ZA200004601B - Quinoline derivatives. - Google Patents

Quinoline derivatives. Download PDF

Info

Publication number: ZA200004601B
Authority: ZA; South Africa
Prior art keywords: compound; methyl; compound according; ethyl; quinoline
Prior art date: 1998-04-27

Application number

ZA200004601A

Other languages

English (en)

Inventor

Anders Bjoerk

Stig Joensson

Tomas Fex

Gunnar Hedlund

Original Assignee

Active Biotech Ab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-04-27

Filing date

2000-09-01

Publication date

2002-02-27

2000-09-01 Application filed by Active Biotech Ab filed Critical Active Biotech Ab

2002-02-27 Publication of ZA200004601B publication Critical patent/ZA200004601B/en

Links

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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
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
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
-1 methoxy, ethoxy Chemical group 0.000 claims description 7
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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
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
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238000010168 coupling process Methods 0.000 claims description 6
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
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HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
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VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
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GKWPCEFFIHSJOE-UHFFFAOYSA-N laquinimod Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 GKWPCEFFIHSJOE-UHFFFAOYSA-N 0.000 claims description 2
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
SGOOQMRIPALTEL-UHFFFAOYSA-N 4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-3-quinolinecarboxamide Chemical compound OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 SGOOQMRIPALTEL-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000005160 1H NMR spectroscopy Methods 0.000 description 20
229960003522 roquinimex Drugs 0.000 description 20
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239000002244 precipitate Substances 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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150000003248 quinolines Chemical class 0.000 description 6
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BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
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208000011580 syndromic disease Diseases 0.000 description 5
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BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 description 4
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- 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
- 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
- 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]
- 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
- 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
- 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
- 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
- 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

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)
Neurosurgery (AREA)
Immunology (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Vascular Medicine (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Emergency Medicine (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Dermatology (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200004601A 1998-04-27 2000-09-01 Quinoline derivatives. ZA200004601B (en)

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 (32)

Country	Link
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)
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 (47)

* Cited by examiner, † Cited by third party
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
RS52193B (sr)	2004-12-21	2012-10-31	Merck Serono Sa.	Ciklični derivati sulfonil amina i njihova upotreba
DK1844032T3 (da)	2005-01-31	2011-10-24	Merck Serono Sa	N-hydroxyamid-derivater og deres anvendelse
BRPI0613042A2 (pt)	2005-07-15	2010-12-14	Serono Lab	inibidores de jnk para o tratamento de endometriose
KR20080044836A (ko)	2005-07-15	2008-05-21	라보라뚜와르 세로노 에스. 에이.	자궁내막증 치료용 ｊｎｋ 억제제
AU2006286489B2 (en)	2005-09-01	2012-08-09	Ares Trading S.A.	Treatment of optic neuritis
SI1937642T1 (sl) *	2005-10-19	2015-01-30	Teva Pharmaceutical Industries Ltd.	Kristali natrijevega lakvinimoda in postopek za njihovo pripravo
CN101466379B (zh) *	2006-06-12	2012-10-31	泰华制药工业有限公司	稳定的拉喹莫德的制剂
EP2234485B1 (fr)	2007-12-20	2013-11-13	Teva Pharmaceutical Industries, Ltd.	Préparations de laquinimod stables
KR20110048571A (ko)	2008-09-03	2011-05-11	테바 파마슈티컬 인더스트리즈 리미티드	면역 기능을 지닌 ２―옥소―１,２―다이하이드로―퀴놀린 조절제
RS54707B1 (sr) *	2009-07-30	2016-08-31	Teva Pharmaceutical Industries Ltd.	Tretman kronove bolesti lakvinimodom
PL2467372T3 (pl) *	2009-08-10	2017-04-28	Teva Pharmaceutical Industries Ltd.	Leczenie zaburzeń związanych z BDNF z zastosowaniem lakwinimodu
US8889661B2 (en) *	2010-03-03	2014-11-18	Teva Pharmaceutical Industries, Ltd.	Treatment of lupus nephritis using laquinimod
PH12012501741A1 (en) *	2010-03-03	2012-11-12	Teva Pharma	Treatment of lupus arthritis using laquinimod
KR20130014523A (ko)	2010-03-03	2013-02-07	테바 파마슈티컬 인더스트리즈 리미티드	라퀴니모드 및 메토트렉세이트의 병용에 의한 류마티스 관절염의 치료
WO2011116091A1 (fr)	2010-03-17	2011-09-22	Novartis Ag	Distributeur
AU2011275720B2 (en) *	2010-07-09	2015-05-14	Active Biotech Ab	Method for manufacturing of quinoline-3-carboxamides
SG186948A1 (en)	2010-07-09	2013-02-28	Teva Pharma	Deuterated n-ethyl-n-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide, salts and uses thereof
KR20130041193A (ko) *	2010-07-09	2013-04-24	테바 파마슈티컬 인더스트리즈 리미티드	5-클로로-4-하이드록시-1-메틸-2-옥소-n-페닐-1,2-다이하이드로퀴놀린-3-카복스아마이드, 염 및 그의 용도
EP2444086A1 (fr)	2010-10-22	2012-04-25	Almirall, S.A.	Combinaisons comportant des inhibiteurs de DHODH et de COX
US8889627B2 (en)	2011-10-12	2014-11-18	Teva Pharmaceutical Industries, Ltd.	Treatment of multiple sclerosis with combination of laquinimod and fingolimod
US9161935B2 (en) *	2012-02-03	2015-10-20	Teva Pharmaceutical Industries, Ltd.	Use of laquinimod for treating Crohn's disease patients who failed first-line anti-TNF therapy
EA201491517A1 (ru)	2012-02-16	2015-03-31	Тева Фармасьютикал Индастриз Лтд.	N-этил-n-фенил-1,2-дигидро-4,5-дигидрокси-1-метил-2-оксо-3-хинолинкарбоксамид, его получение и применения
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）
CN104955522A (zh)	2012-11-07	2015-09-30	梯瓦制药工业有限公司	拉喹莫德胺盐
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
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WO2014153145A2 (fr)	2013-03-14	2014-09-25	Teva Pharmaceutical Industries Ltd.	Cristaux de sodium de laquinimod et procédé amélioré pour leur fabrication
WO2015168103A1 (fr)	2014-04-29	2015-11-05	Teva Pharmaceutical Industries Ltd.	Laquinimod pour le traitement de patients atteints de sclérose en plaques récurrente rémittente (sep-rr) chez ayant un degré d'incapacité élevé
WO2016042112A1 (fr)	2014-09-23	2016-03-24	Active Biotech Ab	Quinoléine carboxamides destinées à être utilisées dans le traitement du myélome multiple
ES2663836T3 (es)	2014-11-19	2018-04-17	Active Biotech Ab	Carboxamidas de quinolina para su uso en el tratamiento de leucemia
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WO2021175924A1 (fr)	2020-03-03	2021-09-10	Active Biotech Ab	Tasquinimod ou sel pharmaceutiquement acceptable de celui-ci destiné à être utilisé en polythérapie
CA3179303A1 (fr) *	2020-05-21	2021-11-25	Darren Orton	Inhibiteurs de notch et leurs utilisations
US20230293512A1 (en)	2020-07-23	2023-09-21	Erasmus University Medical Center Rotterdam	S100 proteins as novel therapeutic targets in myeloproliferative neoplasms
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
WO2022248401A1 (fr)	2021-05-25	2022-12-01	Active Biotech Ab	Pluralité de particules de tasquinimod et utilisation de celles-ci
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
AU2022421214A1 (en) *	2021-12-20	2024-07-04	The Johns Hopkins University	Compounds for treatment of cancer
WO2025083549A1 (fr)	2023-10-16	2025-04-24	Sun Pharma Advanced Research Company Limited	Méthodes et combinaisons d'inhibiteurs de la voie il-23 et de modulateurs de la voie de signalisation s1p pour le traitement de maladies auto-immunes

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE52670B1 (en) *	1981-03-03	1988-01-20	Leo Ab	Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation
SU1735288A1 (ru) *	1990-03-05	1992-05-23	Харьковский государственный фармацевтический институт	Способ получени N-R-замещенных амидов 4-гидроксихинолон-2 карбоновой -3-кислоты
GB9108547D0 (en) *	1991-04-22	1991-06-05	Fujisawa Pharmaceutical Co	Quinoline derivatives
DE4120646A1 (de) *	1991-06-22	1992-12-24	Bayer Ag	7-isoindolinyl-chinolon- und naphthyridoncarbonsaeure-derivate
US5428040A (en) *	1993-08-31	1995-06-27	The Du Pont Merck Pharmaceutical Company	Carbocyclic fused-ring quinolinecarboxylic acids useful as immunosuppressive agents
SE9400810D0 (sv) *	1994-03-10	1994-03-10	Pharmacia Ab	New use of Quinoline-3-carboxamide compounds

1998
- 1998-04-27 SE SE9801474A patent/SE9801474D0/xx unknown
1999
- 1999-04-26 CA CA002329788A patent/CA2329788C/fr not_active Expired - Fee Related
- 1999-04-26 ME MEP-2000-612A patent/ME00870B/fr unknown
- 1999-04-26 IL IL13816099A patent/IL138160A0/xx active IP Right Grant
- 1999-04-26 TR TR2000/03061T patent/TR200003061T2/xx unknown
- 1999-04-26 CZ CZ20003849A patent/CZ297439B6/cs not_active IP Right Cessation
- 1999-04-26 ES ES99947036T patent/ES2188242T3/es not_active Expired - Lifetime
- 1999-04-26 HR HR20000726A patent/HRP20000726B1/xx not_active IP Right Cessation
- 1999-04-26 BR BRPI9909925-0A patent/BR9909925B1/pt not_active IP Right Cessation
- 1999-04-26 CN CN99805581A patent/CN1113057C/zh not_active Expired - Fee Related
- 1999-04-26 RU RU2000129672/04A patent/RU2197481C2/ru not_active IP Right Cessation
- 1999-04-26 JP JP2000545838A patent/JP4045069B2/ja not_active Expired - Lifetime
- 1999-04-26 WO PCT/SE1999/000676 patent/WO1999055678A1/fr not_active Ceased
- 1999-04-26 OA OA1200000301A patent/OA11547A/en unknown
- 1999-04-26 DE DE69904162T patent/DE69904162T2/de not_active Expired - Lifetime
- 1999-04-26 AU AU43013/99A patent/AU747550B2/en not_active Ceased
- 1999-04-26 PL PL99343420A patent/PL190441B1/pl unknown
- 1999-04-26 ID IDW20002183A patent/ID26277A/id unknown
- 1999-04-26 AP APAP/P/2000/001933A patent/AP1293A/en active
- 1999-04-26 NZ NZ506641A patent/NZ506641A/en not_active IP Right Cessation
- 1999-04-26 EP EP99947036A patent/EP1073639B1/fr not_active Expired - Lifetime
- 1999-04-26 AT AT99947036T patent/ATE228505T1/de active
- 1999-04-26 HU HU0102084A patent/HU227709B1/hu not_active IP Right Cessation
- 1999-04-26 EE EEP200000613A patent/EE04275B1/xx unknown
- 1999-04-26 UA UA2000085078A patent/UA60354C2/uk unknown
- 1999-04-26 DK DK99947036T patent/DK1073639T3/da active
- 1999-04-26 RS YUP-612/00A patent/RS50029B/sr unknown
- 1999-04-26 KR KR1020007011944A patent/KR100571534B1/ko not_active Expired - Fee Related
- 1999-04-26 PT PT99947036T patent/PT1073639E/pt unknown
2000
- 2000-08-30 IL IL138160A patent/IL138160A/en not_active IP Right Cessation
- 2000-08-31 IS IS5615A patent/IS2082B/is unknown
- 2000-09-01 ZA ZA200004601A patent/ZA200004601B/en unknown
- 2000-10-19 NO NO20005254A patent/NO315606B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT1073639E (pt)	2003-04-30
DE69904162D1 (de)	2003-01-09
CN1298393A (zh)	2001-06-06
HRP20000726B1 (hr)	2009-04-30
ATE228505T1 (de)	2002-12-15
CN1113057C (zh)	2003-07-02
JP2002513006A (ja)	2002-05-08
AP2000001933A0 (en)	2000-12-31
JP4045069B2 (ja)	2008-02-13
ES2188242T3 (es)	2003-06-16
HK1036618A1 (en)	2002-01-11
BR9909925B1 (pt)	2010-09-21
WO1999055678A1 (fr)	1999-11-04
AU4301399A (en)	1999-11-16
HUP0102084A3 (en)	2002-12-28
TR200003061T2 (tr)	2001-01-22
OA11547A (en)	2004-05-24
RS50029B (sr)	2008-11-28
NO20005254D0 (no)	2000-10-19
AU747550B2 (en)	2002-05-16
CZ297439B6 (cs)	2006-12-13
AP1293A (en)	2004-08-30
EP1073639A1 (fr)	2001-02-07
HU227709B1 (en)	2011-12-28
YU61200A (sh)	2003-07-07
RU2197481C2 (ru)	2003-01-27
IS5615A (is)	2000-08-31
IL138160A (en)	2006-04-10
HRP20000726A2 (en)	2001-04-30
PL343420A1 (en)	2001-08-13
ID26277A (id)	2000-12-14
CA2329788C (fr)	2004-11-23
PL190441B1 (pl)	2005-12-30
UA60354C2 (uk)	2003-10-15
EP1073639B1 (fr)	2002-11-27
NO20005254L (no)	2000-12-27
DK1073639T3 (da)	2003-03-24
IS2082B (is)	2006-02-15
ME00870B (fr)	2008-11-28
CA2329788A1 (fr)	1999-11-04
DE69904162T2 (de)	2003-08-21
EE200000613A (et)	2002-04-15
BR9909925A (pt)	2001-01-09
NZ506641A (en)	2002-03-28
NO315606B1 (no)	2003-09-29
KR100571534B1 (ko)	2006-04-14
EE04275B1 (et)	2004-04-15
HUP0102084A2 (hu)	2001-11-28
CZ20003849A3 (cs)	2001-03-14
SE9801474D0 (sv)	1998-04-27
IL138160A0 (en)	2001-10-31

Publication	Publication Date	Title
US6077851A (en)	2000-06-20	Quinoline derivatives
EP1073639B1 (fr)	2002-11-27	Derives de quinoline
EP1095021B1 (fr)	2003-09-17	Derives de quinoline
US6133285A (en)	2000-10-17	Quinoline derivatives
EP1097139B1 (fr)	2002-12-04	Derives de quinoline
US6121287A (en)	2000-09-19	Quinoline derivatives
HK1036618B (en)	2003-04-11	Quinoline derivatives
HK1035715B (en)	2004-01-16	Quinoline derivatives
MXPA00009954A (en)	2002-03-26	Quinoline derivatives
HK1035716B (en)	2003-04-11	Quinoline derivatives
MXPA01000388A (en)	2002-07-25	Quinoline derivatives