TW200423938A - 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-alkoxy-3-quinolinecarbonitriles for the treatment of ischemic injury - Google Patents
4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-alkoxy-3-quinolinecarbonitriles for the treatment of ischemic injury Download PDFInfo
- Publication number
- TW200423938A TW200423938A TW093103901A TW93103901A TW200423938A TW 200423938 A TW200423938 A TW 200423938A TW 093103901 A TW093103901 A TW 093103901A TW 93103901 A TW93103901 A TW 93103901A TW 200423938 A TW200423938 A TW 200423938A
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- Prior art keywords
- amino
- dichloro
- methoxyphenyl
- methoxy
- ethoxy
- Prior art date
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- -1 2,4-dichloro-5-methoxyphenyl Chemical group 0.000 title claims description 128
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 81
- 238000011282 treatment Methods 0.000 title description 21
- 208000037906 ischaemic injury Diseases 0.000 title description 7
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
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- 238000000034 method Methods 0.000 claims description 68
- 230000000302 ischemic effect Effects 0.000 claims description 28
- 208000006011 Stroke Diseases 0.000 claims description 23
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 23
- QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
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- TXAYKQMEBQBGLR-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl TXAYKQMEBQBGLR-UHFFFAOYSA-N 0.000 claims description 5
- JNVVCLAXQUVGKP-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-methylpiperidin-1-yl)propoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCC(C)CC4)C=C3N=CC=2C#N)=C1Cl JNVVCLAXQUVGKP-UHFFFAOYSA-N 0.000 claims description 5
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- JQGPWNQWNMMMAS-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCC3CCN(C)CC3)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl JQGPWNQWNMMMAS-UHFFFAOYSA-N 0.000 claims description 3
- HOHWAQXKWAAULM-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[(1-ethylpiperidin-4-yl)methoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1CN(CC)CCC1COC1=CC2=NC=C(C#N)C(NC=3C(=CC(Cl)=C(OC)C=3)Cl)=C2C=C1OC HOHWAQXKWAAULM-UHFFFAOYSA-N 0.000 claims description 3
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- OSJKQGUEJYZHQM-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-[3-(1-methylpiperidin-4-yl)propoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCC3CCN(C)CC3)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl OSJKQGUEJYZHQM-UHFFFAOYSA-N 0.000 claims 3
- QXWCRBMAGJJKTO-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(1-methylpiperidin-4-yl)propoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCC4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl QXWCRBMAGJJKTO-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4706—4-Aminoquinolines; 8-Aminoquinolines, e.g. chloroquine, primaquine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
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| CA (1) | CA2516418A1 (enExample) |
| CO (1) | CO5640114A2 (enExample) |
| CR (1) | CR7931A (enExample) |
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| SG146681A1 (en) * | 2003-11-06 | 2008-10-30 | Wyeth Corp | 4-anilino-3-quinolinecarbonitriles for the treatment of chronic myelogenous leukemia (cml) |
| RU2007111704A (ru) * | 2004-10-22 | 2008-11-27 | Вайет (Us) | 4[(2,4-дихлоро-5-метоксифенил)амино]-6-алкокси-7-этинил-3-хинолинкарбонитрилы для лечения ишемического поражения |
| MX2008000384A (es) * | 2005-07-01 | 2008-03-07 | Wyeth Corp | Formas cristalinas de 4-[(2,4-dicloro-5-metoxifenil)amino]-6-metox i-7-[3-(4-metil-1-piperazinil)propoxi]-3-quinolinocarbonitrilo y metodos para su preparacion. |
| MX342879B (es) | 2010-07-30 | 2016-10-14 | Oncotherapy Science Inc * | Derivados de quinolina e inhibidores de cinasa de cremallera de leucina embrionica materna que los contienen. |
| CN103772392A (zh) * | 2012-10-23 | 2014-05-07 | 杨子娇 | 一类治疗房角狭窄的化合物及其用途 |
| IN2014CH00840A (enExample) | 2014-02-20 | 2015-09-18 | Apotex Inc | |
| TWI672141B (zh) | 2014-02-20 | 2019-09-21 | 美商醫科泰生技 | 投予ｒｏｓ１突變癌細胞之分子 |
| US20160256457A1 (en) * | 2014-06-10 | 2016-09-08 | Beth Israel Deaconess Medical Center, Inc. | Methods for treating or preventing acute vascular leak |
| AU2015355220B2 (en) | 2014-12-02 | 2020-02-27 | Ignyta, Inc. | Combinations for the treatment of neuroblastoma |
| WO2017029584A1 (en) * | 2015-08-19 | 2017-02-23 | Sun Pharmaceutical Industries Limited | Amorphous form of bosutinib |
| KR20180096621A (ko) | 2015-12-18 | 2018-08-29 | 이그니타, 인코포레이티드 | 암의 치료용 조합물 |
| CN107814769B (zh) * | 2016-09-14 | 2021-05-07 | 正大天晴药业集团股份有限公司 | 一种博舒替尼的纯化方法 |
| WO2019018570A1 (en) | 2017-07-19 | 2019-01-24 | Ignyta, Inc. | PHARMACEUTICAL COMPOSITIONS CONTAINING ENTRECTINIB |
| JP7311498B2 (ja) | 2017-10-17 | 2023-07-19 | イグナイタ インコーポレイテッド | 薬学的組成物および剤形 |
| CN111646940B (zh) * | 2019-03-04 | 2024-01-30 | 鲁南制药集团股份有限公司 | 一种博舒替尼中间体的制备方法 |
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|---|---|---|---|---|
| US6002008A (en) * | 1997-04-03 | 1999-12-14 | American Cyanamid Company | Substituted 3-cyano quinolines |
| US6297258B1 (en) * | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| US6521618B2 (en) * | 2000-03-28 | 2003-02-18 | Wyeth | 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors |
| TWI275390B (en) * | 2002-04-30 | 2007-03-11 | Wyeth Corp | Process for the preparation of 7-substituted-3- quinolinecarbonitriles |
| US20060167021A1 (en) * | 2002-10-04 | 2006-07-27 | Caritas St. Elizabeth's Medical Center Of Boston, Inc. | Inhibition of src for treatment of reperfusion injury related to revascularization |
-
2004
- 2004-02-18 US US10/780,973 patent/US20040229880A1/en not_active Abandoned
- 2004-02-18 TW TW093103901A patent/TW200423938A/zh unknown
- 2004-02-19 AU AU2004216235A patent/AU2004216235A1/en not_active Withdrawn
- 2004-02-19 BR BR0407441-6A patent/BRPI0407441A/pt not_active IP Right Cessation
- 2004-02-19 CN CNA2004800046743A patent/CN1750824A/zh active Pending
- 2004-02-19 JP JP2006503706A patent/JP2006522023A/ja not_active Withdrawn
- 2004-02-19 EP EP04712889A patent/EP1594502A1/en not_active Withdrawn
- 2004-02-19 RU RU2005129333/04A patent/RU2005129333A/ru not_active Application Discontinuation
- 2004-02-19 MX MXPA05008706A patent/MXPA05008706A/es unknown
- 2004-02-19 UA UAA200508924A patent/UA80472C2/uk unknown
- 2004-02-19 KR KR1020057015377A patent/KR20050102133A/ko not_active Withdrawn
- 2004-02-19 CA CA002516418A patent/CA2516418A1/en not_active Abandoned
- 2004-02-19 WO PCT/US2004/004904 patent/WO2004075898A1/en not_active Ceased
- 2004-02-20 AR ARP040100546A patent/AR043253A1/es not_active Application Discontinuation
-
2005
- 2005-08-03 CR CR7931A patent/CR7931A/es not_active Application Discontinuation
- 2005-08-17 CO CO05081472A patent/CO5640114A2/es not_active Application Discontinuation
- 2005-08-18 ZA ZA200506621A patent/ZA200506621B/en unknown
- 2005-08-19 EC EC2005005972A patent/ECSP055972A/es unknown
- 2005-09-01 NO NO20054070A patent/NO20054070L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004075898A1 (en) | 2004-09-10 |
| US20040229880A1 (en) | 2004-11-18 |
| NO20054070D0 (no) | 2005-09-01 |
| MXPA05008706A (es) | 2005-10-05 |
| KR20050102133A (ko) | 2005-10-25 |
| RU2005129333A (ru) | 2006-01-27 |
| CA2516418A1 (en) | 2004-09-10 |
| CO5640114A2 (es) | 2006-05-31 |
| AR043253A1 (es) | 2005-07-20 |
| JP2006522023A (ja) | 2006-09-28 |
| ZA200506621B (en) | 2008-02-27 |
| NO20054070L (no) | 2005-11-14 |
| ECSP055972A (es) | 2006-01-16 |
| BRPI0407441A (pt) | 2006-01-31 |
| AU2004216235A1 (en) | 2004-09-10 |
| UA80472C2 (en) | 2007-09-25 |
| CR7931A (es) | 2006-02-07 |
| CN1750824A (zh) | 2006-03-22 |
| EP1594502A1 (en) | 2005-11-16 |
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