ES2535716T3 - Compuestos de 6-aminoisoquinolina y métodos para preparar los mismos - Google Patents
Compuestos de 6-aminoisoquinolina y métodos para preparar los mismos Download PDFInfo
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- ES2535716T3 ES2535716T3 ES12007093.3T ES12007093T ES2535716T3 ES 2535716 T3 ES2535716 T3 ES 2535716T3 ES 12007093 T ES12007093 T ES 12007093T ES 2535716 T3 ES2535716 T3 ES 2535716T3
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- alkyl
- aryl
- heteroaryl
- hydroxyl
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- 238000000034 method Methods 0.000 title description 6
- NGFCTYXFMDWFRQ-UHFFFAOYSA-N isoquinolin-6-amine Chemical class C1=NC=CC2=CC(N)=CC=C21 NGFCTYXFMDWFRQ-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 abstract description 12
- -1 C1-C4-alkyl-aryl Chemical group 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 125000001544 thienyl group Chemical group 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical class 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000002950 monocyclic group Chemical group 0.000 abstract 3
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
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- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- 125000003003 spiro group Chemical group 0.000 abstract 2
- 125000004001 thioalkyl group Chemical group 0.000 abstract 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- OXGBCSQEKCRCHN-UHFFFAOYSA-N octadecan-2-ol Chemical compound CCCCCCCCCCCCCCCCC(C)O OXGBCSQEKCRCHN-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
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- XEIOPEQGDSYOIH-MURFETPASA-N propan-2-yl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(C)C XEIOPEQGDSYOIH-MURFETPASA-N 0.000 description 1
- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- 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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Neurology (AREA)
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- Gastroenterology & Hepatology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US12/009,326 US8455514B2 (en) | 2008-01-17 | 2008-01-17 | 6-and 7-amino isoquinoline compounds and methods for making and using the same |
| US9326 | 2008-01-17 |
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| ES2535716T3 true ES2535716T3 (es) | 2015-05-14 |
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| ES12007092.5T Active ES2465572T3 (es) | 2008-01-17 | 2009-01-15 | Compuestos de 6-aminoisoquinolinas y métodos para preparar los mismos |
| ES09702189T Active ES2397928T3 (es) | 2008-01-17 | 2009-01-15 | Compuestos de 6- y 7-aminoisoquinolina y métodos para preparar y usar los mismos |
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| ES09702189T Active ES2397928T3 (es) | 2008-01-17 | 2009-01-15 | Compuestos de 6- y 7-aminoisoquinolina y métodos para preparar y usar los mismos |
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| ES2580108T3 (es) * | 2005-07-11 | 2016-08-19 | Aerie Pharmaceuticals, Inc | Compuestos de isoquinolina |
| ES2729424T3 (es) | 2006-09-20 | 2019-11-04 | Aerie Pharmaceuticals Inc | Inhibidores de Rho cinasa |
| US8455513B2 (en) | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
| US8455514B2 (en) | 2008-01-17 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-and 7-amino isoquinoline compounds and methods for making and using the same |
| US8450344B2 (en) * | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
| EP3828172A1 (en) | 2009-05-01 | 2021-06-02 | Aerie Pharmaceuticals, Inc. | Dual mechanism inhibitors for the treatment of disease |
| PT2657227T (pt) * | 2010-12-22 | 2016-08-01 | D Western Therapeutics Inst Inc | Novo derivado de isoquinolina substituída |
| US20140275160A1 (en) | 2013-03-15 | 2014-09-18 | Aerie Pharmaceuticals, Inc. | Combination therapy |
| JP6683686B2 (ja) | 2014-08-22 | 2020-04-22 | オークランド ユニサービシーズ リミティド | チャネル調節剤 |
| JP6832946B2 (ja) | 2015-11-17 | 2021-02-24 | アエリエ ファーマシューティカルズ インコーポレイテッド | キナーゼ阻害剤およびその中間体の調製方法 |
| US9643927B1 (en) | 2015-11-17 | 2017-05-09 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
| US10109932B2 (en) | 2016-04-20 | 2018-10-23 | Hubbell Incorporated | Electrical clamps |
| CN109640966A (zh) | 2016-08-31 | 2019-04-16 | 爱瑞制药公司 | 眼用组合物 |
| CN110337292A (zh) | 2017-02-28 | 2019-10-15 | 兴和株式会社 | 医药品 |
| JP7108596B2 (ja) | 2017-02-28 | 2022-07-28 | 興和株式会社 | 医薬 |
| EP3590514A4 (en) | 2017-02-28 | 2021-01-06 | Kowa Company, Ltd. | PHARMACEUTICAL PREPARATION |
| KR20190128657A (ko) | 2017-03-27 | 2019-11-18 | 코와 가부시키가이샤 | 의약 제제 |
| WO2018183911A1 (en) | 2017-03-31 | 2018-10-04 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| US10696638B2 (en) | 2017-12-26 | 2020-06-30 | Industrial Technology Research Institute | Compounds for inhibiting AGC kinase and pharmaceutical compositions comprising the same |
| US11427563B2 (en) | 2018-09-14 | 2022-08-30 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| US20220119350A1 (en) * | 2019-02-22 | 2022-04-21 | Glaukos Corporation | Compounds for the treatment of ocular disease |
Family Cites Families (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2623228C3 (de) * | 1976-05-24 | 1981-09-10 | Ludwig Merckle Kg Chem. Pharm. Fabrik, 7902 Blaubeuren | N-Acyl-substituierte Benzamide, Verfahren zu ihrer Herstellung und Arzneimittel, enthaltend solche Benzamide |
| US4456757A (en) * | 1981-03-20 | 1984-06-26 | Asahi Kasei Kogyo Kabushiki Kaisha | Isoquinolinesulfonyl derivatives and process for the preparation thereof |
| JPS5993054A (ja) * | 1982-11-18 | 1984-05-29 | Asahi Chem Ind Co Ltd | イソキノリンスルホン酸アミド誘導体 |
| DK8386A (da) | 1986-01-15 | 1987-07-09 | Tpo Pharmachim | Nye n-substituerede 1-benzyl-2-carbamoyltetrahydroisoquinoliner og fremgangsmaade til fremstilling af samme |
| US4911928A (en) | 1987-03-13 | 1990-03-27 | Micro-Pak, Inc. | Paucilamellar lipid vesicles |
| JPH01139528A (ja) * | 1987-11-24 | 1989-06-01 | Showa Denko Kk | 抗潰瘍剤 |
| EP0389995B1 (en) | 1989-03-28 | 1995-05-31 | Nisshin Flour Milling Co., Ltd. | Isoquinoline derivatives for the treatment of glaucoma or ocular hypertension |
| KR920008026A (ko) | 1990-10-24 | 1992-05-27 | 오노 화아마슈티칼 캄파니 리미팃드 | 이소퀴놀리논 유도체 또는 이의 무독성 산부가염 또는 이의 수화물, 이의 제조방법 및 이를 포함하는 약제 조성물 |
| JPH07504429A (ja) | 1992-03-12 | 1995-05-18 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５ＨＴ↓１ｃアンタゴニストとしてのインドール誘導体 |
| DE4332168A1 (de) * | 1993-02-22 | 1995-03-23 | Thomae Gmbh Dr K | Cyclische Derivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US6586425B2 (en) | 1996-02-21 | 2003-07-01 | Wisconsin Alumni Research Foundation | Cytoskeletal active agents for glaucoma therapy |
| US5798380A (en) | 1996-02-21 | 1998-08-25 | Wisconsin Alumni Research Foundation | Cytoskeletal active agents for glaucoma therapy |
| US5891646A (en) | 1997-06-05 | 1999-04-06 | Duke University | Methods of assaying receptor activity and constructs useful in such methods |
| WO2000077027A2 (en) | 1999-06-14 | 2000-12-21 | Tularik Limited | Serine protease inhibitors |
| US6720175B1 (en) | 1998-08-18 | 2004-04-13 | The Johns Hopkins University School Of Medicine | Nucleic acid molecule encoding homer 1B protein |
| US20020065296A1 (en) | 1999-01-13 | 2002-05-30 | Bayer Corporation | Heteroaryl ureas containing nitrogen hetero-atoms as p38 kinase inhibitors |
| AU5283800A (en) * | 1999-05-24 | 2000-12-12 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| WO2001037826A1 (en) * | 1999-11-26 | 2001-05-31 | Shionogi & Co., Ltd. | Npyy5 antagonists |
| MXPA02006474A (es) | 1999-12-28 | 2002-11-29 | Eisai Co Ltd | Compuestos heterociclicos que contienen sulfonamida. |
| YU54202A (sh) | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| HN2001000008A (es) | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| KR100767000B1 (ko) | 2000-02-03 | 2007-10-15 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 인테그린 발현 저해제 |
| US6362177B1 (en) | 2000-05-16 | 2002-03-26 | Teijin Limited | Cyclic amine derivatives and their use as drugs |
| US6908741B1 (en) | 2000-05-30 | 2005-06-21 | Transtech Pharma, Inc. | Methods to identify compounds that modulate RAGE |
| US6323228B1 (en) | 2000-09-15 | 2001-11-27 | Abbott Laboratories | 3-substituted indole angiogenesis inhibitors |
| US7312358B2 (en) | 2000-10-17 | 2007-12-25 | Laboratoires Serono Sa | Pharmaceutically active sulfanilide derivatives |
| US7163800B2 (en) | 2000-11-03 | 2007-01-16 | Molecular Devices Corporation | Methods of screening compositions for G protein-coupled receptor desensitization inhibitory activity |
| JP2004523565A (ja) | 2001-03-05 | 2004-08-05 | トランス テック ファーマ，インコーポレイテッド | 治療因子としてのベンゾイミダゾール誘導体 |
| ATE355272T1 (de) | 2001-04-20 | 2006-03-15 | Bayer Pharmaceuticals Corp | Inhibierung der raf-kinase durch chinolin-, isochinolin- oder pyridin-harnstoffe |
| US6956035B2 (en) | 2001-08-31 | 2005-10-18 | Inotek Pharmaceuticals Corporation | Isoquinoline derivatives and methods of use thereof |
| JP4505228B2 (ja) | 2002-01-10 | 2010-07-21 | バイエル・シェーリング・ファルマ・アクチェンゲゼルシャフト | Ｒｈｏ−キナーゼ阻害剤 |
| WO2003073999A2 (en) | 2002-03-01 | 2003-09-12 | Pintex Pharmaceuticals, Inc. | Pini-modulating compounds and methods of use thereof |
| EP1482931B1 (en) | 2002-03-05 | 2011-10-19 | TransTech Pharma, Inc. | Mono- and bicyclic azole derivatives that inhibit the interaction of ligands with rage |
| US7645878B2 (en) | 2002-03-22 | 2010-01-12 | Bayer Healthcare Llc | Process for preparing quinazoline Rho-kinase inhibitors and intermediates thereof |
| GB0206876D0 (en) | 2002-03-22 | 2002-05-01 | Merck Sharp & Dohme | Therapeutic agents |
| WO2003097795A2 (en) | 2002-05-13 | 2003-11-27 | Norak Biosciences, Inc. | Constitutively translocating cell line |
| US7345158B2 (en) | 2002-08-30 | 2008-03-18 | Anges Mg, Inc. | Actin related cytoskeletal protein “LACS” |
| EP1550660A1 (en) | 2002-09-12 | 2005-07-06 | Kirin Beer Kabushiki Kaisha | Isoquinoline derivatives having kinasae inhibitory activity and drugs containing the same |
| UY28213A1 (es) | 2003-02-28 | 2004-09-30 | Bayer Pharmaceuticals Corp | Nuevos derivados de cianopiridina útiles en el tratamiento de cáncer y otros trastornos. |
| EP1632477B1 (en) | 2003-06-12 | 2017-03-01 | Astellas Pharma Inc. | Benzamide derivative or salt thereof |
| WO2005020921A2 (en) | 2003-08-29 | 2005-03-10 | Exelixis, Inc. | C-kit modulators and methods of use |
| WO2005037198A2 (en) | 2003-10-06 | 2005-04-28 | Glaxo Group Limited | Preparation of 1,7-disubstituted azabenzimidazoles as kinase inhibitors |
| EP2468729B1 (en) | 2003-10-15 | 2013-12-25 | Ube Industries, Ltd. | Novel indazole derivative |
| DE10348023A1 (de) | 2003-10-15 | 2005-05-19 | Imtm Gmbh | Neue Alanyl-Aminopeptidasen-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
| JP2007008816A (ja) | 2003-10-15 | 2007-01-18 | Ube Ind Ltd | 新規イソキノリン誘導体 |
| SE0400284D0 (sv) | 2004-02-10 | 2004-02-10 | Astrazeneca Ab | Novel compounds |
| JP2005227441A (ja) | 2004-02-12 | 2005-08-25 | Konica Minolta Medical & Graphic Inc | 光熱写真画像形成材料 |
| JP4857128B2 (ja) | 2004-02-20 | 2012-01-18 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | 新規な化合物 |
| US20080096238A1 (en) | 2004-03-30 | 2008-04-24 | Alcon, Inc. | High throughput assay for human rho kinase activity with enhanced signal-to-noise ratio |
| DE102004017438A1 (de) | 2004-04-08 | 2005-11-03 | Bayer Healthcare Ag | Hetaryloxy-substituierte Phenylaminopyrimidine |
| US7453002B2 (en) | 2004-06-15 | 2008-11-18 | Bristol-Myers Squibb Company | Five-membered heterocycles useful as serine protease inhibitors |
| EP1756092A4 (en) | 2004-06-17 | 2009-12-02 | Smithkline Beecham Corp | NEW INHIBITORS OF RHO-KINASEN |
| WO2006041119A1 (ja) | 2004-10-13 | 2006-04-20 | Eisai R & D Management Co., Ltd. | ヒドラジド誘導体 |
| UY29198A1 (es) | 2004-11-09 | 2006-05-31 | Cancer Rec Tech Ltd | Derivados sustituidos de quinazolinona y derivados sustituidos de quinazolina-2, 4-diona, composiciones conteniéndolos, procedimientos de preparación y aplicaciones |
| GB0425026D0 (en) | 2004-11-12 | 2004-12-15 | Biofocus Discovery Ltd | Compounds which bind to the active site of protein kinase enzymes |
| CA2589271A1 (en) | 2004-12-07 | 2006-06-15 | Locus Pharmaceuticals, Inc. | Urea inhibitors of map kinases |
| US20080207677A1 (en) | 2004-12-31 | 2008-08-28 | Gpc Biotech Ag | Napthyridine Compounds As Rock Inhibitors |
| EP1856053A1 (en) | 2005-01-14 | 2007-11-21 | Millennium Pharmaceuticals, Inc. | Cinnamide and hydrocinnamide derivatives with raf-kinase inhibitory activity |
| WO2006086562A2 (en) | 2005-02-09 | 2006-08-17 | Microbia, Inc. | Phenylazetidinone derivatives |
| RU2007140957A (ru) | 2005-05-25 | 2009-06-27 | Вайет (Us) | Способы синтеза производных 6-алкиламинохинолинов |
| ES2580108T3 (es) | 2005-07-11 | 2016-08-19 | Aerie Pharmaceuticals, Inc | Compuestos de isoquinolina |
| US20070135499A1 (en) | 2005-07-11 | 2007-06-14 | Aerie Pharmaceuticals, Inc. | Hydrazide compounds |
| US7893050B2 (en) | 2005-10-26 | 2011-02-22 | Asahi Kasei Pharma Corporation | Fasudil in combination therapies for the treatment of pulmonary arterial hypertension |
| TW200738682A (en) | 2005-12-08 | 2007-10-16 | Organon Nv | Isoquinoline derivatives |
| JP2009521494A (ja) | 2005-12-22 | 2009-06-04 | アルコン リサーチ， リミテッド | ｒｈｏキナーゼ媒介性疾患および状態を治療するための（インダゾール−５−イル）−ピラジンおよび（１，３−ジヒドロインドール−２−オン）−ピラジン |
| AR057252A1 (es) | 2005-12-27 | 2007-11-21 | Alcon Mfg Ltd | Inhibicion de rho quinasa mediada por arni para el tratamiento de trastornos oculares |
| JP5476559B2 (ja) | 2006-02-10 | 2014-04-23 | 国立大学法人九州大学 | リン酸化酵素の新規基質ポリペプチド |
| AU2007221049A1 (en) | 2006-02-28 | 2007-09-07 | Amgen Inc. | Cinnoline and quinazoline derivates as phosphodiesterase 10 inhibitors |
| JP2007246466A (ja) | 2006-03-17 | 2007-09-27 | Osaka Univ | 中枢神経損傷に対する嗅粘膜移植にＲｈｏキナーゼ阻害剤を用いた神経機能再建法 |
| RU2008152065A (ru) | 2006-06-08 | 2010-07-20 | Убе Индастриз, Лтд (Jp) | Новое производное имидазола со спироциклической структурой в боковой цепи |
| US20090318485A1 (en) | 2006-07-20 | 2009-12-24 | Kalypsys, Inc. | Novel inhibitors of rho kinase |
| CA2658764A1 (en) | 2006-07-20 | 2008-01-24 | Mehmet Kahraman | Benzothiophene inhibitors of rho kinase |
| MX2009001037A (es) | 2006-07-31 | 2009-05-15 | Senju Pharma Co | Preparacion liquida acuosa que contiene compuesto de amida. |
| ES2729424T3 (es) | 2006-09-20 | 2019-11-04 | Aerie Pharmaceuticals Inc | Inhibidores de Rho cinasa |
| CA2700988A1 (en) | 2006-09-27 | 2008-05-08 | Surface Logix, Inc. | Rho kinase inhibitors |
| US20090036465A1 (en) | 2006-10-18 | 2009-02-05 | United Therapeutics Corporation | Combination therapy for pulmonary arterial hypertension |
| WO2008049919A2 (en) | 2006-10-26 | 2008-05-02 | Devgen N.V. | Rho kinase inhibitors |
| US8071779B2 (en) | 2006-12-18 | 2011-12-06 | Inspire Pharmaceuticals, Inc. | Cytoskeletal active rho kinase inhibitor compounds, composition and use |
| WO2008079945A2 (en) | 2006-12-20 | 2008-07-03 | University Of South Florida | Rock inhibitors and uses thereof |
| AR064420A1 (es) | 2006-12-21 | 2009-04-01 | Alcon Mfg Ltd | Composiciones farmaceuticas oftalmicas que comprenden una cantidad efectiva de analogos de 6-aminoimidazo[1,2b]piridazinas, utiles para el tratamiento del glaucoma y/o controlar la presion intraocular normal o elevada(iop). |
| JP5313919B2 (ja) | 2006-12-27 | 2013-10-09 | サノフイ | 新規な置換イソキノリン及びイソキノリノン誘導体 |
| PT2102164E (pt) | 2006-12-27 | 2011-01-21 | Sanofi Aventis | Derivados de isoquinolina e de isoquinolinona substituída com cicloalquilamina |
| RU2009128688A (ru) | 2006-12-27 | 2011-02-10 | Санофи-Авентис (Fr) | Замещенные циклоалкиламином производные изохинолина и изохинолинона |
| RU2457203C2 (ru) | 2006-12-27 | 2012-07-27 | Санофи-Авентис | Замещенные циклоалкиламином производные изохинолона |
| AU2007338410B2 (en) | 2006-12-27 | 2012-08-16 | Sanofi-Aventis | Cycloalkylamine substituted isoquinoline derivatives |
| JP5421783B2 (ja) | 2006-12-27 | 2014-02-19 | サノフイ | Ｒｈｏキナーゼ阻害剤としての置換イソキノロン及びイソキノリノン誘導体 |
| CA2673918C (en) | 2006-12-27 | 2015-02-17 | Sanofi-Aventis | Substituted isoquinoline and isoquinolinone derivatives |
| US8455513B2 (en) * | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
| JP2010523689A (ja) * | 2007-04-10 | 2010-07-15 | 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 | グルココルチコイドミメティックス、その製造方法、医薬組成物及びその使用 |
| US8455514B2 (en) | 2008-01-17 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-and 7-amino isoquinoline compounds and methods for making and using the same |
| US8450344B2 (en) | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
| EP3828172A1 (en) | 2009-05-01 | 2021-06-02 | Aerie Pharmaceuticals, Inc. | Dual mechanism inhibitors for the treatment of disease |
-
2008
- 2008-01-17 US US12/009,326 patent/US8455514B2/en active Active
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2009
- 2009-01-15 EP EP12007092.5A patent/EP2546238B1/en not_active Not-in-force
- 2009-01-15 ES ES12007093.3T patent/ES2535716T3/es active Active
- 2009-01-15 CA CA2923336A patent/CA2923336A1/en not_active Abandoned
- 2009-01-15 CA CA2712443A patent/CA2712443C/en active Active
- 2009-01-15 EP EP12007089A patent/EP2546237A1/en not_active Withdrawn
- 2009-01-15 EP EP12007093.3A patent/EP2546239B1/en not_active Not-in-force
- 2009-01-15 JP JP2010543237A patent/JP5551613B2/ja not_active Expired - Fee Related
- 2009-01-15 WO PCT/US2009/031117 patent/WO2009091898A2/en not_active Ceased
- 2009-01-15 AU AU2009206075A patent/AU2009206075B2/en not_active Ceased
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- 2009-01-15 ES ES09702189T patent/ES2397928T3/es active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2546239B1 (en) | 2015-04-08 |
| EP2546237A1 (en) | 2013-01-16 |
| AU2009206075B2 (en) | 2014-06-12 |
| AU2009206075A1 (en) | 2009-07-23 |
| US8871757B2 (en) | 2014-10-28 |
| WO2009091898A2 (en) | 2009-07-23 |
| CA2712443C (en) | 2016-05-03 |
| ES2465572T3 (es) | 2014-06-06 |
| ES2397928T3 (es) | 2013-03-12 |
| EP2546238A1 (en) | 2013-01-16 |
| JP2011510014A (ja) | 2011-03-31 |
| CA2923336A1 (en) | 2009-07-23 |
| US20090186917A1 (en) | 2009-07-23 |
| CA2712443A1 (en) | 2009-07-23 |
| JP5551613B2 (ja) | 2014-07-16 |
| WO2009091898A3 (en) | 2009-11-05 |
| EP2546238B1 (en) | 2014-04-02 |
| EP2546239A1 (en) | 2013-01-16 |
| EP2252589B1 (en) | 2012-11-21 |
| US20100144713A1 (en) | 2010-06-10 |
| EP2252589A2 (en) | 2010-11-24 |
| US8455514B2 (en) | 2013-06-04 |
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