHJGFRD-UHFFFAOYSA-N 0.000 description 1
- BPPWQKSQNDSWGD-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C3=C(N=C(C)S3)C)=CC=2)C=C1OC1CCCC1 BPPWQKSQNDSWGD-UHFFFAOYSA-N 0.000 description 1
- JJNDPKDOAWRUPR-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(C)=O)=CC=2)C=C1OC1CCCC1 JJNDPKDOAWRUPR-UHFFFAOYSA-N 0.000 description 1
- LNUCNRYFCVYTII-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)C=C1OC1CCCC1 LNUCNRYFCVYTII-UHFFFAOYSA-N 0.000 description 1
- GXDCRMOJBRXELT-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CC=NC=3)=CC=2)C=C1OC1CCCC1 GXDCRMOJBRXELT-UHFFFAOYSA-N 0.000 description 1
- LSKKFDJFMGJGGK-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)C=C1OC1CCCC1 LSKKFDJFMGJGGK-UHFFFAOYSA-N 0.000 description 1
- BILXGQUUIYPMDS-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3C=CN=CC=3)=CC=2)C=C1OC1CCCC1 BILXGQUUIYPMDS-UHFFFAOYSA-N 0.000 description 1
- QUFMUVWMLVVZCI-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CC=CN=3)=CC=2)C=C1OC1CCCC1 QUFMUVWMLVVZCI-UHFFFAOYSA-N 0.000 description 1
- LROZDQCZCKDWGO-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CN=CC=3)=CC=2)C=C1OC1CCCC1 LROZDQCZCKDWGO-UHFFFAOYSA-N 0.000 description 1
- VLQPUMLUHHKCKU-UHFFFAOYSA-N n-[4-[6-(3-cyclopentyloxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound COC1=CC=C(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3SC=CC=3)=CC=2)C=C1OC1CCCC1 VLQPUMLUHHKCKU-UHFFFAOYSA-N 0.000 description 1
- CKDNYFPRWFMGQL-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3ON=CC=3)=CC=2)=C1 CKDNYFPRWFMGQL-UHFFFAOYSA-N 0.000 description 1
- FTNTUTAJFQIECE-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CNC=3)=CC=2)=C1 FTNTUTAJFQIECE-UHFFFAOYSA-N 0.000 description 1
- MIBWHCSTFZTKFG-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C3=C(N=C(C)S3)C)=CC=2)=C1 MIBWHCSTFZTKFG-UHFFFAOYSA-N 0.000 description 1
- MLTHNTQICBFFIX-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(C)=O)=CC=2)=C1 MLTHNTQICBFFIX-UHFFFAOYSA-N 0.000 description 1
- INZHXNCVNPZTBJ-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 INZHXNCVNPZTBJ-UHFFFAOYSA-N 0.000 description 1
- HMZSBEMBRTUMMZ-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CC=NC=3)=CC=2)=C1 HMZSBEMBRTUMMZ-UHFFFAOYSA-N 0.000 description 1
- RIQZGPJQTKTCNV-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)=C1 RIQZGPJQTKTCNV-UHFFFAOYSA-N 0.000 description 1
- DOOCRWNRVGSKGN-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3C=CN=CC=3)=CC=2)=C1 DOOCRWNRVGSKGN-UHFFFAOYSA-N 0.000 description 1
- PRVFRLSYAHLQJR-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CC=CN=3)=CC=2)=C1 PRVFRLSYAHLQJR-UHFFFAOYSA-N 0.000 description 1
- CNHINOPZRMQLKT-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CN=CC=3)=CC=2)=C1 CNHINOPZRMQLKT-UHFFFAOYSA-N 0.000 description 1
- VLKCOBGNESTUJR-UHFFFAOYSA-N n-[4-[6-(3-ethoxy-4-methoxyphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3SC=CC=3)=CC=2)=C1 VLKCOBGNESTUJR-UHFFFAOYSA-N 0.000 description 1
- LVTUYFZJNIWVNN-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3ON=CC=3)=CC=2)=C1 LVTUYFZJNIWVNN-UHFFFAOYSA-N 0.000 description 1
- PXRWOUWLMROAIE-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3NC=NC=3)=CC=2)=C1 PXRWOUWLMROAIE-UHFFFAOYSA-N 0.000 description 1
- DTTRKWSIPAQZBO-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C3=C(N=C(C)S3)C)=CC=2)=C1 DTTRKWSIPAQZBO-UHFFFAOYSA-N 0.000 description 1
- STVJLZFNZNJUQX-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(C)=O)=CC=2)=C1 STVJLZFNZNJUQX-UHFFFAOYSA-N 0.000 description 1
- HHYVULNZLGTVLI-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 HHYVULNZLGTVLI-UHFFFAOYSA-N 0.000 description 1
- BQIZUYUMMSCFHH-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CC=NC=3)=CC=2)=C1 BQIZUYUMMSCFHH-UHFFFAOYSA-N 0.000 description 1
- LFOPOKKHWMUPHN-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)=C1 LFOPOKKHWMUPHN-UHFFFAOYSA-N 0.000 description 1
- FVRFIGSVGIMLEC-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3C=CN=CC=3)=CC=2)=C1 FVRFIGSVGIMLEC-UHFFFAOYSA-N 0.000 description 1
- ARBXLBZQSWZBSJ-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CC=CN=3)=CC=2)=C1 ARBXLBZQSWZBSJ-UHFFFAOYSA-N 0.000 description 1
- WZFLMQXAROKFBQ-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-4-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3N=CN=CC=3)=CC=2)=C1 WZFLMQXAROKFBQ-UHFFFAOYSA-N 0.000 description 1
- XXHSDGJVUVVZKD-UHFFFAOYSA-N n-[4-[6-(3-methoxy-4-methylsulfonylphenyl)-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC(C=2CCCN(N=2)C(=O)C=2C=CC(NC(=O)C=3SC=CC=3)=CC=2)=C1 XXHSDGJVUVVZKD-UHFFFAOYSA-N 0.000 description 1
- MCPGNDYFOCHJEB-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3ON=CC=3)=CC=2)CCC1 MCPGNDYFOCHJEB-UHFFFAOYSA-N 0.000 description 1
- ZOMDKUOZOLSCRR-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3NC=NC=3)=CC=2)CCC1 ZOMDKUOZOLSCRR-UHFFFAOYSA-N 0.000 description 1
- CMHRJQFDNRKNPD-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C3=C(N=C(C)S3)C)=CC=2)CCC1 CMHRJQFDNRKNPD-UHFFFAOYSA-N 0.000 description 1
- NEYZYDZDCOPYML-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]acetamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(C)=O)=CC=2)CCC1 NEYZYDZDCOPYML-UHFFFAOYSA-N 0.000 description 1
- LDSPOMARIHVEOX-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]furan-2-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)CCC1 LDSPOMARIHVEOX-UHFFFAOYSA-N 0.000 description 1
- DMMQBMFWOMTSEY-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3N=CC=NC=3)=CC=2)CCC1 DMMQBMFWOMTSEY-UHFFFAOYSA-N 0.000 description 1
- RQFYRBDITBGWIL-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)CCC1 RQFYRBDITBGWIL-UHFFFAOYSA-N 0.000 description 1
- GVQGOOPKCNAUAW-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3N=CC=CN=3)=CC=2)CCC1 GVQGOOPKCNAUAW-UHFFFAOYSA-N 0.000 description 1
- QDAAMJNXMYDQQZ-UHFFFAOYSA-N n-[4-[6-[4-methoxy-3-(trifluoromethoxy)phenyl]-4,5-dihydro-3h-pyridazine-2-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=NN(C(=O)C=2C=CC(NC(=O)C=3SC=CC=3)=CC=2)CCC1 QDAAMJNXMYDQQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001599 osteoclastic effect Effects 0.000 description 1
- 210000005009 osteogenic cell Anatomy 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- TXJKATOSKLUITR-UHFFFAOYSA-N pyrazine-2-carbonyl chloride Chemical compound ClC(=O)C1=CN=CC=N1 TXJKATOSKLUITR-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- FOVRZAGACROHCK-UHFFFAOYSA-N pyrimidine-2-carbonyl chloride Chemical compound ClC(=O)C1=NC=CC=N1 FOVRZAGACROHCK-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Virology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Cette invention concerne l'utilisation de composés de formule (I) dans laquelle R?1¿, R?2¿, Q et B ont les significations données dans la revendication 1, et/ou leurs sels physiologiquement admissibles, pour la fabrication d'un produit pharmaceutique permettant de traiter l'ostéoporose, les tumeurs, l'athérosclérose, l'arthrite rhumatoïde, la sclérose en plaques, le diabète sucré, la colite ulcéreuse et le SIDA.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19915364.7 | 1999-04-06 | ||
DE19915364A DE19915364A1 (de) | 1999-04-06 | 1999-04-06 | Verwendung von Arylalkanoylpyridazinen |
PCT/EP2000/002280 WO2000059484A2 (fr) | 1999-04-06 | 2000-03-15 | Utilisation d'arylalcanoylpyridazines |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2367051A1 true CA2367051A1 (fr) | 2000-10-12 |
Family
ID=7903583
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002367051A Abandoned CA2367051A1 (fr) | 1999-04-06 | 2000-03-15 | Utilisation d'arylalcanoylpyridazines |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP1143944A3 (fr) |
JP (1) | JP2002541095A (fr) |
KR (1) | KR20020000550A (fr) |
CN (1) | CN1355702A (fr) |
AR (1) | AR023261A1 (fr) |
AU (1) | AU3811600A (fr) |
BR (1) | BR0009549A (fr) |
CA (1) | CA2367051A1 (fr) |
CZ (1) | CZ20013598A3 (fr) |
DE (1) | DE19915364A1 (fr) |
HU (1) | HUP0200311A3 (fr) |
ID (1) | ID30381A (fr) |
MX (1) | MXPA01010034A (fr) |
NO (1) | NO20014845L (fr) |
PL (1) | PL350963A1 (fr) |
RU (1) | RU2001129703A (fr) |
WO (1) | WO2000059484A2 (fr) |
ZA (1) | ZA200109120B (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9556177B2 (en) | 2007-06-29 | 2017-01-31 | Millennium Pharmaceuticals, Inc. | Substituted 1,3-thiazoles as synthetic intermediates for preparation of Raf kinase inhibitors |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20040087335A (ko) * | 2002-03-01 | 2004-10-13 | 야마노우치세이야쿠 가부시키가이샤 | 질소 함유 복소환 화합물 |
DE10224888A1 (de) * | 2002-06-05 | 2003-12-24 | Merck Patent Gmbh | Pyridazinderivate |
DE10225574A1 (de) * | 2002-06-10 | 2003-12-18 | Merck Patent Gmbh | Aryloxime |
EP1640010A1 (fr) * | 2003-07-01 | 2006-03-29 | Astellas Pharma Inc. | Agent d'induction de croissance dans la masse osseuse |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19632549A1 (de) * | 1996-08-13 | 1998-02-19 | Merck Patent Gmbh | Arylalkanoylpyridazine |
DE19826841A1 (de) * | 1998-06-16 | 1999-12-23 | Merck Patent Gmbh | Arylalkanoylpyridazine |
DE19850701A1 (de) * | 1998-11-04 | 2000-05-11 | Merck Patent Gmbh | Benzoylpyridazine |
DE19915365A1 (de) * | 1999-04-06 | 2000-10-12 | Merck Patent Gmbh | Tetrahydropyridazin-Derivate |
-
1999
- 1999-04-06 DE DE19915364A patent/DE19915364A1/de not_active Withdrawn
-
2000
- 2000-03-15 CN CN00805648A patent/CN1355702A/zh active Pending
- 2000-03-15 CZ CZ20013598A patent/CZ20013598A3/cs unknown
- 2000-03-15 JP JP2000609048A patent/JP2002541095A/ja active Pending
- 2000-03-15 AU AU38116/00A patent/AU3811600A/en not_active Abandoned
- 2000-03-15 RU RU2001129703/15A patent/RU2001129703A/ru unknown
- 2000-03-15 ID IDW00200102346A patent/ID30381A/id unknown
- 2000-03-15 BR BR0009549-4A patent/BR0009549A/pt active Pending
- 2000-03-15 MX MXPA01010034A patent/MXPA01010034A/es not_active Application Discontinuation
- 2000-03-15 EP EP00916949A patent/EP1143944A3/fr not_active Withdrawn
- 2000-03-15 WO PCT/EP2000/002280 patent/WO2000059484A2/fr not_active Application Discontinuation
- 2000-03-15 CA CA002367051A patent/CA2367051A1/fr not_active Abandoned
- 2000-03-15 PL PL00350963A patent/PL350963A1/xx unknown
- 2000-03-15 HU HU0200311A patent/HUP0200311A3/hu unknown
- 2000-03-15 KR KR1020017011993A patent/KR20020000550A/ko not_active Application Discontinuation
- 2000-04-05 AR ARP000101547A patent/AR023261A1/es unknown
-
2001
- 2001-10-05 NO NO20014845A patent/NO20014845L/no not_active Application Discontinuation
- 2001-11-05 ZA ZA200109120A patent/ZA200109120B/xx unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9556177B2 (en) | 2007-06-29 | 2017-01-31 | Millennium Pharmaceuticals, Inc. | Substituted 1,3-thiazoles as synthetic intermediates for preparation of Raf kinase inhibitors |
US9920048B2 (en) | 2007-06-29 | 2018-03-20 | Millennium Pharmaceuticals, Inc. | Substituted pyrimidines for inhibiting Raf kinase activity |
Also Published As
Publication number | Publication date |
---|---|
NO20014845D0 (no) | 2001-10-05 |
HUP0200311A2 (hu) | 2002-11-28 |
DE19915364A1 (de) | 2000-10-12 |
MXPA01010034A (es) | 2002-04-24 |
EP1143944A2 (fr) | 2001-10-17 |
ID30381A (id) | 2001-11-29 |
BR0009549A (pt) | 2002-03-26 |
PL350963A1 (en) | 2003-02-24 |
WO2000059484A3 (fr) | 2001-08-23 |
AU3811600A (en) | 2000-10-23 |
HUP0200311A3 (en) | 2002-12-28 |
EP1143944A3 (fr) | 2002-09-11 |
WO2000059484A2 (fr) | 2000-10-12 |
JP2002541095A (ja) | 2002-12-03 |
CZ20013598A3 (cs) | 2002-01-16 |
RU2001129703A (ru) | 2004-02-20 |
KR20020000550A (ko) | 2002-01-05 |
ZA200109120B (en) | 2003-11-13 |
AR023261A1 (es) | 2002-09-04 |
CN1355702A (zh) | 2002-06-26 |
NO20014845L (no) | 2001-10-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2263417C (fr) | Arylalcanoylpyridazines | |
CA2185397C (fr) | Arylalkyldiazinones | |
JP4395823B2 (ja) | アリール及びヘテロアリール置換複素環式尿素を用いたrafキナーゼの阻害 | |
US6417188B1 (en) | Arylalkanoylpyridazines | |
US6531473B2 (en) | Method of treatment using arylalkylpyridazinones | |
CN101537001A (zh) | 作为jak-stat3信号通路抑制剂的化合物的应用 | |
TW200911251A (en) | Tetrahydroisoquinolin-1-one derivatives or salt thereof | |
US6376493B1 (en) | Benzoylpyridazines | |
US6107295A (en) | Arylalkanoyl pyridazines | |
CA2367051A1 (fr) | Utilisation d'arylalcanoylpyridazines | |
JPH10511118A (ja) | エンドテリン受容体拮抗薬 | |
JP4198755B6 (ja) | アリールアルカノイルピリダジン誘導体 | |
SK13652001A3 (sk) | Použitie derivátov arylalkanoylpyridazínu | |
Branigan | Darmstadt, all of Germany | |
MXPA99001386A (en) | Arylalkanoyl pyridazines | |
JP2005139106A (ja) | ベンゾフラン誘導体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |