JP2011524906A5 - - Google Patents
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- Publication number
- JP2011524906A5 JP2011524906A5 JP2011514619A JP2011514619A JP2011524906A5 JP 2011524906 A5 JP2011524906 A5 JP 2011524906A5 JP 2011514619 A JP2011514619 A JP 2011514619A JP 2011514619 A JP2011514619 A JP 2011514619A JP 2011524906 A5 JP2011524906 A5 JP 2011524906A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- phenyl
- thiazolo
- pyridin
- phenylcyclopropyl
- 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.)
- Granted
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- -1 monosubstituted amino Chemical group 0.000 claims 88
- 125000000217 alkyl group Chemical group 0.000 claims 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 27
- 229910052799 carbon Inorganic materials 0.000 claims 26
- 229910052731 fluorine Inorganic materials 0.000 claims 19
- 125000001188 haloalkyl group Chemical group 0.000 claims 18
- 229910052801 chlorine Inorganic materials 0.000 claims 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000002253 acid Substances 0.000 claims 12
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 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 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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000004011 3 membered carbocyclic group Chemical group 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
- 125000001845 4 membered carbocyclic group Chemical group 0.000 claims 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 239000005973 Carvone Substances 0.000 claims 2
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims 2
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 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 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
- 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 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
- 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
- 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
- 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
- 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
- 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 1
- 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 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
- 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 1
- 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 1
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- 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
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- 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
- 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 1
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- 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
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- 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 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
- 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 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
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- 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
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- 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
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- UMVZQXCHROWXCM-UHFFFAOYSA-N n-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound FC1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1C1=NC2=CC=C(C3(CC3)C=3C=CC=CC=3)N=C2S1 UMVZQXCHROWXCM-UHFFFAOYSA-N 0.000 claims 1
- RQZHJTNQCQBUTE-UHFFFAOYSA-N n-benzyl-2-[3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]ethanamine Chemical compound C=1C=C(C=2SC3=NC(=CC=C3N=2)C2(CC2)C=2C=CC=CC=2)C(F)=CC=1CCNCC1=CC=CC=C1 RQZHJTNQCQBUTE-UHFFFAOYSA-N 0.000 claims 1
- HYMNOIMQTZDKMR-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]benzamide Chemical compound FC1=CC(C(=O)NC2CC2)=CC=C1C(SC1=N2)=NC1=CC=C2C1(C=2C=CC=CC=2)CC1 HYMNOIMQTZDKMR-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- VLVCDUSVTXIWGW-UHFFFAOYSA-N Nc(cc1)ccc1I Chemical compound Nc(cc1)ccc1I VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 2
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| AR079981A1 (es) * | 2010-01-13 | 2012-03-07 | Sanofi Aventis | Derivados de acido carboxilico que comprenden un anillo de oxoazolopirimidina 2,5,7- sustituido |
| UY33178A (es) * | 2010-01-13 | 2011-08-31 | Sanofi Aventis | Derivados de ácido carboxílico heteroxíclicos que comprenden un anillo de oxazolopirimidina 2, 5, 7-sustituido |
| AR079980A1 (es) | 2010-01-13 | 2012-03-07 | Sanofi Aventis | Derivados de oxazolopirimidina sustituida en 2,5,7 |
| CN102791717B (zh) | 2010-01-14 | 2016-03-30 | 赛诺菲 | 具有2,5-取代的噁唑并嘧啶环的羧酸衍生物 |
| CN102834400B (zh) * | 2010-01-14 | 2015-06-10 | 赛诺菲 | 2,5-取代的*唑并嘧啶衍生物 |
| DK2523960T3 (da) * | 2010-01-14 | 2014-01-20 | Sanofi Sa | Heterocykliske carboxylsyrederivater med en 2,5-substitueret oxazolopyrimidinring |
| TW201206429A (en) * | 2010-07-08 | 2012-02-16 | Merck Serono Sa | Substituted oxadiazole derivatives |
| MX2013003019A (es) | 2010-09-15 | 2013-05-28 | Hoffmann La Roche | Compuestos de azabenzotiazol, composiciones y metodos de uso. |
| WO2012130633A1 (en) * | 2011-03-25 | 2012-10-04 | Boehringer Ingelheim International Gmbh | Pyrazole compounds as crth2 antagonists |
| US9321787B2 (en) | 2011-07-07 | 2016-04-26 | Sanofi | Carboxylic acid derivatives having an oxazolo[5,4-d]pyrimidine ring |
| US8735402B2 (en) * | 2011-07-07 | 2014-05-27 | Sanofi | Cycloalkyloxycarboxylic acid derivatives |
| US8907093B2 (en) | 2011-07-07 | 2014-12-09 | Sanofi | Carboxylic acid derivatives having an oxazolo[4,5-c]pyridine ring |
| US8580816B2 (en) | 2011-07-07 | 2013-11-12 | Sanofi | Carboxylic acid derivatives having an oxazolo[5,4-b]pyridine ring |
| WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
| CN104380596B (zh) * | 2012-07-20 | 2018-01-02 | 三菱电机株式会社 | 保持框架和太阳能电池模块 |
| JP2016509036A (ja) | 2013-02-20 | 2016-03-24 | バイエル・ファルマ・アクティエンゲゼルシャフト | Ｍｋｎｋ１阻害剤としての置換イミダゾ［１，２−ｂ］ピリダジン |
| NZ716822A (en) | 2013-08-21 | 2017-10-27 | Alios Biopharma Inc | Antiviral compounds |
| WO2016182850A1 (en) | 2015-05-08 | 2016-11-17 | Albany Molecular Research, Inc. | Methods and intermediates for the preparation of omacetaxine and cephalotaxine derivatives thereof |
| IL252151A0 (en) | 2017-05-07 | 2017-07-31 | Fainzilber Michael | Treatment of stress disorders |
| IL271149B2 (en) * | 2017-06-14 | 2024-05-01 | Trevena Inc | Compounds for modulating s1p1 activity and methods of using the same |
| CN110256466A (zh) * | 2019-07-31 | 2019-09-20 | 昆山迪安医学检验实验室有限公司 | 一种噻唑[5,4-b]-吡啶基生物活性化合物的制备方法及其抗肿瘤活性的检测 |
| EP4061352A4 (en) | 2019-11-19 | 2024-02-28 | Trevena, Inc. | COMPOUNDS AND METHODS FOR PRODUCING S1P1-MODULATING COMPOUNDS |
| CN115611793A (zh) * | 2021-07-14 | 2023-01-17 | 山东新华制药股份有限公司 | 硫代酰胺类化合物的合成方法 |
| CN116410213A (zh) * | 2023-02-21 | 2023-07-11 | 武汉大学 | 一种合成3-碳基-1-硼基环类化合物的方法 |
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| AU2001292350A1 (en) | 2000-10-05 | 2002-04-15 | Takeda Chemical Industries Ltd. | Promoters for the proliferation and differentiation of stem cells and/or neuron precursor cells |
| US6951848B2 (en) | 2001-03-12 | 2005-10-04 | Millennium Pharmaceuticals, Inc., | Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor |
| AU2002349477A1 (en) | 2001-11-26 | 2003-06-10 | Takeda Chemical Industries, Ltd. | Bicyclic derivative, process for producing the same, and use |
| US7479504B2 (en) | 2002-01-18 | 2009-01-20 | Merck & Co., Inc. | Edg receptor agonists |
| CA2523677A1 (en) * | 2003-04-30 | 2004-11-11 | Novartis Ag | Aminopropanol derivatives as sphingosine-1-phosphate receptor modulators |
| WO2004098494A2 (en) | 2003-04-30 | 2004-11-18 | Cytokinetics, Inc. | Compounds, compositions, and methods |
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| EP1799659A1 (en) | 2004-10-13 | 2007-06-27 | PTC Therapeutics, Inc. | Compounds for nonsense suppression, and methods for their use |
| US7919519B2 (en) * | 2005-11-23 | 2011-04-05 | Epix Pharmaceuticals Inc. | S1P receptor modulating compounds and use thereof |
| EP1965807A4 (en) * | 2005-11-23 | 2010-10-27 | Epix Delaware Inc | S1P RECEPTOR MODULATING COMPOUNDS AND THEIR USE |
| US20090182003A1 (en) | 2006-01-13 | 2009-07-16 | President And Fellows Of Harvard College | Methods and Compositions for Treatment Cell Proliferative Disorders |
| JP2009526761A (ja) | 2006-01-30 | 2009-07-23 | アレイ バイオファーマ、インコーポレイテッド | ヘテロ二環式チオフェン化合物および使用の方法 |
| JP4897834B2 (ja) | 2006-02-08 | 2012-03-14 | コダック グラフィック コミュニケーションズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | ベンゾキサゾール誘導体およびその類似体を増感剤として含む紫外線感受性平版印刷版前駆体 |
| JP2009530389A (ja) * | 2006-03-21 | 2009-08-27 | エピックス デラウェア， インコーポレイテッド | Ｓ１ｐ受容体調節化合物及びその使用 |
| US7989472B2 (en) | 2006-03-23 | 2011-08-02 | Merck Sharp & Dohme Corp. | Glucagon receptor antagonist compounds, compositions containing such compounds and methods of use |
| US20100055071A1 (en) | 2006-11-21 | 2010-03-04 | Martin Robert Leivers | Anti-Viral Compounds |
| CA2671315A1 (en) | 2006-12-11 | 2008-06-19 | Novartis Ag | Method of preventing or treating myocardial ischemia by inhibiting dgat1 enzyme with a dgat1 inhibitor |
| MX2009010060A (es) | 2007-03-21 | 2010-01-20 | Epix Pharm Inc | Compuestos moduladores del receptor de esfingosin-1-fosfato y uso de los mismos. |
| JP2008308448A (ja) | 2007-06-15 | 2008-12-25 | Sankyo Agro Kk | （３−硫黄原子置換フェニル）へテロアリール誘導体 |
| ES2360929T3 (es) * | 2007-09-20 | 2011-06-10 | Amgen Inc. | Derivados del ácido 1-(4-(4-bencilbenzamido)-bencil)azetidin-3-carboxílico y compuestos relacionados como moduladores del receptor s1p para el tratamiento de trastornos inmunitarios. |
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- 2009-06-18 EP EP09767088.9A patent/EP2306994B1/en not_active Not-in-force
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