JP2010513283A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010513283A5 JP2010513283A5 JP2009541394A JP2009541394A JP2010513283A5 JP 2010513283 A5 JP2010513283 A5 JP 2010513283A5 JP 2009541394 A JP2009541394 A JP 2009541394A JP 2009541394 A JP2009541394 A JP 2009541394A JP 2010513283 A5 JP2010513283 A5 JP 2010513283A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- substituted
- compound
- phenyl
- 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.)
- Withdrawn
Links
- -1 hydrate Substances 0.000 claims description 36
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 239000000651 prodrug Substances 0.000 claims 10
- 229940002612 prodrug Drugs 0.000 claims 10
- 239000002207 metabolite Substances 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 230000000975 bioactive effect Effects 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000003944 tolyl group Chemical group 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 201000011152 Pemphigus Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000006399 methylpyrazinyl group Chemical group 0.000 claims 2
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- KZZHPWMVEVZEFG-UHFFFAOYSA-N tert-butyl n-phenylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1 KZZHPWMVEVZEFG-UHFFFAOYSA-N 0.000 claims 2
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 1
- 125000006531 (C2-C5) alkyl group Chemical group 0.000 claims 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- VDVAMDZTDPBPFB-UHFFFAOYSA-N 2-cyclopenta-2,4-dien-1-ylthiophene Chemical class C1=CC=CC1C1=CC=CS1 VDVAMDZTDPBPFB-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical class [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 208000010444 Acidosis Diseases 0.000 claims 1
- 208000026872 Addison Disease Diseases 0.000 claims 1
- 206010001324 Adrenal atrophy Diseases 0.000 claims 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 1
- 206010003645 Atopy Diseases 0.000 claims 1
- 208000004300 Atrophic Gastritis Diseases 0.000 claims 1
- 208000031212 Autoimmune polyendocrinopathy Diseases 0.000 claims 1
- 208000022106 Autoimmune polyendocrinopathy type 2 Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims 1
- 206010008909 Chronic Hepatitis Diseases 0.000 claims 1
- 208000015943 Coeliac disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000014311 Cushing syndrome Diseases 0.000 claims 1
- 206010015943 Eye inflammation Diseases 0.000 claims 1
- 208000036495 Gastritis atrophic Diseases 0.000 claims 1
- 208000007465 Giant cell arteritis Diseases 0.000 claims 1
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 201000010743 Lambert-Eaton myasthenic syndrome Diseases 0.000 claims 1
- 208000003250 Mixed connective tissue disease Diseases 0.000 claims 1
- 201000002481 Myositis Diseases 0.000 claims 1
- 208000031845 Pernicious anaemia Diseases 0.000 claims 1
- 208000005374 Poisoning Diseases 0.000 claims 1
- 206010065159 Polychondritis Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000003782 Raynaud disease Diseases 0.000 claims 1
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 1
- 208000033464 Reiter syndrome Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000001106 Takayasu Arteritis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 230000007950 acidosis Effects 0.000 claims 1
- 208000026545 acidosis disease Diseases 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000009780 autoimmune polyendocrine syndrome type 2 Diseases 0.000 claims 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 208000016644 chronic atrophic gastritis Diseases 0.000 claims 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 231100000572 poisoning Toxicity 0.000 claims 1
- 230000000607 poisoning effect Effects 0.000 claims 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims 1
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 208000002574 reactive arthritis Diseases 0.000 claims 1
- 208000009169 relapsing polychondritis Diseases 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000002889 sympathetic effect Effects 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 206010043207 temporal arteritis Diseases 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- LMDJGVPLCKWXHO-UHFFFAOYSA-N 3-[2-[4-[3-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-5-yl]phenyl]propan-2-ylamino]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(C)(C)NCCC(O)=O)=N1 LMDJGVPLCKWXHO-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- RBVKZGDWTYHGSB-UHFFFAOYSA-N methyl 3-[2-[4-[3-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-5-yl]phenyl]propan-2-ylamino]propanoate Chemical compound C1=CC(C(C)(C)NCCC(=O)OC)=CC=C1C1=NC(C=2C=C(Cl)C(OC(C)C)=CC=2)=NO1 RBVKZGDWTYHGSB-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- XSRWOPOIGSBMGY-UHFFFAOYSA-N 2-[4-[3-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-5-yl]phenyl]propan-2-amine Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(C)(C)N)=N1 XSRWOPOIGSBMGY-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- QUBVFMMPRUOGDO-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-yloxyphenyl)-5-(4-fluorophenyl)-1,2,4-oxadiazole Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NOC(C=2C=CC(F)=CC=2)=N1 QUBVFMMPRUOGDO-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- MUCYUTNGHUVNLM-UHFFFAOYSA-N 3-chloro-n'-hydroxy-4-propan-2-yloxybenzenecarboximidamide Chemical compound CC(C)OC1=CC=C(C(=N)NO)C=C1Cl MUCYUTNGHUVNLM-UHFFFAOYSA-N 0.000 description 1
- YOHVWVYGCZAYHU-UHFFFAOYSA-N 4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]benzoic acid Chemical compound CC(C)(C)OC(=O)COC1=CC=C(C(O)=O)C=C1 YOHVWVYGCZAYHU-UHFFFAOYSA-N 0.000 description 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GZJDTOYCCMEVKK-UHFFFAOYSA-N C=CC1CN(Cc(cc2)ccc2-c2n[o]c(-c3ccc(C4CCCC4)cc3)n2)C1 Chemical compound C=CC1CN(Cc(cc2)ccc2-c2n[o]c(-c3ccc(C4CCCC4)cc3)n2)C1 GZJDTOYCCMEVKK-UHFFFAOYSA-N 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- SJWCGJPMVVVRIV-UHFFFAOYSA-N OC(C1CN(Cc(cc2)ccc2-c2n[o]c(-c(cc3)ccc3-c3ccc[o]3)n2)C1)=O Chemical compound OC(C1CN(Cc(cc2)ccc2-c2n[o]c(-c(cc3)ccc3-c3ccc[o]3)n2)C1)=O SJWCGJPMVVVRIV-UHFFFAOYSA-N 0.000 description 1
- VNTDAESCEVFXGZ-UHFFFAOYSA-N OC(c(cc1)ccc1-c1n[o]c(C2CC2)n1)=O Chemical compound OC(c(cc1)ccc1-c1n[o]c(C2CC2)n1)=O VNTDAESCEVFXGZ-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- XLFBWNXAWYIGNI-UHFFFAOYSA-N phenol;triphenylphosphane Chemical compound OC1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 XLFBWNXAWYIGNI-UHFFFAOYSA-N 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87525106P | 2006-12-15 | 2006-12-15 | |
| PCT/US2007/025602 WO2008076356A1 (en) | 2006-12-15 | 2007-12-14 | Novel oxadiazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010513283A JP2010513283A (ja) | 2010-04-30 |
| JP2010513283A5 true JP2010513283A5 (enExample) | 2010-06-17 |
Family
ID=39536624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009541394A Withdrawn JP2010513283A (ja) | 2006-12-15 | 2007-12-14 | 新規なオキサジアゾール化合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7834039B2 (enExample) |
| EP (1) | EP2109364A4 (enExample) |
| JP (1) | JP2010513283A (enExample) |
| KR (1) | KR20090095648A (enExample) |
| CN (1) | CN101562977A (enExample) |
| AU (1) | AU2007334436A1 (enExample) |
| BR (1) | BRPI0720043A2 (enExample) |
| CA (1) | CA2672616A1 (enExample) |
| MX (1) | MX2009006304A (enExample) |
| NZ (1) | NZ577111A (enExample) |
| RU (1) | RU2009127095A (enExample) |
| SG (1) | SG177221A1 (enExample) |
| TW (1) | TW200840567A (enExample) |
| WO (1) | WO2008076356A1 (enExample) |
| ZA (1) | ZA200903693B (enExample) |
Families Citing this family (125)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006010379A1 (en) | 2004-07-29 | 2006-02-02 | Actelion Pharmaceuticals Ltd. | Novel thiophene derivatives as immunosuppressive agents |
| RS55634B1 (sr) | 2005-12-13 | 2017-06-30 | Incyte Holdings Corp | Heteroaril substituisani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze |
| TWI404706B (zh) | 2006-01-11 | 2013-08-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| AU2007209051A1 (en) | 2006-01-24 | 2007-08-02 | Actelion Pharmaceuticals Ltd | Novel pyridine derivatives |
| AR061841A1 (es) | 2006-09-07 | 2008-09-24 | Actelion Pharmaceuticals Ltd | Derivados de tiofen-oxadiazoles, agonistas del receptor s1p1/edg1, composiciones farmaceuticas que los contienen y usos como agentes inmunomoduladores. |
| JP5253401B2 (ja) | 2006-09-07 | 2013-07-31 | アクテリオン ファーマシューティカルズ リミテッド | 免疫調節薬としてのピリジン−４−イル誘導体 |
| US8288554B2 (en) | 2006-09-08 | 2012-10-16 | Actelion Pharmaceuticals Ltd. | Pyridin-3-yl derivatives as immunomodulating agents |
| WO2008035239A1 (en) | 2006-09-21 | 2008-03-27 | Actelion Pharmaceuticals Ltd | Phenyl derivatives and their use as immunomodulators |
| CN101541782A (zh) * | 2006-10-04 | 2009-09-23 | 先灵公司 | 作为凝血酶受体拮抗剂的二环和三环衍生物 |
| US20110207704A1 (en) * | 2006-12-15 | 2011-08-25 | Abbott Laboratories | Novel Oxadiazole Compounds |
| ES2450750T3 (es) * | 2007-03-16 | 2014-03-25 | Actelion Pharmaceuticals Ltd. | Derivados de amino-piridina como agonistas del receptor S1P1/EDG1 |
| HUE043732T2 (hu) | 2007-06-13 | 2019-09-30 | Incyte Holdings Corp | Januskináz gátló hatású (R)-3-(4-(7H pirrolo[2,3-d]pirimidin-4-il)-1H-pirazol-1-il)-3-ciklopentilpropánnitril sók alkalmazása |
| WO2009009041A2 (en) * | 2007-07-06 | 2009-01-15 | Kinex Pharmaceuticals, Llc | Compositions and methods for modulating a kinase cascade |
| US20090069288A1 (en) * | 2007-07-16 | 2009-03-12 | Breinlinger Eric C | Novel therapeutic compounds |
| CA2699980C (en) | 2007-08-13 | 2015-06-02 | Divergence, Inc. | Methods for the control of plant parasitic nematodes comprising application of oxadiazole compounds to plants, seeds or soil |
| ATE502938T1 (de) | 2007-08-17 | 2011-04-15 | Actelion Pharmaceuticals Ltd | Pyridinderivate als s1p1/edg1-rezeptormodulatoren |
| US8202865B2 (en) | 2007-10-04 | 2012-06-19 | Merck Serono Sa | Oxadiazole derivatives |
| MX2010003614A (es) | 2007-10-04 | 2010-04-21 | Merck Serono Sa | Compuestos de diarilo oxadiazol. |
| AR069146A1 (es) | 2007-11-01 | 2009-12-30 | Actelion Pharmaceuticals Ltd | Derivados de pirimidina, composicion farmaceutica que los comprende y el uso de esta para el tratamiento de enfermedades relacionadas con la activacion del sistema inmunitario. |
| KR20100095593A (ko) | 2007-12-10 | 2010-08-31 | 액테리온 파마슈티칼 리미티드 | Ｓ１ｐ１/ｅｄｇ１의 작동약으로서 티오펜 유도체 |
| GB0725104D0 (en) * | 2007-12-21 | 2008-01-30 | Glaxo Group Ltd | Compounds |
| JP2011510073A (ja) * | 2008-01-25 | 2011-03-31 | 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アゴニストとして作用するジヒドロ−１Ｈ−ピロロ［１，２−ａ］インドール−１−イルカルボン酸誘導体 |
| JP5411877B2 (ja) * | 2008-03-06 | 2014-02-12 | アクテリオン ファーマシューティカルズ リミテッド | ピリジン化合物 |
| AU2009220893A1 (en) | 2008-03-07 | 2009-09-11 | Actelion Pharmaceuticals Ltd | Novel aminomethyl benzene derivatives |
| HRP20130641T1 (en) * | 2008-03-07 | 2013-08-31 | Actelion Pharmaceuticals Ltd. | Pyridin-2-yl derivatives as immunomodulating agents |
| US20090298894A1 (en) * | 2008-04-21 | 2009-12-03 | Asahi Kasei Pharma Corporation | Amino acid compounds |
| ES2549761T3 (es) | 2008-05-14 | 2015-11-02 | The Scripps Research Institute | Nuevos moduladores de los receptores de esfingosina fosfato |
| NZ589412A (en) * | 2008-05-20 | 2012-11-30 | Kyorin Seiyaku Kk | Use of a sphingosine-1-phosphate (S1P) agonist for maintance of induced remission of autoimmune or inflammatory diseases after inital treatment |
| US20100010053A1 (en) * | 2008-06-20 | 2010-01-14 | Jose Luis Castro Pineiro | Compounds |
| KR20180023049A (ko) | 2008-07-23 | 2018-03-06 | 아레나 파마슈티칼스, 인크. | 자가면역성 및 염증성의 장애의 치료에 유용한 치환된 1,2,3,4-테트라히드로시클로펜타[ｂ]인돌-3-일)아세트산 유도체 |
| CN105816453B (zh) | 2008-08-27 | 2021-03-05 | 艾尼纳制药公司 | 用于治疗自身免疫性病症和炎性病症的作为s1p1受体激动剂的经取代的三环酸衍生物 |
| CL2009001884A1 (es) * | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
| AR074061A1 (es) * | 2008-10-31 | 2010-12-22 | Lexicon Pharmaceuticals Inc | Inhibidores de s1p liasa para el tratamiento de la malaria cerebral y formulacion farmaceutica |
| ES2405054T3 (es) | 2009-01-23 | 2013-05-30 | Bristol-Myers Squibb Company | Derivados de pirazol-1,2,4-oxadiazol como agonistas de esfingosina-1-fosfato |
| US8404672B2 (en) | 2009-01-23 | 2013-03-26 | Bristol-Meyers Squibb Company | Substituted heterocyclic compounds |
| US8354398B2 (en) | 2009-01-23 | 2013-01-15 | Bristol-Myers Squibb Company | Substituted isoxazole compounds |
| KR101220182B1 (ko) * | 2009-02-25 | 2013-01-11 | 에스케이바이오팜 주식회사 | 치환된 아졸 유도체 화합물, 이를 포함하는 약제학적 조성물 및 이를 이용한 파킨슨씨 병 치료방법 |
| EP2432555B1 (en) | 2009-05-22 | 2014-04-30 | Incyte Corporation | N-(hetero)aryl-pyrrolidine derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines and pyrrol-3-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| KR20120030447A (ko) | 2009-05-22 | 2012-03-28 | 인사이트 코포레이션 | Ｊａｋ 저해물질로서 ３-［４-（７ｈ-피롤로［２,３-ｄ］피리미딘-４-일）-１ｈ-피라졸-１-일］옥탄- 또는 헵탄-니트릴 |
| GB2470833B (en) * | 2009-06-03 | 2011-06-01 | Amira Pharmaceuticals Inc | Polycyclic antagonists of lysophosphatidic acid receptors |
| AR076984A1 (es) | 2009-06-08 | 2011-07-20 | Merck Serono Sa | Derivados de pirazol oxadiazol |
| GB0910689D0 (en) * | 2009-06-19 | 2009-08-05 | Glaxo Wellcome Mfg Pte Ltd | Novel compounds |
| WO2011005290A1 (en) * | 2009-06-23 | 2011-01-13 | Arena Pharmaceuticals, Inc. | Disubstituted oxadiazole derivatives useful in the treatment of autoimmune and inflammatory disorders |
| GB0911130D0 (en) * | 2009-06-26 | 2009-08-12 | Glaxo Group Ltd | Novel compounds |
| DK2454255T3 (da) | 2009-07-16 | 2013-12-16 | Actelion Pharmaceuticals Ltd | Pyridin-4-ylderivater som s1p1/edg1-agonister |
| US8399451B2 (en) | 2009-08-07 | 2013-03-19 | Bristol-Myers Squibb Company | Heterocyclic compounds |
| UY32858A (es) * | 2009-08-31 | 2011-03-31 | Abbott Healthcare Products Bv | Derivados de (tio)morfolina como moduladores de sip |
| WO2011028685A1 (en) | 2009-09-01 | 2011-03-10 | Incyte Corporation | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| EP2498609B1 (en) | 2009-11-13 | 2018-04-18 | Celgene International II Sàrl | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
| RS61829B1 (sr) * | 2009-11-13 | 2021-06-30 | Receptos Llc | Selektivni modulatori receptora sfingozin 1 fosfata i metode hiralne sinteze |
| CA2780433C (en) | 2009-11-13 | 2018-01-02 | Receptos, Inc. | Sphingosine 1 phosphate receptor modulators and methods of chiral synthesis |
| TW201120016A (en) * | 2009-12-08 | 2011-06-16 | Abbott Lab | Novel oxadiazole compounds |
| USRE49251E1 (en) | 2010-01-04 | 2022-10-18 | Mapi Pharma Ltd. | Depot systems comprising glatiramer or pharmacologically acceptable salt thereof |
| US8853419B2 (en) | 2010-01-27 | 2014-10-07 | 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 |
| CN102884064B (zh) | 2010-03-03 | 2016-01-13 | 艾尼纳制药公司 | 制备s1p1受体调节剂及其晶体形式的方法 |
| TWI531572B (zh) | 2010-03-10 | 2016-05-01 | 英塞特公司 | 作為ｊａｋ１抑制劑之哌啶－４－基三亞甲亞胺衍生物 |
| WO2011133734A1 (en) | 2010-04-23 | 2011-10-27 | Bristol-Myers Squibb Company | 4 - (5 - isoxazolyl or 5 - pyrrazolyl -1,2,4- oxadiazol - 3 - yl) -mandelic acid amides as sphingosin- 1 - phosphate 1 rreceptor agonists |
| JP2013525383A (ja) * | 2010-04-30 | 2013-06-20 | グラクソ グループ リミテッド | Ｓ１ｐ１受容体のアゴニストとしての化合物 |
| KR101799429B1 (ko) * | 2010-05-03 | 2017-11-21 | 에스케이바이오팜 주식회사 | 신경 세포 사멸 또는 신경 퇴화를 억제하기 위한 약학적 조성물 |
| EP2390252A1 (en) * | 2010-05-19 | 2011-11-30 | Almirall, S.A. | New pyrazole derivatives |
| US20110288107A1 (en) | 2010-05-21 | 2011-11-24 | Bhavnish Parikh | Topical formulation for a jak inhibitor |
| JP5788507B2 (ja) * | 2010-07-20 | 2015-09-30 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 置換３−フェニル−１，２，４−オキサジアゾール化合物 |
| EP2619190B1 (en) | 2010-09-24 | 2015-08-12 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds and their use as s1p1 agonists |
| EP2640725B1 (en) | 2010-11-19 | 2015-01-07 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as jak inhibitors |
| PH12013501001A1 (en) | 2010-11-19 | 2019-09-02 | Incyte Holdings Corp | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| AU2011332196A1 (en) | 2010-11-24 | 2013-07-11 | Allergan, Inc. | Indole derivatives as modulators of S1P receptors |
| CN103338764A (zh) * | 2010-12-03 | 2013-10-02 | 阿勒根公司 | 作为鞘氨醇1-磷酸(s1p)受体调节剂的新型氮杂环丁烷衍生物 |
| EP2646018B1 (en) | 2010-12-03 | 2014-10-22 | Allergan, Inc. | Novel oxime azetidine derivatives as sphingosine 1-phosphate (s1p) receptor modulators |
| KR20130133234A (ko) * | 2010-12-03 | 2013-12-06 | 알러간, 인코포레이티드 | 스핑고신 1-포스페이트 (s1p) 수용체 조절제로서의 신규한 피리딘 유도체 |
| AU2011337004A1 (en) | 2010-12-03 | 2013-07-11 | Allergan, Inc. | Novel phenyl oxadiazole derivatives as sphingosine 1-phosphate (S1P) receptor modulators |
| BR112013013640A2 (pt) | 2010-12-03 | 2016-09-13 | Allergan Inc | derivados de oxima como moduladores de receptores de esfingosina-1-fosfato (s1p) |
| TWI546300B (zh) | 2011-01-19 | 2016-08-21 | 艾克泰聯製藥有限公司 | ２－甲氧基－吡啶－４－基衍生物 |
| WO2012112841A2 (en) * | 2011-02-18 | 2012-08-23 | Abbott Laboratories | [1,2,4]oxadiazol-3-yl acid salts and crystalline forms and their preparation |
| US20120232277A1 (en) * | 2011-03-08 | 2012-09-13 | Abbott Laboratories | Process for the preparation of 1,2,4-oxadiazol-3-yl derivatives of carboxylic acid |
| EP2511275A1 (en) * | 2011-04-12 | 2012-10-17 | Bioprojet | Novel piperidinyl monocarboxylic acids as S1P1 receptor agonists |
| EP2706999B1 (en) | 2011-05-13 | 2019-08-28 | Celgene International II Sàrl | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
| AU2012273164B2 (en) | 2011-06-20 | 2015-05-28 | Incyte Holdings Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as JAK inhibitors |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| JP6109195B2 (ja) * | 2012-01-13 | 2017-04-05 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | キナーゼ阻害剤として有用な複素環置換されたピリジル化合物 |
| TW201406761A (zh) | 2012-05-18 | 2014-02-16 | Incyte Corp | 做爲ｊａｋ抑制劑之哌啶基環丁基取代之吡咯并吡啶及吡咯并嘧啶衍生物 |
| US20150038511A1 (en) | 2012-08-09 | 2015-02-05 | Celgene Corporation | Treatment of immune-related and inflammatory diseases |
| NZ628077A (en) * | 2012-08-09 | 2017-04-28 | Celgene Corp | Treatment of immune-related and inflammatory diseases |
| ES2664332T3 (es) | 2012-08-30 | 2018-04-19 | Athenex, Inc. | N-(3-fluorobencil)-2-(5-(4-morfolinofenil)piridin-2-il) acetamida como moduladores de la proteína tirosina quinasa |
| CR20190073A (es) | 2012-11-15 | 2019-04-25 | Incyte Holdings Corp | FORMAS DE DOSIFICACIÓN DE RUXOLITINIB DE LIBERACIÓN SOTENIDA (Divisional 2015-265) |
| GB201223308D0 (en) | 2012-12-21 | 2013-02-06 | Univ Sunderland | Enzyme inhibitors |
| SMT202100694T1 (it) | 2013-03-06 | 2022-03-21 | Incyte Holdings Corp | Procedimenti e intermedi per produrre un inibitore di jak |
| TW201446768A (zh) * | 2013-03-15 | 2014-12-16 | Biogen Idec Inc | S1p及/或atx調節劑 |
| CA2920108C (en) | 2013-08-07 | 2022-07-05 | Incyte Corporation | Sustained release dosage forms for a jak1 inhibitor |
| EP2853532B1 (en) * | 2013-09-28 | 2020-12-09 | Instytut Farmakologii Polskiej Akademii Nauk | 1,2,4-oxadiazole derivatives as allosteric modulators of metabotropic glutamate receptors belonging to group III |
| TWI745271B (zh) | 2014-05-19 | 2021-11-11 | 美商西建公司 | 全身紅斑性狼瘡之治療 |
| WO2015184305A1 (en) | 2014-05-30 | 2015-12-03 | Incyte Corporation | TREATMENT OF CHRONIC NEUTROPHILIC LEUKEMIA (CNL) AND ATYPICAL CHRONIC MYELOID LEUKEMIA (aCML) BY INHIBITORS OF JAK1 |
| EP3160949A4 (en) * | 2014-06-26 | 2018-01-17 | Monash University | Enzyme interacting agents |
| DK3242666T5 (da) | 2015-01-06 | 2025-01-20 | Arena Pharm Inc | Forbindelsee til anvendelse i behandling af tilstande, der er forbundet med SIP1-receptoren |
| PH12017502097B1 (en) | 2015-05-20 | 2023-05-05 | 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 |
| JP6838744B2 (ja) | 2015-06-22 | 2021-03-03 | 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レセプター関連障害における使用のための（Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸（化合物１）の結晶性Ｌ−アルギニン塩 |
| CN114149424B (zh) | 2015-11-13 | 2025-05-13 | 奥比兰制药有限公司 | 用于治疗疾病的杂环化合物 |
| US10548858B2 (en) * | 2016-08-18 | 2020-02-04 | Memorial Sloan Kettering Cancer Center | Inhibition of sphingosine 1-phosphate receptor for treatment and prevention of lymphedema |
| US12097292B2 (en) | 2016-08-28 | 2024-09-24 | Mapi Pharma Ltd. | Process for preparing microparticles containing glatiramer acetate |
| US12370233B2 (en) | 2016-08-31 | 2025-07-29 | Mapi Pharma Ltd. | Depot systems comprising glatiramer acetate |
| US11168062B2 (en) | 2016-09-12 | 2021-11-09 | University Of Notre Dame Du Lac | Compounds for the treatment of Clostridium difficile infection |
| CN110099898B (zh) | 2016-10-24 | 2023-07-25 | 优曼尼蒂治疗公司 | 化合物及其用途 |
| WO2018129403A1 (en) | 2017-01-06 | 2018-07-12 | Yumanity Therapeutics | Methods for the treatment of neurological disorders |
| 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 |
| KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
| AU2018242998B2 (en) | 2017-03-26 | 2023-11-02 | Mapi Pharma Ltd. | Glatiramer depot systems for treating progressive forms of multiple sclerosis |
| WO2019018718A1 (en) * | 2017-07-21 | 2019-01-24 | Icahn School Of Medicine At Mount Sinai | BENZOTHIAZOLE AND PYRIDOTHIAZOLE COMPOUNDS AS ACTIVATORS OF THE SUMO PROTEIN |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| TW201924683A (zh) | 2017-12-08 | 2019-07-01 | 美商英塞特公司 | 用於治療骨髓增生性贅瘤的低劑量組合療法 |
| EP3746429B1 (en) | 2018-01-30 | 2022-03-09 | Incyte Corporation | Processes for preparing (1-(3-fluoro-2-(trifluoromethyl)isonicotinyl)piperidine-4-one) |
| CA3094527A1 (en) | 2018-03-23 | 2019-09-26 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| MX2020010322A (es) | 2018-03-30 | 2022-11-30 | Incyte Corp | Tratamiento de la hidradenitis supurativa mediante el uso de inhibidores de actividad de la cinasa janus (jak). |
| ES2987794T3 (es) | 2018-06-06 | 2024-11-18 | Arena Pharm Inc | Procedimientos de tratamiento de afecciones relacionadas con el receptor S1P1 |
| CN110627778B (zh) * | 2018-06-25 | 2023-01-24 | 中国科学院上海药物研究所 | 一类含有1,2,4-噁二唑环的化合物、其制备方法及其在免疫抑制药物中的应用 |
| KR102836433B1 (ko) | 2018-09-06 | 2025-07-21 | 아레나 파마슈티칼스, 인크. | 자가면역 및 염증성 장애의 치료에 유용한 화합물 |
| KR20220007845A (ko) | 2019-01-24 | 2022-01-19 | 유마니티 테라퓨틱스, 인크. | 화합물 및 이의 용도 |
| US11795147B2 (en) | 2019-08-26 | 2023-10-24 | Boehringer Ingelheim International Gmbh | Modulators of complex I |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
| BR112022017530A2 (pt) * | 2020-03-17 | 2022-10-18 | Sumitomo Pharma Co Ltd | Derivado de oxadiazol |
| WO2021195413A1 (en) * | 2020-03-27 | 2021-09-30 | Receptos Llc | Sphingosine 1 phosphate receptor modulators |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| CN116836157A (zh) * | 2022-03-25 | 2023-10-03 | 星希尔生物科技(上海)有限公司 | 一种噁二唑衍生物及其制备方法和用途 |
| WO2024049829A2 (en) * | 2022-08-29 | 2024-03-07 | Case Western Reserve University | Compositions and methods for treating and detecting cancer |
| WO2025096658A1 (en) * | 2023-10-30 | 2025-05-08 | Pretzel Therapeutics, Inc. | Compositions and inhibitors of polrmt |
| WO2025151705A1 (en) * | 2024-01-10 | 2025-07-17 | Vrise Therapeutics, Inc. | Novel inhibitors of dna damage repair pathway |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA962684A (en) | 1970-01-14 | 1975-02-11 | Takeda Chemical Industries Ltd. | Oxadiazole derivatives |
| US4003909A (en) | 1974-07-22 | 1977-01-18 | E. R. Squibb & Sons, Inc. | [(1,2,4-Oxadiazol-3-yl)phenyl]carbamic or thiocarbamic acid esters |
| JPH04295470A (ja) | 1991-03-22 | 1992-10-20 | Wakamoto Pharmaceut Co Ltd | モノアミンオキシダーゼ−ｂ酵素阻害活性を有する１，２，４−オキサジアゾール誘導体及びその製造法 |
| IL111613A0 (en) | 1993-11-12 | 1995-01-24 | Rhone Poulenc Rorer Ltd | Substituted phenyl compounds, their preparation and pharmaceutical compositions containing them |
| DE19643037A1 (de) * | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| WO2000025768A1 (en) | 1998-10-29 | 2000-05-11 | Trega Biosciences, Inc. | Oxadiazole, thiadiazole and triazole derivatives and combinatorial libraries thereof |
| AUPQ288499A0 (en) | 1999-09-16 | 1999-10-07 | Biota Scientific Management Pty Ltd | Antiviral agents |
| AU2001231202A1 (en) | 2000-01-28 | 2001-08-07 | Akkadix Corporation | Methods for killing nematodes and nematode eggs using 4-phenoxy-6-aminopyrimidine derivatives |
| US6559140B2 (en) | 2000-03-09 | 2003-05-06 | Abbott Laboratories | Cyclic and bicyclic diamino histamine-3 receptor antagonists |
| WO2001066534A2 (en) | 2000-03-09 | 2001-09-13 | Abbott Laboratories | Cyclic and bicyclic diamino histamine-3 receptor antagonists |
| US6579880B2 (en) | 2000-06-06 | 2003-06-17 | Ortho-Mcneil Pharmaceutical, Inc. | Isoxazoles and oxadiazoles as anti-inflammatory inhibitors of IL-8 |
| ES2292830T3 (es) | 2001-02-21 | 2008-03-16 | Astrazeneca Ab | Compuestos heteropoliciclicos y su uso como antagonistas del receptor metabotropico de glutamato. |
| YU85403A (sh) | 2001-05-11 | 2006-03-03 | Pharmacia Corporation | Aromatični sulfonski hidroksamati i njihova upotreba kao proteaznih inhibitora |
| US20040024024A1 (en) | 2001-05-11 | 2004-02-05 | Freskos John N. | Aromatic sulfone hydroxamates and their use as protease inhibitors |
| AU2002358724A1 (en) | 2001-12-21 | 2003-07-09 | Ciba Specialty Chemicals Holding Inc. | Use of metal complex compounds as oxidation catalysts |
| JP2005170790A (ja) | 2002-01-09 | 2005-06-30 | Ajinomoto Co Inc | Ｎ−アルキルスルフォニル置換アミド誘導体 |
| WO2003087044A2 (en) | 2002-04-09 | 2003-10-23 | 7Tm Pharma A/S | Novel carboxamide compounds for use in mch receptor related disorders |
| CA2482341A1 (en) | 2002-04-09 | 2003-10-23 | 7Tm Pharma A/S | Novel methoxybenzamide compounds for use in mch receptor related disorders |
| 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 |
| EP1529045A2 (en) | 2002-08-09 | 2005-05-11 | Astra Zeneca AB | New compounds |
| AU2003279915A1 (en) | 2002-10-15 | 2004-05-04 | Merck And Co., Inc. | Process for making azetidine-3-carboxylic acid |
| AU2003226929A1 (en) | 2002-11-25 | 2004-06-18 | 7Tm Pharma A/S | Novel benzamide compounds for use in mch receptor related disorders |
| DK1618098T3 (en) * | 2003-04-11 | 2015-01-12 | Ptc Therapeutics Inc | 1,2,4-OXADIAZOLBENZOESYREFORBINDELSER AND THEIR USE FOR nonsense CONTROL AND TREATMENT OF AN ILLNESS |
| US7220745B2 (en) | 2003-05-15 | 2007-05-22 | Rigel Pharmaceuticals | Heterocyclic compounds useful to treat HCV |
| 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 |
| US20050171171A1 (en) | 2003-11-13 | 2005-08-04 | Ambit Biosciences Corporation | Amide derivatives as FLT-3 modulators |
| JP4451849B2 (ja) * | 2003-11-28 | 2010-04-14 | 日本曹達株式会社 | アリール複素環誘導体および農園芸用殺菌剤および殺虫剤 |
| EP1689389A4 (en) | 2003-12-04 | 2009-06-17 | Nat Health Research Institutes | INDOLE COMPOUNDS |
| CN1894225A (zh) | 2003-12-17 | 2007-01-10 | 默克公司 | 作为鞘氨醇1－磷酸(内皮分化基因)受体激动剂的(3,4－二取代)丙酸酯 |
| DE102004003812A1 (de) | 2004-01-25 | 2005-08-11 | Aventis Pharma Deutschland Gmbh | Arylsubstituierte Heterozyklen, Verfahren ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US7514434B2 (en) | 2004-02-23 | 2009-04-07 | Rigel Pharmaceuticals, Inc. | Heterocyclic compounds having an oxadiazole moiety and hydro isomers thereof |
| KR20070036149A (ko) | 2004-07-16 | 2007-04-02 | 얀센 파마슈티카 엔.브이. | 이량체 피페리딘 유도체 |
| JP4738034B2 (ja) * | 2004-08-12 | 2011-08-03 | 富士フイルム株式会社 | 液晶性化合物、組成物および薄膜 |
| 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 |
| US7705157B2 (en) | 2004-12-16 | 2010-04-27 | Symyx Solutions, Inc. | Phenol-heterocyclic ligands, metal complexes, and their uses as catalysts |
| NZ563522A (en) | 2005-04-22 | 2010-01-29 | Daiichi Sankyo Co Ltd | Heterocyclic compound with immunosuppressive activity |
| CA2610310A1 (en) | 2005-06-08 | 2006-12-14 | Novartis Ag | Polycyclic oxadiazoles or isoxazoles and their use as s1p receptor ligands |
| JP5114395B2 (ja) | 2005-06-30 | 2013-01-09 | プロシディオン・リミテッド | Ｇｐｃｒアゴニスト |
| AR058439A1 (es) | 2005-07-26 | 2008-02-06 | Portela & Ca Sa | Derivados de nitrocatecol como inhibidores de comt. procesos de obtencion y composiciones farmaceuticas. |
| HUP0500920A2 (en) | 2005-10-05 | 2007-07-30 | Richter Gedeon Nyrt | Oxadiazole derivatives, process for their preparation and their use |
| WO2007043401A1 (ja) | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | 含窒素複素環化合物およびそれを含有する医薬組成物 |
| WO2007076055A2 (en) | 2005-12-22 | 2007-07-05 | Entremed, Inc. | Compositions and methods comprising proteinase activated receptor antagonists |
| TWI404706B (zh) | 2006-01-11 | 2013-08-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| GB0601744D0 (en) | 2006-01-27 | 2006-03-08 | Novartis Ag | Organic compounds |
| EP1991535A1 (en) | 2006-02-21 | 2008-11-19 | University Of Virginia Patent Foundation | Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as sip receptor agonists |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| EA200802058A1 (ru) | 2006-05-09 | 2009-06-30 | Пфайзер Продактс Инк. | Производные циклоалкиламинокислот и их фармацевтические композиции |
| AR062156A1 (es) | 2006-08-01 | 2008-10-22 | Praecis Pharm Inc | Compuestos agonistas y selectivos del receptor s1p-1 |
| JP2009269819A (ja) | 2006-08-25 | 2009-11-19 | Asahi Kasei Pharma Kk | アミン化合物 |
| JP5253401B2 (ja) * | 2006-09-07 | 2013-07-31 | アクテリオン ファーマシューティカルズ リミテッド | 免疫調節薬としてのピリジン−４−イル誘導体 |
| US8288554B2 (en) * | 2006-09-08 | 2012-10-16 | Actelion Pharmaceuticals Ltd. | Pyridin-3-yl derivatives as immunomodulating agents |
| WO2008035239A1 (en) | 2006-09-21 | 2008-03-27 | Actelion Pharmaceuticals Ltd | Phenyl derivatives and their use as immunomodulators |
| MX2009003129A (es) | 2006-09-29 | 2009-04-06 | Novartis Ag | Derivados de oxadiazol con propiedades anti-inflamatorias e inmunosupresoras. |
| US8486979B2 (en) | 2006-12-12 | 2013-07-16 | Abbvie Inc. | 1,2,4 oxadiazole compounds and methods of use thereof |
| US20080167286A1 (en) | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
| JP5517629B2 (ja) | 2007-01-31 | 2014-06-11 | ノヴィファーマ，エス．アー． | Ｃｏｍｔ阻害剤用の投薬計画 |
| ES2450750T3 (es) * | 2007-03-16 | 2014-03-25 | Actelion Pharmaceuticals Ltd. | Derivados de amino-piridina como agonistas del receptor S1P1/EDG1 |
| JP2010524965A (ja) | 2007-04-19 | 2010-07-22 | ザ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・ペンシルバニア | ジフェニル−ヘテロアリール誘導体並びにアミロイド斑への結合及び画像化のためのその使用 |
| JP5622568B2 (ja) | 2007-06-03 | 2014-11-12 | バンダービルト ユニバーシティ | ベンズアミドｍＧｌｕＲ５の正のアロステリック調節因子ならびにその作製および使用方法 |
-
2007
- 2007-12-14 SG SG2011094539A patent/SG177221A1/en unknown
- 2007-12-14 EP EP07867755A patent/EP2109364A4/en not_active Withdrawn
- 2007-12-14 AU AU2007334436A patent/AU2007334436A1/en not_active Abandoned
- 2007-12-14 KR KR1020097014830A patent/KR20090095648A/ko not_active Withdrawn
- 2007-12-14 NZ NZ577111A patent/NZ577111A/en not_active IP Right Cessation
- 2007-12-14 JP JP2009541394A patent/JP2010513283A/ja not_active Withdrawn
- 2007-12-14 CN CNA2007800463459A patent/CN101562977A/zh active Pending
- 2007-12-14 CA CA002672616A patent/CA2672616A1/en not_active Abandoned
- 2007-12-14 BR BRPI0720043-9A patent/BRPI0720043A2/pt not_active IP Right Cessation
- 2007-12-14 WO PCT/US2007/025602 patent/WO2008076356A1/en not_active Ceased
- 2007-12-14 MX MX2009006304A patent/MX2009006304A/es not_active Application Discontinuation
- 2007-12-14 US US12/002,196 patent/US7834039B2/en active Active
- 2007-12-14 RU RU2009127095/04A patent/RU2009127095A/ru not_active Application Discontinuation
- 2007-12-17 TW TW096148339A patent/TW200840567A/zh unknown
-
2009
- 2009-05-27 ZA ZA200903693A patent/ZA200903693B/xx unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010513283A5 (enExample) | ||
| US8778955B2 (en) | Indole derivatives or benzimidazole derivatives for modulating IkB kinase | |
| CN108383836B (zh) | 作为mek抑制剂的杂环基化合物 | |
| JP4783729B2 (ja) | ４−シアノピラゾール−３−カルボキシアミド誘導体、それらの製造法およびｃｂ１カンナビノイドアンタゴニストとしての用途 | |
| RU2288914C2 (ru) | Новые замещенные индолы | |
| JP4853965B2 (ja) | アダマンタン誘導体およびアザビシクロオクタン誘導体およびアザビシクロノナン誘導体、ならびにこれらの調製方法およびｄｐｐ−ｉｖ阻害剤としてのこれらの使用 | |
| CN102656141B (zh) | 模拟造血生长因子的小分子化合物及其用途 | |
| US10294207B2 (en) | Pyrazole derivatives as TNIK, IKKϵ and TBK1 inhibitor and pharmaceutical composition comprising same | |
| JP2018150360A (ja) | グリオキサミド置換ピロールアミド誘導体およびｂ型肝炎を処置するための医薬品としてのその使用 | |
| RS60312B1 (sr) | Jedinjenja indol karboksamida korisna kao inhibitori kinaze | |
| CN113939288A (zh) | Mas相关g蛋白受体x4的调节剂及相关产物和方法 | |
| WO2001002359A1 (en) | Heterocyclic compounds and medicinal use thereof | |
| WO2004063169A1 (en) | Hydroxamid acid derivatives as histone deacetylase (hdac) inhibitors | |
| WO2009019167A1 (en) | 6-amino-pyrimidine-4-carboxamide derivatives and related compounds which bind to the sphingosine 1-phosphate (s1p) receptor for the treatment of multiple sclerosis | |
| CN107207489A (zh) | 作为nadph氧化酶抑制剂的酰氨基噻二唑衍生物 | |
| JP2010510297A (ja) | 置換２，５−ジヒドロ−３ｈ−ピラゾロ［４，３−ｃ］ピリダジン−３−オン誘導体、該誘導体の調製およびカンナビノイドｃｂ１受容体リガンドとしての同誘導体の使用 | |
| US20060041124A1 (en) | Process for preparing pyrrolotriazine kinase inhibitors | |
| KR20180002796A (ko) | 시클로프로판 카르복실산 유도체 및 이의 의약 용도 | |
| JP2007522191A (ja) | オキサゾール誘導体、その調製及びその治療上の使用 | |
| US20080269303A1 (en) | Heterocyclic derivatives, preparation and therapeutic use thereof | |
| CN103201268A (zh) | 作为广谱流感抗病毒药物的新型哌嗪类似物 | |
| JP2008525388A (ja) | カンナビノイドｃｂ１受容体アンタゴニストとしてのｎ−［（４，５−ジフェニル−３−アルキル−２−チエニル）メチル］アミン（アミド、スルホンアミド、カルバミン酸及び尿素）誘導体 | |
| TW200533659A (en) | Acylaminothiazole derivatives, their preparation and their therapeutic application | |
| CN115551846B (zh) | 1,4,5,6-四氢嘧啶-2-胺衍生物 | |
| JP2010514824A (ja) | 置換ｎ−（４−シアノ−１ｈ−ピラゾール−３−イル）メチルアミン誘導体、これらの調製およびこれらの治療的使用 |