JP4585448B2 - 第Ｘａ因子阻害剤としてのピラゾール−誘導体 - Google Patents

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Publication number

JP4585448B2

JP4585448B2 JP2005502535A JP2005502535A JP4585448B2 JP 4585448 B2 JP4585448 B2 JP 4585448B2 JP 2005502535 A JP2005502535 A JP 2005502535A JP 2005502535 A JP2005502535 A JP 2005502535A JP 4585448 B2 JP4585448 B2 JP 4585448B2

Authority

JP

Japan

Prior art keywords

thiophen

chloro

ylmethyl

isopropyl

isoxazol

Prior art date

2002-12-23

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.)

Expired - Fee Related

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• 150000003217 pyrazoles Chemical class 0.000 title description 10
• 229940123583 Factor Xa inhibitor Drugs 0.000 title description 2
• -1 pyridazone Chemical compound 0.000 claims description 542
• 150000001875 compounds Chemical class 0.000 claims description 230
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 159
• 239000000203 mixture Substances 0.000 claims description 119
• 125000000623 heterocyclic group Chemical group 0.000 claims description 107
• GGURMRUSUXSEDS-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]pyrazole-3,5-dicarboxylic acid Chemical compound N1=C(C(=O)O)C=C(C(O)=O)N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GGURMRUSUXSEDS-UHFFFAOYSA-N 0.000 claims description 95
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 93
• 125000000217 alkyl group Chemical group 0.000 claims description 89
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 88
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 64
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 63
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 61
• 239000000460 chlorine Substances 0.000 claims description 55
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 50
• 150000002367 halogens Chemical class 0.000 claims description 48
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 48
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000004122 cyclic group Chemical group 0.000 claims description 41
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 38
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 36
• ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims description 33
• 239000002253 acid Substances 0.000 claims description 31
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 29
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 29
• 125000004076 pyridyl group Chemical group 0.000 claims description 26
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 25
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 24
• 229910052731 fluorine Inorganic materials 0.000 claims description 24
• 125000001544 thienyl group Chemical group 0.000 claims description 24
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 22
• XPHYXMPQRNUKIY-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[2-(2-methoxyethoxy)ethoxymethyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound COCCOCCOCC1=CC(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 XPHYXMPQRNUKIY-UHFFFAOYSA-N 0.000 claims description 22
• MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims description 22
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 22
• ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 239000011737 fluorine Substances 0.000 claims description 20
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 150000003536 tetrazoles Chemical class 0.000 claims description 20
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 19
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 19
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 19
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 19
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 19
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 19
• FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 18
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 18
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 18
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 18
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 17
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 16
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 16
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 15
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
• 125000000335 thiazolyl group Chemical group 0.000 claims description 15
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 14
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
• WHYHFYNRCMGJPY-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-thiophen-2-ylpyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(C=2SC=CC=2)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 WHYHFYNRCMGJPY-UHFFFAOYSA-N 0.000 claims description 12
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
• 125000002785 azepinyl group Chemical group 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 229930192474 thiophene Natural products 0.000 claims description 8
• DYJQYACJLAYEQR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DYJQYACJLAYEQR-UHFFFAOYSA-N 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• YKHIOPPDUVHGCL-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(O)=O)=C1 YKHIOPPDUVHGCL-UHFFFAOYSA-N 0.000 claims description 6
• VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 5
• IKJWKUWNJONWCL-UHFFFAOYSA-N 5-(azetidine-1-carbonyl)-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CCC2)=C1 IKJWKUWNJONWCL-UHFFFAOYSA-N 0.000 claims description 5
• RPRYVADYLZGDNO-UHFFFAOYSA-N 5-(azetidine-1-carbonyl)-2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RPRYVADYLZGDNO-UHFFFAOYSA-N 0.000 claims description 5
• GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims description 5
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 5
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
• JPTAKWMQGRCRCT-UHFFFAOYSA-N ethyl 1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)NC2CCN(CC2)C(C)C)=C1 JPTAKWMQGRCRCT-UHFFFAOYSA-N 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 claims description 4
• CSWIFDWSGAPZQQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(furan-2-yl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C=2OC=CC=2)=C1 CSWIFDWSGAPZQQ-UHFFFAOYSA-N 0.000 claims description 4
• IGFMAGLCUPICTQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(furan-2-yl)-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrazole-3-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C(=CC(=N2)C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)C=2OC=CC=2)=NO1 IGFMAGLCUPICTQ-UHFFFAOYSA-N 0.000 claims description 4
• FQRGFMDCLSIWKO-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(hydroxymethyl)-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrazole-3-carboxamide Chemical compound OCC1=CC(C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 FQRGFMDCLSIWKO-UHFFFAOYSA-N 0.000 claims description 4
• IAUKLYNBOHXCPI-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)-5-propylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(C#N)C(CCC)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 IAUKLYNBOHXCPI-UHFFFAOYSA-N 0.000 claims description 4
• MWSZMNDLBBGRLJ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(C#N)C(C=2SC=CC=2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 MWSZMNDLBBGRLJ-UHFFFAOYSA-N 0.000 claims description 4
• SWBMLZSWIROPSM-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-methoxyethoxymethyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(COCCOC)C=C1C(=O)NC1CCN(C(C)C)CC1 SWBMLZSWIROPSM-UHFFFAOYSA-N 0.000 claims description 4
• WWFRSWPBUNIUJR-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-oxo-1,3-oxazolidine-3-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2C(OCC2)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 WWFRSWPBUNIUJR-UHFFFAOYSA-N 0.000 claims description 4
• LTXWLSOMNVDSON-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CC(O)C2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 LTXWLSOMNVDSON-UHFFFAOYSA-N 0.000 claims description 4
• VULRIWHYXFKIIN-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(4,4-difluoropiperidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCC(F)(F)CC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 VULRIWHYXFKIIN-UHFFFAOYSA-N 0.000 claims description 4
• RDBUONFQFSETIY-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C=2SC=CC=2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RDBUONFQFSETIY-UHFFFAOYSA-N 0.000 claims description 4
• QXOLXDBDQWEGIY-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[(1-propan-2-ylpiperidin-4-yl)methyl]-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1CNC(=O)C1=CC(C=2SC=CC=2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QXOLXDBDQWEGIY-UHFFFAOYSA-N 0.000 claims description 4
• JOCCOIPBVWXHIU-SFHVURJKSA-N (2s)-1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2[C@@H](CC2)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 JOCCOIPBVWXHIU-SFHVURJKSA-N 0.000 claims description 3
• QREXSVFXXKWBAJ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-n-methylsulfonyl-5-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3,5-dicarboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)NS(C)(=O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QREXSVFXXKWBAJ-UHFFFAOYSA-N 0.000 claims description 3
• ZDLWJPKJKIRKCL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)-5-propylpyrazole-3-carboxamide Chemical compound CCCC1=C(C#N)C(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 ZDLWJPKJKIRKCL-UHFFFAOYSA-N 0.000 claims description 3
• IATLXOOKFSXVKJ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C(=C1C=2SC=CC=2)C#N)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 IATLXOOKFSXVKJ-UHFFFAOYSA-N 0.000 claims description 3
• FUDWOSJPMAUSHR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C(=C1)C#N)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 FUDWOSJPMAUSHR-UHFFFAOYSA-N 0.000 claims description 3
• SIQUSQWVAADNSH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-thiophen-2-ylpyrazole-3-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)O)C=C1C1=CC=CS1 SIQUSQWVAADNSH-UHFFFAOYSA-N 0.000 claims description 3
• BYQPTZFMJUFDIB-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C(=N1)C(F)(F)F)=CN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 BYQPTZFMJUFDIB-UHFFFAOYSA-N 0.000 claims description 3
• IUQSVRWEHBDOPQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C=2SC=CC=2)=C1 IUQSVRWEHBDOPQ-UHFFFAOYSA-N 0.000 claims description 3
• RWCRMRXVVDJHMG-UHFFFAOYSA-N 2-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]oxyacetic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)OCC(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RWCRMRXVVDJHMG-UHFFFAOYSA-N 0.000 claims description 3
• QXJLMYMNYYQORD-UHFFFAOYSA-N 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]-methylamino]acetic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N(C)CC(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QXJLMYMNYYQORD-UHFFFAOYSA-N 0.000 claims description 3
• LNSAXVOIIHJKAG-UHFFFAOYSA-N 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]-3,3,3-trifluoropropanoic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)NC(C(O)=O)C(F)(F)F)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 LNSAXVOIIHJKAG-UHFFFAOYSA-N 0.000 claims description 3
• YBIUGSBCWFNIKH-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-4-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C=2SC=CC=2)=NN1CC1=CSC(C=2SC(Cl)=CC=2)=N1 YBIUGSBCWFNIKH-UHFFFAOYSA-N 0.000 claims description 3
• BGFQYKLJSQSFMB-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(2,4-dichlorophenyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(C=2C(=CC(Cl)=CC=2)Cl)C=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 BGFQYKLJSQSFMB-UHFFFAOYSA-N 0.000 claims description 3
• RVPWYEUJXQXLMA-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(C#N)C=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RVPWYEUJXQXLMA-UHFFFAOYSA-N 0.000 claims description 3
• QXNISAJLGKODCE-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-methylsulfonylpyrrolidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CC(CC2)S(C)(=O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QXNISAJLGKODCE-UHFFFAOYSA-N 0.000 claims description 3
• ZASUCJSHSMJOBZ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(morpholine-4-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCOCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 ZASUCJSHSMJOBZ-UHFFFAOYSA-N 0.000 claims description 3
• BALWXLJIHCTWKH-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCN(CCO)CC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 BALWXLJIHCTWKH-UHFFFAOYSA-N 0.000 claims description 3
• NCGXAVOHHUAIOV-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[4-(2-oxopyrrolidin-1-yl)piperidine-1-carbonyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCC(CC2)N2C(CCC2)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 NCGXAVOHHUAIOV-UHFFFAOYSA-N 0.000 claims description 3
• PZLBMPDRVKGEDJ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[4-(hydroxymethyl)piperidine-1-carbonyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCC(CO)CC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 PZLBMPDRVKGEDJ-UHFFFAOYSA-N 0.000 claims description 3
• QHFCHZAABCKOPQ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-methyl-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QHFCHZAABCKOPQ-UHFFFAOYSA-N 0.000 claims description 3
• RLLIVYAPBPIXDT-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-(1,3-thiazolidine-3-carbonyl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CSCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RLLIVYAPBPIXDT-UHFFFAOYSA-N 0.000 claims description 3
• DGNUPCRLEZEJHY-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-(pyrrolidine-1-carbonyl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DGNUPCRLEZEJHY-UHFFFAOYSA-N 0.000 claims description 3
• HMVSSZRUJOAIER-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-(thiomorpholine-4-carbonyl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCSCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 HMVSSZRUJOAIER-UHFFFAOYSA-N 0.000 claims description 3
• JDAJKZAZEKHTPQ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-[2-(trifluoromethyl)pyrrolidine-1-carbonyl]pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2C(CCC2)C(F)(F)F)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 JDAJKZAZEKHTPQ-UHFFFAOYSA-N 0.000 claims description 3
• DBKQWBAGGQFKIM-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-propylpyrazole-3-carboxamide Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(CCC)C=C1C(=O)NC1CCN(C(C)C)CC1 DBKQWBAGGQFKIM-UHFFFAOYSA-N 0.000 claims description 3
• DECGKHKHBIAIRZ-UHFFFAOYSA-N 2-hydroxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)OCCO)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DECGKHKHBIAIRZ-UHFFFAOYSA-N 0.000 claims description 3
• SWWNEEARDBKZJW-UHFFFAOYSA-N 3-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]propanoic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)NCCC(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 SWWNEEARDBKZJW-UHFFFAOYSA-N 0.000 claims description 3
• BGPXQDRSXPTAIS-UHFFFAOYSA-N 5-tert-butyl-2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(C)(C)C)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 BGPXQDRSXPTAIS-UHFFFAOYSA-N 0.000 claims description 3
• LTORGPPRBRMWNA-UHFFFAOYSA-N C1CC1NC(=O)C1=NN(C(=C1)C(=O)O)CC1=NOC(=C1)C=1SC(=CC1)Cl Chemical compound C1CC1NC(=O)C1=NN(C(=C1)C(=O)O)CC1=NOC(=C1)C=1SC(=CC1)Cl LTORGPPRBRMWNA-UHFFFAOYSA-N 0.000 claims description 3
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
• 239000005977 Ethylene Chemical group 0.000 claims description 3
• BIOMNDTWRIMQGV-UHFFFAOYSA-N ethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)OCC)C=C1C(=O)NC1CCN(C(C)C)CC1 BIOMNDTWRIMQGV-UHFFFAOYSA-N 0.000 claims description 3
• CCFWESCPUILQKE-UHFFFAOYSA-N ethyl 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]acetate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)NCC(=O)OCC)C=C1C(=O)NC1CCN(C(C)C)CC1 CCFWESCPUILQKE-UHFFFAOYSA-N 0.000 claims description 3
• FGJPGGDLBPGGNS-UHFFFAOYSA-N ethyl 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=CC(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 FGJPGGDLBPGGNS-UHFFFAOYSA-N 0.000 claims description 3
• CNJGKWDHDUQANJ-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)OC)C=C1C(=O)NC1CCN(C(C)C)CC1 CNJGKWDHDUQANJ-UHFFFAOYSA-N 0.000 claims description 3
• UPXNUDZXDSQQMG-UHFFFAOYSA-N propan-2-yl 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]acetate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)NCC(=O)OC(C)C)C=C1C(=O)NC1CCN(C(C)C)CC1 UPXNUDZXDSQQMG-UHFFFAOYSA-N 0.000 claims description 3
• 125000005494 pyridonyl group Chemical group 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• JOCCOIPBVWXHIU-UHFFFAOYSA-N 1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2C(CC2)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 JOCCOIPBVWXHIU-UHFFFAOYSA-N 0.000 claims description 2
• BXSLFHKFBUGMNX-UHFFFAOYSA-N 1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CC(C2)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 BXSLFHKFBUGMNX-UHFFFAOYSA-N 0.000 claims description 2
• JVDGNVQHTOTIFQ-UHFFFAOYSA-N 1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2C(CCC2)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 JVDGNVQHTOTIFQ-UHFFFAOYSA-N 0.000 claims description 2
• QOCNSCGBIFXKNQ-UHFFFAOYSA-N 1-[2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2C(CC2)C(O)=O)=C1 QOCNSCGBIFXKNQ-UHFFFAOYSA-N 0.000 claims description 2
• VKDQXRGYAINZQX-UHFFFAOYSA-N 1-[2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CC(C2)C(O)=O)=C1 VKDQXRGYAINZQX-UHFFFAOYSA-N 0.000 claims description 2
• FHRDUPTZGUNXLD-UHFFFAOYSA-N 1-[2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2C(CCC2)C(O)=O)=C1 FHRDUPTZGUNXLD-UHFFFAOYSA-N 0.000 claims description 2
• LLATVTSYXRUZGU-UHFFFAOYSA-N 1-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-4-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC=2N=C(SC=2)C=2SC(Cl)=CC=2)C(C=2SC=CC=2)=C1 LLATVTSYXRUZGU-UHFFFAOYSA-N 0.000 claims description 2
• OVVDMXKWFMNGLN-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-n,5-n-bis(1-propan-2-ylpiperidin-4-yl)pyrazole-3,5-dicarboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)NC2CCN(CC2)C(C)C)=C1 OVVDMXKWFMNGLN-UHFFFAOYSA-N 0.000 claims description 2
• CRGJLBUKLXMBCG-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(2,4-dichlorophenyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C(=C1)C=2C(=CC(Cl)=CC=2)Cl)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 CRGJLBUKLXMBCG-UHFFFAOYSA-N 0.000 claims description 2
• VKYPCYFLMMYWQE-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2,2-dimethylpyrrolidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2C(CCC2)(C)C)=C1 VKYPCYFLMMYWQE-UHFFFAOYSA-N 0.000 claims description 2
• JPQGPWDWWPQYEU-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-oxo-3h-1,3,4-oxadiazol-5-yl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C=2OC(=O)NN=2)=C1 JPQGPWDWWPQYEU-UHFFFAOYSA-N 0.000 claims description 2
• SYZNRFJJOOJACM-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CC(O)C2)=C1 SYZNRFJJOOJACM-UHFFFAOYSA-N 0.000 claims description 2
• UNUMMFIBPNTOPT-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxypyrrolidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CC(O)CC2)=C1 UNUMMFIBPNTOPT-UHFFFAOYSA-N 0.000 claims description 2
• MCFPQJDETZLHHJ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-methylsulfonylpyrrolidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CC(CC2)S(C)(=O)=O)=C1 MCFPQJDETZLHHJ-UHFFFAOYSA-N 0.000 claims description 2
• OUKSVIDVIAYXAP-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(4,4-difluoropiperidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CCC(F)(F)CC2)=C1 OUKSVIDVIAYXAP-UHFFFAOYSA-N 0.000 claims description 2
• ZNHVVTLYJIFLQX-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(4-hydroxypiperidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CCC(O)CC2)=C1 ZNHVVTLYJIFLQX-UHFFFAOYSA-N 0.000 claims description 2
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• PHTBBVXSIJPAJE-UHFFFAOYSA-N 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]ethyl dihydrogen phosphate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)NCCOP(O)(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 PHTBBVXSIJPAJE-UHFFFAOYSA-N 0.000 claims description 2
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