JP2018507235A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018507235A5 JP2018507235A5 JP2017546186A JP2017546186A JP2018507235A5 JP 2018507235 A5 JP2018507235 A5 JP 2018507235A5 JP 2017546186 A JP2017546186 A JP 2017546186A JP 2017546186 A JP2017546186 A JP 2017546186A JP 2018507235 A5 JP2018507235 A5 JP 2018507235A5
- Authority
- JP
- Japan
- Prior art keywords
- thiophen
- piperidin
- tert
- methanone
- butylpyridin
- 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.)
- Withdrawn
Links
- 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
- CCGDJAMIPLKEJI-UHFFFAOYSA-N C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C=N1)C(=O)NC1=CC=CC=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C=N1)C(=O)NC1=CC=CC=C1)Cl CCGDJAMIPLKEJI-UHFFFAOYSA-N 0.000 claims description 2
- ZUVPHPKVLVMMFC-GOSISDBHSA-N C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@@H](CC2)O)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@@H](CC2)O)C=C1)Cl ZUVPHPKVLVMMFC-GOSISDBHSA-N 0.000 claims description 2
- QPVRJHFMGWHFOU-AREMUKBSSA-N C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@@](CCC2)(N)C)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@@](CCC2)(N)C)C=C1)Cl QPVRJHFMGWHFOU-AREMUKBSSA-N 0.000 claims description 2
- KGJULKCVGIHARZ-AREMUKBSSA-N 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 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-AREMUKBSSA-N 0.000 claims description 2
- DRHBIEQIUOZZHC-SFHVURJKSA-N C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@H](CC2)N)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@H](CC2)N)C=C1)Cl DRHBIEQIUOZZHC-SFHVURJKSA-N 0.000 claims description 2
- ZUVPHPKVLVMMFC-SFHVURJKSA-N C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@H](CC2)O)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@H](CC2)O)C=C1)Cl ZUVPHPKVLVMMFC-SFHVURJKSA-N 0.000 claims description 2
- BCOGHWDTPCYMMF-IBGZPJMESA-N C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@H](CCC2)N)C=C1)Cl 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)N)C=C1)Cl BCOGHWDTPCYMMF-IBGZPJMESA-N 0.000 claims description 2
- PKQDANKQSISDBK-IBGZPJMESA-N C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@H](CCC2)O)C=C1)Cl 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)O)C=C1)Cl PKQDANKQSISDBK-IBGZPJMESA-N 0.000 claims description 2
- QPVRJHFMGWHFOU-SANMLTNESA-N C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@](CCC2)(N)C)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C(=O)N2C[C@](CCC2)(N)C)C=C1)Cl QPVRJHFMGWHFOU-SANMLTNESA-N 0.000 claims description 2
- LRNNLESWMKWRAZ-LJQANCHMSA-N C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1C)C1=C(C=C(C(=O)N2C[C@@H](CCC2)N)C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1C)C1=C(C=C(C(=O)N2C[C@@H](CCC2)N)C=C1)Cl LRNNLESWMKWRAZ-LJQANCHMSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- XBXCSPAADYNZEB-UHFFFAOYSA-N N,N-dimethyl-4-[2-(2-propylpyridin-4-yl)-1,3-thiazol-4-yl]benzamide Chemical compound CN(C(C1=CC=C(C=C1)C=1N=C(SC=1)C1=CC(=NC=C1)CCC)=O)C XBXCSPAADYNZEB-UHFFFAOYSA-N 0.000 claims description 2
- JUYMDQUBGMPOCQ-UHFFFAOYSA-N N-(2-acetamidoethyl)-4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chloro-N-ethylbenzamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N(CC)CCNC(C)=O)Cl JUYMDQUBGMPOCQ-UHFFFAOYSA-N 0.000 claims description 2
- GHBKKBSDEKLOQG-UHFFFAOYSA-N N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-3-yl]acetamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)NC(C)=O)C=C1)Cl GHBKKBSDEKLOQG-UHFFFAOYSA-N 0.000 claims description 2
- XLWROGWMUVOVHV-UHFFFAOYSA-N N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-3-yl]methanesulfonamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CC(CCC2)NS(=O)(=O)C)C=C1)Cl XLWROGWMUVOVHV-UHFFFAOYSA-N 0.000 claims description 2
- AWHHZFFJNCXKKV-UHFFFAOYSA-N N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-4-yl]-2,2-dimethylpropanamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCC(CC2)NC(C(C)(C)C)=O)C=C1)Cl AWHHZFFJNCXKKV-UHFFFAOYSA-N 0.000 claims description 2
- XWWWZHADUIUXES-UHFFFAOYSA-N N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-4-yl]acetamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCC(CC2)NC(C)=O)C=C1)Cl XWWWZHADUIUXES-UHFFFAOYSA-N 0.000 claims description 2
- IUUHJTLZIAHXHB-UHFFFAOYSA-N N-[1-[4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzoyl]piperidin-4-yl]methanesulfonamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C(=O)N2CCC(CC2)NS(=O)(=O)C)C=C1)Cl IUUHJTLZIAHXHB-UHFFFAOYSA-N 0.000 claims description 2
- XYRCTJHREZQFJX-UHFFFAOYSA-N N-[4-[4-[2-chloro-4-(piperidine-1-carbonyl)phenyl]-1-methylimidazol-2-yl]pyridin-2-yl]methanesulfonamide Chemical compound ClC1=C(C=CC(=C1)C(=O)N1CCCCC1)C=1N=C(N(C=1)C)C1=CC(=NC=C1)NS(=O)(=O)C XYRCTJHREZQFJX-UHFFFAOYSA-N 0.000 claims description 2
- YIKBNHVZDJPJMZ-UHFFFAOYSA-N N-[4-[4-[2-chloro-4-(piperidine-1-carbonyl)phenyl]thiophen-2-yl]pyridin-2-yl]-1,1,1-trifluoromethanesulfonamide Chemical compound ClC1=C(C=CC(=C1)C(=O)N1CCCCC1)C=1C=C(SC=1)C1=CC(=NC=C1)NS(=O)(=O)C(F)(F)F YIKBNHVZDJPJMZ-UHFFFAOYSA-N 0.000 claims description 2
- RGDWHRDFIVQGIU-UHFFFAOYSA-N N-[4-[4-[2-chloro-4-(piperidine-1-carbonyl)phenyl]thiophen-2-yl]pyridin-2-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=NC=CC(=C1)C=1SC=C(C=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl RGDWHRDFIVQGIU-UHFFFAOYSA-N 0.000 claims description 2
- XOPXZKUAENMAMH-UHFFFAOYSA-N N-methyl-4-[2-(2-propylpyridin-4-yl)-1,3-thiazol-4-yl]benzamide Chemical compound CNC(C1=CC=C(C=C1)C=1N=C(SC=1)C1=CC(=NC=C1)CCC)=O XOPXZKUAENMAMH-UHFFFAOYSA-N 0.000 claims description 2
- XJXAALVLRFFZFD-UHFFFAOYSA-N N-tert-butyl-4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorobenzamide Chemical compound C(C)(C)(C)NC(C1=CC(=C(C=C1)C1=CSC(=C1)C1=CC(=NC=C1)C(C)(C)C)Cl)=O XJXAALVLRFFZFD-UHFFFAOYSA-N 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- BCOGHWDTPCYMMF-LJQANCHMSA-N [(3R)-3-aminopiperidin-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)N2C[C@@H](CCC2)N)C=C1)Cl BCOGHWDTPCYMMF-LJQANCHMSA-N 0.000 claims description 2
- DRHBIEQIUOZZHC-GOSISDBHSA-N [(3R)-3-aminopyrrolidin-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)N2C[C@@H](CC2)N)C=C1)Cl DRHBIEQIUOZZHC-GOSISDBHSA-N 0.000 claims description 2
- LRNNLESWMKWRAZ-IBGZPJMESA-N [(3S)-3-aminopiperidin-1-yl]-[4-[4-(2-tert-butylpyridin-4-yl)-5-methylthiophen-2-yl]-3-chlorophenyl]methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1C)C1=C(C=C(C(=O)N2C[C@H](CCC2)N)C=C1)Cl LRNNLESWMKWRAZ-IBGZPJMESA-N 0.000 claims description 2
- SKFURDKFSURIRR-UHFFFAOYSA-N [2,3-dichloro-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC1=C(C=CC(=C1Cl)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 SKFURDKFSURIRR-UHFFFAOYSA-N 0.000 claims description 2
- VIRANIRSOSPMCZ-UHFFFAOYSA-N [2-bromo-3-chloro-4-[2-[2-(2-methylpropyl)pyridin-4-yl]-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1Cl)C=1N=C(NC=1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 VIRANIRSOSPMCZ-UHFFFAOYSA-N 0.000 claims description 2
- KHDDKHUUOGEMBE-UHFFFAOYSA-N [2-bromo-3-chloro-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1Cl)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 KHDDKHUUOGEMBE-UHFFFAOYSA-N 0.000 claims description 2
- KGUDVLMFFQAHSO-UHFFFAOYSA-N [2-bromo-3-ethynyl-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1C#C)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 KGUDVLMFFQAHSO-UHFFFAOYSA-N 0.000 claims description 2
- AGQHROVAFMAGEA-UHFFFAOYSA-N [2-bromo-4-[1-methyl-2-[2-(2-methylpropyl)pyridin-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)CC(C)C)C(=O)N1CCCCC1 AGQHROVAFMAGEA-UHFFFAOYSA-N 0.000 claims description 2
- AWLKYEGKQRPSKS-UHFFFAOYSA-N [2-bromo-4-[2-(2-piperidin-1-ylpyridin-4-yl)-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1)C=1N=C(NC=1)C1=CC(=NC=C1)N1CCCCC1)C(=O)N1CCCCC1 AWLKYEGKQRPSKS-UHFFFAOYSA-N 0.000 claims description 2
- MWAKMHFBVPIGNM-UHFFFAOYSA-N [2-bromo-4-[2-(2-propylpyridin-4-yl)-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1)C=1N=C(NC=1)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 MWAKMHFBVPIGNM-UHFFFAOYSA-N 0.000 claims description 2
- UHHZPMKWWMJSBU-UHFFFAOYSA-N [2-bromo-4-[2-(2-tert-butylpyridin-4-yl)-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1)C=1N=C(NC=1)C1=CC(=NC=C1)C(C)(C)C)C(=O)N1CCCCC1 UHHZPMKWWMJSBU-UHFFFAOYSA-N 0.000 claims description 2
- HWWSSFWHFYZZBB-UHFFFAOYSA-N [2-bromo-4-[2-[2-(2-methylpropyl)pyridin-4-yl]-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1)C=1N=C(NC=1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 HWWSSFWHFYZZBB-UHFFFAOYSA-N 0.000 claims description 2
- FZTUPBAIBCOGKS-UHFFFAOYSA-N [2-bromo-4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 FZTUPBAIBCOGKS-UHFFFAOYSA-N 0.000 claims description 2
- MHLNWFRSHKFDKO-UHFFFAOYSA-N [2-bromo-4-[5-(2-tert-butylpyridin-4-yl)-1H-pyrrol-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1Cl)C1=CNC(=C1)C1=CC(=NC=C1)C(C)(C)C)C(=O)N1CCCCC1 MHLNWFRSHKFDKO-UHFFFAOYSA-N 0.000 claims description 2
- SOHMVPMBRQNXCG-UHFFFAOYSA-N [2-bromo-4-[5-(2-tert-butylpyridin-4-yl)furan-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1Cl)C1=COC(=C1)C1=CC(=NC=C1)C(C)(C)C)C(=O)N1CCCCC1 SOHMVPMBRQNXCG-UHFFFAOYSA-N 0.000 claims description 2
- FEJMXZYJOWWVFR-UHFFFAOYSA-N [2-bromo-4-[5-(2-tert-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1Cl)C1=CSC(=C1)C1=CC(=NC=C1)C(C)(C)C)C(=O)N1CCCCC1 FEJMXZYJOWWVFR-UHFFFAOYSA-N 0.000 claims description 2
- WGUYRCOENBPFKZ-UHFFFAOYSA-N [2-bromo-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 WGUYRCOENBPFKZ-UHFFFAOYSA-N 0.000 claims description 2
- VHKCTUFUJZVMQB-UHFFFAOYSA-N [2-bromo-5-chloro-4-[1-methyl-2-[2-(2-methylpropyl)pyridin-4-yl]imidazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=C(C(=C1)C=1N=C(N(C=1)C)C1=CC(=NC=C1)CC(C)C)Cl)C(=O)N1CCCCC1 VHKCTUFUJZVMQB-UHFFFAOYSA-N 0.000 claims description 2
- GORLPFXWSHFNSW-UHFFFAOYSA-N [2-bromo-5-chloro-4-[2-(2-propylpyridin-4-yl)-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C=C(C(=C1)C=1N=C(NC=1)C1=CC(=NC=C1)CCC)Cl)C(=O)N1CCCCC1 GORLPFXWSHFNSW-UHFFFAOYSA-N 0.000 claims description 2
- YGAWFQLZWNJAJP-UHFFFAOYSA-N [2-bromo-6-chloro-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound BrC1=C(C(=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)Cl)C(=O)N1CCCCC1 YGAWFQLZWNJAJP-UHFFFAOYSA-N 0.000 claims description 2
- WNYSCSSHEOAJFC-UHFFFAOYSA-N [2-chloro-4-[2-(2-propylpyridin-4-yl)-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC1=C(C=CC(=C1)C=1N=C(NC=1)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 WNYSCSSHEOAJFC-UHFFFAOYSA-N 0.000 claims description 2
- FWFMWVFXZLOUTF-UHFFFAOYSA-N [2-chloro-6-methyl-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC1=C(C(=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C)C(=O)N1CCCCC1 FWFMWVFXZLOUTF-UHFFFAOYSA-N 0.000 claims description 2
- GDGAOUIYCBMYCH-UHFFFAOYSA-N [2-cyclopropyl-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C1(CC1)C1=C(C=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 GDGAOUIYCBMYCH-UHFFFAOYSA-N 0.000 claims description 2
- TYBDRAZDUOBUJV-UHFFFAOYSA-N [2-ethynyl-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C(#C)C1=C(C=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 TYBDRAZDUOBUJV-UHFFFAOYSA-N 0.000 claims description 2
- WXWLHNWSDUXXDK-UHFFFAOYSA-N [2-hydroxy-4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound OC1=C(C=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 WXWLHNWSDUXXDK-UHFFFAOYSA-N 0.000 claims description 2
- IBGQGGKPRCRWST-UHFFFAOYSA-N [2-hydroxy-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound OC1=C(C=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 IBGQGGKPRCRWST-UHFFFAOYSA-N 0.000 claims description 2
- VRFYUFGZCSOOIL-UHFFFAOYSA-N [2-methoxy-4-[1-methyl-2-(2-propylpyridin-4-yl)imidazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound COC1=C(C=CC(=C1)C=1N=C(N(C=1)C)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 VRFYUFGZCSOOIL-UHFFFAOYSA-N 0.000 claims description 2
- LZUUTHCFALTNFG-UHFFFAOYSA-N [2-methoxy-4-[1-methyl-2-[2-(2-methylpropyl)pyridin-4-yl]imidazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C(C(C)C)C1=NC=CC(=C1)C=1N(C=C(N=1)C1=CC(=C(C=C1)C(=O)N1CCCCC1)OC)C LZUUTHCFALTNFG-UHFFFAOYSA-N 0.000 claims description 2
- ICAQOKKBXADVPV-UHFFFAOYSA-N [2-methoxy-4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound COC1=C(C=CC(=C1)C1=CSC(=C1)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 ICAQOKKBXADVPV-UHFFFAOYSA-N 0.000 claims description 2
- GSSXXASYOPTXTA-UHFFFAOYSA-N [2-methoxy-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)OC GSSXXASYOPTXTA-UHFFFAOYSA-N 0.000 claims description 2
- TXJYXLSSSLOCIX-UHFFFAOYSA-N [2-methyl-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)C TXJYXLSSSLOCIX-UHFFFAOYSA-N 0.000 claims description 2
- ZLAILEUOTDJZQZ-UHFFFAOYSA-N [3,5-dichloro-4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=C(C=1C1=CSC(=C1)C1=CC(=NC=C1)CCC)Cl)C(=O)N1CCCCC1 ZLAILEUOTDJZQZ-UHFFFAOYSA-N 0.000 claims description 2
- UKNWHXSUSMUWBF-UHFFFAOYSA-N [3,5-dichloro-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=C(C=1C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)Cl)C(=O)N1CCCCC1 UKNWHXSUSMUWBF-UHFFFAOYSA-N 0.000 claims description 2
- JZIIOHJDWNEBMR-UHFFFAOYSA-N [3-[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)C=1C=C(C=CC=1)C(=O)N1CCCCC1 JZIIOHJDWNEBMR-UHFFFAOYSA-N 0.000 claims description 2
- YBALUPZIZLDGST-UHFFFAOYSA-N [3-chloro-4-(5-isoquinolin-4-ylthiophen-3-yl)phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CN=CC2=CC=CC=C12)C(=O)N1CCCCC1 YBALUPZIZLDGST-UHFFFAOYSA-N 0.000 claims description 2
- QXSDLBJFUOSUKV-UHFFFAOYSA-N [3-chloro-4-(5-naphthalen-1-ylthiophen-3-yl)phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC=CC2=CC=CC=C12)C(=O)N1CCCCC1 QXSDLBJFUOSUKV-UHFFFAOYSA-N 0.000 claims description 2
- PQZVURKDSHGGMC-UHFFFAOYSA-N [3-chloro-4-(5-quinolin-4-ylthiophen-3-yl)phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC=NC2=CC=CC=C12)C(=O)N1CCCCC1 PQZVURKDSHGGMC-UHFFFAOYSA-N 0.000 claims description 2
- UZNPCRHCSGHGNK-UHFFFAOYSA-N [3-chloro-4-[1-methyl-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C=1N=C(N(C=1)C)C1=C2C(=NC=C1)NC=C2)C(=O)N1CCCCC1 UZNPCRHCSGHGNK-UHFFFAOYSA-N 0.000 claims description 2
- YRMYYIJXYMXVEH-UHFFFAOYSA-N [3-chloro-4-[2-(1H-indol-4-yl)-1,3-thiazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC1=C(C=CC(=C1)C(=O)N1CCCCC1)C=1N=C(SC=1)C1=C2C=CNC2=CC=C1 YRMYYIJXYMXVEH-UHFFFAOYSA-N 0.000 claims description 2
- ZRNPABAXBNTOPH-UHFFFAOYSA-N [3-chloro-4-[2-(1H-indol-4-yl)-1-methylimidazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound N1C=CC2=C(C=CC=C12)C=1N(C=C(N=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl)C ZRNPABAXBNTOPH-UHFFFAOYSA-N 0.000 claims description 2
- DKNDNMNRQVSHSP-UHFFFAOYSA-N [3-chloro-4-[2-(2-piperidin-1-ylpyridin-4-yl)-1,3-thiazol-4-yl]phenyl]-morpholin-4-ylmethanone Chemical compound ClC=1C=C(C(=O)N2CCOCC2)C=CC=1C=1N=C(SC=1)C1=CC(=NC=C1)N1CCCCC1 DKNDNMNRQVSHSP-UHFFFAOYSA-N 0.000 claims description 2
- DBHWYZNDJPCKOP-UHFFFAOYSA-N [3-chloro-4-[2-(2-propylpyridin-4-yl)-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C=1N=C(NC=1)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 DBHWYZNDJPCKOP-UHFFFAOYSA-N 0.000 claims description 2
- VXIQMOCKCIUEHO-UHFFFAOYSA-N [3-chloro-4-[2-[2-(2-methylpropyl)pyridin-4-yl]-1,3-oxazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C=1N=C(OC=1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 VXIQMOCKCIUEHO-UHFFFAOYSA-N 0.000 claims description 2
- RNXBSZSOHRAENX-UHFFFAOYSA-N [3-chloro-4-[2-[2-(2-methylpropyl)pyridin-4-yl]-1,3-thiazol-4-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C=1N=C(SC=1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 RNXBSZSOHRAENX-UHFFFAOYSA-N 0.000 claims description 2
- SVQMNIXHOPSUDA-UHFFFAOYSA-N [3-chloro-4-[2-[2-(2-methylpropyl)pyridin-4-yl]-1H-imidazol-5-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C=1N=C(NC=1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 SVQMNIXHOPSUDA-UHFFFAOYSA-N 0.000 claims description 2
- ORMFDQJQQCYLLP-UHFFFAOYSA-N [3-chloro-4-[4-(2-piperidin-1-ylpyridin-4-yl)thiophen-2-yl]phenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound ClC=1C=C(C=CC=1C=1SC=C(C=1)C1=CC(=NC=C1)N1CCCCC1)C(=O)N1CCC(CC1)(F)F ORMFDQJQQCYLLP-UHFFFAOYSA-N 0.000 claims description 2
- MPVIGIJCATUHGC-UHFFFAOYSA-N [3-chloro-4-[4-(2-piperidin-1-ylpyridin-4-yl)thiophen-2-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C=1SC=C(C=1)C1=CC(=NC=C1)N1CCCCC1)C(=O)N1CCCCC1 MPVIGIJCATUHGC-UHFFFAOYSA-N 0.000 claims description 2
- IHZHITGJAXWFLL-UHFFFAOYSA-N [3-chloro-4-[4-[2-(3-methylbutyl)pyrazol-3-yl]thiophen-2-yl]phenyl]-(3-hydroxypiperidin-1-yl)methanone Chemical compound ClC=1C=C(C(=O)N2CC(CCC2)O)C=CC=1C=1SC=C(C=1)C1=CC=NN1CCC(C)C IHZHITGJAXWFLL-UHFFFAOYSA-N 0.000 claims description 2
- CVMGVSPTWHOQSW-UHFFFAOYSA-N [3-chloro-4-[5-(1,2-dimethylpyrrolo[2,3-b]pyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C2C(=NC=C1)N(C(=C2)C)C)C(=O)N1CCCCC1 CVMGVSPTWHOQSW-UHFFFAOYSA-N 0.000 claims description 2
- ZLJWDZQNAISHGI-UHFFFAOYSA-N [3-chloro-4-[5-(1,2-dipropylpyrrolo[2,3-b]pyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C2C(=NC=C1)N(C(=C2)CCC)CCC)C(=O)N1CCCCC1 ZLJWDZQNAISHGI-UHFFFAOYSA-N 0.000 claims description 2
- MOQALAGCVBBPCS-UHFFFAOYSA-N [3-chloro-4-[5-(1-ethylbenzimidazol-4-yl)thiophen-3-yl]phenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC=CC=2N(C=NC=21)CC)C(=O)N1CCC(CC1)(F)F MOQALAGCVBBPCS-UHFFFAOYSA-N 0.000 claims description 2
- XGZNGKAECWSANZ-UHFFFAOYSA-N [3-chloro-4-[5-(1H-imidazo[4,5-b]pyridin-7-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound N1=CNC2=NC=CC(=C21)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl XGZNGKAECWSANZ-UHFFFAOYSA-N 0.000 claims description 2
- JRSREDPWZRNNKQ-UHFFFAOYSA-N [3-chloro-4-[5-(1H-indol-3-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound N1C=C(C2=CC=CC=C12)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl JRSREDPWZRNNKQ-UHFFFAOYSA-N 0.000 claims description 2
- OTETWTMUPRFLTF-UHFFFAOYSA-N [3-chloro-4-[5-(1H-indol-4-yl)thiophen-3-yl]phenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound N1C=CC2=C(C=CC=C12)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCC(CC1)(F)F)Cl OTETWTMUPRFLTF-UHFFFAOYSA-N 0.000 claims description 2
- SXJRZQAPJXFFGN-UHFFFAOYSA-N [3-chloro-4-[5-(1H-indol-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound N1C=CC2=C(C=CC=C12)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl SXJRZQAPJXFFGN-UHFFFAOYSA-N 0.000 claims description 2
- LQFSFCNKCQFDKV-UHFFFAOYSA-N [3-chloro-4-[5-(1H-indol-6-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound N1C=CC2=CC=C(C=C12)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl LQFSFCNKCQFDKV-UHFFFAOYSA-N 0.000 claims description 2
- PENRLGGSCLLFOD-UHFFFAOYSA-N [3-chloro-4-[5-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound N1C=CC=2C1=NC=CC=2C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl PENRLGGSCLLFOD-UHFFFAOYSA-N 0.000 claims description 2
- UHIKUWACLXTVER-UHFFFAOYSA-N [3-chloro-4-[5-(2,3-dihydro-1-benzofuran-5-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C=1C=CC2=C(CCO2)C=1)C(=O)N1CCCCC1 UHIKUWACLXTVER-UHFFFAOYSA-N 0.000 claims description 2
- WOEANSGTYNBYRF-UHFFFAOYSA-N [3-chloro-4-[5-(2,3-dimethylimidazo[4,5-b]pyridin-7-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C2C(=NC=C1)N(C(=N2)C)C)C(=O)N1CCCCC1 WOEANSGTYNBYRF-UHFFFAOYSA-N 0.000 claims description 2
- LGLGCMBXWLBAMK-UHFFFAOYSA-N [3-chloro-4-[5-(2-chloropyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)Cl)C(=O)N1CCCCC1 LGLGCMBXWLBAMK-UHFFFAOYSA-N 0.000 claims description 2
- CZYQRRMURCDGIB-UHFFFAOYSA-N [3-chloro-4-[5-(2-cyclopropylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)C1CC1)C(=O)N1CCCCC1 CZYQRRMURCDGIB-UHFFFAOYSA-N 0.000 claims description 2
- KOKMVLLEVBMRJL-UHFFFAOYSA-N [3-chloro-4-[5-(2-morpholin-4-ylpyridin-4-yl)thiophen-3-yl]phenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)N1CCOCC1)C(=O)N1CCC(CC1)(F)F KOKMVLLEVBMRJL-UHFFFAOYSA-N 0.000 claims description 2
- NDYJKRIGYWOSFT-UHFFFAOYSA-N [3-chloro-4-[5-(2-piperidin-1-ylpyridin-4-yl)thiophen-3-yl]phenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)N1CCCCC1)C(=O)N1CCC(CC1)(F)F NDYJKRIGYWOSFT-UHFFFAOYSA-N 0.000 claims description 2
- IKOFGNSDEOTBOW-UHFFFAOYSA-N [3-chloro-4-[5-(2-piperidin-1-ylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)N1CCCCC1)C(=O)N1CCCCC1 IKOFGNSDEOTBOW-UHFFFAOYSA-N 0.000 claims description 2
- TVJHAVZJLVTSLP-UHFFFAOYSA-N [3-chloro-4-[5-(2-propyl-1,3-thiazol-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C=1N=C(SC=1)CCC)C(=O)N1CCCCC1 TVJHAVZJLVTSLP-UHFFFAOYSA-N 0.000 claims description 2
- ATFKQHVUPWPCTD-UHFFFAOYSA-N [3-chloro-4-[5-(2-propyl-1,3-thiazol-5-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CN=C(S1)CCC)C(=O)N1CCCCC1 ATFKQHVUPWPCTD-UHFFFAOYSA-N 0.000 claims description 2
- GLDHGYOHKDVCOG-UHFFFAOYSA-N [3-chloro-4-[5-(2-propyl-1H-imidazo[4,5-b]pyridin-7-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C2C(=NC=C1)NC(=N2)CCC)C(=O)N1CCCCC1 GLDHGYOHKDVCOG-UHFFFAOYSA-N 0.000 claims description 2
- HFFYQHIPECIBQP-UHFFFAOYSA-N [3-chloro-4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]-(3,3-difluoropyrrolidin-1-yl)methanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CCC)C(=O)N1CC(CC1)(F)F HFFYQHIPECIBQP-UHFFFAOYSA-N 0.000 claims description 2
- SSUOOGPLQIVJNC-UHFFFAOYSA-N [3-chloro-4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 SSUOOGPLQIVJNC-UHFFFAOYSA-N 0.000 claims description 2
- SHYZBLWDPQUFFY-UHFFFAOYSA-N [3-chloro-4-[5-(3,5-dimethyl-1,2-oxazol-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C=1C(=NOC=1C)C)C(=O)N1CCCCC1 SHYZBLWDPQUFFY-UHFFFAOYSA-N 0.000 claims description 2
- ZVQZVFULCYWSSO-UHFFFAOYSA-N [3-chloro-4-[5-(3-methylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C(C=NC=C1)C)C(=O)N1CCCCC1 ZVQZVFULCYWSSO-UHFFFAOYSA-N 0.000 claims description 2
- HJUJMAZHNBEDHC-UHFFFAOYSA-N [3-chloro-4-[5-(3-propylimidazo[4,5-b]pyridin-7-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C2C(=NC=C1)N(C=N2)CCC)C(=O)N1CCCCC1 HJUJMAZHNBEDHC-UHFFFAOYSA-N 0.000 claims description 2
- CPHADNAEEHBTAO-UHFFFAOYSA-N [3-chloro-4-[5-(4,6-dipropylpyridin-2-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=NC(=CC(=C1)CCC)CCC)C(=O)N1CCCCC1 CPHADNAEEHBTAO-UHFFFAOYSA-N 0.000 claims description 2
- NURKTMDQBFUXID-UHFFFAOYSA-N [3-chloro-4-[5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C2C(=NC=C1F)NC=C2)C(=O)N1CCCCC1 NURKTMDQBFUXID-UHFFFAOYSA-N 0.000 claims description 2
- YHXHDCDGXMXQAG-UHFFFAOYSA-N [3-chloro-4-[5-(5-propyl-1,2,4-oxadiazol-3-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=NOC(=N1)CCC)C(=O)N1CCCCC1 YHXHDCDGXMXQAG-UHFFFAOYSA-N 0.000 claims description 2
- KLTZNSZKYFHDBK-UHFFFAOYSA-N [3-chloro-4-[5-(5-propyl-1,2,4-thiadiazol-3-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=NSC(=N1)CCC)C(=O)N1CCCCC1 KLTZNSZKYFHDBK-UHFFFAOYSA-N 0.000 claims description 2
- AQQGCVZDCFBELA-UHFFFAOYSA-N [3-chloro-4-[5-(5-propyl-1,3,4-oxadiazol-2-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C=1OC(=NN=1)CCC)C(=O)N1CCCCC1 AQQGCVZDCFBELA-UHFFFAOYSA-N 0.000 claims description 2
- QCTBHEZCVFEECP-UHFFFAOYSA-N [3-chloro-4-[5-(5-propyl-1,3,4-thiadiazol-2-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C=1SC(=NN=1)CCC)C(=O)N1CCCCC1 QCTBHEZCVFEECP-UHFFFAOYSA-N 0.000 claims description 2
- ZXXQPDNHZGQBAH-UHFFFAOYSA-N [3-chloro-4-[5-[2-(2,2-dimethylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CC(C)(C)C)C(=O)N1CCCCC1 ZXXQPDNHZGQBAH-UHFFFAOYSA-N 0.000 claims description 2
- MAYZYKQHSBCLGB-UHFFFAOYSA-N [3-chloro-4-[5-[2-(2-methylpropyl)pyridin-4-yl]-1H-pyrrol-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CNC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 MAYZYKQHSBCLGB-UHFFFAOYSA-N 0.000 claims description 2
- PKPLGEYTHXHIBY-UHFFFAOYSA-N [3-chloro-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]-5-(trifluoromethyl)phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=C(C=1C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(F)(F)F)C(=O)N1CCCCC1 PKPLGEYTHXHIBY-UHFFFAOYSA-N 0.000 claims description 2
- DKAPAFAXFURONC-UHFFFAOYSA-N [3-chloro-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCC(CC1)(F)F DKAPAFAXFURONC-UHFFFAOYSA-N 0.000 claims description 2
- QBPRVNCVMHDCSM-UHFFFAOYSA-N [3-chloro-4-[5-[2-(2-methylpropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CC(C)C)C(=O)N1CCCCC1 QBPRVNCVMHDCSM-UHFFFAOYSA-N 0.000 claims description 2
- PDKYRXFXXRLYFG-UHFFFAOYSA-N [3-chloro-4-[5-[2-(3,3,3-trifluoropropyl)pyridin-4-yl]furan-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=COC(=C1)C1=CC(=NC=C1)CCC(F)(F)F)C(=O)N1CCCCC1 PDKYRXFXXRLYFG-UHFFFAOYSA-N 0.000 claims description 2
- FIGPOSXVHGAOPY-UHFFFAOYSA-N [3-chloro-4-[5-[2-(3,3,3-trifluoropropyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CCC(F)(F)F)C(=O)N1CCCCC1 FIGPOSXVHGAOPY-UHFFFAOYSA-N 0.000 claims description 2
- SJVUCYXFSUORHR-UHFFFAOYSA-N [3-chloro-4-[5-[2-(3-methylbutyl)pyrazol-3-yl]furan-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=COC(=C1)C1=CC=NN1CCC(C)C)C(=O)N1CCCCC1 SJVUCYXFSUORHR-UHFFFAOYSA-N 0.000 claims description 2
- JZEVAZOCBZKUGZ-UHFFFAOYSA-N [3-chloro-4-[5-[2-(3-methylbutyl)pyrazol-3-yl]thiophen-3-yl]phenyl]-morpholin-4-ylmethanone Chemical compound ClC=1C=C(C(=O)N2CCOCC2)C=CC=1C1=CSC(=C1)C1=CC=NN1CCC(C)C JZEVAZOCBZKUGZ-UHFFFAOYSA-N 0.000 claims description 2
- PUVXKQAPNAILNY-UHFFFAOYSA-N [3-chloro-4-[5-[2-(3-methylbutyl)pyrazol-3-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC=NN1CCC(C)C)C(=O)N1CCCCC1 PUVXKQAPNAILNY-UHFFFAOYSA-N 0.000 claims description 2
- FYWHTYUAKVBRFY-UHFFFAOYSA-N [3-chloro-4-[5-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)N1CCN(CC1)C)C(=O)N1CCCCC1 FYWHTYUAKVBRFY-UHFFFAOYSA-N 0.000 claims description 2
- NQJNLQXQCGSMMQ-UHFFFAOYSA-N [3-chloro-4-[5-[2-(cyclohexylmethyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CC1CCCCC1)C(=O)N1CCCCC1 NQJNLQXQCGSMMQ-UHFFFAOYSA-N 0.000 claims description 2
- ODOJZKQVQKAXQS-UHFFFAOYSA-N [3-chloro-4-[5-[2-(cyclopentylamino)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)NC1CCCC1)C(=O)N1CCCCC1 ODOJZKQVQKAXQS-UHFFFAOYSA-N 0.000 claims description 2
- CIKXMOCOROSWSW-UHFFFAOYSA-N [3-chloro-4-[5-[2-(dimethylamino)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)N(C)C)C(=O)N1CCCCC1 CIKXMOCOROSWSW-UHFFFAOYSA-N 0.000 claims description 2
- TZTYTUMAITVVIV-UHFFFAOYSA-N [3-chloro-4-[5-[2-(hydroxymethyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CO)C(=O)N1CCCCC1 TZTYTUMAITVVIV-UHFFFAOYSA-N 0.000 claims description 2
- PELKJHQPBGTSQM-UHFFFAOYSA-N [3-chloro-4-[5-[2-(methoxymethyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)COC)C(=O)N1CCCCC1 PELKJHQPBGTSQM-UHFFFAOYSA-N 0.000 claims description 2
- USJJUYKMTKUHBS-UHFFFAOYSA-N [3-chloro-4-[5-[2-(propylamino)pyrimidin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=NC(=NC=C1)NCCC)C(=O)N1CCCCC1 USJJUYKMTKUHBS-UHFFFAOYSA-N 0.000 claims description 2
- YFUPLBJKWCSAJB-UHFFFAOYSA-N [3-chloro-4-[5-[2-(trifluoromethylsulfonylmethyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CS(=O)(=O)C(F)(F)F)C(=O)N1CCCCC1 YFUPLBJKWCSAJB-UHFFFAOYSA-N 0.000 claims description 2
- PISZMNSXVFDXNL-UHFFFAOYSA-N [3-chloro-4-[5-[3-(hydroxymethyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C(C=NC=C1)CO)C(=O)N1CCCCC1 PISZMNSXVFDXNL-UHFFFAOYSA-N 0.000 claims description 2
- UESXTQSVCWKRPY-UHFFFAOYSA-N [3-chloro-4-[5-[3-(pyrrolidin-1-ylmethyl)pyridin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=C(C=NC=C1)CN1CCCC1)C(=O)N1CCCCC1 UESXTQSVCWKRPY-UHFFFAOYSA-N 0.000 claims description 2
- WPVQQOWSBVYZGK-UHFFFAOYSA-N [3-chloro-4-[5-[6-(dibutylamino)-2-(2-methylpropyl)pyrimidin-4-yl]thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound ClC=1C=C(C=CC=1C1=CSC(=C1)C1=NC(=NC(=C1)N(CCCC)CCCC)CC(C)C)C(=O)N1CCCCC1 WPVQQOWSBVYZGK-UHFFFAOYSA-N 0.000 claims description 2
- QTIDTUJTBZRYKD-UHFFFAOYSA-N [3-fluoro-4-[5-(2-propylpyridin-4-yl)thiophen-3-yl]phenyl]-piperidin-1-ylmethanone Chemical compound FC=1C=C(C=CC=1C1=CSC(=C1)C1=CC(=NC=C1)CCC)C(=O)N1CCCCC1 QTIDTUJTBZRYKD-UHFFFAOYSA-N 0.000 claims description 2
- RICTYTQRDQUTGI-UHFFFAOYSA-N [3-methoxy-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=C(C=C(C=C1)C(=O)N1CCCCC1)OC RICTYTQRDQUTGI-UHFFFAOYSA-N 0.000 claims description 2
- DVZKYCSEDFMLII-UHFFFAOYSA-N [4-[2-(2-tert-butylpyridin-4-yl)-1,3-oxazol-4-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1OC=C(N=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl DVZKYCSEDFMLII-UHFFFAOYSA-N 0.000 claims description 2
- GGKBDPNYLOIUQK-UHFFFAOYSA-N [4-[2-(2-tert-butylpyridin-4-yl)-1,3-thiazol-4-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1SC=C(N=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl GGKBDPNYLOIUQK-UHFFFAOYSA-N 0.000 claims description 2
- MLWGODUZZAZTDK-UHFFFAOYSA-N [4-[2-(2-tert-butylpyridin-4-yl)-1-methylimidazol-4-yl]-2-methoxyphenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1N(C=C(N=1)C1=CC(=C(C=C1)C(=O)N1CCCCC1)OC)C MLWGODUZZAZTDK-UHFFFAOYSA-N 0.000 claims description 2
- ZIMGKYVNKZJTPF-UHFFFAOYSA-N [4-[2-(2-tert-butylpyridin-4-yl)-1-methylimidazol-4-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1N(C=C(N=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl)C ZIMGKYVNKZJTPF-UHFFFAOYSA-N 0.000 claims description 2
- FWTHBHUOTUQLLC-UHFFFAOYSA-N [4-[2-(2-tert-butylpyridin-4-yl)-1H-imidazol-5-yl]-3-chlorophenyl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1NC=C(N=1)C1=C(C=C(C=C1)C(=O)N1CCC(CC1)(F)F)Cl FWTHBHUOTUQLLC-UHFFFAOYSA-N 0.000 claims description 2
- ZTOAYGNJTYIAPP-UHFFFAOYSA-N [4-[2-(2-tert-butylpyridin-4-yl)-1H-imidazol-5-yl]-3-chlorophenyl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1NC=C(N=1)C1=C(C=C(C(=O)N2CCC(CC2)O)C=C1)Cl ZTOAYGNJTYIAPP-UHFFFAOYSA-N 0.000 claims description 2
- UBERXEBPXUXCQE-UHFFFAOYSA-N [4-[2-(2-tert-butylpyridin-4-yl)-1H-imidazol-5-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1NC=C(N=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl UBERXEBPXUXCQE-UHFFFAOYSA-N 0.000 claims description 2
- DTMXDKDVOJGAGN-UHFFFAOYSA-N [4-[2-(2-tert-butylpyridin-4-yl)-1H-imidazol-5-yl]-3-fluorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1NC=C(N=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)F DTMXDKDVOJGAGN-UHFFFAOYSA-N 0.000 claims description 2
- 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
- ZJERAOBNSUBJPA-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)-1,3-thiazol-2-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1N=C(SC=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl ZJERAOBNSUBJPA-UHFFFAOYSA-N 0.000 claims description 2
- OJNORIYYJVTMGS-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)-1-methylimidazol-2-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1N=C(N(C=1)C)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl OJNORIYYJVTMGS-UHFFFAOYSA-N 0.000 claims description 2
- WKRLYNMLJGSKOV-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)-1-methylpyrrol-2-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(N(C=1)C)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl WKRLYNMLJGSKOV-UHFFFAOYSA-N 0.000 claims description 2
- 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
- OYLJSYMEMPJCEW-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)methanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=CSC(=C1)C1=C(C=C(C=C1)C(=O)N1CC2=C(CC1)N=CN2)Cl OYLJSYMEMPJCEW-UHFFFAOYSA-N 0.000 claims description 2
- FFCQZTLKNZTJLZ-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-(3,4-dihydro-2H-1,5-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=NC=CC=C23)C=C1)Cl FFCQZTLKNZTJLZ-UHFFFAOYSA-N 0.000 claims description 2
- 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
- OFTSQXPYFCWPMZ-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-(4-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)N2CCC(CC2)O)C=C1)Cl OFTSQXPYFCWPMZ-UHFFFAOYSA-N 0.000 claims description 2
- 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
- YCASEBCIHMPGQI-UHFFFAOYSA-N [4-[4-(2-tert-butylpyridin-4-yl)thiophen-2-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C=1C=C(SC=1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl YCASEBCIHMPGQI-UHFFFAOYSA-N 0.000 claims description 2
- KYSGLDJLOSSVQX-UHFFFAOYSA-N [4-[5-(1-benzothiophen-3-yl)thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound S1C2=C(C(=C1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl)C=CC=C2 KYSGLDJLOSSVQX-UHFFFAOYSA-N 0.000 claims description 2
- 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
- VMBFVKUTYUTEDE-UHFFFAOYSA-N [4-[5-(2-butylpyridin-4-yl)thiophen-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(CCC)C1=NC=CC(=C1)C1=CC(=CS1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl VMBFVKUTYUTEDE-UHFFFAOYSA-N 0.000 claims description 2
- 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
- VTKNZBSWPSCAQM-UHFFFAOYSA-N [4-[5-(2-tert-butylpyridin-4-yl)-2-methylpyrazol-3-yl]-3-chlorophenyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C1=NN(C(=C1)C1=C(C=C(C=C1)C(=O)N1CCCCC1)Cl)C VTKNZBSWPSCAQM-UHFFFAOYSA-N 0.000 claims description 2
- 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
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN615/DEL/2015 | 2015-03-04 | ||
| IN615DE2015 | 2015-03-04 | ||
| IN640DE2015 | 2015-03-09 | ||
| IN640/DEL/2015 | 2015-03-09 | ||
| PCT/US2016/020802 WO2016141258A1 (en) | 2015-03-04 | 2016-03-04 | Sterol regulatory element-binding proteins (srebps) inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018507235A JP2018507235A (ja) | 2018-03-15 |
| JP2018507235A5 true JP2018507235A5 (enExample) | 2019-04-18 |
Family
ID=55586426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017546186A Withdrawn JP2018507235A (ja) | 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 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10189826B2 (enExample) |
| EP (1) | EP3265457A1 (enExample) |
| JP (1) | JP2018507235A (enExample) |
| CA (1) | CA2977539A1 (enExample) |
| WO (1) | WO2016141258A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016105491A1 (en) | 2014-12-23 | 2016-06-30 | Fgh Biotech | Compositions of fatostatin based heterocyclic compounds and uses thereof |
| CA2978627A1 (en) | 2015-03-04 | 2016-09-09 | Medivation Technologies, Inc. | Srebp blockers for use in treating liver fibrosis, elevated cholesterol and insulin resistance |
| WO2017190086A1 (en) | 2016-04-29 | 2017-11-02 | Fgh Biotech, Inc. | Di-substituted pyrazole compounds for the treatment of diseases |
| WO2018049080A1 (en) | 2016-09-07 | 2018-03-15 | Fgh Biotech, Inc. | Di-substituted pyrazole compounds for the treatment of diseases |
| JP2021512160A (ja) * | 2018-01-29 | 2021-05-13 | カピュラス セラピューティクス リミテッド ライアビリティ カンパニー | ６員の中央環を含むｓｒｅｂｐ阻害剤 |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| WO2020132700A1 (en) | 2018-12-21 | 2020-06-25 | Fgh Biotech Inc. | Methods of using inhibitors of srebp in combination with niclosamide and analogs thereof |
| CN113631163A (zh) * | 2019-01-28 | 2021-11-09 | 卡普勒斯疗法有限责任公司 | 包括噻吩中心环的srebp抑制剂 |
| AU2020381462A1 (en) * | 2019-11-13 | 2022-06-02 | Capulus Therapeutics, Llc | SREBP inhibitor comprising a thiophene central ring |
| TW202128676A (zh) * | 2019-11-13 | 2021-08-01 | 美商卡普勒斯療法有限責任公司 | 具有環醯胺的噻吩化合物及其用途 |
| EP4096659A4 (en) * | 2020-01-27 | 2023-10-18 | Capulus Therapeutics, LLC | Srebp inhibitors comprising a thiophene central ring |
| EP4185584A1 (en) * | 2020-07-24 | 2023-05-31 | Capulus Therapeutics, LLC | Srebp inhibitors comprising a thiophene central ring |
| CN112225728A (zh) * | 2020-08-18 | 2021-01-15 | 四川农业大学 | 一种多取代苯甲酰胺化合物及其制备方法和应用 |
| CN117050074B (zh) * | 2022-05-05 | 2025-08-12 | 中国药科大学 | 一类吡啶联咪唑并吡啶化合物及其制备方法与用途 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL96891A0 (en) | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| WO1999040088A1 (en) | 1998-02-09 | 1999-08-12 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines as protease inhibitors, in particular as urokinase inhibitors |
| US6291514B1 (en) | 1998-02-09 | 2001-09-18 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines, preparation thereof, and use thereof as protease inhibitors |
| AR032292A1 (es) | 1999-12-16 | 2003-11-05 | Schering Corp | Imidazoles sustituidos, composiciones farmaceuticas y el uso de dichos imidazoles para la manufactura de un medicamento para los tratamientos de desordenes en la alimentacion |
| AR029686A1 (es) | 2000-06-22 | 2003-07-10 | Dow Agrosciences Llc | Compuestos de 2-(3,5-disustituido-4-piridil)-4-(tienilo, tiazolilo o arilfenil)-1,3-oxazolina, composiciones y metodos para el control de insectos o acaros y/o plantas utilizando dichos compuestos |
| EP1628666B1 (en) | 2003-05-14 | 2015-09-23 | NeuroGenetic Pharmaceuticals, Inc. | Compouds and uses thereof in modulating amyloid beta |
| EP1893591A1 (en) | 2005-06-08 | 2008-03-05 | Novartis AG | POLYCYCLIC OXADIAZOLES OR I SOXAZOLES AND THEIR USE AS SlP RECEPTOR LIGANDS |
| AR054380A1 (es) | 2005-06-09 | 2007-06-20 | Schering Plough Ltd | Control de parasitos en animales con derivados de n- ((feniloxi) fenil) -1,1,1-trifluorometansulfonamida y de n-(fenilsulfanil) fenil) -1,1,1-trifluorometansulfonamida |
| CA2616377C (en) | 2005-07-26 | 2014-04-01 | David Alexander Learmonth | Nitrocatechol derivatives as comt inhibitors |
| EP1922068A4 (en) | 2005-08-16 | 2010-08-11 | Icagen Inc | INHIBITORS OF VOLTAGE-CONTROLLED SODIUM CHANNELS |
| US8229106B2 (en) | 2007-01-22 | 2012-07-24 | D.S.P. Group, Ltd. | Apparatus and methods for enhancement of speech |
| AU2008214095B2 (en) | 2007-02-02 | 2014-07-10 | Baylor College Of Medicine | Compositions and methods for the treatment of metabolic disorders |
| US9187485B2 (en) | 2007-02-02 | 2015-11-17 | Baylor College Of Medicine | Methods and compositions for the treatment of cancer and related hyperproliferative disorders |
| US9212179B2 (en) | 2007-02-02 | 2015-12-15 | Baylor College Of Medicine | Compositions and methods for the treatment of metabolic disorders |
| NZ580454A (en) * | 2007-03-16 | 2011-05-27 | Actelion Pharmaceuticals Ltd | Amino- pyridine derivatives as s1p1 /edg1 receptor agonists |
| CN101918395B (zh) | 2007-12-21 | 2014-04-16 | 默克雪兰诺有限公司 | 三唑联噁二唑衍生物 |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| CA2786424A1 (en) | 2010-01-08 | 2011-07-14 | Ruga Corporation | Raf kinase inhibitors |
| WO2012084678A1 (en) | 2010-12-23 | 2012-06-28 | Syngenta Participations Ag | Novel imidazoles useful as plant fungicides |
| JP2014062047A (ja) | 2011-01-21 | 2014-04-10 | Taisho Pharmaceutical Co Ltd | ピラゾール誘導体 |
| GB201116017D0 (en) | 2011-09-16 | 2011-10-26 | Univ Surrey | Bi-aromatic and tri-aromatic compounds as nadph oxidase inhibitors |
| WO2013096642A1 (en) | 2011-12-23 | 2013-06-27 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2013110007A1 (en) | 2012-01-18 | 2013-07-25 | The Trustees Of Columbia University In The City Of New York | USE OF FATOSTATIN FOR TREATING CANCER HAVING A p53 MUTATION |
| WO2014199164A1 (en) | 2013-06-12 | 2014-12-18 | Ampla Pharmaceuticals, Inc. | Diaryl substituted heteroaromatic compounds |
| EP3013371A4 (en) | 2013-06-26 | 2017-04-26 | Rett Syndrome Research Trust | Rett syndrome and treatments therefore |
| KR20160067841A (ko) | 2013-08-28 | 2016-06-14 | 메디베이션 테크놀로지즈, 인크. | 헤테로사이클릭 화합물 및 사용 방법 |
| CA2978627A1 (en) | 2015-03-04 | 2016-09-09 | Medivation Technologies, Inc. | Srebp blockers for use in treating liver fibrosis, elevated cholesterol and insulin resistance |
-
2016
- 2016-03-04 CA CA2977539A patent/CA2977539A1/en not_active Abandoned
- 2016-03-04 JP JP2017546186A patent/JP2018507235A/ja not_active Withdrawn
- 2016-03-04 WO PCT/US2016/020802 patent/WO2016141258A1/en not_active Ceased
- 2016-03-04 EP EP16710893.5A patent/EP3265457A1/en not_active Withdrawn
- 2016-03-04 US US15/553,622 patent/US10189826B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018507235A5 (enExample) | ||
| RU2396269C2 (ru) | Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpt1) | |
| RU2457207C2 (ru) | Активаторы глюкокиназы | |
| HRP20231310T1 (hr) | Heteroarilaminopirimidin amidni inhibitori autofagije i postupci njihove primjene | |
| JP5864589B2 (ja) | 細菌トポイソメラーゼｉｉ阻害性２−エチルカルバモイルアミノ−１，３−ベンゾチアゾール−５−イル類 | |
| US20120101100A1 (en) | Heterocyclic urea derivatives and methods of use thereof-211 | |
| KR101949624B1 (ko) | Tank-결합 키나제 억제제 화합물로서 유용한 아미노트리아진 유도체 | |
| HRP20230244T1 (hr) | Derivati 3-(1-oksoizoindolin-2-il)piperidin-2,6-diona i njihova upotreba | |
| JP2016523911A5 (enExample) | ||
| JP2020530446A5 (enExample) | ||
| SI3177619T1 (en) | 2- (morpholin-4-yl) -1,7-naphthyridines | |
| TWI628174B (zh) | 新穎吡啶衍生物 | |
| JP2015510938A5 (enExample) | ||
| JP2015522002A5 (enExample) | ||
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| JP2014525448A5 (enExample) | ||
| JP2017530960A5 (enExample) | ||
| JPWO2020231808A5 (enExample) | ||
| WO2005121110A1 (en) | Hetroaryl benzamide derivatives for use as glk activators in the treatment of diabetes | |
| WO2016046530A1 (en) | Novel compounds | |
| RU2010137300A (ru) | Модуляторы бета-амилоида | |
| JP2008513500A5 (enExample) | ||
| JP2018530591A5 (enExample) | ||
| JP2016500073A5 (enExample) | ||
| JP2011503194A5 (enExample) |