JP2018507235A5 - - Google Patents
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- 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- Withdrawn
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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
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- 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
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- 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
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- 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
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- 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
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| PCT/US2016/020802 WO2016141258A1 (en) | 2015-03-04 | 2016-03-04 | Sterol regulatory element-binding proteins (srebps) inhibitors |
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| US10328064B2 (en) | 2014-12-23 | 2019-06-25 | Fgh Biotech, Inc. | Compositions of fatostatin based heterocyclic compounds and uses thereof |
| JP2018507234A (ja) | 2015-03-04 | 2018-03-15 | メディベイション テクノロジーズ エルエルシー | 肝臓線維症、コレステロールの上昇およびインスリン抵抗性を処置する際における使用のためのｓｒｅｂｐ遮断薬 |
| CN109476635B (zh) | 2016-04-29 | 2021-07-13 | Fgh生物科技公司 | 用于治疗疾病的二取代吡唑类化合物 |
| AU2017323521B9 (en) | 2016-09-07 | 2022-02-17 | Fgh Biotech, Inc. | Di-substituted pyrazole compounds for the treatment of diseases |
| WO2019148125A1 (en) * | 2018-01-29 | 2019-08-01 | Capulus Therapeutics, Llc | Srebp inhibitors comprising a 6-membered central ring |
| 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 |
| CA3127828A1 (en) * | 2019-01-28 | 2020-08-06 | Capulus Therapeutics, Llc | Srebp inhibitors comprising a thiophene central ring |
| WO2021097122A1 (en) * | 2019-11-13 | 2021-05-20 | Capulus Therapeutics, Llc | Srebp inhibitor comprising a thiophene central ring |
| WO2021097123A1 (en) * | 2019-11-13 | 2021-05-20 | Capulus Therapeutics, Llc | Thiophene compounds with cyclic amides, and uses thereof |
| EP4096659A4 (en) * | 2020-01-27 | 2023-10-18 | Capulus Therapeutics, LLC | SREBP INHIBITORS COMPRISING A THIOPHENIC RING |
| WO2022020738A1 (en) * | 2020-07-24 | 2022-01-27 | 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 |
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| IL96891A0 (en) * | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| EP1054886B1 (en) | 1998-02-09 | 2002-09-04 | 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 |
| CZ20022100A3 (cs) | 1999-12-16 | 2002-09-11 | Schering Corporation | Substituované imidazolové deriváty a farmaceutický prostředek |
| 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 |
| US7244739B2 (en) | 2003-05-14 | 2007-07-17 | Torreypines Therapeutics, Inc. | Compounds and uses thereof in modulating amyloid beta |
| WO2006131336A1 (en) | 2005-06-08 | 2006-12-14 | Novartis Ag | POLYCYCLIC OXADIAZOLES OR I SOXAZOLES AND THEIR USE AS SlP RECEPTOR LIGANDS |
| EP1890547A2 (en) | 2005-06-09 | 2008-02-27 | Schering-Plough Ltd. | Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
| US8168793B2 (en) | 2005-07-26 | 2012-05-01 | Portela & Ca., S.A. | Nitrocatechol derivatives as COMT inhibitors |
| WO2007021941A2 (en) | 2005-08-16 | 2007-02-22 | Icagen, Inc. | Inhibitors of voltage-gated sodium channels |
| US8229106B2 (en) | 2007-01-22 | 2012-07-24 | D.S.P. Group, Ltd. | Apparatus and methods for enhancement of speech |
| CA2677264C (en) | 2007-02-02 | 2021-11-30 | 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 |
| SI2125797T1 (sl) * | 2007-03-16 | 2014-03-31 | Actelion Pharmaceuticals Ltd. | Derivati amino-piridina kot agonisti receptorja s1p1/edg1 |
| JP5451633B2 (ja) * | 2007-12-21 | 2014-03-26 | メルク セローノ ソシエテ アノニム | トリアゾールオキサジアゾール誘導体 |
| 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 |
| JP2016529224A (ja) | 2013-06-26 | 2016-09-23 | レット シンドローム リサーチ トラスト， インコーポレイテッド | レット症候群およびその処置 |
| CN106029072A (zh) | 2013-08-28 | 2016-10-12 | 麦迪韦逊技术股份有限公司 | 杂环化合物和使用方法 |
| JP2018507234A (ja) | 2015-03-04 | 2018-03-15 | メディベイション テクノロジーズ エルエルシー | 肝臓線維症、コレステロールの上昇およびインスリン抵抗性を処置する際における使用のためのｓｒｅｂｐ遮断薬 |
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2016
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- 2016-03-04 JP JP2017546186A patent/JP2018507235A/ja not_active Withdrawn
- 2016-03-04 EP EP16710893.5A patent/EP3265457A1/en not_active Withdrawn
- 2016-03-04 CA CA2977539A patent/CA2977539A1/en not_active Abandoned
- 2016-03-04 US US15/553,622 patent/US10189826B2/en not_active Expired - Fee Related
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