IL112010A - תכשירי רוקחות המכילים תולדות אוקסינדול מותמרות בעמדה 3 בעלי פעילות נגד היצרות כלי-דם - Google Patents
תכשירי רוקחות המכילים תולדות אוקסינדול מותמרות בעמדה 3 בעלי פעילות נגד היצרות כלי-דםInfo
- Publication number
- IL112010A IL112010A IL11201094A IL11201094A IL112010A IL 112010 A IL112010 A IL 112010A IL 11201094 A IL11201094 A IL 11201094A IL 11201094 A IL11201094 A IL 11201094A IL 112010 A IL112010 A IL 112010A
- Authority
- IL
- Israel
- Prior art keywords
- oxindole
- methylen
- hydroxy
- hydrogen
- indolyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 230000001772 anti-angiogenic effect Effects 0.000 title claims description 3
- 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 title 1
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
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- -1 cyano, carboxy Chemical group 0.000 claims abstract description 28
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 25
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 22
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
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- 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
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- 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
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- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939326136A GB9326136D0 (en) | 1993-12-22 | 1993-12-22 | Biologically active 3-substituted oxindole derivatives useful as anti-angiogenic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL112010A0 IL112010A0 (en) | 1995-03-15 |
| IL112010A true IL112010A (he) | 1998-10-30 |
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| IL11201094A IL112010A (he) | 1993-12-22 | 1994-12-16 | תכשירי רוקחות המכילים תולדות אוקסינדול מותמרות בעמדה 3 בעלי פעילות נגד היצרות כלי-דם |
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| Country | Link |
|---|---|
| US (1) | US5576330A (he) |
| EP (1) | EP0684820B1 (he) |
| JP (1) | JPH08507089A (he) |
| KR (1) | KR960700707A (he) |
| AT (1) | ATE204168T1 (he) |
| AU (1) | AU676958B2 (he) |
| CA (1) | CA2155098A1 (he) |
| DE (1) | DE69427962T2 (he) |
| ES (1) | ES2162871T3 (he) |
| GB (1) | GB9326136D0 (he) |
| HU (1) | HUT73176A (he) |
| IL (1) | IL112010A (he) |
| NO (1) | NO953146D0 (he) |
| PL (1) | PL310379A1 (he) |
| TW (1) | TW273510B (he) |
| WO (1) | WO1995017181A1 (he) |
| ZA (1) | ZA9410204B (he) |
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| GB9501567D0 (en) * | 1995-01-26 | 1995-03-15 | Pharmacia Spa | Hydrosoluble 3-arylidene-2-oxindole derivatives as tyrosine kinase inhibitors |
| US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US6906093B2 (en) | 1995-06-07 | 2005-06-14 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
| US6147106A (en) | 1997-08-20 | 2000-11-14 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
| GB9610964D0 (en) * | 1996-05-24 | 1996-07-31 | Pharmacia & Upjohn Spa | Substituted tetralylmethylen-oxindole analogues as tyrosine kinase inhibitors |
| GB9611797D0 (en) * | 1996-06-06 | 1996-08-07 | Pharmacia Spa | Substituted quinolylmethylen-oxindole analogues as tyrosine kinase inhibitors |
| GB9613021D0 (en) * | 1996-06-21 | 1996-08-28 | Pharmacia Spa | Bicyclic 4-aralkylaminopyrimidine derivatives as tyrosine kinase inhibitors |
| WO1998024432A2 (en) * | 1996-12-05 | 1998-06-11 | Sugen, Inc. | Use of indolinone compounds as modulators of protein kinases |
| WO1999009982A1 (en) | 1997-08-25 | 1999-03-04 | Harold Brem | Prevention of adhesions and excessive scar formation using angiogenesis inhibitors |
| US6531502B1 (en) | 1998-01-21 | 2003-03-11 | Sugen, Inc. | 3-Methylidenyl-2-indolinone modulators of protein kinase |
| US6569868B2 (en) | 1998-04-16 | 2003-05-27 | Sugen, Inc. | 2-indolinone derivatives as modulators of protein kinase activity |
| CA2333147C (en) | 1998-07-13 | 2012-02-07 | Board Of Regents, The University Of Texas System | Cancer treatment methods using antibodies to aminophospholipids |
| SI1107795T1 (en) | 1998-09-04 | 2003-06-30 | The Regents Of The University Of Michigan | Thiomolybdate associated with at least one carbohydrate, and its use for preventing or treating diseases characterized by aberrant vascularization, such as cancer, wet type macular degeneration, rheumatoid arthritis |
| AU5991699A (en) | 1998-09-21 | 2000-04-10 | Biochem Pharma Inc. | Quinolizinones as integrin inhibitors |
| CN1136217C (zh) | 1998-12-17 | 2004-01-28 | 霍夫曼-拉罗奇有限公司 | 作为jnk蛋白质激酶抑制剂的4-芳基羟吲哚 |
| KR20010108024A (ko) | 1998-12-17 | 2001-12-07 | 프리돌린 클라우스너, 롤란드 비. 보레르 | 단백질 키나제 억제제로서의 4,5-피라진옥신돌 |
| US6153634A (en) * | 1998-12-17 | 2000-11-28 | Hoffmann-La Roche Inc. | 4,5-azolo-oxindoles |
| BR9916327A (pt) | 1998-12-17 | 2001-09-18 | Hoffmann La Roche | Oxindóis de 4-alquenila (e alquinila) como inibidores de cinases dependentes de ciclina, em particular, cdk2 |
| US6509334B1 (en) * | 1999-05-04 | 2003-01-21 | American Home Products Corporation | Cyclocarbamate derivatives as progesterone receptor modulators |
| US6391907B1 (en) | 1999-05-04 | 2002-05-21 | American Home Products Corporation | Indoline derivatives |
| US6355648B1 (en) * | 1999-05-04 | 2002-03-12 | American Home Products Corporation | Thio-oxindole derivatives |
| US6673843B2 (en) * | 1999-06-30 | 2004-01-06 | Emory University | Curcumin and curcuminoid inhibition of angiogenesis |
| US6313310B1 (en) | 1999-12-15 | 2001-11-06 | Hoffmann-La Roche Inc. | 4-and 5-alkynyloxindoles and 4-and 5-alkenyloxindoles |
| JP3663382B2 (ja) | 2000-02-15 | 2005-06-22 | スージェン・インコーポレーテッド | ピロール置換2−インドリノン蛋白質キナーゼ阻害剤 |
| MY128450A (en) | 2000-05-24 | 2007-02-28 | Upjohn Co | 1-(pyrrolidin-1-ylmethyl)-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives |
| AU2001258628A1 (en) * | 2000-05-31 | 2001-12-11 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| JP2003535847A (ja) | 2000-06-02 | 2003-12-02 | スージェン・インコーポレーテッド | 蛋白質キナーゼ/ホスファターゼ阻害剤としてのインドリノン誘導体 |
| AU9598601A (en) | 2000-10-20 | 2002-04-29 | Eisai Co Ltd | Nitrogenous aromatic ring compounds |
| AR042586A1 (es) | 2001-02-15 | 2005-06-29 | Sugen Inc | 3-(4-amidopirrol-2-ilmetiliden)-2-indolinona como inhibidores de la protein quinasa; sus composiciones farmaceuticas; un metodo para la modulacion de la actividad catalitica de la proteinquinasa; un metodo para tratar o prevenir una afeccion relacionada con la proteinquinasa |
| US6599902B2 (en) | 2001-05-30 | 2003-07-29 | Sugen, Inc. | 5-aralkysufonyl-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives as kinase inhibitors |
| US6797825B2 (en) | 2001-12-13 | 2004-09-28 | Abbott Laboratories | Protein kinase inhibitors |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| EP1572078A4 (en) * | 2002-03-08 | 2006-08-09 | Univ Emory | NEW CURCUMINOID FACTOR VIIa CONSTRUCTS AS MEANS OF SUPPRESSING TUMOR GROWTH AND ANGIOGENESIS |
| KR20120068769A (ko) | 2002-07-15 | 2012-06-27 | 더 보드 오브 리전츠 오브 더 유니버시티 오브 텍사스 시스템 | 음이온성 인지질 및 아미노인지질에 결합하는 선택된 항체 및 치료하는데 있어서 이의 용도 |
| ATE508747T1 (de) | 2003-03-10 | 2011-05-15 | Eisai R&D Man Co Ltd | C-kit kinase-hemmer |
| US7683172B2 (en) | 2003-11-11 | 2010-03-23 | Eisai R&D Management Co., Ltd. | Urea derivative and process for preparing the same |
| KR101395370B1 (ko) | 2004-01-22 | 2014-05-14 | 유니버시티 오브 마이애미 | 국소용 코-엔자임 큐10 제형 및 그의 사용 방법 |
| ATE428421T1 (de) | 2004-09-17 | 2009-05-15 | Eisai R&D Man Co Ltd | Medizinische zusammensetzung mit verbesserter stabilität und reduzierten gelierungseigenschaften |
| JP4989476B2 (ja) | 2005-08-02 | 2012-08-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 血管新生阻害物質の効果を検定する方法 |
| CN104706637A (zh) | 2006-05-18 | 2015-06-17 | 卫材R&D管理有限公司 | 针对甲状腺癌的抗肿瘤剂 |
| WO2008026748A1 (en) | 2006-08-28 | 2008-03-06 | Eisai R & D Management Co., Ltd. | Antitumor agent for undifferentiated gastric cancer |
| CA2676796C (en) | 2007-01-29 | 2016-02-23 | Eisai R & D Management Co., Ltd. | Composition for treatment of undifferentiated gastric cancer |
| CA2705152C (en) | 2007-11-09 | 2016-10-11 | Peregrine Pharmaceuticals, Inc. | Anti-vegf antibody compositions and methods |
| US8952035B2 (en) | 2007-11-09 | 2015-02-10 | Eisai R&D Management Co., Ltd. | Combination of anti-angiogenic substance and anti-tumor platinum complex |
| EP2323679A4 (en) | 2008-07-25 | 2012-08-22 | Univ Colorado | CLIP INHIBITORS AND METHODS FOR MODULATING IMMUNE FUNCTION |
| MY162940A (en) | 2009-08-19 | 2017-07-31 | Eisai R&D Man Co Ltd | Quinoline derivative-containing pharmaceutical composition |
| CN102958523B (zh) | 2010-06-25 | 2014-11-19 | 卫材R&D管理有限公司 | 使用具有激酶抑制作用的组合的抗肿瘤剂 |
| CN102115469A (zh) * | 2011-03-21 | 2011-07-06 | 浙江大学 | 吲哚啉-2-酮类衍生物的制备和用途 |
| CN103402519B (zh) | 2011-04-18 | 2015-11-25 | 卫材R&D管理有限公司 | 肿瘤治疗剂 |
| JP6038128B2 (ja) | 2011-06-03 | 2016-12-07 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | レンバチニブ化合物に対する甲状腺癌対象及び腎臓癌対象の反応性を予測及び評価するためのバイオマーカー |
| KR20150098605A (ko) | 2012-12-21 | 2015-08-28 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 퀴놀린 유도체의 비정질 형태 및 그의 제조방법 |
| NZ714049A (en) | 2013-05-14 | 2020-05-29 | Eisai R&D Man Co Ltd | Biomarkers for predicting and assessing responsiveness of endometrial cancer subjects to lenvatinib compounds |
| EP2837626A1 (en) * | 2013-08-16 | 2015-02-18 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Indolinone derivatives as GRK5 modulators |
| PT3524595T (pt) | 2014-08-28 | 2022-09-19 | Eisai R&D Man Co Ltd | Derivado de quinolina altamente puro e método para produção do mesmo |
| LT3263106T (lt) | 2015-02-25 | 2024-01-10 | Eisai R&D Management Co., Ltd. | Chinolino darinių kartumo sumažinimo būdas |
| KR102662228B1 (ko) | 2015-03-04 | 2024-05-02 | 머크 샤프 앤드 돔 코포레이션 | 암을 치료하기 위한 pd-1 길항제 및 vegfr/fgfr/ret 티로신 키나제 억제제의 조합 |
| MX373231B (es) | 2015-06-16 | 2020-05-08 | Eisai R&D Man Co Ltd | Agente anticancerigeno. |
| US12220398B2 (en) | 2015-08-20 | 2025-02-11 | Eisai R&D Management Co., Ltd. | Tumor therapeutic agent |
| EP3576726A1 (en) | 2017-02-06 | 2019-12-11 | Massachusetts Institute Of Technology | Methods and products related to glutaminase inhibitors |
| US12303505B2 (en) | 2017-02-08 | 2025-05-20 | Eisai R&D Management Co., Ltd. | Tumor-treating pharmaceutical composition |
| RU2019134940A (ru) | 2017-05-16 | 2021-06-16 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Лечение гепатоцеллюлярной карциномы |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9000950D0 (en) * | 1990-01-16 | 1990-03-14 | Erba Carlo Spa | New arylvinylamide derivatives and process for their preparation |
| GB9000939D0 (en) * | 1990-01-16 | 1990-03-14 | Erba Carlo Spa | Improvement in the total synthesis of erbstatin analogs |
| GB9004483D0 (en) * | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
| FI935279L (fi) * | 1991-05-29 | 1993-11-26 | Pfizer | Tricykliska polyhydroxyltyrosinkinasininhibitorer |
| GB9115160D0 (en) * | 1991-07-12 | 1991-08-28 | Erba Carlo Spa | Methylen-oxindole derivatives and process for their preparation |
| GB9127376D0 (en) * | 1991-12-24 | 1992-02-19 | Wellcome Found | Amidino derivatives |
| WO1994003427A1 (en) * | 1992-08-06 | 1994-02-17 | Warner-Lambert Company | 2-thioindoles (selenoindoles) and related disulfides (selenides) which inhibit protein tyrosine kinases and which have antitumor properties |
| GB9226855D0 (en) * | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
-
1993
- 1993-12-22 GB GB939326136A patent/GB9326136D0/en active Pending
-
1994
- 1994-11-08 CA CA002155098A patent/CA2155098A1/en not_active Abandoned
- 1994-11-08 ES ES94931583T patent/ES2162871T3/es not_active Expired - Lifetime
- 1994-11-08 KR KR1019950703524A patent/KR960700707A/ko not_active Withdrawn
- 1994-11-08 HU HU9502761A patent/HUT73176A/hu unknown
- 1994-11-08 PL PL94310379A patent/PL310379A1/xx unknown
- 1994-11-08 WO PCT/EP1994/003664 patent/WO1995017181A1/en not_active Ceased
- 1994-11-08 AU AU80612/94A patent/AU676958B2/en not_active Ceased
- 1994-11-08 JP JP7517121A patent/JPH08507089A/ja active Pending
- 1994-11-08 AT AT94931583T patent/ATE204168T1/de not_active IP Right Cessation
- 1994-11-08 EP EP94931583A patent/EP0684820B1/en not_active Expired - Lifetime
- 1994-11-08 DE DE69427962T patent/DE69427962T2/de not_active Expired - Fee Related
- 1994-11-15 TW TW083110552A patent/TW273510B/zh active
- 1994-12-12 US US08/354,215 patent/US5576330A/en not_active Expired - Fee Related
- 1994-12-12 ZA ZA9410204A patent/ZA9410204B/xx unknown
- 1994-12-16 IL IL11201094A patent/IL112010A/he not_active IP Right Cessation
-
1995
- 1995-08-10 NO NO953146A patent/NO953146D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR960700707A (ko) | 1996-02-24 |
| GB9326136D0 (en) | 1994-02-23 |
| NO953146L (no) | 1995-08-10 |
| ZA9410204B (en) | 1995-11-10 |
| AU8061294A (en) | 1995-07-10 |
| US5576330A (en) | 1996-11-19 |
| ATE204168T1 (de) | 2001-09-15 |
| NO953146D0 (no) | 1995-08-10 |
| DE69427962D1 (de) | 2001-09-20 |
| CA2155098A1 (en) | 1995-06-29 |
| EP0684820A1 (en) | 1995-12-06 |
| WO1995017181A1 (en) | 1995-06-29 |
| HU9502761D0 (en) | 1995-11-28 |
| JPH08507089A (ja) | 1996-07-30 |
| ES2162871T3 (es) | 2002-01-16 |
| PL310379A1 (en) | 1995-12-11 |
| IL112010A0 (en) | 1995-03-15 |
| HUT73176A (en) | 1996-06-28 |
| EP0684820B1 (en) | 2001-08-16 |
| AU676958B2 (en) | 1997-03-27 |
| DE69427962T2 (de) | 2002-04-04 |
| TW273510B (he) | 1996-04-01 |
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Free format text: ADD COUNTRY OF APPLICANT: USA; CORRECT INTERNATIONAL PUBLICATION NO.: WO/2003/009465; CORRECT PRIORITY NUMBER: 00110355.5 |