JP2016515582A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016515582A5 JP2016515582A5 JP2016505551A JP2016505551A JP2016515582A5 JP 2016515582 A5 JP2016515582 A5 JP 2016515582A5 JP 2016505551 A JP2016505551 A JP 2016505551A JP 2016505551 A JP2016505551 A JP 2016505551A JP 2016515582 A5 JP2016515582 A5 JP 2016515582A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- pyridin
- carbonyl
- hydroxy
- methylbenzonitrile
- 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
Links
- 150000003839 salts Chemical class 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 8
- 229940079593 drug Drugs 0.000 claims 7
- 239000000178 monomer Substances 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- KOTAMPMVFIDFFG-UHFFFAOYSA-N C1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 KOTAMPMVFIDFFG-UHFFFAOYSA-N 0.000 claims 2
- GMAUMHRCNZGBSX-INIZCTEOSA-N C1CN(C)[C@@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1CN(C)[C@@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 GMAUMHRCNZGBSX-INIZCTEOSA-N 0.000 claims 2
- GMAUMHRCNZGBSX-MRXNPFEDSA-N C1CN(C)[C@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1CN(C)[C@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 GMAUMHRCNZGBSX-MRXNPFEDSA-N 0.000 claims 2
- XIJUIXPKUMOZSE-UHFFFAOYSA-N C1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 XIJUIXPKUMOZSE-UHFFFAOYSA-N 0.000 claims 2
- NYMWLCZMTLIVNF-UHFFFAOYSA-N C1CN(CCC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1CN(CCC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 NYMWLCZMTLIVNF-UHFFFAOYSA-N 0.000 claims 2
- WPCDPGKXRVRPEG-UHFFFAOYSA-N CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC(F)F)CC2)N=C1 Chemical compound CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC(F)F)CC2)N=C1 WPCDPGKXRVRPEG-UHFFFAOYSA-N 0.000 claims 2
- PADVJXMCJSCREC-MRXNPFEDSA-N C[C@@H]1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C[C@@H]1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 PADVJXMCJSCREC-MRXNPFEDSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- GHBASXWDGOMQBV-KRWDZBQOSA-N C([C@@H]1C)N(C(=O)C=2C=NC(=CC=2)N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)CCN1C1CC1 Chemical compound C([C@@H]1C)N(C(=O)C=2C=NC(=CC=2)N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)CCN1C1CC1 GHBASXWDGOMQBV-KRWDZBQOSA-N 0.000 claims 1
- GHBASXWDGOMQBV-QGZVFWFLSA-N C([C@H]1C)N(C(=O)C=2C=NC(=CC=2)N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)CCN1C1CC1 Chemical compound C([C@H]1C)N(C(=O)C=2C=NC(=CC=2)N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)CCN1C1CC1 GHBASXWDGOMQBV-QGZVFWFLSA-N 0.000 claims 1
- UXKVNAXJRHHIKJ-UHFFFAOYSA-N C1=C(C#N)C(C)=C(C)C(C2=C(N(N=C2)C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)O)=C1 Chemical compound C1=C(C#N)C(C)=C(C)C(C2=C(N(N=C2)C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)O)=C1 UXKVNAXJRHHIKJ-UHFFFAOYSA-N 0.000 claims 1
- PTMCUEQTYXHFNN-UHFFFAOYSA-N C1C(C)(C)N(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1C(C)(C)N(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 PTMCUEQTYXHFNN-UHFFFAOYSA-N 0.000 claims 1
- KUMVQFHINQOEKL-UHFFFAOYSA-N C1C(C)(C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1C(C)(C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 KUMVQFHINQOEKL-UHFFFAOYSA-N 0.000 claims 1
- YMCWQFWYUFDSAD-UHFFFAOYSA-N C1C(C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1C(C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 YMCWQFWYUFDSAD-UHFFFAOYSA-N 0.000 claims 1
- MGCKIAJRAPXDQI-UHFFFAOYSA-N C1C(C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1C(C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 MGCKIAJRAPXDQI-UHFFFAOYSA-N 0.000 claims 1
- SCUUFDLZFXDHAW-UHFFFAOYSA-N C1C(C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1C(C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 SCUUFDLZFXDHAW-UHFFFAOYSA-N 0.000 claims 1
- KAOROSNDUNJDEV-UHFFFAOYSA-N C1C(C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C1C(C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 KAOROSNDUNJDEV-UHFFFAOYSA-N 0.000 claims 1
- VZDRTKJJJSODLC-UHFFFAOYSA-N C1C(C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1C(C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 VZDRTKJJJSODLC-UHFFFAOYSA-N 0.000 claims 1
- NBZDXOYSFCIINH-UHFFFAOYSA-N C1C(C)N(CCC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1C(C)N(CCC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 NBZDXOYSFCIINH-UHFFFAOYSA-N 0.000 claims 1
- YBAHSUMYFQBXPY-UHFFFAOYSA-N C1C(F)(F)CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1C(F)(F)CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 YBAHSUMYFQBXPY-UHFFFAOYSA-N 0.000 claims 1
- CUJIBKJJNSFQLB-UHFFFAOYSA-N C1CN(C)C(C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1CN(C)C(C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 CUJIBKJJNSFQLB-UHFFFAOYSA-N 0.000 claims 1
- GMAUMHRCNZGBSX-UHFFFAOYSA-N C1CN(C)C(C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1CN(C)C(C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 GMAUMHRCNZGBSX-UHFFFAOYSA-N 0.000 claims 1
- WRXNYQXCYXUVKO-UHFFFAOYSA-N C1CN(C)CCCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1CN(C)CCCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 WRXNYQXCYXUVKO-UHFFFAOYSA-N 0.000 claims 1
- CHZGCHCOWXSCQA-UHFFFAOYSA-N C1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 CHZGCHCOWXSCQA-UHFFFAOYSA-N 0.000 claims 1
- XFQHZUOLRHLKJY-UHFFFAOYSA-N C1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 XFQHZUOLRHLKJY-UHFFFAOYSA-N 0.000 claims 1
- LPBXHKDJASJNGV-UHFFFAOYSA-N C1CN(C)CCN1C(=O)C1=CN=C(N2C(=C(C=N2)C=2C=CC(=CC=2)C#N)O)C=C1C Chemical compound C1CN(C)CCN1C(=O)C1=CN=C(N2C(=C(C=N2)C=2C=CC(=CC=2)C#N)O)C=C1C LPBXHKDJASJNGV-UHFFFAOYSA-N 0.000 claims 1
- CUJIBKJJNSFQLB-AWEZNQCLSA-N C1CN(C)[C@@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1CN(C)[C@@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 CUJIBKJJNSFQLB-AWEZNQCLSA-N 0.000 claims 1
- WPXKSRBLVCKJBE-HNNXBMFYSA-N C1CN(C)[C@@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C1CN(C)[C@@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 WPXKSRBLVCKJBE-HNNXBMFYSA-N 0.000 claims 1
- CUJIBKJJNSFQLB-CQSZACIVSA-N C1CN(C)[C@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1CN(C)[C@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 CUJIBKJJNSFQLB-CQSZACIVSA-N 0.000 claims 1
- WPXKSRBLVCKJBE-OAHLLOKOSA-N C1CN(C)[C@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C1CN(C)[C@H](C)CN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 WPXKSRBLVCKJBE-OAHLLOKOSA-N 0.000 claims 1
- DZAMHPAXCHOATI-UHFFFAOYSA-N C1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(C)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(C)C(C#N)=CC=2)C)O)N=C1 DZAMHPAXCHOATI-UHFFFAOYSA-N 0.000 claims 1
- LTYWZKKDTAQOMP-UHFFFAOYSA-N C1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 LTYWZKKDTAQOMP-UHFFFAOYSA-N 0.000 claims 1
- KMFBTSKYULYULN-UHFFFAOYSA-N C1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 KMFBTSKYULYULN-UHFFFAOYSA-N 0.000 claims 1
- XPQCRZDFMYXKQD-UHFFFAOYSA-N C1CN(CCC)CCCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1CN(CCC)CCCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 XPQCRZDFMYXKQD-UHFFFAOYSA-N 0.000 claims 1
- YMCWQFWYUFDSAD-MRXNPFEDSA-N C1[C@@H](C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1[C@@H](C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 YMCWQFWYUFDSAD-MRXNPFEDSA-N 0.000 claims 1
- MGCKIAJRAPXDQI-GOSISDBHSA-N C1[C@@H](C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1[C@@H](C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 MGCKIAJRAPXDQI-GOSISDBHSA-N 0.000 claims 1
- SCUUFDLZFXDHAW-OAHLLOKOSA-N C1[C@@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1[C@@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 SCUUFDLZFXDHAW-OAHLLOKOSA-N 0.000 claims 1
- KAOROSNDUNJDEV-MRXNPFEDSA-N C1[C@@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C1[C@@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 KAOROSNDUNJDEV-MRXNPFEDSA-N 0.000 claims 1
- VZDRTKJJJSODLC-QGZVFWFLSA-N C1[C@@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1[C@@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 VZDRTKJJJSODLC-QGZVFWFLSA-N 0.000 claims 1
- NBZDXOYSFCIINH-GOSISDBHSA-N C1[C@@H](C)N(CCC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1[C@@H](C)N(CCC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 NBZDXOYSFCIINH-GOSISDBHSA-N 0.000 claims 1
- YMCWQFWYUFDSAD-INIZCTEOSA-N C1[C@H](C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 YMCWQFWYUFDSAD-INIZCTEOSA-N 0.000 claims 1
- MGCKIAJRAPXDQI-SFHVURJKSA-N C1[C@H](C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 MGCKIAJRAPXDQI-SFHVURJKSA-N 0.000 claims 1
- SCUUFDLZFXDHAW-HNNXBMFYSA-N C1[C@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C1[C@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 SCUUFDLZFXDHAW-HNNXBMFYSA-N 0.000 claims 1
- KAOROSNDUNJDEV-INIZCTEOSA-N C1[C@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C1[C@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 KAOROSNDUNJDEV-INIZCTEOSA-N 0.000 claims 1
- VZDRTKJJJSODLC-KRWDZBQOSA-N C1[C@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1[C@H](C)N(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 VZDRTKJJJSODLC-KRWDZBQOSA-N 0.000 claims 1
- NBZDXOYSFCIINH-SFHVURJKSA-N C1[C@H](C)N(CCC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C1[C@H](C)N(CCC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 NBZDXOYSFCIINH-SFHVURJKSA-N 0.000 claims 1
- GSBQWIXIOHAFJM-UHFFFAOYSA-N CC(C1)N(C)CCN1C(C(C=C1)=CN=C1N1N=CC(C2=CC(C)=CC(C#N)=C2F)=C1O)=O Chemical compound CC(C1)N(C)CCN1C(C(C=C1)=CN=C1N1N=CC(C2=CC(C)=CC(C#N)=C2F)=C1O)=O GSBQWIXIOHAFJM-UHFFFAOYSA-N 0.000 claims 1
- JFQJPHFAUYJAKN-UHFFFAOYSA-N CC1=C(F)C(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)N=C1 Chemical compound CC1=C(F)C(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)N=C1 JFQJPHFAUYJAKN-UHFFFAOYSA-N 0.000 claims 1
- SGEXNVZZGGTYMM-UHFFFAOYSA-N CC1=C(F)C(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CCC2)C2CC2)N=C1 Chemical compound CC1=C(F)C(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CCC2)C2CC2)N=C1 SGEXNVZZGGTYMM-UHFFFAOYSA-N 0.000 claims 1
- XXNZHNBMTBCMSS-UHFFFAOYSA-N CC1=CC(C#N)=C(F)C=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)N=C1 Chemical compound CC1=CC(C#N)=C(F)C=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)N=C1 XXNZHNBMTBCMSS-UHFFFAOYSA-N 0.000 claims 1
- ACDVMPSJGOBICZ-UHFFFAOYSA-N CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC(F)(F)F)CC2)N=C1 Chemical compound CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC(F)(F)F)CC2)N=C1 ACDVMPSJGOBICZ-UHFFFAOYSA-N 0.000 claims 1
- AVCVVAOCHMDAIZ-UHFFFAOYSA-N CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C(C)(C)C)N=C1 Chemical compound CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C(C)(C)C)N=C1 AVCVVAOCHMDAIZ-UHFFFAOYSA-N 0.000 claims 1
- HTVYGHSENHGVDC-UHFFFAOYSA-N CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)N=C1 Chemical compound CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)N=C1 HTVYGHSENHGVDC-UHFFFAOYSA-N 0.000 claims 1
- BGLIJKLXIGEHBO-UHFFFAOYSA-N CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CCC2)N=C1 Chemical compound CC1=CC(C#N)=CC=C1C1=C(O)N(C=2N=CC(=CC=2)C(=O)N2CCN(CC2)C2CCC2)N=C1 BGLIJKLXIGEHBO-UHFFFAOYSA-N 0.000 claims 1
- GHBASXWDGOMQBV-UHFFFAOYSA-N CC1CN(C(=O)C=2C=NC(=CC=2)N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)CCN1C1CC1 Chemical compound CC1CN(C(=O)C=2C=NC(=CC=2)N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)CCN1C1CC1 GHBASXWDGOMQBV-UHFFFAOYSA-N 0.000 claims 1
- PADVJXMCJSCREC-UHFFFAOYSA-N CC1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound CC1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 PADVJXMCJSCREC-UHFFFAOYSA-N 0.000 claims 1
- IYHOGTXVYYGKLF-UHFFFAOYSA-N CC1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound CC1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 IYHOGTXVYYGKLF-UHFFFAOYSA-N 0.000 claims 1
- ZESMXBFMRPIQSH-UHFFFAOYSA-N CC1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound CC1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 ZESMXBFMRPIQSH-UHFFFAOYSA-N 0.000 claims 1
- OCESGFVEORXWLG-UHFFFAOYSA-N CC1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound CC1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 OCESGFVEORXWLG-UHFFFAOYSA-N 0.000 claims 1
- TVDZPNOFNQSAPS-UHFFFAOYSA-N CCC(CC)N(CC1)CCN1C(C(C=C1)=CN=C1N1N=CC(C(C(C)=CC=C2)=C2C#N)=C1O)=O Chemical compound CCC(CC)N(CC1)CCN1C(C(C=C1)=CN=C1N1N=CC(C(C(C)=CC=C2)=C2C#N)=C1O)=O TVDZPNOFNQSAPS-UHFFFAOYSA-N 0.000 claims 1
- IYHOGTXVYYGKLF-OAHLLOKOSA-N C[C@@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C[C@@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 IYHOGTXVYYGKLF-OAHLLOKOSA-N 0.000 claims 1
- ZESMXBFMRPIQSH-MRXNPFEDSA-N C[C@@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C[C@@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 ZESMXBFMRPIQSH-MRXNPFEDSA-N 0.000 claims 1
- OCESGFVEORXWLG-QGZVFWFLSA-N C[C@@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C[C@@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 OCESGFVEORXWLG-QGZVFWFLSA-N 0.000 claims 1
- PADVJXMCJSCREC-INIZCTEOSA-N C[C@H]1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C[C@H]1CN(C)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 PADVJXMCJSCREC-INIZCTEOSA-N 0.000 claims 1
- IYHOGTXVYYGKLF-HNNXBMFYSA-N C[C@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 Chemical compound C[C@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=C(F)C(C#N)=CC=2)C)O)N=C1 IYHOGTXVYYGKLF-HNNXBMFYSA-N 0.000 claims 1
- ZESMXBFMRPIQSH-INIZCTEOSA-N C[C@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 Chemical compound C[C@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=C(F)C=2)C#N)C)O)N=C1 ZESMXBFMRPIQSH-INIZCTEOSA-N 0.000 claims 1
- OCESGFVEORXWLG-KRWDZBQOSA-N C[C@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 Chemical compound C[C@H]1CN(CC)CCN1C(=O)C1=CC=C(N2C(=C(C=N2)C=2C(=CC(=CC=2)C#N)C)O)N=C1 OCESGFVEORXWLG-KRWDZBQOSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- -1 cyanomethyl Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361806806P | 2013-03-29 | 2013-03-29 | |
| US61/806,806 | 2013-03-29 | ||
| US201361916715P | 2013-12-16 | 2013-12-16 | |
| US61/916,715 | 2013-12-16 | ||
| PCT/US2014/031918 WO2014160810A1 (en) | 2013-03-29 | 2014-03-26 | 6-(5-hydroxy-1h-pyrazol-1-yl)nicotinamide derivatives and their use as phd inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018009987A Division JP6462911B2 (ja) | 2013-03-29 | 2018-01-24 | ６−（５−ヒドロキシ−１ｈ−ピラゾール−１−イル）ニコチンアミド誘導体およびｐｈｄ阻害剤としてのそれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016515582A JP2016515582A (ja) | 2016-05-30 |
| JP2016515582A5 true JP2016515582A5 (https=) | 2017-05-18 |
| JP6282724B2 JP6282724B2 (ja) | 2018-02-21 |
Family
ID=50792544
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016505551A Active JP6282724B2 (ja) | 2013-03-29 | 2014-03-26 | ６−（５−ヒドロキシ−１ｈ−ピラゾール−１−イル）ニコチンアミド誘導体およびｐｈｄ阻害剤としてのそれらの使用 |
| JP2018009987A Active JP6462911B2 (ja) | 2013-03-29 | 2018-01-24 | ６−（５−ヒドロキシ−１ｈ−ピラゾール−１−イル）ニコチンアミド誘導体およびｐｈｄ阻害剤としてのそれらの使用 |
| JP2018245492A Active JP6640978B2 (ja) | 2013-03-29 | 2018-12-27 | ６−（５−ヒドロキシ−１ｈ−ピラゾール−１−イル）ニコチンアミド誘導体およびｐｈｄ阻害剤としてのそれらの使用 |
| JP2019235781A Active JP6874114B2 (ja) | 2013-03-29 | 2019-12-26 | ６−（５−ヒドロキシ−１ｈ−ピラゾール−１−イル）ニコチンアミド誘導体およびｐｈｄ阻害剤としてのそれらの使用 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018009987A Active JP6462911B2 (ja) | 2013-03-29 | 2018-01-24 | ６−（５−ヒドロキシ−１ｈ−ピラゾール−１−イル）ニコチンアミド誘導体およびｐｈｄ阻害剤としてのそれらの使用 |
| JP2018245492A Active JP6640978B2 (ja) | 2013-03-29 | 2018-12-27 | ６−（５−ヒドロキシ−１ｈ−ピラゾール−１−イル）ニコチンアミド誘導体およびｐｈｄ阻害剤としてのそれらの使用 |
| JP2019235781A Active JP6874114B2 (ja) | 2013-03-29 | 2019-12-26 | ６−（５−ヒドロキシ−１ｈ−ピラゾール−１−イル）ニコチンアミド誘導体およびｐｈｄ阻害剤としてのそれらの使用 |
Country Status (40)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA031647B1 (ru) | 2013-03-29 | 2019-02-28 | Такеда Фармасьютикал Компани Лимитед | 6-(5-гидрокси-1h-пиразол-1-ил)никотинамидные ингибиторы phd |
| TWI735416B (zh) | 2014-10-06 | 2021-08-11 | 美商維泰克斯製藥公司 | 囊腫纖維化症跨膜傳導調節蛋白之調節劑 |
| SI3519401T1 (sl) | 2016-09-30 | 2022-01-31 | Vertex Pharmaceuticals Incorporated | Modulator regulatorja transmembranske prevodnosti pri cistični fibrozi, farmacevtski sestavki, postopki zdravljenja in proces za izdelavo modulatorja |
| CN110267948B (zh) | 2016-12-09 | 2023-12-08 | 弗特克斯药品有限公司 | 囊性纤维化跨膜传导调控剂的调节剂、药物组合物、治疗方法和制备所述调节剂的方法 |
| AU2018279646B2 (en) | 2017-06-08 | 2023-04-06 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| CN107163043A (zh) * | 2017-06-16 | 2017-09-15 | 上海毕得医药科技有限公司 | 一种吡唑并[1,5‑a]吡啶‑3‑羧酸酯衍生物的合成方法 |
| MA49631A (fr) | 2017-07-17 | 2020-05-27 | Vertex Pharma | Méthodes de traitement de la fibrose kystique |
| TWI799435B (zh) | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | 製備化合物之製程 |
| US10654829B2 (en) | 2017-10-19 | 2020-05-19 | Vertex Pharmaceuticals Incorporated | Crystalline forms and compositions of CFTR modulators |
| KR102716244B1 (ko) | 2017-12-08 | 2024-10-14 | 버텍스 파마슈티칼스 인코포레이티드 | 낭포성 섬유증 막횡단 전도 조절자의 조정제의 제조 방법 |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| JP7301042B2 (ja) | 2018-03-30 | 2023-06-30 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除組成物 |
| US20210139514A1 (en) * | 2018-04-05 | 2021-05-13 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| EP3774825A1 (en) * | 2018-04-13 | 2021-02-17 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| CN111349077B (zh) * | 2019-02-02 | 2022-06-28 | 杭州华东医药集团新药研究院有限公司 | 一种哒嗪衍生物及其制备方法和医药用途 |
| AR121618A1 (es) * | 2020-03-20 | 2022-06-22 | Akebia Therapeutics Inc | Compuestos inhibidores de phd, composiciones y métodos de uso |
| JP2023518543A (ja) * | 2020-03-20 | 2023-05-02 | アケビア セラピューティクス インコーポレイテッド | Ｐｈｄ阻害剤化合物、組成物、及びそれらの使用 |
| EP4121426A1 (en) * | 2020-03-20 | 2023-01-25 | Akebia Therapeutics Inc. | Phd inhibitor compounds, compositions, and use |
| WO2021216530A1 (en) | 2020-04-20 | 2021-10-28 | Akebia Therapeutics, Inc. | Treatment of viral infections, of organ injury, and of related conditions using a hif prolyl hydroxylase inhibitor or a hif-alpha stabilizer |
| WO2022150623A1 (en) | 2021-01-08 | 2022-07-14 | Akebia Therapeutics, Inc. | Compounds and composition for the treatment of anemia |
| EP4347022A1 (en) | 2021-05-27 | 2024-04-10 | Keryx Biopharmaceuticals, Inc. | Pediatric formulations of ferric citrate |
| JP7710897B2 (ja) * | 2021-06-01 | 2025-07-22 | 三菱ガス化学ネクスト株式会社 | １－アルキル－５－ヒドロキシピラゾールの製造方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663327A (en) | 1984-05-23 | 1987-05-05 | Bayer Aktiengesellschaft | 1-heteroaryl-4-aryl-pyrazolin-5-ones |
| DE3443308A1 (de) * | 1984-11-28 | 1986-05-28 | Bayer Ag, 5090 Leverkusen | 1-heteroaryl-4-aryl-pyrazolin-5-one zur verwendung als arzneimittel |
| US20040014744A1 (en) * | 2002-04-05 | 2004-01-22 | Fortuna Haviv | Substituted pyridines having antiangiogenic activity |
| WO2004022540A2 (en) * | 2002-09-06 | 2004-03-18 | Fujisawa Pharmaceutical Co., Ltd. | Pyridazinone and pyridone derivatives as adenosine antagonists |
| DE102005019712A1 (de) | 2005-04-28 | 2006-11-09 | Bayer Healthcare Ag | Dipyridyl-dihydropyrazolone und ihre Verwendung |
| KR20080034944A (ko) | 2005-08-19 | 2008-04-22 | 아스트라제네카 아베 | 결핵 치료용 피라졸론 유도체 |
| PL3357911T3 (pl) * | 2006-06-26 | 2022-09-05 | Akebia Therapeutics Inc. | Inhibitory prolilohydroksylazy i sposoby ich użycia |
| TWI386405B (zh) * | 2006-09-05 | 2013-02-21 | 咪唑衍生物 | |
| DE102006050516A1 (de) * | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dihydropyrazolone und ihre Verwendung |
| DE102006050515A1 (de) * | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dipyridiyl-dihydropyrazolone und ihre Verwendung |
| AR064693A1 (es) | 2006-12-29 | 2009-04-22 | Abbott Gmbh & Co Kg | Compuestos carboxamidas y su utilizacion en la elaboracion de un medicamento para el tratamiento de enfermedades asociadas a alta actividad de calpaina. |
| DE102007044032A1 (de) | 2007-09-14 | 2009-03-19 | Bayer Healthcare Ag | Substituierte heterocyclische Verbindungen und ihre Verwendung |
| ES2524883T3 (es) * | 2008-03-18 | 2014-12-15 | Merck Sharp & Dohme Corp. | 4-Hidroxipirimidina-5-carboxamidas sustituidas |
| US8268834B2 (en) * | 2008-03-19 | 2012-09-18 | Novartis Ag | Pyrazine derivatives that inhibit phosphatidylinositol 3-kinase enzyme |
| AU2009334570B2 (en) * | 2008-12-29 | 2016-06-09 | Sanofi | Derivatives of 2-pyridin-2-yl-pyrazol-3(2h)-one, preparation and therapeutic use thereof |
| MA32976B1 (fr) * | 2008-12-29 | 2012-01-02 | Sanofi Sa | Derives de 2-pyridin-2-yl-pyrazol-3(2h)-one, leur preparation et leur application en therapeutique comme activateurs de hif |
| EA031647B1 (ru) * | 2013-03-29 | 2019-02-28 | Такеда Фармасьютикал Компани Лимитед | 6-(5-гидрокси-1h-пиразол-1-ил)никотинамидные ингибиторы phd |
-
2014
- 2014-03-26 EA EA201591889A patent/EA031647B1/ru unknown
- 2014-03-26 PL PL14726246T patent/PL2978752T3/pl unknown
- 2014-03-26 DK DK14726246.3T patent/DK2978752T3/en active
- 2014-03-26 SI SI201430629T patent/SI2978752T1/en unknown
- 2014-03-26 HU HUE14726246A patent/HUE038220T2/hu unknown
- 2014-03-26 AP AP2015008783A patent/AP2015008783A0/xx unknown
- 2014-03-26 RS RS20180217A patent/RS56974B1/sr unknown
- 2014-03-26 SG SG11201506749XA patent/SG11201506749XA/en unknown
- 2014-03-26 JP JP2016505551A patent/JP6282724B2/ja active Active
- 2014-03-26 TR TR2018/02632T patent/TR201802632T4/tr unknown
- 2014-03-26 CA CA2903875A patent/CA2903875C/en active Active
- 2014-03-26 PE PE2015002062A patent/PE20151860A1/es active IP Right Grant
- 2014-03-26 BR BR112015020350-7A patent/BR112015020350B1/pt active IP Right Grant
- 2014-03-26 ME MEP-2018-57A patent/ME03024B/me unknown
- 2014-03-26 PT PT147262463T patent/PT2978752T/pt unknown
- 2014-03-26 GE GEAP201413977A patent/GEP201706761B/en unknown
- 2014-03-26 CN CN201480018116.6A patent/CN105492433B/zh active Active
- 2014-03-26 KR KR1020157031268A patent/KR102376354B1/ko active Active
- 2014-03-26 EP EP14726246.3A patent/EP2978752B1/en active Active
- 2014-03-26 SM SM20180112T patent/SMT201800112T1/it unknown
- 2014-03-26 MY MYPI2015703395A patent/MY184218A/en unknown
- 2014-03-26 MX MX2015013687A patent/MX370388B/es active IP Right Grant
- 2014-03-26 UA UAA201510254A patent/UA118965C2/uk unknown
- 2014-03-26 US US14/226,722 patent/US9040522B2/en active Active
- 2014-03-26 EP EP17198051.9A patent/EP3336084B1/en active Active
- 2014-03-26 LT LTEP14726246.3T patent/LT2978752T/lt unknown
- 2014-03-26 HR HRP20180341TT patent/HRP20180341T1/hr unknown
- 2014-03-26 WO PCT/US2014/031918 patent/WO2014160810A1/en not_active Ceased
- 2014-03-26 ES ES14726246.3T patent/ES2660914T3/es active Active
- 2014-03-26 AU AU2014241183A patent/AU2014241183B2/en active Active
- 2014-03-27 JO JOP/2014/0132A patent/JO3722B1/ar active
- 2014-03-28 UY UY0001035513A patent/UY35513A/es not_active Application Discontinuation
- 2014-03-28 TW TW103111864A patent/TWI635084B/zh active
-
2015
- 2015-04-22 US US14/693,110 patent/US9345713B2/en active Active
- 2015-08-25 IL IL240803A patent/IL240803B/en active IP Right Grant
- 2015-09-03 ZA ZA2015/06484A patent/ZA201506484B/en unknown
- 2015-09-04 CL CL2015002473A patent/CL2015002473A1/es unknown
- 2015-09-07 TN TN2015000397A patent/TN2015000397A1/en unknown
- 2015-09-24 PH PH12015502248A patent/PH12015502248B1/en unknown
- 2015-10-02 CR CR20150517A patent/CR20150517A/es unknown
- 2015-10-29 EC ECIEPI201545801A patent/ECSP15045801A/es unknown
-
2016
- 2016-05-10 US US15/150,976 patent/US9708296B2/en active Active
-
2017
- 2017-06-12 US US15/620,620 patent/US9944626B2/en active Active
-
2018
- 2018-01-24 JP JP2018009987A patent/JP6462911B2/ja active Active
- 2018-02-28 CY CY20181100247T patent/CY1120029T1/el unknown
- 2018-03-01 US US15/909,801 patent/US10407409B2/en active Active
- 2018-12-27 JP JP2018245492A patent/JP6640978B2/ja active Active
-
2019
- 2019-12-26 JP JP2019235781A patent/JP6874114B2/ja active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016515582A5 (https=) | ||
| IL244787B (en) | Polymorph c of n-((4,6-dimethyl-2 oxo-1,2-dihydropyridine-3-yl)methyl)-5-(ethyl(tetrahydro-2h-pyran-4-yl)amino)-4-methyl -4'-(morpholinomethyl)-[1,1'-biphenyl]-3-carboxamide monohydrochloride, methods for its preparation, medical preparations containing it and its use | |
| SI2978752T1 (en) | 6- (5-Hydroxy-1H-pyrazol-1-yl) nicotinamide derivatives and their use as inhibitors of PHD | |
| JP2016506960A5 (https=) | ||
| JP2016040288A5 (https=) | ||
| JP2013543896A5 (https=) | ||
| JP2016506962A5 (https=) | ||
| CL2015000332A1 (es) | Forma cristalina a y racemato cristalino de 1-(5'-(5-(3,5-dicloro-4-fluorofenil)-5-(trifluorometil)-4,5-dihidroisoxazol-3-il)-3'h-espiro[azetidin-3,1'-isobenzofuran]-1-il)-2-(metilsulfonil)etanona; procedimiento de preparacion de la forma cristalina a; composicion que la comprende; y su uso para el tratamiento de una infeccion o infestacion parasitaria. | |
| JP2019509276A5 (https=) | ||
| JP2016530213A5 (https=) | ||
| JP2013531031A5 (https=) | ||
| JP2016505637A5 (https=) | ||
| JP2017513894A5 (https=) | ||
| MY190878A (en) | N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate | |
| JP2019512535A5 (https=) | ||
| JP2012522764A5 (https=) | ||
| JP2014505107A5 (https=) | ||
| JP2011037901A5 (https=) | ||
| JP2015524472A5 (https=) | ||
| RU2017120217A (ru) | 2-амино-5,5-дифтор-6-(фторметил)-6-фенил-3,4,5,6-тетрагидпропиридины в качестве ингибиторов bace1 | |
| MX2014003623A (es) | Monohidrato de mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol -2-il]-2-[4-(2-piridinil)-fenil]-n-metilacetamida con un intervalo de distribucion de tamaño de particula especifica y un intervalo de area superficial especifica para uso en formulaciones farmaceuticas. | |
| JP2013540712A5 (https=) | ||
| JP2015516427A5 (https=) | ||
| RU2017120858A (ru) | Замещенные аналоги мочевины с мостиковой связью в качестве модуляторов сиртуина | |
| RU2018114077A (ru) | Биарильное производное и содержащее его лекарственное средство |