ES2655942T3 - Sal de colina de un compuesto anti-inflamatorio de ciclobutenodiona sustituida - Google Patents
Sal de colina de un compuesto anti-inflamatorio de ciclobutenodiona sustituida Download PDFInfo
- Publication number
- ES2655942T3 ES2655942T3 ES12780535.6T ES12780535T ES2655942T3 ES 2655942 T3 ES2655942 T3 ES 2655942T3 ES 12780535 T ES12780535 T ES 12780535T ES 2655942 T3 ES2655942 T3 ES 2655942T3
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- amino
- chloro
- cyclobut
- dioxo
- hydroxy
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- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- 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
- C07C317/34—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 having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/36—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 having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/18—Sulfonamides
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C311/48—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 having nitrogen atoms of sulfonamide groups further bound to another hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
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- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161530516P | 2011-09-02 | 2011-09-02 | |
| US201161530516P | 2011-09-02 | ||
| PCT/IB2012/054502 WO2013030803A1 (en) | 2011-09-02 | 2012-08-31 | Choline salt of an anti - inflammatory substituted cyclobutenedione compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2655942T3 true ES2655942T3 (es) | 2018-02-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12780535.6T Active ES2655942T3 (es) | 2011-09-02 | 2012-08-31 | Sal de colina de un compuesto anti-inflamatorio de ciclobutenodiona sustituida |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9018261B2 (https=) |
| EP (2) | EP3287438A1 (https=) |
| JP (3) | JP2014529621A (https=) |
| KR (1) | KR102024955B1 (https=) |
| CN (1) | CN103842330B (https=) |
| BR (1) | BR112014004963A2 (https=) |
| CA (1) | CA2846510C (https=) |
| EA (1) | EA201490552A1 (https=) |
| ES (1) | ES2655942T3 (https=) |
| HU (1) | HUE035751T2 (https=) |
| IN (1) | IN2014DN02346A (https=) |
| MX (1) | MX359259B (https=) |
| NO (1) | NO2679622T3 (https=) |
| PL (1) | PL2760821T3 (https=) |
| PT (1) | PT2760821T (https=) |
| SI (1) | SI2760821T1 (https=) |
| WO (1) | WO2013030803A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA103198C2 (en) | 2008-08-04 | 2013-09-25 | Новартис Аг | Squaramide derivatives as cxcr2 antagonists |
| EP2764866A1 (en) | 2013-02-07 | 2014-08-13 | IP Gesellschaft für Management mbH | Inhibitors of nedd8-activating enzyme |
| TWI724056B (zh) | 2015-11-19 | 2021-04-11 | 美商卡默森屈有限公司 | Ｃｘｃｒ２抑制劑 |
| TWI734715B (zh) | 2015-11-19 | 2021-08-01 | 美商卡默森屈有限公司 | 趨化因子受體調節劑 |
| TW201922291A (zh) | 2017-11-16 | 2019-06-16 | 瑞士商諾華公司 | 組合療法 |
| IL275839B2 (en) | 2018-01-08 | 2024-02-01 | Chemocentryx Inc | Methods for the treatment of generalized abscess psoriasis using a CCR6 or CXCR2 antagonist |
| AR116109A1 (es) | 2018-07-10 | 2021-03-31 | Novartis Ag | Derivados de 3-(5-amino-1-oxoisoindolin-2-il)piperidina-2,6-diona y usos de los mismos |
| KR20210106437A (ko) | 2018-12-20 | 2021-08-30 | 노파르티스 아게 | 3-(1-옥소이소인돌린-2-일)피페리딘-2,6-디온 유도체를 포함하는 투약 요법 및 약학적 조합물 |
| CN113490528B (zh) | 2019-02-15 | 2024-12-03 | 诺华股份有限公司 | 3-(1-氧代-5-(哌啶-4-基)异吲哚啉-2-基)哌啶-2,6-二酮衍生物及其用途 |
| EP3924055B1 (en) | 2019-02-15 | 2024-04-03 | Novartis AG | Substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
| MX2022007759A (es) | 2019-12-20 | 2022-07-19 | Novartis Ag | Combinacion del anticuerpo anti tim-3 mbg453 y anticuerpo anti tgf-beta nis793, con o sin decitabina o el anticuerpo anti pd-1 spartalizumab, para el tratamiento de mielofibrosis y sindrome mielodisplasico. |
| SI3965742T1 (sl) * | 2020-04-24 | 2023-10-30 | Dr. Falk Pharma Gmbh | Sistemska formulacija piridinonskega derivata za bolezni, povezane s tg2 |
| CN115916199A (zh) | 2020-06-23 | 2023-04-04 | 诺华股份有限公司 | 包含3-(1-氧代异吲哚啉-2-基)哌啶-2,6-二酮衍生物的给药方案 |
| US20230271940A1 (en) | 2020-08-03 | 2023-08-31 | Novartis Ag | Heteroaryl substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
| TW202304979A (zh) | 2021-04-07 | 2023-02-01 | 瑞士商諾華公司 | 抗ＴＧＦβ抗體及其他治療劑用於治療增殖性疾病之用途 |
| AR125874A1 (es) | 2021-05-18 | 2023-08-23 | Novartis Ag | Terapias de combinación |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5506252A (en) | 1993-11-17 | 1996-04-09 | American Home Products Corporation | Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones |
| AU686896B2 (en) | 1994-11-16 | 1998-02-12 | American Home Products Corporation | Diaminocyclobutene-3,4-diones |
| AU6250298A (en) | 1997-01-30 | 1998-08-25 | American Home Products Corporation | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones |
| US5840764A (en) | 1997-01-30 | 1998-11-24 | American Home Products Corporation | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones |
| US6166050A (en) | 1998-12-14 | 2000-12-26 | American Home Products Corporation | 3,4-diamino-3-cyclobutene-1,2-dione derivatives which inhibit leukocyte adhesion mediated by VLA-4 |
| FR2815345B1 (fr) | 2000-10-12 | 2002-12-13 | Servier Lab | Nouveaux derives de cyclobutene-dione, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB0028844D0 (en) | 2000-11-27 | 2001-01-10 | Celltech Chiroscience Ltd | Chemical compounds |
| US20040048897A1 (en) | 2001-01-16 | 2004-03-11 | Mccleland Brent | Il-8 receptor antagonists |
| DE60230722D1 (de) | 2001-01-16 | 2009-02-26 | Smithkline Beecham Corp | Il-8-rezeptor-antagonisten |
| US20030175349A1 (en) * | 2001-01-30 | 2003-09-18 | Council Of Scientific And Industrial Research | Pharmaceutical compostion for extended/sustained release of a therapeutically active ingredient |
| WO2002062761A1 (en) | 2001-02-07 | 2002-08-15 | Abbott Laboratories | Aminal diones as potassium channel openers |
| CZ20032639A3 (cs) | 2001-03-30 | 2004-04-14 | Smithkline Beecham Corporation | Způsoby přípravy sloučenin obsahujících fenol |
| US7132445B2 (en) | 2001-04-16 | 2006-11-07 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| US20040106794A1 (en) | 2001-04-16 | 2004-06-03 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| PL208928B1 (pl) | 2001-04-16 | 2011-06-30 | Pharmacopeia | 3, 4-di-podstawione cyklobuten-1, 2-diony jako ligandy receptora CXC chemokiny |
| US20040097547A1 (en) | 2001-04-16 | 2004-05-20 | Taveras Arthur G. | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| WO2003000245A1 (en) | 2001-06-22 | 2003-01-03 | Poseidon Pharmaceuticals A/S | Compounds for use in disorders associated with mast cell or basophil activity |
| US20040053953A1 (en) | 2002-03-18 | 2004-03-18 | Schering Corporation | Treatment of chemokine mediated diseases |
| JP2009513512A (ja) * | 2003-07-09 | 2009-04-02 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | メロキシカムを含む組成物 |
| AU2005210504B2 (en) | 2004-01-30 | 2009-01-08 | Merck Sharp & Dohme Corp. | Crystalline polymorphs of a CXC-chemokine receptor ligand |
| EP1718303A4 (en) * | 2004-02-10 | 2010-09-01 | Santarus Inc | COMBINATION OF INHIBITOR OF PROTON PUMP, BUFFER AND NON-STEROIDAL ANTI-INFLAMMATORY DRUG |
| US7635694B2 (en) | 2004-02-27 | 2009-12-22 | Schering Corporation | Cyclobutenedione-containing compounds as inhibitors of hepatitis C virus NS3 serine protease |
| GB0407908D0 (en) * | 2004-04-07 | 2004-05-12 | Univ York | Ionic liquids |
| DE102004046492A1 (de) | 2004-09-23 | 2006-03-30 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| EP1674457B1 (en) | 2004-12-23 | 2009-06-03 | GPC Biotech AG | Derivatives of squaric acid with anti-proliferative activity |
| DE102005001053A1 (de) | 2005-01-07 | 2006-07-20 | Merck Patent Gmbh | Quadratsäurederivate |
| US20100130642A1 (en) | 2005-02-10 | 2010-05-27 | Wacker Chemie Ag | Lacquers containing particles with protected isocyanate groups |
| EP1853583B1 (en) | 2005-02-16 | 2011-09-07 | Schering Corporation | Amine-linked pyridyl and phenyl substituted piperazine-piperidines with cxcr3 antagonist activity |
| DE102005035742A1 (de) | 2005-07-29 | 2007-02-01 | Merck Patent Gmbh | Quadratsäurederivate II |
| DE102005035741A1 (de) | 2005-07-29 | 2007-02-08 | Merck Patent Gmbh | Quadratsäurederivate |
| AR061829A1 (es) | 2006-07-07 | 2008-09-24 | Schering Corp | Ciclobuten-1, 2-dionas 3,4-di sustituidas como ligandos de receptores de quimiocinas cxc |
| US8450348B2 (en) | 2007-02-21 | 2013-05-28 | Forma Tm, Llc | Derivatives of squaric acid with anti-proliferative activity |
| AU2008223348A1 (en) | 2007-03-07 | 2008-09-12 | Alantos Pharmaceuticals Holding, Inc. | Metalloprotease inhibitors containing a heterocyclic moiety |
| ES2386489T3 (es) | 2007-06-06 | 2012-08-21 | Novartis Ag | Compuestos ciclobutanediona sustituidos anti-inflamatorios |
| WO2009005801A1 (en) | 2007-07-03 | 2009-01-08 | Schering Corporation | Process and intermediates for the synthesis of 1,2-substituted 3,4-dioxo-1-cyclobutene compounds |
| WO2009005802A1 (en) | 2007-07-05 | 2009-01-08 | Schering Corporation | Process for controlled crystal size in 1,2-substituted 3,4-dioxo-1-cyclobutene compounds |
| WO2009012375A2 (en) | 2007-07-19 | 2009-01-22 | Wyeth | Squarate kinase inhibitors |
| US20110009482A1 (en) | 2007-12-04 | 2011-01-13 | Schering Corporation | Methods of treating copd |
| MX2010006421A (es) | 2007-12-10 | 2010-06-25 | Novartis Ag | Compuestos organicos. |
| US20110305768A1 (en) * | 2008-07-01 | 2011-12-15 | The Johns Hopkins University | Quick-dissolving oral thin film for targeted delivery of therapeutic agents |
| TWI454476B (zh) | 2008-07-08 | 2014-10-01 | Tibotec Pharm Ltd | 用作ｃ型肝炎病毒抑制劑之巨環吲哚衍生物 |
| UA103198C2 (en) * | 2008-08-04 | 2013-09-25 | Новартис Аг | Squaramide derivatives as cxcr2 antagonists |
| UA107183C2 (uk) | 2008-08-04 | 2014-12-10 | Феніламіно-ізонікотинамідні сполуки, їх застосування, фармацевтична композиція, що їх містить, та спосіб лікування гіперпроліферативних захворювань | |
| EP2376065A2 (en) * | 2008-11-14 | 2011-10-19 | Portola Pharmaceuticals, Inc. | Solid composition for controlled release of ionizable active agents with poor aqueous solubility at low ph and methods of use thereof |
| WO2010063802A1 (en) | 2008-12-05 | 2010-06-10 | Novartis Ag | 3, 4-di-substituted cyclobutene- 1, 2 -diones as cxcr2 receptor antagonists |
| WO2010091543A1 (en) | 2009-02-10 | 2010-08-19 | Merck Sharp & Dohme Corp. | Novel hydrazino-cyclobut-3-ene-1, 2-dione derivatives as cxcr2 antagonists |
-
2012
- 2012-08-31 HU HUE12780535A patent/HUE035751T2/hu unknown
- 2012-08-31 EA EA201490552A patent/EA201490552A1/ru unknown
- 2012-08-31 CA CA2846510A patent/CA2846510C/en not_active Expired - Fee Related
- 2012-08-31 KR KR1020147008317A patent/KR102024955B1/ko not_active Expired - Fee Related
- 2012-08-31 SI SI201231173T patent/SI2760821T1/en unknown
- 2012-08-31 CN CN201280047528.3A patent/CN103842330B/zh not_active Expired - Fee Related
- 2012-08-31 PT PT127805356T patent/PT2760821T/pt unknown
- 2012-08-31 WO PCT/IB2012/054502 patent/WO2013030803A1/en not_active Ceased
- 2012-08-31 JP JP2014527801A patent/JP2014529621A/ja active Pending
- 2012-08-31 MX MX2014002492A patent/MX359259B/es active IP Right Grant
- 2012-08-31 EP EP17191365.0A patent/EP3287438A1/en not_active Withdrawn
- 2012-08-31 ES ES12780535.6T patent/ES2655942T3/es active Active
- 2012-08-31 PL PL12780535T patent/PL2760821T3/pl unknown
- 2012-08-31 BR BR112014004963A patent/BR112014004963A2/pt active Search and Examination
- 2012-08-31 IN IN2346DEN2014 patent/IN2014DN02346A/en unknown
- 2012-08-31 US US14/241,306 patent/US9018261B2/en not_active Expired - Fee Related
- 2012-08-31 EP EP12780535.6A patent/EP2760821B1/en not_active Not-in-force
-
2013
- 2013-06-26 NO NO13173884A patent/NO2679622T3/no unknown
-
2016
- 2016-09-08 JP JP2016175348A patent/JP6612200B2/ja not_active Expired - Fee Related
-
2018
- 2018-07-19 JP JP2018135448A patent/JP2019001787A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017025081A (ja) | 2017-02-02 |
| EP2760821B1 (en) | 2017-10-11 |
| JP6612200B2 (ja) | 2019-11-27 |
| JP2019001787A (ja) | 2019-01-10 |
| PT2760821T (pt) | 2018-01-11 |
| MX2014002492A (es) | 2014-05-28 |
| US9018261B2 (en) | 2015-04-28 |
| CA2846510C (en) | 2019-10-22 |
| BR112014004963A2 (pt) | 2017-03-21 |
| IN2014DN02346A (https=) | 2015-05-15 |
| PL2760821T3 (pl) | 2018-04-30 |
| CN103842330B (zh) | 2016-10-19 |
| CN103842330A (zh) | 2014-06-04 |
| EP2760821A1 (en) | 2014-08-06 |
| MX359259B (es) | 2018-09-20 |
| EP3287438A1 (en) | 2018-02-28 |
| CA2846510A1 (en) | 2013-03-07 |
| EA201490552A1 (ru) | 2014-11-28 |
| KR20140059264A (ko) | 2014-05-15 |
| WO2013030803A1 (en) | 2013-03-07 |
| JP2014529621A (ja) | 2014-11-13 |
| HUE035751T2 (hu) | 2018-08-28 |
| NO2679622T3 (https=) | 2018-01-20 |
| US20140206768A1 (en) | 2014-07-24 |
| KR102024955B1 (ko) | 2019-09-24 |
| SI2760821T1 (en) | 2018-02-28 |
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