CZ153594A3 - Therapeutically active substances - Google Patents
Therapeutically active substances Download PDFInfo
- Publication number
- CZ153594A3 CZ153594A3 CZ941535A CZ153594A CZ153594A3 CZ 153594 A3 CZ153594 A3 CZ 153594A3 CZ 941535 A CZ941535 A CZ 941535A CZ 153594 A CZ153594 A CZ 153594A CZ 153594 A3 CZ153594 A3 CZ 153594A3
- Authority
- CZ
- Czechia
- Prior art keywords
- group
- carbon atoms
- formula
- alkyl
- hydrogen atom
- Prior art date
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- 239000013543 active substance Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 88
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 60
- 239000001257 hydrogen Substances 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 8
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 4
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims abstract description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 3
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims abstract 2
- -1 alicyclic hydrocarbon radical Chemical class 0.000 claims description 100
- 125000004432 carbon atom Chemical group C* 0.000 claims description 89
- 125000005843 halogen group Chemical group 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000004494 ethyl ester group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 7
- 208000025747 Rheumatic disease Diseases 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 2
- MFQRHPQDMCQXGL-UHFFFAOYSA-N 6-ethoxy-n-(4-methoxyphenyl)-7-methyl-1,8-naphthyridin-4-amine Chemical compound C1=CN=C2N=C(C)C(OCC)=CC2=C1NC1=CC=C(OC)C=C1 MFQRHPQDMCQXGL-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- AQZNKLJRHSWVOV-UHFFFAOYSA-N ethyl 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2N=C(C)C(OCC)=CC2=C1NC1=CC=C(OC)C=C1 AQZNKLJRHSWVOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- KHVFTTVPXONUEK-UHFFFAOYSA-N 4-[(6-ethoxy-7-methyl-1,8-naphthyridin-4-yl)amino]-2,6-dimethylphenol Chemical compound C1=CN=C2N=C(C)C(OCC)=CC2=C1NC1=CC(C)=C(O)C(C)=C1 KHVFTTVPXONUEK-UHFFFAOYSA-N 0.000 claims 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- WPMPEBNPWUMGRJ-UHFFFAOYSA-N ethyl 7-ethoxy-4-(4-methoxyanilino)-1,8-naphthyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2N=C(OCC)C=CC2=C1NC1=CC=C(OC)C=C1 WPMPEBNPWUMGRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 108700026220 vif Genes Proteins 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 129
- 239000003435 antirheumatic agent Substances 0.000 abstract description 5
- 125000001589 carboacyl group Chemical group 0.000 abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 103
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- 238000003756 stirring Methods 0.000 description 25
- 239000007787 solid Substances 0.000 description 24
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 206010039073 rheumatoid arthritis Diseases 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000003628 erosive effect Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 201000008482 osteoarthritis Diseases 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- HLTDBMHJSBSAOM-UHFFFAOYSA-N 2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CC=N1 HLTDBMHJSBSAOM-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000005662 Paraffin oil Substances 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000002702 enteric coating Substances 0.000 description 4
- 238000009505 enteric coating Methods 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 201000004595 synovitis Diseases 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YUHXVWQQUNUOGH-UHFFFAOYSA-N 3-ethoxy-2-methylpyridine Chemical compound CCOC1=CC=CN=C1C YUHXVWQQUNUOGH-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- ADHVKJKRZSDQSU-UHFFFAOYSA-N 5-chloro-3-ethoxy-2-methyl-1,8-naphthyridine Chemical compound C1=CN=C2N=C(C)C(OCC)=CC2=C1Cl ADHVKJKRZSDQSU-UHFFFAOYSA-N 0.000 description 2
- HSVAGTSDJPAWEZ-UHFFFAOYSA-N 6-ethoxy-n-(4-methoxyphenyl)-7-methyl-1,8-naphthyridin-4-amine;hydrochloride Chemical compound Cl.C1=CN=C2N=C(C)C(OCC)=CC2=C1NC1=CC=C(OC)C=C1 HSVAGTSDJPAWEZ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Rheumatology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919127252A GB9127252D0 (en) | 1991-12-23 | 1991-12-23 | Therapeutic agents |
| CN93109454A CN1096784A (zh) | 1991-12-23 | 1993-06-22 | 含取代4(5)-氨基-1,8-二氨杂萘的治疗剂 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ153594A3 true CZ153594A3 (en) | 1995-02-15 |
Family
ID=36822317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ941535A CZ153594A3 (en) | 1991-12-23 | 1992-12-12 | Therapeutically active substances |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5464781A (enExample) |
| EP (1) | EP0618916B1 (enExample) |
| JP (1) | JP2527917B2 (enExample) |
| CN (1) | CN1096784A (enExample) |
| AT (1) | ATE171452T1 (enExample) |
| AU (1) | AU656832B2 (enExample) |
| BG (1) | BG98813A (enExample) |
| CA (1) | CA2125858A1 (enExample) |
| CZ (1) | CZ153594A3 (enExample) |
| DE (1) | DE69227125T2 (enExample) |
| FI (1) | FI943019A7 (enExample) |
| GB (1) | GB9127252D0 (enExample) |
| HR (1) | HRP921455A2 (enExample) |
| HU (1) | HUT66971A (enExample) |
| IL (1) | IL104169A0 (enExample) |
| IN (1) | IN174405B (enExample) |
| MX (1) | MX9207494A (enExample) |
| NO (1) | NO942376L (enExample) |
| NZ (1) | NZ246156A (enExample) |
| SI (1) | SI9200408A (enExample) |
| SK (1) | SK75094A3 (enExample) |
| WO (1) | WO1993013097A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9312891D0 (en) * | 1993-06-22 | 1993-08-04 | Boots Co Plc | Therapeutic agents |
| GB9318931D0 (en) * | 1993-09-14 | 1993-10-27 | Boots Co Plc | Therapeutic agents |
| GB9420168D0 (en) * | 1994-10-06 | 1994-11-23 | Boots Co Plc | Therapeutic agents |
| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| WO1998013350A1 (en) | 1996-09-25 | 1998-04-02 | Zeneca Limited | Qinoline derivatives inhibiting the effect of growth factors such as vegf |
| GB9800569D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
| US6166069A (en) * | 1998-05-12 | 2000-12-26 | American Home Products Corporation | Phenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| JP2003504363A (ja) | 1999-07-09 | 2003-02-04 | グラクソ グループ リミテッド | プロテインチロシンキナーゼ阻害剤としてのアニリノキナゾリン類 |
| US6933299B1 (en) | 1999-07-09 | 2005-08-23 | Smithkline Beecham Corporation | Anilinoquinazolines as protein tyrosine kinase inhibitors |
| AU779695B2 (en) | 2000-04-07 | 2005-02-10 | Astrazeneca Ab | Quinazoline compounds |
| US6534656B2 (en) * | 2001-05-31 | 2003-03-18 | North Carolina State University | Short synthesis of pyridine-based pharmaceutical intermediates |
| JP2003329989A (ja) * | 2002-03-06 | 2003-11-19 | Nippon Telegr & Teleph Corp <Ntt> | 光送信装置 |
| GB0230018D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| CN1984660B (zh) | 2003-07-03 | 2010-12-15 | 美瑞德生物工程公司 | 作为天冬氨酸特异性半胱氨酸蛋白酶活化剂和细胞程序死亡诱导剂的4-芳基氨基-喹唑啉 |
| US8309562B2 (en) * | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| KR100807920B1 (ko) | 2003-12-23 | 2008-02-27 | 화이자 인코포레이티드 | 신규한 퀴놀린 유도체 |
| EP1833482A4 (en) | 2005-01-03 | 2011-02-16 | Myriad Genetics Inc | COMPOUNDS AND ITS THERAPEUTIC USE |
| US8258145B2 (en) * | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| EP2345652A1 (en) | 2005-12-21 | 2011-07-20 | Abbott Laboratories | Antiviral compounds |
| RU2467007C2 (ru) | 2005-12-21 | 2012-11-20 | Эбботт Лэборетриз | Производные [1,8]нафтиридина, полезные в качестве ингибиторов репликации вируса hcv |
| ES2395386T3 (es) * | 2005-12-21 | 2013-02-12 | Abbott Laboratories | Compuestos antivirales |
| RU2441869C2 (ru) * | 2005-12-21 | 2012-02-10 | Эбботт Лэборетриз | Противовирусные соединения |
| TWI392676B (zh) * | 2005-12-21 | 2013-04-11 | Abbott Lab | 抗病毒化合物、其製備方法及用途 |
| CA2672737A1 (en) | 2006-12-20 | 2008-11-06 | Abbott Laboratories | Anti-viral compounds |
| KR20110025856A (ko) * | 2008-07-03 | 2011-03-11 | 메르크 파텐트 게엠베하 | 오로라 키나아제 억제제로서 나프티리디니논 |
| US8415333B2 (en) | 2009-02-24 | 2013-04-09 | Respiratorious Ab | Bronchodilating diazaheteroaryls |
| WO2011063398A1 (en) * | 2009-11-23 | 2011-05-26 | Cylene Pharamaceuticals, Inc. | Polymorphs and salts of a kinase inhibitor |
| NZ603332A (en) | 2010-04-02 | 2014-11-28 | Senomyx Inc | Sweet flavor modifier |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4466965A (en) * | 1982-07-26 | 1984-08-21 | American Hospital Supply Corporation | Phthalazine compounds, compositions and use |
| NZ213986A (en) * | 1984-10-30 | 1989-07-27 | Usv Pharma Corp | Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such |
| EP0222839A4 (en) * | 1985-05-17 | 1988-11-09 | Univ Australian | ANTI-MALARIA COMPOUNDS. |
| JPS6368568A (ja) * | 1986-09-10 | 1988-03-28 | Otsuka Pharmaceut Factory Inc | ｐ−アミノフエノ−ル誘導体 |
| DE3644825A1 (de) * | 1986-12-31 | 1988-07-14 | Basf Ag | Substituierte 1,8-naphthyridin-derivate und diese enthaltende fungizide |
| EP0302303A3 (en) * | 1987-07-22 | 1989-05-24 | Schering Corporation | Bicyclic compounds, their use as pharmaceuticals, their preparation, and intermediates useful in their preparation |
| GB8804443D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| US4978661A (en) * | 1988-09-29 | 1990-12-18 | Innocenzo Caruso | Use of 6-halo-4-quinolone compounds and pharmaceutical compositions thereof for the preparation of a medicament for the therapeutical application in rheumatoid arthritis |
| GR900100380A (el) * | 1989-05-20 | 1991-10-10 | Fisons Plc | Μέ?οδος παρασκευής αντι-φλεγμονωδών παραγώγων αμινοφενόλης. |
| AU634561B2 (en) * | 1989-07-27 | 1993-02-25 | Eli Lilly And Company | Naphthyridine derivatives |
| JP2988739B2 (ja) * | 1990-04-16 | 1999-12-13 | 協和醗酵工業株式会社 | １，８−ナフチリジン−２−オン誘導体 |
| JP3157077B2 (ja) * | 1994-02-16 | 2001-04-16 | 内山工業株式会社 | ベアリングシール |
-
1991
- 1991-12-23 GB GB919127252A patent/GB9127252D0/en active Pending
-
1992
- 1992-10-12 US US08/244,369 patent/US5464781A/en not_active Expired - Lifetime
- 1992-12-12 EP EP93900052A patent/EP0618916B1/en not_active Expired - Lifetime
- 1992-12-12 AU AU31587/93A patent/AU656832B2/en not_active Ceased
- 1992-12-12 CZ CZ941535A patent/CZ153594A3/cs unknown
- 1992-12-12 AT AT93900052T patent/ATE171452T1/de not_active IP Right Cessation
- 1992-12-12 WO PCT/EP1992/002901 patent/WO1993013097A1/en not_active Ceased
- 1992-12-12 DE DE69227125T patent/DE69227125T2/de not_active Expired - Fee Related
- 1992-12-12 HU HU9401877A patent/HUT66971A/hu unknown
- 1992-12-12 JP JP5511397A patent/JP2527917B2/ja not_active Expired - Fee Related
- 1992-12-12 SK SK750-94A patent/SK75094A3/sk unknown
- 1992-12-12 NZ NZ246156A patent/NZ246156A/en unknown
- 1992-12-12 CA CA002125858A patent/CA2125858A1/en not_active Abandoned
- 1992-12-17 IN IN758MA1992 patent/IN174405B/en unknown
- 1992-12-18 IL IL104169A patent/IL104169A0/xx unknown
- 1992-12-22 MX MX9207494A patent/MX9207494A/es unknown
- 1992-12-22 HR HR921455A patent/HRP921455A2/hr not_active Application Discontinuation
- 1992-12-22 SI SI19929200408A patent/SI9200408A/sl unknown
-
1993
- 1993-06-22 CN CN93109454A patent/CN1096784A/zh active Pending
-
1994
- 1994-05-31 BG BG98813A patent/BG98813A/bg unknown
- 1994-06-22 FI FI943019A patent/FI943019A7/fi not_active Application Discontinuation
- 1994-06-22 NO NO942376A patent/NO942376L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU3158793A (en) | 1993-07-28 |
| HUT66971A (en) | 1995-01-30 |
| JPH07502280A (ja) | 1995-03-09 |
| NZ246156A (en) | 1996-01-26 |
| DE69227125T2 (de) | 1999-02-18 |
| FI943019A0 (fi) | 1994-06-22 |
| HRP921455A2 (en) | 1994-12-31 |
| SK75094A3 (en) | 1995-04-12 |
| JP2527917B2 (ja) | 1996-08-28 |
| NO942376D0 (enExample) | 1994-06-22 |
| FI943019A7 (fi) | 1994-06-22 |
| MX9207494A (es) | 1993-07-01 |
| ATE171452T1 (de) | 1998-10-15 |
| AU656832B2 (en) | 1995-02-16 |
| BG98813A (bg) | 1995-05-31 |
| HU9401877D0 (en) | 1994-09-28 |
| EP0618916B1 (en) | 1998-09-23 |
| CN1096784A (zh) | 1994-12-28 |
| IN174405B (enExample) | 1994-11-26 |
| WO1993013097A1 (en) | 1993-07-08 |
| EP0618916A1 (en) | 1994-10-12 |
| DE69227125D1 (de) | 1998-10-29 |
| NO942376L (no) | 1994-06-22 |
| GB9127252D0 (en) | 1992-02-19 |
| SI9200408A (en) | 1993-09-30 |
| US5464781A (en) | 1995-11-07 |
| CA2125858A1 (en) | 1993-07-08 |
| IL104169A0 (en) | 1993-05-13 |
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