CA2786994C - Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof - Google Patents

Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof Download PDF

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CA2786994C
CA2786994C CA2786994A CA2786994A CA2786994C CA 2786994 C CA2786994 C CA 2786994C CA 2786994 A CA2786994 A CA 2786994A CA 2786994 A CA2786994 A CA 2786994A CA 2786994 C CA2786994 C CA 2786994C
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formula
compound
process according
trifluoromethyl
tetrahydrocyclopenta
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French (fr)
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CA2786994A1 (en
Inventor
Antonio Garrido Montalban
Daniel John Buzard
John Aldo Demattei
Tawfik Gharbaoui
Stephen Robert Johannsen
Ashwin M. Krishnan
Young Mi Kuhlman
You-An Ma
Michael John Martinelli
Suzanne Michiko Sato
Dipanjan Sengupta
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Arena Pharmaceuticals Inc
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Arena Pharmaceuticals Inc
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    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • 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
    • A61P37/02—Immunomodulators
    • 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
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
    • C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
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  • Wood Science & Technology (AREA)
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  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Urology & Nephrology (AREA)
  • Dermatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
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  • Transplantation (AREA)
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  • Obesity (AREA)
  • Pain & Pain Management (AREA)
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CA2786994A 2010-01-27 2011-01-27 Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof Active CA2786994C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US33683510P 2010-01-27 2010-01-27
US61/336,835 2010-01-27
PCT/US2011/000153 WO2011094008A1 (en) 2010-01-27 2011-01-27 Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof

Publications (2)

Publication Number Publication Date
CA2786994A1 CA2786994A1 (en) 2011-08-04
CA2786994C true CA2786994C (en) 2018-01-16

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CA2786994A Active CA2786994C (en) 2010-01-27 2011-01-27 Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof

Country Status (8)

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US (5) US8853419B2 (enExample)
EP (3) EP3378854B1 (enExample)
JP (2) JP5856980B2 (enExample)
CN (2) CN103221391B (enExample)
CA (1) CA2786994C (enExample)
ES (1) ES2937386T3 (enExample)
SG (3) SG182610A1 (enExample)
WO (1) WO2011094008A1 (enExample)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010011316A1 (en) 2008-07-23 2010-01-28 Arena Pharmaceuticals, Inc. SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS
KR101800595B1 (ko) 2008-08-27 2017-11-22 아레나 파마슈티칼스, 인크. 자가면역 및 염증성 장애의 치료에 유용한, ｓ1ｐ1 수용체 효능제로서의 치환된 트리시클릭 산 유도체
WO2011094008A1 (en) * 2010-01-27 2011-08-04 Arena Pharmaceuticals, Inc. Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof
CA2789480A1 (en) 2010-03-03 2011-09-09 Arena Pharmaceuticals, Inc. Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof
CN102659664B (zh) * 2012-03-28 2015-01-21 中国计量学院 合成分离拉洛皮兰及其类似物的方法
EP3242666B9 (en) 2015-01-06 2024-12-25 Arena Pharmaceuticals, Inc. Compound for use in treating conditions related to the s1p1 receptor
IL285890B (en) 2015-06-22 2022-07-01 Arena Pharm Inc Slate-free crystal of the arginine salt of (Ar)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-4,3,2,1-tetrahydro-cyclopent[b]indole-3-yl ) acetic acid
CN106349006B (zh) * 2016-08-26 2019-02-05 大连奇凯医药科技有限公司 3-三氟甲基苯乙腈的制备方法
MX2019009841A (es) * 2017-02-16 2020-01-30 Arena Pharm Inc Compuestos y metodos para el tratamiento de la colangitis biliar primaria.
MA47503A (fr) * 2017-02-16 2021-04-21 Arena Pharm Inc Composés et méthodes pour le traitement de maladies inflammatoires chroniques de l'intestin avec manifestations extra-intestinales
US11066422B2 (en) 2017-07-13 2021-07-20 Toray Fine Chemicals Co., Ltd. Method of producing cycloalkyl(trifluoromethyl)benzene
KR102859841B1 (ko) 2018-06-06 2025-09-12 아레나 파마슈티칼스, 인크. S1p1 수용체와 관련된 병태의 치료 방법
WO2020051378A1 (en) 2018-09-06 2020-03-12 Arena Pharmaceuticals, Inc. Compounds useful in the treatment of autoimmune and inflammatory disorders
ES2951870T3 (es) 2018-10-03 2023-10-25 Arena Pharm Inc Etrasimod para su uso en procedimientos para el tratamiento de la esclerodermia
CN109529920B (zh) * 2018-11-12 2021-11-02 山东科技大学 用于轻质烷烃异构化的负载硼化钛催化剂及其制备方法和使用方法
CN109678715B (zh) * 2018-11-28 2019-11-12 中国药科大学 2-(1-酰氧正戊基)苯甲酸与碱性氨基酸或氨基胍形成的盐、其制备方法及用途
CN118649163A (zh) * 2018-11-30 2024-09-17 艾尼纳制药公司 治疗与s1p1受体有关的病况的方法
KR20210113298A (ko) 2019-01-08 2021-09-15 아레나 파마슈티칼스, 인크. S1p₁ 수용체와 관련된 병태의 치료 방법
JP2022550458A (ja) * 2019-10-01 2022-12-01 アリーナ ファーマシューティカルズ， インコーポレイテッド Ｓ１ｐ１受容体に関連する状態を処置する方法
WO2021084068A1 (en) 2019-10-31 2021-05-06 Idorsia Pharmaceuticals Ltd Combination of a cxcr7 antagonist with an s1p1 receptor modulator
BR112022007348A2 (pt) 2019-11-20 2022-07-12 Arena Pharm Inc Métodos para tratar condições relacionadas ao receptor s1p1
CN111763148B (zh) * 2020-06-19 2022-10-28 广州大学 一种含三氟甲基的炔基环戊烯衍生物及其制备方法和应用
CN114105745B (zh) * 2020-08-28 2024-07-23 广东东阳光药业股份有限公司 辛波莫德中间体及其制备方法
WO2022099150A1 (en) * 2020-11-09 2022-05-12 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the s1p1 receptor
WO2023278141A1 (en) * 2021-07-02 2023-01-05 Arena Pharmaceuticals, Inc. Administration of a compound to individuals with hepatic impairment
EP4212156A1 (en) 2022-01-13 2023-07-19 Abivax Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a s1p receptor modulator
CN118541151A (zh) 2022-01-13 2024-08-23 艾尼纳制药公司 与激素治疗组合的用于治疗s1p1受体相关病症的伊曲莫德
WO2023214312A1 (en) 2022-05-06 2023-11-09 Arena Pharmaceuticals, Inc. Methods of treating atopic dermatitis with etrasimod
CN119330873B (zh) * 2024-11-08 2025-07-11 成都克莱蒙医药科技有限公司 一种依曲莫德中间体的制备方法

Family Cites Families (272)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL293572A (enExample) 1962-06-07
CH499528A (de) 1965-10-22 1970-11-30 Ciba Geigy Ag Verfahren zur Herstellung neuer Pyrimidine
CH480410A (de) 1967-01-09 1969-10-31 Geigy Ag J R Verfahren zur Herstellung von wasserlöslichen Azopyrimidinfarbstoffen
CA961052A (en) 1967-01-12 1975-01-14 Max Schellenbaum N-2-ethylhexyl-n'-aryl ureas and preparation containing them
US3608087A (en) 1968-06-21 1971-09-21 Merck & Co Inc Feed compositions
US3887329A (en) 1969-05-05 1975-06-03 Ciba Geigy Ag Hexamethyl phosphotriamide-dye compositions
US3686238A (en) 1970-01-19 1972-08-22 Syntex Corp Glycerol esterified with 2-naphthyl-acetic acids and fatty acids
US3852434A (en) 1970-09-11 1974-12-03 Merck & Co Inc Potentiation of ({31 ) cis-1,2-epoxypropyl)phosphonic acid and analogues thereof
US3966744A (en) 1971-01-11 1976-06-29 Syva Company Spin labeled compounds
US3690834A (en) 1971-01-11 1972-09-12 Syva Co Ligand determination with spin labeled compounds by receptor displacement
DE2106585A1 (de) 1971-02-11 1972-08-24 Farbenfabriken Bayer Ag, 5090 Leverkusen Aminothiodiazole und Thiodiazol-Azofarbstoffe
DE2226703A1 (de) 1972-05-25 1973-12-13 Schering Ag Neue tetrahydrocarbazolderivate und verfahren zu ihrer herstellung
US3966764A (en) 1972-07-10 1976-06-29 Syva Company Ligand determination of spin labeled compounds by receptor displacement-amphetamine analogs
US3849420A (en) 1972-10-20 1974-11-19 Dow Chemical Co Bis-(alkylthio-and alkylsulfonyl)-pentachloroquinolines
CH574206A5 (enExample) 1972-11-16 1976-04-15 Ciba Geigy Ag
DE2340569C2 (de) 1973-08-10 1982-12-02 Bayer Ag, 5090 Leverkusen Azofarbstoffe
AT340933B (de) 1973-08-20 1978-01-10 Thomae Gmbh Dr K Verfahren zur herstellung neuer pyrimidinderivate und ihrer saureadditionssalze
US4057559A (en) 1973-10-01 1977-11-08 American Home Products Corporation Carbazole acetic acid derivatives
US4101541A (en) 1973-12-21 1978-07-18 Ciba-Geigy Corporation 3-Cyano-1,2,4-thiadiazolyl-5-czo dyestuffs
FR2306697A1 (fr) 1975-04-10 1976-11-05 Sogeras Nouvelles pyrimidines utilisables comme medicaments antidiabetiques et hypocholesterolemiants
US4139705A (en) 1977-05-20 1979-02-13 The Dow Chemical Company Pyrazolopyrimidines
US4189579A (en) 1977-05-20 1980-02-19 The Dow Chemical Company Aminoalkylthiopurines
DE2731264A1 (de) 1977-07-11 1979-02-01 Boehringer Mannheim Gmbh Neue 1-acyl-2-cyanaziridine, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zubereitungen
JPS6038696B2 (ja) 1977-12-09 1985-09-02 コニカ株式会社 ハロゲン化銀カラ−写真感光材料
US4242507A (en) 1978-02-23 1980-12-30 Fujisawa Pharmaceutical Co., Ltd. Sulfonic acid esters
DE2831580C2 (de) 1978-07-18 1980-09-18 Boehringer Mannheim Gmbh, 6800 Mannheim Verfahren und Reagens zur Bestimmung von Glycerin
DE2906603A1 (de) 1979-02-21 1980-09-04 Boehringer Mannheim Gmbh N-substituierte aziridin-2-carbonsaeurederivate, verfahren zu deren herstellung sowie diese substanzen enthaltende arzneimittel
US4343804A (en) 1979-03-26 1982-08-10 A. H. Robins Company, Inc. 4-Amino-3-quinolinecarboxylic acids and esters-antisecretory anti-ulcer compounds
DOP1981004033A (es) 1980-12-23 1990-12-29 Ciba Geigy Ag Procedimiento para proteger plantas de cultivo de la accion fitotoxica de herbicidas.
US4476248A (en) 1983-02-28 1984-10-09 The Upjohn Company Crystallization of ibuprofen
DE3334455A1 (de) 1983-03-04 1984-09-06 Bayer Ag, 5090 Leverkusen Guanidin - derivate
US4612376A (en) 1983-03-25 1986-09-16 Fujisawa Pharmaceutical Co., Ltd. Substituted-3,4-dihydro-4-(2,4,6-trimethoxyphenylimino)-2(1H)-pyrimidones useful as cardiotonic, antihypertensive, cerebrovascular vasodilator and anti-platelet agent
ZA848275B (en) 1983-12-28 1985-08-28 Degussa New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring
DE3601196A1 (de) 1986-01-17 1987-07-23 Merck Patent Gmbh 1,4-dihydropyridine
US4810699A (en) 1987-02-20 1989-03-07 American Home Products Corporation Substituted 1,3,4,9-tetrahydropyrano[3,4,-b]indole-1-acetic acids, pharmaceutical compositions containing them, and methods for treating inflammatory conditions and for analgesic purposes using them
US4782076A (en) 1988-03-01 1988-11-01 American Home Products Corporation Substituted 2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid derivatives, composition and use
PT95692A (pt) 1989-10-27 1991-09-13 American Home Prod Processo para a preparacao de derivados de acidos indole-,indeno-,piranoindole- e tetra-hidrocarbazole-alcanoicos, ou quais sao uteis como inibidores de pla2 e da lipoxigenase
US5221678A (en) 1990-07-26 1993-06-22 Merck Frosst Canada, Inc. (quinolin-2-ylmethoxy)tetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes
DE4208254A1 (de) 1992-03-14 1993-09-16 Hoechst Ag Substituierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel und fungizid
FR2692575B1 (fr) 1992-06-23 1995-06-30 Sanofi Elf Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant.
US5998499A (en) 1994-03-25 1999-12-07 Dentsply G.M.B.H. Liquid crystalline (meth)acrylate compounds, composition and method
AU692484B2 (en) 1993-10-12 1998-06-11 Du Pont Pharmaceuticals Company 1N-alkyl-N-arylpyrimidinamines and derivatives thereof
TW530047B (en) 1994-06-08 2003-05-01 Pfizer Corticotropin releasing factor antagonists
PT781766E (pt) 1994-09-09 2004-07-30 Nippon Shinyaku Co Ltd Derivado heterociclico e medicamento
US5691364A (en) 1995-03-10 1997-11-25 Berlex Laboratories, Inc. Benzamidine derivatives and their use as anti-coagulants
US6403599B1 (en) 1995-11-08 2002-06-11 Pfizer Inc Corticotropin releasing factor antagonists
US6956047B1 (en) 1995-06-06 2005-10-18 Pfizer Inc. Corticotropin releasing factor antagonists
KR0169813B1 (ko) 1995-07-12 1999-01-15 김종인 4-아미노-3-아실나프티리딘 유도체
US5849759A (en) 1995-12-08 1998-12-15 Berlex Laboratories, Inc. Naphthyl-substituted benzimidazole derivatives as anti-coagulants
US5948786A (en) 1996-04-12 1999-09-07 Sumitomo Pharmaceuticals Company, Limited Piperidinylpyrimidine derivatives
US6060478A (en) 1996-07-24 2000-05-09 Dupont Pharmaceuticals Azolo triazines and pyrimidines
US5776967A (en) 1996-07-26 1998-07-07 American Home Products Corporation Pyranoindole inhibitors of COX--2
AR008789A1 (es) 1996-07-31 2000-02-23 Bayer Corp Piridinas y bifenilos substituidos
US5830911A (en) 1996-08-14 1998-11-03 American Home Products Corporation Pyranoindole and tetrahydrocarbazole inhibitors of COX-2
US6008234A (en) 1996-09-12 1999-12-28 Berlex Laboratories, Inc. Benzamidine derivatives substituted by cyclic amino acid and cyclic hydroxy acid derivatives and their use as anti-coagulants
NL1010018C2 (nl) 1997-09-09 1999-03-10 Duphar Int Res Chinoline en chinazoline derivaten met corticotropine releasing factor (CRF) antagonistische werking.
US6861448B2 (en) 1998-01-14 2005-03-01 Virtual Drug Development, Inc. NAD synthetase inhibitors and uses thereof
US6187777B1 (en) 1998-02-06 2001-02-13 Amgen Inc. Compounds and methods which modulate feeding behavior and related diseases
EP1105394A1 (en) 1998-08-21 2001-06-13 Du Pont Pharmaceuticals Company ISOXAZOLO 4,5-d]PYRIMIDINES AS CRF ANTAGONISTS
US6239126B1 (en) 1998-12-17 2001-05-29 American Home Products Corporation Arylpiperidine and aryl-1,2,5,6-tetra-hydropyridine urea derivatives
CZ27399A3 (cs) 1999-01-26 2000-08-16 Ústav Experimentální Botaniky Av Čr Substituované dusíkaté heterocyklické deriváty, způsob jejich přípravy, tyto deriváty pro použití jako léčiva, farmaceutická kompozice a kombinovaný farmaceutický přípravek tyto deriváty obsahující a použití těchto derivátů pro výrobu léčiv
US6267985B1 (en) 1999-06-30 2001-07-31 Lipocine Inc. Clear oil-containing pharmaceutical compositions
HRP20010795A2 (en) 1999-04-28 2003-02-28 Aventis Pharma Gmbh Di-aryl acid derivatives as ppar receptor ligands
KR20020027463A (ko) 1999-07-12 2002-04-13 우에노 도시오 스핀고신-1-인산 수용체 아고니스트 또는스핀고신-1-인산을 유효 성분으로서 함유하는 선유화 억제제
JP2003509428A (ja) 1999-09-17 2003-03-11 アボツト・ゲー・エム・ベー・ハー・ウント・コンパニー・カーゲー 治療薬としてのピラゾロピリミジン
US6921763B2 (en) 1999-09-17 2005-07-26 Abbott Laboratories Pyrazolopyrimidines as therapeutic agents
US6414002B1 (en) 1999-09-22 2002-07-02 Bristol-Myers Squibb Company Substituted acid derivatives useful as antidiabetic and antiobesity agents and method
US6506762B1 (en) 1999-09-30 2003-01-14 Neurogen Corporation Certain alkylene diamine-substituted heterocycles
US6569879B2 (en) 2000-02-18 2003-05-27 Merck & Co., Inc. Aryloxyacetic acids for diabetes and lipid disorders
US6620821B2 (en) 2000-06-15 2003-09-16 Bristol-Myers Squibb Company HMG-CoA reductase inhibitors and method
KR20030017569A (ko) 2000-06-28 2003-03-03 테바 파마슈티컬 인더스트리즈 리미티드 카르베딜올
NZ523445A (en) 2000-06-29 2004-10-29 Abbott Lab Aryl phenylheterocyclyl sulfide derivatives and their use as cell adhesion-inhibiting anti-inflammatory and immune-suppressive agents
US6410583B1 (en) 2000-07-25 2002-06-25 Merck Frosst Canada & Co. Cyclopentanoindoles, compositions containing such compounds and methods of treatment
US20030224058A1 (en) 2002-05-24 2003-12-04 Elan Pharma International, Ltd. Nanoparticulate fibrate formulations
US7276249B2 (en) 2002-05-24 2007-10-02 Elan Pharma International, Ltd. Nanoparticulate fibrate formulations
JP4350946B2 (ja) 2000-10-31 2009-10-28 メルク エンド カムパニー インコーポレーテッド 糖尿病及び脂質異常症の治療のためのベンゾピランカルボン酸誘導体
US20020058026A1 (en) 2000-11-13 2002-05-16 Milton Hammerly HMG CoA reductase inhibitor medications combined wih CoEnzyme Q-10
AU2002223492A1 (en) 2000-11-14 2002-05-27 Neurosearch A/S Use of malaria parasite anion channel blockers for treating malaria
US20020137755A1 (en) 2000-12-04 2002-09-26 Bilodeau Mark T. Tyrosine kinase inhibitors
US6545016B1 (en) 2000-12-08 2003-04-08 3M Innovative Properties Company Amide substituted imidazopyridines
US6545017B1 (en) 2000-12-08 2003-04-08 3M Innovative Properties Company Urea substituted imidazopyridines
US6525064B1 (en) 2000-12-08 2003-02-25 3M Innovative Properties Company Sulfonamido substituted imidazopyridines
PT1355644E (pt) 2001-01-26 2006-11-30 Schering Corp Utilização de compostos azetidinona substituídos para o tratamento de sitosterolemia
WO2002064616A2 (en) 2001-01-30 2002-08-22 University Of Virgina Patent Foundation Agonists and antagonists of sphingosine-1-phosphate receptors
US7534547B2 (en) 2001-03-29 2009-05-19 Osaka Gas Company Limited Optically active compound and photosensitive resin composition
US7179817B2 (en) 2001-05-10 2007-02-20 Ono Pharmaceutical Co., Ltd. Carboxylic acid derivatives and drugs containing the same as the active ingredient
DE60223699T2 (de) 2001-09-27 2008-10-30 Kyorin Pharmaceutical Co., Ltd. Diarylsulfidderivat, dessen additionssalz und immunsuppressivum
US20070225351A1 (en) 2002-01-11 2007-09-27 Lippa Arnold S Methods and compositions for controlling body weight and appetite
ATE441654T1 (de) 2002-01-18 2009-09-15 Merck & Co Inc Edg-rezeptoragonisten
CA2472680A1 (en) 2002-01-18 2003-07-31 Merck & Co., Inc. Selective s1p1/edg1 receptor agonists
AU2003205630A1 (en) 2002-01-18 2003-07-30 The Genetics Company Inc. Beta-secretase inhibitors
CA2477423A1 (en) 2002-03-01 2003-09-12 Merck & Co., Inc. Aminoalkylphosphonates and related compounds as edg receptor agonists
US20050107345A1 (en) 2002-03-01 2005-05-19 Doherty George A. Aminoalkylphosphonates and related compounds as edg receptor agonists
DE10219435A1 (de) 2002-05-02 2003-11-13 Bayer Cropscience Ag Substituierte Pyrazolo-pyrimidin-4-one
US7057046B2 (en) 2002-05-20 2006-06-06 Bristol-Myers Squibb Company Lactam glycogen phosphorylase inhibitors and method of use
AU2003241477A1 (en) 2002-06-10 2003-12-22 Elan Pharma International, Ltd. Nanoparticulate polycosanol formulations and novel polycosanol combinations
US7199142B2 (en) 2002-06-17 2007-04-03 Merck & Co., Inc. 1-((5-aryl-1,2,4-oxadiazol-3-yl) benzyl)azetidine-3-carboxylates and 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl) pyrrolidine-3-carboxylates as edg receptor agonists
JPWO2004007472A1 (ja) 2002-07-10 2005-11-17 小野薬品工業株式会社 Ｃｃｒ４アンタゴニストおよびその医薬用途
US7241790B2 (en) 2002-07-30 2007-07-10 University Of Virginia Patent Foundation Compounds active in spinigosine 1-phosphate signaling
DE10237722A1 (de) 2002-08-17 2004-08-19 Aventis Pharma Deutschland Gmbh Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase
AU2003277576A1 (en) 2002-11-08 2004-06-07 Takeda Pharmaceutical Company Limited Receptor function controlling agent
US7098235B2 (en) 2002-11-14 2006-08-29 Bristol-Myers Squibb Co. Triglyceride and triglyceride-like prodrugs of glycogen phosphorylase inhibiting compounds
US20040110241A1 (en) 2002-12-06 2004-06-10 Segal Mark S. Materials and methods for monitoring vascular endothelial function
JO2397B1 (en) 2002-12-20 2007-06-17 ميرك شارب اند دوم كوربوريشن Terazol derivatives as beta-hydroxy steroid dihydrogenase-1 inhibitors
CA2509218C (en) 2002-12-20 2010-09-07 Merck & Co., Inc. 1-(amino)indanes and (1,2-dihydro-3-amino)-benzofurans, benzothiophenes and indoles as edg receptor agonists
CN102558155A (zh) 2003-01-14 2012-07-11 阿伦纳药品公司 作为代谢调节剂的芳基和杂芳基衍生物及其所涉及的疾病如糖尿病和高血糖症的预防和治疗
GB0301259D0 (en) 2003-01-20 2003-02-19 Novartis Ag Organic compounds
JP4505449B2 (ja) 2003-02-11 2010-07-21 アイアールエム・リミテッド・ライアビリティ・カンパニー 新規二環式化合物および組成物
KR101005171B1 (ko) 2003-02-18 2011-01-04 교린 세이야꾸 가부시키 가이샤 아미노포스폰산 유도체와 그 부가염 및 ｓ1ｐ 수용체조절제
EP1606282B1 (en) 2003-02-24 2008-11-12 Arena Pharmaceuticals, Inc. Phenyl- and pyridylpipereidinye-derivatives as modulators of glucose metabolism
AU2004234067B2 (en) 2003-04-30 2008-02-28 Novartis Ag Aminopropanol derivatives as sphingosine-1-phosphate receptor modulators
EP1628970A2 (en) 2003-04-30 2006-03-01 The Institutes of Pharmaceutical Discovery, LLC Heterocycle substituted carboxylic acids as inhibitors of protein tyrosine phosphatase-1b
EP1622860B1 (en) 2003-04-30 2012-02-29 Novartis AG AMINO-PROPANOL DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTOR MODULATORs
US7083933B1 (en) 2003-05-09 2006-08-01 Prosidion Limited Methods for identification of modulators of OSGPR116 activity
WO2004103279A2 (en) 2003-05-15 2004-12-02 Merck & Co., Inc. 3-(2-amino-1-azacyclyl)-5-aryl-1,2,4-oxadiazoles as s1p receptor agonists
WO2004104205A2 (en) * 2003-05-16 2004-12-02 Merck & Co., Inc. Enzymatic preparation of chiral indole esters
AU2004251146A1 (en) 2003-05-19 2005-01-06 Irm, Llc Immunosuppressant compounds and compositions
MY150088A (en) 2003-05-19 2013-11-29 Irm Llc Immunosuppressant compounds and compositions
SI1638551T1 (sl) 2003-05-19 2012-04-30 Irm Llc Imunosupresivne spojine in sestavki
CA2524027C (en) 2003-05-19 2013-03-19 Irm Llc Immunosuppressant compounds and compositions
GB0313612D0 (en) 2003-06-12 2003-07-16 Novartis Ag Organic compounds
AR045047A1 (es) 2003-07-11 2005-10-12 Arena Pharm Inc Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
WO2005007658A2 (en) 2003-07-14 2005-01-27 Arena Pharmaceuticals, Inc. Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
JPWO2005012221A1 (ja) 2003-08-04 2006-09-14 小野薬品工業株式会社 ジフェニルエーテル化合物、その製造方法および用途
EP1660449B1 (en) 2003-08-28 2009-11-18 Novartis AG Aminopropanol derivatives
CN1874991A (zh) 2003-08-29 2006-12-06 小野药品工业株式会社 能够结合s1p受体的化合物及其药物用途
US7732442B2 (en) 2003-09-05 2010-06-08 Ono Pharmaceutical Co., Ltd. Chemokine receptor antagonist and medical use thereof
JP2007528872A (ja) * 2003-10-01 2007-10-18 メルク　エンド　カムパニー　インコーポレーテッド Ｓ１ｐ受容体アゴニストとしての３，５−アリール置換、ヘテロアリール置換またはシクロアルキル置換された１，２，４−オキサジアゾール化合物
US7638637B2 (en) 2003-11-03 2009-12-29 University Of Virginia Patent Foundation Orally available sphingosine 1-phosphate receptor agonists and antagonists
JPWO2005044780A1 (ja) 2003-11-10 2007-05-17 杏林製薬株式会社 アミノカルボン酸誘導体とその付加塩及びｓ１ｐ受容体調節剤
CA2547198A1 (en) 2003-12-17 2005-06-30 Merck & Co., Inc. (3,4-disubstituted)propanoic carboxylates as s1p (edg) receptor agonists
GB0329498D0 (en) 2003-12-19 2004-01-28 Novartis Ag Organic compounds
US7875745B2 (en) 2003-12-19 2011-01-25 Ono Pharmaceutical Co., Ltd. Compounds having lysophosphatidic acid receptor antagonism and uses thereof
GB0401332D0 (en) * 2004-01-21 2004-02-25 Novartis Ag Organic compounds
EP1745034A1 (en) 2004-02-11 2007-01-24 Amgen Inc. Vanilloid receptor ligands and their use in treatments
TWI355934B (en) 2004-02-24 2012-01-11 Sankyo Co Pharmaceutical composition for treatment or prophy
TW200538433A (en) 2004-02-24 2005-12-01 Irm Llc Immunosuppressant compounds and compositiions
EP1718604A4 (en) 2004-02-24 2008-02-13 Irm Llc COMPOUNDS AND COMPOSITIONS OF IMMUNOSUPPRESSANTS
CA2558278A1 (en) 2004-03-05 2005-09-15 Banyu Pharmaceutical Co., Ltd. Diaryl-substituted five-membered heterocycle derivative
GB0405289D0 (en) 2004-03-09 2004-04-21 Novartis Ag Organic compounds
CN1942440B (zh) 2004-04-02 2011-09-14 默沙东公司 用于制备环烷基并吲哚衍生物的不对称氢化方法
DK1756084T3 (da) 2004-06-04 2009-03-23 Arena Pharm Inc Substituerede aryl- og heteroarylderivater som modulatorer af metabolisme og forebyggelse og behandling af forstyrrelser beslægtet dermed
WO2005123677A1 (en) 2004-06-16 2005-12-29 Actelion Pharmaceuticals Ltd 4-carbonyl substituted 1,1,2-trimethyl-1a,4,5,5a-tetrahydro-1h-4-aza-cyclopropa'a!pentalene derivatives as agonists for the g-protein-coupled receptor s1p1/edg1 and immunosuppressive agents
JP5315611B2 (ja) 2004-06-23 2013-10-16 小野薬品工業株式会社 Ｓ１ｐ受容体結合能を有する化合物およびその用途
CN101014329B (zh) 2004-07-16 2010-09-08 杏林制药株式会社 用于对器官或组织的移植的排异反应或骨髓移植的移植物抗宿主反应预防或治疗的药物组合物
JP2007284350A (ja) 2004-07-27 2007-11-01 Takeda Chem Ind Ltd 糖尿病治療剤
WO2006010379A1 (en) 2004-07-29 2006-02-02 Actelion Pharmaceuticals Ltd. Novel thiophene derivatives as immunosuppressive agents
TW200611687A (en) 2004-07-29 2006-04-16 Sankyo Co Pharmaceutical compositions used for immunosuppressant
WO2006013948A1 (ja) 2004-08-04 2006-02-09 Taisho Pharmaceutical Co., Ltd. トリアゾール誘導体
US20060223866A1 (en) 2004-08-13 2006-10-05 Praecis Pharmaceuticals, Inc. Methods and compositions for modulating sphingosine-1-phosphate (S1P) receptor activity
US7241812B2 (en) 2004-08-13 2007-07-10 Praecis Pharmaceuticals, Inc. Methods and compositions for modulating sphingosine-1-phosphate (S1P) receptor activity
CN101035528A (zh) 2004-09-23 2007-09-12 惠氏公司 治疗丙型肝炎病毒感染的咔唑和环戊二烯并吲哚衍生物
AU2005295080A1 (en) 2004-10-12 2006-04-20 Transition Therapeutics Inc. Compounds and methods of treating insulin resistance and cardiomyopathy
CA2583681A1 (en) 2004-10-22 2006-05-04 Merck & Co., Inc. 2-(aryl)azacyclylmethyl carboxylates, sulfonates, phosphonates, phosphinates and heterocycles as s1p receptor agonists
PT1650186E (pt) 2004-10-22 2008-09-16 Bioprojet Soc Civ Novos derivados de ácidos dicarboxílicos
AU2005307718A1 (en) 2004-11-18 2006-05-26 The Institutes For Pharmaceutical Discovery, Llc Heterocycle substituted carboxylic acids for the treatment of diabetes
WO2006057448A1 (ja) 2004-11-26 2006-06-01 Takeda Pharmaceutical Company Limited アリールアルカン酸誘導体
WO2006063033A2 (en) 2004-12-06 2006-06-15 University Of Virginia Patent Foundation Aryl amide sphingosine 1-phosphate analogs
WO2006064744A1 (ja) 2004-12-13 2006-06-22 Daiichi Sankyo Company, Limited 糖尿病の治療のための医薬組成物
EP2371811B1 (en) 2004-12-13 2014-10-08 Ono Pharmaceutical Co., Ltd. Azetidinecarboxylic acid derivative and medicinal use thereof
DOP2006000008A (es) 2005-01-10 2006-08-31 Arena Pharm Inc Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1
MY148521A (en) 2005-01-10 2013-04-30 Arena Pharm Inc Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto
DOP2006000010A (es) 2005-01-10 2006-07-31 Arena Pharm Inc Procedimiento para preparar eteres aromáticos
DOP2006000009A (es) 2005-01-13 2006-08-15 Arena Pharm Inc Procedimiento para preparar eteres de pirazolo [3,4-d] pirimidina
US7914859B2 (en) 2005-01-25 2011-03-29 Merck Patent Gmbh Mesogenic compounds, liquid crystal medium and liquid crystal display
EP1685841A1 (en) 2005-01-31 2006-08-02 Bayer Health Care Aktiengesellschaft Prevention and treatment of thromboembolic disorders
JP2008530135A (ja) 2005-02-14 2008-08-07 ユニバーシティ オブ バージニア パテント ファンデーション アミノ基およびフェニル基で置換されたシクロアルカンならびに５員の複素環を含むスフィンゴシン＝１−リン酸アゴニスト
ES2370791T3 (es) 2005-03-23 2011-12-22 Actelion Pharmaceuticals Ltd. Nuevos derivados de tiofeno como agonistas del receptor de esfingosina-1-fosfato-1.
RU2404178C2 (ru) 2005-03-23 2010-11-20 Актелион Фармасьютиклз Лтд Новые производные тиофена в качестве агонистов рецептора сфингозин-1-фосфата-1
EP1863787B1 (en) 2005-03-23 2011-05-25 Actelion Pharmaceuticals Ltd. Hydogrenated benzo[c]thiophene derivatives as immunomodulators
EP1893591A1 (en) 2005-06-08 2008-03-05 Novartis AG POLYCYCLIC OXADIAZOLES OR I SOXAZOLES AND THEIR USE AS SlP RECEPTOR LIGANDS
TWI418350B (zh) 2005-06-24 2013-12-11 Sankyo Co 含有ｐｐａｒ調節劑之醫藥組成物的用途
CN101203503B (zh) 2005-06-24 2011-12-28 埃科特莱茵药品有限公司 新颖噻吩衍生物
AU2006264651A1 (en) 2005-06-30 2007-01-11 Prosidion Limited G-protein coupled receptor agonists
US20070060573A1 (en) 2005-08-10 2007-03-15 Lars Wortmann Acyltryptophanols
JP2009506046A (ja) 2005-08-23 2009-02-12 アイアールエム・リミテッド・ライアビリティ・カンパニー 免疫抑制剤化合物および組成物
NZ565898A (en) 2005-09-16 2010-07-30 Arena Pharm Inc Modulators of metabolism and the treatment of disorders related thereto
JPWO2007037196A1 (ja) 2005-09-29 2009-04-09 山本化成株式会社 インドリン系化合物及びその製造方法
PT1932522E (pt) 2005-10-07 2012-06-26 Kyorin Seiyaku Kk Agente terapêutico para doenças do fígado contendo, como princípio activo, um derivado de 2- amino-1,3-propanodiol
AR057894A1 (es) 2005-11-23 2007-12-26 Actelion Pharmaceuticals Ltd Derivados de tiofeno
JP2009520688A (ja) 2005-11-23 2009-05-28 エピックス デラウェア， インコーポレイテッド Ｓ１ｐ受容体調節化合物およびそれらの使用
TWI404706B (zh) 2006-01-11 2013-08-11 Actelion Pharmaceuticals Ltd 新穎噻吩衍生物
TW200736234A (en) 2006-01-17 2007-10-01 Astrazeneca Ab Chemical compounds
WO2007083182A2 (en) 2006-01-19 2007-07-26 Orchid Research Laboratories Limited Novel heterocycles
BRPI0706725A2 (pt) 2006-01-24 2011-04-05 Actelion Pharmaceuticals Ltda Composto de sais do mesmo , composição farmacêutica , e , uso de um composto
GB0601744D0 (en) 2006-01-27 2006-03-08 Novartis Ag Organic compounds
TWI389683B (zh) 2006-02-06 2013-03-21 Kyorin Seiyaku Kk A therapeutic agent for an inflammatory bowel disease or an inflammatory bowel disease treatment using a 2-amino-1,3-propanediol derivative as an active ingredient
JP2009526073A (ja) 2006-02-09 2009-07-16 ユニバーシティ オブ バージニア パテント ファンデーション 二環式スフィンゴシン−１−リン酸受容体アナログ
TW200806611A (en) 2006-02-09 2008-02-01 Daiichi Seiyaku Co Novel amidopropionic acid derivatives and medicine containing the same
US20070191371A1 (en) 2006-02-14 2007-08-16 Kalypsys, Inc. Heterocyclic modulators of ppar
CN101460458A (zh) 2006-02-15 2009-06-17 阿勒根公司 具有1－磷酸－鞘氨醇(s1p)受体拮抗剂生物活性的带芳基或者杂芳基基团的吲哚－3－羧酸的酰胺、酯、硫代酰胺和硫羟酸酯化合物
EP1984334B1 (en) 2006-02-15 2014-04-09 Allergan, Inc. Indole-3-carboxylic acid amide, ester, thioamide and thiol ester compounds bearing aryl or heteroaryl groups having sphingosine-1-phosphate (s1p) receptor antagonist biological activity
WO2007098474A1 (en) 2006-02-21 2007-08-30 University Of Virginia Patent Foundation Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists
US7649098B2 (en) 2006-02-24 2010-01-19 Lexicon Pharmaceuticals, Inc. Imidazole-based compounds, compositions comprising them and methods of their use
JP2009530281A (ja) 2006-03-14 2009-08-27 アムジエン・インコーポレーテツド 代謝障害の治療に有用である二環式カルボン酸誘導体
AR060050A1 (es) 2006-03-21 2008-05-21 Epix Delaware Inc Compuestos moduladores del receptor de s1p y uso de los mismos
JP2007262009A (ja) * 2006-03-29 2007-10-11 Dai Ichi Seiyaku Co Ltd ヘテロアリール低級カルボン酸誘導体
PT2003132E (pt) 2006-04-03 2014-05-26 Astellas Pharma Inc Derivados de oxadiazole como agonistas dos s1p1
GB0607389D0 (en) 2006-04-12 2006-05-24 Novartis Ag Organic compounds
JPWO2007129745A1 (ja) 2006-05-09 2009-09-17 第一三共株式会社 ヘテロアリールアミド低級カルボン酸誘導体
BRPI0711358A2 (pt) 2006-05-09 2011-09-27 Pfizer Prod Inc derivados do ácido cicloalquilamino e suas composições farmacêuticas
WO2007129473A1 (ja) 2006-05-09 2007-11-15 Daiichi Sankyo Company, Limited 二環性アリール誘導体
TW200811147A (en) 2006-07-06 2008-03-01 Arena Pharm Inc Modulators of metabolism and the treatment of disorders related thereto
TW200811140A (en) 2006-07-06 2008-03-01 Arena Pharm Inc Modulators of metabolism and the treatment of disorders related thereto
EP2046766A1 (en) 2006-08-01 2009-04-15 Praecis Pharmaceuticals Incorporated Agonists of the sphingosine- 1- phosphate receptor (slp)
TW200823182A (en) 2006-08-01 2008-06-01 Praecis Pharm Inc Chemical compounds
EP2099768A2 (en) 2006-08-04 2009-09-16 Praecis Pharmaceuticals Incorporated Agonists of the sphingosine-1-phosphate receptor
MY152176A (en) 2006-08-08 2014-08-15 Kyorin Seiyaku Kk Amino phosphate derivative and s1p receptor modulator having same as an active ingredient
WO2008024196A1 (en) 2006-08-24 2008-02-28 Praecis Pharmaceuticals Incorporated Chemical compounds
JP2009269819A (ja) 2006-08-25 2009-11-19 Asahi Kasei Pharma Kk アミン化合物
SI2069336T1 (sl) 2006-09-07 2013-03-29 Actelion Pharmaceuticals Ltd. Derivati piridin-4-ila kot imunomodulirna sredstva
TWI408139B (zh) 2006-09-07 2013-09-11 Actelion Pharmaceuticals Ltd 新穎噻吩衍生物
BRPI0716815A2 (pt) 2006-09-07 2013-11-05 Allergan Inc Co posto heteroatomáticos tendo atividade biológia agonista e/ou antagonista de receptor de esfinfosina-1-fosfato (s1p)
CN101511783A (zh) 2006-09-08 2009-08-19 诺瓦提斯公司 用于治疗淋巴细胞相互作用介导的疾病的n-联芳(杂)芳基磺酰胺衍生物
KR20090051774A (ko) 2006-09-21 2009-05-22 액테리온 파마슈티칼 리미티드 페닐 유도체 및 면역조절제로서 이들의 용도
JP5330260B2 (ja) 2006-12-06 2013-10-30 スミスクライン ビーチャム コーポレーション 二環式化合物ならびに抗糖尿病薬としての使用
KR20090095648A (ko) 2006-12-15 2009-09-09 아보트 러보러터리즈 신규한 옥사디아졸 화합물
GB0625648D0 (en) 2006-12-21 2007-01-31 Glaxo Group Ltd Compounds
AR064650A1 (es) 2006-12-21 2009-04-15 Abbott Lab Compuestos agonistas y antagonistas del receptor de esfingosina-1-fosfato
JO2701B1 (en) 2006-12-21 2013-03-03 جلاكسو جروب ليميتد Vehicles
GB0625647D0 (en) * 2006-12-21 2007-01-31 Glaxo Group Ltd Compounds
EP2125723A1 (en) 2007-01-11 2009-12-02 Allergan, Inc. 6-substituted indole-3-carboxylic acid amide compounds having sphingosine-1-phosphate (s1p) receptor antagonist biological activity
WO2008091967A1 (en) 2007-01-26 2008-07-31 Smithkline Beecham Corporation Chemical compounds
WO2008097819A2 (en) 2007-02-05 2008-08-14 Smithkline Beecham Corporation Chemical compounds
AU2008227979B2 (en) 2007-03-16 2014-02-06 Actelion Pharmaceuticals Ltd Amino- pyridine derivatives as S1P1 /EDG1 receptor agonists
CA2679980A1 (en) 2007-03-21 2007-09-27 Epix Pharmaceuticals, Inc. S1p receptor modulating compounds and use thereof
DE602008005285D1 (de) 2007-04-19 2011-04-14 Glaxo Group Ltd Oxadiazolsubstituierte indazolderivate zur verwendung als sphingosin-1-phosphat (s1p) -agonisten
EP2014653A1 (en) 2007-06-15 2009-01-14 Bioprojet Novel dicarboxylic acid derivatives as S1P1 receptor agonists
US20090069288A1 (en) 2007-07-16 2009-03-12 Breinlinger Eric C Novel therapeutic compounds
WO2009019506A1 (en) 2007-08-03 2009-02-12 Astrazeneca Ab Heterocyclyc sulfonamides having edg-1 antagonistic activity
EP2183224B1 (en) 2007-08-08 2013-11-06 Merck Serono S.A. 6-amino-pyrimidine-4-carboxamide derivatives and related compounds which bind to the sphingosine 1-phosphate (s1p) receptor for the treatment of multiple sclerosis
CA2697551C (en) 2007-09-20 2013-03-12 Irm Llc Piperidine derivatives as modulators of gpr119 activity
TW200930368A (en) 2007-11-15 2009-07-16 Astrazeneca Ab Bis-(sulfonylamino) derivatives in therapy
EP2225201A2 (en) 2007-11-28 2010-09-08 Synta Pharmaceuticals Corp. Polymorphs of n-malonyl-bis(n'-methyl-n'-thiobenzoylhydrazide)
WO2009078983A1 (en) 2007-12-18 2009-06-25 Arena Pharmaceuticals, Inc. Tetrahydrocyclopenta[b]indol-3-yl carboxylic acid derivatives useful in the treatment of autoimmune and inflammatory disorders
CA2711887A1 (en) 2008-01-25 2009-07-30 Arena Pharmaceuticals, Inc. Dihydro-1h-pyrrolo [1,2-a] indol-1-yl carboxylic derivatives which act as s1p1 agonists
AR070398A1 (es) 2008-02-22 2010-03-31 Gruenenthal Chemie Derivados sustituidos de indol
EP2258040A2 (en) 2008-02-28 2010-12-08 Solar Roofing Systems, Inc. Photovoltaic roofing tile with fire suppression
AU2009227629B2 (en) 2008-03-17 2014-09-04 Laboratoires Juvise Pharmaceuticals Dosing regimen for a selective S1P1 receptor agonist
MY156381A (en) 2008-05-14 2016-02-15 Scripps Research Inst Novel modulators of sphingosine phosphate receptors
WO2009151621A1 (en) 2008-06-13 2009-12-17 Arena Pharmaceuticals, Inc. Substituted (1, 2, 4-0xadiaz0l-3-yl) indolin-1-yl carboxylic acid derivatives useful as s1p1 agonists
WO2009151626A1 (en) 2008-06-13 2009-12-17 Arena Pharmaceuticals, Inc. Substituted (1, 2, 4-0xadiaz0l-3-yl) indolin-1-yl carboxylic acid derivatives useful as s1p1 agonists
WO2010011316A1 (en) 2008-07-23 2010-01-28 Arena Pharmaceuticals, Inc. SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS
KR101800595B1 (ko) 2008-08-27 2017-11-22 아레나 파마슈티칼스, 인크. 자가면역 및 염증성 장애의 치료에 유용한, ｓ1ｐ1 수용체 효능제로서의 치환된 트리시클릭 산 유도체
NZ593427A (en) 2008-12-22 2013-11-29 Novartis Ag Dosage regimen of an s1p receptor agonist
HUE026869T2 (en) 2008-12-22 2016-08-29 Novartis Ag Dosage regimen for fingolimod for the treatment of multiple sclerosis
CN102387704A (zh) 2009-02-10 2012-03-21 雅培制药有限公司 S1p5受体的激动剂和拮抗剂，和其用法
WO2011005290A1 (en) 2009-06-23 2011-01-13 Arena Pharmaceuticals, Inc. Disubstituted oxadiazole derivatives useful in the treatment of autoimmune and inflammatory disorders
WO2011005295A1 (en) 2009-06-24 2011-01-13 Arena Pharmaceuticals, Inc. Modulators of the sphingosine-1-phosphate (s1p) receptor useful for the treatment of disorders related thereto
ES2759949T3 (es) 2009-10-29 2020-05-12 Bristol Myers Squibb Co Compuestos heterocíclicos tricíclicos
US8299059B2 (en) 2009-10-30 2012-10-30 Eli Lilly And Company Crystalline compound and a process for its preparation
US8440693B2 (en) 2009-12-22 2013-05-14 Novartis Ag Substituted isoquinolinones and quinazolinones
WO2011079969A1 (en) 2009-12-30 2011-07-07 Medichem S.A. A 1-(1h-1,2,4-triazol-1-yl)butan-2-ol derivative for pharmaceutical use, and the use of a 1-(1h-1,2,4-triazol-1-yl)butan-2-ol derivative with substantially undefined crystal shape for preparing said 1-(1h-1,2,4-triazol-1-yl)butan-2-ol derivative
WO2011094008A1 (en) * 2010-01-27 2011-08-04 Arena Pharmaceuticals, Inc. Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof
CA2789480A1 (en) 2010-03-03 2011-09-09 Arena Pharmaceuticals, Inc. Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof
US20130023494A1 (en) 2010-04-06 2013-01-24 Arena Pharmaceuticals, Inc. Modulators of the gpr119 receptor and the treatment of disorders related thereto
JP2013533286A (ja) 2010-07-30 2013-08-22 セントルイス ユニバーシティ 疼痛を治療する方法
BR112013008100A2 (pt) 2010-09-22 2016-08-09 Arena Pharm Inc "moduladores do receptor de gpr19 e o tratamento de distúrbios relacionados a eles."
EP2672823B1 (en) 2011-02-07 2016-08-24 Biogen MA Inc. S1p modulating agents
US20140038889A1 (en) 2011-04-22 2014-02-06 Arena Pharmaceuticals, Inc. Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto
TW201345527A (zh) 2012-02-03 2013-11-16 Teva Pharma 拉喹莫德於治療對第一線抗－ＴＮＦα療法無效之克隆氏症患者之用途
US20160038506A1 (en) 2012-02-14 2016-02-11 Repros Therapeutics Inc. Selective Estrogen Receptor Modulators With Short Half-Lives and Uses Thereof
US8962888B2 (en) 2012-12-03 2015-02-24 Physical Sciences, Inc. Forming spherical crystal habit
JP5589110B1 (ja) 2013-03-08 2014-09-10 株式会社ポーラファルマ 晶癖を有する結晶及び該結晶を有効成分として含有する医薬組成物
EP3242666B9 (en) 2015-01-06 2024-12-25 Arena Pharmaceuticals, Inc. Compound for use in treating conditions related to the s1p1 receptor
IL285890B (en) 2015-06-22 2022-07-01 Arena Pharm Inc Slate-free crystal of the arginine salt of (Ar)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-4,3,2,1-tetrahydro-cyclopent[b]indole-3-yl ) acetic acid
MA47503A (fr) 2017-02-16 2021-04-21 Arena Pharm Inc Composés et méthodes pour le traitement de maladies inflammatoires chroniques de l'intestin avec manifestations extra-intestinales
MX2019009841A (es) 2017-02-16 2020-01-30 Arena Pharm Inc Compuestos y metodos para el tratamiento de la colangitis biliar primaria.
KR102859841B1 (ko) 2018-06-06 2025-09-12 아레나 파마슈티칼스, 인크. S1p1 수용체와 관련된 병태의 치료 방법
ES2951870T3 (es) 2018-10-03 2023-10-25 Arena Pharm Inc Etrasimod para su uso en procedimientos para el tratamiento de la esclerodermia
CN118649163A (zh) 2018-11-30 2024-09-17 艾尼纳制药公司 治疗与s1p1受体有关的病况的方法
KR20210113298A (ko) 2019-01-08 2021-09-15 아레나 파마슈티칼스, 인크. S1p₁ 수용체와 관련된 병태의 치료 방법

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