JP2013511556A5 - - Google Patents
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- JP2013511556A5 JP2013511556A5 JP2012540154A JP2012540154A JP2013511556A5 JP 2013511556 A5 JP2013511556 A5 JP 2013511556A5 JP 2012540154 A JP2012540154 A JP 2012540154A JP 2012540154 A JP2012540154 A JP 2012540154A JP 2013511556 A5 JP2013511556 A5 JP 2013511556A5
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- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- composition according
- hydroxybenzenesulfonamide
- halo
- nitro
- 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.)
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- 239000008194 pharmaceutical composition Substances 0.000 claims 28
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- -1 N-hydroxylsulfonamidyl Chemical group 0.000 claims 6
- 208000002815 Pulmonary Hypertension Diseases 0.000 claims 6
- 206010024119 Left ventricular failure Diseases 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- JTMRAKAVHPQVLR-UHFFFAOYSA-N 2-bromo-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=CC=C1Br JTMRAKAVHPQVLR-UHFFFAOYSA-N 0.000 claims 2
- QVWABNGSRMHSSC-UHFFFAOYSA-N 2-fluoro-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=CC=C1F QVWABNGSRMHSSC-UHFFFAOYSA-N 0.000 claims 2
- UHLUYTLUWPLQIV-UHFFFAOYSA-N N-hydroxy-2-(trifluoromethyl)benzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=CC=C1C(F)(F)F UHLUYTLUWPLQIV-UHFFFAOYSA-N 0.000 claims 2
- RPCWSYAQEVLTEE-UHFFFAOYSA-N N-hydroxy-2-iodobenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=CC=C1I RPCWSYAQEVLTEE-UHFFFAOYSA-N 0.000 claims 2
- RZRWBKKAFHXNEQ-UHFFFAOYSA-N N-hydroxy-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NO RZRWBKKAFHXNEQ-UHFFFAOYSA-N 0.000 claims 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 2
- 201000010238 heart disease Diseases 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- ZRWVFIVDXWDXDB-UHFFFAOYSA-N 2,3-dichloro-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=CC(Cl)=C1Cl ZRWVFIVDXWDXDB-UHFFFAOYSA-N 0.000 claims 1
- PMCCDTRQTMOMDO-UHFFFAOYSA-N 2,4-dibromo-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=C(Br)C=C1Br PMCCDTRQTMOMDO-UHFFFAOYSA-N 0.000 claims 1
- XZXRZAJTPROFFJ-UHFFFAOYSA-N 2,4-difluoro-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=C(F)C=C1F XZXRZAJTPROFFJ-UHFFFAOYSA-N 0.000 claims 1
- NQRQXMMHKBZSFH-UHFFFAOYSA-N 2,6-dichloro-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=C(Cl)C=CC=C1Cl NQRQXMMHKBZSFH-UHFFFAOYSA-N 0.000 claims 1
- KYAYUXVCXCRWGE-UHFFFAOYSA-N 2-bromo-4-fluoro-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=C(F)C=C1Br KYAYUXVCXCRWGE-UHFFFAOYSA-N 0.000 claims 1
- KDAUHUPSWREKDU-UHFFFAOYSA-N 2-chloro-4-fluoro-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=C(F)C=C1Cl KDAUHUPSWREKDU-UHFFFAOYSA-N 0.000 claims 1
- CRGRKPVYYZZUHX-UHFFFAOYSA-N 2-chloro-N-hydroxy-4-(trifluoromethyl)benzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl CRGRKPVYYZZUHX-UHFFFAOYSA-N 0.000 claims 1
- BASKBTQCHRZHSH-UHFFFAOYSA-N 2-chloro-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=CC=C1Cl BASKBTQCHRZHSH-UHFFFAOYSA-N 0.000 claims 1
- SNDSZUKNUDOLGZ-UHFFFAOYSA-N 4-bromo-2-chloro-N-hydroxybenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=C(Br)C=C1Cl SNDSZUKNUDOLGZ-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000003037 Diastolic Heart Failure Diseases 0.000 claims 1
- YWZWWGLSOOIVSN-UHFFFAOYSA-N N-hydroxy-2,4,6-tri(propan-2-yl)benzenesulfonamide Chemical compound CC(C)C1=CC(C(C)C)=C(S(=O)(=O)NO)C(C(C)C)=C1 YWZWWGLSOOIVSN-UHFFFAOYSA-N 0.000 claims 1
- NBJISJHKYNUFIN-UHFFFAOYSA-N N-hydroxy-2,5-bis(trifluoromethyl)benzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(F)(F)F NBJISJHKYNUFIN-UHFFFAOYSA-N 0.000 claims 1
- SEBLDBIKKKKJMQ-UHFFFAOYSA-N N-hydroxy-2-nitro-4-(trifluoromethyl)benzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O SEBLDBIKKKKJMQ-UHFFFAOYSA-N 0.000 claims 1
- MGMDZPKSAJJKCS-UHFFFAOYSA-N N-hydroxy-2-phenylbenzenesulfonamide Chemical compound ONS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 MGMDZPKSAJJKCS-UHFFFAOYSA-N 0.000 claims 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 1
- 208000008253 Systolic Heart Failure Diseases 0.000 claims 1
- 210000003462 Veins Anatomy 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
Claims (28)
- 有効な量のニトロキシル供与体を含有する肺高血圧症の治療用医薬組成物。
- ニトロキシル供与体が、式Ｉ
Ｒ１は、Ｈであり；
Ｒ２は、Ｈであり；
Ｒ３、Ｒ４、Ｒ５、Ｒ６およびＲ７は、独立してＨ、ハロ、アルキルスルホニル、Ｎ−ヒドロキシルスルホンアミジル、パーハロアルキル、ニトロ、アリール、シアノ、アルコキシ、パーハロアルコキシ、アルキル、置換アリールオキシ、アルキルスルファニル、アルキルスルフィニル、ヘテロシクロアルキル、置換ヘテロシクロアルキル、ジアルキルアミノ、シクロアルコキシ、シクロアルキルスルファニル、アリールスルファニルおよびアリールスルフィニルから選択される、
請求項１に記載の医薬組成物。 - 有効な量が約１ｇ／ｋｇ／ｄ未満である、請求項２に記載の医薬組成物。
- 静脈内に投与される、請求項２または３に記載の医薬組成物。
- 経口的に投与される、請求項２または３に記載の医薬組成物。
- 吸入によって投与される、請求項２または３に記載の医薬組成物。
- ヒトに投与される、請求項２〜６のいずれか一項に記載の医薬組成物。
- 肺高血圧症が肺動脈高血圧症である、請求項２〜７のいずれか一項に記載の医薬組成物。
- 肺高血圧症が左心疾患による肺高血圧症である、請求項２〜７のいずれか一項に記載の医薬組成物。
- 左心疾患が左心不全である、請求項９に記載の医薬組成物。
- 左心不全が収縮心不全である、請求項１０に記載の医薬組成物。
- 左心不全が拡張心不全である、請求項１０に記載の医薬組成物。
- 左心不全が慢性的に、または急性的に非代償である、請求項１０に記載の医薬組成物。
- 肺高血圧症が慢性血栓塞栓性肺高血圧症である、請求項２〜７のいずれか一項に記載の医薬組成物。
- Ｒ３およびＲ７の一方は、Ｈ以外であり；
Ｒ３、Ｒ４、Ｒ５、Ｒ６およびＲ７の少なくとも１つは、ハロ以外であり；
Ｒ３またはＲ７の一方がハロであり、ハロではないＲ３またはＲ７がＨであり、Ｒ４またはＲ６の一方がハロであり、ハロではないＲ４またはＲ６がＨである場合には、Ｒ５はハロまたは水素以外であり；
Ｒ４、Ｒ５およびＲ６がＨであり、Ｒ３およびＲ７の一方がＨである場合には、ＨではないＲ３またはＲ７はニトロまたはアルキル以外であり；また
Ｒ４およびＲ６がＨであり、Ｒ３およびＲ７がアルキルである場合には、Ｒ５はアルキル以外である、
請求項２〜１４のいずれか一項に記載の医薬組成物。 - Ｒ３がハロ、アルキルスルホニル、パーハロアルキル、低級アルキル、ニトロまたはシアノである、
請求項２〜１４のいずれか一項に記載の医薬組成物。 - Ｒ３がハロ、アルキルスルホニル、パーハロアルキル、低級アルキル、ニトロまたはシアノであり；また
Ｒ４、Ｒ５、Ｒ６およびＲ７の少なくとも３つがＨである、
請求項２〜１４のいずれか一項に記載の医薬組成物。 - Ｒ３がハロ、アルキルスルホニル、パーハロアルキル、低級アルキル、ニトロまたはシアノであり；また
Ｒ４、Ｒ５、Ｒ６およびＲ７がＨである、
請求項２〜１４のいずれか一項に記載の医薬組成物。 - Ｒ３がハロ、メチルスルホニル、パーフルオロメチル、パーフルオロメトキシ、イソプロピル、ニトロまたはシアノである、請求項２〜１４のいずれか一項に記載の医薬組成物。
- Ｒ３がハロ、メチルスルホニル、パーフルオロメチル、パーフルオロメトキシ、イソプロピル、ニトロまたはシアノであり；また
Ｒ４、Ｒ５、Ｒ６およびＲ７の少なくとも３つがＨである、
請求項２〜１４のいずれか一項に記載の医薬組成物。 - Ｒ３がハロ、メチルスルホニル、パーフルオロメチル、パーフルオロメトキシ、イソプロピル、ニトロまたはシアノであり；また
Ｒ４、Ｒ５、Ｒ６およびＲ７がＨである、
請求項２〜１４のいずれか一項に記載の医薬組成物。 - 化合物が、以下のもの：
２，６−ジクロロ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−ブロモ−４−フルオロ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２，５−ジ−トリフルオロメチル−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−クロロ−４−フルオロ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２，３−ジクロロ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−クロロ−４−ブロモ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−ニトロ−４−トリフルオロメチル−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−ヨード−Ｎ−ヒドロキシベンゼンスルホンアミド；
Ｎ−ヒドロキシ−２−メタンスルホニルベンゼンスルホンアミド；
２，４−ジ−ブロモ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−クロロ−４−トリフルオロメチル−Ｎ−ヒドロキシベンゼンスルホンアミド；
２，４，６−トリ−イソプロピル−Ｎ−ヒドロキシベンゼンスルホンアミド；
２，４−ジ−フルオロ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−フルオロ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−ブロモ−Ｎ−ヒドロキシベンゼンスルホンアミド；
２−（トリフルオロメチル）−Ｎ−ヒドロキシベンゼンスルホンアミド；
Ｎ−ヒドロキシ−２−フェニルベンゼンスルホンアミド；および
その薬学的に許容し得る塩
から選択される、請求項２〜１４のいずれか一項に記載の医薬組成物。 - 化合物が２−ヨード−Ｎ−ヒドロキシベンゼンスルホンアミドである、請求項２〜１４のいずれか一項に記載の医薬組成物。
- 化合物がＮ−ヒドロキシ−２−メタンスルホニルベンゼンスルホンアミドである、請求項２〜１４のいずれか一項に記載の医薬組成物。
- 化合物が２−フルオロ−Ｎ−ヒドロキシベンゼンスルホンアミドである、請求項２〜１４のいずれか一項に記載の医薬組成物。
- 化合物が２−クロロ−Ｎ−ヒドロキシベンゼンスルホンアミドである、請求項２〜１４のいずれか一項に記載の医薬組成物。
- 化合物が２−ブロモ−Ｎ−ヒドロキシベンゼンスルホンアミドである、請求項２〜１４のいずれか一項に記載の医薬組成物。
- 化合物が２−（トリフルオロメチル）−Ｎ−ヒドロキシベンゼンスルホンアミドである、請求項２〜１４のいずれか一項に記載の医薬組成物。
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26369809P | 2009-11-23 | 2009-11-23 | |
| US61/263,698 | 2009-11-23 | ||
| US26412909P | 2009-11-24 | 2009-11-24 | |
| US61/264,129 | 2009-11-24 | ||
| PCT/US2010/057844 WO2011063400A1 (en) | 2009-11-23 | 2010-11-23 | Nitroxyl donors for the treatment of pulmonary hypertension |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016015102A Division JP2016128481A (ja) | 2009-11-23 | 2016-01-29 | 肺高血圧症の処置のためのニトロキシル供与体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013511556A JP2013511556A (ja) | 2013-04-04 |
| JP2013511556A5 true JP2013511556A5 (ja) | 2014-01-16 |
Family
ID=43513876
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012540154A Pending JP2013511556A (ja) | 2009-11-23 | 2010-11-23 | 肺高血圧症の処置のためのニトロキシル供与体 |
| JP2016015102A Pending JP2016128481A (ja) | 2009-11-23 | 2016-01-29 | 肺高血圧症の処置のためのニトロキシル供与体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016015102A Pending JP2016128481A (ja) | 2009-11-23 | 2016-01-29 | 肺高血圧症の処置のためのニトロキシル供与体 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US20110160200A1 (ja) |
| EP (1) | EP2504003B1 (ja) |
| JP (2) | JP2013511556A (ja) |
| CY (1) | CY1118603T1 (ja) |
| DK (1) | DK2504003T3 (ja) |
| ES (1) | ES2611852T3 (ja) |
| HR (1) | HRP20170183T1 (ja) |
| HU (1) | HUE032253T2 (ja) |
| LT (1) | LT2504003T (ja) |
| PL (1) | PL2504003T3 (ja) |
| PT (1) | PT2504003T (ja) |
| RS (1) | RS55697B1 (ja) |
| SI (1) | SI2504003T1 (ja) |
| SM (1) | SMT201700090B (ja) |
| WO (2) | WO2011063339A1 (ja) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2010328234B2 (en) * | 2009-12-07 | 2016-05-12 | Cardioxyl Pharmaceuticals, Inc. | N-acyloxysulfonamide and N-hydroxy-N-acylsulfonamide derivatives |
| 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 |
| HUE041861T2 (hu) | 2013-01-18 | 2019-06-28 | Cardioxyl Pharmaceuticals Inc | Nitroxil donorokat tartalmazó gyógyszerészeti kompozíciók |
| MX360455B (es) * | 2013-05-14 | 2018-11-01 | Active Biotech Ab | Derivados de n-(heteroaril)-sulfonamida utiles como inhibidores de s100. |
| WO2015109210A1 (en) | 2014-01-17 | 2015-07-23 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxymethanesulfonamide nitroxyl donors |
| WO2015183839A1 (en) | 2014-05-27 | 2015-12-03 | Cardioxyl Pharmaceuticals, Inc. | Pyrazolone derivatives as nitroxyl donors |
| US9464061B2 (en) | 2014-05-27 | 2016-10-11 | The Johns Hopkins University | N-hydroxylamino-barbituric acid derivatives |
| WO2017070084A1 (en) | 2015-10-19 | 2017-04-27 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as nitroxyl donors |
| CN108473439B (zh) | 2015-10-19 | 2022-03-15 | 卡尔迪奥克斯尔制药公司 | 作为硝酰基供体的吡唑啉酮衍生物 |
| JP7194436B2 (ja) | 2016-07-28 | 2022-12-22 | ザ ジョンズ ホプキンス ユニバーシティ | Ｏ－置換ヒドロキサム酸 |
| CA3049003A1 (en) | 2017-01-03 | 2018-07-12 | Cardioxyl Pharmaceuticals, Inc. | Method of administering nitroxyl donating compounds |
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2010
- 2010-11-22 WO PCT/US2010/057640 patent/WO2011063339A1/en active Application Filing
- 2010-11-22 US US12/951,900 patent/US20110160200A1/en not_active Abandoned
- 2010-11-23 SI SI201031332A patent/SI2504003T1/sl unknown
- 2010-11-23 LT LTEP10784416.9T patent/LT2504003T/lt unknown
- 2010-11-23 ES ES10784416.9T patent/ES2611852T3/es active Active
- 2010-11-23 DK DK10784416.9T patent/DK2504003T3/en active
- 2010-11-23 JP JP2012540154A patent/JP2013511556A/ja active Pending
- 2010-11-23 PL PL10784416T patent/PL2504003T3/pl unknown
- 2010-11-23 EP EP10784416.9A patent/EP2504003B1/en active Active
- 2010-11-23 WO PCT/US2010/057844 patent/WO2011063400A1/en active Application Filing
- 2010-11-23 RS RS20170138A patent/RS55697B1/sr unknown
- 2010-11-23 PT PT107844169T patent/PT2504003T/pt unknown
- 2010-11-23 HU HUE10784416A patent/HUE032253T2/en unknown
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2015
- 2015-04-24 US US14/696,319 patent/US20160081951A1/en not_active Abandoned
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2016
- 2016-01-29 JP JP2016015102A patent/JP2016128481A/ja active Pending
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2017
- 2017-02-03 HR HRP20170183TT patent/HRP20170183T1/hr unknown
- 2017-02-07 CY CY20171100169T patent/CY1118603T1/el unknown
- 2017-02-09 SM SM201700090T patent/SMT201700090B/it unknown
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