WO2007098474A1 - Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists - Google Patents
Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as s1p receptor agonists Download PDFInfo
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- 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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- Prior art keywords
- compound
- alkyl
- formula
- slp
- hydrogen
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Neurosurgery (AREA)
- Surgery (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
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 |
JP2008555537A JP2009527501A (en) | 2006-02-21 | 2007-02-21 | Phenyl-cycloalkyl derivatives and phenyl-heterocyclic derivatives as S1P receptor agonists |
AU2007217006A AU2007217006A1 (en) | 2006-02-21 | 2007-02-21 | Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as SIP receptor agonists |
BRPI0707957-5A BRPI0707957A2 (en) | 2006-02-21 | 2007-02-21 | compound, and, method for preventing or treating a pathological condition or symptom in a mammal |
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 |
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WO2007098474A1 true WO2007098474A1 (en) | 2007-08-30 |
WO2007098474A8 WO2007098474A8 (en) | 2008-11-06 |
Family
ID=38180400
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2007/062513 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 (en) |
EP (1) | EP1991535A1 (en) |
JP (1) | JP2009527501A (en) |
KR (1) | KR20080096780A (en) |
CN (1) | CN101384566A (en) |
AU (1) | AU2007217006A1 (en) |
BR (1) | BRPI0707957A2 (en) |
CA (1) | CA2641661A1 (en) |
IL (1) | IL193042A0 (en) |
RU (1) | RU2008137553A (en) |
WO (1) | WO2007098474A1 (en) |
ZA (1) | ZA200806392B (en) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009060278A1 (en) * | 2007-11-08 | 2009-05-14 | Pfizer Inc. | Cyclobutyl carboxylic acid derivatives |
EP2102145A1 (en) * | 2006-12-21 | 2009-09-23 | Abbott Laboratories | Process for the preparation and isolation of the individual stereoisomers of 1-amino, 3-substituted phenylcyclopentane carboxylates |
EP2120575A1 (en) * | 2006-12-21 | 2009-11-25 | Abbott Laboratories | Sphingosine-1 -phosphate receptor agonist and antagonist compounds |
US7834039B2 (en) | 2006-12-15 | 2010-11-16 | Abbott Laboratories | Oxadiazole compounds |
US7951794B2 (en) | 2005-06-24 | 2011-05-31 | Actelion Pharmaceuticals Ltd. | Thiophene derivatives |
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 |
Families Citing this family (9)
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MX2007006706A (en) | 2004-12-06 | 2007-10-18 | Univ Virginia | Aryl amide sphingosine 1-phosphate analogs. |
RU2008134702A (en) * | 2006-01-27 | 2010-03-10 | Юниверсити Оф Вирждиния Пэтент Фаундейшн (Us) | METHOD FOR TREATING NEUROPATHIC PAIN |
WO2007092638A1 (en) * | 2006-02-09 | 2007-08-16 | University Of Virginia Patent Foundation | Bicyclic sphingosine 1-phosphate analogs |
WO2008064337A2 (en) * | 2006-11-21 | 2008-05-29 | University Of Virginia Patent Foundation | Benzocycloheptyl analogs having sphingosine 1-phosphate receptor activity |
EP2099741A2 (en) * | 2006-11-21 | 2009-09-16 | University Of Virginia Patent Foundation | Hydrindane analogs having sphingosine 1-phosphate receptor agonist activity |
JP2010510249A (en) * | 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 | Sphingosine = 1-tetralin analog having 1-phosphate agonist activity |
BRPI0917923B1 (en) | 2008-08-27 | 2022-04-05 | Arena Pharmaceuticals Inc | Substituted tricyclic acid derivative, its composition, its use and process for preparing said composition |
BR112013013638A2 (en) * | 2010-12-03 | 2016-09-06 | Allergan Inc | pyridine derivatives as sphingosine-1-phosphate receptor modulators (s1p) |
CN107827837B (en) * | 2017-11-21 | 2021-09-24 | 苏州朗科生物技术股份有限公司 | Sphingosine-1-phosphate receptor modulator compounds, and preparation method and application thereof |
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-
2007
- 2007-02-21 RU RU2008137553/04A patent/RU2008137553A/en not_active Application Discontinuation
- 2007-02-21 AU AU2007217006A patent/AU2007217006A1/en not_active Abandoned
- 2007-02-21 KR KR1020087020312A patent/KR20080096780A/en not_active Application Discontinuation
- 2007-02-21 WO PCT/US2007/062513 patent/WO2007098474A1/en active Application Filing
- 2007-02-21 JP JP2008555537A patent/JP2009527501A/en active Pending
- 2007-02-21 EP EP07757284A patent/EP1991535A1/en not_active Withdrawn
- 2007-02-21 CN CNA2007800058918A patent/CN101384566A/en active Pending
- 2007-02-21 BR BRPI0707957-5A patent/BRPI0707957A2/en not_active IP Right Cessation
- 2007-02-21 CA CA002641661A patent/CA2641661A1/en not_active Abandoned
-
2008
- 2008-07-23 ZA ZA200806392A patent/ZA200806392B/en unknown
- 2008-07-24 IL IL193042A patent/IL193042A0/en unknown
- 2008-08-21 US US12/195,606 patent/US20090105315A1/en not_active Abandoned
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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 |
EP2102145A4 (en) * | 2006-12-21 | 2014-06-18 | Abbott Lab | Process for the preparation and isolation of the individual stereoisomers of 1-amino, 3-substituted phenylcyclopentane carboxylates |
EP2102145A1 (en) * | 2006-12-21 | 2009-09-23 | Abbott Laboratories | Process for the preparation and isolation of the individual stereoisomers of 1-amino, 3-substituted phenylcyclopentane carboxylates |
EP2120575A4 (en) * | 2006-12-21 | 2011-04-27 | Abbott Lab | Sphingosine-1 -phosphate receptor agonist and antagonist compounds |
US8217027B2 (en) | 2006-12-21 | 2012-07-10 | Abbott Laboratories | Sphingosine-1-phosphate receptor agonist and antagonist compounds |
EP2120575A1 (en) * | 2006-12-21 | 2009-11-25 | Abbott Laboratories | Sphingosine-1 -phosphate receptor agonist and antagonist compounds |
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 |
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 |
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 |
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 |
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 |
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WO2007098474A8 (en) | 2008-11-06 |
KR20080096780A (en) | 2008-11-03 |
ZA200806392B (en) | 2009-06-24 |
JP2009527501A (en) | 2009-07-30 |
BRPI0707957A2 (en) | 2011-05-17 |
AU2007217006A1 (en) | 2007-08-30 |
EP1991535A1 (en) | 2008-11-19 |
IL193042A0 (en) | 2009-02-11 |
RU2008137553A (en) | 2010-03-27 |
CA2641661A1 (en) | 2007-08-30 |
CN101384566A (en) | 2009-03-11 |
US20090105315A1 (en) | 2009-04-23 |
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