PH12015500488B1 - Cyclic ether pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use - Google Patents

Info

Publication number

PH12015500488B1

PH12015500488B1 PH12015500488A PH12015500488A PH12015500488B1 PH 12015500488 B1 PH12015500488 B1 PH 12015500488B1 PH 12015500488 A PH12015500488 A PH 12015500488A PH 12015500488 A PH12015500488 A PH 12015500488A PH 12015500488 B1 PH12015500488 B1 PH 12015500488B1

Authority

PH

Philippines

Prior art keywords

amino

pyrazol

methyl

carboxamide

thiazole

Prior art date

2012-09-26

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title abstract description 39
• 150000004292 cyclic ethers Chemical class 0.000 title abstract description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 119
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• -1 -CH Chemical group 0.000 claims description 152
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 7
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 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 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000003566 oxetanyl group Chemical group 0.000 claims description 6
• 125000003003 spiro group Chemical group 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000003725 azepanyl group Chemical group 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
• GFRLHEODARNUOY-GUTXKFCHSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(1-propan-2-ylpyrazol-4-yl)-1,3-thiazole-4-carboxamide Chemical compound C1=NN(C(C)C)C=C1C1=NC(C(=O)NC2=C(N(C)N=C2)[C@H]2OC[C@H](F)[C@H](N)CC2)=C(N)S1 GFRLHEODARNUOY-GUTXKFCHSA-N 0.000 claims 1
• SCADKGSQUJNFSO-SCRDCRAPSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,5-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC(F)=CC(F)=C1F SCADKGSQUJNFSO-SCRDCRAPSA-N 0.000 claims 1
• KVYQPSVHULBNGT-LOWVWBTDSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,6-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC(F)=C1F KVYQPSVHULBNGT-LOWVWBTDSA-N 0.000 claims 1
• SIBVIIMSGDHMIW-SCRDCRAPSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(cyclopenten-1-yl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CCCC1 SIBVIIMSGDHMIW-SCRDCRAPSA-N 0.000 claims 1
• VNGONKQOHVSHOB-ZOWXZIJZSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-[2-(trifluoromethoxy)phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=CC=C1OC(F)(F)F VNGONKQOHVSHOB-ZOWXZIJZSA-N 0.000 claims 1
• PYGKGAMKDMHKDO-SCRDCRAPSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-[2-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=CC(C(F)(F)F)=C1F PYGKGAMKDMHKDO-SCRDCRAPSA-N 0.000 claims 1
• FQPFSDUEXAZVDE-GUTXKFCHSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-[2-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=C(C(F)(F)F)C=C1F FQPFSDUEXAZVDE-GUTXKFCHSA-N 0.000 claims 1
• RSMUFDALPJSTHE-SCRDCRAPSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-[3-fluoro-2-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=CC(F)=C1C(F)(F)F RSMUFDALPJSTHE-SCRDCRAPSA-N 0.000 claims 1
• NCLFDUDPYBHZOA-SNPRPXQTSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,5-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=C(N)SC(C=2C(=C(F)C=C(F)C=2)F)=N1 NCLFDUDPYBHZOA-SNPRPXQTSA-N 0.000 claims 1
• BESIACQRKWNYKW-XBFCOCLRSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,6-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=C(N)SC(C=2C(=C(F)C=CC=2F)F)=N1 BESIACQRKWNYKW-XBFCOCLRSA-N 0.000 claims 1
• DIMVKXSIEFRKTK-PVAVHDDUSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2-fluoro-5-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=C(N)SC(C=2C(=CC=C(C)C=2)F)=N1 DIMVKXSIEFRKTK-PVAVHDDUSA-N 0.000 claims 1
• DPGXZYHVDNHUNY-BZPMIXESSA-N 5-amino-n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(1,5-dimethylpyrazol-4-yl)-1,3-thiazole-4-carboxamide Chemical compound C1=NN(C)C(C)=C1C1=NC(C(=O)NC2=C(N(C)N=C2)[C@H]2OC[C@@H](F)[C@H](N)CC2)=C(N)S1 DPGXZYHVDNHUNY-BZPMIXESSA-N 0.000 claims 1
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• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
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• YEFRWBWOKSAGPU-JLSDUUJJSA-N n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,6-difluoro-4-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=CSC(C=2C(=CC(OC)=CC=2F)F)=N1 YEFRWBWOKSAGPU-JLSDUUJJSA-N 0.000 claims 1
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