TW201908311A - 化合物 - Google Patents
化合物Info
- Publication number
- TW201908311A TW201908311A TW107119972A TW107119972A TW201908311A TW 201908311 A TW201908311 A TW 201908311A TW 107119972 A TW107119972 A TW 107119972A TW 107119972 A TW107119972 A TW 107119972A TW 201908311 A TW201908311 A TW 201908311A
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- naphthyridin
- carboxamide
- substituted
- trans
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 175
- 238000000034 method Methods 0.000 claims abstract description 82
- 239000003112 inhibitor Substances 0.000 claims abstract description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 claims abstract description 12
- 208000035475 disorder Diseases 0.000 claims abstract description 12
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 claims abstract description 11
- 101710082112 Hematopoietic prostaglandin D synthase Proteins 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 275
- -1 methyl-tetrazolyl Chemical group 0.000 claims description 179
- 235000019000 fluorine Nutrition 0.000 claims description 149
- 229910052731 fluorine Inorganic materials 0.000 claims description 131
- 239000011737 fluorine Substances 0.000 claims description 125
- 125000001424 substituent group Chemical group 0.000 claims description 109
- 239000001257 hydrogen Substances 0.000 claims description 108
- 229910052739 hydrogen Inorganic materials 0.000 claims description 108
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 94
- 239000000460 chlorine Substances 0.000 claims description 94
- 229910052801 chlorine Inorganic materials 0.000 claims description 93
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 87
- 208000029549 Muscle injury Diseases 0.000 claims description 84
- 125000001153 fluoro group Chemical group F* 0.000 claims description 83
- 150000003839 salts Chemical class 0.000 claims description 82
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
- 125000002393 azetidinyl group Chemical group 0.000 claims description 67
- 229910052760 oxygen Inorganic materials 0.000 claims description 66
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims description 63
- 229910052794 bromium Inorganic materials 0.000 claims description 62
- 239000001301 oxygen Substances 0.000 claims description 60
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 59
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 48
- 150000002431 hydrogen Chemical class 0.000 claims description 47
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 208000014674 injury Diseases 0.000 claims description 27
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 238000001356 surgical procedure Methods 0.000 claims description 24
- 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 description 22
- 208000027418 Wounds and injury Diseases 0.000 claims description 20
- 230000006378 damage Effects 0.000 claims description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 241000282414 Homo sapiens Species 0.000 claims description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- 201000006938 muscular dystrophy Diseases 0.000 claims description 17
- 230000008439 repair process Effects 0.000 claims description 17
- 125000002971 oxazolyl group Chemical group 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 210000003205 muscle Anatomy 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 206010050031 Muscle strain Diseases 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- 241000282412 Homo Species 0.000 claims description 8
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 208000034693 Laceration Diseases 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- LMUMMJCCZMWLEN-UHFFFAOYSA-N spiro[3.3]heptyl Chemical group [CH]1CCC11CCC1 LMUMMJCCZMWLEN-UHFFFAOYSA-N 0.000 claims description 7
- 230000035882 stress Effects 0.000 claims description 7
- 230000008736 traumatic injury Effects 0.000 claims description 7
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 6
- 210000001264 anterior cruciate ligament Anatomy 0.000 claims description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
- 210000002435 tendon Anatomy 0.000 claims description 6
- 230000000472 traumatic effect Effects 0.000 claims description 6
- 206010010356 Congenital anomaly Diseases 0.000 claims description 5
- 208000023178 Musculoskeletal disease Diseases 0.000 claims description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000008901 benefit Effects 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 206010010121 compartment syndrome Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 201000000585 muscular atrophy Diseases 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 208000034656 Contusions Diseases 0.000 claims description 4
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 4
- 208000024744 aspirin-induced respiratory disease Diseases 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 201000009580 eosinophilic pneumonia Diseases 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000029323 Congenital myotonia Diseases 0.000 claims description 3
- 208000002740 Muscle Rigidity Diseases 0.000 claims description 3
- 208000000112 Myalgia Diseases 0.000 claims description 3
- 206010061533 Myotonia Diseases 0.000 claims description 3
- 208000010316 Myotonia congenita Diseases 0.000 claims description 3
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 238000002266 amputation Methods 0.000 claims description 3
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 3
- 125000003943 azolyl group Chemical group 0.000 claims description 3
- 230000009519 contusion Effects 0.000 claims description 3
- 238000002316 cosmetic surgery Methods 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 230000003111 delayed effect Effects 0.000 claims description 3
- 201000001981 dermatomyositis Diseases 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000011540 hip replacement Methods 0.000 claims description 3
- 238000013150 knee replacement Methods 0.000 claims description 3
- 230000007774 longterm Effects 0.000 claims description 3
- 208000015001 muscle soreness Diseases 0.000 claims description 3
- ONLRKTIYOMZEJM-UHFFFAOYSA-N n-methylmethanamine oxide Chemical compound C[NH+](C)[O-] ONLRKTIYOMZEJM-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 208000005987 polymyositis Diseases 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 206010006448 Bronchiolitis Diseases 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 206010006482 Bronchospasm Diseases 0.000 claims description 2
- LEAZFFHOYYSOPL-WKILWMFISA-N C(C)OC1=CC=C2C=C(C=NC2=N1)C(=O)N[C@@H]1CC[C@H](CC1)C(C)(C)O Chemical compound C(C)OC1=CC=C2C=C(C=NC2=N1)C(=O)N[C@@H]1CC[C@H](CC1)C(C)(C)O LEAZFFHOYYSOPL-WKILWMFISA-N 0.000 claims description 2
- WLMQWGKJPSXGSJ-UHFFFAOYSA-N C1(CC1)C1=CC=C2C=C(C=NC2=N1)C(=O)NC1CC2(C1)CC(C2)C(C)(C)O Chemical compound C1(CC1)C1=CC=C2C=C(C=NC2=N1)C(=O)NC1CC2(C1)CC(C2)C(C)(C)O WLMQWGKJPSXGSJ-UHFFFAOYSA-N 0.000 claims description 2
- VEKOTFOGNGVLSE-QAQDUYKDSA-N C1(CC1)C1=CC=C2C=C(C=NC2=N1)C(=O)N[C@@H]1CC[C@H](CC1)C(C)(C)O Chemical compound C1(CC1)C1=CC=C2C=C(C=NC2=N1)C(=O)N[C@@H]1CC[C@H](CC1)C(C)(C)O VEKOTFOGNGVLSE-QAQDUYKDSA-N 0.000 claims description 2
- SERIMSSARRQQMN-IIAWOOMASA-N C1(CC1)C1=CC=C2C=C(C=NC2=N1)C(=O)N[C@@H]1C[C@H](C1)N[C@@H](C(F)(F)F)CO Chemical compound C1(CC1)C1=CC=C2C=C(C=NC2=N1)C(=O)N[C@@H]1C[C@H](C1)N[C@@H](C(F)(F)F)CO SERIMSSARRQQMN-IIAWOOMASA-N 0.000 claims description 2
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- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 230000003389 potentiating effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 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 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 150000003163 prostaglandin D2 derivatives Chemical class 0.000 description 1
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229940043131 pyroglutamate Drugs 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940076788 pyruvate Drugs 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
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- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical class [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229950002757 teoclate Drugs 0.000 description 1
- XIRUXUKRGUFEKC-SSDOTTSWSA-N tert-butyl (2r)-2-(hydroxymethyl)azetidine-1-carboxylate Chemical class CC(C)(C)OC(=O)N1CC[C@@H]1CO XIRUXUKRGUFEKC-SSDOTTSWSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 1
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
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- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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- IKVDXUFZJARKPF-UHFFFAOYSA-M zinc;cyclopropane;bromide Chemical compound Br[Zn+].C1C[CH-]1 IKVDXUFZJARKPF-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| US201762522869P | 2017-06-21 | 2017-06-21 | |
| US62/522,869 | 2017-06-21 |
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| TW (1) | TW201908311A (https=) |
| UY (1) | UY37764A (https=) |
| WO (1) | WO2018229629A1 (https=) |
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| CA3085293A1 (en) * | 2017-12-13 | 2019-06-20 | Glaxosmithkline Intellectual Property Development Limited | Fused pyridines which act as inhibitors of h-pgds |
| JP2022506850A (ja) * | 2018-11-08 | 2022-01-17 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッド | 化学化合物 |
| CN109651241B (zh) * | 2018-12-27 | 2021-02-09 | 上海毕得医药科技股份有限公司 | 一种4-溴-6-氯烟醛的合成方法 |
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| CN112430632B (zh) * | 2020-11-18 | 2022-09-13 | 上海合全药物研发有限公司 | 2-((反式)-4-氨基环己烷基)异丙醇的制备方法 |
| MX2023005747A (es) | 2020-11-18 | 2023-07-28 | Deciphera Pharmaceuticals Llc | Inhibidores de gcn2 y perk quinasas y metodos de uso de los mismos. |
| CA3240926A1 (en) | 2021-12-17 | 2023-06-22 | Sato Pharmaceutical Co., Ltd. | Azaindole derivative inhibiting h-pgds |
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| US6576265B1 (en) | 1999-12-22 | 2003-06-10 | Acell, Inc. | Tissue regenerative composition, method of making, and method of use thereof |
| EP1389209B1 (en) | 2001-04-24 | 2009-04-08 | Purdue Research Foundation | Folate mimetics and folate-receptor binding conjugates thereof |
| US7868204B2 (en) | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US8163769B2 (en) | 2002-03-12 | 2012-04-24 | Abbott Laboratories | Antibacterial compounds |
| WO2004014377A1 (en) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | 4-hydroxyquinoline derivatives as matrix metalloproteinase inhibitors |
| WO2004056744A1 (en) | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| WO2005035526A1 (en) | 2003-10-09 | 2005-04-21 | Argenta Discovery Ltd. | Bicyclic compounds and their therapeutic use |
| WO2005094805A1 (ja) | 2004-04-01 | 2005-10-13 | Institute Of Medicinal Molecular Design. Inc. | イミン誘導体及びアミド誘導体 |
| TW200720255A (en) | 2005-07-13 | 2007-06-01 | Taiho Pharmaceutical Co Ltd | Benzoimidazole compound capable of inhibiting prostaglandin d synthetase |
| JP2007051121A (ja) | 2005-07-22 | 2007-03-01 | Taiho Yakuhin Kogyo Kk | プロスタグランジンｄ合成酵素を阻害するピリミジン化合物 |
| PE20110118A1 (es) | 2005-10-04 | 2011-03-08 | Aventis Pharma Inc | Compuestos de pirimidina amida como inhibidores de pgds |
| EP2129660A2 (en) | 2006-12-19 | 2009-12-09 | Pfizer Products Inc. | Nicotinamide derivatives as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| DK2142516T3 (da) | 2007-03-30 | 2013-04-15 | Sanofi Sa | Pyrimidinhydrazidforbindelser i ders egenskab af pgds-inhibitorer |
| GB0706793D0 (en) | 2007-04-05 | 2007-05-16 | Evotec Ag | Compounds |
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| TW201010997A (en) * | 2008-06-18 | 2010-03-16 | Pfizer Ltd | Nicotinamide derivatives |
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| US8536185B2 (en) | 2008-09-22 | 2013-09-17 | Cayman Chemical Company, Incorporated | Multiheteroaryl compounds as inhibitors of H-PGDS and their use for treating prostaglandin D2 mediated diseases |
| RU2496778C2 (ru) | 2009-03-09 | 2013-10-27 | Тайхо Фармасьютикал Ко., Лтд. | Пиперазиновое соединение, ингибирующее простагландин-d-синтазу |
| JP2011042643A (ja) | 2009-07-24 | 2011-03-03 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
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| CA2974784A1 (en) | 2015-01-23 | 2016-07-28 | Gvk Biosciences Private Limited | Inhibitors of trka kinase |
| CN108430992A (zh) * | 2015-12-17 | 2018-08-21 | 阿斯特克斯医疗公司 | 作为h-pgds抑制剂的喹啉-3-甲酰胺 |
| US10898469B2 (en) * | 2016-02-26 | 2021-01-26 | Sumitomo Dainippon Pharma Co., Ltd. | Imidazolylamide derivative |
| JOP20190072A1 (ar) * | 2016-10-13 | 2019-04-07 | Glaxosmithkline Ip Dev Ltd | مشتقات 1، 3 سيكلوبوتان ثنائي الاستبدال أو آزيتيدين كمثبطات للإنزيم المخلق للبروستاجلاندين d المكون للدم |
| CA3085293A1 (en) * | 2017-12-13 | 2019-06-20 | Glaxosmithkline Intellectual Property Development Limited | Fused pyridines which act as inhibitors of h-pgds |
-
2018
- 2018-06-11 EP EP18742598.8A patent/EP3638672A1/en not_active Withdrawn
- 2018-06-11 CN CN201880039565.7A patent/CN110753692A/zh active Pending
- 2018-06-11 BR BR112019026452-3A patent/BR112019026452A2/pt not_active Application Discontinuation
- 2018-06-11 UY UY0001037764A patent/UY37764A/es unknown
- 2018-06-11 US US16/621,927 patent/US11149035B2/en not_active Expired - Fee Related
- 2018-06-11 CA CA3066979A patent/CA3066979A1/en not_active Abandoned
- 2018-06-11 JP JP2019568760A patent/JP2020523367A/ja not_active Ceased
- 2018-06-11 WO PCT/IB2018/054206 patent/WO2018229629A1/en not_active Ceased
- 2018-06-11 TW TW107119972A patent/TW201908311A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3638672A1 (en) | 2020-04-22 |
| US20200123152A1 (en) | 2020-04-23 |
| JP2020523367A (ja) | 2020-08-06 |
| US11149035B2 (en) | 2021-10-19 |
| CN110753692A (zh) | 2020-02-04 |
| UY37764A (es) | 2019-01-02 |
| CA3066979A1 (en) | 2018-12-20 |
| BR112019026452A2 (pt) | 2020-07-14 |
| WO2018229629A1 (en) | 2018-12-20 |
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