NO301006B1 - Analogifremgangsmåte for fremstilling av terapeutisk aktive pyrazolderivater - Google Patents
Analogifremgangsmåte for fremstilling av terapeutisk aktive pyrazolderivater Download PDFInfo
- Publication number
- NO301006B1 NO301006B1 NO904134A NO904134A NO301006B1 NO 301006 B1 NO301006 B1 NO 301006B1 NO 904134 A NO904134 A NO 904134A NO 904134 A NO904134 A NO 904134A NO 301006 B1 NO301006 B1 NO 301006B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- compound
- substituted
- formula
- salts
- Prior art date
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- 150000003217 pyrazoles Chemical class 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 175
- -1 nitro, amino Chemical group 0.000 claims abstract description 119
- 150000003839 salts Chemical class 0.000 claims abstract description 111
- 238000000034 method Methods 0.000 claims abstract description 97
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 59
- 230000008569 process Effects 0.000 claims abstract description 56
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 39
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 36
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 36
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 108
- 125000001589 carboacyl group Chemical group 0.000 claims description 59
- 125000003277 amino group Chemical group 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 239000007858 starting material Substances 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 14
- 125000003118 aryl group Chemical group 0.000 abstract description 7
- 125000002252 acyl group Chemical group 0.000 abstract description 5
- 125000004442 acylamino group Chemical group 0.000 abstract description 5
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000001819 mass spectrum Methods 0.000 description 229
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- 239000000203 mixture Substances 0.000 description 120
- 238000006243 chemical reaction Methods 0.000 description 110
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 103
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 86
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000002904 solvent Substances 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 36
- 239000013078 crystal Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 17
- 230000002411 adverse Effects 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 235000011054 acetic acid Nutrition 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000003638 chemical reducing agent Substances 0.000 description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 206010061218 Inflammation Diseases 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 230000004054 inflammatory process Effects 0.000 description 8
- 239000002198 insoluble material Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 150000002148 esters Chemical group 0.000 description 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
- 150000007524 organic acids Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
- 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 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 210000002683 foot Anatomy 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 230000002757 inflammatory effect Effects 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 150000007522 mineralic acids Chemical class 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 230000036407 pain Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 5
- YMJLEPMVGQBLHL-UHFFFAOYSA-N 1h-pyrazole-5-carbonitrile Chemical compound N#CC1=CC=NN1 YMJLEPMVGQBLHL-UHFFFAOYSA-N 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 102000000503 Collagen Type II Human genes 0.000 description 5
- 108010041390 Collagen Type II Proteins 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 150000003973 alkyl amines Chemical class 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- JBXLGRLORITUHD-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylic acid Chemical compound C1=CC(SC)=CC=C1C1=CC(C(O)=O)=NN1C1=CC=C(F)C=C1 JBXLGRLORITUHD-UHFFFAOYSA-N 0.000 description 4
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 208000011231 Crohn disease Diseases 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 230000002785 anti-thrombosis Effects 0.000 description 4
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 238000010531 catalytic reduction reaction Methods 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
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- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
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- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- KLBIUKJOZFWCLW-UHFFFAOYSA-N thallium(iii) nitrate Chemical compound [Tl+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O KLBIUKJOZFWCLW-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- IDXKMSQUTCYDPK-UHFFFAOYSA-N 1-(4-aminophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C#N)=NN1C1=CC=C(N)C=C1 IDXKMSQUTCYDPK-UHFFFAOYSA-N 0.000 description 3
- TYWKFUDMIDTRSC-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)pyrazol-3-amine Chemical compound C1=CC(SC)=CC=C1C1=CC(N)=NN1C1=CC=C(F)C=C1 TYWKFUDMIDTRSC-UHFFFAOYSA-N 0.000 description 3
- LNFNRNGMQNJFBJ-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazol-3-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(N)=NN1C1=CC=C(F)C=C1 LNFNRNGMQNJFBJ-UHFFFAOYSA-N 0.000 description 3
- NKBRWXWNSUIHNI-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C#N)=NN1C1=CC=C(F)C=C1 NKBRWXWNSUIHNI-UHFFFAOYSA-N 0.000 description 3
- RIJYNNRXDHFDSL-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(O)=O)=NN1C1=CC=C(F)C=C1 RIJYNNRXDHFDSL-UHFFFAOYSA-N 0.000 description 3
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
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- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000000872 buffer Substances 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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UETLMBWMVIQIGU-UHFFFAOYSA-N calcium azide Chemical compound [Ca+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] UETLMBWMVIQIGU-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([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
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 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
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000001 effect on platelet aggregation Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- AIOKIAZWWNBJMD-UHFFFAOYSA-N ethyl 1,5-bis(4-methoxyphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(OC)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(OC)C=C1 AIOKIAZWWNBJMD-UHFFFAOYSA-N 0.000 description 1
- RNNZKFBGFPFMGM-UHFFFAOYSA-N ethyl 1-(2,4-difluorophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(F)C=C(F)C=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 RNNZKFBGFPFMGM-UHFFFAOYSA-N 0.000 description 1
- OCSMGTCFOLPWBF-UHFFFAOYSA-N ethyl 1-(2,4-difluorophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(F)C=C(F)C=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 OCSMGTCFOLPWBF-UHFFFAOYSA-N 0.000 description 1
- YIKIRFTWMUZZMW-UHFFFAOYSA-N ethyl 1-(2,5-difluorophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C(F)=CC=C(F)C=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 YIKIRFTWMUZZMW-UHFFFAOYSA-N 0.000 description 1
- XQWPHMSYNMDDLF-UHFFFAOYSA-N ethyl 1-(2-chlorophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=CC=C(Cl)C=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 XQWPHMSYNMDDLF-UHFFFAOYSA-N 0.000 description 1
- POQDTIRCTFZUPA-UHFFFAOYSA-N ethyl 1-(2-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=CC=C(F)C=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 POQDTIRCTFZUPA-UHFFFAOYSA-N 0.000 description 1
- KXRXNYFFYCDSOB-UHFFFAOYSA-N ethyl 1-(3-fluorophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=CC(F)=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 KXRXNYFFYCDSOB-UHFFFAOYSA-N 0.000 description 1
- SUKLDHJAFNPBIA-UHFFFAOYSA-N ethyl 1-(4-aminophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(N)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 SUKLDHJAFNPBIA-UHFFFAOYSA-N 0.000 description 1
- SBLIXODXFQZINW-UHFFFAOYSA-N ethyl 1-(4-aminophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(N)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 SBLIXODXFQZINW-UHFFFAOYSA-N 0.000 description 1
- AXOAILUZUQLKKG-UHFFFAOYSA-N ethyl 1-(4-fluoro-2-nitrophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(F)C=C([N+]([O-])=O)C=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 AXOAILUZUQLKKG-UHFFFAOYSA-N 0.000 description 1
- IMDXNDZKCDCGSO-UHFFFAOYSA-N ethyl 1-(4-fluorophenyl)-5-(4-formamidophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(F)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(NC=O)C=C1 IMDXNDZKCDCGSO-UHFFFAOYSA-N 0.000 description 1
- IOHSZJLGDJKSTG-UHFFFAOYSA-N ethyl 1-(4-fluorophenyl)-5-(4-methoxyphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(F)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(OC)C=C1 IOHSZJLGDJKSTG-UHFFFAOYSA-N 0.000 description 1
- XGNJUXREQVAIEN-UHFFFAOYSA-N ethyl 1-(4-fluorophenyl)-5-[4-(2-oxoethylamino)phenyl]pyrazole-3-carboxylate Chemical compound C=1C=C(F)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(NCC=O)C=C1 XGNJUXREQVAIEN-UHFFFAOYSA-N 0.000 description 1
- WDGXVSGGGVZQKU-UHFFFAOYSA-N ethyl 1-(4-formamidophenyl)-5-(4-methylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(NC=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(C)C=C1 WDGXVSGGGVZQKU-UHFFFAOYSA-N 0.000 description 1
- JOFOJUNBRCBGHF-UHFFFAOYSA-N ethyl 1-(4-formamidophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(NC=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 JOFOJUNBRCBGHF-UHFFFAOYSA-N 0.000 description 1
- RLGYJWJGGQSZQF-UHFFFAOYSA-N ethyl 1-(4-formamidophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(NC=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 RLGYJWJGGQSZQF-UHFFFAOYSA-N 0.000 description 1
- RUYZDIWQXAEKCP-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(OC)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 RUYZDIWQXAEKCP-UHFFFAOYSA-N 0.000 description 1
- ZYAQUOJLZMGRPV-UHFFFAOYSA-N ethyl 1-(4-methylphenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(C)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 ZYAQUOJLZMGRPV-UHFFFAOYSA-N 0.000 description 1
- MZHWVKVPHTWDLG-UHFFFAOYSA-N ethyl 1-(4-methylphenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(C)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MZHWVKVPHTWDLG-UHFFFAOYSA-N 0.000 description 1
- CMNIXUIZAMKHRW-UHFFFAOYSA-N ethyl 1-[4-(methylamino)phenyl]-5-(4-methylsulfonylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(NC)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 CMNIXUIZAMKHRW-UHFFFAOYSA-N 0.000 description 1
- YBMYJWYUJDAFQU-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=CC(C=2C=CC(SC)=CC=2)=NN1C1=CC=C(F)C=C1 YBMYJWYUJDAFQU-UHFFFAOYSA-N 0.000 description 1
- KVZMKNKWVKCNPX-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=NN1C1=CC=C(F)C=C1 KVZMKNKWVKCNPX-UHFFFAOYSA-N 0.000 description 1
- GTFQWMDAUWOOKN-UHFFFAOYSA-N ethyl 4-(3,5-ditert-butyl-4-hydroxyphenyl)-2,4-dioxobutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GTFQWMDAUWOOKN-UHFFFAOYSA-N 0.000 description 1
- KHEAMBUFZSDFDX-UHFFFAOYSA-N ethyl 4-(4-acetylphenyl)-2,4-dioxobutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=C(C(C)=O)C=C1 KHEAMBUFZSDFDX-UHFFFAOYSA-N 0.000 description 1
- QQMYOPVSVNPECO-UHFFFAOYSA-N ethyl 4-(4-methylphenyl)-2,4-dioxobutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=C(C)C=C1 QQMYOPVSVNPECO-UHFFFAOYSA-N 0.000 description 1
- XWLRUMMFRQBZRJ-UHFFFAOYSA-N ethyl 4-(5-methylsulfanylthiophen-2-yl)-2,4-dioxobutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=C(SC)S1 XWLRUMMFRQBZRJ-UHFFFAOYSA-N 0.000 description 1
- MEDKZHAHTKVICR-UHFFFAOYSA-N ethyl 5-(3,5-ditert-butyl-4-hydroxyphenyl)-1-(4-fluorophenyl)pyrazole-3-carboxylate Chemical compound CCOC(=O)c1cc(-c2cc(c(O)c(c2)C(C)(C)C)C(C)(C)C)n(n1)-c1ccc(F)cc1 MEDKZHAHTKVICR-UHFFFAOYSA-N 0.000 description 1
- LDWPVWOOEXIMHD-UHFFFAOYSA-N ethyl 5-(4-acetylphenyl)-1-(4-fluorophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(F)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(C(C)=O)C=C1 LDWPVWOOEXIMHD-UHFFFAOYSA-N 0.000 description 1
- KWAPJRQIOBXGIV-UHFFFAOYSA-N ethyl 5-(4-aminophenyl)-1-(4-fluorophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(F)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(N)C=C1 KWAPJRQIOBXGIV-UHFFFAOYSA-N 0.000 description 1
- BGZQQRSUMCGUOP-UHFFFAOYSA-N ethyl 5-(4-fluorophenyl)-1-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(SC)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(F)C=C1 BGZQQRSUMCGUOP-UHFFFAOYSA-N 0.000 description 1
- MIHJOENGEGDFRA-UHFFFAOYSA-N ethyl 5-(4-methoxyphenyl)-1-(4-nitrophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(OC)C=C1 MIHJOENGEGDFRA-UHFFFAOYSA-N 0.000 description 1
- OPGLXDJBUNQJPT-UHFFFAOYSA-N ethyl 5-(4-methylphenyl)-1-(4-nitrophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(C)C=C1 OPGLXDJBUNQJPT-UHFFFAOYSA-N 0.000 description 1
- WTMFFRPNRZBJCF-UHFFFAOYSA-N ethyl 5-(4-methylphenyl)-1-[4-(2-oxoethylamino)phenyl]pyrazole-3-carboxylate Chemical compound C=1C=C(NCC=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(C)C=C1 WTMFFRPNRZBJCF-UHFFFAOYSA-N 0.000 description 1
- GHUBNPKEBHNMJO-UHFFFAOYSA-N ethyl 5-(4-methylsulfanylphenyl)-1-(2-nitrophenyl)pyrazole-3-carboxylate Chemical compound C=1C=CC=C([N+]([O-])=O)C=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 GHUBNPKEBHNMJO-UHFFFAOYSA-N 0.000 description 1
- AUCGOWGTTJHPBC-UHFFFAOYSA-N ethyl 5-(4-methylsulfanylphenyl)-1-(4-nitrophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 AUCGOWGTTJHPBC-UHFFFAOYSA-N 0.000 description 1
- KYGARQAZKDKKAZ-UHFFFAOYSA-N ethyl 5-(4-methylsulfanylphenyl)-1-[4-(2-oxoethylamino)phenyl]pyrazole-3-carboxylate Chemical compound C=1C=C(NCC=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 KYGARQAZKDKKAZ-UHFFFAOYSA-N 0.000 description 1
- ZAXSDFNRCWBQTI-UHFFFAOYSA-N ethyl 5-(4-methylsulfanylphenyl)-1-phenylpyrazole-3-carboxylate Chemical compound C=1C=CC=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 ZAXSDFNRCWBQTI-UHFFFAOYSA-N 0.000 description 1
- AFHXGQTURAAQPY-UHFFFAOYSA-N ethyl 5-(4-methylsulfanylphenyl)-1-pyridin-4-ylpyrazole-3-carboxylate;hydrochloride Chemical compound Cl.C=1C=NC=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)C=C1 AFHXGQTURAAQPY-UHFFFAOYSA-N 0.000 description 1
- NPRYYJDTLCFEIF-UHFFFAOYSA-N ethyl 5-(4-methylsulfonylphenyl)-1-(4-nitrophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 NPRYYJDTLCFEIF-UHFFFAOYSA-N 0.000 description 1
- CYPCCEUPGDVQCQ-UHFFFAOYSA-N ethyl 5-(4-methylsulfonylphenyl)-1-[4-(2-oxoethylamino)phenyl]pyrazole-3-carboxylate Chemical compound C=1C=C(NCC=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 CYPCCEUPGDVQCQ-UHFFFAOYSA-N 0.000 description 1
- NLEXQJVBWZXMRU-UHFFFAOYSA-N ethyl 5-(4-methylsulfonylphenyl)-1-phenylpyrazole-3-carboxylate Chemical compound C=1C=CC=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 NLEXQJVBWZXMRU-UHFFFAOYSA-N 0.000 description 1
- CCMWYELBFYIUTB-UHFFFAOYSA-N ethyl 5-(4-methylsulfonylphenyl)-1-pyridin-4-ylpyrazole-3-carboxylate Chemical compound C=1C=NC=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 CCMWYELBFYIUTB-UHFFFAOYSA-N 0.000 description 1
- NLTDMJABXUBSQV-UHFFFAOYSA-N ethyl 5-(5-methylsulfanylthiophen-2-yl)-1-(4-nitrophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(SC)S1 NLTDMJABXUBSQV-UHFFFAOYSA-N 0.000 description 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- QUIOHQITLKCGNW-ODZAUARKSA-L magnesium;(z)-but-2-enedioate Chemical compound [Mg+2].[O-]C(=O)\C=C/C([O-])=O QUIOHQITLKCGNW-ODZAUARKSA-L 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- OQJWFSVVBUCFMZ-UHFFFAOYSA-N methyl n-[1-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazol-3-yl]carbamate Chemical compound C=1C=C(F)C=CC=1N1N=C(NC(=O)OC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 OQJWFSVVBUCFMZ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- QWYWYBJSXUWMDD-UHFFFAOYSA-N n,n-dimethyl-5-(4-methylsulfonylphenyl)-1-[4-(2-oxoethylamino)phenyl]pyrazole-3-carboxamide Chemical compound C=1C=C(NCC=O)C=CC=1N1N=C(C(=O)N(C)C)C=C1C1=CC=C(S(C)(=O)=O)C=C1 QWYWYBJSXUWMDD-UHFFFAOYSA-N 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- WWKRAFMFFKHIMZ-UHFFFAOYSA-N n-[1-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazol-3-yl]acetamide Chemical compound C=1C=C(F)C=CC=1N1N=C(NC(=O)C)C=C1C1=CC=C(S(C)(=O)=O)C=C1 WWKRAFMFFKHIMZ-UHFFFAOYSA-N 0.000 description 1
- GXYIPWUZFOGNCW-UHFFFAOYSA-N n-[1-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazol-3-yl]methanesulfonamide Chemical compound C=1C=C(F)C=CC=1N1N=C(NS(=O)(=O)C)C=C1C1=CC=C(S(C)(=O)=O)C=C1 GXYIPWUZFOGNCW-UHFFFAOYSA-N 0.000 description 1
- ZMWVJZFYSRGJGK-UHFFFAOYSA-N n-[2-[3-cyano-5-(4-methylsulfonylphenyl)pyrazol-1-yl]phenyl]formamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C#N)=NN1C1=CC=CC=C1NC=O ZMWVJZFYSRGJGK-UHFFFAOYSA-N 0.000 description 1
- UEMJMCSPZMVNQU-UHFFFAOYSA-N n-[4-[3-(difluoromethyl)-5-(4-methylsulfanylphenyl)pyrazol-1-yl]phenyl]formamide Chemical compound C1=CC(SC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(NC=O)C=C1 UEMJMCSPZMVNQU-UHFFFAOYSA-N 0.000 description 1
- YNOYTUDGMVQLNJ-UHFFFAOYSA-N n-[4-[3-cyano-5-(4-methylsulfonylphenyl)pyrazol-1-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)=CC(C#N)=N1 YNOYTUDGMVQLNJ-UHFFFAOYSA-N 0.000 description 1
- UDUPHVJKFGCLBS-UHFFFAOYSA-N n-[4-[5-(4-methylsulfanylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]formamide Chemical compound C1=CC(SC)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(NC=O)C=C1 UDUPHVJKFGCLBS-UHFFFAOYSA-N 0.000 description 1
- PVDPKOPOUALBSX-UHFFFAOYSA-N n-[4-[5-(4-methylsulfinylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]formamide Chemical compound C1=CC(S(=O)C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(NC=O)C=C1 PVDPKOPOUALBSX-UHFFFAOYSA-N 0.000 description 1
- MRPLJIYEXYMNBO-UHFFFAOYSA-N n-[4-[5-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]formamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(NC=O)C=C1 MRPLJIYEXYMNBO-UHFFFAOYSA-N 0.000 description 1
- XKYJVVBOBYXAMI-UHFFFAOYSA-N n-[4-[5-cyano-2-(4-fluorophenyl)pyrazol-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC(C#N)=NN1C1=CC=C(F)C=C1 XKYJVVBOBYXAMI-UHFFFAOYSA-N 0.000 description 1
- SAMQWYYFDXOTNY-UHFFFAOYSA-N n-[[1-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazol-3-yl]methyl]acetamide Chemical compound C=1C=C(F)C=CC=1N1N=C(CNC(=O)C)C=C1C1=CC=C(S(C)(=O)=O)C=C1 SAMQWYYFDXOTNY-UHFFFAOYSA-N 0.000 description 1
- SWTFBLUIBHXOAH-UHFFFAOYSA-N n-butylhydroxylamine Chemical compound CCCCNO SWTFBLUIBHXOAH-UHFFFAOYSA-N 0.000 description 1
- ZQMDPSKTPXNCAQ-UHFFFAOYSA-N n-cyclopropyl-1-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)pyrazole-3-carboxamide Chemical compound C1=CC(SC)=CC=C1C1=CC(C(=O)NC2CC2)=NN1C1=CC=C(F)C=C1 ZQMDPSKTPXNCAQ-UHFFFAOYSA-N 0.000 description 1
- KNMLOUNDEXHHCP-UHFFFAOYSA-N n-cyclopropyl-1-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrazole-3-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(=O)NC2CC2)=NN1C1=CC=C(F)C=C1 KNMLOUNDEXHHCP-UHFFFAOYSA-N 0.000 description 1
- VDUIPQNXOQMTBF-UHFFFAOYSA-N n-ethylhydroxylamine Chemical compound CCNO VDUIPQNXOQMTBF-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- PNSPGDXUAVSINV-UHFFFAOYSA-N n-methyl-1-[4-(methylamino)phenyl]-5-(4-methylsulfonylphenyl)pyrazole-3-carboxamide Chemical compound C=1C=C(NC)C=CC=1N1N=C(C(=O)NC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 PNSPGDXUAVSINV-UHFFFAOYSA-N 0.000 description 1
- IJIAHCQQHKLMPR-UHFFFAOYSA-N n-methyl-4-[3-methylsulfonyl-5-(4-methylsulfonylphenyl)pyrazol-1-yl]aniline;hydrochloride Chemical compound Cl.C1=CC(NC)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)=CC(S(C)(=O)=O)=N1 IJIAHCQQHKLMPR-UHFFFAOYSA-N 0.000 description 1
- PVFFRCROTRYYBP-UHFFFAOYSA-N n-methyl-4-[5-(4-methylsulfanylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]aniline Chemical compound C1=CC(NC)=CC=C1N1C(C=2C=CC(SC)=CC=2)=CC(C(F)(F)F)=N1 PVFFRCROTRYYBP-UHFFFAOYSA-N 0.000 description 1
- LQCVEYRPHXYHLO-UHFFFAOYSA-N n-methyl-4-[5-(4-methylsulfinylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]aniline;hydrochloride Chemical compound Cl.C1=CC(NC)=CC=C1N1C(C=2C=CC(=CC=2)S(C)=O)=CC(C(F)(F)F)=N1 LQCVEYRPHXYHLO-UHFFFAOYSA-N 0.000 description 1
- ZEEHSVXYAFQCGT-UHFFFAOYSA-N n-methyl-4-[5-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]aniline;hydrochloride Chemical compound Cl.C1=CC(NC)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)=CC(C(F)(F)F)=N1 ZEEHSVXYAFQCGT-UHFFFAOYSA-N 0.000 description 1
- NUSQNKMZMMOZHY-UHFFFAOYSA-N n-methyl-5-(4-methylsulfonylphenyl)-1-[4-(2-oxoethylamino)phenyl]pyrazole-3-carboxamide Chemical compound C=1C=C(NCC=O)C=CC=1N1N=C(C(=O)NC)C=C1C1=CC=C(S(C)(=O)=O)C=C1 NUSQNKMZMMOZHY-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- ODHYIQOBTIWVRZ-UHFFFAOYSA-N n-propan-2-ylhydroxylamine Chemical compound CC(C)NO ODHYIQOBTIWVRZ-UHFFFAOYSA-N 0.000 description 1
- OMXHKVKIKSASRV-UHFFFAOYSA-N n-propylhydroxylamine Chemical compound CCCNO OMXHKVKIKSASRV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- XWVKTOHUMPLABF-UHFFFAOYSA-N thallium(3+) Chemical class [Tl+3] XWVKTOHUMPLABF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 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
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898921466A GB8921466D0 (en) | 1989-09-22 | 1989-09-22 | Pyrazole derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
GB909008399A GB9008399D0 (en) | 1990-04-12 | 1990-04-12 | Pyrazole derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
Publications (3)
Publication Number | Publication Date |
---|---|
NO904134D0 NO904134D0 (no) | 1990-09-21 |
NO904134L NO904134L (no) | 1991-03-25 |
NO301006B1 true NO301006B1 (no) | 1997-09-01 |
Family
ID=26295958
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO904134A NO301006B1 (no) | 1989-09-22 | 1990-09-21 | Analogifremgangsmåte for fremstilling av terapeutisk aktive pyrazolderivater |
Country Status (20)
Country | Link |
---|---|
US (1) | US5134142A (zh) |
EP (1) | EP0418845B1 (zh) |
JP (1) | JP2586713B2 (zh) |
KR (1) | KR0182798B1 (zh) |
CN (1) | CN1046506C (zh) |
AT (1) | ATE126216T1 (zh) |
AU (1) | AU637142B2 (zh) |
CA (1) | CA2025599C (zh) |
DE (1) | DE69021472T2 (zh) |
DK (1) | DK0418845T3 (zh) |
ES (1) | ES2088933T3 (zh) |
FI (1) | FI102535B (zh) |
GR (1) | GR3017100T3 (zh) |
HU (2) | HU208122B (zh) |
IE (1) | IE68857B1 (zh) |
IL (1) | IL95675A (zh) |
NO (1) | NO301006B1 (zh) |
PH (1) | PH27357A (zh) |
PT (1) | PT95389B (zh) |
RU (2) | RU2021990C1 (zh) |
Families Citing this family (210)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU616564B2 (en) * | 1988-09-29 | 1991-10-31 | Sumitomo Chemical Company, Limited | Novel pyrazole compounds, method for production thereof, use thereof and intermediates for production thereof |
DE4039733A1 (de) * | 1990-12-13 | 1992-06-17 | Basf Ag | Substituierte 5-aminopyrazole |
NO179282C (no) * | 1991-01-18 | 1996-09-11 | Rhone Poulenc Agrochimie | Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter |
WO1992019615A2 (en) * | 1991-04-24 | 1992-11-12 | E.I. Du Pont De Nemours And Company | Fungicidal pyrazoles, pyrazolines and tetrahydropyridazines |
FR2682379B1 (fr) * | 1991-10-09 | 1994-02-11 | Rhone Poulenc Agrochimie | Nouveaux phenylpyrazoles fongicides. |
US5550147A (en) * | 1992-02-05 | 1996-08-27 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazole derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
IL104311A (en) * | 1992-02-05 | 1997-07-13 | Fujisawa Pharmaceutical Co | Pyrazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
FR2690440B1 (fr) * | 1992-04-27 | 1995-05-19 | Rhone Poulenc Agrochimie | Arylpyrazoles fongicides. |
FR2713225B1 (fr) * | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
FR2692575B1 (fr) * | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
US6492413B2 (en) | 1993-01-15 | 2002-12-10 | G.D. Searle & Co. | 3.4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
GB9420616D0 (en) * | 1994-10-12 | 1994-11-30 | Merck Sharp & Dohme | Method, compositions and use |
US5380738A (en) * | 1993-05-21 | 1995-01-10 | Monsanto Company | 2-substituted oxazoles further substituted by 4-fluorophenyl and 4-methylsulfonylphenyl as antiinflammatory agents |
US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
US5840746A (en) * | 1993-06-24 | 1998-11-24 | Merck Frosst Canada, Inc. | Use of inhibitors of cyclooxygenase in the treatment of neurodegenerative diseases |
US5387602A (en) * | 1993-08-30 | 1995-02-07 | Ortho Pharmaceutical Corporation | 1.5-diphenyl-3-(N-hydroxycarbamoyloxyalkyl)pyrazoles |
FR2711140B1 (fr) * | 1993-10-12 | 1996-01-05 | Sanofi Sa | 1-Naphtylpyrazole-3-carboxamides substitués actifs sur la neurotensine, leur préparation, les compositions pharmaceutiques en contenant. |
PL180717B1 (pl) * | 1993-11-30 | 2001-03-30 | Searle & Co | N o w e 1 -[4-(aminosulfonylo)fenylo]pirazolilobenzenosulfonamidy do leczenia stanów zapalnych PL PL PL PL PL PL PL |
US5401765A (en) * | 1993-11-30 | 1995-03-28 | G. D. Searle | 1,4,5-triphenyl pyrazolyl compounds for the treatment of inflammation and inflammation-related disorders |
US6716991B1 (en) | 1993-11-30 | 2004-04-06 | G. D. Searle & Co. | Process for preparing a substituted pyrazolyl benzenesulfonamide for the treatment of inflammation |
US6492411B1 (en) | 1993-11-30 | 2002-12-10 | G. D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides for the treatment of inflammation |
US5466823A (en) * | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
US5434178A (en) * | 1993-11-30 | 1995-07-18 | G.D. Searle & Co. | 1,3,5 trisubstituted pyrazole compounds for treatment of inflammation |
US5475018A (en) * | 1993-11-30 | 1995-12-12 | G. D. Searle & Co. | 1,5-diphenyl pyrazole compounds for treatment of inflammation |
US5500439A (en) * | 1993-12-09 | 1996-03-19 | Alteon Inc. | Aminopyrazoles |
US5486534A (en) * | 1994-07-21 | 1996-01-23 | G. D. Searle & Co. | 3,4-substituted pyrazoles for the treatment of inflammation |
US5908852A (en) * | 1994-11-14 | 1999-06-01 | G. D. Searle & Co. | 1,3,5 trisubstituted pyrazole compounds for treatment of inflammation |
JP2636819B2 (ja) | 1994-12-20 | 1997-07-30 | 日本たばこ産業株式会社 | オキサゾール系複素環式芳香族化合物 |
CN1174970C (zh) * | 1995-05-25 | 2004-11-10 | G·D·瑟尔公司 | 3-卤代烷基-1h-吡唑的制备方法 |
US6512121B2 (en) | 1998-09-14 | 2003-01-28 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US6515014B2 (en) | 1995-06-02 | 2003-02-04 | G. D. Searle & Co. | Thiophene substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
WO1996038418A1 (en) * | 1995-06-02 | 1996-12-05 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US5756529A (en) * | 1995-09-29 | 1998-05-26 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides for use in veterinary therapies |
GB9520584D0 (en) * | 1995-10-09 | 1995-12-13 | Fujisawa Pharmaceutical Co | Pyrazole derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
US5908858A (en) * | 1996-04-05 | 1999-06-01 | Sankyo Company, Limited | 1,2-diphenylpyrrole derivatives, their preparation and their therapeutic uses |
US6677364B2 (en) | 1998-04-20 | 2004-01-13 | G.D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
CN1246847A (zh) * | 1996-12-23 | 2000-03-08 | 杜邦药品公司 | 作为Xa因子抑制剂的含氮杂芳族化合物 |
ES2312184T3 (es) | 1997-03-21 | 2009-02-16 | Chugai Seiyaku Kabushiki Kaisha | Agentes preventivos terapeuticos para el tratamiento de esclerosis multiple, que contienen anticuerpos anti-receptores de il-6 antagonistas. |
US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
AU7726898A (en) * | 1997-05-22 | 1998-12-11 | G.D. Searle & Co. | Pyrazole derivatives as p38 kinase inhibitors |
US6087496A (en) | 1998-05-22 | 2000-07-11 | G. D. Searle & Co. | Substituted pyrazoles suitable as p38 kinase inhibitors |
EP0983260A2 (en) * | 1997-05-22 | 2000-03-08 | G.D. Searle & Co. | 3(5)-HETEROARYL SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS |
US6979686B1 (en) | 2001-12-07 | 2005-12-27 | Pharmacia Corporation | Substituted pyrazoles as p38 kinase inhibitors |
PL337831A1 (en) * | 1997-06-19 | 2000-09-11 | Du Pont Pharm Co | Inhibitors of factor xa containing a specificity giving p1 group |
US5998424A (en) | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
AU750356B2 (en) * | 1997-09-24 | 2002-07-18 | Fujisawa Pharmaceutical Co., Ltd. | 1,5-diphenylpyrazole derivatives |
AUPO941497A0 (en) * | 1997-09-24 | 1997-10-16 | Fujisawa Pharmaceutical Co., Ltd. | Novel compounds |
AU751139B2 (en) | 1997-10-13 | 2002-08-08 | Astellas Pharma Inc. | Amide derivative |
AUPP042397A0 (en) * | 1997-11-18 | 1997-12-11 | Fujisawa Pharmaceutical Co., Ltd. | 5-arylpyrazole compounds |
US6306891B1 (en) | 1998-06-03 | 2001-10-23 | Merck & Co., Inc. | HIV integrase inhibitors |
EP1082121A4 (en) * | 1998-06-03 | 2003-02-05 | Merck & Co Inc | INTEGRASE HIV INHIBITORS |
US6262055B1 (en) * | 1998-06-03 | 2001-07-17 | Merck & Co., Inc. | HIV integrase inhibitors |
US6380249B1 (en) | 1998-06-03 | 2002-04-30 | Merck & Co., Inc. | HIV integrase inhibitors |
JP2002516909A (ja) * | 1998-06-05 | 2002-06-11 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 置換1−(4−アミノフェニル)ピラゾール及び抗炎症剤としてのそれらの使用 |
US6727238B2 (en) | 1998-06-11 | 2004-04-27 | Pfizer Inc. | Sulfonylbenzene compounds as anti-inflammatory/analgesic agents |
US6294558B1 (en) | 1999-05-31 | 2001-09-25 | Pfizer Inc. | Sulfonylbenzene compounds as anti-inflammatory/analgesic agents |
TNSN99111A1 (fr) * | 1998-06-11 | 2005-11-10 | Pfizer | Derives de sulfonylbenzene nouveaux, procede pour leur preparation et compositions pharmaceutiques les contenant. |
DE19831656A1 (de) * | 1998-07-15 | 2000-01-20 | Basf Ag | Verfahren zur Herstellung von Pyrazolen |
ES2244204T3 (es) | 1998-07-27 | 2005-12-01 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Derivados de dicetoacidos como inhibidores de polimerasas. |
GB9816358D0 (en) * | 1998-07-27 | 1998-09-23 | Angeletti P Ist Richerche Bio | Enzyme inhibitors |
USRE39708E1 (en) | 1998-08-07 | 2007-06-26 | Chiron Corporation | Estrogen receptor modulators |
US6291190B1 (en) * | 1998-08-25 | 2001-09-18 | The Board Of Trustees Of The Leland Stanford Junior University | Molecular differences between species of the M. tuberculosis complex |
US6191147B1 (en) * | 1998-12-24 | 2001-02-20 | Ppd Discovery, Inc. | Pyrazole compounds and uses thereof |
ATE411286T1 (de) | 1998-12-25 | 2008-10-15 | Shionogi & Co | Aromatische heterocyclen mit hiv integrase inhibierenden eigenschaften |
DE19904397A1 (de) * | 1999-02-04 | 2000-08-10 | Bayer Ag | Verwendung von Pyrazol-Carbonsäureamiden |
IL145508A0 (en) * | 1999-03-26 | 2002-06-30 | Euro Celtique Sa | Aryl substituted pyrazole, imidazole, oxazole, thiazole and pyrrole derivatives and pharmaceutical compositions containing the same |
DE60011100T2 (de) * | 1999-08-27 | 2005-06-16 | Abbott Laboratories, Abbott Park | Als cox-hemmer verwendbare sulfonylphenylpyrazol-verbindungen |
DE60001623T2 (de) | 1999-12-03 | 2003-12-18 | Pfizer Products Inc., Groton | Sulfamoylheteroarylpyrazolverbindungen zur Verwendung als analgetisches/entzündungshemmendes Mittel |
ES2208227T3 (es) | 1999-12-03 | 2004-06-16 | Pfizer Products Inc. | Compuestos de heteroarilfenilpirazol como agentes antiinflamatorios/analgesicos. |
WO2001040216A1 (en) * | 1999-12-03 | 2001-06-07 | Pfizer Products Inc. | Heterocyclo-alkylsulfonyl pyrazole derivatives as anti-inflammatory/analgesic agents |
DE60004001T2 (de) | 1999-12-03 | 2004-04-15 | Pfizer Products Inc., Groton | Acetylenderivate zur Verwendung als schmerzstillendes oder entzündungshemmendes Mittel |
US6569885B1 (en) * | 1999-12-23 | 2003-05-27 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
US6372752B1 (en) * | 2000-02-07 | 2002-04-16 | Genzyme Corporation | Inha inhibitors and methods of use thereof |
WO2001064669A1 (en) | 2000-03-03 | 2001-09-07 | Pfizer Products Inc. | Pyrazole ether derivatives as anti-inflammatory/analgesic agents |
CN1321112C (zh) * | 2000-03-24 | 2007-06-13 | 欧洲凯尔特股份有限公司 | 作为钠通道阻滞剂的芳基取代的吡唑、三唑和四唑化合物 |
WO2002055502A1 (en) * | 2001-01-02 | 2002-07-18 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine derivatives useful as cyclooxygenase inhibitor |
US20030105144A1 (en) | 2001-04-17 | 2003-06-05 | Ping Gao | Stabilized oral pharmaceutical composition |
US6673818B2 (en) | 2001-04-20 | 2004-01-06 | Pharmacia Corporation | Fluoro-substituted benzenesulfonyl compounds for the treatment of inflammation |
AU2002313633B2 (en) * | 2001-06-08 | 2007-03-01 | Cytovia, Inc. | Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs |
EP1273582B1 (en) | 2001-07-05 | 2005-06-29 | Pfizer Products Inc. | Heterocyclo-alkylsulfonyl pyrazoles as anti-inflammatory/analgesic agents |
US7076539B2 (en) * | 2001-07-30 | 2006-07-11 | Hewlett-Packard Development Company, L.P. | Network connectivity establishment at user log-in |
US6849653B2 (en) * | 2001-09-19 | 2005-02-01 | Pharmacia Corporation | Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation |
CA2460942A1 (en) * | 2001-09-19 | 2003-03-27 | Pharmacia Corporation | Substituted pyrazolyl compounds for the treatment of inflammation |
KR100697482B1 (ko) | 2001-09-25 | 2007-03-20 | 파마시아 코포레이션 | 치환된 피라졸의 제조 방법 |
US7057049B2 (en) * | 2001-09-25 | 2006-06-06 | Pharmacia Corporation | Process for making substituted pyrazoles |
GT200200183A (es) | 2001-09-28 | 2003-05-23 | Procedimiento para preparar derivados de heterocicloalquilsulfonil pirazol | |
WO2003037336A1 (en) | 2001-11-02 | 2003-05-08 | Pfizer Products Inc. | 1-(5-sulfonyl-pyridin-2-yl)-5-(methylidene-cycloalkylmethoxy)-1h-pyrazole-4-carbonitrile derivatives and other compounds as cyclooxygenase inhibitors for the treatment of arthritis, neurodegeneration and colon cancer |
DE60231439D1 (de) | 2001-12-06 | 2009-04-16 | Merck & Co Inc | Mitotische kinesinhemmer |
CA2477931C (en) * | 2002-03-05 | 2011-02-01 | Josef Ehrenfreund | O-cyclopropyl-carboxanilides and their use as fungicides |
EP1492487B1 (en) * | 2002-03-08 | 2009-11-11 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
AR038967A1 (es) * | 2002-03-18 | 2005-02-02 | Solvay Pharm Bv | Derivados de 2,3 - diaril - pirazolidinas como inhibidores de enzimas que degradan la neurotensina |
US7329401B2 (en) * | 2002-04-15 | 2008-02-12 | The Regents Of The University Of California | Cyclooxygenase-2 selective agents useful as imaging probes and related methods |
KR20050013553A (ko) | 2002-05-24 | 2005-02-04 | 파마시아 코포레이션 | 디아릴 피라졸의 합성 |
MXPA04012642A (es) | 2002-06-14 | 2005-03-23 | Merck & Co Inc | Inhibidores de la cinesina mitotica. |
JP2005535642A (ja) * | 2002-06-28 | 2005-11-24 | ニトロメッド インコーポレーティッド | オキシムおよび/またはヒドラゾンを含有するニトロソ化および/またはニトロシル化シクロオキシゲナーゼ−2選択的阻害剤、組成物、および使用方法 |
WO2004016592A1 (en) * | 2002-08-14 | 2004-02-26 | Ppd Discovery, Inc. | Prenylation inhibitors and methods of their synthesis and use |
WO2004016741A2 (en) * | 2002-08-14 | 2004-02-26 | Ppd Discovery, Inc. | Prenylation inhibitors containing dimethyl-cyclobutane and methods of their synthesis and use |
US6649638B1 (en) * | 2002-08-14 | 2003-11-18 | Ppd Discovery, Inc. | Prenylation inhibitors and methods of their synthesis and use |
BR0314872A (pt) * | 2002-10-18 | 2005-08-02 | Pfizer Prod Inc | Ligandos do receptor canabinóide e usos dos mesmos |
US7129239B2 (en) * | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
US7183306B2 (en) * | 2002-12-02 | 2007-02-27 | Astellas Pharma Inc. | Pyrazole derivatives |
US7247628B2 (en) * | 2002-12-12 | 2007-07-24 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
EP1581213A4 (en) * | 2002-12-18 | 2008-11-19 | Cytovia Inc | 3,5-DISUBSTITUES-1,2,4-OXADIAZOLES AND ANALOGS AS ACTIVATORS OF CASPASES AND APOPTOSIS PROMOTERS, AND USE THEREOF |
US7329658B2 (en) * | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
ZA200505734B (en) * | 2003-02-07 | 2006-12-27 | Daiichi Seiyaku Co | Pyrazole Derivative |
JPWO2004069824A1 (ja) * | 2003-02-07 | 2006-05-25 | 第一製薬株式会社 | ピラゾール誘導体 |
US7176210B2 (en) * | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
US7141669B2 (en) * | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands and uses thereof |
US7268133B2 (en) * | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
US20040214856A1 (en) * | 2003-04-23 | 2004-10-28 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
US7145012B2 (en) * | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
JP4041153B2 (ja) * | 2003-05-07 | 2008-01-30 | ファイザー・プロダクツ・インク | カンナビノイド受容体リガンドとその使用 |
US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
US20040259887A1 (en) * | 2003-06-18 | 2004-12-23 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
EP1656146A4 (en) | 2003-08-15 | 2009-04-15 | Merck & Co Inc | INHIBITORS OF MITOTIC KINESIN |
AU2004264533B2 (en) | 2003-08-15 | 2009-01-22 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
US20060079566A1 (en) * | 2003-10-03 | 2006-04-13 | Ching-Shih Chen | PDK-1/Akt signaling inhibitors |
JP2007084437A (ja) * | 2003-12-26 | 2007-04-05 | Dai Ichi Seiyaku Co Ltd | アミノアルキルピラゾール誘導体 |
TW200526641A (en) * | 2003-12-26 | 2005-08-16 | Daiichi Seiyaku Co | Amidopyrazole derivatives |
CA2571824A1 (en) * | 2004-07-01 | 2006-01-19 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
MXPA06015275A (es) | 2004-07-01 | 2007-03-15 | Merck & Co Inc | Inhibidores de quinasa mitotica. |
JP2008505089A (ja) * | 2004-07-01 | 2008-02-21 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
JP2008505090A (ja) * | 2004-07-01 | 2008-02-21 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤のプロドラッグ |
EP1785418A4 (en) * | 2004-08-06 | 2009-11-11 | Daiichi Seiyaku Co | PYRAZOLE DERIVATIVE |
CN101072769A (zh) * | 2004-08-06 | 2007-11-14 | 第一制药株式会社 | 抗血小板药及其制造方法 |
US7629373B2 (en) * | 2005-04-07 | 2009-12-08 | Merck & Co. Inc. | Mitotic kinesin inhibitors |
WO2006123182A2 (en) | 2005-05-17 | 2006-11-23 | Merck Sharp & Dohme Limited | Cyclohexyl sulphones for treatment of cancer |
EP1928859A1 (en) * | 2005-06-17 | 2008-06-11 | Carex SA | Pyrazole derivates as cannabinoid receptor modulators |
KR101363278B1 (ko) * | 2005-06-27 | 2014-02-21 | 엑셀리시스 페이턴트 컴퍼니 엘엘씨 | 이미다졸계 lxr 변조제 |
TW200804345A (en) * | 2005-08-30 | 2008-01-16 | Novartis Ag | Substituted benzimidazoles and methods of preparation |
US20090062302A1 (en) | 2006-01-24 | 2009-03-05 | Buser-Doepner Carolyn A | Jak2 Tyrosine Kinase Inhibition |
GB0603041D0 (en) | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
PL2010528T3 (pl) | 2006-04-19 | 2018-03-30 | Novartis Ag | 6-0-podstawione związki benzoksazolowe i benzotiazolowe i sposoby hamowania sygnalizacji csf-1r |
EP2946778A1 (en) | 2006-09-22 | 2015-11-25 | Merck Sharp & Dohme Corp. | Method of treatment using fatty acid synthesis inhibitors |
EP2097410A4 (en) * | 2006-09-29 | 2009-11-25 | Green Cross Corp | HETEROYL-PYRAZOLE DERIVATIVES AS CANNABINOID CB1 RECEPTOR ANTAGONISTS |
US20110218176A1 (en) | 2006-11-01 | 2011-09-08 | Barbara Brooke Jennings-Spring | Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development |
EP2109608B1 (en) | 2007-01-10 | 2011-03-23 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Amide substituted indazoles as poly(adp-ribose)polymerase (parp) inhibitors |
CA2676413A1 (en) * | 2007-01-19 | 2008-07-31 | Mallinckrodt Inc. | Diagnostic and therapeutic cyclooxygenase-2 binding ligands |
US20080207704A1 (en) * | 2007-02-27 | 2008-08-28 | The Green Cross Corporation | Heteroaryl-imidazole derivatives as cannabinoid cb1 receptor antagonists |
EA019951B1 (ru) | 2007-03-01 | 2014-07-30 | Новартис Аг | Ингибиторы киназы pim и способы их применения |
US20100120839A1 (en) * | 2007-04-20 | 2010-05-13 | Biolipox Ab | Pyrazoles useful in the treatment of inflammation |
KR20100017866A (ko) | 2007-05-21 | 2010-02-16 | 노파르티스 아게 | Csf-1r 억제제, 조성물 및 사용 방법 |
WO2008145257A1 (en) * | 2007-05-31 | 2008-12-04 | Syngenta Participations Ag | Process for the production of pyrazoles |
EP3103791B1 (en) | 2007-06-27 | 2018-01-31 | Merck Sharp & Dohme Corp. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
US8039502B2 (en) | 2007-07-24 | 2011-10-18 | The Ohio State University Research Foundation | Anti-infective agents against intracellular pathogens |
US7977358B2 (en) * | 2007-07-26 | 2011-07-12 | Hoffmann-La Roche Inc. | Pyrazol derivatives |
CN101854933A (zh) | 2007-09-10 | 2010-10-06 | 钙医学公司 | 调节细胞内钙的化合物 |
US20110009463A1 (en) * | 2007-10-17 | 2011-01-13 | Yuri Karl Petersson | Geranylgeranyl transferase inhibitors and methods of making and using the same |
WO2009078498A1 (en) * | 2007-12-17 | 2009-06-25 | Green Cross Corporation | Biarylpyrazole 4-carboxamides as cannabinoid cb1 receptor ligands |
JP5581219B2 (ja) | 2008-01-25 | 2014-08-27 | ミレニアム ファーマシューティカルズ, インコーポレイテッド | チオフェンおよびホスファチジルイノシトール3−キナーゼ(pi3k)阻害薬としてのその使用 |
WO2009111354A2 (en) | 2008-03-03 | 2009-09-11 | Tiger Pharmatech | Tyrosine kinase inhibitors |
DE102008015032A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte Pyrazolamide und ihre Verwendung |
DE102008015033A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
DK2684873T3 (en) * | 2008-06-09 | 2019-04-01 | Univ Muenchen Ludwig Maximilians | PHARMACEUTICALS FOR INHIBITING AGGREGATION OF PROTEINS INVOLVED IN DISEASES CONNECTED WITH PROTEIN AGGREGATION AND / OR NEURODEGENERATIVE DISEASE |
US20110144056A1 (en) * | 2008-06-11 | 2011-06-16 | Lin Linus S | Pyrazole derivatives useful as inhibitors of faah |
EP2321303B1 (en) | 2008-08-27 | 2019-11-27 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
DE102008062863A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung |
DE102008062878A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte Furancarboxamide und ihre Verwendung |
US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
CA2750935A1 (en) | 2009-01-30 | 2010-08-12 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
US20120108823A1 (en) | 2009-04-22 | 2012-05-03 | The Ohio State University Research Foundation | Anti-francisella agents |
DE102009036604A1 (de) | 2009-07-30 | 2011-02-03 | Aicuris Gmbh & Co. Kg | Substituierte Bis-Arylpyrazolamide mit terminaler primärer Amidfunktionalisierung und ihre Verwendung |
CN104945382B (zh) | 2009-10-14 | 2020-02-07 | 默沙东公司 | 提高p53活性的取代的哌啶和其用途 |
AU2011248579A1 (en) | 2010-04-27 | 2012-11-29 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
ES2591004T3 (es) | 2010-04-27 | 2016-11-24 | Calcimedica, Inc. | Compuestos moduladores del calcio intracelular |
US8999957B2 (en) | 2010-06-24 | 2015-04-07 | Merck Sharp & Dohme Corp. | Heterocyclic compounds as ERK inhibitors |
JP6043285B2 (ja) | 2010-08-02 | 2016-12-14 | サーナ・セラピューティクス・インコーポレイテッドSirna Therapeutics,Inc. | 低分子干渉核酸(siNA)を用いたカテニン(カドヘリン結合型タンパク質)β1(CTNNB1)遺伝子発現のRNA干渉媒介性阻害 |
WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
NZ607087A (en) | 2010-08-11 | 2015-05-29 | Millennium Pharm Inc | Heteroaryls as inhibitors of pi3k and for the treatment of proliferative, inflammatory, or cardiovascular disorders |
WO2012021615A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
CN108676800B (zh) | 2010-08-17 | 2022-11-11 | 瑟纳治疗公司 | 使用短干扰核酸(siNA)的乙型肝炎病毒(HBV)基因表达的RNA干扰介导的抑制 |
EP2608669B1 (en) | 2010-08-23 | 2016-06-22 | Merck Sharp & Dohme Corp. | NOVEL PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS |
CN103180316A (zh) | 2010-08-27 | 2013-06-26 | 钙医学公司 | 调节细胞内钙的化合物 |
US8580805B2 (en) * | 2010-08-31 | 2013-11-12 | Hubert Maehr | Pyrimidine carboxamide derivatives |
EP2613782B1 (en) | 2010-09-01 | 2016-11-02 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as erk inhibitors |
US9242981B2 (en) | 2010-09-16 | 2016-01-26 | Merck Sharp & Dohme Corp. | Fused pyrazole derivatives as novel ERK inhibitors |
SG189396A1 (en) | 2010-10-13 | 2013-05-31 | Millennium Pharm Inc | Heteroaryls and uses thereof |
ES2663009T3 (es) | 2010-10-29 | 2018-04-10 | Sirna Therapeutics, Inc. | Inhibición de la expresión génica mediada por interferencia por ARN utilizando ácidos nucleicos de interferencia cortos (ANic) |
EP2654748B1 (en) | 2010-12-21 | 2016-07-27 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as erk inhibitors |
CN103732592A (zh) | 2011-04-21 | 2014-04-16 | 默沙东公司 | 胰岛素样生长因子-1受体抑制剂 |
WO2013063214A1 (en) | 2011-10-27 | 2013-05-02 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
US9221809B2 (en) | 2011-10-31 | 2015-12-29 | Merck Sharp & Dohme Corp. | Aminopyrimidinones as interleukin receptor-associated kinase inhibitors |
DE102011055815A1 (de) | 2011-11-29 | 2013-05-29 | Aicuris Gmbh & Co. Kg | Carboxamid-substituierte Heteroaryl-Pyrazole und ihre Verwendung |
UY34538A (es) * | 2011-12-23 | 2013-06-28 | Millennium Pharm Inc | Heteroarilos y usos de los mismos |
EP3358013B1 (en) | 2012-05-02 | 2020-06-24 | Sirna Therapeutics, Inc. | Short interfering nucleic acid (sina) compositions |
CA2880542C (en) * | 2012-07-30 | 2018-01-02 | The Ohio State University | Antibacterial protein kinase inhibitors |
DE102012016908A1 (de) | 2012-08-17 | 2014-02-20 | Aicuris Gmbh & Co. Kg | Tris-(Hetero)Aryl-Pyrazole und ihre Verwendung |
CN105050598B (zh) | 2012-09-28 | 2018-04-27 | 默沙东公司 | 作为erk抑制剂的新型化合物 |
US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
CA2892361A1 (en) | 2012-11-28 | 2014-06-05 | Merck Sharp & Dohme Corp. | Use of a wee1 inhibitor for treating a cancer characterized by low pkmyt1 expression levels |
AU2013361694B2 (en) | 2012-12-20 | 2017-10-26 | Merck Sharp & Dohme Corp. | Substituted imidazopyridines as HDM2 inhibitors |
WO2014120748A1 (en) | 2013-01-30 | 2014-08-07 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as hdm2 inhibitors |
CN103265537B (zh) * | 2013-05-14 | 2015-05-27 | 浙江医药高等专科学校 | 抗肿瘤化合物、其制备方法和用途 |
US20160166576A1 (en) | 2013-07-11 | 2016-06-16 | Merck Sharp & Dohme Corp. | Substituted amidopyrazole inhibitors of interleukin receptor-associated kinases (irak-4) |
EP3027605B1 (en) | 2013-07-31 | 2017-11-08 | Council of Scientific & Industrial Research | Novel indazole compounds and a process for the preparation thereof |
EP3041938A1 (en) | 2013-09-03 | 2016-07-13 | Moderna Therapeutics, Inc. | Circular polynucleotides |
US9611263B2 (en) | 2013-10-08 | 2017-04-04 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
JO3589B1 (ar) | 2014-08-06 | 2020-07-05 | Novartis Ag | مثبطات كيناز البروتين c وطرق استخداماتها |
KR101650476B1 (ko) * | 2015-02-06 | 2016-08-23 | 한국건설기술연구원 | 중공슬래브를 위한 중공체의 부력방지장치 |
EP3267996B1 (en) | 2015-03-12 | 2020-11-11 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidine inhibitors of irak4 activity |
WO2016144849A1 (en) | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Thienopyrazine inhibitors of irak4 activity |
WO2016144844A1 (en) | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Carboxamide inhibitors of irak4 activity |
EP3525785A4 (en) | 2016-10-12 | 2020-03-25 | Merck Sharp & Dohme Corp. | KDM5 INHIBITORS |
AR112900A1 (es) * | 2017-09-13 | 2019-12-26 | Hanmi Pharm Ind Co Ltd | Compuesto derivado de pirazol y uso de este |
WO2019094311A1 (en) | 2017-11-08 | 2019-05-16 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
US11981701B2 (en) | 2018-08-07 | 2024-05-14 | Merck Sharp & Dohme Llc | PRMT5 inhibitors |
WO2020033282A1 (en) | 2018-08-07 | 2020-02-13 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
CN115087638B (zh) | 2019-12-17 | 2023-11-24 | 默沙东公司 | Prmt5抑制剂 |
CN112961109B (zh) * | 2021-01-27 | 2022-05-17 | 台州学院 | 一种1,4-双磺酰化的全取代吡唑类化合物及其制备和应用 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4146721A (en) | 1969-09-12 | 1979-03-27 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pyrazol-4-acetic acid compounds |
DE2536003C2 (de) * | 1975-08-08 | 1985-11-14 | Schering AG, 1000 Berlin und 4709 Bergkamen | Pyrazol-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Derivate |
DE2906252A1 (de) * | 1979-02-19 | 1980-08-28 | Merck Patent Gmbh | Pyrazolderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
CA1130808A (en) * | 1979-10-05 | 1982-08-31 | Ronald G. Micetich | 3-(or 5-) trifluoromethyl-1-aryl pyrazoles |
JPS58177977A (ja) * | 1982-04-09 | 1983-10-18 | Grelan Pharmaceut Co Ltd | 4−フエニルピラゾ−ル類 |
ATE49198T1 (de) * | 1984-05-12 | 1990-01-15 | Fisons Plc | Antiinflammatorische 1,n-diarylpyrazol-3-amine, deren zusammensetzungen und verfahren zu deren herstellung. |
JPS6140266A (ja) * | 1984-08-01 | 1986-02-26 | Morishita Seiyaku Kk | ピラゾ−ル誘導体 |
US4826868A (en) * | 1986-05-29 | 1989-05-02 | Ortho Pharmaceutical Corporation | 1,5-Diaryl-3-substituted pyrazoles pharmaceutical compositions and use |
EP0268554B1 (de) * | 1986-10-22 | 1991-12-27 | Ciba-Geigy Ag | 1,5-Diphenylpyrazol-3-carbonsäurederivate zum Schützen von Kulturpflanzen |
EP0272704A3 (en) * | 1986-12-26 | 1990-11-22 | Sanwa Kagaku Kenkyusho Co., Ltd. | Use of pyrazole derivatives in the treatment of immunity diseases and nephropathy |
JPS6425763A (en) * | 1987-04-24 | 1989-01-27 | Mitsubishi Chem Ind | Pyrazoles and insecticide and acaricide containing said pyrazoles as active ingredient |
AU611437B2 (en) * | 1987-05-29 | 1991-06-13 | Ortho Pharmaceutical Corporation | Pharmacologically active 2- and 3-substituted (1',5'-diaryl-3-pyrazolyl)-n-hydroxypropanamides and method for synthesizing the same |
JPH089541B2 (ja) * | 1988-03-07 | 1996-01-31 | 三井東圧化学株式会社 | ピラゾール類を主成分とする脳浮腫抑制剤 |
-
1990
- 1990-09-11 PH PH41179A patent/PH27357A/en unknown
- 1990-09-13 IL IL9567590A patent/IL95675A/en not_active IP Right Cessation
- 1990-09-14 US US07/582,358 patent/US5134142A/en not_active Expired - Lifetime
- 1990-09-18 CA CA002025599A patent/CA2025599C/en not_active Expired - Fee Related
- 1990-09-18 IE IE337990A patent/IE68857B1/en not_active IP Right Cessation
- 1990-09-19 HU HU905970A patent/HU208122B/hu not_active IP Right Cessation
- 1990-09-19 EP EP90117983A patent/EP0418845B1/en not_active Expired - Lifetime
- 1990-09-19 ES ES90117983T patent/ES2088933T3/es not_active Expired - Lifetime
- 1990-09-19 DK DK90117983.8T patent/DK0418845T3/da active
- 1990-09-19 AT AT90117983T patent/ATE126216T1/de not_active IP Right Cessation
- 1990-09-19 FI FI904602A patent/FI102535B/fi not_active IP Right Cessation
- 1990-09-19 DE DE69021472T patent/DE69021472T2/de not_active Expired - Fee Related
- 1990-09-20 JP JP2252319A patent/JP2586713B2/ja not_active Expired - Fee Related
- 1990-09-21 CN CN90107130A patent/CN1046506C/zh not_active Expired - Fee Related
- 1990-09-21 NO NO904134A patent/NO301006B1/no not_active IP Right Cessation
- 1990-09-21 PT PT95389A patent/PT95389B/pt not_active IP Right Cessation
- 1990-09-21 KR KR1019900015110A patent/KR0182798B1/ko not_active IP Right Cessation
- 1990-09-21 RU SU4831230/04A patent/RU2021990C1/ru not_active IP Right Cessation
- 1990-09-21 AU AU63072/90A patent/AU637142B2/en not_active Ceased
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1991
- 1991-12-02 RU SU915010250A patent/RU2059622C1/ru active
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1995
- 1995-06-22 HU HU95P/P00344P patent/HU211532A9/hu unknown
- 1995-08-10 GR GR950402078T patent/GR3017100T3/el unknown
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