JP2010513283A5 - - Google Patents
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- 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.)
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- -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
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| 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 |
| TWI630207B (zh) | 2005-12-13 | 2018-07-21 | 英塞特控股公司 | 作為傑納斯激酶（ＪＡＮＵＳ ＫＩＮＡＳＥ）抑制劑之經雜芳基取代之吡咯并〔２，３-ｂ〕吡啶及吡咯并〔２，３-ｂ〕嘧啶 |
| TWI404706B (zh) | 2006-01-11 | 2013-08-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| CN101370805B (zh) | 2006-01-24 | 2011-04-27 | 埃科特莱茵药品有限公司 | 吡啶衍生物 |
| TWI408139B (zh) | 2006-09-07 | 2013-09-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| AU2007292993B2 (en) | 2006-09-07 | 2013-01-24 | Idorsia Pharmaceuticals Ltd | Pyridin-4-yl derivatives as immunomodulating agents |
| MX2009002234A (es) | 2006-09-08 | 2009-03-16 | Actelion Pharmaceuticals Ltd | Derivados de piridin-3-il como agentes inmunomoduladores. |
| MX2009002915A (es) | 2006-09-21 | 2009-03-31 | Actelion Pharmaceuticals Ltd | Derivados de fenilo y su uso como inmunomoduladores. |
| CA2667082A1 (en) * | 2006-10-04 | 2008-04-10 | Schering Corporation | Bicyclic and tricyclic derivatives as thrombin receptor antagonists |
| US20110207704A1 (en) * | 2006-12-15 | 2011-08-25 | Abbott Laboratories | Novel Oxadiazole Compounds |
| NZ580454A (en) | 2007-03-16 | 2011-05-27 | Actelion Pharmaceuticals Ltd | Amino- pyridine derivatives as s1p1 /edg1 receptor agonists |
| EP3070090B1 (en) | 2007-06-13 | 2018-12-12 | Incyte Holdings Corporation | Use of salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h- pyrazol-1-yl)-3- cyclopentylpropanenitrile |
| US8124605B2 (en) | 2007-07-06 | 2012-02-28 | Kinex Pharmaceuticals, Llc | Compositions and methods for modulating a kinase cascade |
| WO2009011850A2 (en) * | 2007-07-16 | 2009-01-22 | Abbott Laboratories | Novel therapeutic compounds |
| EP2786993B1 (en) | 2007-08-13 | 2017-11-15 | Monsanto Technology LLC | Compositions and methods for controlling nematodes |
| PT2195311E (pt) | 2007-08-17 | 2011-05-25 | Actelion Pharmaceuticals Ltd | Derivados de piridina como moduladores do receptor s1p1/edg1 |
| AU2008306886B2 (en) | 2007-10-04 | 2014-01-16 | Merck Serono S.A. | Oxadiazole diaryl compounds |
| US8202865B2 (en) * | 2007-10-04 | 2012-06-19 | Merck Serono Sa | Oxadiazole derivatives |
| CA2700917A1 (en) | 2007-11-01 | 2009-05-07 | Actelion Pharmaceuticals Ltd | Novel pyrimidine derivatives |
| 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 |
| AU2009206733A1 (en) * | 2008-01-25 | 2009-07-30 | Arena Pharmaceuticals, Inc. | Dihydro- 1H- pyrrolo [1,2-a] indol-1-yl carboxylic derivatives which act as S1P1 agonists |
| 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 |
| CN102015695B (zh) * | 2008-03-07 | 2014-08-27 | 埃科特莱茵药品有限公司 | 吡啶-2-基衍生物 |
| JP5481395B2 (ja) * | 2008-03-07 | 2014-04-23 | アクテリオン ファーマシューティカルズ リミテッド | 新規なアミノメチルベンゼン誘導体 |
| US20090298894A1 (en) * | 2008-04-21 | 2009-12-03 | Asahi Kasei Pharma Corporation | Amino acid compounds |
| AU2009258242B2 (en) | 2008-05-14 | 2015-07-16 | The Scripps Research Institute | Novel modulators of sphingosine phosphate receptors |
| 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 |
| KR20190004843A (ko) | 2008-07-23 | 2019-01-14 | 아레나 파마슈티칼스, 인크. | 자가면역성 및 염증성의 장애의 치료에 유용한 치환된 1,2,3,4-테트라히드로시클로펜타[ｂ]인돌-3-일)아세트산 유도체 |
| JP5726737B2 (ja) | 2008-08-27 | 2015-06-03 | 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 | 自己免疫障害および免疫性障害の治療において有用なｓ１ｐ１受容体のアゴニストとしての置換三環式酸誘導体 |
| 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 |
| WO2010085582A1 (en) * | 2009-01-23 | 2010-07-29 | Bristol-Myers Squibb Company | Substituted oxadiazole derivatives as s1p agonists in the treatment of autoimmune and inflammatory diseases |
| WO2010085584A1 (en) | 2009-01-23 | 2010-07-29 | Bristol-Myers Squibb Company | Pyrazole-i, 2, 4 -oxad iazole derivatives as s.phing0sine-1-ph0sphate agonists |
| JP2012515787A (ja) * | 2009-01-23 | 2012-07-12 | ブリストル−マイヤーズ スクイブ カンパニー | 自己免疫疾患および炎症性疾患の処置におけるｓ１ｐアゴニストとしての置換オキサジアゾール誘導体 |
| KR101220182B1 (ko) | 2009-02-25 | 2013-01-11 | 에스케이바이오팜 주식회사 | 치환된 아졸 유도체 화합물, 이를 포함하는 약제학적 조성물 및 이를 이용한 파킨슨씨 병 치료방법 |
| AR076794A1 (es) | 2009-05-22 | 2011-07-06 | Incyte Corp | Derivados de n-(hetero)aril-pirrolidina de pirazol-4-il-pirrolo [2,3-d]pirimidinas y pirrol-3-il-pirrolo [2,3-d ]pirimidinas como inhibidores de la quinasa janus y composiciones farmaceuticas que los contienen |
| EP3643312A1 (en) | 2009-05-22 | 2020-04-29 | Incyte Holdings Corporation | 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]octane- or heptane-nitrile as jak inhibitors |
| 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 |
| SI2454255T1 (sl) | 2009-07-16 | 2014-01-31 | Actelion Pharmaceuticals Ltd. | Derivati piridin-4-ila kot agonisti s1p1/edg1 |
| 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 |
| AR078012A1 (es) | 2009-09-01 | 2011-10-05 | Incyte Corp | Derivados heterociclicos de las pirazol-4-il- pirrolo (2,3-d) pirimidinas como inhibidores de la quinasa janus |
| AU2010319982B2 (en) | 2009-11-13 | 2016-02-04 | Receptos Llc | 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 |
| RS57070B1 (sr) | 2009-11-13 | 2018-06-29 | Celgene Int Ii Sarl | Modulatori sfingozin 1 fosfatnog receptora i postupci asimetričnih sinteza |
| 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 |
| CN108558740B (zh) | 2010-01-27 | 2021-10-19 | 艾尼纳制药公司 | S1p1受体调节剂及其盐的制备方法 |
| CA2789480A1 (en) | 2010-03-03 | 2011-09-09 | Arena Pharmaceuticals, Inc. | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
| EP3050882B1 (en) | 2010-03-10 | 2018-01-31 | Incyte Holdings Corporation | Piperidin-4-yl azetidine derivatives as jak1 inhibitors |
| EP2560969B1 (en) * | 2010-04-23 | 2015-08-12 | Bristol-Myers Squibb Company | 4-(5-isoxazolyl or 5-pyrrazolyl-1,2,4-oxadiazol-3-yl)-mandelic acid amides as sphingosin-1-phosphate 1 receptor 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 |
| SG10201503983QA (en) | 2010-05-21 | 2015-06-29 | Incyte Corp | Topical Formulation for a JAK Inhibitor |
| EP2595969B1 (en) * | 2010-07-20 | 2015-04-22 | Bristol-Myers Squibb Company | Substituted 3-phenyl-1,2,4-oxadiazole compounds |
| WO2012040532A1 (en) * | 2010-09-24 | 2012-03-29 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds and their use as s1p1 agonists |
| US9034884B2 (en) | 2010-11-19 | 2015-05-19 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as JAK inhibitors |
| CN103415515B (zh) | 2010-11-19 | 2015-08-26 | 因塞特公司 | 作为jak抑制剂的环丁基取代的吡咯并吡啶和吡咯并嘧啶衍生物 |
| AU2011332196A1 (en) | 2010-11-24 | 2013-07-11 | Allergan, Inc. | Indole derivatives as modulators of S1P receptors |
| WO2012074780A1 (en) * | 2010-12-03 | 2012-06-07 | Allergan, Inc. | Novel oxime azetidine derivatives as sphingosine 1-phosphate (s1p) receptor modulators |
| KR20130123419A (ko) | 2010-12-03 | 2013-11-12 | 알러간, 인코포레이티드 | 스핑고신-1-포스페이트 (s1p) 수용체 조절제로서의 옥사디아졸 유도체 |
| WO2012074719A1 (en) | 2010-12-03 | 2012-06-07 | Allergan, Inc. | Novel pyridine derivatives as sphingosine 1-phosphate (s1p) receptor modulators |
| BR112013013639A2 (pt) | 2010-12-03 | 2016-09-06 | Allergan Inc | derivados de azetidina como moduladores do receptor de esfingosina-1-fosfato (s1p) |
| BR112013013640A2 (pt) * | 2010-12-03 | 2016-09-13 | Allergan Inc | derivados de oxima como moduladores de receptores de esfingosina-1-fosfato (s1p) |
| KR101869120B1 (ko) | 2011-01-19 | 2018-06-19 | 이도르시아 파마슈티컬스 리미티드 | 2-메톡시-피리딘-4-일 유도체 |
| US20120214848A1 (en) * | 2011-02-18 | 2012-08-23 | Abbott Laboratories | [1,2,4]oxadiazol-3-yl acid salts and crystalline forms and their preparation |
| WO2012122338A1 (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 |
| US9481659B2 (en) | 2011-05-13 | 2016-11-01 | Celgene International Ii Sàrl | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
| PE20140832A1 (es) | 2011-06-20 | 2014-07-14 | Incyte Corp | Derivados de azetidinil fenil, piridil o pirazinil carboxamida como inhibidores de jak |
| 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 |
| WO2013106612A1 (en) * | 2012-01-13 | 2013-07-18 | Bristol-Myers Squibb Company | Heterocyclic-substituted pyridyl compounds useful as kinase inhibitors |
| 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 |
| PT2882441T (pt) | 2012-08-09 | 2020-06-29 | Celgene Corp | Tratamento de doenças associadas à imunidade e inflamatórias |
| LT2890680T (lt) | 2012-08-30 | 2018-05-10 | Athenex, Inc. | N-(3-fluorbenzil-2-(5-(4-morfolinofenil)piridin-2-il)acetamidas, kaip proteintirozinkinazės moduliatorius |
| PL2919766T3 (pl) | 2012-11-15 | 2021-10-04 | Incyte Holdings Corporation | Postacie dawkowania ruksolitynibu o przedłużonym uwalnianiu |
| GB201223308D0 (en) | 2012-12-21 | 2013-02-06 | Univ Sunderland | Enzyme inhibitors |
| CN105189509B (zh) | 2013-03-06 | 2017-12-19 | 因赛特公司 | 用于制备jak抑制剂的方法及中间体 |
| TW201446768A (zh) * | 2013-03-15 | 2014-12-16 | Biogen Idec Inc | S1p及/或atx調節劑 |
| SG10201912203XA (en) | 2013-08-07 | 2020-02-27 | Incyte Corp | 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 |
| ES2969532T3 (es) | 2014-05-19 | 2024-05-21 | Celgene Corp | 3-(4-((4-(Morfolinometil-bencil)oxi)-1-oxoisoindolin-2-il)piperidin-2,6-diona para el tratamiento de lupus eritematoso sistémico |
| 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 |
| AU2015281799B2 (en) * | 2014-06-26 | 2019-11-28 | Central Adelaide Local Health Network Incorporated | Enzyme interacting agents |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| ES2770348T3 (es) | 2015-05-20 | 2020-07-01 | Idorsia Pharmaceuticals Ltd | Forma cristalina del compuesto (s)-3-{4-[5-(2-ciclopentil-6-metoxi-piridin-4-il)-[1,2,4]oxadiazol-3-il]-2-etil-6-metil-fenoxi}-propano-1,2-diol |
| HUE060476T2 (hu) | 2015-06-22 | 2023-03-28 | Arena Pharm Inc | (R)-2-(7-(4-ciklopentil-3-(trifluormetil)benziloxi)-1,2,3,4- tetrahidrociklopenta[B]indol-3-il)ecetsav kristályos L-arginin-sója S1P1 receptorral kapcsolatos rendellenességek esetén való alkalmazásra |
| SI3373931T1 (sl) | 2015-11-13 | 2023-02-28 | Oppilan Pharma Ltd. | Heterociklične spojine za zdravljenje bolezni |
| CA3033863C (en) * | 2016-08-18 | 2021-09-14 | 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 |
| AU2017319728B2 (en) | 2016-08-31 | 2024-09-05 | 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 |
| MA46589A (fr) | 2016-10-24 | 2019-08-28 | Yumanity Therapeutics Inc | Composés et utilisations de ces derniers |
| EP3566055B1 (en) | 2017-01-06 | 2025-03-12 | Janssen Pharmaceutica NV | Scd inhibitor for the treatment of neurological disorders |
| CN110545848A (zh) | 2017-02-16 | 2019-12-06 | 艾尼纳制药公司 | 用于治疗具有肠外表现的炎症性肠病的化合物和方法 |
| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| MX2019010174A (es) | 2017-03-26 | 2019-10-15 | Mapi Pharma Ltd | Sistemas de deposito de glatiramer para el tratamiento de formas progresivas de esclerosis multiple. |
| EP3654975A4 (en) * | 2017-07-21 | 2021-06-23 | Icahn School of Medicine at Mount Sinai | BENZOTHIAZOLE AND PYRIDOTHIAZOLE COMPOUNDS AS SUMO ACTIVATORS |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| EP3746429B1 (en) | 2018-01-30 | 2022-03-09 | Incyte Corporation | Processes for preparing (1-(3-fluoro-2-(trifluoromethyl)isonicotinyl)piperidine-4-one) |
| ES3043183T3 (en) | 2018-03-23 | 2025-11-25 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
| PT3773593T (pt) | 2018-03-30 | 2024-06-25 | Incyte Corp | Tratamento da hidradenite supurativa com inibidores de jak |
| US12156866B2 (en) | 2018-06-06 | 2024-12-03 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| 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 |
| EP3847158A1 (en) | 2018-09-06 | 2021-07-14 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
| MX2021008903A (es) | 2019-01-24 | 2021-11-04 | Yumanity Therapeutics Inc | Compuestos y usos de los mismos. |
| 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 |
| KR20220154208A (ko) * | 2020-03-17 | 2022-11-21 | 스미토모 파마 가부시키가이샤 | 옥사디아졸 유도체 |
| KR20220158743A (ko) * | 2020-03-27 | 2022-12-01 | 리셉토스 엘엘씨 | 스핑고신 1 포스페이트 수용체 조절제 |
| 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 |
| WO2024029638A1 (ko) * | 2022-08-01 | 2024-02-08 | 한국과학기술연구원 | 신규한 헤테로사이클릴-페닐-메틸아민 유도체, 이의 제조방법 및 이의 다발성 경화증 예방, 개선, 또는 치료 용도 |
| 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 |
| AU1455500A (en) | 1998-10-29 | 2000-05-22 | 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 |
| US20010049373A1 (en) | 2000-01-28 | 2001-12-06 | Chalquest Richard R. | Materials and methods for killing nematodes and nematode eggs |
| WO2001066534A2 (en) | 2000-03-09 | 2001-09-13 | Abbott Laboratories | Cyclic and bicyclic diamino histamine-3 receptor antagonists |
| US6559140B2 (en) * | 2000-03-09 | 2003-05-06 | 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 |
| KR100838447B1 (ko) | 2001-02-21 | 2008-06-16 | 아스트라제네카 아베 | 헤테로폴리시클릭 화합물 및 대사향성 글루타메이트수용체 길항제로서의 그의 용도 |
| US20040024024A1 (en) * | 2001-05-11 | 2004-02-05 | Freskos John N. | Aromatic sulfone hydroxamates and their use as protease inhibitors |
| US6689794B2 (en) | 2001-05-11 | 2004-02-10 | Pharmacia Corporation | Aromatic sulfone hydroxamates and their use as protease inhibitors |
| JP2005513136A (ja) | 2001-12-21 | 2005-05-12 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 酸化触媒としての金属錯体化合物の使用 |
| 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 |
| US20060235035A1 (en) | 2002-04-09 | 2006-10-19 | 7Tm Pharma A/S | Novel methoxybenzamibe compounds for use in mch receptor related disorders |
| WO2003087044A2 (en) | 2002-04-09 | 2003-10-23 | 7Tm Pharma A/S | Novel carboxamide compounds for use in mch receptor related disorders |
| EP1549640A4 (en) | 2002-06-17 | 2008-08-06 | Merck & Co Inc | 1 - ((5-ARYL-1,2,4-OXADIAZOL-3-YL) BENZYL) AZETIDINE-3-CARBOXYLATE AND 1 - ((5-ARYL-1,2,4-OXADIAZOL-3-YL) BENZYL) PYRROLIDIN-3-CARBOXYLATE AS EDG RECEPTOR AGONISTS |
| KR20050033070A (ko) * | 2002-08-09 | 2005-04-08 | 아스트라제네카 에이비이 | 메타보트로픽 글루타메이트 수용체-5의 조절제로서[1,2,4]옥사디아졸 |
| AU2003279915A1 (en) | 2002-10-15 | 2004-05-04 | Merck And Co., Inc. | Process for making azetidine-3-carboxylic acid |
| WO2004048319A1 (en) | 2002-11-25 | 2004-06-10 | 7Tm Pharma A/S | Novel benzamide compounds for use in mch receptor related disorders |
| EP3345895B1 (en) * | 2003-04-11 | 2019-12-04 | PTC Therapeutics, Inc. | 1,2,4-oxadiazole benzoic acid compound and its use for nonsense suppression and the treatment of disease |
| US7220745B2 (en) * | 2003-05-15 | 2007-05-22 | Rigel Pharmaceuticals | Heterocyclic compounds useful to treat HCV |
| AU2004277947A1 (en) | 2003-10-01 | 2005-04-14 | Merck & Co., Inc. | 3,5-aryl, heteroaryl or cycloalkyl substituted-1,2,4-oxadiazoles as S1P receptor agonists |
| CA2545711A1 (en) | 2003-11-13 | 2005-06-02 | Ambit Biosciences Corporation | Urea derivatives as kinase modulators |
| WO2005051932A1 (ja) * | 2003-11-28 | 2005-06-09 | Nippon Soda Co., Ltd. | 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 |
| WO2005056522A2 (en) * | 2003-12-04 | 2005-06-23 | National 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 |
| EP1786775A1 (en) | 2004-07-16 | 2007-05-23 | Janssen Pharmaceutica N.V. | Dimeric piperidine derivates |
| 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 |
| WO2006047195A2 (en) | 2004-10-22 | 2006-05-04 | Merck & Co., Inc. | 2-(aryl)azacyclylmethyl carboxylates, sulfonates, phosphonates, phosphinates and heterocycles as s1p receptor agonists |
| WO2006066126A2 (en) | 2004-12-16 | 2006-06-22 | Symyx Technologies, Inc. | Phenol-heterocyclic ligands, metal complexes, and their uses as catalysts |
| EP1873153B1 (en) * | 2005-04-22 | 2010-07-07 | Daiichi Sankyo Company, Limited | 3-azetidinecarboxylic acid derivatives for use as immunosuppressants |
| EP1893591A1 (en) | 2005-06-08 | 2008-03-05 | Novartis AG | POLYCYCLIC OXADIAZOLES OR I SOXAZOLES AND THEIR USE AS SlP 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 |
| CA2616377C (en) | 2005-07-26 | 2014-04-01 | David Alexander Learmonth | Nitrocatechol derivatives as comt inhibitors |
| HUP0500920A2 (en) | 2005-10-05 | 2007-07-30 | Richter Gedeon Nyrt | Oxadiazole derivatives, process for their preparation and their use |
| US7947707B2 (en) | 2005-10-07 | 2011-05-24 | Kissei Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same |
| 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 |
| RU2008137553A (ru) | 2006-02-21 | 2010-03-27 | Юниверсити Оф Вирджиния Пэтент Фаундейшн (Us) | Фенил-циклоалкильные соединения, содержащие гетероциклические структуры |
| 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 |
| AU2007292993B2 (en) * | 2006-09-07 | 2013-01-24 | Idorsia Pharmaceuticals Ltd | Pyridin-4-yl derivatives as immunomodulating agents |
| MX2009002234A (es) * | 2006-09-08 | 2009-03-16 | Actelion Pharmaceuticals Ltd | Derivados de piridin-3-il como agentes inmunomoduladores. |
| MX2009002915A (es) | 2006-09-21 | 2009-03-31 | Actelion Pharmaceuticals Ltd | Derivados de fenilo y su uso como inmunomoduladores. |
| 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 |
| EP2481410B1 (en) | 2007-01-31 | 2016-07-13 | BIAL - Portela & Ca., S.A. | Nitrocatechol derivates as COMT inhibitors administered with a specific dosage regime |
| NZ580454A (en) * | 2007-03-16 | 2011-05-27 | Actelion Pharmaceuticals Ltd | Amino- pyridine derivatives as s1p1 /edg1 receptor agonists |
| EP2144507A4 (en) | 2007-04-19 | 2010-05-26 | Univ Pennsylvania | DIPHENYL HETEROARYL DERIVATIVES AND THEIR USE OF THE BINDING AND PICTURE OF AMYLOIDER PLAQUE |
| EP2162136A4 (en) | 2007-06-03 | 2012-02-15 | Univ Vanderbilt | GLUTAMATE METABOTROPIC POSITIVE RECEPTOR-BASED ALLOSTERIC-MODULATOR BENZAMIDE DERIVATIVES (MGLUR5) AND METHODS OF MAKING AND USING THEM |
-
2007
- 2007-12-14 CN CNA2007800463459A patent/CN101562977A/zh active Pending
- 2007-12-14 CA CA002672616A patent/CA2672616A1/en not_active Abandoned
- 2007-12-14 MX MX2009006304A patent/MX2009006304A/es not_active Application Discontinuation
- 2007-12-14 EP EP07867755A patent/EP2109364A4/en not_active Withdrawn
- 2007-12-14 JP JP2009541394A patent/JP2010513283A/ja not_active Withdrawn
- 2007-12-14 SG SG2011094539A patent/SG177221A1/en unknown
- 2007-12-14 NZ NZ577111A patent/NZ577111A/en not_active IP Right Cessation
- 2007-12-14 WO PCT/US2007/025602 patent/WO2008076356A1/en not_active Ceased
- 2007-12-14 KR KR1020097014830A patent/KR20090095648A/ko not_active Withdrawn
- 2007-12-14 US US12/002,196 patent/US7834039B2/en active Active
- 2007-12-14 AU AU2007334436A patent/AU2007334436A1/en not_active Abandoned
- 2007-12-14 RU RU2009127095/04A patent/RU2009127095A/ru not_active Application Discontinuation
- 2007-12-14 BR BRPI0720043-9A patent/BRPI0720043A2/pt not_active IP Right Cessation
- 2007-12-17 TW TW096148339A patent/TW200840567A/zh unknown
-
2009
- 2009-05-27 ZA ZA200903693A patent/ZA200903693B/xx unknown
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