CA2728046A1 - S1p1 receptor agonists and use thereof - Google Patents

Info

Publication number

CA2728046A1

CA2728046A1 CA2728046A CA2728046A CA2728046A1 CA 2728046 A1 CA2728046 A1 CA 2728046A1 CA 2728046 A CA2728046 A CA 2728046A CA 2728046 A CA2728046 A CA 2728046A CA 2728046 A1 CA2728046 A1 CA 2728046A1

Authority

CA

Canada

Prior art keywords

fluoro

phenyl

thiazolo

phenylcyclopropyl

pyridin

Prior art date

2008-06-20

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 title claims abstract description 11
• 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 title claims abstract description 11
• 229940044601 receptor agonist Drugs 0.000 title abstract description 6
• 239000000018 receptor agonist Substances 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 187
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 201000010099 disease Diseases 0.000 claims abstract description 10
• -1 monosubstituted amino Chemical group 0.000 claims description 314
• 201000006417 multiple sclerosis Diseases 0.000 claims description 181
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 103
• 229910052731 fluorine Inorganic materials 0.000 claims description 69
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
• 229920006395 saturated elastomer Polymers 0.000 claims description 64
• 229910052801 chlorine Inorganic materials 0.000 claims description 62
• 238000000034 method Methods 0.000 claims description 62
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 125000001153 fluoro group Chemical group F* 0.000 claims description 40
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 34
• 239000003814 drug Substances 0.000 claims description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 27
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 26
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 24
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• 125000002837 carbocyclic group Chemical group 0.000 claims description 10
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 125000004476 heterocycloamino group Chemical group 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 230000001404 mediated effect Effects 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000004442 acylamino group Chemical group 0.000 claims description 6
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• NQOYFWVJUAMDSC-UHFFFAOYSA-N 1-[[2-methyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC1=CC(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)=CC=C1CN1CC(C(O)=O)C1 NQOYFWVJUAMDSC-UHFFFAOYSA-N 0.000 claims description 5
• KCMALGDZUKTGJR-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 KCMALGDZUKTGJR-UHFFFAOYSA-N 0.000 claims description 5
• RSJXHKBDHLDTJG-UHFFFAOYSA-N 1-[[3-methyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(C)=CC=1CN1CC(C(O)=O)C1 RSJXHKBDHLDTJG-UHFFFAOYSA-N 0.000 claims description 5
• OSOQQWGQWAAXRR-UHFFFAOYSA-N 3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]cyclobutane-1,1-dicarboxylic acid Chemical compound C1C(C(=O)O)(C(O)=O)CC1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 OSOQQWGQWAAXRR-UHFFFAOYSA-N 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• IXHZVOWTEVMNQD-UHFFFAOYSA-N 1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]cyclopropan-1-amine Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(F)=CC=1C1(N)CC1 IXHZVOWTEVMNQD-UHFFFAOYSA-N 0.000 claims description 4
• OIQUGXZGFRNXRR-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclohexyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CCCCC3)C=3C=CC=CC=3)N=C2S1 OIQUGXZGFRNXRR-UHFFFAOYSA-N 0.000 claims description 4
• LWFNPYNEZMTEHO-UHFFFAOYSA-N 2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propan-2-amine Chemical compound FC1=CC(C(C)(N)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 LWFNPYNEZMTEHO-UHFFFAOYSA-N 0.000 claims description 4
• NZOPMUNLWDQQBS-UHFFFAOYSA-N 2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]propane-1,3-diol Chemical compound FC1=CC(CC(CO)CO)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 NZOPMUNLWDQQBS-UHFFFAOYSA-N 0.000 claims description 4
• RSJARRDGCGLARB-UHFFFAOYSA-N [3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methanol Chemical compound FC1=CC(CO)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 RSJARRDGCGLARB-UHFFFAOYSA-N 0.000 claims description 4
• 125000002431 aminoalkoxy group Chemical group 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• OHDAURMSEHMPFJ-IBGZPJMESA-N (1s)-2,2,2-trifluoro-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethanol Chemical compound FC1=CC([C@H](O)C(F)(F)F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 OHDAURMSEHMPFJ-IBGZPJMESA-N 0.000 claims description 3
• JJMNOHMYOCDTNE-UHFFFAOYSA-N 1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethanol Chemical compound FC1=CC(C(O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 JJMNOHMYOCDTNE-UHFFFAOYSA-N 0.000 claims description 3
• DGRKENUAODQPTI-UHFFFAOYSA-N 1-[[3-amino-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(N)=CC=1CN1CC(C(O)=O)C1 DGRKENUAODQPTI-UHFFFAOYSA-N 0.000 claims description 3
• OIIKLYFYHWVBBT-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopent-3-en-1-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC=CC3)C=3C=CC=CC=3)N=C2S1 OIIKLYFYHWVBBT-UHFFFAOYSA-N 0.000 claims description 3
• XOISWOAQHPFMSU-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopentyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CCCC3)C=3C=CC=CC=3)N=C2S1 XOISWOAQHPFMSU-UHFFFAOYSA-N 0.000 claims description 3
• SJRVYCQTDNRXSQ-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidin-3-ol Chemical compound C1C(O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 SJRVYCQTDNRXSQ-UHFFFAOYSA-N 0.000 claims description 3
• QFXSDFZFPKZDSK-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(2-phenyloxetan-2-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(OCC3)C=3C=CC=CC=3)N=C2S1 QFXSDFZFPKZDSK-UHFFFAOYSA-N 0.000 claims description 3
• WYDTUIYHKYBKDQ-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-[1-(4-fluorophenyl)cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC(F)=CC=3)N=C2S1 WYDTUIYHKYBKDQ-UHFFFAOYSA-N 0.000 claims description 3
• UMQXIFJBTRLNCD-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-[1-(4-hydroxyphenyl)cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC(O)=CC=3)N=C2S1 UMQXIFJBTRLNCD-UHFFFAOYSA-N 0.000 claims description 3
• ASUCRXBDHDVRQF-UHFFFAOYSA-N 2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]amino]acetic acid Chemical compound FC1=CC(C(=O)NCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 ASUCRXBDHDVRQF-UHFFFAOYSA-N 0.000 claims description 3
• FQYFGWGKFYQDOL-UHFFFAOYSA-N 3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propanoic acid Chemical compound FC1=CC(CCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 FQYFGWGKFYQDOL-UHFFFAOYSA-N 0.000 claims description 3
• LQFBUKSMYSXBTE-UHFFFAOYSA-N 3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]amino]propanoic acid Chemical compound FC1=CC(C(=O)NCCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 LQFBUKSMYSXBTE-UHFFFAOYSA-N 0.000 claims description 3
• CPZNHEBXQUGQPL-UHFFFAOYSA-N 4-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]amino]butanoic acid Chemical compound FC1=CC(C(=O)NCCCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 CPZNHEBXQUGQPL-UHFFFAOYSA-N 0.000 claims description 3
• CFJDEAYMRZMDGQ-IYARVYRRSA-N C1[C@@H](C(=O)O)C[C@@H]1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 Chemical compound C1[C@@H](C(=O)O)C[C@@H]1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 CFJDEAYMRZMDGQ-IYARVYRRSA-N 0.000 claims description 3
• CFJDEAYMRZMDGQ-HDICACEKSA-N C1[C@H](C(=O)O)C[C@@H]1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 Chemical compound C1[C@H](C(=O)O)C[C@@H]1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 CFJDEAYMRZMDGQ-HDICACEKSA-N 0.000 claims description 3
• BSFNCTKLBHOCNB-UHFFFAOYSA-N [2-amino-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]-2-(hydroxymethyl)butyl] dihydrogen phosphate Chemical compound FC1=CC(CCC(CO)(N)COP(O)(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 BSFNCTKLBHOCNB-UHFFFAOYSA-N 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• KVSCIJUANFKDHN-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclobutyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CCC3)C=3C=CC=CC=3)N=C2S1 KVSCIJUANFKDHN-UHFFFAOYSA-N 0.000 claims description 2
• XQLGIFYJCJXYBJ-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-[1-(2-fluorophenyl)cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C(=CC=CC=3)F)N=C2S1 XQLGIFYJCJXYBJ-UHFFFAOYSA-N 0.000 claims description 2
• QILOXDHVYSGPRP-UHFFFAOYSA-N 1-[[3-fluoro-4-[6-(1-phenylcyclopropyl)-[1,3]thiazolo[4,5-c]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CN=C(C3(CC3)C=3C=CC=CC=3)C=C2S1 QILOXDHVYSGPRP-UHFFFAOYSA-N 0.000 claims description 2
• SINCOKVLJHSFIM-INIZCTEOSA-N 1-[[4-[5-[1-[(1s)-3,3-difluorocyclopentyl]cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)[C@@H]3CC(F)(F)CC3)N=C2S1 SINCOKVLJHSFIM-INIZCTEOSA-N 0.000 claims description 2
• ZKOGVNKSMKCWIJ-UHFFFAOYSA-N 2-[4-[(3,3-difluoroazetidin-1-yl)methyl]-2-fluorophenyl]-5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridine Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(F)=CC=1CN1CC(F)(F)C1 ZKOGVNKSMKCWIJ-UHFFFAOYSA-N 0.000 claims description 2
• YBBIQAQUTJCVHA-UHFFFAOYSA-N 3-[2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propan-2-ylamino]propanoic acid Chemical compound FC1=CC(C(C)(NCCC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 YBBIQAQUTJCVHA-UHFFFAOYSA-N 0.000 claims description 2
• LAXZWYOIVOOUDB-UHFFFAOYSA-N 3-[[1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]cyclopropyl]amino]propanoic acid Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(F)=CC=1C1(NCCC(=O)O)CC1 LAXZWYOIVOOUDB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 2
• CIFFBENAZAIHLL-UHFFFAOYSA-N [2,6-dimethyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methanol Chemical compound CC1=C(CO)C(C)=CC(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)=C1 CIFFBENAZAIHLL-UHFFFAOYSA-N 0.000 claims description 2
• DLKFRHULCKAHOW-UHFFFAOYSA-N [2-methyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methanol Chemical compound C1=C(CO)C(C)=CC(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)=C1 DLKFRHULCKAHOW-UHFFFAOYSA-N 0.000 claims description 2
• VTWSHDBNPHFDGO-VWLOTQADSA-N (2s)-2-amino-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]-2-methylbutanoic acid Chemical compound FC1=CC(CC[C@@](N)(C)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 VTWSHDBNPHFDGO-VWLOTQADSA-N 0.000 claims 2
• HIVYIHLBVHGTEB-UHFFFAOYSA-N 2-[4-(azetidin-1-ylmethyl)-2-fluorophenyl]-5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridine Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(F)=CC=1CN1CCC1 HIVYIHLBVHGTEB-UHFFFAOYSA-N 0.000 claims 2
• UWAASNKMOLMYQX-UHFFFAOYSA-N 3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]cyclobutane-1-carboxylic acid Chemical compound C1C(C(=O)O)CC1NC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 UWAASNKMOLMYQX-UHFFFAOYSA-N 0.000 claims 2
• HPLPYWLCVPJOBA-CQSZACIVSA-N (1r)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethanamine Chemical compound FC1=CC([C@H](N)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 HPLPYWLCVPJOBA-CQSZACIVSA-N 0.000 claims 1
• HPLPYWLCVPJOBA-AWEZNQCLSA-N (1s)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethanamine Chemical compound FC1=CC([C@@H](N)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 HPLPYWLCVPJOBA-AWEZNQCLSA-N 0.000 claims 1
• ICAUQGOTJWRMLA-OAQYLSRUSA-N (2r)-1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 ICAUQGOTJWRMLA-OAQYLSRUSA-N 0.000 claims 1
• LGXUOJNGDSKUJR-JOCHJYFZSA-N (2r)-1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 LGXUOJNGDSKUJR-JOCHJYFZSA-N 0.000 claims 1
• GRHYDNFYDMAIFI-OAHLLOKOSA-N (2r)-2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methylamino]propanoic acid Chemical compound FC1=CC(CN[C@H](C)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 GRHYDNFYDMAIFI-OAHLLOKOSA-N 0.000 claims 1
• KMCSQCGFOWMHTE-GOSISDBHSA-N (2r)-2-amino-3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propanoic acid Chemical compound FC1=CC(C[C@@H](N)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 KMCSQCGFOWMHTE-GOSISDBHSA-N 0.000 claims 1
• VTWSHDBNPHFDGO-RUZDIDTESA-N (2r)-2-amino-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]-2-methylbutanoic acid Chemical compound FC1=CC(CC[C@](N)(C)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 VTWSHDBNPHFDGO-RUZDIDTESA-N 0.000 claims 1
• MLIPKGLXHUBXKK-LJQANCHMSA-N (2r)-2-amino-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]butanoic acid Chemical compound FC1=CC(CC[C@@H](N)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 MLIPKGLXHUBXKK-LJQANCHMSA-N 0.000 claims 1
• UOGFSBHCCGELLP-HXUWFJFHSA-N (2r)-3-[2,6-dimethyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenoxy]propane-1,2-diol Chemical compound CC1=C(OC[C@H](O)CO)C(C)=CC(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)=C1 UOGFSBHCCGELLP-HXUWFJFHSA-N 0.000 claims 1
• MRLPAUFHYFKZPJ-LJQANCHMSA-N (2r)-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]-2-hydroxy-4-oxobutanoic acid Chemical compound FC1=CC(NC(=O)C[C@@H](O)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 MRLPAUFHYFKZPJ-LJQANCHMSA-N 0.000 claims 1
• GXOKDJQBRJNTEG-LJQANCHMSA-N (2r)-4-amino-2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]-4-oxobutanoic acid Chemical compound FC1=CC(N[C@H](CC(=O)N)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 GXOKDJQBRJNTEG-LJQANCHMSA-N 0.000 claims 1
• MQWWGSOFGNLKML-HRAATJIYSA-N (2r,4r)-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@@H](C(=O)O)C[C@@H]1C(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 MQWWGSOFGNLKML-HRAATJIYSA-N 0.000 claims 1
• ICAUQGOTJWRMLA-NRFANRHFSA-N (2s)-1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 ICAUQGOTJWRMLA-NRFANRHFSA-N 0.000 claims 1
• LGXUOJNGDSKUJR-QFIPXVFZSA-N (2s)-1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 LGXUOJNGDSKUJR-QFIPXVFZSA-N 0.000 claims 1
• GRHYDNFYDMAIFI-HNNXBMFYSA-N (2s)-2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methylamino]propanoic acid Chemical compound FC1=CC(CN[C@@H](C)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 GRHYDNFYDMAIFI-HNNXBMFYSA-N 0.000 claims 1
• KMCSQCGFOWMHTE-SFHVURJKSA-N (2s)-2-amino-3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propanoic acid Chemical compound FC1=CC(C[C@H](N)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 KMCSQCGFOWMHTE-SFHVURJKSA-N 0.000 claims 1
• MLIPKGLXHUBXKK-IBGZPJMESA-N (2s)-2-amino-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]butanoic acid Chemical compound FC1=CC(CC[C@H](N)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 MLIPKGLXHUBXKK-IBGZPJMESA-N 0.000 claims 1
• UOGFSBHCCGELLP-FQEVSTJZSA-N (2s)-3-[2,6-dimethyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenoxy]propane-1,2-diol Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)=C1 UOGFSBHCCGELLP-FQEVSTJZSA-N 0.000 claims 1
• MRLPAUFHYFKZPJ-IBGZPJMESA-N (2s)-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]-2-hydroxy-4-oxobutanoic acid Chemical compound FC1=CC(NC(=O)C[C@H](O)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 MRLPAUFHYFKZPJ-IBGZPJMESA-N 0.000 claims 1
• DCWJFNAOUTVMRH-JTSKRJEESA-N (2s,4r)-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]-1-methylpyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C)C[C@H]1C(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 DCWJFNAOUTVMRH-JTSKRJEESA-N 0.000 claims 1
• WTALFFUKIPKJQW-FNZWTVRRSA-N (2s,4r)-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]-4-hydroxypyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@]1(O)C(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 WTALFFUKIPKJQW-FNZWTVRRSA-N 0.000 claims 1
• MQWWGSOFGNLKML-KKSFZXQISA-N (2s,4r)-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1C(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 MQWWGSOFGNLKML-KKSFZXQISA-N 0.000 claims 1
• OZWBUQJQIFWHIH-CTNGQTDRSA-N (2s,4r)-4-[4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenoxy]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@H]1OC1=CC=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C=C1 OZWBUQJQIFWHIH-CTNGQTDRSA-N 0.000 claims 1
• AHKKYONYGWYRAR-GOSISDBHSA-N (3r)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1C(=O)C(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 AHKKYONYGWYRAR-GOSISDBHSA-N 0.000 claims 1
• DFKVJJCSINDUMY-GOSISDBHSA-N (3r)-1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 DFKVJJCSINDUMY-GOSISDBHSA-N 0.000 claims 1
• YSSZJWNEWXHKEG-IAGOWNOFSA-N (3r)-3-[[(1r)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]amino]butanoic acid Chemical compound FC1=CC([C@@H](C)N[C@@H](CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 YSSZJWNEWXHKEG-IAGOWNOFSA-N 0.000 claims 1
• YSSZJWNEWXHKEG-SJORKVTESA-N (3r)-3-[[(1s)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]amino]butanoic acid Chemical compound FC1=CC([C@H](C)N[C@@H](CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 YSSZJWNEWXHKEG-SJORKVTESA-N 0.000 claims 1
• ZQJUTZAZNIRVCT-MRXNPFEDSA-N (3r)-3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methylamino]butanoic acid Chemical compound FC1=CC(CN[C@@H](CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 ZQJUTZAZNIRVCT-MRXNPFEDSA-N 0.000 claims 1
• IOBHKOYYARRWQM-LJQANCHMSA-N (3r)-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]-3-hydroxy-4-oxobutanoic acid Chemical compound FC1=CC(NC(=O)[C@@H](CC(O)=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 IOBHKOYYARRWQM-LJQANCHMSA-N 0.000 claims 1
• XQPSZKTXVQXRPT-LJQANCHMSA-N (3r)-4-amino-3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]-4-oxobutanoic acid Chemical compound FC1=CC(N[C@H](CC(O)=O)C(=O)N)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 XQPSZKTXVQXRPT-LJQANCHMSA-N 0.000 claims 1
• DFKVJJCSINDUMY-SFHVURJKSA-N (3s)-1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C1[C@@H](C(=O)O)CCN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 DFKVJJCSINDUMY-SFHVURJKSA-N 0.000 claims 1
• YSSZJWNEWXHKEG-DLBZAZTESA-N (3s)-3-[[(1r)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]amino]butanoic acid Chemical compound FC1=CC([C@@H](C)N[C@H](CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 YSSZJWNEWXHKEG-DLBZAZTESA-N 0.000 claims 1
• YSSZJWNEWXHKEG-IRXDYDNUSA-N (3s)-3-[[(1s)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]amino]butanoic acid Chemical compound FC1=CC([C@H](C)N[C@H](CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 YSSZJWNEWXHKEG-IRXDYDNUSA-N 0.000 claims 1
• ZQJUTZAZNIRVCT-INIZCTEOSA-N (3s)-3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methylamino]butanoic acid Chemical compound FC1=CC(CN[C@H](CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 ZQJUTZAZNIRVCT-INIZCTEOSA-N 0.000 claims 1
• IOBHKOYYARRWQM-IBGZPJMESA-N (3s)-4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]-3-hydroxy-4-oxobutanoic acid Chemical compound FC1=CC(NC(=O)[C@H](CC(O)=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 IOBHKOYYARRWQM-IBGZPJMESA-N 0.000 claims 1
• ICEIWTRKSBHUPU-MRXNPFEDSA-N 1-[(1r)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]azetidine-3-carboxylic acid Chemical compound N1([C@H](C)C=2C=C(F)C(C=3SC4=NC(=CC=C4N=3)C3(CC3)C=3C=CC=CC=3)=CC=2)CC(C(O)=O)C1 ICEIWTRKSBHUPU-MRXNPFEDSA-N 0.000 claims 1
• OIJNAPDLOBVOOP-HSZRJFAPSA-N 1-[(1r)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propyl]azetidine-3-carboxylic acid Chemical compound N1([C@H](CC)C=2C=C(F)C(C=3SC4=NC(=CC=C4N=3)C3(CC3)C=3C=CC=CC=3)=CC=2)CC(C(O)=O)C1 OIJNAPDLOBVOOP-HSZRJFAPSA-N 0.000 claims 1
• OIJNAPDLOBVOOP-QHCPKHFHSA-N 1-[(1s)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propyl]azetidine-3-carboxylic acid Chemical compound N1([C@@H](CC)C=2C=C(F)C(C=3SC4=NC(=CC=C4N=3)C3(CC3)C=3C=CC=CC=3)=CC=2)CC(C(O)=O)C1 OIJNAPDLOBVOOP-QHCPKHFHSA-N 0.000 claims 1
• SVWVJTMZSXNCRO-UHFFFAOYSA-N 1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1C(=O)C(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 SVWVJTMZSXNCRO-UHFFFAOYSA-N 0.000 claims 1
• QFDOYUSEQNYASA-UHFFFAOYSA-N 1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]-n-methylcyclopropan-1-amine Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(F)=CC=1C1(NC)CC1 QFDOYUSEQNYASA-UHFFFAOYSA-N 0.000 claims 1
• HZXGZVRQQFGNFN-UHFFFAOYSA-N 1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]pyrrolidin-2-one Chemical compound FC1=CC(N2C(CCC2)=O)=CC=C1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 HZXGZVRQQFGNFN-UHFFFAOYSA-N 0.000 claims 1
• KBRHOHMPEPDZJP-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]-3-hydroxyazetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)(O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 KBRHOHMPEPDZJP-UHFFFAOYSA-N 0.000 claims 1
• SQPRETQQWKXEPW-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]imidazole-4-carboxylic acid Chemical compound C1=NC(C(=O)O)=CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 SQPRETQQWKXEPW-UHFFFAOYSA-N 0.000 claims 1
• FQXZWIMLHPSJLU-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]pyrazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)C=CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 FQXZWIMLHPSJLU-UHFFFAOYSA-N 0.000 claims 1
• UWFKJTCRWCNSNI-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 UWFKJTCRWCNSNI-UHFFFAOYSA-N 0.000 claims 1
• KBVMVPHQZLQHLY-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methylamino]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(F)=CC=1CNC1(C(=O)O)CC1 KBVMVPHQZLQHLY-UHFFFAOYSA-N 0.000 claims 1
• GSAKNCGWXFHNQA-UHFFFAOYSA-N 1-[[3-fluoro-4-[5-[1-(oxan-4-yl)cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C3CCOCC3)N=C2S1 GSAKNCGWXFHNQA-UHFFFAOYSA-N 0.000 claims 1
• RWWBUTGMPHDFGX-UHFFFAOYSA-N 1-[[3-fluoro-4-[6-(1-phenylcyclopropyl)-1,3-benzothiazol-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)C=C2S1 RWWBUTGMPHDFGX-UHFFFAOYSA-N 0.000 claims 1
• YAEJSOIIAJFYAA-UHFFFAOYSA-N 1-[[3-fluoro-4-[6-(1-pyridin-2-ylcyclopropyl)-1,3-benzothiazol-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3N=CC=CC=3)C=C2S1 YAEJSOIIAJFYAA-UHFFFAOYSA-N 0.000 claims 1
• XYKIBXCLJSGSTN-UHFFFAOYSA-N 1-[[4-[5-(1-cyclobutylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C3CCC3)N=C2S1 XYKIBXCLJSGSTN-UHFFFAOYSA-N 0.000 claims 1
• NPBBLNMDGIUANQ-UHFFFAOYSA-N 1-[[4-[5-(1-cyclohexylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C3CCCCC3)N=C2S1 NPBBLNMDGIUANQ-UHFFFAOYSA-N 0.000 claims 1
• ADZPKNJWYUCPPK-UHFFFAOYSA-N 1-[[4-[5-(1-cyclopentylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C3CCCC3)N=C2S1 ADZPKNJWYUCPPK-UHFFFAOYSA-N 0.000 claims 1
• RLARDFHOEZWBLI-UHFFFAOYSA-N 1-[[4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C=C1 RLARDFHOEZWBLI-UHFFFAOYSA-N 0.000 claims 1
• NJDMSHLMXQGQPH-UHFFFAOYSA-N 1-[[4-[5-[1-(3,3-difluorocyclobutyl)cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C3CC(F)(F)C3)N=C2S1 NJDMSHLMXQGQPH-UHFFFAOYSA-N 0.000 claims 1
• WNJZDTVKMZYSDS-UHFFFAOYSA-N 1-[[4-[5-[1-(4,4-difluorocyclohexyl)cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C3CCC(F)(F)CC3)N=C2S1 WNJZDTVKMZYSDS-UHFFFAOYSA-N 0.000 claims 1
• SINCOKVLJHSFIM-MRXNPFEDSA-N 1-[[4-[5-[1-[(1r)-3,3-difluorocyclopentyl]cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)[C@H]3CC(F)(F)CC3)N=C2S1 SINCOKVLJHSFIM-MRXNPFEDSA-N 0.000 claims 1
• HMZVKDYDGFUGHL-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]acetamide Chemical compound FC1=CC(NC(=O)C(F)(F)F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 HMZVKDYDGFUGHL-UHFFFAOYSA-N 0.000 claims 1
• DCTBWKCMHAXEPQ-UHFFFAOYSA-N 2-(1h-indol-5-yl)-5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridine Chemical compound C1CC1(C=1N=C2SC(=NC2=CC=1)C=1C=C2C=CNC2=CC=1)C1=CC=CC=C1 DCTBWKCMHAXEPQ-UHFFFAOYSA-N 0.000 claims 1
• CEGSARAHLLYTNN-UHFFFAOYSA-N 2-(3h-benzimidazol-5-yl)-5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridine Chemical compound C1CC1(C=1N=C2SC(=NC2=CC=1)C=1C=C2N=CNC2=CC=1)C1=CC=CC=C1 CEGSARAHLLYTNN-UHFFFAOYSA-N 0.000 claims 1
• GTTMJUHHNGKUHO-UHFFFAOYSA-N 2-[1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidin-3-yl]acetic acid Chemical compound C1C(CC(=O)O)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 GTTMJUHHNGKUHO-UHFFFAOYSA-N 0.000 claims 1
• ZZJXFUOCCZJZIB-UHFFFAOYSA-N 2-[2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethylamino]-2-oxoacetic acid Chemical compound FC1=CC(CCNC(=O)C(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 ZZJXFUOCCZJZIB-UHFFFAOYSA-N 0.000 claims 1
• VORCSLWLKKFQHC-UHFFFAOYSA-N 2-[2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethylamino]acetic acid Chemical compound FC1=CC(CCNCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 VORCSLWLKKFQHC-UHFFFAOYSA-N 0.000 claims 1
• SXWDUKRKCWUMIC-UHFFFAOYSA-N 2-[2-fluoro-4-[(3-fluoroazetidin-1-yl)methyl]phenyl]-5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridine Chemical compound C1C(F)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 SXWDUKRKCWUMIC-UHFFFAOYSA-N 0.000 claims 1
• CAEJYNFXMQCXEC-UHFFFAOYSA-N 2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]-n,n-dimethylethanamine Chemical compound FC1=CC(CCN(C)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 CAEJYNFXMQCXEC-UHFFFAOYSA-N 0.000 claims 1
• ZDARLJLQSUPMHM-UHFFFAOYSA-N 2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethanamine Chemical compound FC1=CC(CCN)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 ZDARLJLQSUPMHM-UHFFFAOYSA-N 0.000 claims 1
• AJPDBWBLDLBHFP-UHFFFAOYSA-N 2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethanol Chemical compound FC1=CC(CCO)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 AJPDBWBLDLBHFP-UHFFFAOYSA-N 0.000 claims 1
• SMRWUURWIUGKDT-UHFFFAOYSA-N 2-[4-(azetidin-1-ylmethyl)-3,5-dimethylphenyl]-5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridine Chemical compound CC1=CC(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)=CC(C)=C1CN1CCC1 SMRWUURWIUGKDT-UHFFFAOYSA-N 0.000 claims 1
• YEPAMKWOYZLGNG-UHFFFAOYSA-N 2-[5-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]-1,3-dihydroisoindol-2-yl]acetic acid Chemical compound C1=C2CN(CC(=O)O)CC2=CC=C1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 YEPAMKWOYZLGNG-UHFFFAOYSA-N 0.000 claims 1
• WBCIJRRSDSFXLA-UHFFFAOYSA-N 2-[5-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]indol-1-yl]acetic acid Chemical compound C=1C=C2N(CC(=O)O)C=CC2=CC=1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 WBCIJRRSDSFXLA-UHFFFAOYSA-N 0.000 claims 1
• YLQKFWVHNGZHGG-UHFFFAOYSA-N 2-[6-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3,4-dihydro-1h-isoquinolin-2-yl]acetic acid Chemical compound C=1C=C2CN(CC(=O)O)CCC2=CC=1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 YLQKFWVHNGZHGG-UHFFFAOYSA-N 0.000 claims 1
• RMFNOJPTVRZKER-UHFFFAOYSA-N 2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methoxy]acetic acid Chemical compound FC1=CC(COCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 RMFNOJPTVRZKER-UHFFFAOYSA-N 0.000 claims 1
• HUOCVQORDNRUEB-UHFFFAOYSA-N 2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC=NN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 HUOCVQORDNRUEB-UHFFFAOYSA-N 0.000 claims 1
• REZUCMPLONFXFD-UHFFFAOYSA-N 2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methylamino]-2-methylpropanoic acid Chemical compound FC1=CC(CNC(C)(C)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 REZUCMPLONFXFD-UHFFFAOYSA-N 0.000 claims 1
• VENLOUUVGMBXRA-UHFFFAOYSA-N 2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methylamino]acetic acid Chemical compound FC1=CC(CNCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 VENLOUUVGMBXRA-UHFFFAOYSA-N 0.000 claims 1
• YUIKHXVWWXKXIN-UHFFFAOYSA-N 2-amino-2-[2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]propane-1,3-diol Chemical compound FC1=CC(CCC(CO)(CO)N)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 YUIKHXVWWXKXIN-UHFFFAOYSA-N 0.000 claims 1
• UFQKEEFNPMAHQH-UHFFFAOYSA-N 2-amino-3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propan-1-ol Chemical compound FC1=CC(CC(CO)N)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 UFQKEEFNPMAHQH-UHFFFAOYSA-N 0.000 claims 1
• KMCSQCGFOWMHTE-UHFFFAOYSA-N 2-amino-3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propanoic acid Chemical compound FC1=CC(CC(N)C(O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 KMCSQCGFOWMHTE-UHFFFAOYSA-N 0.000 claims 1
• YSSZJWNEWXHKEG-UHFFFAOYSA-N 3-[1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethylamino]butanoic acid Chemical compound FC1=CC(C(C)NC(CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 YSSZJWNEWXHKEG-UHFFFAOYSA-N 0.000 claims 1
• NMSLMMIQACOIGQ-UHFFFAOYSA-N 3-[1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethylamino]propanoic acid Chemical compound FC1=CC(C(NCCC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 NMSLMMIQACOIGQ-UHFFFAOYSA-N 0.000 claims 1
• OGKHLOKWFGATCA-UHFFFAOYSA-N 3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]propanoic acid Chemical compound FC1=CC(NCCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 OGKHLOKWFGATCA-UHFFFAOYSA-N 0.000 claims 1
• MLRJRUKHPPYMSX-UHFFFAOYSA-N 3-[3-fluoro-n-methyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]propanoic acid Chemical compound FC1=CC(N(CCC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 MLRJRUKHPPYMSX-UHFFFAOYSA-N 0.000 claims 1
• JJKYWTRVADBCKT-UHFFFAOYSA-N 3-[4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]propanoic acid Chemical compound C1=CC(NCCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 JJKYWTRVADBCKT-UHFFFAOYSA-N 0.000 claims 1
• JAFPEQCJDDRMHW-UHFFFAOYSA-N 3-[5-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]-1,3-dihydroisoindol-2-yl]propanoic acid Chemical compound C1=C2CN(CCC(=O)O)CC2=CC=C1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 JAFPEQCJDDRMHW-UHFFFAOYSA-N 0.000 claims 1
• KUPNRRBAHXLCPZ-UHFFFAOYSA-N 3-[5-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzimidazol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=NC2=CC=1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 KUPNRRBAHXLCPZ-UHFFFAOYSA-N 0.000 claims 1
• WWFLCFSSZJSBON-UHFFFAOYSA-N 3-[5-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=CC2=CC=1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 WWFLCFSSZJSBON-UHFFFAOYSA-N 0.000 claims 1
• JPLZHBMBMUPCAN-UHFFFAOYSA-N 3-[6-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]-3,4-dihydro-1h-isoquinolin-2-yl]propanoic acid Chemical compound C=1C=C2CN(CCC(=O)O)CCC2=CC=1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 JPLZHBMBMUPCAN-UHFFFAOYSA-N 0.000 claims 1
• BOUVVZYZJSJQLM-UHFFFAOYSA-N 3-[6-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzimidazol-1-yl]propanoic acid Chemical compound C1=C2N(CCC(=O)O)C=NC2=CC=C1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 BOUVVZYZJSJQLM-UHFFFAOYSA-N 0.000 claims 1
• NMSLMMIQACOIGQ-MRXNPFEDSA-N 3-[[(1r)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]amino]propanoic acid Chemical compound FC1=CC([C@H](NCCC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 NMSLMMIQACOIGQ-MRXNPFEDSA-N 0.000 claims 1
• NMSLMMIQACOIGQ-INIZCTEOSA-N 3-[[(1s)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]amino]propanoic acid Chemical compound FC1=CC([C@@H](NCCC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 NMSLMMIQACOIGQ-INIZCTEOSA-N 0.000 claims 1
• OOBALZZYTSAKCV-UHFFFAOYSA-N 3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]-methylamino]propanoic acid Chemical compound FC1=CC(C(=O)N(CCC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 OOBALZZYTSAKCV-UHFFFAOYSA-N 0.000 claims 1
• POSXCHANUIGYIM-UHFFFAOYSA-N 3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]amino]-3-methylbutanoic acid Chemical compound FC1=CC(C(=O)NC(C)(CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 POSXCHANUIGYIM-UHFFFAOYSA-N 0.000 claims 1
• NWNPYQKNBUPBID-UHFFFAOYSA-N 3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]amino]butanoic acid Chemical compound FC1=CC(C(=O)NC(CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 NWNPYQKNBUPBID-UHFFFAOYSA-N 0.000 claims 1
• HNVBIOZWSOINAN-UHFFFAOYSA-N 3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]imidazole-4-carboxylic acid Chemical compound OC(=O)C1=CN=CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 HNVBIOZWSOINAN-UHFFFAOYSA-N 0.000 claims 1
• ZQJUTZAZNIRVCT-UHFFFAOYSA-N 3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methylamino]butanoic acid Chemical compound FC1=CC(CNC(CC(O)=O)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 ZQJUTZAZNIRVCT-UHFFFAOYSA-N 0.000 claims 1
• BJWDQTKPJXMMLJ-UHFFFAOYSA-N 3-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]sulfamoyl]propanoic acid Chemical compound FC1=CC(NS(=O)(=O)CCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 BJWDQTKPJXMMLJ-UHFFFAOYSA-N 0.000 claims 1
• CUZSURWZXLOBBS-UHFFFAOYSA-N 3-fluoro-1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)(F)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 CUZSURWZXLOBBS-UHFFFAOYSA-N 0.000 claims 1
• JILFMCAHUIKLIO-UHFFFAOYSA-N 3-fluoro-n,n-dimethyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]aniline Chemical compound FC1=CC(N(C)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 JILFMCAHUIKLIO-UHFFFAOYSA-N 0.000 claims 1
• BLCXSRMPGZPVSR-UHFFFAOYSA-N 3-fluoro-n-(2-hydroxyethyl)-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzamide Chemical compound FC1=CC(C(=O)NCCO)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 BLCXSRMPGZPVSR-UHFFFAOYSA-N 0.000 claims 1
• IVKZRYKWMWLVFH-UHFFFAOYSA-N 3-fluoro-n-(2-hydroxyethyl)-n-methyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzamide Chemical compound FC1=CC(C(=O)N(CCO)C)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 IVKZRYKWMWLVFH-UHFFFAOYSA-N 0.000 claims 1
• JHYLQOKEUJNENW-UHFFFAOYSA-N 3-fluoro-n-(2-methoxyethyl)-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzamide Chemical compound FC1=CC(C(=O)NCCOC)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 JHYLQOKEUJNENW-UHFFFAOYSA-N 0.000 claims 1
• FSAIBDFYVQAJND-UHFFFAOYSA-N 3-fluoro-n-(2-methoxyethyl)-n-methyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzamide Chemical compound FC1=CC(C(=O)N(C)CCOC)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 FSAIBDFYVQAJND-UHFFFAOYSA-N 0.000 claims 1
• QWMWNHLXLLSOKR-UHFFFAOYSA-N 3-fluoro-n-methyl-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]aniline Chemical compound FC1=CC(NC)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 QWMWNHLXLLSOKR-UHFFFAOYSA-N 0.000 claims 1
• RNJUDXBXJHLETI-UHFFFAOYSA-N 4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]-4-oxobutanoic acid Chemical compound FC1=CC(NC(=O)CCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 RNJUDXBXJHLETI-UHFFFAOYSA-N 0.000 claims 1
• AKZSHTFFWDWNND-UHFFFAOYSA-N 4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]anilino]butanoic acid Chemical compound FC1=CC(NCCCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 AKZSHTFFWDWNND-UHFFFAOYSA-N 0.000 claims 1
• KOPIRZFQEIFTSN-UHFFFAOYSA-N 4-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]butanoic acid Chemical compound FC1=CC(CCCC(=O)O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 KOPIRZFQEIFTSN-UHFFFAOYSA-N 0.000 claims 1
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• 230000002441 reversible effect Effects 0.000 description 3
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• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• 239000005720 sucrose Substances 0.000 description 3
• 239000000829 suppository Substances 0.000 description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
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• 229910052723 transition metal Inorganic materials 0.000 description 3
• 150000003624 transition metals Chemical class 0.000 description 3
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• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
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• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
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• KVQHZVCCVFVUPN-XYOKQWHBSA-N methyl (e)-3-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]prop-2-enoate Chemical compound FC1=CC(/C=C/C(=O)OC)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 KVQHZVCCVFVUPN-XYOKQWHBSA-N 0.000 description 2
• HNZZITTWMKDWLC-KRWDZBQOSA-N methyl 1-[(1s)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1[C@@H](C)C(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 HNZZITTWMKDWLC-KRWDZBQOSA-N 0.000 description 2
• NYFQYNAAOOCLKO-DEOSSOPVSA-N methyl 1-[(1s)-1-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]propyl]azetidine-3-carboxylate Chemical compound N1([C@@H](CC)C=2C=C(F)C(C=3SC4=NC(=CC=C4N=3)C3(CC3)C=3C=CC=CC=3)=CC=2)CC(C(=O)OC)C1 NYFQYNAAOOCLKO-DEOSSOPVSA-N 0.000 description 2
• SPWYTFODRYKQLD-UHFFFAOYSA-N methyl 1-[[3-amino-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1N)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 SPWYTFODRYKQLD-UHFFFAOYSA-N 0.000 description 2
• BFQLYEROZJLIAA-UHFFFAOYSA-N methyl 1-[[3-fluoro-4-[5-(1-phenylcyclopent-3-en-1-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC=CC3)C=3C=CC=CC=3)N=C2S1 BFQLYEROZJLIAA-UHFFFAOYSA-N 0.000 description 2
• YMYBSVNTTZZLAF-UHFFFAOYSA-N methyl 1-[[3-fluoro-4-[5-(1-phenylcyclopentyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CCCC3)C=3C=CC=CC=3)N=C2S1 YMYBSVNTTZZLAF-UHFFFAOYSA-N 0.000 description 2
• HHLVTKLAEICMJX-UHFFFAOYSA-N methyl 1-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 HHLVTKLAEICMJX-UHFFFAOYSA-N 0.000 description 2
• MERIQYJDQQNIFT-UHFFFAOYSA-N methyl 1-[[3-fluoro-4-[5-[1-(2-fluorophenyl)cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C(=CC=CC=3)F)N=C2S1 MERIQYJDQQNIFT-UHFFFAOYSA-N 0.000 description 2
• YAVSPJDHNOTNNG-UHFFFAOYSA-N methyl 1-[[3-fluoro-4-[5-[1-(4-fluorophenyl)cyclopropyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC(F)=CC=3)N=C2S1 YAVSPJDHNOTNNG-UHFFFAOYSA-N 0.000 description 2
• XTKDKYQZUQNXEA-UHFFFAOYSA-N methyl 1-[[3-fluoro-4-[5-[1-(4-fluorophenyl)ethenyl]-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C(=C)C=3C=CC(F)=CC=3)N=C2S1 XTKDKYQZUQNXEA-UHFFFAOYSA-N 0.000 description 2
• YEXNYGZIMFEPGK-UHFFFAOYSA-N methyl 1-[[3-fluoro-4-[6-(1-phenylcyclopropyl)-1,3-benzothiazol-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)C=C2S1 YEXNYGZIMFEPGK-UHFFFAOYSA-N 0.000 description 2
• XGZKADDINVFAOE-UHFFFAOYSA-N methyl 1-[[3-nitro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1[N+]([O-])=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 XGZKADDINVFAOE-UHFFFAOYSA-N 0.000 description 2
• PASJWLRDQGFOMQ-UHFFFAOYSA-N methyl 1-[[4-(5-benzoyl-[1,3]thiazolo[5,4-b]pyridin-2-yl)-3-fluorophenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(C(=O)C=3C=CC=CC=3)N=C2S1 PASJWLRDQGFOMQ-UHFFFAOYSA-N 0.000 description 2
• QFALKTNKVIRWAN-UHFFFAOYSA-N methyl 1-[[4-(5-chloro-[1,3]thiazolo[5,4-b]pyridin-2-yl)-3-fluorophenyl]methyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1CC(C=C1F)=CC=C1C1=NC2=CC=C(Cl)N=C2S1 QFALKTNKVIRWAN-UHFFFAOYSA-N 0.000 description 2
• MZAPSNQTCDHPJT-UHFFFAOYSA-N methyl 2-[[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzoyl]amino]acetate Chemical compound FC1=CC(C(=O)NCC(=O)OC)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 MZAPSNQTCDHPJT-UHFFFAOYSA-N 0.000 description 2
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