EA020114B1 - Производные арилсульфонамида в качестве ингибиторов матриксной металлопротеазы - Google Patents
Производные арилсульфонамида в качестве ингибиторов матриксной металлопротеазы Download PDFInfo
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- EA020114B1 EA020114B1 EA201001523A EA201001523A EA020114B1 EA 020114 B1 EA020114 B1 EA 020114B1 EA 201001523 A EA201001523 A EA 201001523A EA 201001523 A EA201001523 A EA 201001523A EA 020114 B1 EA020114 B1 EA 020114B1
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- Eurasian Patent Office
- Prior art keywords
- mmp
- chloro
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- alkyl
- benzenesulfonamide
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Classifications
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- C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
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Cited By (1)
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Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2009228765B2 (en) | 2008-03-24 | 2012-05-31 | Novartis Ag | Arylsulfonamide-based matrix metalloprotease inhibitors |
| CN102186820B (zh) | 2008-08-15 | 2013-08-28 | 乔治城大学 | Rassf1a表达和人癌细胞增殖的荧光调节剂 |
| CN102369205B (zh) | 2009-01-30 | 2014-10-29 | 武田药品工业株式会社 | 稠环化合物和其用途 |
| KR20120117905A (ko) * | 2010-01-28 | 2012-10-24 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 프로테아좀 활성을 향상시키는 조성물 및 방법 |
| HUE044867T2 (hu) | 2011-05-12 | 2019-11-28 | Proteostasis Therapeutics Inc | Proteosztázis szabályzók |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
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| KR101970505B1 (ko) * | 2012-12-26 | 2019-04-19 | (주)아모레퍼시픽 | 멜라닌 형성 억제제를 함유하는 미백용 피부 외용제 조성물 |
| US9849135B2 (en) | 2013-01-25 | 2017-12-26 | President And Fellows Of Harvard College | USP14 inhibitors for treating or preventing viral infections |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| CN108989649B (zh) | 2013-08-01 | 2021-03-19 | 核心光电有限公司 | 具有自动聚焦的纤薄多孔径成像系统及其使用方法 |
| PT3052485T (pt) | 2013-10-04 | 2021-10-22 | Infinity Pharmaceuticals Inc | Compostos heterocíclicos e suas utilizações |
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| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| WO2015074123A1 (en) * | 2013-11-25 | 2015-05-28 | Novogen ltd | Functionalised and substituted indoles as anti-cancer agents |
| MX382033B (es) | 2014-03-19 | 2025-03-13 | Infinity Pharmaceuticals Inc | Compuestos heterocíclicos para utilizarlos en el tratamiento de trastornos mediados por pi3k-gamma. |
| EA201650031A1 (ru) | 2014-05-15 | 2017-06-30 | Итеос Терапьютик | Производные пирролидин-2,5-диона, фармацевтические композиции и способы применения в качестве ингибиторов ido1 |
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| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| RU2711382C2 (ru) | 2014-12-03 | 2020-01-16 | Янссен Фармацевтика Нв | 6,7-ДИГИДРОПИРАЗОЛО[1,5-a]ПИРАЗИН-4(5H)-ОНОВЫЕ СОЕДИНЕНИЯ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ОТРИЦАТЕЛЬНЫХ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ MGLUR2 |
| EP3226915B1 (en) | 2014-12-03 | 2019-02-20 | Janssen Pharmaceutica NV | Radiolabelled mglur2 pet ligands |
| MX2017011951A (es) | 2015-03-17 | 2018-06-15 | Pfizer | Derivados sustituidos de indol 3 novedosos, composiciones farmaceuticas y metodos para uso. |
| US11053255B2 (en) | 2015-06-22 | 2021-07-06 | Georgetown University | Synthesis of mahanine and related compounds |
| EP3334733A1 (en) * | 2015-08-10 | 2018-06-20 | Pfizer Inc | 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| WO2017048702A1 (en) | 2015-09-14 | 2017-03-23 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| JP6929285B2 (ja) | 2015-12-18 | 2021-09-01 | ヤンセン ファーマシューティカ エヌ.ベー. | 放射性標識mGluR2/3PETリガンド |
| RS60981B1 (sr) | 2015-12-18 | 2020-11-30 | Janssen Pharmaceutica Nv | Radiooznačeni mglur2/3 pet ligandi |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN109666666B (zh) * | 2019-01-21 | 2021-03-05 | 天津科技大学 | 一种基于分子动力学的酶柔性分析提高肝素酶i热稳定性的突变体及其制备方法 |
| CN121270438B (zh) * | 2025-12-09 | 2026-04-28 | 荆楚理工学院 | 一种含磺酰脲结构化合物及其制备方法和应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB893072A (en) * | 1957-11-04 | 1962-04-04 | Geigy Ag J R | Benzophenone sulphonamides and process for producing same |
| US4156732A (en) * | 1977-06-21 | 1979-05-29 | Hoechst Aktiengesellschaft | Certain pharmaceutical sulfamoylbenzoyl benzofurans, benzothiophenes, and indoles |
| US4940793A (en) * | 1984-08-14 | 1990-07-10 | Ravizza S.P.A. | Pharmacologically active piperazino derivatives |
| US6277987B1 (en) * | 1998-02-04 | 2001-08-21 | Novartis Ag | Sulfonylamino acid and sulfonylamino hydroxamic acid derivatives |
| EP1288199A1 (en) * | 2000-04-28 | 2003-03-05 | Shionogi & Co., Ltd. | Mmp-12 inhibitors |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055905A (en) * | 1958-03-04 | 1962-09-25 | Geigy Chem Corp | New sulphamyl benzamides |
| US3055930A (en) * | 1959-02-26 | 1962-09-25 | Geigy Chem Corp | New benzophenone sulphonic acid amides |
| US3516992A (en) * | 1967-01-18 | 1970-06-23 | American Home Prod | 3-(2-amino-5-halo-,5-alkyl- and -5-alkoxybenzoyl) benzene sulfonamides |
| GB1524747A (en) | 1976-05-11 | 1978-09-13 | Ici Ltd | Polypeptide |
| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| ATE28864T1 (de) | 1982-07-23 | 1987-08-15 | Ici Plc | Amide-derivate. |
| GB8327256D0 (en) | 1983-10-12 | 1983-11-16 | Ici Plc | Steroid derivatives |
| US5093330A (en) | 1987-06-15 | 1992-03-03 | Ciba-Geigy Corporation | Staurosporine derivatives substituted at methylamino nitrogen |
| US4990523A (en) * | 1989-06-19 | 1991-02-05 | A. H. Robins Company, Incorporated | Treatment of chronic inflammatory joint disease with arylsulfonamides |
| US5010099A (en) | 1989-08-11 | 1991-04-23 | Harbor Branch Oceanographic Institution, Inc. | Discodermolide compounds, compositions containing same and method of preparation and use |
| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| GB9300059D0 (en) | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| TW225528B (cg-RX-API-DMAC7.html) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| DE69536015D1 (de) | 1995-03-30 | 2009-12-10 | Pfizer Prod Inc | Chinazolinone Derivate |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| US5843901A (en) | 1995-06-07 | 1998-12-01 | Advanced Research & Technology Institute | LHRH antagonist peptides |
| SI9620103A (sl) | 1995-07-06 | 1998-10-31 | Novartis Ag | Pirolopirimidini in postopki za njihovo pripravo |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| EA001595B1 (ru) | 1996-04-12 | 2001-06-25 | Варнер-Ламберт Компани | Необратимые ингибиторы тирозинкиназ |
| CA2258548C (en) | 1996-06-24 | 2005-07-26 | Pfizer Inc. | Phenylamino-substituted tricyclic derivatives for treatment of hyperproliferative diseases |
| AU716610B2 (en) | 1996-08-30 | 2000-03-02 | Novartis Ag | Method for producing epothilones, and intermediate products obtained during the production process |
| AU4141697A (en) | 1996-09-06 | 1998-03-26 | Obducat Ab | Method for anisotropic etching of structures in conducting materials |
| EP0954315A2 (en) | 1996-09-13 | 1999-11-10 | Sugen, Inc. | Use of quinazoline derivatives for the manufacture of a medicament in the treatment of hyperproliferative skin disorders |
| US6500983B2 (en) | 1996-10-02 | 2002-12-31 | Novartis Ag | Hydroxamic acid derivatives |
| EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
| ES2312695T3 (es) | 1996-11-18 | 2009-03-01 | Gesellschaft Fur Biotechnologische Forschung Mbh (Gbf) | Epotilones e y f. |
| US6441186B1 (en) | 1996-12-13 | 2002-08-27 | The Scripps Research Institute | Epothilone analogs |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| GB9721069D0 (en) | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Polymeric derivatives of camptothecin |
| US6410580B1 (en) | 1998-02-04 | 2002-06-25 | Novartis Ag | Sulfonylamino derivatives which inhibit matrix-degrading metalloproteinases |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| CA2322157C (en) | 1998-02-25 | 2012-05-29 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| PT1107964E (pt) | 1998-08-11 | 2010-06-11 | Novartis Ag | Derivados de isoquinolina com actividade inibidora da angiogénese |
| WO2000031247A2 (en) | 1998-11-20 | 2000-06-02 | Kosan Biosciences, Inc. | Recombinant methods and materials for producing epothilone and epothilone derivatives |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| SE0100569D0 (sv) * | 2001-02-20 | 2001-02-20 | Astrazeneca Ab | New compounds |
| TWI238824B (en) | 2001-05-14 | 2005-09-01 | Novartis Ag | 4-amino-5-phenyl-7-cyclobutyl-pyrrolo[2,3-d]pyrimidine derivatives |
| BR0209386A (pt) * | 2001-05-14 | 2004-07-06 | Novartis Ag | Derivados de sulfonamida |
| GB0119249D0 (en) | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| ES2377318T3 (es) | 2002-09-06 | 2012-03-26 | Cerulean Pharma Inc. | Polímeros a base de ciclodextrina para el suministro de los agentes terapéuticos enlazados covalentemente a ellos |
| AU2009228765B2 (en) | 2008-03-24 | 2012-05-31 | Novartis Ag | Arylsulfonamide-based matrix metalloprotease inhibitors |
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2009
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- 2009-03-23 KR KR1020107023599A patent/KR101673621B1/ko not_active Expired - Fee Related
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- 2009-03-23 EA EA201001523A patent/EA020114B1/ru not_active IP Right Cessation
- 2009-03-23 PT PT97244834T patent/PT2268612E/pt unknown
- 2009-03-23 BR BRPI0908603-0A patent/BRPI0908603A2/pt not_active Application Discontinuation
- 2009-03-23 PL PL09724483T patent/PL2268612T3/pl unknown
- 2009-03-23 WO PCT/EP2009/053390 patent/WO2009118292A1/en not_active Ceased
- 2009-03-23 CN CN200980118743.6A patent/CN102036953B/zh not_active Expired - Fee Related
- 2009-03-23 JP JP2011501191A patent/JP5490092B2/ja not_active Expired - Fee Related
- 2009-03-23 US US12/933,988 patent/US8222424B2/en active Active
- 2009-03-23 EP EP09724483.4A patent/EP2268612B1/en not_active Not-in-force
- 2009-03-23 MX MX2010010525A patent/MX2010010525A/es active IP Right Grant
- 2009-03-23 ES ES09724483.4T patent/ES2524259T3/es active Active
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2012
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- 2012-11-30 US US13/690,274 patent/US8975439B2/en active Active
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB893072A (en) * | 1957-11-04 | 1962-04-04 | Geigy Ag J R | Benzophenone sulphonamides and process for producing same |
| US4156732A (en) * | 1977-06-21 | 1979-05-29 | Hoechst Aktiengesellschaft | Certain pharmaceutical sulfamoylbenzoyl benzofurans, benzothiophenes, and indoles |
| US4940793A (en) * | 1984-08-14 | 1990-07-10 | Ravizza S.P.A. | Pharmacologically active piperazino derivatives |
| US6277987B1 (en) * | 1998-02-04 | 2001-08-21 | Novartis Ag | Sulfonylamino acid and sulfonylamino hydroxamic acid derivatives |
| EP1288199A1 (en) * | 2000-04-28 | 2003-03-05 | Shionogi & Co., Ltd. | Mmp-12 inhibitors |
Non-Patent Citations (3)
| Title |
|---|
| C. BOTRÉ, ET AL.: "Synthesis and inhibitory activity on carbonic anhydrase of some new sulpiride analogs studied by means of a new method". JOURNAL OF MEDICINAL CHEMISTRY, vol. 29, no. 10, October 1986 (1986-10), pages 1814-1820, XP002537896, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US ISSN: 0022-2623, table III; compounds 11, 13-15, 26 * |
| P. RUGGLI, ET AL.: "Die Säurechloride der m-Sulfo-benzoesaeure und ihre Umsetzungenmit Aminen und Phenolen". HELVETICA CHIMICA ACTA, 1941, pages 197-212, XP001024643, VERLAG HELVETICA CHIMICA ACTA, BASEL, CH ISSN: 0018-019X, page 211, lines 22-30 * |
| W.J. HUDAK, ET AL.: "Aminoalkenylbenzenesulphonamides with hypotensive and histamine-releasing properties". JOURNAL OF MEDICINAL CHEMISTRY, vol. 13, no. 5, September 1970 (1970-09), pages 895-900, XP002537940, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, ISSN: 0022-2623, compound 32 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12319698B2 (en) | 2018-06-27 | 2025-06-03 | Kineta, Inc. | Proteasome activity enhancing compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011517446A (ja) | 2011-06-09 |
| CA2719457A1 (en) | 2009-10-01 |
| PL2268612T3 (pl) | 2015-02-27 |
| AU2009228765B2 (en) | 2012-05-31 |
| AU2009228765A1 (en) | 2009-10-01 |
| CN102036953A (zh) | 2011-04-27 |
| US20150045398A1 (en) | 2015-02-12 |
| KR101673621B1 (ko) | 2016-11-07 |
| JP5490092B2 (ja) | 2014-05-14 |
| EP2268612A1 (en) | 2011-01-05 |
| PT2268612E (pt) | 2014-11-13 |
| ES2524259T3 (es) | 2014-12-04 |
| US9822092B2 (en) | 2017-11-21 |
| US20130096105A1 (en) | 2013-04-18 |
| US8222424B2 (en) | 2012-07-17 |
| KR20100127291A (ko) | 2010-12-03 |
| CA2719457C (en) | 2017-05-02 |
| MX2010010525A (es) | 2010-10-25 |
| US8362063B2 (en) | 2013-01-29 |
| BRPI0908603A2 (pt) | 2020-08-18 |
| US20110014186A1 (en) | 2011-01-20 |
| US8975439B2 (en) | 2015-03-10 |
| EA201001523A1 (ru) | 2011-06-30 |
| CN102036953B (zh) | 2015-05-06 |
| US20120258954A1 (en) | 2012-10-11 |
| EP2268612B1 (en) | 2014-08-20 |
| WO2009118292A1 (en) | 2009-10-01 |
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