JP2017512184A5 - - Google Patents
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- JP2017512184A5 JP2017512184A5 JP2016548682A JP2016548682A JP2017512184A5 JP 2017512184 A5 JP2017512184 A5 JP 2017512184A5 JP 2016548682 A JP2016548682 A JP 2016548682A JP 2016548682 A JP2016548682 A JP 2016548682A JP 2017512184 A5 JP2017512184 A5 JP 2017512184A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- alkyl
- thiazole
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims 294
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 250
- 125000001072 heteroaryl group Chemical group 0.000 claims 165
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 150
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 142
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 118
- 125000001424 substituent group Chemical group 0.000 claims 109
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 99
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 93
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 75
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 60
- 125000005843 halogen group Chemical group 0.000 claims 57
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 49
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 47
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims 39
- 125000005842 heteroatom Chemical group 0.000 claims 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 35
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 29
- 229910052757 nitrogen Inorganic materials 0.000 claims 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 27
- 150000003839 salts Chemical class 0.000 claims 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 25
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 25
- 125000002393 azetidinyl group Chemical group 0.000 claims 24
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 24
- 125000006413 ring segment Chemical group 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 150000002367 halogens Chemical class 0.000 claims 22
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 22
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 18
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 125000004076 pyridyl group Chemical group 0.000 claims 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 15
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 15
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 14
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 241001024304 Mino Species 0.000 claims 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 9
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 9
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 7
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 150000003857 carboxamides Chemical class 0.000 claims 7
- 125000001188 haloalkyl group Chemical group 0.000 claims 7
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 7
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 7
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 6
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 6
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- AKWIAIDKXNKXDI-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C=CNC=1 AKWIAIDKXNKXDI-UHFFFAOYSA-N 0.000 claims 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims 4
- 206010027476 Metastases Diseases 0.000 claims 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 4
- 230000010261 cell growth Effects 0.000 claims 4
- 230000004663 cell proliferation Effects 0.000 claims 4
- 230000001413 cellular effect Effects 0.000 claims 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 230000028709 inflammatory response Effects 0.000 claims 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 230000004083 survival effect Effects 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- OAYDAYANSPNWIN-LBPRGKRZSA-N N-[4-fluoro-3-[(3S)-pyrrolidin-3-yl]oxyphenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)O[C@@H]1CNCC1 OAYDAYANSPNWIN-LBPRGKRZSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 150000004677 hydrates Chemical class 0.000 claims 3
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 3
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 2
- NJGOHBDZYCSHBW-UHFFFAOYSA-N 3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-N-[6-[1-(3,3,3-trifluoropropyl)piperidin-4-yl]oxypyridin-3-yl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC=1C=NC(=CC=1)OC1CCN(CC1)CCC(F)(F)F)NC1=NC=C(N=C1)C(F)(F)F NJGOHBDZYCSHBW-UHFFFAOYSA-N 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims 2
- 208000009849 Female Genital Neoplasms Diseases 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 206010059282 Metastases to central nervous system Diseases 0.000 claims 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 2
- VBXRRJSFDOEFSX-UHFFFAOYSA-N N-[3-[[1-(2,2-difluoroethyl)piperidin-3-yl]methoxy]-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CC(CCC1)COC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F VBXRRJSFDOEFSX-UHFFFAOYSA-N 0.000 claims 2
- 206010029098 Neoplasm skin Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 230000024932 T cell mediated immunity Effects 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 2
- 210000000481 breast Anatomy 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 201000011523 endocrine gland cancer Diseases 0.000 claims 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- 230000028993 immune response Effects 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 208000037841 lung tumor Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 208000023958 prostate neoplasm Diseases 0.000 claims 2
- 201000004477 skin sarcoma Diseases 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 210000003932 urinary bladder Anatomy 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- XDRYHXLJJWHBCN-UHFFFAOYSA-N 3-[[3-methyl-5-(quinoxalin-2-ylamino)-1,2-thiazole-4-carbonyl]amino]benzoic acid Chemical compound CC1=NSC(=C1C(=O)NC=1C=C(C(=O)O)C=CC=1)NC1=NC2=CC=CC=C2N=C1 XDRYHXLJJWHBCN-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- AVSOHPILRRVFRV-UHFFFAOYSA-N 3-methyl-5-(quinoxalin-2-ylamino)-N-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC1=CC(=CC=C1)NC(C(F)(F)F)=O)NC1=NC2=CC=CC=C2N=C1 AVSOHPILRRVFRV-UHFFFAOYSA-N 0.000 claims 1
- BVLYUXFWPBPVIV-UHFFFAOYSA-N 3-methyl-5-(quinoxalin-2-ylamino)-N-[3-[[1-(2,2,2-trifluoroethyl)azetidin-3-yl]sulfonylamino]phenyl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC1=CC(=CC=C1)NS(=O)(=O)C1CN(C1)CC(F)(F)F)NC1=NC2=CC=CC=C2N=C1 BVLYUXFWPBPVIV-UHFFFAOYSA-N 0.000 claims 1
- SXSQPQVLHLLMCX-UHFFFAOYSA-N 3-methyl-5-(quinoxalin-2-ylamino)-N-[3-[[1-(2,2,2-trifluoroethyl)piperidin-4-yl]sulfonylamino]phenyl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC1=CC(=CC=C1)NS(=O)(=O)C1CCN(CC1)CC(F)(F)F)NC1=NC2=CC=CC=C2N=C1 SXSQPQVLHLLMCX-UHFFFAOYSA-N 0.000 claims 1
- FIFOVITXIIVXAF-UHFFFAOYSA-N 3-methyl-5-(quinoxalin-2-ylamino)-N-[3-[[1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]sulfonylamino]phenyl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC1=CC(=CC=C1)NS(=O)(=O)C1CN(CC1)CC(F)(F)F)NC1=NC2=CC=CC=C2N=C1 FIFOVITXIIVXAF-UHFFFAOYSA-N 0.000 claims 1
- UVIHBLWILJHPDQ-UHFFFAOYSA-N 3-methyl-5-(quinoxalin-2-ylamino)-N-[3-[[1-(3,3,3-trifluoropropyl)azetidin-3-yl]sulfonylamino]phenyl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC1=CC(=CC=C1)NS(=O)(=O)C1CN(C1)CCC(F)(F)F)NC1=NC2=CC=CC=C2N=C1 UVIHBLWILJHPDQ-UHFFFAOYSA-N 0.000 claims 1
- NGWYPFJVSMIAOI-UHFFFAOYSA-N 3-methyl-5-(quinoxalin-2-ylamino)-N-[4-[4-(2,2,2-trifluoroethyl)-1,4-diazepane-1-carbonyl]phenyl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC1=CC=C(C=C1)C(=O)N1CCN(CCC1)CC(F)(F)F)NC1=NC2=CC=CC=C2N=C1 NGWYPFJVSMIAOI-UHFFFAOYSA-N 0.000 claims 1
- QLXRJPGSFHNUMU-UHFFFAOYSA-N 3-methyl-5-(quinoxalin-2-ylamino)-N-[6-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]oxypyridin-3-yl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC=1C=NC(=CC=1)OC1CCN(CC1)CC(F)(F)F)NC1=NC2=CC=CC=C2N=C1 QLXRJPGSFHNUMU-UHFFFAOYSA-N 0.000 claims 1
- ZATRGXDHCMJJSS-UHFFFAOYSA-N 3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-N-[5-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]pyridin-2-yl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC1=NC=C(C=C1)N1CCN(CC1)CCC(F)(F)F)NC1=NC=C(N=C1)C(F)(F)F ZATRGXDHCMJJSS-UHFFFAOYSA-N 0.000 claims 1
- ASKIVKRTAPXNPA-UHFFFAOYSA-N 3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-N-[6-[1-(3,3,3-trifluoropropyl)piperidin-3-yl]oxypyridin-3-yl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC=1C=NC(=CC=1)OC1CN(CCC1)CCC(F)(F)F)NC1=NC=C(N=C1)C(F)(F)F ASKIVKRTAPXNPA-UHFFFAOYSA-N 0.000 claims 1
- OFQGPRXKKQTOLM-UHFFFAOYSA-N 3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-N-[6-[1-(3,3,3-trifluoropropyl)pyrrolidin-3-yl]oxypyridin-3-yl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC=1C=NC(=CC=1)OC1CN(CC1)CCC(F)(F)F)NC1=NC=C(N=C1)C(F)(F)F OFQGPRXKKQTOLM-UHFFFAOYSA-N 0.000 claims 1
- YYIJDKGFRMPJGX-UHFFFAOYSA-N 3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-N-[6-[2-(3,3,3-trifluoropropylamino)ethoxy]pyridin-3-yl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC=1C=NC(=CC=1)OCCNCCC(F)(F)F)NC1=NC=C(N=C1)C(F)(F)F YYIJDKGFRMPJGX-UHFFFAOYSA-N 0.000 claims 1
- MITQOPJJSIAEKG-UHFFFAOYSA-N 3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-N-[6-[3-(3,3,3-trifluoropropylamino)propoxy]pyridin-3-yl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC=1C=NC(=CC=1)OCCCNCCC(F)(F)F)NC1=NC=C(N=C1)C(F)(F)F MITQOPJJSIAEKG-UHFFFAOYSA-N 0.000 claims 1
- QDFRBTZXIRODRK-UHFFFAOYSA-N 3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-N-[6-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]pyridin-3-yl]-1,2-thiazole-4-carboxamide Chemical compound CC1=NSC(=C1C(=O)NC=1C=NC(=CC=1)N1CCN(CC1)CCC(F)(F)F)NC1=NC=C(N=C1)C(F)(F)F QDFRBTZXIRODRK-UHFFFAOYSA-N 0.000 claims 1
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- BDEFFYWNWXMUOJ-UHFFFAOYSA-N N-[3-(2,2-dimethylpropanoylamino)phenyl]-3-methyl-5-(quinoxalin-2-ylamino)-1,2-thiazole-4-carboxamide Chemical compound CC(C(=O)NC=1C=C(C=CC=1)NC(=O)C=1C(=NSC=1NC1=NC2=CC=CC=C2N=C1)C)(C)C BDEFFYWNWXMUOJ-UHFFFAOYSA-N 0.000 claims 1
- AOQPVFHINKBRIX-UHFFFAOYSA-N N-[3-(3-methoxypropylcarbamoyl)phenyl]-3-methyl-5-(quinoxalin-2-ylamino)-1,2-thiazole-4-carboxamide Chemical compound COCCCNC(=O)C=1C=C(C=CC=1)NC(=O)C=1C(=NSC=1NC1=NC2=CC=CC=C2N=C1)C AOQPVFHINKBRIX-UHFFFAOYSA-N 0.000 claims 1
- CORTYTJTTYFKJK-UHFFFAOYSA-N N-[3-(cyclopropylcarbamoyl)phenyl]-3-methyl-5-(quinoxalin-2-ylamino)-1,2-thiazole-4-carboxamide Chemical compound C1(CC1)NC(=O)C=1C=C(C=CC=1)NC(=O)C=1C(=NSC=1NC1=NC2=CC=CC=C2N=C1)C CORTYTJTTYFKJK-UHFFFAOYSA-N 0.000 claims 1
- IMIIWLRKOFJQPS-CYBMUJFWSA-N N-[3-[(3R)-1-(2,2-difluoroethyl)pyrrolidin-3-yl]oxy-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1C[C@@H](CC1)OC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F IMIIWLRKOFJQPS-CYBMUJFWSA-N 0.000 claims 1
- IMIIWLRKOFJQPS-ZDUSSCGKSA-N N-[3-[(3S)-1-(2,2-difluoroethyl)pyrrolidin-3-yl]oxy-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1C[C@H](CC1)OC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F IMIIWLRKOFJQPS-ZDUSSCGKSA-N 0.000 claims 1
- XLFBYROAJYKXTO-UHFFFAOYSA-N N-[3-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCC(CC1)OC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F XLFBYROAJYKXTO-UHFFFAOYSA-N 0.000 claims 1
- FQFGHVPFLIJSHL-UHFFFAOYSA-N N-[3-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-4-fluorophenyl]-3-methyl-5-[[6-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCC(CC1)OC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC(=CN=C1)C(F)(F)F)C)F FQFGHVPFLIJSHL-UHFFFAOYSA-N 0.000 claims 1
- IMIIWLRKOFJQPS-UHFFFAOYSA-N N-[3-[1-(2,2-difluoroethyl)pyrrolidin-3-yl]oxy-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CC(CC1)OC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F IMIIWLRKOFJQPS-UHFFFAOYSA-N 0.000 claims 1
- XQQNIHKAXJGGOS-UHFFFAOYSA-N N-[3-[3-[2,2-difluoroethyl(methyl)amino]propoxy]-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN(CCCOC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)C)F XQQNIHKAXJGGOS-UHFFFAOYSA-N 0.000 claims 1
- VBXRRJSFDOEFSX-CQSZACIVSA-N N-[3-[[(3R)-1-(2,2-difluoroethyl)piperidin-3-yl]methoxy]-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1C[C@@H](CCC1)COC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F VBXRRJSFDOEFSX-CQSZACIVSA-N 0.000 claims 1
- QNWBRZYAPJQBTM-CYBMUJFWSA-N N-[3-[[(3R)-1-(2,2-difluoroethyl)pyrrolidin-3-yl]methoxy]-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1C[C@@H](CC1)COC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F QNWBRZYAPJQBTM-CYBMUJFWSA-N 0.000 claims 1
- VBXRRJSFDOEFSX-AWEZNQCLSA-N N-[3-[[(3S)-1-(2,2-difluoroethyl)piperidin-3-yl]methoxy]-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1C[C@H](CCC1)COC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F VBXRRJSFDOEFSX-AWEZNQCLSA-N 0.000 claims 1
- QNWBRZYAPJQBTM-ZDUSSCGKSA-N N-[3-[[(3S)-1-(2,2-difluoroethyl)pyrrolidin-3-yl]methoxy]-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1C[C@H](CC1)COC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F QNWBRZYAPJQBTM-ZDUSSCGKSA-N 0.000 claims 1
- JYJSNBHRMBNQCX-UHFFFAOYSA-N N-[3-[[1-(2,2-difluoroethyl)piperidin-4-yl]methoxy]-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCC(CC1)COC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F JYJSNBHRMBNQCX-UHFFFAOYSA-N 0.000 claims 1
- QNWBRZYAPJQBTM-UHFFFAOYSA-N N-[3-[[1-(2,2-difluoroethyl)pyrrolidin-3-yl]methoxy]-4-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CC(CC1)COC=1C=C(C=CC=1F)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F QNWBRZYAPJQBTM-UHFFFAOYSA-N 0.000 claims 1
- WNUCCDYYBDOGMJ-UHFFFAOYSA-N N-[3-fluoro-4-(2-hydroxyethoxy)phenyl]-3-methyl-5-[[4-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC=1C=C(C=CC=1OCCO)NC(=O)C=1C(=NSC=1NC=1SC2=C(N=1)C(=CC=C2)C(F)(F)F)C WNUCCDYYBDOGMJ-UHFFFAOYSA-N 0.000 claims 1
- DSRPIXSFMVTULS-UHFFFAOYSA-N N-[3-fluoro-4-(2-methoxyethoxy)phenyl]-3-methyl-5-[[4-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC=1C=C(C=CC=1OCCOC)NC(=O)C=1C(=NSC=1NC=1SC2=C(N=1)C(=CC=C2)C(F)(F)F)C DSRPIXSFMVTULS-UHFFFAOYSA-N 0.000 claims 1
- BUNHDQZATWFQAV-UHFFFAOYSA-N N-[4-(2,2-dimethylpropanoylamino)phenyl]-3-methyl-5-(quinoxalin-2-ylamino)-1,2-thiazole-4-carboxamide Chemical compound CC(C(=O)NC1=CC=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC2=CC=CC=C2N=C1)C)(C)C BUNHDQZATWFQAV-UHFFFAOYSA-N 0.000 claims 1
- XWMDFCSORWEBLM-UHFFFAOYSA-N N-[4-(ethylsulfamoyl)phenyl]-3-methyl-5-(quinoxalin-2-ylamino)-1,2-thiazole-4-carboxamide Chemical compound C(C)NS(=O)(=O)C1=CC=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC2=CC=CC=C2N=C1)C XWMDFCSORWEBLM-UHFFFAOYSA-N 0.000 claims 1
- CFBPTBBBEAEWDA-UHFFFAOYSA-N N-[4-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-3-fluorophenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCC(CC1)OC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F)F CFBPTBBBEAEWDA-UHFFFAOYSA-N 0.000 claims 1
- WUISCIGLDYFJCR-UHFFFAOYSA-N N-[4-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-3-fluorophenyl]-3-methyl-5-[[6-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCC(CC1)OC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC(=CN=C1)C(F)(F)F)C)F)F WUISCIGLDYFJCR-UHFFFAOYSA-N 0.000 claims 1
- VGSGEDARTGPKEC-UHFFFAOYSA-N N-[4-[4-(2,2-difluoroethyl)piperazine-1-carbonyl]phenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCN(CC1)C(=O)C1=CC=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F VGSGEDARTGPKEC-UHFFFAOYSA-N 0.000 claims 1
- AMPCCGWUMOBFJT-UHFFFAOYSA-N N-[4-[4-(2,2-difluoroethyl)piperazine-1-carbonyl]phenyl]-3-methyl-5-[[6-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCN(CC1)C(=O)C1=CC=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC(=CN=C1)C(F)(F)F)C)F AMPCCGWUMOBFJT-UHFFFAOYSA-N 0.000 claims 1
- BWYDVVUKBICYNM-CQSZACIVSA-N N-[4-fluoro-3-[(3R)-1-(3,3,3-trifluoropropyl)pyrrolidin-3-yl]oxyphenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)O[C@H]1CN(CC1)CCC(F)(F)F BWYDVVUKBICYNM-CQSZACIVSA-N 0.000 claims 1
- OAYDAYANSPNWIN-GFCCVEGCSA-N N-[4-fluoro-3-[(3R)-pyrrolidin-3-yl]oxyphenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)O[C@H]1CNCC1 OAYDAYANSPNWIN-GFCCVEGCSA-N 0.000 claims 1
- BWYDVVUKBICYNM-AWEZNQCLSA-N N-[4-fluoro-3-[(3S)-1-(3,3,3-trifluoropropyl)pyrrolidin-3-yl]oxyphenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)O[C@@H]1CN(CC1)CCC(F)(F)F BWYDVVUKBICYNM-AWEZNQCLSA-N 0.000 claims 1
- VIUCUHWGJAJJHN-UHFFFAOYSA-N N-[4-fluoro-3-[3-(2,2,2-trifluoroethylamino)propoxy]phenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)OCCCNCC(F)(F)F VIUCUHWGJAJJHN-UHFFFAOYSA-N 0.000 claims 1
- DFHMZKVPYVKBDJ-UHFFFAOYSA-N N-[4-fluoro-3-[3-[methyl(2,2,2-trifluoroethyl)amino]propoxy]phenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)OCCCN(CC(F)(F)F)C DFHMZKVPYVKBDJ-UHFFFAOYSA-N 0.000 claims 1
- YBUVMXOVCUHFLF-CQSZACIVSA-N N-[4-fluoro-3-[[(3R)-1-(2,2,2-trifluoroethyl)piperidin-3-yl]methoxy]phenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)OC[C@H]1CN(CCC1)CC(F)(F)F YBUVMXOVCUHFLF-CQSZACIVSA-N 0.000 claims 1
- YBUVMXOVCUHFLF-AWEZNQCLSA-N N-[4-fluoro-3-[[(3S)-1-(2,2,2-trifluoroethyl)piperidin-3-yl]methoxy]phenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)OC[C@@H]1CN(CCC1)CC(F)(F)F YBUVMXOVCUHFLF-AWEZNQCLSA-N 0.000 claims 1
- TVRSTVTWYZZDKM-UHFFFAOYSA-N N-[4-fluoro-3-[[1-(3,3,3-trifluoropropyl)piperidin-3-yl]methoxy]phenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)OCC1CN(CCC1)CCC(F)(F)F TVRSTVTWYZZDKM-UHFFFAOYSA-N 0.000 claims 1
- AFOMAPNEENSLEW-UHFFFAOYSA-N N-[4-fluoro-3-[[1-(3,3,3-trifluoropropyl)piperidin-4-yl]methoxy]phenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)OCC1CCN(CC1)CCC(F)(F)F AFOMAPNEENSLEW-UHFFFAOYSA-N 0.000 claims 1
- IBZGGZCKFRFIRC-UHFFFAOYSA-N N-[4-fluoro-3-[[1-(3,3,3-trifluoropropyl)pyrrolidin-3-yl]methoxy]phenyl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)OCC1CN(CC1)CCC(F)(F)F IBZGGZCKFRFIRC-UHFFFAOYSA-N 0.000 claims 1
- DWTFCXQQKGYEBH-UHFFFAOYSA-N N-[6-(1-acetylpiperidin-4-yl)oxypyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound C(C)(=O)N1CCC(CC1)OC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C DWTFCXQQKGYEBH-UHFFFAOYSA-N 0.000 claims 1
- QIQDCBPMHVGEGY-UHFFFAOYSA-N N-[6-(1-acetylpiperidin-4-yl)oxypyridin-3-yl]-3-methyl-5-[[6-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound C(C)(=O)N1CCC(CC1)OC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC(=CN=C1)C(F)(F)F)C QIQDCBPMHVGEGY-UHFFFAOYSA-N 0.000 claims 1
- OVSUMRFXMMDDSW-UHFFFAOYSA-N N-[6-(2-hydroxyethoxy)pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound OCCOC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C OVSUMRFXMMDDSW-UHFFFAOYSA-N 0.000 claims 1
- QHJLNELGYZCPGC-UHFFFAOYSA-N N-[6-(2-hydroxyethoxy)pyridin-3-yl]-3-methyl-5-[[6-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound OCCOC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC(=CN=C1)C(F)(F)F)C QHJLNELGYZCPGC-UHFFFAOYSA-N 0.000 claims 1
- QCOXRVNGGHDCFP-UHFFFAOYSA-N N-[6-(2-methoxyethoxy)pyridin-3-yl]-3-methyl-5-[[4-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound COCCOC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC=1SC2=C(N=1)C(=CC=C2)C(F)(F)F)C QCOXRVNGGHDCFP-UHFFFAOYSA-N 0.000 claims 1
- ILWPGJUOUPSJIF-UHFFFAOYSA-N N-[6-[(3,3-difluoro-1-propylpiperidin-4-yl)methoxy]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC1(CN(CCC1COC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)CCC)F ILWPGJUOUPSJIF-UHFFFAOYSA-N 0.000 claims 1
- QVYIRVNFKDPQMJ-UHFFFAOYSA-N N-[6-[1-(2-fluoroethyl)piperidin-3-yl]oxypyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FCCN1CC(CCC1)OC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C QVYIRVNFKDPQMJ-UHFFFAOYSA-N 0.000 claims 1
- WDEGZGVQFBBVEV-UHFFFAOYSA-N N-[6-[1-(2-fluoroethyl)piperidin-4-yl]oxypyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FCCN1CCC(CC1)OC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C WDEGZGVQFBBVEV-UHFFFAOYSA-N 0.000 claims 1
- DHACGFKWRCJJMD-UHFFFAOYSA-N N-[6-[1-(2-fluoroethyl)piperidin-4-yl]oxypyridin-3-yl]-3-methyl-5-[[6-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FCCN1CCC(CC1)OC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC(=CN=C1)C(F)(F)F)C DHACGFKWRCJJMD-UHFFFAOYSA-N 0.000 claims 1
- AIYOJFGSTXKVDV-UHFFFAOYSA-N N-[6-[1-(2-fluoroethyl)pyrrolidin-3-yl]oxypyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FCCN1CC(CC1)OC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C AIYOJFGSTXKVDV-UHFFFAOYSA-N 0.000 claims 1
- UQRCKLJNXAZODF-UHFFFAOYSA-N N-[6-[2-(2,2-difluoroethylamino)ethoxy]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CNCCOC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F UQRCKLJNXAZODF-UHFFFAOYSA-N 0.000 claims 1
- DBIJTBYIMZDYBR-UHFFFAOYSA-N N-[6-[2-(2-fluoroethylamino)ethoxy]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FCCNCCOC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C DBIJTBYIMZDYBR-UHFFFAOYSA-N 0.000 claims 1
- DTADBGHUKKUOJT-UHFFFAOYSA-N N-[6-[2-[1-(2,2-difluoroethyl)piperidin-4-yl]ethyl]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCC(CC1)CCC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F DTADBGHUKKUOJT-UHFFFAOYSA-N 0.000 claims 1
- OSVRJYUJULZZGG-UHFFFAOYSA-N N-[6-[3-[2-fluoroethyl(methyl)amino]propoxy]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FCCN(CCCOC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)C OSVRJYUJULZZGG-UHFFFAOYSA-N 0.000 claims 1
- PMRQAXAKVKGFAS-UHFFFAOYSA-N N-[6-[[1-(2,2-difluoroethyl)-3,3-difluoropiperidin-4-yl]methoxy]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CC(C(CC1)COC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)(F)F)F PMRQAXAKVKGFAS-UHFFFAOYSA-N 0.000 claims 1
- QVTVINGFFIJWIV-UHFFFAOYSA-N N-[6-[[1-(2,2-difluoroethyl)piperidin-3-yl]methoxy]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CC(CCC1)COC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F QVTVINGFFIJWIV-UHFFFAOYSA-N 0.000 claims 1
- WEXQWTDGYKEWIG-UHFFFAOYSA-N N-[6-[[1-(2,2-difluoroethyl)piperidin-4-yl]methoxy]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CCC(CC1)COC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F WEXQWTDGYKEWIG-UHFFFAOYSA-N 0.000 claims 1
- GVGRUGCPDFTMJO-UHFFFAOYSA-N N-[6-[[1-(2,2-difluoroethyl)pyrrolidin-3-yl]methoxy]pyridin-3-yl]-3-methyl-5-[[5-(trifluoromethyl)pyrazin-2-yl]amino]-1,2-thiazole-4-carboxamide Chemical compound FC(CN1CC(CC1)COC1=CC=C(C=N1)NC(=O)C=1C(=NSC=1NC1=NC=C(N=C1)C(F)(F)F)C)F GVGRUGCPDFTMJO-UHFFFAOYSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 1
- 239000004473 Threonine Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000000973 chemotherapeutic effect Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical group OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-M glutaminate Chemical compound [O-]C(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-M 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 claims 1
- ZMUAIBYMMQIFKG-UHFFFAOYSA-N methyl 3-[[3-[[3-methyl-5-(quinoxalin-2-ylamino)-1,2-thiazole-4-carbonyl]amino]benzoyl]amino]propanoate Chemical compound CC1=NSC(=C1C(=O)NC=1C=C(C(=O)NCCC(=O)OC)C=CC=1)NC1=NC2=CC=CC=C2N=C1 ZMUAIBYMMQIFKG-UHFFFAOYSA-N 0.000 claims 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- ORXYXGVCYKKPLX-UHFFFAOYSA-N tert-butyl 3-[[5-[[3-methyl-5-(quinoxalin-2-ylamino)-1,2-thiazole-4-carbonyl]amino]pyridin-2-yl]amino]propanoate Chemical compound CC1=NSC(=C1C(=O)NC=1C=CC(=NC=1)NCCC(=O)OC(C)(C)C)NC1=NC2=CC=CC=C2N=C1 ORXYXGVCYKKPLX-UHFFFAOYSA-N 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 CC*1CCCC1 Chemical compound CC*1CCCC1 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14153031.1 | 2014-01-29 | ||
| EP14153031 | 2014-01-29 | ||
| EP14178680.6A EP2980088A1 (en) | 2014-07-28 | 2014-07-28 | Amino-substituted isothiazoles |
| EP14178680.6 | 2014-07-28 | ||
| PCT/EP2015/051440 WO2015113920A1 (en) | 2014-01-29 | 2015-01-26 | Amino-substituted isothiazoles |
Publications (2)
| Publication Number | Publication Date |
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| JP2017512184A JP2017512184A (ja) | 2017-05-18 |
| JP2017512184A5 true JP2017512184A5 (enExample) | 2018-03-01 |
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| JP2016548682A Withdrawn JP2017512184A (ja) | 2014-01-29 | 2015-01-26 | アミノ置換されたイソチアゾール類 |
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| EP (1) | EP3099682A1 (enExample) |
| JP (1) | JP2017512184A (enExample) |
| CN (1) | CN106414435A (enExample) |
| CA (1) | CA2937989A1 (enExample) |
| WO (1) | WO2015113920A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
| TWI808055B (zh) | 2016-05-11 | 2023-07-11 | 美商滬亞生物國際有限公司 | Hdac 抑制劑與 pd-1 抑制劑之組合治療 |
| EP3529245A4 (en) | 2016-10-24 | 2020-12-23 | Yumanity Therapeutics, Inc. | COMPOUNDS AND USES OF THE LATEST |
| MA47212A (fr) | 2017-01-06 | 2019-11-13 | Yumanity Therapeutics Inc | Méthodes de traitement de troubles neurologiques |
| KR102695118B1 (ko) * | 2017-03-29 | 2024-08-16 | 이스트만 케미칼 컴파니 | 위치-선택적으로 치환된 셀룰로스 에스터 |
| WO2019084157A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | COMPOUNDS AND USES THEREOF |
| ES3043183T3 (en) | 2018-03-23 | 2025-11-25 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
| MA54829A (fr) | 2019-01-24 | 2021-12-01 | Yumanity Therapeutics Inc | Composés et leurs utilisations |
| US20230078764A1 (en) * | 2019-03-22 | 2023-03-16 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
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| BRPI0906473A8 (pt) * | 2008-01-04 | 2016-02-10 | Intellikine Inc | Certas entidades químicas, composições e métodos |
| WO2011128388A2 (en) * | 2010-04-15 | 2011-10-20 | Novartis Ag | Oxazole and thiazole compounds as ksp inhibitors |
| EP2951174B1 (en) * | 2013-01-30 | 2017-04-26 | Bayer Pharma Aktiengesellschaft | Amino-substituted isothiazoles |
-
2015
- 2015-01-26 WO PCT/EP2015/051440 patent/WO2015113920A1/en not_active Ceased
- 2015-01-26 CA CA2937989A patent/CA2937989A1/en not_active Abandoned
- 2015-01-26 CN CN201580017711.2A patent/CN106414435A/zh active Pending
- 2015-01-26 EP EP15701759.1A patent/EP3099682A1/en not_active Withdrawn
- 2015-01-26 US US15/115,274 patent/US20170334899A1/en not_active Abandoned
- 2015-01-26 JP JP2016548682A patent/JP2017512184A/ja not_active Withdrawn
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