TW201733988A - 化學化合物 - Google Patents
化學化合物 Download PDFInfo
- Publication number
- TW201733988A TW201733988A TW105141512A TW105141512A TW201733988A TW 201733988 A TW201733988 A TW 201733988A TW 105141512 A TW105141512 A TW 105141512A TW 105141512 A TW105141512 A TW 105141512A TW 201733988 A TW201733988 A TW 201733988A
- Authority
- TW
- Taiwan
- Prior art keywords
- quinoline
- carboxamide
- difluoromethoxy
- trans
- cyclohexyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 214
- 150000003839 salts Chemical class 0.000 claims abstract description 99
- 239000003112 inhibitor Substances 0.000 claims abstract description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 claims abstract description 9
- 101710082112 Hematopoietic prostaglandin D synthase Proteins 0.000 claims abstract description 8
- 208000035475 disorder Diseases 0.000 claims abstract description 7
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 392
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims description 342
- 125000000217 alkyl group Chemical group 0.000 claims description 268
- -1 -N 3 Chemical group 0.000 claims description 230
- 125000001424 substituent group Chemical group 0.000 claims description 171
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 133
- 229910052731 fluorine Inorganic materials 0.000 claims description 128
- 125000001153 fluoro group Chemical group F* 0.000 claims description 118
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 117
- 239000000460 chlorine Substances 0.000 claims description 110
- 229910052801 chlorine Inorganic materials 0.000 claims description 106
- 125000003545 alkoxy group Chemical group 0.000 claims description 93
- 235000019000 fluorine Nutrition 0.000 claims description 92
- 229910052757 nitrogen Chemical group 0.000 claims description 91
- 229910052794 bromium Inorganic materials 0.000 claims description 87
- 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 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 80
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 69
- 208000029549 Muscle injury Diseases 0.000 claims description 63
- 239000011737 fluorine Substances 0.000 claims description 62
- 125000005842 heteroatom Chemical group 0.000 claims description 59
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 57
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 53
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 52
- 125000002393 azetidinyl group Chemical group 0.000 claims description 52
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 51
- 125000003943 azolyl group Chemical group 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000004043 oxo group Chemical group O=* 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 229910052740 iodine Inorganic materials 0.000 claims description 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 19
- 125000002757 morpholinyl group Chemical group 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 208000014674 injury Diseases 0.000 claims description 18
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- 238000001356 surgical procedure Methods 0.000 claims description 17
- 210000003205 muscle Anatomy 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 15
- 125000002971 oxazolyl group Chemical group 0.000 claims description 15
- 230000006378 damage Effects 0.000 claims description 14
- 208000027418 Wounds and injury Diseases 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 230000008439 repair process Effects 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 12
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 8
- 206010003694 Atrophy Diseases 0.000 claims description 8
- 230000037444 atrophy Effects 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 208000034693 Laceration Diseases 0.000 claims description 6
- 206010050031 Muscle strain Diseases 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001540 azides Chemical group 0.000 claims description 6
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 201000000585 muscular atrophy Diseases 0.000 claims description 6
- MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 claims description 6
- 230000002441 reversible effect Effects 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 101100403745 Mus musculus Myot gene Proteins 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 210000002435 tendon Anatomy 0.000 claims description 5
- 241000156724 Antirhea Species 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 210000001264 anterior cruciate ligament Anatomy 0.000 claims description 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- YOXHCYXIAVIFCZ-UHFFFAOYSA-N cyclopropanol Chemical compound OC1CC1 YOXHCYXIAVIFCZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000001965 increasing effect Effects 0.000 claims description 4
- ONLRKTIYOMZEJM-UHFFFAOYSA-N n-methylmethanamine oxide Chemical compound C[NH+](C)[O-] ONLRKTIYOMZEJM-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 230000008736 traumatic injury Effects 0.000 claims description 4
- YBZADYHAFRRVLU-UHFFFAOYSA-N 7-bromo-6-chloro-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound CN1N=NN=C1N1CCC(CC1)NC(=O)C1=CC2=CC(Cl)=C(Br)C=C2N=C1 YBZADYHAFRRVLU-UHFFFAOYSA-N 0.000 claims description 3
- 206010010356 Congenital anomaly Diseases 0.000 claims description 3
- 208000029323 Congenital myotonia Diseases 0.000 claims description 3
- 208000010316 Myotonia congenita Diseases 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- 206010010121 compartment syndrome Diseases 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- CTJAKAQLCQKBTC-UHFFFAOYSA-N 1,1-difluoropropane Chemical compound CCC(F)F CTJAKAQLCQKBTC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
- HVGKACMORAHZRV-ZDUSSCGKSA-N 6-chloro-7-(3-fluoroazetidin-1-yl)-N-[(3S)-2-oxopyrrolidin-3-yl]quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1N1CC(C1)F)C(=O)N[C@@H]1C(NCC1)=O HVGKACMORAHZRV-ZDUSSCGKSA-N 0.000 claims description 2
- PYDPQIUCGHDTQT-UHFFFAOYSA-N 6-chloro-7-(difluoromethoxy)-N-(2,2-dimethyloxan-4-yl)quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1OC(F)F)C(=O)NC1CC(OCC1)(C)C PYDPQIUCGHDTQT-UHFFFAOYSA-N 0.000 claims description 2
- OTWKZHLNIMFJAF-GTNSWQLSSA-N 6-chloro-7-(difluoromethoxy)-N-[(1S,3S)-3-hydroxy-3-methylcyclopentyl]quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1OC(F)F)C(=O)N[C@@H]1C[C@@](CC1)(C)O OTWKZHLNIMFJAF-GTNSWQLSSA-N 0.000 claims description 2
- SCJWIFKAVFEZCE-LRUBCLLZSA-N 6-chloro-7-(difluoromethoxy)-N-[(3S)-5-methyl-2-oxopyrrolidin-3-yl]quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1OC(F)F)C(=O)N[C@@H]1C(NC(C1)C)=O SCJWIFKAVFEZCE-LRUBCLLZSA-N 0.000 claims description 2
- DYKOVMUOYKFJCL-UHFFFAOYSA-N 6-chloro-7-(difluoromethoxy)-N-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1OC(F)F)C(=O)NC1CCN(CC1)C(C(C)(C)O)=O DYKOVMUOYKFJCL-UHFFFAOYSA-N 0.000 claims description 2
- JPVQDLSWLTWFQI-RLFDGXBXSA-N 6-chloro-7-[(2S)-2-methylazetidin-1-yl]-N-[(3S,4R)-4-methyl-2-oxopyrrolidin-3-yl]quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1N1[C@H](CC1)C)C(=O)N[C@@H]1C(NC[C@H]1C)=O JPVQDLSWLTWFQI-RLFDGXBXSA-N 0.000 claims description 2
- GKGKUTNCNHTZCS-HNNXBMFYSA-N 6-chloro-7-cyclobutyl-N-[(3S)-2-oxopyrrolidin-3-yl]quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1C1CCC1)C(=O)N[C@@H]1C(NCC1)=O GKGKUTNCNHTZCS-HNNXBMFYSA-N 0.000 claims description 2
- MSSFDWCLXBRBQN-UHFFFAOYSA-N 6-chloro-7-cyclopropyl-N-(2-oxo-3,4-dihydro-1H-quinolin-4-yl)quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1C1CC1)C(=O)NC1CC(NC2=CC=CC=C12)=O MSSFDWCLXBRBQN-UHFFFAOYSA-N 0.000 claims description 2
- FPFXWMZNWLLAJK-AWEZNQCLSA-N 6-chloro-7-cyclopropyl-N-[(3S)-2-oxopyrrolidin-3-yl]quinoline-3-carboxamide Chemical compound ClC=1C=C2C=C(C=NC2=CC=1C1CC1)C(=O)N[C@@H]1C(NCC1)=O FPFXWMZNWLLAJK-AWEZNQCLSA-N 0.000 claims description 2
- PAXZAZXSEISIRR-UHFFFAOYSA-N 6-chloro-7-cyclopropyl-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound Cn1nnnc1N1CCC(CC1)NC(=O)c1cnc2cc(C3CC3)c(Cl)cc2c1 PAXZAZXSEISIRR-UHFFFAOYSA-N 0.000 claims description 2
- STUULBXRGOFWSC-UHFFFAOYSA-N 6-cyano-7-methoxy-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound C(#N)C=1C=C2C=C(C=NC2=CC=1OC)C(=O)NC1CCN(CC1)C1=NN=NN1C STUULBXRGOFWSC-UHFFFAOYSA-N 0.000 claims description 2
- SFRDGAIYBNHSAL-UHFFFAOYSA-N 6-fluoro-7-methoxy-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound FC=1C=C2C=C(C=NC2=CC=1OC)C(=O)NC1CCN(CC1)C1=NN=NN1C SFRDGAIYBNHSAL-UHFFFAOYSA-N 0.000 claims description 2
- OOKCRFCCUQBUIR-UHFFFAOYSA-N 7,8-dimethoxy-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound COc1ccc2cc(cnc2c1OC)C(=O)NC1CCN(CC1)c1nnnn1C OOKCRFCCUQBUIR-UHFFFAOYSA-N 0.000 claims description 2
- ARECEPLZIBBINR-UHFFFAOYSA-N 7-(azetidin-1-yl)-6-chloro-N-(3-hydroxy-3-methylcyclobutyl)quinoline-3-carboxamide Chemical compound N1(CCC1)C1=C(C=C2C=C(C=NC2=C1)C(=O)NC1CC(C1)(C)O)Cl ARECEPLZIBBINR-UHFFFAOYSA-N 0.000 claims description 2
- OLVZTWFALWUMSG-VXGBXAGGSA-N 7-(difluoromethoxy)-6-fluoro-N-[(1R,3R)-3-(2,2,2-trifluoroethylamino)cyclopentyl]quinoline-3-carboxamide Chemical compound FC(F)Oc1cc2ncc(cc2cc1F)C(=O)N[C@@H]1CC[C@H](C1)NCC(F)(F)F OLVZTWFALWUMSG-VXGBXAGGSA-N 0.000 claims description 2
- OARJHILKKGZXEB-WCQYABFASA-N 7-(difluoromethoxy)-6-fluoro-N-[(1S,2R)-2-hydroxycyclopentyl]quinoline-3-carboxamide Chemical compound FC(OC1=C(C=C2C=C(C=NC2=C1)C(=O)N[C@@H]1[C@@H](CCC1)O)F)F OARJHILKKGZXEB-WCQYABFASA-N 0.000 claims description 2
- JVFVQAZQNAUJNC-UHFFFAOYSA-N 7-(difluoromethoxy)-N-(1-methylsulfonylpiperidin-4-yl)quinoline-3-carboxamide Chemical compound FC(OC1=CC=C2C=C(C=NC2=C1)C(=O)NC1CCN(CC1)S(=O)(=O)C)F JVFVQAZQNAUJNC-UHFFFAOYSA-N 0.000 claims description 2
- CZSRSKZEGPUGBL-UHFFFAOYSA-N 7-(difluoromethoxy)-N-(5-methyl-1H-pyrazol-3-yl)quinoline-3-carboxamide Chemical compound FC(OC1=CC=C2C=C(C=NC2=C1)C(=O)NC1=CC(=NN1)C)F CZSRSKZEGPUGBL-UHFFFAOYSA-N 0.000 claims description 2
- MULBRCOFANWGJX-UHFFFAOYSA-N 7-(difluoromethoxy)-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound FC(OC1=CC=C2C=C(C=NC2=C1)C(=O)NC1CCN(CC1)C1=NN=NN1C)F MULBRCOFANWGJX-UHFFFAOYSA-N 0.000 claims description 2
- HNZVZKFRIOQEDU-UHFFFAOYSA-N 7-bromo-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound BrC1=CC=C2C=C(C=NC2=C1)C(=O)NC1CCN(CC1)C1=NN=NN1C HNZVZKFRIOQEDU-UHFFFAOYSA-N 0.000 claims description 2
- SETFCMSHLCTUAA-UHFFFAOYSA-N 7-chloro-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound Cn1nnnc1N1CCC(CC1)NC(=O)c1cnc2cc(Cl)ccc2c1 SETFCMSHLCTUAA-UHFFFAOYSA-N 0.000 claims description 2
- OVLUUOUARWWPBN-AWEZNQCLSA-N 7-cyclopropyl-6-fluoro-N-[(3S)-2-oxopyrrolidin-3-yl]quinoline-3-carboxamide Chemical compound C1(CC1)C1=C(C=C2C=C(C=NC2=C1)C(=O)N[C@@H]1C(NCC1)=O)F OVLUUOUARWWPBN-AWEZNQCLSA-N 0.000 claims description 2
- XZCLEEFABNAFCB-AWEZNQCLSA-N 7-cyclopropyl-N-[(3S)-2-oxopyrrolidin-3-yl]quinoline-3-carboxamide Chemical compound C1(CC1)C1=CC=C2C=C(C=NC2=C1)C(=O)N[C@@H]1C(NCC1)=O XZCLEEFABNAFCB-AWEZNQCLSA-N 0.000 claims description 2
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- JELKTAHYTLYONC-UHFFFAOYSA-N 7-ethyl-N-[1-(1-methyltetrazol-5-yl)piperidin-4-yl]quinoline-3-carboxamide Chemical compound CCc1ccc2cc(cnc2c1)C(=O)NC1CCN(CC1)c1nnnn1C JELKTAHYTLYONC-UHFFFAOYSA-N 0.000 claims description 2
- HKTKCEPXYGKWFJ-UHFFFAOYSA-N 8-ethyl-N-(1,3-thiazol-2-yl)quinoline-3-carboxamide Chemical compound C(C)C=1C=CC=C2C=C(C=NC=12)C(=O)NC=1SC=CN=1 HKTKCEPXYGKWFJ-UHFFFAOYSA-N 0.000 claims description 2
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- XPLWTSHSFUAVOP-QAQDUYKDSA-N C(CC#C)NC(CO[C@@H]1CC[C@H](CC1)NC(=O)C=1C=NC2=CC(=C(C=C2C=1)F)OC(F)F)=O Chemical compound C(CC#C)NC(CO[C@@H]1CC[C@H](CC1)NC(=O)C=1C=NC2=CC(=C(C=C2C=1)F)OC(F)F)=O XPLWTSHSFUAVOP-QAQDUYKDSA-N 0.000 claims description 2
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- CXRUWZNVAPQJRD-WGSAOQKQSA-N C1(CC1)C1=CC=C2C=C(C=NC2=C1)C(=O)N[C@@H]1CC[C@H](CC1)C(C)(C)O Chemical compound C1(CC1)C1=CC=C2C=C(C=NC2=C1)C(=O)N[C@@H]1CC[C@H](CC1)C(C)(C)O CXRUWZNVAPQJRD-WGSAOQKQSA-N 0.000 claims description 2
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Otolaryngology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| 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 |
| CN109843886B (zh) | 2016-10-17 | 2022-04-19 | 豪夫迈·罗氏有限公司 | 二环吡啶酮内酰胺及其使用方法 |
| EP3538512B1 (en) | 2016-11-11 | 2021-06-16 | Bayer Animal Health GmbH | New anthelmintic quinoline-3-carboxamide derivatives |
| US11072607B2 (en) | 2016-12-16 | 2021-07-27 | Genentech, Inc. | Inhibitors of RIP1 kinase and methods of use thereof |
| MX393318B (es) | 2017-04-18 | 2025-03-24 | Tempest Therapeutics Inc | Compuestos bicíclicos y su uso en el tratamiento del cáncer |
| UY37764A (es) * | 2017-06-13 | 2019-01-02 | Glaxosmithkline Ip Dev Ltd | Nuevos compuestos inhibidores de la prostaglandina d sintasa hematopoyética (h-pgds) |
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| CN111448192B (zh) | 2017-12-15 | 2024-04-12 | 拜耳动物保健有限责任公司 | 用于制备驱蠕虫的4-氨基-喹啉-3-甲酰胺衍生物的方法 |
| CN112313208B (zh) * | 2018-04-17 | 2024-04-19 | 泰普斯特医疗公司 | 双环羧酰胺及其使用方法 |
| EP3781571B1 (en) | 2018-04-20 | 2024-01-17 | F. Hoffmann-La Roche AG | N-[4-oxo-2,3-dihydro-pyrido[3,2-b][1,4]oxazepin-3-yl]-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazole-2-carboxamide derivatives and related compounds as rip1 kinase inhibitors for treating e.g. irritable bowel syndrome (ibs) |
| AU2019266511B2 (en) | 2018-05-09 | 2022-12-08 | Elanco Animal Health Gmbh | New quinoline derivatives |
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| AU2021253168A1 (en) | 2020-04-09 | 2022-11-03 | Elanco Animal Health Gmbh | Substituted condensed azines as anthelmintic compounds |
| CN111549000B (zh) * | 2020-06-18 | 2022-07-29 | 中国医学科学院整形外科医院 | 一种过表达Hpgds的重组脂肪干细胞、制备方法及其应用 |
| KR20230027059A (ko) | 2020-06-19 | 2023-02-27 | 사토 세이야쿠 가부시키가이샤 | H-pgds를 저해하는 축환 화합물 |
| EP4211131A4 (en) * | 2020-09-11 | 2025-01-15 | The Regents of the University of California | COMPOSITIONS AND METHODS FOR THE TREATMENT OF MUSCULAR DYSTROPHIAS |
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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 |
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| 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 |
| JP2010513458A (ja) * | 2006-12-19 | 2010-04-30 | ファイザー・プロダクツ・インク | H−pgdsの阻害剤としてのニコチンアミド誘導体、およびプロスタグランジンd2の仲介による疾患を治療するためのその使用 |
| PE20090552A1 (es) | 2007-03-30 | 2009-06-01 | Sanofi Aventis | Compuestos de pirimidina hidrazida como inhibidores de pgds |
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| WO2009153720A1 (en) | 2008-06-18 | 2009-12-23 | Pfizer Limited | Nicotinamide derivatives |
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| AP3272A (en) | 2008-09-22 | 2015-05-31 | Cayman Chem Co | Multiheteroaryl compounds as inhibitors of H-PGDS and their use for treating prosaglandin D2 mediated diseases |
| HUE027702T2 (en) | 2009-03-09 | 2016-11-28 | Taiho Pharmaceutical Co Ltd | Piperazine compound capable of inhibiting prostaglandin D synthase |
| US20120196854A1 (en) | 2009-10-06 | 2012-08-02 | Kyowa Hakko Kirin Co., Ltd. | Pharmaceutical composition comprising aromatic heterocyclic compound |
| AR078552A1 (es) | 2009-10-08 | 2011-11-16 | Sanofi Aventis | Derivados de feniloxadiazol como agentes inhibidores de las pgds |
| KR101723707B1 (ko) | 2010-01-22 | 2017-04-05 | 다이호야쿠힌고교 가부시키가이샤 | Pgds 저해 작용을 갖는 피페라진 화합물 |
| EP2872493B1 (en) * | 2012-07-13 | 2018-11-14 | Indiana University Research and Technology Corporation | 5,6,7-trimethoxy 4-phenyl quinolin-2-one derivatives for treatment of spinal muscular atrophy |
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| CA3008358A1 (en) | 2017-06-22 |
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| JP2019502691A (ja) | 2019-01-31 |
| US20210238162A1 (en) | 2021-08-05 |
| AU2016370779B2 (en) | 2019-07-25 |
| WO2017103851A1 (en) | 2017-06-22 |
| AR107044A1 (es) | 2018-03-14 |
| EP3390384B1 (en) | 2021-09-15 |
| UY37028A (es) | 2017-07-31 |
| BR112018012469A2 (pt) | 2018-12-18 |
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