ZA200004601B - Quinoline derivatives. - Google Patents
Quinoline derivatives. Download PDFInfo
- Publication number
- ZA200004601B ZA200004601B ZA200004601A ZA200004601A ZA200004601B ZA 200004601 B ZA200004601 B ZA 200004601B ZA 200004601 A ZA200004601 A ZA 200004601A ZA 200004601 A ZA200004601 A ZA 200004601A ZA 200004601 B ZA200004601 B ZA 200004601B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- methyl
- compound according
- ethyl
- quinoline
- Prior art date
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- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 6
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 82
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 29
- 201000006417 multiple sclerosis Diseases 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
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Classifications
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- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- 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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9801474A SE9801474D0 (sv) | 1998-04-27 | 1998-04-27 | Quinoline Derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200004601B true ZA200004601B (en) | 2002-02-27 |
Family
ID=20411103
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200004601A ZA200004601B (en) | 1998-04-27 | 2000-09-01 | Quinoline derivatives. |
Country Status (33)
Country | Link |
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EP (1) | EP1073639B1 (fr) |
JP (1) | JP4045069B2 (fr) |
KR (1) | KR100571534B1 (fr) |
CN (1) | CN1113057C (fr) |
AP (1) | AP1293A (fr) |
AT (1) | ATE228505T1 (fr) |
AU (1) | AU747550B2 (fr) |
BR (1) | BR9909925B1 (fr) |
CA (1) | CA2329788C (fr) |
CZ (1) | CZ297439B6 (fr) |
DE (1) | DE69904162T2 (fr) |
DK (1) | DK1073639T3 (fr) |
EE (1) | EE04275B1 (fr) |
ES (1) | ES2188242T3 (fr) |
HK (1) | HK1036618A1 (fr) |
HR (1) | HRP20000726B1 (fr) |
HU (1) | HU227709B1 (fr) |
ID (1) | ID26277A (fr) |
IL (2) | IL138160A0 (fr) |
IS (1) | IS2082B (fr) |
ME (1) | ME00870B (fr) |
NO (1) | NO315606B1 (fr) |
NZ (1) | NZ506641A (fr) |
OA (1) | OA11547A (fr) |
PL (1) | PL190441B1 (fr) |
PT (1) | PT1073639E (fr) |
RS (1) | RS50029B (fr) |
RU (1) | RU2197481C2 (fr) |
SE (1) | SE9801474D0 (fr) |
TR (1) | TR200003061T2 (fr) |
UA (1) | UA60354C2 (fr) |
WO (1) | WO1999055678A1 (fr) |
ZA (1) | ZA200004601B (fr) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE0002320D0 (sv) * | 1999-10-25 | 2000-06-21 | Active Biotech Ab | Malignant tumors |
SE0201778D0 (sv) * | 2002-06-12 | 2002-06-12 | Active Biotech Ab | Process for the manufacture of quinoline derivatives |
KR100908655B1 (ko) | 2002-11-27 | 2009-07-21 | 엘지디스플레이 주식회사 | 데이터 공급시간의 변조방법과 이를 이용한액정표시장치의 구동방법 및 장치 |
SE0400235D0 (sv) * | 2004-02-06 | 2004-02-06 | Active Biotech Ab | New composition containing quinoline compounds |
SE0401578D0 (sv) * | 2004-06-18 | 2004-06-18 | Active Biotech Ab | Novel compounds |
US7838522B2 (en) | 2004-11-17 | 2010-11-23 | Ares Trading S.A. | Benzothiazole formulations and use thereof |
ES2379367T3 (es) | 2004-12-21 | 2012-04-25 | Merck Serono Sa | Derivados cíclicos de sulfonilamino y uso de los mismos como inhibidores de MMP. |
US7868009B2 (en) | 2005-01-31 | 2011-01-11 | Merck Serono, S.A. | N-hydroxyamide derivatives and use thereof |
KR20080044836A (ko) | 2005-07-15 | 2008-05-21 | 라보라뚜와르 세로노 에스. 에이. | 자궁내막증 치료용 jnk 억제제 |
BRPI0613042A2 (pt) | 2005-07-15 | 2010-12-14 | Serono Lab | inibidores de jnk para o tratamento de endometriose |
CA2616479A1 (fr) | 2005-09-01 | 2007-03-08 | Ares Trading S.A. | Traitement de la nevrite optique |
CN101291911B (zh) * | 2005-10-19 | 2014-08-13 | 泰华制药工业有限公司 | 拉奎尼莫钠晶体及其制备方法 |
WO2007146248A2 (fr) | 2006-06-12 | 2007-12-21 | Teva Pharmaceutical Industries, Ltd. | Préparations de laquinimod stables |
PL2234485T3 (pl) | 2007-12-20 | 2014-06-30 | Teva Pharma | Stabilne preparaty lakwinimodu |
CN104311486A (zh) * | 2008-09-03 | 2015-01-28 | 泰华制药工业有限公司 | 2-羰基-1,2-二氢喹啉免疫功能调节剂 |
EA025468B1 (ru) | 2009-07-30 | 2016-12-30 | Тева Фармасьютикал Индастриз Лтд. | Лечение болезни крона с применением лаквинимода |
JP5859438B2 (ja) * | 2009-08-10 | 2016-02-10 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドを用いたbdnf関連疾患の治療 |
PE20130496A1 (es) * | 2010-03-03 | 2013-05-08 | Teva Pharma | Tratamiento de artritis por lupus usando laquinimod |
JP5819328B2 (ja) | 2010-03-03 | 2015-11-24 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドとメトトレキセートとの組合せによる関節リウマチの治療 |
SG10201501535UA (en) * | 2010-03-03 | 2015-04-29 | Teva Pharma | Treatment of lupus nephritis using laquinimod |
WO2011116091A1 (fr) | 2010-03-17 | 2011-09-22 | Novartis Ag | Distributeur |
BR112013000607A2 (pt) * | 2010-07-09 | 2016-06-28 | Teva Pharma | 5-cloro-4-hidroxi-1-metil-2-oxo-n-fenil-1,2-di-hidroquinolina-3-carboxamida, os sais e suas utilizações |
AR082150A1 (es) * | 2010-07-09 | 2012-11-14 | Teva Pharma | N-etil-n-fenil-1,2-dihidro-4-hidroxi-5-cloro-1-metil-2-oxoquinolin-3-carboxamida deuterada, sales y usos de la misma, metodo de tratamiento, mezcla compuestos, composicion farmaceutica, proceso de preparacion, compuesto enriquecido con deuterio |
SG186430A1 (en) | 2010-07-09 | 2013-01-30 | Active Biotech Ab | Method for manufacturing of quinoline-3-carboxamides |
EP2444086A1 (fr) | 2010-10-22 | 2012-04-25 | Almirall, S.A. | Combinaisons comportant des inhibiteurs de DHODH et de COX |
CA2851525A1 (fr) | 2011-10-12 | 2013-04-18 | Teva Pharmaceutical Industries Ltd. | Traitement de la sclerose en plaques par combinaison de laquinimod et de fingolimod |
AU2013214909A1 (en) | 2012-02-03 | 2014-09-18 | Teva Pharmaceutical Industries Ltd. | Use of laquinimod for treating Crohn's disease patients who failed first-line anti-TNFa therapy |
WO2013123419A1 (fr) | 2012-02-16 | 2013-08-22 | Teva Pharmaceutical Industries Ltd. | N-éthyl-n-phényl -1,2-dihydro -4,5-di-hydroxy -1-méthyl -2-oxo -3-quinoléine carboxamide, sa préparation et son utilisation |
TW201350467A (zh) | 2012-05-08 | 2013-12-16 | Teva Pharma | N-乙基-4-羥基-1-甲基-5-(甲基(2,3,4,5,6-五羥基己基)胺基)-2-側氧-n-苯基-1,2-二氫喹啉-3-甲醯胺 |
TW201400117A (zh) | 2012-06-05 | 2014-01-01 | Teva Pharma | 使用拉喹莫德治療眼發炎疾病 |
TW201410244A (zh) | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療gaba媒介之疾病之拉喹莫德(laquinimod) |
JP2015535287A (ja) | 2012-11-07 | 2015-12-10 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドのアミン塩 |
RU2545056C2 (ru) * | 2012-12-10 | 2015-03-27 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия" Министерства здавоохранения и социального развития Российской Федерации (ГБОУ ВПО ПГФА Минздравсоцразвития России) | Противовоспалительное и анальгетическое средство на основе изопропиламида 1,2-дигидро-1н-2-оксоцинхониновой кислоты |
CN105163737A (zh) * | 2013-02-15 | 2015-12-16 | 梯瓦制药工业有限公司 | 用拉喹莫德治疗多发性硬化症 |
WO2014153145A2 (fr) | 2013-03-14 | 2014-09-25 | Teva Pharmaceutical Industries Ltd. | Cristaux de sodium de laquinimod et procédé amélioré pour leur fabrication |
JP2017514824A (ja) | 2014-04-29 | 2017-06-08 | テバ ファーマシューティカル インダストリーズ リミティド | 能力障害度が高い再発寛解型多発性硬化症(rrms)患者の処置のためのラキニモド |
KR102533033B1 (ko) | 2014-09-23 | 2023-05-15 | 액티브 바이오테크 에이비 | 다발성 골수종의 치료에 사용하기 위한 퀴놀린 카르복사미드 |
MX2017006110A (es) | 2014-11-19 | 2017-07-27 | Active Biotech Ab | Carboxamidas de quinolina para usarse en el tratamiento de leucemia. |
EP3886858B1 (fr) | 2019-12-19 | 2022-05-11 | Active Biotech AB | Composés pour le traitement de maladies des yeux associées à une vascularisation excessive |
KR20220149579A (ko) | 2020-03-03 | 2022-11-08 | 액티브 바이오테크 에이비 | 조합 요법에 사용하기 위한 타스퀴니모드 또는 이의 약학적으로 허용가능한 염 |
EP4153576A4 (fr) * | 2020-05-21 | 2024-06-19 | StemSynergy Therapeutics, Inc. | Inhibiteurs de notch et leurs utilisations |
CN116782902A (zh) | 2020-07-23 | 2023-09-19 | 伊拉兹马斯大学鹿特丹医学中心 | 作为骨髓增殖性肿瘤中的新治疗靶标的s100蛋白 |
JP2024503372A (ja) | 2021-01-18 | 2024-01-25 | アクティブ バイオテック エイビー | 骨髄異形成症候群の処置における使用のためのタスキニモドまたはその薬学的に許容される塩 |
US20240285532A1 (en) | 2021-05-25 | 2024-08-29 | Active Biotech Ab | A plurality of tasquinimod particles and use thereof |
IL309486A (en) | 2021-07-02 | 2024-02-01 | Active Biotech Ab | A pharmacy product containing tesquinimod and a method for evaluating the cleanliness of this product |
Family Cites Families (2)
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IE52670B1 (en) * | 1981-03-03 | 1988-01-20 | Leo Ab | Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation |
GB9108547D0 (en) * | 1991-04-22 | 1991-06-05 | Fujisawa Pharmaceutical Co | Quinoline derivatives |
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