CN112566901A - 作为RORγt的调节剂的苯基取代的吡唑类 - Google Patents
作为RORγt的调节剂的苯基取代的吡唑类 Download PDFInfo
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- CN112566901A CN112566901A CN201980054161.XA CN201980054161A CN112566901A CN 112566901 A CN112566901 A CN 112566901A CN 201980054161 A CN201980054161 A CN 201980054161A CN 112566901 A CN112566901 A CN 112566901A
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- Prior art keywords
- alkyl
- ethyl
- pyrazole
- bromo
- nhc
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 144
- 238000000034 method Methods 0.000 claims abstract description 86
- 201000010099 disease Diseases 0.000 claims abstract description 80
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 15
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims abstract description 12
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims abstract description 12
- 230000001404 mediated effect Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 195
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 177
- 201000006417 multiple sclerosis Diseases 0.000 claims description 110
- 125000001153 fluoro group Chemical group F* 0.000 claims description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 239000003814 drug Substances 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 208000006673 asthma Diseases 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 155
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- 239000012141 concentrate Substances 0.000 description 35
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 35
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 35
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 32
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 29
- 229920006395 saturated elastomer Polymers 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
- 238000011282 treatment Methods 0.000 description 27
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- 239000003153 chemical reaction reagent Substances 0.000 description 26
- 125000004093 cyano group Chemical group *C#N 0.000 description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- HMPFIGZCHPKESX-UHFFFAOYSA-N ethyl 4-chloro-5-[2-(difluoromethoxy)-4-(3,3,3-trifluoro-2,2-dimethylpropyl)phenyl]-1-ethylpyrazole-3-carboxylate Chemical compound ClC=1C(=NN(C=1C1=C(C=C(C=C1)CC(C(F)(F)F)(C)C)OC(F)F)CC)C(=O)OCC HMPFIGZCHPKESX-UHFFFAOYSA-N 0.000 description 25
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 25
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 22
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 21
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 20
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 19
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
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- QMEMCJVHDBMFHH-UHFFFAOYSA-N ethyl 4-[4-bromo-2-(trifluoromethoxy)phenyl]-2,4-dioxobutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=C(Br)C=C1OC(F)(F)F QMEMCJVHDBMFHH-UHFFFAOYSA-N 0.000 description 13
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- 239000001257 hydrogen Substances 0.000 description 10
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- PMWVVXDDEDPHSV-UHFFFAOYSA-N 9-(3,3,3-trifluoropropyl)-9-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1B2CCC(F)(F)F PMWVVXDDEDPHSV-UHFFFAOYSA-N 0.000 description 7
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- ICJYWDHNTMJKFP-UHFFFAOYSA-N ethyl 1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C=1C=CNC=1 ICJYWDHNTMJKFP-UHFFFAOYSA-N 0.000 description 7
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- PADIIRFFGXSJCE-UHFFFAOYSA-N ethyl 4-chloro-5-[2-(difluoromethoxy)-4-(3,3,3-trifluoro-2,2-dimethylpropanoyl)phenyl]-1-ethylpyrazole-3-carboxylate Chemical compound ClC=1C(=NN(C=1C1=C(C=C(C=C1)C(C(C(F)(F)F)(C)C)=O)OC(F)F)CC)C(=O)OCC PADIIRFFGXSJCE-UHFFFAOYSA-N 0.000 description 1
- XLAAKVSCPZYORV-UHFFFAOYSA-N ethyl 4-chloro-5-[2-(difluoromethoxy)-4-(3,3,3-trifluoro-2,2-dimethylpropyl)phenyl]-1-methylpyrazole-3-carboxylate Chemical compound ClC=1C(=NN(C=1C1=C(C=C(C=C1)CC(C(F)(F)F)(C)C)OC(F)F)C)C(=O)OCC XLAAKVSCPZYORV-UHFFFAOYSA-N 0.000 description 1
- AIAGVFPITPDHTM-UHFFFAOYSA-N ethyl 4-chloro-5-[2-(difluoromethoxy)-4-(3,3,3-trifluoropropyl)phenyl]-1-ethylpyrazole-3-carboxylate Chemical compound ClC=1C(=NN(C=1C1=C(C=C(C=C1)CCC(F)(F)F)OC(F)F)CC)C(=O)OCC AIAGVFPITPDHTM-UHFFFAOYSA-N 0.000 description 1
- KWVGSBODFUOWND-UHFFFAOYSA-N ethyl 4-chloro-5-[2-(difluoromethoxy)-4-(4,4,4-trifluoro-1-hydroxybutyl)phenyl]-1-ethylpyrazole-3-carboxylate Chemical compound ClC=1C(=NN(C=1C1=C(C=C(C=C1)C(CCC(F)(F)F)O)OC(F)F)CC)C(=O)OCC KWVGSBODFUOWND-UHFFFAOYSA-N 0.000 description 1
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- LHKJRAOQZWMSAJ-UHFFFAOYSA-N ethyl 4-chloro-5-[2-(difluoromethoxy)-4-(5,5,5-trifluoro-2-hydroxypentan-2-yl)phenyl]-1-ethylpyrazole-3-carboxylate Chemical compound ClC=1C(=NN(C=1C1=C(C=C(C=C1)C(C)(CCC(F)(F)F)O)OC(F)F)CC)C(=O)OCC LHKJRAOQZWMSAJ-UHFFFAOYSA-N 0.000 description 1
- YAYGJQWEQBKGBH-SECBINFHSA-N ethyl 4-chloro-5-[2-(difluoromethoxy)-4-[(2R)-3,3,3-trifluoro-2-methylpropyl]phenyl]-1-methylpyrazole-3-carboxylate Chemical compound ClC=1C(=NN(C=1C1=C(C=C(C=C1)C[C@H](C(F)(F)F)C)OC(F)F)C)C(=O)OCC YAYGJQWEQBKGBH-SECBINFHSA-N 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
- 102000054765 polymorphisms of proteins Human genes 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 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
- 229960000948 quinine Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 201000000306 sarcoidosis Diseases 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
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- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
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- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- CESUXLKAADQNTB-UHFFFAOYSA-N tert-butanesulfinamide Chemical compound CC(C)(C)S(N)=O CESUXLKAADQNTB-UHFFFAOYSA-N 0.000 description 1
- UIYOVVYZPVVUMJ-UHFFFAOYSA-N tert-butyl carbamoyl carbonate Chemical compound CC(C)(C)OC(=O)OC(N)=O UIYOVVYZPVVUMJ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DDPWVABNMBRBFI-UHFFFAOYSA-N tert-butylhydrazine;hydron;chloride Chemical compound Cl.CC(C)(C)NN DDPWVABNMBRBFI-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 238000006692 trifluoromethylation reaction Methods 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
-
- 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
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D403/10—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 linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862686308P | 2018-06-18 | 2018-06-18 | |
| US62/686308 | 2018-06-18 | ||
| PCT/IB2019/055043 WO2019243999A1 (en) | 2018-06-18 | 2019-06-17 | Phenyl substituted pyrazoles as modulators of roryt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112566901A true CN112566901A (zh) | 2021-03-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980054161.XA Pending CN112566901A (zh) | 2018-06-18 | 2019-06-17 | 作为RORγt的调节剂的苯基取代的吡唑类 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10975037B2 (https=) |
| EP (1) | EP3790865A1 (https=) |
| JP (1) | JP2021528405A (https=) |
| CN (1) | CN112566901A (https=) |
| CA (1) | CA3103929A1 (https=) |
| WO (1) | WO2019243999A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115894374A (zh) * | 2023-02-16 | 2023-04-04 | 广州佳途科技股份有限公司 | 一种氟甲腈的制备方法及其应用 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201803869A (zh) | 2016-04-27 | 2018-02-01 | 健生藥品公司 | 作為RORγT調節劑之6-胺基吡啶-3-基噻唑 |
| ES2925473T3 (es) | 2018-06-18 | 2022-10-18 | Janssen Pharmaceutica Nv | Pirazoles de piridinilo como moduladores de RORyt |
| CA3103770A1 (en) | 2018-06-18 | 2019-12-26 | Janssen Pharmaceutica Nv | Phenyl and pyridinyl substituted imidazoles as modulators of roryt |
| EP3806958B1 (en) | 2018-06-18 | 2022-09-07 | Janssen Pharmaceutica NV | 6-aminopyridin-3-yl pyrazoles as modulators of roryt |
| JP2021528405A (ja) | 2018-06-18 | 2021-10-21 | ヤンセン ファーマシューティカ エヌ.ベー. | RORγtのモジュレータとしてのアミド置換チアゾール |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080021030A1 (en) * | 2003-11-17 | 2008-01-24 | Faucher Nicolas E | Substituted Pyrazoles As Ppar Agonists |
| WO2012174362A1 (en) * | 2011-06-17 | 2012-12-20 | Research Triangle Institute | Pyrazole derivatives as cannabinoid receptor 1 antagonists |
| WO2014023367A1 (en) * | 2012-08-09 | 2014-02-13 | Phenex Pharmaceuticals Ag | Carboxamide or sulfonamide substituted nitrogen-containing 5-membered heterocycles as modulators for the orphan nuclear receptor ror gamma |
| CN108026050A (zh) * | 2015-08-03 | 2018-05-11 | 格兰马克药品股份有限公司 | 作为RORγ调节剂的新型化合物 |
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| CA3103929A1 (en) | 2019-12-26 |
| EP3790865A1 (en) | 2021-03-17 |
| WO2019243999A1 (en) | 2019-12-26 |
| JP2021528405A (ja) | 2021-10-21 |
| US10975037B2 (en) | 2021-04-13 |
| US20190382349A1 (en) | 2019-12-19 |
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