JP2018507235A5

JP2018507235A5 -

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Publication number: JP2018507235A5
Authority: JP; Japan
Prior art keywords: thiophen; piperidin; tert; methanone; butylpyridin
Prior art date: 2016-03-04
Legal status : Withdrawn

Application number

JP2017546186A

Other languages

English (en)

Japanese (ja)

Other versions

JP2018507235A (ja

Filing date

2016-03-04

Publication date

2019-04-18

2016-03-04 Application filed filed Critical

2016-03-04 Priority claimed from PCT/US2016/020802 external-priority patent/WO2016141258A1/en

2018-03-15 Publication of JP2018507235A publication Critical patent/JP2018507235A/ja

2019-04-18 Publication of JP2018507235A5 publication Critical patent/JP2018507235A5/ja

Status Withdrawn legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims description 79
-1 C3 -C 6 cycloalkenyl Chemical group 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 25
125000000623 heterocyclic group Chemical group 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 20
125000001072 heteroaryl group Chemical group 0.000 claims description 20
150000002431 hydrogen Chemical class 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 17
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
230000003463 hyperproliferative effect Effects 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
XISSHHYLHVBBOY-UHFFFAOYSA-N [3-chloro-4-[5-[2-(3-methylbutyl)pyrazol-3-yl]thiophen-3-yl]phenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound ClC=1C=C(C(=O)N2CCC(CC2)(F)F)C=CC=1C1=CSC(=C1)C1=CC=NN1CCC(C)C XISSHHYLHVBBOY-UHFFFAOYSA-N 0.000 claims description 4
YZZVDIFSHPOLAH-UHFFFAOYSA-N [4-[3-(2-tert-butylpyridin-4-yl)-1H-pyrazol-5-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=NNC(=C1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl YZZVDIFSHPOLAH-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
229910052796 boron Inorganic materials 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 4
206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
208000030159 metabolic disease Diseases 0.000 claims description 3
QPVRJHFMGWHFOU-UHFFFAOYSA-N (3-amino-3-methylpiperidin-1-yl)-[4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2CC(CCC2)(N)C)C=C1)Cl QPVRJHFMGWHFOU-UHFFFAOYSA-N 0.000 claims description 2
KYGXZISEKTUNCW-UHFFFAOYSA-N (3-aminopiperidin-1-yl)-[3-chloro-4-[5-(2-morpholin-4-ylpyridin-4-yl)thiophen-3-yl]phenyl]methanone Chemical compound ClC=1C=C(C(=O)N2CC(CCC2)N)C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)N1CCOCC1 KYGXZISEKTUNCW-UHFFFAOYSA-N 0.000 claims description 2
BMPUILMJNYNTEK-UHFFFAOYSA-N (3-aminopiperidin-1-yl)-[4-[2-(2-tert-butylpyridin-4-yl)-1H-imidazol-5-yl]-3-chlorophenyl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1NC=C(N=1)C1=C(C=C(C(=O)N2CC(CCC2)N)C=C1)Cl BMPUILMJNYNTEK-UHFFFAOYSA-N 0.000 claims description 2
XWTKHXBHGNYWIX-UHFFFAOYSA-N (3-aminopiperidin-1-yl)-[4-[5-(2-tert-butylpyridin-4-yl)-2-methylthiophen-3-yl]-3-chlorophenyl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=C(S1)C)C1=C(C=C(C(=O)N2CC(CCC2)N)C=C1)Cl XWTKHXBHGNYWIX-UHFFFAOYSA-N 0.000 claims description 2
HGEHGFHRFXJJFB-UHFFFAOYSA-N (3-aminopiperidin-1-yl)-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)N)C=C1)Cl HGEHGFHRFXJJFB-UHFFFAOYSA-N 0.000 claims description 2
VIVCJARLMZHHDK-GOSISDBHSA-N (3R)-1-[4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorobenzoyl]piperidine-3-carboxylic acid Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@@H](CCC2)C(=O)O)C=C1)Cl VIVCJARLMZHHDK-GOSISDBHSA-N 0.000 claims description 2
IFOGGAPDPASLKH-UHFFFAOYSA-N (4-aminopiperidin-1-yl)-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCC(CC2)N)C=C1)Cl IFOGGAPDPASLKH-UHFFFAOYSA-N 0.000 claims description 2
FROHQCQFWBMJDA-OAQYLSRUSA-N 1-[(3R)-1-[4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorobenzoyl]piperidin-3-yl]imidazolidin-2-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@@H](CCC2)N2C(NCC2)=O)C=C1)Cl FROHQCQFWBMJDA-OAQYLSRUSA-N 0.000 claims description 2
NSWHIQLQRZTNQJ-UHFFFAOYSA-N 1-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-3-yl]-3-cyclopropylurea Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)NC(=O)NC2CC2)C=C1)Cl NSWHIQLQRZTNQJ-UHFFFAOYSA-N 0.000 claims description 2
VWVMLVQEQBJMNE-UHFFFAOYSA-N 1-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-3-yl]pyrrolidin-2-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)N2C(CCC2)=O)C=C1)Cl VWVMLVQEQBJMNE-UHFFFAOYSA-N 0.000 claims description 2
LKISKZQXRJSAGX-UHFFFAOYSA-N 1-[4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorobenzoyl]piperidine-4-carboxylic acid Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2CCC(CC2)C(=O)O)C=C1)Cl LKISKZQXRJSAGX-UHFFFAOYSA-N 0.000 claims description 2
QLFQGQFNOOSFKE-UHFFFAOYSA-N 1-[4-[4-[4-[2-chloro-4-(4,4-difluoropiperidine-1-carbonyl)phenyl]thiophen-2-yl]pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound ClC1=C(C=CC(=C1)C(=O)N1CCC(CC1)(F)F)C=1C=C(SC=1)C1=CC(=NC=C1)N1CCN(CC1)C(C)=O QLFQGQFNOOSFKE-UHFFFAOYSA-N 0.000 claims description 2
XTCXYMCYHRYOHA-UHFFFAOYSA-N 1-[4-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperazin-1-yl]-2,2-dimethylpropan-1-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCN(CC2)C(C(C)(C)C)=O)C=C1)Cl XTCXYMCYHRYOHA-UHFFFAOYSA-N 0.000 claims description 2
HKHLWAYTOMIUHV-UHFFFAOYSA-N 1-[4-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperazin-1-yl]ethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCN(CC2)C(C)=O)C=C1)Cl HKHLWAYTOMIUHV-UHFFFAOYSA-N 0.000 claims description 2
BQIBDDWNVBUCGR-UHFFFAOYSA-N 3-chloro-4-[2-(1H-indol-4-yl)-1,3-thiazol-4-yl]-N,N-dimethylbenzamide Chemical compound ClC=1C=C(C(=O)N(C)C)C=CC=1C=1N=C(SC=1)C1=C2C=CNC2=CC=C1 BQIBDDWNVBUCGR-UHFFFAOYSA-N 0.000 claims description 2
MUNZVKGPNSDFFI-UHFFFAOYSA-N 4-[2-(2-propylpyridin-4-yl)-1,3-thiazol-4-yl]benzamide Chemical compound C(CC)C1=NC=CC(=C1)C=1SC=C(N=1)C1=CC=C(C(=O)N)C=C1 MUNZVKGPNSDFFI-UHFFFAOYSA-N 0.000 claims description 2
JAFVZRFYKXEOKM-UHFFFAOYSA-N 4-[4-[2-chloro-4-(piperidine-1-carbonyl)phenyl]thiophen-2-yl]-N-cyclohexylpyridine-2-carboxamide Chemical compound ClC1=C(C=CC(=C1)C(=O)N1CCCCC1)C1=CSC(=C1)C1=CC=NC(=C1)C(=O)NC1CCCCC1 JAFVZRFYKXEOKM-UHFFFAOYSA-N 0.000 claims description 2
RTLUBVHIOOLLLT-UHFFFAOYSA-N 4-[4-[2-chloro-4-(piperidine-1-carbonyl)phenyl]thiophen-2-yl]-N-cyclopropylpyridine-2-carboxamide Chemical compound ClC1=C(C=CC(=C1)C(=O)N1CCCCC1)C1=CSC(=C1)C1=CC=NC(=C1)C(=O)NC1CC1 RTLUBVHIOOLLLT-UHFFFAOYSA-N 0.000 claims description 2
OEZVBXUGVBUQAM-UHFFFAOYSA-N 4-[4-[4-(2-tert-butylpyridin-4-yl)-5-methylthiophen-2-yl]-3-chlorobenzoyl]piperazin-2-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1C)C1=C(C=C(C(=O)N2CC(NCC2)=O)C=C1)Cl OEZVBXUGVBUQAM-UHFFFAOYSA-N 0.000 claims description 2
CCDRVKUMUFQDJK-UHFFFAOYSA-N 4-[4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorobenzoyl]piperazin-2-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2CC(NCC2)=O)C=C1)Cl CCDRVKUMUFQDJK-UHFFFAOYSA-N 0.000 claims description 2
CQEXUKZOLXRJQK-UHFFFAOYSA-N 4-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]-1-ethylpiperazin-2-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(N(CC2)CC)=O)C=C1)Cl CQEXUKZOLXRJQK-UHFFFAOYSA-N 0.000 claims description 2
MDCNUJKRMMINKP-UHFFFAOYSA-N 4-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperazin-2-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(NCC2)=O)C=C1)Cl MDCNUJKRMMINKP-UHFFFAOYSA-N 0.000 claims description 2
RNXZNSZXQTWZEC-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)-2-methylthiophen-3-yl]-3-chloro-N-phenylbenzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=C(S1)C)C1=C(C=C(C(=O)NC2=CC=CC=C2)C=C1)Cl RNXZNSZXQTWZEC-UHFFFAOYSA-N 0.000 claims description 2
YCGNYFXOTHWPNX-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-(3-hydroxyphenyl)benzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)NC2=CC(=CC=C2)O)C=C1)Cl YCGNYFXOTHWPNX-UHFFFAOYSA-N 0.000 claims description 2
IANLUBZXBKRTCM-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-(4-fluorophenyl)benzamide Chemical compound CC(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(Cl)C=C(C=C1)C(=O)NC1=CC=C(F)C=C1 IANLUBZXBKRTCM-UHFFFAOYSA-N 0.000 claims description 2
LMVXQHLAGLWPGG-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)benzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)NC2CC3CCC(C2)N3C)C=C1)Cl LMVXQHLAGLWPGG-UHFFFAOYSA-N 0.000 claims description 2
SEEARPXDNIFGQM-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-cyclobutylbenzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)NC2CCC2)C=C1)Cl SEEARPXDNIFGQM-UHFFFAOYSA-N 0.000 claims description 2
HXIVLXVHRYGNPN-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-cyclopropylbenzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)NC2CC2)C=C1)Cl HXIVLXVHRYGNPN-UHFFFAOYSA-N 0.000 claims description 2
CQOMVQZPDDAODU-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-methyl-N-(1,3-oxazol-2-yl)benzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N(C=2OC=CN=2)C)C=C1)Cl CQOMVQZPDDAODU-UHFFFAOYSA-N 0.000 claims description 2
MGQDVKSUPOBPIJ-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-methyl-N-phenylbenzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N(C2=CC=CC=C2)C)C=C1)Cl MGQDVKSUPOBPIJ-UHFFFAOYSA-N 0.000 claims description 2
MKCSGCFMYXPYEG-UHFFFAOYSA-N 4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-phenylbenzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)NC2=CC=CC=C2)C=C1)Cl MKCSGCFMYXPYEG-UHFFFAOYSA-N 0.000 claims description 2
XCGUDGBJBRUYTQ-UHFFFAOYSA-N 5-[4-[2-chloro-4-(piperidine-1-carbonyl)phenyl]thiophen-2-yl]-1-(2-methylpropyl)pyridin-2-one Chemical compound ClC1=C(C=CC(=C1)C(=O)N1CCCCC1)C=1C=C(SC=1)C=1C=CC(N(C=1)CC(C)C)=O XCGUDGBJBRUYTQ-UHFFFAOYSA-N 0.000 claims description 2
PEYFTNBSSDSCJY-UHFFFAOYSA-N 6-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-2-methyl-3,4-dihydroisoquinolin-1-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C=1C=C2CCN(C(C2=CC=1)=O)C PEYFTNBSSDSCJY-UHFFFAOYSA-N 0.000 claims description 2
JWCUPBHCFPBTLB-UHFFFAOYSA-N 6-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-2-propan-2-yl-3,4-dihydroisoquinolin-1-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C=1C=C2CCN(C(C2=CC=1)=O)C(C)C JWCUPBHCFPBTLB-UHFFFAOYSA-N 0.000 claims description 2
SHSYPBDCYLISHG-UHFFFAOYSA-N 6-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-7-chloro-2-propan-2-yl-3,4-dihydroisoquinolin-1-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C=1C=C2CCN(C(C2=CC=1Cl)=O)C(C)C SHSYPBDCYLISHG-UHFFFAOYSA-N 0.000 claims description 2
ZELOSMOSDBIQNO-UHFFFAOYSA-N 9-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]-2,9-diazaspiro[4.5]decan-1-one Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC3(CCNC3=O)CCC2)C=C1)Cl ZELOSMOSDBIQNO-UHFFFAOYSA-N 0.000 claims description 2
206010006187 Breast cancer Diseases 0.000 claims description 2
208000026310 Breast neoplasm Diseases 0.000 claims description 2
HGEHGFHRFXJJFB-LJQANCHMSA-N C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](CCC2)N)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](CCC2)N)C=C1)Cl HGEHGFHRFXJJFB-LJQANCHMSA-N 0.000 claims description 2
LOBBIKZXQWZRAG-LJQANCHMSA-N C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](CCC2)O)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](CCC2)O)C=C1)Cl LOBBIKZXQWZRAG-LJQANCHMSA-N 0.000 claims description 2
KCCIVMIZZNSPDT-CALCHBBNSA-N C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](O[C@@H](C2)C)C)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](O[C@@H](C2)C)C)C=C1)Cl KCCIVMIZZNSPDT-CALCHBBNSA-N 0.000 claims description 2
HGEHGFHRFXJJFB-IBGZPJMESA-N C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@H](CCC2)N)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@H](CCC2)N)C=C1)Cl HGEHGFHRFXJJFB-IBGZPJMESA-N 0.000 claims description 2
LOBBIKZXQWZRAG-IBGZPJMESA-N C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@H](CCC2)O)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@H](CCC2)O)C=C1)Cl LOBBIKZXQWZRAG-IBGZPJMESA-N 0.000 claims description 2
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BMLVKPPCOWFNGN-UHFFFAOYSA-N [4-[3-(2-tert-butylpyridin-4-yl)-1,2-oxazol-5-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=NOC(=C1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl BMLVKPPCOWFNGN-UHFFFAOYSA-N 0.000 claims description 2
GGBMAFWUPWWDSL-UHFFFAOYSA-N [4-[3-(2-tert-butylpyridin-4-yl)-1,2-thiazol-5-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=NSC(=C1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl GGBMAFWUPWWDSL-UHFFFAOYSA-N 0.000 claims description 2
MCACFSPMTKZYGH-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)-1,3-oxazol-2-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1N=C(OC=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl MCACFSPMTKZYGH-UHFFFAOYSA-N 0.000 claims description 2
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KAOVSWIIUBMBCM-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)-1H-pyrrol-2-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(NC=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl KAOVSWIIUBMBCM-UHFFFAOYSA-N 0.000 claims description 2
XUSFHLVWRLGBLA-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)furan-2-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(OC=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl XUSFHLVWRLGBLA-UHFFFAOYSA-N 0.000 claims description 2
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VDHCUJXKARYCBA-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-(3,4-dihydro-2H-1,8-naphthyridin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2CCCC3=CC=CN=C23)C=C1)Cl VDHCUJXKARYCBA-UHFFFAOYSA-N 0.000 claims description 2
PKQDANKQSISDBK-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-(3-hydroxypiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2CC(CCC2)O)C=C1)Cl PKQDANKQSISDBK-UHFFFAOYSA-N 0.000 claims description 2
WGKYJEQUJIUJQS-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-(3-methoxypiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CSC(=C1)C1=C(C=C(C=C1)C(=O)N1CC(CCC1)OC)Cl WGKYJEQUJIUJQS-UHFFFAOYSA-N 0.000 claims description 2
PZJCJORCVZIXLB-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CSC(=C1)C1=C(C=C(C=C1)C(=O)N1CCC(CC1)(F)F)Cl PZJCJORCVZIXLB-UHFFFAOYSA-N 0.000 claims description 2
GYCAFTQXLRMPAG-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-(4-hydroxy-4-methylpiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2CCC(CC2)(O)C)C=C1)Cl GYCAFTQXLRMPAG-UHFFFAOYSA-N 0.000 claims description 2
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KGJULKCVGIHARZ-SANMLTNESA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-[(3S)-3-hydroxy-3-methylpiperidin-1-yl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@](CCC2)(O)C)C=C1)Cl KGJULKCVGIHARZ-SANMLTNESA-N 0.000 claims description 2
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VJSJPAIGMSZNDB-UHFFFAOYSA-N [4-[5-(1H-benzimidazol-4-yl)thiophen-3-yl]-3-chlorophenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound N1C=NC2=C1C=CC=C2C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCC(CC1)(F)F)Cl VJSJPAIGMSZNDB-UHFFFAOYSA-N 0.000 claims description 2
KNVWOGKHHKJUQU-UHFFFAOYSA-N [4-[5-(2,6-dipropylpyridin-3-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C(CC)C1=NC(=CC=C1C1=CC(=CS1)C1=CC=C(C=C1)C(=O)N1CCCCC1)CCC KNVWOGKHHKJUQU-UHFFFAOYSA-N 0.000 claims description 2
VBJDTDJADGSKIC-UHFFFAOYSA-N [4-[5-(2-aminopyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound NC1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl VBJDTDJADGSKIC-UHFFFAOYSA-N 0.000 claims description 2
NAZSUAGUQYTDLB-UHFFFAOYSA-N [4-[5-(2-aminopyrimidin-4-yl)thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound NC1=NC=CC(=N1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl NAZSUAGUQYTDLB-UHFFFAOYSA-N 0.000 claims description 2
PLPCRRZHYDTCMI-UHFFFAOYSA-N [4-[5-(2-benzylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C1=CC=CC=C1)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl PLPCRRZHYDTCMI-UHFFFAOYSA-N 0.000 claims description 2
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KREANWSPXFSVLN-UHFFFAOYSA-N [4-[5-(2-pentylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C(CCCC)C1=NC=CC(=C1)C1=CC(=CS1)C1=CC=C(C=C1)C(=O)N1CCCCC1 KREANWSPXFSVLN-UHFFFAOYSA-N 0.000 claims description 2
DBPIZNKBTIOVMM-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)-1,2-oxazol-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=NO1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl DBPIZNKBTIOVMM-UHFFFAOYSA-N 0.000 claims description 2
FYXSWJNPJKHSRD-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)-1,2-thiazol-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=NS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl FYXSWJNPJKHSRD-UHFFFAOYSA-N 0.000 claims description 2
DTURURFINJVKDU-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)-1H-imidazol-2-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1N=C(NC=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl DTURURFINJVKDU-UHFFFAOYSA-N 0.000 claims description 2
DFRQZSALLRBICM-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)-1H-pyrrol-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CN1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl DFRQZSALLRBICM-UHFFFAOYSA-N 0.000 claims description 2
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ITRKYZHKUGBBAI-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)-2-methylthiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1SC(=C(C=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl)C ITRKYZHKUGBBAI-UHFFFAOYSA-N 0.000 claims description 2
XWMYSRUQYYGLFY-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-2-hydroxyphenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=CC(=C(C=C1)C(=O)N1CCCCC1)O XWMYSRUQYYGLFY-UHFFFAOYSA-N 0.000 claims description 2
FCZDRLXZYRJZTP-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-2-methoxyphenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=CC(=C(C=C1)C(=O)N1CCCCC1)OC FCZDRLXZYRJZTP-UHFFFAOYSA-N 0.000 claims description 2
WHKSNNAHOSECCN-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC3(COC3)C2)C=C1)Cl WHKSNNAHOSECCN-UHFFFAOYSA-N 0.000 claims description 2
OZFIRYFMXBLEKH-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-(3,3-difluoropyrrolidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1SC=C(C=1)C1=C(C=C(C=C1)C(=O)N1CC(CC1)(F)F)Cl OZFIRYFMXBLEKH-UHFFFAOYSA-N 0.000 claims description 2
LOBBIKZXQWZRAG-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-(3-hydroxypiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)O)C=C1)Cl LOBBIKZXQWZRAG-UHFFFAOYSA-N 0.000 claims description 2
KZXCHPIQELATGZ-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1SC=C(C=1)C1=C(C=C(C=C1)C(=O)N1CCC(CC1)(F)F)Cl KZXCHPIQELATGZ-UHFFFAOYSA-N 0.000 claims description 2
WKTMCAMGQAHCOF-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCC(CC2)O)C=C1)Cl WKTMCAMGQAHCOF-UHFFFAOYSA-N 0.000 claims description 2
WNFWIJAESPMKLG-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCN(CC2)C)C=C1)Cl WNFWIJAESPMKLG-UHFFFAOYSA-N 0.000 claims description 2
QHPSEHDMQANFFM-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-(4-methylsulfonylpiperazin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCN(CC2)S(=O)(=O)C)C=C1)Cl QHPSEHDMQANFFM-UHFFFAOYSA-N 0.000 claims description 2
CTKGEKAFOZOTOH-GOSISDBHSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-[(3R)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](CC2)O)C=C1)Cl CTKGEKAFOZOTOH-GOSISDBHSA-N 0.000 claims description 2
DVUAZLXRFRISKF-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-[3-(1,1-dioxo-1,2-thiazolidin-2-yl)piperidin-1-yl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CC(CCC1)N1S(CCC1)(=O)=O)Cl DVUAZLXRFRISKF-UHFFFAOYSA-N 0.000 claims description 2
FKDBBMVXVWHAIA-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-[3-(methylamino)piperidin-1-yl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)NC)C=C1)Cl FKDBBMVXVWHAIA-UHFFFAOYSA-N 0.000 claims description 2
SQWALTOEPNSBFW-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-[3-[(3-chlorophenyl)methylamino]piperidin-1-yl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)NCC2=CC(=CC=C2)Cl)C=C1)Cl SQWALTOEPNSBFW-UHFFFAOYSA-N 0.000 claims description 2
ADQHIRDUTHLTNP-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-[3-[(4-chlorophenyl)methylamino]piperidin-1-yl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)NCC2=CC=C(C=C2)Cl)C=C1)Cl ADQHIRDUTHLTNP-UHFFFAOYSA-N 0.000 claims description 2
OFGFVCOVIGQYMG-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-morpholin-4-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCOCC2)C=C1)Cl OFGFVCOVIGQYMG-UHFFFAOYSA-N 0.000 claims description 2
RXGGTVXZJYIAON-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-piperazin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCNCC2)C=C1)Cl RXGGTVXZJYIAON-UHFFFAOYSA-N 0.000 claims description 2
BEJCAWZXGZEFMD-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1SC=C(C=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl BEJCAWZXGZEFMD-UHFFFAOYSA-N 0.000 claims description 2
LYGZBZWMSIMHHF-UHFFFAOYSA-N [4-[5-[2-(2,2-dimethylpropyl)pyridin-4-yl]thiophen-3-yl]-2-methoxyphenyl]-piperidin-1-ylmethanone Chemical compound COC1=C(C=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)(C)C)C(=O)N1CCCCC1 LYGZBZWMSIMHHF-UHFFFAOYSA-N 0.000 claims description 2
CPNZUKMVAQSFND-UHFFFAOYSA-N [4-[5-[2-(2-methylpropyl)pyrazol-3-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C(C(C)C)N1N=CC=C1C1=CC(=CS1)C1=CC=C(C=C1)C(=O)N1CCCCC1 CPNZUKMVAQSFND-UHFFFAOYSA-N 0.000 claims description 2
GQHMIXWUXKFFKY-UHFFFAOYSA-N [4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]-2-(trifluoromethyl)phenyl]-piperidin-1-ylmethanone Chemical compound C(C(C)C)C1=NC=CC(=C1)C1=CC(=CS1)C1=CC(=C(C=C1)C(=O)N1CCCCC1)C(F)(F)F GQHMIXWUXKFFKY-UHFFFAOYSA-N 0.000 claims description 2
RVELDNIXVUZFRJ-UHFFFAOYSA-N [4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]-2-propan-2-ylphenyl]-piperidin-1-ylmethanone Chemical compound C(C(C)C)C1=NC=CC(=C1)C1=CC(=CS1)C1=CC(=C(C=C1)C(=O)N1CCCCC1)C(C)C RVELDNIXVUZFRJ-UHFFFAOYSA-N 0.000 claims description 2
ZFVRRHMNNMDTSU-UHFFFAOYSA-N [4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]-3-(trifluoromethyl)phenyl]-piperidin-1-ylmethanone Chemical compound C(C(C)C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)C(F)(F)F ZFVRRHMNNMDTSU-UHFFFAOYSA-N 0.000 claims description 2
FGHUENJOAHPMGF-UHFFFAOYSA-N [4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C(C(C)C)C1=NC=CC(=C1)C1=CC(=CS1)C1=CC=C(C=C1)C(=O)N1CCCCC1 FGHUENJOAHPMGF-UHFFFAOYSA-N 0.000 claims description 2
ZZFURUWPUYVERC-UHFFFAOYSA-N [4-[5-[2-(cyclohexylmethyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C1(CCCCC1)CC1=NC=CC(=C1)C1=CC(=CS1)C1=CC=C(C=C1)C(=O)N1CCCCC1 ZZFURUWPUYVERC-UHFFFAOYSA-N 0.000 claims description 2
TXKINZXRLJGLGH-UHFFFAOYSA-N [4-[5-[2-[butyl(propyl)amino]pyrimidin-4-yl]thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(CCC)N(C1=NC=CC(=N1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl)CCC TXKINZXRLJGLGH-UHFFFAOYSA-N 0.000 claims description 2
KEYNXXKNJVQJKH-UHFFFAOYSA-N [4-[5-[6-(butylamino)-2-(2-methylpropyl)pyrimidin-4-yl]thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(CCC)NC1=CC(=NC(=N1)CC(C)C)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl KEYNXXKNJVQJKH-UHFFFAOYSA-N 0.000 claims description 2
NKJNIXXRANDLBL-UHFFFAOYSA-N [4-[5-[6-amino-2-(2-methylpropyl)pyrimidin-4-yl]thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound NC1=CC(=NC(=N1)CC(C)C)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl NKJNIXXRANDLBL-UHFFFAOYSA-N 0.000 claims description 2
BWZLLEOKTGWOFK-UHFFFAOYSA-N azetidin-1-yl-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]methanone Chemical compound N1(CCC1)C(=O)C1=CC(=C(C=C1)C=1C=C(SC=1)C1=CC(=NC=C1)C(C)(C)C)Cl BWZLLEOKTGWOFK-UHFFFAOYSA-N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
GCDPDATVIXJWFA-UHFFFAOYSA-N ethyl 4-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperazine-1-carboxylate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCN(CC2)C(=O)OCC)C=C1)Cl GCDPDATVIXJWFA-UHFFFAOYSA-N 0.000 claims description 2
VGZZWTBEPUMNCA-UHFFFAOYSA-N ethyl N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)NC(OCC)=O)C=C1)Cl VGZZWTBEPUMNCA-UHFFFAOYSA-N 0.000 claims description 2
FPWNRQSVMHPRKD-UHFFFAOYSA-N ethyl N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-4-yl]carbamate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCC(CC2)NC(OCC)=O)C=C1)Cl FPWNRQSVMHPRKD-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
IUDDVCYFLAOKRT-UHFFFAOYSA-N piperidin-1-yl-[3-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]methanone Chemical compound N1(CCCCC1)C(=O)C1=CC(=CC=C1)C1=CSC(=C1)C1=CC(=NC=C1)CCC IUDDVCYFLAOKRT-UHFFFAOYSA-N 0.000 claims description 2
QYQQRSZADXCBRI-UHFFFAOYSA-N piperidin-1-yl-[4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]-3-(trifluoromethyl)phenyl]methanone Chemical compound N1(CCCCC1)C(=O)C1=CC(=C(C=C1)C1=CSC(=C1)C1=CC(=NC=C1)CCC)C(F)(F)F QYQQRSZADXCBRI-UHFFFAOYSA-N 0.000 claims description 2
LHWWGSOUWHSFRE-UHFFFAOYSA-N piperidin-1-yl-[4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]methanone Chemical compound N1(CCCCC1)C(=O)C1=CC=C(C=C1)C1=CSC(=C1)C1=CC(=NC=C1)CCC LHWWGSOUWHSFRE-UHFFFAOYSA-N 0.000 claims description 2
IJPSWWFLRLNSDD-UHFFFAOYSA-N piperidin-1-yl-[4-[5-(4-propylpyridin-2-yl)thiophen-3-yl]phenyl]methanone Chemical compound N1(CCCCC1)C(=O)C1=CC=C(C=C1)C1=CSC(=C1)C1=NC=CC(=C1)CCC IJPSWWFLRLNSDD-UHFFFAOYSA-N 0.000 claims description 2
ZGSDVELAMWIIEC-UHFFFAOYSA-N piperidin-1-yl-[4-[5-(6-propylpyridin-3-yl)thiophen-3-yl]phenyl]methanone Chemical compound N1(CCCCC1)C(=O)C1=CC=C(C=C1)C1=CSC(=C1)C=1C=NC(=CC=1)CCC ZGSDVELAMWIIEC-UHFFFAOYSA-N 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
LCAUCDOAABQHEN-UHFFFAOYSA-N tert-butyl 4-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperazine-1-carboxylate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)C=C1)Cl LCAUCDOAABQHEN-UHFFFAOYSA-N 0.000 claims description 2
WOGSJTOOMNAJBM-JOCHJYFZSA-N tert-butyl N-[(3R)-1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](CCC2)NC(OC(C)(C)C)=O)C=C1)Cl WOGSJTOOMNAJBM-JOCHJYFZSA-N 0.000 claims description 2
IDLNEDUKQACMMD-OAQYLSRUSA-N tert-butyl N-[(3R)-1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]pyrrolidin-3-yl]carbamate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2C[C@@H](CC2)NC(OC(C)(C)C)=O)C=C1)Cl IDLNEDUKQACMMD-OAQYLSRUSA-N 0.000 claims description 2
MGVMKWFHPHGCQS-UHFFFAOYSA-N tert-butyl N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-3-yl]-N-methylcarbamate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)N(C(OC(C)(C)C)=O)C)C=C1)Cl MGVMKWFHPHGCQS-UHFFFAOYSA-N 0.000 claims description 2
WOGSJTOOMNAJBM-UHFFFAOYSA-N tert-butyl N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)NC(OC(C)(C)C)=O)C=C1)Cl WOGSJTOOMNAJBM-UHFFFAOYSA-N 0.000 claims description 2
OMKLQXKODZYUOX-UHFFFAOYSA-N tert-butyl N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-4-yl]carbamate Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCC(CC2)NC(OC(C)(C)C)=O)C=C1)Cl OMKLQXKODZYUOX-UHFFFAOYSA-N 0.000 claims description 2
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 claims 1
YNUJCFMEZOLBGH-UHFFFAOYSA-N 5-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]-2-(piperidine-1-carbonyl)benzonitrile Chemical compound C(C(C)C)C1=NC=CC(=C1)C1=CC(=CS1)C=1C=CC(=C(C#N)C=1)C(=O)N1CCCCC1 YNUJCFMEZOLBGH-UHFFFAOYSA-N 0.000 claims 1
CDMNCCIWZADKKY-UHFFFAOYSA-N [3-chloro-4-[5-(1-ethylindol-4-yl)thiophen-3-yl]phenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C2C=CN(C2=CC=C1)CC)C(=O)N1CCC(CC1)(F)F CDMNCCIWZADKKY-UHFFFAOYSA-N 0.000 claims 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
235000019260 propionic acid Nutrition 0.000 claims 1
238000000034 method Methods 0.000 description 5
VNHLAVQFKNFAEI-UHFFFAOYSA-N CC(C)(C)c1cc(I)ccn1 Chemical compound CC(C)(C)c1cc(I)ccn1 VNHLAVQFKNFAEI-UHFFFAOYSA-N 0.000 description 2
0 CC(C)(C)c1nccc(*)c1 Chemical compound CC(C)(C)c1nccc(*)c1 0.000 description 2
VSZASWWNELJMNR-UHFFFAOYSA-N CCc1ccnc(CC(C)C)c1 Chemical compound CCc1ccnc(CC(C)C)c1 VSZASWWNELJMNR-UHFFFAOYSA-N 0.000 description 2
XUOPMHRKFGNVLG-UHFFFAOYSA-N CCc1ccnc(N2CCCCC2)c1 Chemical compound CCc1ccnc(N2CCCCC2)c1 XUOPMHRKFGNVLG-UHFFFAOYSA-N 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
FXYTULXRJSWPDF-UHFFFAOYSA-N 4,4-difluoropiperidine-1-carbaldehyde Chemical compound FC1(F)CCN(C=O)CC1 FXYTULXRJSWPDF-UHFFFAOYSA-N 0.000 description 1
KHPUBMWFKROXON-UHFFFAOYSA-N [2-bromo-4-[1-methyl-2-(2-propylpyridin-4-yl)imidazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1)C=1N=C(N(C=1)C)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 KHPUBMWFKROXON-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1

JP2017546186A 2015-03-04 2016-03-04 ステロール調節エレメント結合タンパク質（ｓｒｅｂｐ）阻害剤 Withdrawn JP2018507235A (ja)