JP2018520145A5 - - Google Patents
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- Publication number
- JP2018520145A5 JP2018520145A5 JP2017567124A JP2017567124A JP2018520145A5 JP 2018520145 A5 JP2018520145 A5 JP 2018520145A5 JP 2017567124 A JP2017567124 A JP 2017567124A JP 2017567124 A JP2017567124 A JP 2017567124A JP 2018520145 A5 JP2018520145 A5 JP 2018520145A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- compound according
- methyl
- phenyl
- alkyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 47
- -1 phenylsulfinyl Chemical group 0.000 claims 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 6
- 206010019280 Heart failures Diseases 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 5
- 230000000069 prophylactic effect Effects 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims 4
- 230000001225 therapeutic effect Effects 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 208000037906 ischaemic injury Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 claims 1
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims 1
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- QVYLSVMCFVNCNQ-UHFFFAOYSA-N 1-(1,3-dimethyl-5-oxo-4-phenylpyrazol-4-yl)-1-hydroxy-3,3-dimethylurea Chemical compound CN1N=C(C(C1=O)(C1=CC=CC=C1)N(C(=O)N(C)C)O)C QVYLSVMCFVNCNQ-UHFFFAOYSA-N 0.000 claims 1
- YFASDNLXYFDFSF-UHFFFAOYSA-N 1-(3,4-dimethyl-5-oxo-1-phenylpyrazol-4-yl)-1-hydroxy-3,3-dimethylurea Chemical compound CN(C(N(C1(C(=NN(C1=O)C1=CC=CC=C1)C)C)O)=O)C YFASDNLXYFDFSF-UHFFFAOYSA-N 0.000 claims 1
- BKFPUQUPKQLGAP-UHFFFAOYSA-N 1-hydroxy-3,3-dimethyl-1-(1,3,4-trimethyl-5-oxopyrazol-4-yl)urea Chemical compound CN(C(N(C1(C(=NN(C1=O)C)C)C)O)=O)C BKFPUQUPKQLGAP-UHFFFAOYSA-N 0.000 claims 1
- JYELFUBMAKTPIP-UHFFFAOYSA-N 1-hydroxy-3,3-dimethyl-1-(1,3,5-trimethyl-2,4,6-trioxo-1,3-diazinan-5-yl)urea Chemical compound ON(C(=O)N(C)C)C1(C(N(C(N(C1=O)C)=O)C)=O)C JYELFUBMAKTPIP-UHFFFAOYSA-N 0.000 claims 1
- FOPJCCXKYUJAEZ-UHFFFAOYSA-N 1-hydroxy-3,3-dimethyl-1-(3-methyl-2,4-dioxochromen-3-yl)urea Chemical compound ON(C(=O)N(C)C)C1(C(OC2=CC=CC=C2C1=O)=O)C FOPJCCXKYUJAEZ-UHFFFAOYSA-N 0.000 claims 1
- QAICXRWGBVPPSF-UHFFFAOYSA-N 1-hydroxy-3,3-dimethyl-1-(3-methyl-5-oxo-1,4-diphenylpyrazol-4-yl)urea Chemical compound ON(C(=O)N(C)C)C1(C(=NN(C1=O)C1=CC=CC=C1)C)C1=CC=CC=C1 QAICXRWGBVPPSF-UHFFFAOYSA-N 0.000 claims 1
- VXZKLGGILDMVOS-UHFFFAOYSA-N 1-hydroxy-3,3-dimethyl-1-(5-methyl-2,4,6-trioxo-1,3-diazinan-5-yl)urea Chemical compound ON(C(=O)N(C)C)C1(C(NC(NC1=O)=O)=O)C VXZKLGGILDMVOS-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 206010007556 Cardiac failure acute Diseases 0.000 claims 1
- 229920002785 Croscarmellose sodium Polymers 0.000 claims 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- WPXCAVXDBZJVKM-UHFFFAOYSA-N N-(1,3-dimethyl-5-oxo-4-phenylpyrazol-4-yl)-N-hydroxyacetamide Chemical compound CN1N=C(C(C1=O)(C1=CC=CC=C1)N(C(C)=O)O)C WPXCAVXDBZJVKM-UHFFFAOYSA-N 0.000 claims 1
- FMYRWDXEYLEURW-UHFFFAOYSA-N N-(1,3-dimethyl-5-oxo-4-phenylpyrazol-4-yl)-N-hydroxybenzamide Chemical compound CN1N=C(C(C1=O)(C1=CC=CC=C1)N(C(C1=CC=CC=C1)=O)O)C FMYRWDXEYLEURW-UHFFFAOYSA-N 0.000 claims 1
- CXIHFYKWRJHUQU-UHFFFAOYSA-N N-(3,4-dimethyl-5-oxo-1-phenylpyrazol-4-yl)-N-hydroxyacetamide Chemical compound ON(C(C)=O)C1(C(=NN(C1=O)C1=CC=CC=C1)C)C CXIHFYKWRJHUQU-UHFFFAOYSA-N 0.000 claims 1
- VEKCNWBQUNSTKY-UHFFFAOYSA-N N-[1,4-dimethyl-3-(4-methylsulfonylphenyl)-5-oxopyrazol-4-yl]-N-hydroxyacetamide Chemical compound CN1N=C(C(C1=O)(C)N(C(C)=O)O)C1=CC=C(C=C1)S(=O)(=O)C VEKCNWBQUNSTKY-UHFFFAOYSA-N 0.000 claims 1
- SJTSPUHGVCINSG-UHFFFAOYSA-N ON(C(=O)N(C)C)C1(C(=NN(C1=O)C)C)C(C)=NOC Chemical compound ON(C(=O)N(C)C)C1(C(=NN(C1=O)C)C)C(C)=NOC SJTSPUHGVCINSG-UHFFFAOYSA-N 0.000 claims 1
- AMYPVTRIXZCFCO-UHFFFAOYSA-N ON(C(=O)N(C)C)C1(C(=NN(C1=O)C1=CC=CC=C1)C)C(C)=NOC Chemical compound ON(C(=O)N(C)C)C1(C(=NN(C1=O)C1=CC=CC=C1)C)C(C)=NOC AMYPVTRIXZCFCO-UHFFFAOYSA-N 0.000 claims 1
- LGQLTLIFTCFOPT-UHFFFAOYSA-N ON(C(=O)N(C)C)C1(C(N(C(N(C1=O)C)=O)C)=O)C(C)=NOC Chemical compound ON(C(=O)N(C)C)C1(C(N(C(N(C1=O)C)=O)C)=O)C(C)=NOC LGQLTLIFTCFOPT-UHFFFAOYSA-N 0.000 claims 1
- HBMKYFYTPPZRAB-UHFFFAOYSA-N ON(C(=O)N(C)C)C1(C(NC(NC1=O)=O)=O)C(C)=NOC Chemical compound ON(C(=O)N(C)C)C1(C(NC(NC1=O)=O)=O)C(C)=NOC HBMKYFYTPPZRAB-UHFFFAOYSA-N 0.000 claims 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229960005168 croscarmellose Drugs 0.000 claims 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 claims 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 229960001375 lactose Drugs 0.000 claims 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims 1
- 239000008108 microcrystalline cellulose Substances 0.000 claims 1
- 229940016286 microcrystalline cellulose Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562185310P | 2015-06-26 | 2015-06-26 | |
| US62/185,310 | 2015-06-26 | ||
| PCT/US2016/039453 WO2016210392A1 (en) | 2015-06-26 | 2016-06-25 | N-substituted hydroxamic acids with carbon-based leaving groups as efficient hno donors and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018520145A JP2018520145A (ja) | 2018-07-26 |
| JP2018520145A5 true JP2018520145A5 (https=) | 2019-07-04 |
| JP6820015B2 JP6820015B2 (ja) | 2021-01-27 |
Family
ID=56409199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017567124A Active JP6820015B2 (ja) | 2015-06-26 | 2016-06-25 | 効率的ｈｎｏドナーとしての炭素系脱離基を有するｎ−置換ヒドロキサム酸およびその使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10583141B2 (https=) |
| EP (1) | EP3313831B1 (https=) |
| JP (1) | JP6820015B2 (https=) |
| CN (1) | CN107922371B (https=) |
| ES (1) | ES2871079T3 (https=) |
| HK (1) | HK1254957A1 (https=) |
| WO (1) | WO2016210392A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10723704B2 (en) | 2015-10-19 | 2020-07-28 | Cardioxyl Pharmaceuticals, Inc. | Pyrazolone derivatives as nitroxyl donors |
| KR20180070672A (ko) | 2015-10-19 | 2018-06-26 | 카르디옥실 파마슈티칼스 인코포레이티드 | 니트록실 공여자로서의 n-히드록실술폰아미드 유도체 |
| EP3490975B1 (en) * | 2016-07-28 | 2021-05-05 | The Johns Hopkins University | O-substituted hydroxamic acids |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8030356B2 (en) * | 2006-03-17 | 2011-10-04 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
| AU2010328234B2 (en) | 2009-12-07 | 2016-05-12 | Cardioxyl Pharmaceuticals, Inc. | N-acyloxysulfonamide and N-hydroxy-N-acylsulfonamide derivatives |
| CN105130855B (zh) | 2009-12-07 | 2018-05-25 | 约翰斯霍普金斯大学 | 二酰基化的羟基胺衍生物及其用途 |
| JP6177246B2 (ja) | 2011-10-17 | 2017-08-09 | ザ・ジョンズ・ホプキンス・ユニバーシティ | ヒドロキシルアミンで置換された、ｈｎｏ供与体としてのメルドラム酸、バルビツール酸、及びピラゾロンの誘導体 |
| EP3148972B1 (en) | 2014-05-27 | 2019-08-21 | Cardioxyl Pharmaceuticals, Inc. | Pyrazolone derivatives as nitroxyl donors |
| WO2015183838A1 (en) | 2014-05-27 | 2015-12-03 | The Johns Hopkins University | N-hydroxylamino-barbituric acid derivatives as nitroxyl donors |
-
2016
- 2016-06-25 US US15/738,932 patent/US10583141B2/en active Active
- 2016-06-25 HK HK18114062.4A patent/HK1254957A1/zh unknown
- 2016-06-25 WO PCT/US2016/039453 patent/WO2016210392A1/en not_active Ceased
- 2016-06-25 ES ES16738303T patent/ES2871079T3/es active Active
- 2016-06-25 EP EP16738303.3A patent/EP3313831B1/en active Active
- 2016-06-25 JP JP2017567124A patent/JP6820015B2/ja active Active
- 2016-06-25 CN CN201680048966.XA patent/CN107922371B/zh not_active Expired - Fee Related
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