WO2007098474A1 - Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists - Google Patents

Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists Download PDF

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Publication number
WO2007098474A1
WO2007098474A1 PCT/US2007/062513 US2007062513W WO2007098474A1 WO 2007098474 A1 WO2007098474 A1 WO 2007098474A1 US 2007062513 W US2007062513 W US 2007062513W WO 2007098474 A1 WO2007098474 A1 WO 2007098474A1
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WO
WIPO (PCT)
Prior art keywords
compound
alkyl
formula
slp
hydrogen
Prior art date
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Ceased
Application number
PCT/US2007/062513
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English (en)
French (fr)
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WO2007098474A8 (en
Inventor
Kevin R. Lynch
Timothy L. Macdonald
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
UVA Licensing and Ventures Group
University of Virginia UVA
Original Assignee
University of Virginia UVA
University of Virginia Patent Foundation
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.)
Filing date
Publication date
Application filed by University of Virginia UVA, University of Virginia Patent Foundation filed Critical University of Virginia UVA
Priority to CA002641661A priority Critical patent/CA2641661A1/en
Priority to EP07757284A priority patent/EP1991535A1/en
Priority to BRPI0707957-5A priority patent/BRPI0707957A2/pt
Priority to AU2007217006A priority patent/AU2007217006A1/en
Priority to JP2008555537A priority patent/JP2009527501A/ja
Publication of WO2007098474A1 publication Critical patent/WO2007098474A1/en
Priority to IL193042A priority patent/IL193042A0/en
Priority to US12/195,606 priority patent/US20090105315A1/en
Anticipated expiration legal-status Critical
Publication of WO2007098474A8 publication Critical patent/WO2007098474A8/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • 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
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • C07F9/65306—Five-membered rings containing two nitrogen atoms
    • C07F9/65318—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 3

Definitions

  • a conformational shift is induced in the G-Protein Coupled Receptor (GPCR) when the ligand binds to that receptor, causing GDP to be replaced by GTP on the ⁇ -subunit of the associated G-proteins and subsequent release of the G-proteins into the cytoplasm
  • the ⁇ -subunit then dissociates from the ⁇ -subunit and each subunit can then associate with effector proteins, which activate second messengers leading to a cellular response.
  • the GTP on the G-proteins is hydrolyzed to GDP and the subunits of the G-proteins reassociate with each other and then with the receptor.
  • Amplification plays a major role in the general GPCR pathway.
  • the binding of one ligand to one receptor leads to the activation of many G-proteins, each capable of associating with many effector proteins leading to an amplified cellular response
  • a "functional" molecule is a molecule in a form in which it exhibits a property by which it is characterized,
  • a functional enzyme is one that exhibits the characteristic catalytic activity by which the enzyme is characterized.
  • a "therapeutically effective amount" of a compound is that amount of compound that is sufficient to provide a beneficial effect to the subject to which the compound is administered
  • arylalkyl include benzyl, phenylethyl, and the like.
  • Y is O, CH 2 , CHOH, CHF, CF 2 , or ⁇ C ⁇ ; and R 20 and R 21 are alkoxy, alkenyloxy, alkynyloxy, aryloxy,
  • Exemplary solid carriers include finely divided solids such as talc, clay, microcrystalline cellulose, silica, alumina and the like.
  • Useful liquid carriers include water, alcohols or glycols or water -alcohol/glycol blends, in which the present compounds can be dissolved or dispersed at effective levels, optionally with the aid of non-toxic surfactants.
  • Adjuvants such as fragrances and additional antimicrobial agents can be added to optimize the properties for a given use
  • the resultant liquid compositions can be applied from absorbent pads, used to impregnate bandages and other dressings, or sprayed onto the affected area using pump-type or aerosol sprayers.
  • the desired dose may conveniently be presented in a single dose or as divided doses administered at appropriate intervals, for example, as two, three, four, or more sub- doses per day
  • the sub-dose itself may be further divided, e g , into a number of discrete loosely spaced administrations; such as multiple inhalations from an insufflator or by application of a plurality of drops into the eye.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Neurosurgery (AREA)
  • Emergency Medicine (AREA)
  • Surgery (AREA)
  • Rheumatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Immunology (AREA)
  • Hospice & Palliative Care (AREA)
  • Endocrinology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/US2007/062513 2006-02-21 2007-02-21 Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists Ceased WO2007098474A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
CA002641661A CA2641661A1 (en) 2006-02-21 2007-02-21 Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists
EP07757284A EP1991535A1 (en) 2006-02-21 2007-02-21 Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as sip receptor agonists
BRPI0707957-5A BRPI0707957A2 (pt) 2006-02-21 2007-02-21 composto, e, método para prevenção ou tratamento de uma condição ou sintoma patológico em um mamìfero
AU2007217006A AU2007217006A1 (en) 2006-02-21 2007-02-21 Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as SIP receptor agonists
JP2008555537A JP2009527501A (ja) 2006-02-21 2007-02-21 Ｓ１ｐ受容体アゴニストとしてのフェニル−シクロアルキル誘導体およびフェニル−複素環誘導体
IL193042A IL193042A0 (en) 2006-02-21 2008-07-24 Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as sip receptor agonists
US12/195,606 US20090105315A1 (en) 2006-02-21 2008-08-21 Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US77530906P 2006-02-21 2006-02-21
US60/775,309 2006-02-21

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/195,606 Continuation US20090105315A1 (en) 2006-02-21 2008-08-21 Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists

Publications (2)

Publication Number Publication Date
WO2007098474A1 true WO2007098474A1 (en) 2007-08-30
WO2007098474A8 WO2007098474A8 (en) 2008-11-06

Family

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Application Number Title Priority Date Filing Date
PCT/US2007/062513 Ceased WO2007098474A1 (en) 2006-02-21 2007-02-21 Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists

Country Status (12)

Country Link
US (1) US20090105315A1 (enExample)
EP (1) EP1991535A1 (enExample)
JP (1) JP2009527501A (enExample)
KR (1) KR20080096780A (enExample)
CN (1) CN101384566A (enExample)
AU (1) AU2007217006A1 (enExample)
BR (1) BRPI0707957A2 (enExample)
CA (1) CA2641661A1 (enExample)
IL (1) IL193042A0 (enExample)
RU (1) RU2008137553A (enExample)
WO (1) WO2007098474A1 (enExample)
ZA (1) ZA200806392B (enExample)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009060278A1 (en) * 2007-11-08 2009-05-14 Pfizer Inc. Cyclobutyl carboxylic acid derivatives
US7834039B2 (en) 2006-12-15 2010-11-16 Abbott Laboratories Oxadiazole compounds
EP2120575A4 (en) * 2006-12-21 2011-04-27 Abbott Lab AGONISTS AND ANTAGONISTS OF SPHINGOSINE-1-PHOSPHATE RECEPTORS
US7951794B2 (en) 2005-06-24 2011-05-31 Actelion Pharmaceuticals Ltd. Thiophene derivatives
US7956195B2 (en) 2006-12-21 2011-06-07 Abbott Laboratories Process for the preparation and isolation of the individual stereoisomers of 1-amino, 3-substituted phenylcyclopentane-carboxylates
US8133910B2 (en) 2006-09-07 2012-03-13 Actelion Pharmaceuticals Ltd. Thiophene derivatives as S1P1/EDGE1 receptor agonists
US8217027B2 (en) 2006-12-21 2012-07-10 Abbott Laboratories Sphingosine-1-phosphate receptor agonist and antagonist compounds
US8288554B2 (en) 2006-09-08 2012-10-16 Actelion Pharmaceuticals Ltd. Pyridin-3-yl derivatives as immunomodulating agents
US8299086B2 (en) 2007-11-01 2012-10-30 Actelion Pharmaceuticals Ltd. Pyrimidine derivatives
US8410151B2 (en) 2008-03-07 2013-04-02 Actelion Pharmaceuticals Ltd Aminomethyl benzene derivatives
US8580824B2 (en) 2006-09-07 2013-11-12 Actelion Pharmaceuticals Ltd. Pyridin-4-yl derivatives as immunomodulating agents
US8592460B2 (en) 2007-03-16 2013-11-26 Actelion Pharmaceuticals Ltd. Amino-pyridine derivatives as S1P1 /EDG1 receptor agonists
US8658675B2 (en) 2009-07-16 2014-02-25 Actelion Pharmaceuticals Ltd. Pyridin-4-yl derivatives
US9085581B2 (en) 2010-03-03 2015-07-21 Arena Pharmaceuticals, Inc. Processes for the preparation of S1P1 receptor modulators and crystalline forms thereof
US9126932B2 (en) 2008-07-23 2015-09-08 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
US9133179B2 (en) 2011-01-19 2015-09-15 Actelion Pharmaceuticals Ltd. 2-methoxy-pyridin-4-yl-derivatives
US10301262B2 (en) 2015-06-22 2019-05-28 Arena Pharmaceuticals, Inc. Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compund1) for use in SIPI receptor-associated disorders
US10385043B2 (en) 2015-05-20 2019-08-20 Idorsia Pharmaceuticals Ltd Crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol
US11007175B2 (en) 2015-01-06 2021-05-18 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor
US11149292B2 (en) 2010-01-27 2021-10-19 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
US11478448B2 (en) 2017-02-16 2022-10-25 Arena Pharmaceuticals, Inc. Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations
US11534424B2 (en) 2017-02-16 2022-12-27 Arena Pharmaceuticals, Inc. Compounds and methods for treatment of primary biliary cholangitis
US11555015B2 (en) 2018-09-06 2023-01-17 Arena Pharmaceuticals, Inc. Compounds useful in the treatment of autoimmune and inflammatory disorders
US12156866B2 (en) 2018-06-06 2024-12-03 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor

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EP1827606A2 (en) 2004-12-06 2007-09-05 University Of Virginia Patent Foundation Aryl amide sphingosine 1-phosphate analogs
EP1986623A2 (en) * 2006-01-27 2008-11-05 University Of Virginia Patent Foundation Method for treatment of neuropathic pain
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
EP2097371A2 (en) * 2006-11-21 2009-09-09 University Of Virginia Patent Foundation Benzocycloheptyl analogs having sphingosine 1-phosphate receptor activity
JP2010510250A (ja) * 2006-11-21 2010-04-02 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 スフィンゴシン＝１−燐酸受容体アゴニスト活性を有するヒドリンダンアナログ
NZ576893A (en) * 2006-11-21 2012-01-12 Univ Virginia Patent Found Tetralin analogs having sphingosine 1-phosphate agonist activity
PT2342205T (pt) 2008-08-27 2016-07-28 Arena Pharm Inc Derivados de ácido tricíclico substituído como agonistas de recetor s1p1 úteis no tratamento de distúrbios autoimunes e inflamatórios
AU2011337084A1 (en) * 2010-12-03 2013-07-11 Allergan, Inc. Novel pyridine derivatives as sphingosine 1-phosphate (S1P) receptor modulators
CN107827837B (zh) * 2017-11-21 2021-09-24 苏州朗科生物技术股份有限公司 鞘氨醇-1-磷酸受体调节剂化合物及其制备方法与应用

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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
WO2006088944A1 (en) * 2005-02-14 2006-08-24 University Of Virginia Patent Foundation Sphingosine 1- phos phate agonists comprising cycloalkanes and 5 -membered heterocycles substituted by amino and phenyl groups

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Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7951794B2 (en) 2005-06-24 2011-05-31 Actelion Pharmaceuticals Ltd. Thiophene derivatives
US8580824B2 (en) 2006-09-07 2013-11-12 Actelion Pharmaceuticals Ltd. Pyridin-4-yl derivatives as immunomodulating agents
US8133910B2 (en) 2006-09-07 2012-03-13 Actelion Pharmaceuticals Ltd. Thiophene derivatives as S1P1/EDGE1 receptor agonists
US8288554B2 (en) 2006-09-08 2012-10-16 Actelion Pharmaceuticals Ltd. Pyridin-3-yl derivatives as immunomodulating agents
US7834039B2 (en) 2006-12-15 2010-11-16 Abbott Laboratories Oxadiazole compounds
EP2120575A4 (en) * 2006-12-21 2011-04-27 Abbott Lab AGONISTS AND ANTAGONISTS OF SPHINGOSINE-1-PHOSPHATE RECEPTORS
US7956195B2 (en) 2006-12-21 2011-06-07 Abbott Laboratories Process for the preparation and isolation of the individual stereoisomers of 1-amino, 3-substituted phenylcyclopentane-carboxylates
US8217027B2 (en) 2006-12-21 2012-07-10 Abbott Laboratories Sphingosine-1-phosphate receptor agonist and antagonist compounds
EP2102145A4 (en) * 2006-12-21 2014-06-18 Abbott Lab PROCESS FOR THE PREPARATION AND ISOLATION OF INDIVIDUAL STEREOISOMERS OF 1-AMINO, 3-SUBSTITUTED PHENYLCYCLOPENTAN CARBOXYLATES
US8592460B2 (en) 2007-03-16 2013-11-26 Actelion Pharmaceuticals Ltd. Amino-pyridine derivatives as S1P1 /EDG1 receptor agonists
US8299086B2 (en) 2007-11-01 2012-10-30 Actelion Pharmaceuticals Ltd. Pyrimidine derivatives
WO2009060278A1 (en) * 2007-11-08 2009-05-14 Pfizer Inc. Cyclobutyl carboxylic acid derivatives
US8410151B2 (en) 2008-03-07 2013-04-02 Actelion Pharmaceuticals Ltd Aminomethyl benzene derivatives
US9522133B2 (en) 2008-07-23 2016-12-20 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
US9126932B2 (en) 2008-07-23 2015-09-08 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
US8658675B2 (en) 2009-07-16 2014-02-25 Actelion Pharmaceuticals Ltd. Pyridin-4-yl derivatives
US11149292B2 (en) 2010-01-27 2021-10-19 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
US11674163B2 (en) 2010-01-27 2023-06-13 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
US9085581B2 (en) 2010-03-03 2015-07-21 Arena Pharmaceuticals, Inc. Processes for the preparation of S1P1 receptor modulators and crystalline forms thereof
US9133179B2 (en) 2011-01-19 2015-09-15 Actelion Pharmaceuticals Ltd. 2-methoxy-pyridin-4-yl-derivatives
US11007175B2 (en) 2015-01-06 2021-05-18 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor
US11896578B2 (en) 2015-01-06 2024-02-13 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor
US10836754B2 (en) 2015-05-20 2020-11-17 Idorsia Pharmaceuticals Ltd Crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol
US11390615B2 (en) 2015-05-20 2022-07-19 Idorsia Pharmaceuticals Ltd Crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenox
US10385043B2 (en) 2015-05-20 2019-08-20 Idorsia Pharmaceuticals Ltd Crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol
US11834443B2 (en) 2015-05-20 2023-12-05 Idorsia Pharmaceuticals Ltd Crystalline form of the compound (s)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol
US11091435B2 (en) 2015-06-22 2021-08-17 Arena Pharmaceuticals, Inc. Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3, 4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(compound1) for use in S1P1 receptor-associated disorders
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EP1991535A1 (en) 2008-11-19
KR20080096780A (ko) 2008-11-03
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IL193042A0 (en) 2009-02-11
US20090105315A1 (en) 2009-04-23
ZA200806392B (en) 2009-06-24
WO2007098474A8 (en) 2008-11-06
JP2009527501A (ja) 2009-07-30
CA2641661A1 (en) 2007-08-30
CN101384566A (zh) 2009-03-11
BRPI0707957A2 (pt) 2011-05-17
AU2007217006A1 (en) 2007-08-30

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