CA2730843A1 - Oxazolopyrimidines as edg-1 receptor agonists - Google Patents
Oxazolopyrimidines as edg-1 receptor agonists Download PDFInfo
- Publication number
- CA2730843A1 CA2730843A1 CA2730843A CA2730843A CA2730843A1 CA 2730843 A1 CA2730843 A1 CA 2730843A1 CA 2730843 A CA2730843 A CA 2730843A CA 2730843 A CA2730843 A CA 2730843A CA 2730843 A1 CA2730843 A1 CA 2730843A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- chosen
- ring
- phenyl
- optionally substituted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
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- 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 title claims abstract description 46
- 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 title claims abstract description 46
- BRIOKNPDCPJCOD-UHFFFAOYSA-N [1,3]oxazolo[5,4-d]pyrimidine Chemical class N1=CN=C2OC=NC2=C1 BRIOKNPDCPJCOD-UHFFFAOYSA-N 0.000 title abstract description 17
- 239000000018 receptor agonist Substances 0.000 title description 5
- 229940044601 receptor agonist Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 339
- 238000000034 method Methods 0.000 claims abstract description 64
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 201000010099 disease Diseases 0.000 claims abstract description 24
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
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- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims abstract description 9
- -1 cyano, hydroxycarbonyl Chemical group 0.000 claims description 502
- 125000001424 substituent group Chemical group 0.000 claims description 460
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 400
- 229910052736 halogen Inorganic materials 0.000 claims description 228
- 150000002367 halogens Chemical class 0.000 claims description 228
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 228
- 125000004432 carbon atom Chemical group C* 0.000 claims description 196
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 156
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 152
- 125000004043 oxo group Chemical group O=* 0.000 claims description 142
- 125000005842 heteroatom Chemical group 0.000 claims description 139
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 137
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 136
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 96
- 229920006395 saturated elastomer Polymers 0.000 claims description 90
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 82
- 125000002950 monocyclic group Chemical group 0.000 claims description 82
- 150000003839 salts Chemical class 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 74
- 125000004434 sulfur atom Chemical group 0.000 claims description 72
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 70
- 239000011737 fluorine Substances 0.000 claims description 70
- 229910052731 fluorine Inorganic materials 0.000 claims description 70
- 125000002619 bicyclic group Chemical group 0.000 claims description 65
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 58
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 53
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 50
- 239000012453 solvate Substances 0.000 claims description 49
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 47
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 39
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- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 29
- 229910052740 iodine Inorganic materials 0.000 claims description 27
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000000524 functional group Chemical group 0.000 claims description 14
- 239000002243 precursor Substances 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
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- 125000002393 azetidinyl group Chemical group 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
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- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
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- 206010063837 Reperfusion injury Diseases 0.000 claims description 4
- 208000029078 coronary artery disease Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- NTNQXMJNHOKTBP-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)-7-propoxy-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]phenol Chemical compound N=1C=2OC(C=3C=C(O)C=CC=3)=NC=2C(OCCC)=NC=1CN1CCOCC1 NTNQXMJNHOKTBP-UHFFFAOYSA-N 0.000 claims description 3
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- YCTDREDEOBUKJL-QFIPXVFZSA-N (2s)-1-[2-[4-[5-[(4-chlorophenyl)methyl]-7-propoxy-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy]acetyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C=2OC(C=3C=C(C)C(OCC(=O)N4[C@@H](CCC4)C(O)=O)=C(C)C=3)=NC=2C(OCCC)=NC=1CC1=CC=C(Cl)C=C1 YCTDREDEOBUKJL-QFIPXVFZSA-N 0.000 claims description 2
- PVIXWTJXXCYQDL-UHFFFAOYSA-N 1-[(5-tert-butyl-1h-1,2,4-triazol-3-yl)sulfonyl]-3-[4-[5-[(4-chlorophenyl)methyl]-7-ethoxy-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy]propan-2-ol Chemical compound N=1C=2OC(C=3C=C(C)C(OCC(O)CS(=O)(=O)C=4NC(=NN=4)C(C)(C)C)=C(C)C=3)=NC=2C(OCC)=NC=1CC1=CC=C(Cl)C=C1 PVIXWTJXXCYQDL-UHFFFAOYSA-N 0.000 claims description 2
- BUOMRAHIKNJNFF-UHFFFAOYSA-N 2-(2-chloropyridin-4-yl)-5-(morpholin-4-ylmethyl)-7-propoxy-[1,3]oxazolo[5,4-d]pyrimidine Chemical compound N=1C=2OC(C=3C=C(Cl)N=CC=3)=NC=2C(OCCC)=NC=1CN1CCOCC1 BUOMRAHIKNJNFF-UHFFFAOYSA-N 0.000 claims description 2
- GSLFEOCFQNMHIR-UHFFFAOYSA-N 2-(3-methylphenyl)-5-(1-phenylethyl)-7-propoxy-[1,3]oxazolo[5,4-d]pyrimidine Chemical compound N=1C=2C(OCCC)=NC(C(C)C=3C=CC=CC=3)=NC=2OC=1C1=CC=CC(C)=C1 GSLFEOCFQNMHIR-UHFFFAOYSA-N 0.000 claims description 2
- BUIWDHZLIJXXJJ-UHFFFAOYSA-N 3-[[3-[4-[5-[(4-chlorophenyl)methyl]-7-propoxy-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy]-2-hydroxypropyl]amino]propanoic acid Chemical compound N=1C=2OC(C=3C=C(C)C(OCC(O)CNCCC(O)=O)=C(C)C=3)=NC=2C(OCCC)=NC=1CC1=CC=C(Cl)C=C1 BUIWDHZLIJXXJJ-UHFFFAOYSA-N 0.000 claims description 2
- VFGYOMXYUKHRHX-UHFFFAOYSA-N 4-[5-[(4-chlorophenyl)methyl]-7-ethoxy-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]-2-fluorophenol Chemical compound N=1C=2OC(C=3C=C(F)C(O)=CC=3)=NC=2C(OCC)=NC=1CC1=CC=C(Cl)C=C1 VFGYOMXYUKHRHX-UHFFFAOYSA-N 0.000 claims description 2
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 208000002249 Diabetes Complications Diseases 0.000 claims description 2
- 208000032781 Diabetic cardiomyopathy Diseases 0.000 claims description 2
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- 206010020772 Hypertension Diseases 0.000 claims description 2
- 201000001068 Prinzmetal angina Diseases 0.000 claims description 2
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- 208000007718 Stable Angina Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
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- 230000000996 additive effect Effects 0.000 claims description 2
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- QTUVBFANSOWKJH-UHFFFAOYSA-N n-[3-[4-[5-[(4-chlorophenyl)methyl]-7-ethoxy-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-1-hydroxycyclopropane-1-carboxamide Chemical compound N=1C=2OC(C=3C=C(C)C(OCC(O)CNC(=O)C4(O)CC4)=C(C)C=3)=NC=2C(OCC)=NC=1CC1=CC=C(Cl)C=C1 QTUVBFANSOWKJH-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
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- YMLGGPGIMOBQOH-UHFFFAOYSA-N 1-[4-[5-[(4-chlorophenyl)methyl]-7-ethoxy-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy]-3-(diethylamino)propan-2-ol Chemical compound N=1C=2OC(C=3C=C(C)C(OCC(O)CN(CC)CC)=C(C)C=3)=NC=2C(OCC)=NC=1CC1=CC=C(Cl)C=C1 YMLGGPGIMOBQOH-UHFFFAOYSA-N 0.000 claims 1
- WSLWTXWTYJUZIH-UHFFFAOYSA-N 1-[4-[5-[(4-chlorophenyl)methyl]-7-ethoxy-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy]-3-morpholin-4-ylpropan-2-ol Chemical compound N=1C=2OC(C=3C=C(C)C(OCC(O)CN4CCOCC4)=C(C)C=3)=NC=2C(OCC)=NC=1CC1=CC=C(Cl)C=C1 WSLWTXWTYJUZIH-UHFFFAOYSA-N 0.000 claims 1
- BTXCDYXPJZHLSX-UHFFFAOYSA-N 2-(2-chloro-5-fluorophenyl)-5-(1,4-oxazepan-4-ylmethyl)-7-propoxy-[1,3]oxazolo[5,4-d]pyrimidine Chemical compound N=1C=2OC(C=3C(=CC=C(F)C=3)Cl)=NC=2C(OCCC)=NC=1CN1CCCOCC1 BTXCDYXPJZHLSX-UHFFFAOYSA-N 0.000 claims 1
- FNCDOJPMXOQXKC-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-(morpholin-4-ylmethyl)-7-propoxy-[1,3]oxazolo[5,4-d]pyrimidine Chemical compound N=1C=2OC(C=3C=C(F)C=CC=3)=NC=2C(OCCC)=NC=1CN1CCOCC1 FNCDOJPMXOQXKC-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
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- 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
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
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- 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
-
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08290694.2 | 2008-07-15 | ||
| EP08290694 | 2008-07-15 | ||
| PCT/EP2009/004770 WO2010006704A1 (en) | 2008-07-15 | 2009-07-02 | Oxazolopyrimidines as edg-1 receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2730843A1 true CA2730843A1 (en) | 2010-01-21 |
Family
ID=39967817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2730843A Abandoned CA2730843A1 (en) | 2008-07-15 | 2009-07-02 | Oxazolopyrimidines as edg-1 receptor agonists |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8735387B2 (https=) |
| EP (2) | EP2318415B1 (https=) |
| JP (1) | JP5449346B2 (https=) |
| KR (1) | KR20110042286A (https=) |
| CN (1) | CN102159582B (https=) |
| AR (1) | AR072496A1 (https=) |
| AU (1) | AU2009270511B2 (https=) |
| BR (1) | BRPI0915781A2 (https=) |
| CA (1) | CA2730843A1 (https=) |
| CL (1) | CL2011000071A1 (https=) |
| CO (1) | CO6331436A2 (https=) |
| IL (1) | IL210639A0 (https=) |
| MA (1) | MA32455B1 (https=) |
| MX (1) | MX2011000211A (https=) |
| NZ (1) | NZ590377A (https=) |
| RU (1) | RU2503680C2 (https=) |
| TW (1) | TW201016707A (https=) |
| UY (1) | UY31981A (https=) |
| WO (1) | WO2010006704A1 (https=) |
| ZA (1) | ZA201008786B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR079981A1 (es) | 2010-01-13 | 2012-03-07 | Sanofi Aventis | Derivados de acido carboxilico que comprenden un anillo de oxoazolopirimidina 2,5,7- sustituido |
| AR079980A1 (es) | 2010-01-13 | 2012-03-07 | Sanofi Aventis | Derivados de oxazolopirimidina sustituida en 2,5,7 |
| CN102791717B (zh) * | 2010-01-14 | 2016-03-30 | 赛诺菲 | 具有2,5-取代的噁唑并嘧啶环的羧酸衍生物 |
| DK2523960T3 (da) * | 2010-01-14 | 2014-01-20 | Sanofi Sa | Heterocykliske carboxylsyrederivater med en 2,5-substitueret oxazolopyrimidinring |
| CN102834400B (zh) * | 2010-01-14 | 2015-06-10 | 赛诺菲 | 2,5-取代的*唑并嘧啶衍生物 |
| BR122017023123B1 (pt) | 2010-03-12 | 2018-04-24 | Nippon Soda Co., Ltd. | Método para produzir derivado de picolina halogenada |
| US8580816B2 (en) * | 2011-07-07 | 2013-11-12 | Sanofi | Carboxylic acid derivatives having an oxazolo[5,4-b]pyridine ring |
| US9321787B2 (en) * | 2011-07-07 | 2016-04-26 | Sanofi | Carboxylic acid derivatives having an oxazolo[5,4-d]pyrimidine ring |
| US8735402B2 (en) * | 2011-07-07 | 2014-05-27 | Sanofi | Cycloalkyloxycarboxylic acid derivatives |
| US8907093B2 (en) | 2011-07-07 | 2014-12-09 | Sanofi | Carboxylic acid derivatives having an oxazolo[4,5-c]pyridine ring |
| WO2013163244A1 (en) * | 2012-04-26 | 2013-10-31 | Bristol-Myers Squibb Company | Imidazothiadiazole derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| LT2841437T (lt) | 2012-04-26 | 2017-09-11 | Bristol-Myers Squibb Company | Imidazotiadiazolo ir imidazopirazino dariniai, kaip proteazės aktyvuotų receptorių 4 (par4) inhibitoriai, skirti trombocitų agregacijos gydymui |
| US10577308B2 (en) | 2015-03-26 | 2020-03-03 | The Florey Institute | Sodium channel modulators |
| CN117529325A (zh) * | 2021-04-21 | 2024-02-06 | 纳特科药品有限公司 | 制备7-(吗啉基)-2-(N-哌嗪基)甲基噻吩并[2,3-c]吡啶衍生物的改进方法 |
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| US3679682A (en) * | 1970-04-23 | 1972-07-25 | Fmc Corp | CERTAIN 5H-ISOXAZOLO{8 5,4-d{9 PYRIMIDIN-4-ONES |
| CN100378107C (zh) * | 2001-05-14 | 2008-04-02 | 诺瓦提斯公司 | 唑并嘧啶和呋喃并嘧啶化合物以及它们作为抗肿瘤药物的用途 |
| US20050070506A1 (en) | 2002-01-18 | 2005-03-31 | Doherty George A. | Selective s1p1/edg1 receptor agonists |
| MXPA05010802A (es) | 2003-04-25 | 2005-12-14 | Univ Cardiff | Compuestos heterociclicos para el uso en el tratamiento de infecciones virales. |
| CA2523677A1 (en) * | 2003-04-30 | 2004-11-11 | Novartis Ag | Aminopropanol derivatives as sphingosine-1-phosphate receptor modulators |
| BRPI0410439A (pt) * | 2003-05-19 | 2006-06-06 | Irm Llc | compostos e composições imunossupressoras |
| MXPA06002618A (es) | 2003-09-09 | 2006-06-05 | Ono Pharmaceutical Co | Antagonistas del factor de liberacion de corticotropina (crf) y compuestos heterobiciclicos. |
| US7605171B2 (en) | 2003-12-17 | 2009-10-20 | Merck & Co., Inc. | (3,4-disubstituted)propanoic carboxylates as S1P (Edg) receptor agonists |
| WO2005067546A2 (en) | 2004-01-13 | 2005-07-28 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
| 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 |
| WO2006010379A1 (en) | 2004-07-29 | 2006-02-02 | Actelion Pharmaceuticals Ltd. | Novel thiophene derivatives as immunosuppressive agents |
| AU2005299851B2 (en) | 2004-10-22 | 2011-03-17 | Merck Sharp & Dohme Corp. | 2-(aryl)azacyclylmethyl carboxylates, sulfonates, phosphonates, phosphinates and heterocycles as S1P receptor agonists |
| EP1965807A4 (en) * | 2005-11-23 | 2010-10-27 | Epix Delaware Inc | S1P RECEPTOR MODULATING COMPOUNDS AND THEIR USE |
| EP1900729A1 (en) * | 2006-09-15 | 2008-03-19 | Novartis AG | Benzoxazoles and oxazolopyridines being useful as Janus kinases inhibitors |
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2009
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- 2009-07-02 AU AU2009270511A patent/AU2009270511B2/en not_active Ceased
- 2009-07-02 WO PCT/EP2009/004770 patent/WO2010006704A1/en not_active Ceased
- 2009-07-02 NZ NZ590377A patent/NZ590377A/en not_active IP Right Cessation
- 2009-07-02 KR KR1020117001113A patent/KR20110042286A/ko not_active Withdrawn
- 2009-07-02 JP JP2011517773A patent/JP5449346B2/ja not_active Expired - Fee Related
- 2009-07-02 RU RU2011105388/04A patent/RU2503680C2/ru not_active IP Right Cessation
- 2009-07-02 CA CA2730843A patent/CA2730843A1/en not_active Abandoned
- 2009-07-02 MX MX2011000211A patent/MX2011000211A/es active IP Right Grant
- 2009-07-02 CN CN200980135883.4A patent/CN102159582B/zh not_active Expired - Fee Related
- 2009-07-02 US US13/003,125 patent/US8735387B2/en not_active Expired - Fee Related
- 2009-07-02 EP EP13151034.9A patent/EP2583720A1/en not_active Withdrawn
- 2009-07-02 BR BRPI0915781A patent/BRPI0915781A2/pt not_active IP Right Cessation
- 2009-07-13 TW TW098123561A patent/TW201016707A/zh unknown
- 2009-07-13 AR ARP090102624A patent/AR072496A1/es not_active Application Discontinuation
- 2009-07-13 UY UY0001031981A patent/UY31981A/es not_active Application Discontinuation
-
2010
- 2010-12-07 ZA ZA2010/08786A patent/ZA201008786B/en unknown
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2011
- 2011-01-05 MA MA33493A patent/MA32455B1/fr unknown
- 2011-01-12 CL CL2011000071A patent/CL2011000071A1/es unknown
- 2011-01-13 IL IL210639A patent/IL210639A0/en unknown
- 2011-01-14 CO CO11003596A patent/CO6331436A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN102159582B (zh) | 2014-05-07 |
| CL2011000071A1 (es) | 2011-05-06 |
| EP2583720A1 (en) | 2013-04-24 |
| NZ590377A (en) | 2011-11-25 |
| WO2010006704A1 (en) | 2010-01-21 |
| US8735387B2 (en) | 2014-05-27 |
| AU2009270511A1 (en) | 2010-01-21 |
| RU2503680C2 (ru) | 2014-01-10 |
| JP2011527994A (ja) | 2011-11-10 |
| EP2318415A1 (en) | 2011-05-11 |
| TW201016707A (en) | 2010-05-01 |
| AU2009270511B2 (en) | 2013-07-18 |
| EP2318415B1 (en) | 2013-02-20 |
| RU2011105388A (ru) | 2012-08-20 |
| US20110190490A1 (en) | 2011-08-04 |
| MA32455B1 (fr) | 2011-07-03 |
| BRPI0915781A2 (pt) | 2015-11-10 |
| CO6331436A2 (es) | 2011-10-20 |
| ZA201008786B (en) | 2012-01-25 |
| CN102159582A (zh) | 2011-08-17 |
| UY31981A (es) | 2010-02-26 |
| IL210639A0 (en) | 2011-03-31 |
| AR072496A1 (es) | 2010-09-01 |
| KR20110042286A (ko) | 2011-04-26 |
| JP5449346B2 (ja) | 2014-03-19 |
| MX2011000211A (es) | 2011-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20150702 |