SI9600287A - Substituted quinoline-2-carboxylic acid amides, the preparation thereof and the use thereof as medicines, as well as intermediates - Google Patents
Substituted quinoline-2-carboxylic acid amides, the preparation thereof and the use thereof as medicines, as well as intermediates Download PDFInfo
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- SI9600287A SI9600287A SI9600287A SI9600287A SI9600287A SI 9600287 A SI9600287 A SI 9600287A SI 9600287 A SI9600287 A SI 9600287A SI 9600287 A SI9600287 A SI 9600287A SI 9600287 A SI9600287 A SI 9600287A
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- Slovenia
- Prior art keywords
- alkyl
- alkoxy
- cycloalkyl
- aryloxy
- carbamoyl
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- 238000002360 preparation method Methods 0.000 title claims description 17
- 239000003814 drug Substances 0.000 title claims description 15
- 239000000543 intermediate Substances 0.000 title claims description 10
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical class C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 title description 4
- 229940079593 drug Drugs 0.000 title 1
- -1 benzyloxy, anilino, N-methylanilino Chemical group 0.000 claims abstract description 235
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 85
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 78
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 78
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 71
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 68
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 63
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 31
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 28
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
- 125000005277 alkyl imino group Chemical group 0.000 claims abstract description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract 10
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 3
- 150000007650 D alpha amino acids Chemical class 0.000 claims abstract 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 155
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 239000001257 hydrogen Substances 0.000 claims description 96
- 125000001424 substituent group Chemical group 0.000 claims description 84
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 83
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 81
- 239000000460 chlorine Substances 0.000 claims description 78
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 73
- 239000011737 fluorine Substances 0.000 claims description 67
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 150000002431 hydrogen Chemical class 0.000 claims description 46
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 18
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims description 17
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims description 17
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000003176 fibrotic effect Effects 0.000 claims description 7
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 230000036570 collagen biosynthesis Effects 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- 150000008575 L-amino acids Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 4
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005198 alkynylcarbonyloxy group Chemical group 0.000 claims description 2
- 238000007098 aminolysis reaction Methods 0.000 claims description 2
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 2
- 125000005239 aroylamino group Chemical group 0.000 claims description 2
- 125000004467 aryl imino group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 150000001371 alpha-amino acids Chemical class 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 208000036449 fibrotic liver disease Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- AYTYZMKHTZTURR-UHFFFAOYSA-N 3-hydroxyquinoline-2-carboxamide Chemical compound C1=CC=C2C=C(O)C(C(=O)N)=NC2=C1 AYTYZMKHTZTURR-UHFFFAOYSA-N 0.000 abstract 1
- 150000007649 L alpha amino acids Chemical group 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 143
- 239000000047 product Substances 0.000 description 90
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
- 239000004471 Glycine Substances 0.000 description 73
- 229960002449 glycine Drugs 0.000 description 73
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 67
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 31
- 239000003208 petroleum Substances 0.000 description 27
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 23
- 239000012043 crude product Substances 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 108010035532 Collagen Proteins 0.000 description 14
- 102000008186 Collagen Human genes 0.000 description 14
- 229920001436 collagen Polymers 0.000 description 14
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- 210000004185 liver Anatomy 0.000 description 13
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 12
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 11
- GBCAVSYHPPARHX-UHFFFAOYSA-M n'-cyclohexyl-n-[2-(4-methylmorpholin-4-ium-4-yl)ethyl]methanediimine;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1CCCCC1N=C=NCC[N+]1(C)CCOCC1 GBCAVSYHPPARHX-UHFFFAOYSA-M 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 241000894007 species Species 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- WJKJXKRHMUXQSL-UHFFFAOYSA-N benzyl glycinate 4-methylbenzenesulfonate salt Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.NCC(=O)OCC1=CC=CC=C1 WJKJXKRHMUXQSL-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000005245 sintering Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000000887 hydrating effect Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- JXYACYYPACQCDM-UHFFFAOYSA-N Benzyl glycinate Chemical compound NCC(=O)OCC1=CC=CC=C1 JXYACYYPACQCDM-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
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- 238000010992 reflux Methods 0.000 description 6
- JHFOWEGCZWLHNW-UHFFFAOYSA-N 4-fluoro-2-methyl-1-nitrobenzene Chemical compound CC1=CC(F)=CC=C1[N+]([O-])=O JHFOWEGCZWLHNW-UHFFFAOYSA-N 0.000 description 5
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000005911 haloform reaction Methods 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- ONDMKQWGMAVUNZ-UHFFFAOYSA-N butyl 2-aminoacetate Chemical compound CCCCOC(=O)CN ONDMKQWGMAVUNZ-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960002591 hydroxyproline Drugs 0.000 description 4
- HZOJBKMCYYWXAE-UHFFFAOYSA-N magnesium pentane-2,4-dione Chemical compound [Mg+2].CC(=O)CC([CH2-])=O.CC(=O)CC([CH2-])=O HZOJBKMCYYWXAE-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000012286 potassium permanganate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 3
- 150000005341 2-nitrobenzoic acids Chemical class 0.000 description 3
- ODWVFIWBWJXDMT-UHFFFAOYSA-N 3-(hydroxymethyl)-4-nitrophenol Chemical compound OCC1=CC(O)=CC=C1[N+]([O-])=O ODWVFIWBWJXDMT-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
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- 239000002585 base Substances 0.000 description 3
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- 238000002203 pretreatment Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- AOTWCYSQDSKAQT-UHFFFAOYSA-N 1,2-dichloro-4-methyl-5-nitrobenzene Chemical compound CC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O AOTWCYSQDSKAQT-UHFFFAOYSA-N 0.000 description 2
- WYUIWKFIFOJVKW-UHFFFAOYSA-N 1,2-dichloro-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(Cl)=C1 WYUIWKFIFOJVKW-UHFFFAOYSA-N 0.000 description 2
- JMGKOWLVRNNJCO-UHFFFAOYSA-N 1-(3-hydroxyquinolin-2-yl)ethanone Chemical compound C1=CC=C2C=C(O)C(C(=O)C)=NC2=C1 JMGKOWLVRNNJCO-UHFFFAOYSA-N 0.000 description 2
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- XGQJSMLGIQREBL-UHFFFAOYSA-N benzyl 2-[(3-phenylmethoxy-6-propan-2-yloxyquinoline-2-carbonyl)amino]acetate Chemical compound C=1C=CC=CC=1COC1=CC2=CC(OC(C)C)=CC=C2N=C1C(=O)NCC(=O)OCC1=CC=CC=C1 XGQJSMLGIQREBL-UHFFFAOYSA-N 0.000 description 1
- DZZPNUGSSGDLRA-UHFFFAOYSA-N benzyl 2-[(3-phenylmethoxyquinoline-2-carbonyl)amino]acetate Chemical compound C=1C=CC=CC=1COC(=O)CNC(=O)C1=NC2=CC=CC=C2C=C1OCC1=CC=CC=C1 DZZPNUGSSGDLRA-UHFFFAOYSA-N 0.000 description 1
- YOCVRTLDPXWCBV-UHFFFAOYSA-N benzyl 2-[[3-phenylmethoxy-6-(2,2,3,3-tetrafluoropropoxy)quinoline-2-carbonyl]amino]acetate Chemical compound C=1C=CC=CC=1COC1=CC2=CC(OCC(F)(F)C(F)F)=CC=C2N=C1C(=O)NCC(=O)OCC1=CC=CC=C1 YOCVRTLDPXWCBV-UHFFFAOYSA-N 0.000 description 1
- GNYXENYSXWGRCO-UHFFFAOYSA-N benzyl 2-[[4-(2,2,3,3,4,4,5,5-octafluoropentoxy)-3-phenylmethoxyquinoline-2-carbonyl]amino]acetate Chemical compound C=1C=CC=CC=1COC(=O)CNC(=O)C1=NC2=CC=CC=C2C(OCC(F)(F)C(F)(F)C(F)(F)C(F)F)=C1OCC1=CC=CC=C1 GNYXENYSXWGRCO-UHFFFAOYSA-N 0.000 description 1
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- NFCPBBXWCPNVDP-UHFFFAOYSA-N butyl 2-aminoacetate;4-methylbenzenesulfonic acid Chemical compound CCCCOC(=O)CN.CC1=CC=C(S(O)(=O)=O)C=C1 NFCPBBXWCPNVDP-UHFFFAOYSA-N 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- YEMPERUHXORKOO-UHFFFAOYSA-N ethyl 3-hydroxyquinoline-2-carboxylate Chemical compound C1=CC=C2C=C(O)C(C(=O)OCC)=NC2=C1 YEMPERUHXORKOO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- PWOYTBYNBYNZCO-UHFFFAOYSA-N ethyl quinoline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(=O)OCC)=CC=C21 PWOYTBYNBYNZCO-UHFFFAOYSA-N 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 102000005396 glutamine synthetase Human genes 0.000 description 1
- 108020002326 glutamine synthetase Proteins 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 229960001269 glycine hydrochloride Drugs 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- 210000000208 hepatic perisinusoidal cell Anatomy 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- YWOITFUKFOYODT-UHFFFAOYSA-N methanol;sodium Chemical compound [Na].OC YWOITFUKFOYODT-UHFFFAOYSA-N 0.000 description 1
- ZDIVCPODDCJMDM-UHFFFAOYSA-N methyl 3-methoxyquinoline-2-carboxylate Chemical class C1=CC=C2C=C(OC)C(C(=O)OC)=NC2=C1 ZDIVCPODDCJMDM-UHFFFAOYSA-N 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 210000001626 skin fibroblast Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- WWXRNIUGUCMPRR-UHFFFAOYSA-M sodium;7-chloro-3-phenylmethoxy-6-(2,2,2-trifluoroethoxy)quinoline-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=NC2=CC(Cl)=C(OCC(F)(F)F)C=C2C=C1OCC1=CC=CC=C1 WWXRNIUGUCMPRR-UHFFFAOYSA-M 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000000352 storage cell Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 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
- 238000010998 test method Methods 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19536263A DE19536263A1 (de) | 1995-09-28 | 1995-09-28 | Substituierte Chinolin-2-carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| DE19605170 | 1996-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI9600287A true SI9600287A (en) | 1997-04-30 |
Family
ID=26019051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9600287A SI9600287A (en) | 1995-09-28 | 1996-09-27 | Substituted quinoline-2-carboxylic acid amides, the preparation thereof and the use thereof as medicines, as well as intermediates |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US5726305A (fr) |
| EP (1) | EP0765871B1 (fr) |
| JP (1) | JPH09124606A (fr) |
| KR (1) | KR970061869A (fr) |
| CN (2) | CN1120157C (fr) |
| AT (1) | ATE263155T1 (fr) |
| AU (1) | AU728208B2 (fr) |
| CA (1) | CA2186717A1 (fr) |
| CZ (1) | CZ283396A3 (fr) |
| DE (1) | DE59610950D1 (fr) |
| ES (1) | ES2215184T3 (fr) |
| HU (1) | HUP9602685A3 (fr) |
| IL (2) | IL135495A (fr) |
| MX (1) | MX9604378A (fr) |
| MY (1) | MY133647A (fr) |
| NO (1) | NO308600B1 (fr) |
| NZ (1) | NZ299455A (fr) |
| PL (1) | PL316321A1 (fr) |
| SG (1) | SG45503A1 (fr) |
| SI (1) | SI9600287A (fr) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19650215A1 (de) * | 1996-12-04 | 1998-06-10 | Hoechst Ag | 3-Hydroxypyridin-2-carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel |
| DE19746287A1 (de) * | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| US20020198145A1 (en) * | 1999-06-10 | 2002-12-26 | Cognetix, Inc. | MuO-conopeptides and their use as local anesthetics |
| CA2432642A1 (fr) * | 2000-12-21 | 2002-08-08 | Subhash P. Khanapure | Composes aryle substitues en tant que nouveaux inhibiteurs selectifs de la cyclo-oxygenase-2, compositions et methodes d'utilisation |
| US20040146964A1 (en) * | 2001-03-21 | 2004-07-29 | Maxwell Patrick Henry | Assays, methods and means |
| EP2295060B1 (fr) | 2001-12-06 | 2018-10-31 | Fibrogen, Inc. | Traitement de conditions ischémiques ou hypoxiques |
| CN100522946C (zh) | 2001-12-06 | 2009-08-05 | 法布罗根股份有限公司 | 低氧诱导因子(HIF)α的稳定化 |
| US7618940B2 (en) | 2002-12-06 | 2009-11-17 | Fibrogen, Inc. | Fat regulation |
| US8124582B2 (en) * | 2002-12-06 | 2012-02-28 | Fibrogen, Inc. | Treatment of diabetes |
| PT1644336E (pt) * | 2003-06-06 | 2011-04-21 | Fibrogen Inc | Compostos de heteroarilo que contêm azoto e sua utilização no aumento da eritropoetina endógena |
| US8614204B2 (en) * | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| WO2005034929A2 (fr) * | 2003-10-10 | 2005-04-21 | Fibrogen, Inc. | Remodelage et vascularisation de tissus |
| EP1893186A2 (fr) * | 2005-06-06 | 2008-03-05 | Fibrogen, Inc. | Methode amelioree de traitement de l'anemie |
| WO2006138511A2 (fr) | 2005-06-15 | 2006-12-28 | Fibrogen, Inc. | Composes et procedes pour le traitement du cancer |
| WO2007025798A2 (fr) | 2005-07-27 | 2007-03-08 | F. Hoffmann-La Roche Ag | Aryloxy quinolines et leur utilisation en tant que 5-ht6 |
| US7728130B2 (en) * | 2005-12-09 | 2010-06-01 | Amgen Inc. | Quinolone based compounds exhibiting prolyl hydroxylase inhibitory activity |
| JP5161793B2 (ja) * | 2006-01-27 | 2013-03-13 | フィブロジェン， インコーポレイテッド | 低酸素症誘導因子（ｈｉｆ）を安定化するシアノイソキノリン化合物 |
| WO2007101204A1 (fr) * | 2006-02-27 | 2007-09-07 | Alcon Research, Ltd. | Méthode de traitement du glaucome |
| US7745461B1 (en) | 2006-02-27 | 2010-06-29 | Alcon Research, Ltd. | Method of treating dry eye disorders |
| ES2533765T3 (es) * | 2006-03-30 | 2015-04-15 | Lg Electronics Inc. | Un método y un aparato para descodificar/codificar una señal de video |
| CN103497184A (zh) * | 2006-04-04 | 2014-01-08 | 菲布罗根有限公司 | 作为hif调节剂的吡咯并吡啶和噻唑并吡啶化合物 |
| EP4095127A1 (fr) | 2006-06-26 | 2022-11-30 | Akebia Therapeutics Inc. | Inhibiteurs de prolyl hydroxylase et procédés d'utilisation |
| EP2111399A2 (fr) * | 2006-12-18 | 2009-10-28 | Amgen Inc. | Composés de naphtalénone présentant une activité inhibititrice de prolyle hydroxylase, compositions et utilisations de ceux-ci |
| US8048892B2 (en) * | 2006-12-18 | 2011-11-01 | Amgen Inc. | Azaquinolone based compounds exhibiting prolyl hydroxylase inhibitory activity, compositions, and uses thereof |
| CA2683956C (fr) * | 2007-04-18 | 2012-12-18 | Amgen Inc. | Quinolones et azaquinolones inhibant la prolyl hydroxylase |
| US7569726B2 (en) * | 2007-04-18 | 2009-08-04 | Amgen Inc. | Indanone derivatives that inhibit prolyl hydroxylase |
| WO2008137084A2 (fr) * | 2007-05-04 | 2008-11-13 | Amgen Inc. | Diazaquinolones inhibant l'activité de la prolyl hydroxylase |
| ES2389063T3 (es) * | 2007-05-04 | 2012-10-22 | Amgen, Inc | Derivados de tienopiridina y tiazolopiridina que inhiben la actividad prolil hidroxilasa |
| WO2009002533A1 (fr) * | 2007-06-27 | 2008-12-31 | The Brigham And Women's Hospital, Inc. | Thérapies d'affection abdominale inflammatoire |
| AU2009314155B2 (en) | 2008-11-14 | 2015-10-08 | Fibrogen, Inc. | Thiochromene derivatives as HIF hydroxylase inhibitors |
| UA107360C2 (en) | 2009-08-05 | 2014-12-25 | Biogen Idec Inc | Bicyclic aryl sphingosine 1-phosphate analogs |
| ES2575154T3 (es) * | 2009-12-17 | 2016-06-24 | Merck Sharp & Dohme Corp. | Moduladores alostéricos positivos del receptor M1 de quinolina amida |
| DK2672823T3 (en) | 2011-02-07 | 2016-11-28 | Biogen Ma Inc | S1P-modulating agents |
| NO2686520T3 (fr) | 2011-06-06 | 2018-03-17 | ||
| CN104470899B (zh) | 2012-03-09 | 2017-12-26 | 菲布罗根有限公司 | 作为hif羟化酶抑制剂的4‑羟基‑异喹啉化合物 |
| MY171483A (en) | 2012-07-16 | 2019-10-15 | Fibrogen Inc | Process for making isoquinoline compounds |
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| ES2905898T3 (es) | 2012-07-16 | 2022-04-12 | Fibrogen Inc | Formas cristalinas de un inhibidor de prolil hidroxilasa |
| SG11201500339XA (en) * | 2012-07-27 | 2015-02-27 | Biogen Ma Inc | Atx modulating agents |
| RU2666144C2 (ru) | 2013-01-24 | 2018-09-06 | Фиброген, Инк. | Кристаллические формы { [1-циано-5-(4-хлорофенокси)-4-гидроксиизохинолин-3-карбонил]-амино} -уксусной кислоты |
| BR112015031027A2 (pt) | 2013-06-13 | 2017-08-29 | Akebia Therapeutics Inc | Uso de um composto, método in vitro, composição farmacêutica e forma de dosagem única |
| MX2021001169A (es) | 2013-11-15 | 2023-02-10 | Akebia Therapeutics Inc | Formas sólidas de ácido {[5-(3-clorofenil)-3-hidroxipiridin-2-carb onil]amino}acético, composiciones, y usos de las mismas. |
| BR112017015852A2 (pt) | 2015-01-23 | 2018-03-27 | Akebia Therapeutics Inc | forma de cristal, sal hemicálcico, sal hemicálcico di-hidratado, sal monossódico hidratado, sal bissódico monoidratado, sal monossódico anidro e método para preparar o composto 1 |
| IL292262B2 (en) | 2015-04-01 | 2024-02-01 | Akebia Therapeutics Inc | Formulation of an oral administration form of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid |
| MX2020011845A (es) | 2018-05-09 | 2021-01-15 | Akebia Therapeutics Inc | Proceso para preparar acido 2-[[5-(3-clorofenil)-3-hidroxipiridina -2-carbonil]amino]acetico. |
| CN113302175A (zh) | 2018-11-09 | 2021-08-24 | 维瓦斯治疗公司 | 双环化合物 |
| CN114072207B (zh) | 2019-04-16 | 2024-03-29 | 维瓦斯治疗公司 | 双环化合物 |
| US11524939B2 (en) | 2019-11-13 | 2022-12-13 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4015255A1 (de) * | 1990-05-12 | 1991-11-14 | Hoechst Ag | Oxalyl-aminosaeurederivate, verfahren zu ihrer herstellung und ihrer verwendung als arzneimittel zur inhibierung der prolyl-hydroxylase |
| US5192773A (en) * | 1990-07-02 | 1993-03-09 | Vertex Pharmaceuticals, Inc. | Immunosuppressive compounds |
| EP0541042A1 (fr) * | 1991-11-05 | 1993-05-12 | Hoechst Aktiengesellschaft | Dérivés d'acide pyridine 2,4- et 2,5-dicarboxyliques, leur procédé de préparation et leur utilisation comme médicaments |
| TW352384B (en) * | 1992-03-24 | 1999-02-11 | Hoechst Ag | Sulfonamido- or sulfonamidocarbonylpyridine-2-carboxamides, process for their preparation and their use as pharmaceuticals |
| DE4233124A1 (de) * | 1992-10-02 | 1994-04-07 | Hoechst Ag | Acylsulfonamido- und Sulfonamidopyridin-2-carbonsäureester sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DK122693D0 (da) * | 1993-10-29 | 1993-10-29 | Hempels Skibsfarve Fab J C | Marin struktur |
| EP0650960B1 (fr) * | 1993-11-02 | 1997-03-05 | Hoechst Aktiengesellschaft | Esters de carboxamide hétérocycliques substitués, leur préparation et leur utilisation comme médicaments |
| DE59401924D1 (de) * | 1993-11-02 | 1997-04-10 | Hoechst Ag | Substituierte heterocyclische Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| NZ270267A (en) * | 1993-12-30 | 1997-03-24 | Hoechst Ag | 3-hydroxypyridin-2yl (and -quinolin-2-yl) carboxamide derivatives and pharmaceutical compositions |
-
1996
- 1996-06-29 IL IL13549596A patent/IL135495A/en not_active IP Right Cessation
- 1996-07-03 US US08/675,155 patent/US5726305A/en not_active Expired - Lifetime
- 1996-07-03 US US08/675,208 patent/US5719164A/en not_active Expired - Lifetime
- 1996-09-20 EP EP96115110A patent/EP0765871B1/fr not_active Expired - Lifetime
- 1996-09-20 AT AT96115110T patent/ATE263155T1/de not_active IP Right Cessation
- 1996-09-20 ES ES96115110T patent/ES2215184T3/es not_active Expired - Lifetime
- 1996-09-20 DE DE59610950T patent/DE59610950D1/de not_active Expired - Lifetime
- 1996-09-25 KR KR1019960042606A patent/KR970061869A/ko not_active Application Discontinuation
- 1996-09-26 NZ NZ299455A patent/NZ299455A/en unknown
- 1996-09-26 CZ CZ962833A patent/CZ283396A3/cs unknown
- 1996-09-26 CN CN96122806A patent/CN1120157C/zh not_active Expired - Lifetime
- 1996-09-26 AU AU65838/96A patent/AU728208B2/en not_active Ceased
- 1996-09-26 IL IL11930296A patent/IL119302A0/xx unknown
- 1996-09-27 SG SG1996010735A patent/SG45503A1/en unknown
- 1996-09-27 SI SI9600287A patent/SI9600287A/sl unknown
- 1996-09-27 MY MYPI96004023A patent/MY133647A/en unknown
- 1996-09-27 CA CA002186717A patent/CA2186717A1/fr not_active Abandoned
- 1996-09-27 NO NO964093A patent/NO308600B1/no not_active IP Right Cessation
- 1996-09-27 MX MX9604378A patent/MX9604378A/es unknown
- 1996-09-27 HU HU9602685A patent/HUP9602685A3/hu unknown
- 1996-09-27 PL PL96316321A patent/PL316321A1/xx unknown
- 1996-09-30 JP JP8276901A patent/JPH09124606A/ja active Pending
-
2000
- 2000-06-14 CN CN00118801A patent/CN1282737A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9602685A2 (hu) | 1998-09-28 |
| CA2186717A1 (fr) | 1997-03-29 |
| CN1282737A (zh) | 2001-02-07 |
| JPH09124606A (ja) | 1997-05-13 |
| NO308600B1 (no) | 2000-10-02 |
| EP0765871A1 (fr) | 1997-04-02 |
| MX9604378A (es) | 1997-03-29 |
| AU728208B2 (en) | 2001-01-04 |
| HUP9602685A3 (en) | 2001-04-28 |
| IL119302A0 (en) | 1996-12-05 |
| US5726305A (en) | 1998-03-10 |
| CN1154365A (zh) | 1997-07-16 |
| CZ283396A3 (en) | 1997-04-16 |
| EP0765871B1 (fr) | 2004-03-31 |
| KR970061869A (ko) | 1997-09-12 |
| MY133647A (en) | 2007-11-30 |
| NO964093L (no) | 1997-04-01 |
| NO964093D0 (no) | 1996-09-27 |
| DE59610950D1 (de) | 2004-05-06 |
| IL135495A (en) | 2002-12-01 |
| NZ299455A (en) | 1997-06-24 |
| CN1120157C (zh) | 2003-09-03 |
| ATE263155T1 (de) | 2004-04-15 |
| AU6583896A (en) | 1997-04-10 |
| HU9602685D0 (en) | 1996-11-28 |
| PL316321A1 (en) | 1997-04-01 |
| SG45503A1 (en) | 1998-01-16 |
| US5719164A (en) | 1998-02-17 |
| ES2215184T3 (es) | 2004-10-01 |
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