MX2012006349A - Derivados de n-aciloxisulfonamida y n-hidroxi-n-acilsulfonamida. - Google Patents
Derivados de n-aciloxisulfonamida y n-hidroxi-n-acilsulfonamida.Info
- Publication number
- MX2012006349A MX2012006349A MX2012006349A MX2012006349A MX2012006349A MX 2012006349 A MX2012006349 A MX 2012006349A MX 2012006349 A MX2012006349 A MX 2012006349A MX 2012006349 A MX2012006349 A MX 2012006349A MX 2012006349 A MX2012006349 A MX 2012006349A
- Authority
- MX
- Mexico
- Prior art keywords
- sulfonamido
- methanesulfonylbenzene
- carbonyl
- alkyl
- tert
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 282
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 92
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 85
- 201000010099 disease Diseases 0.000 claims abstract description 80
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims abstract description 70
- 208000002815 pulmonary hypertension Diseases 0.000 claims abstract description 60
- 208000028867 ischemia Diseases 0.000 claims abstract description 49
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 23
- 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 21
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 16
- -1 -OH Chemical group 0.000 claims description 367
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 151
- 125000000217 alkyl group Chemical group 0.000 claims description 133
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims description 132
- 125000003118 aryl group Chemical group 0.000 claims description 101
- 125000001424 substituent group Chemical group 0.000 claims description 74
- 206010019280 Heart failures Diseases 0.000 claims description 67
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 67
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 63
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 62
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 40
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 26
- 230000002861 ventricular Effects 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- XZHMDPRDCFAWOM-UHFFFAOYSA-N [(2-bromophenyl)sulfonylamino] acetate Chemical compound CC(=O)ONS(=O)(=O)C1=CC=CC=C1Br XZHMDPRDCFAWOM-UHFFFAOYSA-N 0.000 claims description 16
- 238000001727 in vivo Methods 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 230000001684 chronic effect Effects 0.000 claims description 11
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 230000004044 response Effects 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 7
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 7
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 6
- WNAYHYYKFCTBOP-UHFFFAOYSA-N [(2-methylsulfonylphenyl)sulfonylamino] acetate Chemical compound CC(=O)ONS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O WNAYHYYKFCTBOP-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
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- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010007556 Cardiac failure acute Diseases 0.000 claims description 4
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- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
- 230000003205 diastolic effect Effects 0.000 claims description 3
- DYXBVIGPQSCWEW-UHFFFAOYSA-N methanesulfonamido 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)ONS(C)(=O)=O DYXBVIGPQSCWEW-UHFFFAOYSA-N 0.000 claims description 3
- 235000013772 propylene glycol Nutrition 0.000 claims description 3
- 229960004063 propylene glycol Drugs 0.000 claims description 3
- ZBONBGOYILUGCL-UHFFFAOYSA-N 2,2-dimethylpropanoate Chemical compound CC(C)([CH2+])C([O-])=O ZBONBGOYILUGCL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 2
- UFCYGERRSSLKPZ-UHFFFAOYSA-N [(2,6-dibromophenyl)sulfonylamino] acetate Chemical compound CC(=O)ONS(=O)(=O)C1=C(Br)C=CC=C1Br UFCYGERRSSLKPZ-UHFFFAOYSA-N 0.000 claims description 2
- QIORGWUPWAYBLL-UHFFFAOYSA-N [(2,6-dichlorophenyl)sulfonylamino] acetate Chemical compound CC(=O)ONS(=O)(=O)C1=C(Cl)C=CC=C1Cl QIORGWUPWAYBLL-UHFFFAOYSA-N 0.000 claims description 2
- DHFSBZQIORGBND-UHFFFAOYSA-N benzenesulfonamido 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ONS(=O)(=O)C1=CC=CC=C1 DHFSBZQIORGBND-UHFFFAOYSA-N 0.000 claims description 2
- OLCRVFDIRAUCIR-UHFFFAOYSA-N n-(2,6-dichlorophenyl)sulfonyl-n-hydroxy-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)N(O)S(=O)(=O)C1=C(Cl)C=CC=C1Cl OLCRVFDIRAUCIR-UHFFFAOYSA-N 0.000 claims description 2
- QAMDJRGYVUMKKQ-UHFFFAOYSA-N n-(2-bromophenyl)sulfonyl-n-hydroxymorpholine-4-carboxamide Chemical compound C=1C=CC=C(Br)C=1S(=O)(=O)N(O)C(=O)N1CCOCC1 QAMDJRGYVUMKKQ-UHFFFAOYSA-N 0.000 claims description 2
- XUYIURFFRZSRMO-UHFFFAOYSA-N n-(benzenesulfonyl)-n-hydroxybenzamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(O)C(=O)C1=CC=CC=C1 XUYIURFFRZSRMO-UHFFFAOYSA-N 0.000 claims description 2
- 206010024119 Left ventricular failure Diseases 0.000 claims 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 206010060953 Ventricular failure Diseases 0.000 claims 2
- CTUHKGUSLCEPIL-UHFFFAOYSA-N 1-[4-(2-methylsulfonylphenyl)piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CC=C1S(C)(=O)=O CTUHKGUSLCEPIL-UHFFFAOYSA-N 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- YSZFVSBSWJNLHT-UHFFFAOYSA-N [(2,6-dichlorophenyl)sulfonylamino] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ONS(=O)(=O)C1=C(Cl)C=CC=C1Cl YSZFVSBSWJNLHT-UHFFFAOYSA-N 0.000 claims 1
- OBWSQWLCPBELGH-UHFFFAOYSA-N [(2,6-dichlorophenyl)sulfonylamino] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)ONS(=O)(=O)C1=C(Cl)C=CC=C1Cl OBWSQWLCPBELGH-UHFFFAOYSA-N 0.000 claims 1
- NDHQSFGCRNVQTA-UHFFFAOYSA-N [(2-bromophenyl)sulfonylamino] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)ONS(=O)(=O)C1=CC=CC=C1Br NDHQSFGCRNVQTA-UHFFFAOYSA-N 0.000 claims 1
- ZNLZOANNQUBOBS-UHFFFAOYSA-N [(2-methylsulfonylphenyl)sulfonylamino] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)ONS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ZNLZOANNQUBOBS-UHFFFAOYSA-N 0.000 claims 1
- VUAGRVXDRQUGAA-UHFFFAOYSA-N [(2-methylsulfonylphenyl)sulfonylamino] 2-methylpropanoate Chemical compound CC(C)C(=O)ONS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O VUAGRVXDRQUGAA-UHFFFAOYSA-N 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
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Classifications
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
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- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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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 |
US9181213B2 (en) | 2011-10-17 | 2015-11-10 | The Johns Hopkins University | Meldrum's acid, barbituric acid and pyrazolone derivatives substituted with hydroxylamine as HNO donors |
US9676708B2 (en) * | 2012-11-01 | 2017-06-13 | The Johns Hopkins University | Controlled HNO release through intramolecular cyclization-elimination |
BR112015017251B1 (pt) | 2013-01-18 | 2021-10-26 | Cardioxyl Pharmaceuticals, Inc. | Composições farmacêuticas compreendendo doadores de nitroxil, misturas e usos das referidas composições farmacêuticas |
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JP6957459B2 (ja) * | 2015-10-19 | 2021-11-02 | カルディオキシル ファーマシューティカルズ,インク. | ニトロキシルドナーとしてのn−ヒドロキシルスルホンアミド誘導体 |
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JP4783657B2 (ja) * | 2006-03-27 | 2011-09-28 | 富士フイルム株式会社 | ポジ型レジスト組成物及び該組成物を用いたパターン形成方法 |
JP2009533457A (ja) | 2006-04-13 | 2009-09-17 | ウェイク・フォレスト・ユニヴァーシティ・ヘルス・サイエンシズ | C−ニトロソから誘導されるニトロキシル供与体 |
AU2008304200B2 (en) * | 2007-09-26 | 2013-12-19 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
HUE030372T2 (en) | 2008-05-07 | 2017-05-29 | Cardioxyl Pharmaceuticals Inc | New nitroso compounds as nitroxyl donors and methods for their use |
WO2011063339A1 (en) * | 2009-11-23 | 2011-05-26 | Cardioxyl Pharmaceuticals, Inc. | Nitroxyl donors for the treatment of pulmonary hypertension |
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 |
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2010
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- 2010-12-07 CN CN201610319052.4A patent/CN105919987B/zh not_active Expired - Fee Related
- 2010-12-07 MX MX2012006349A patent/MX2012006349A/es not_active Application Discontinuation
- 2010-12-07 EP EP10793381.4A patent/EP2509941B1/en not_active Not-in-force
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- 2010-12-07 ES ES10793381T patent/ES2719101T3/es active Active
- 2010-12-07 CA CA2782110A patent/CA2782110A1/en not_active Abandoned
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2014
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2015
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2016
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WO2011071951A3 (en) | 2012-03-29 |
US20140235636A1 (en) | 2014-08-21 |
CN102753520B (zh) | 2016-06-08 |
US20180050985A1 (en) | 2018-02-22 |
IN2012DN05025A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-10-23 |
EP2509941A2 (en) | 2012-10-17 |
CN102753520A (zh) | 2012-10-24 |
AU2016206369B2 (en) | 2018-01-18 |
AU2010328234B2 (en) | 2016-05-12 |
ES2719101T3 (es) | 2019-07-08 |
JP5826762B2 (ja) | 2015-12-02 |
AU2016206369A1 (en) | 2016-08-11 |
JP2013512962A (ja) | 2013-04-18 |
CN105919987A (zh) | 2016-09-07 |
US20160046570A1 (en) | 2016-02-18 |
US20110144067A1 (en) | 2011-06-16 |
EP2509941B1 (en) | 2019-01-23 |
WO2011071951A2 (en) | 2011-06-16 |
JP2016094394A (ja) | 2016-05-26 |
CA2782110A1 (en) | 2011-06-16 |
CN105919987B (zh) | 2020-04-03 |
AU2010328234A1 (en) | 2012-06-14 |
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