BG61262B1 - Cyclic derivatives of the aminophenylacetic acid, method fortheir preparation and application - Google Patents
Cyclic derivatives of the aminophenylacetic acid, method fortheir preparation and application Download PDFInfo
- Publication number
- BG61262B1 BG61262B1 BG97173A BG9717392A BG61262B1 BG 61262 B1 BG61262 B1 BG 61262B1 BG 97173 A BG97173 A BG 97173A BG 9717392 A BG9717392 A BG 9717392A BG 61262 B1 BG61262 B1 BG 61262B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- group
- carbon atoms
- substituted
- general formula
- lower alkyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 48
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 title abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 91
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
- 125000005843 halogen group Chemical group 0.000 claims abstract description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 31
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 230000003287 optical effect Effects 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 14
- 125000004429 atom Chemical group 0.000 claims abstract description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims abstract description 8
- 125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 83
- -1 cyclic aminophenylacetic acid derivative Chemical class 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 claims description 3
- 239000003435 antirheumatic agent Substances 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZQICGTYUOSVFMN-UHFFFAOYSA-N Iselin Natural products CC1=C(COc2c3ccoc3cc3oc(=O)ccc23)CC(C)(C)CC1 ZQICGTYUOSVFMN-UHFFFAOYSA-N 0.000 claims 1
- 229920000180 alkyd Polymers 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical group C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical group CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 230000001363 autoimmune Effects 0.000 abstract 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 230000008105 immune reaction Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 118
- 239000002904 solvent Substances 0.000 description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- 239000013078 crystal Substances 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 42
- 239000000047 product Substances 0.000 description 38
- 239000000243 solution Substances 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 238000000921 elemental analysis Methods 0.000 description 29
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- 239000000126 substance Substances 0.000 description 25
- 238000001953 recrystallisation Methods 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 150000004702 methyl esters Chemical class 0.000 description 12
- FZNNUPYZIJYZNG-UHFFFAOYSA-N 2-[2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetic acid Chemical compound N1C(C(F)(F)F)CCC2=CC(CC(=O)O)=CC=C21 FZNNUPYZIJYZNG-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000012467 final product Substances 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 0 *CC(**)=*C1=[C@]=C*C=C1* Chemical compound *CC(**)=*C1=[C@]=C*C=C1* 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- LJIJHRLNRYAOEM-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydroquinolin-6-yl)acetic acid Chemical compound N1CCCC2=CC(CC(=O)O)=CC=C21 LJIJHRLNRYAOEM-UHFFFAOYSA-N 0.000 description 4
- FAPVKZMQDZDPPT-UHFFFAOYSA-N 2-[2-(trifluoromethyl)quinolin-6-yl]acetic acid Chemical compound N1=C(C(F)(F)F)C=CC2=CC(CC(=O)O)=CC=C21 FAPVKZMQDZDPPT-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 210000003743 erythrocyte Anatomy 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000002519 immonomodulatory effect Effects 0.000 description 4
- 230000028993 immune response Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- 206010003246 arthritis Diseases 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
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- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
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- ZIAMEGJVCACAHB-UHFFFAOYSA-N 2-[8-bromo-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetic acid Chemical compound N1C(C(F)(F)F)CCC2=CC(CC(=O)O)=CC(Br)=C21 ZIAMEGJVCACAHB-UHFFFAOYSA-N 0.000 description 2
- MYVZCLGYTGLOOS-UHFFFAOYSA-N 2-[8-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetic acid Chemical compound C1CC(C(F)(F)F)NC2=C1C=C(CC(O)=O)C=C2OC MYVZCLGYTGLOOS-UHFFFAOYSA-N 0.000 description 2
- WRZASMDOYVTJDY-UHFFFAOYSA-N 2-[8-methylsulfanyl-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetic acid Chemical compound C1CC(C(F)(F)F)NC2=C1C=C(CC(O)=O)C=C2SC WRZASMDOYVTJDY-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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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
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- 238000000338 in vitro Methods 0.000 description 2
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- TVIVLENJTXGRAM-UHFFFAOYSA-N methyl 2-(4-aminophenyl)acetate Chemical compound COC(=O)CC1=CC=C(N)C=C1 TVIVLENJTXGRAM-UHFFFAOYSA-N 0.000 description 2
- ZAPGULMEGYWURT-UHFFFAOYSA-N methyl 2-[8-amino-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound COC(CC=1C=C2CCC(NC2=C(C=1)N)C(F)(F)F)=O ZAPGULMEGYWURT-UHFFFAOYSA-N 0.000 description 2
- ASVXHKKKWHQOPU-UHFFFAOYSA-N methyl 2-[8-bromo-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound N1C(C(F)(F)F)CCC2=CC(CC(=O)OC)=CC(Br)=C21 ASVXHKKKWHQOPU-UHFFFAOYSA-N 0.000 description 2
- MBMUCZBHLROROM-UHFFFAOYSA-N methyl 2-[8-methylsulfanyl-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound COC(=O)CC1=CC2=C(C(=C1)SC)NC(CC2)C(F)(F)F MBMUCZBHLROROM-UHFFFAOYSA-N 0.000 description 2
- AMYWPMOAMDYXJO-UHFFFAOYSA-N methyl 2-[8-phenyl-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound COC(CC=1C=C2CCC(NC2=C(C=1)C1=CC=CC=C1)C(F)(F)F)=O AMYWPMOAMDYXJO-UHFFFAOYSA-N 0.000 description 2
- QRIDXWUOPRURFC-UHFFFAOYSA-N methyl 4,4,4-trifluorobut-2-ynoate Chemical compound COC(=O)C#CC(F)(F)F QRIDXWUOPRURFC-UHFFFAOYSA-N 0.000 description 2
- MDAUPQDOKGVZRN-UHFFFAOYSA-N methyl 6-(2-methoxy-2-oxoethyl)-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline-8-carboxylate Chemical compound COC(=O)CC1=CC2=C(C(=C1)C(=O)OC)NC(CC2)C(F)(F)F MDAUPQDOKGVZRN-UHFFFAOYSA-N 0.000 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- RPQZGVMESYTXCC-UHFFFAOYSA-N ethyl 2-[2-(2-fluorophenyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound C1CC2=CC(CC(=O)OCC)=CC=C2NC1C1=CC=CC=C1F RPQZGVMESYTXCC-UHFFFAOYSA-N 0.000 description 1
- IKHXSNAYTFAPGY-UHFFFAOYSA-N ethyl 2-[2-(2-fluorophenyl)-4-oxo-1h-quinolin-6-yl]acetate Chemical compound C1=C(O)C2=CC(CC(=O)OCC)=CC=C2N=C1C1=CC=CC=C1F IKHXSNAYTFAPGY-UHFFFAOYSA-N 0.000 description 1
- WNQILWMRKDSXNF-UHFFFAOYSA-N ethyl 2-[4-chloro-2-(2-fluorophenyl)quinolin-6-yl]acetate Chemical compound C1=C(Cl)C2=CC(CC(=O)OCC)=CC=C2N=C1C1=CC=CC=C1F WNQILWMRKDSXNF-UHFFFAOYSA-N 0.000 description 1
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- 125000004494 ethyl ester group Chemical group 0.000 description 1
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- LEZWWQSOZVUMOK-UHFFFAOYSA-N methyl 2-(4-amino-3-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(N)C(OC)=C1 LEZWWQSOZVUMOK-UHFFFAOYSA-N 0.000 description 1
- GFGOYQKOFLPPHZ-UHFFFAOYSA-N methyl 2-(4-amino-3-methylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(N)C(C)=C1 GFGOYQKOFLPPHZ-UHFFFAOYSA-N 0.000 description 1
- TWOHGMXBWRQYSI-UHFFFAOYSA-N methyl 2-(8-chloro-1-methyl-2-phenyl-3,4-dihydro-2h-quinolin-6-yl)acetate Chemical compound C1CC2=CC(CC(=O)OC)=CC(Cl)=C2N(C)C1C1=CC=CC=C1 TWOHGMXBWRQYSI-UHFFFAOYSA-N 0.000 description 1
- OIGPNWGPTKWMFY-UHFFFAOYSA-N methyl 2-[2-(trifluoromethyl)-8-(2-trimethylsilylethynyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound COC(=O)CC1=CC2=C(C(=C1)C#C[Si](C)(C)C)NC(CC2)C(F)(F)F OIGPNWGPTKWMFY-UHFFFAOYSA-N 0.000 description 1
- AHMNZKXMANHXQY-UHFFFAOYSA-N methyl 2-[4-chloro-2-(trifluoromethyl)quinolin-6-yl]acetate Chemical compound N1=C(C(F)(F)F)C=C(Cl)C2=CC(CC(=O)OC)=CC=C21 AHMNZKXMANHXQY-UHFFFAOYSA-N 0.000 description 1
- SZEGLOJWIRWSGD-UHFFFAOYSA-N methyl 2-[4-chloro-8-methyl-2-(trifluoromethyl)quinolin-6-yl]acetate Chemical compound COC(CC=1C=C2C(=CC(=NC2=C(C=1)C)C(F)(F)F)Cl)=O SZEGLOJWIRWSGD-UHFFFAOYSA-N 0.000 description 1
- WAUXJAUNMRQXFD-UHFFFAOYSA-N methyl 2-[4-oxo-2-(trifluoromethyl)-1h-quinolin-6-yl]acetate Chemical compound N1=C(C(F)(F)F)C=C(O)C2=CC(CC(=O)OC)=CC=C21 WAUXJAUNMRQXFD-UHFFFAOYSA-N 0.000 description 1
- ZRWFZKCFZRZYHN-UHFFFAOYSA-N methyl 2-[8-chloro-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound C1CC2=CC(CC(=O)OC)=CC(Cl)=C2NC1C1=CC=C(OC)C=C1 ZRWFZKCFZRZYHN-UHFFFAOYSA-N 0.000 description 1
- HOOLXHHNDJGPAH-UHFFFAOYSA-N methyl 2-[8-methylsulfonyl-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound COC(=O)CC1=CC2=C(C(=C1)S(=O)(=O)C)NC(CC2)C(F)(F)F HOOLXHHNDJGPAH-UHFFFAOYSA-N 0.000 description 1
- AJKBYVBYMILUQL-UHFFFAOYSA-N methyl 2-[8-nitro-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetate Chemical compound COC(CC=1C=C2CCC(NC2=C(C=1)[N+](=O)[O-])C(F)(F)F)=O AJKBYVBYMILUQL-UHFFFAOYSA-N 0.000 description 1
- ZWHYAHXLFQKJLX-UHFFFAOYSA-N methyl 4,4,4-trifluoro-3-[2-methoxy-4-(2-methoxy-2-oxoethyl)anilino]but-2-enoate Chemical compound COC(=O)CC1=CC=C(NC(=CC(=O)OC)C(F)(F)F)C(OC)=C1 ZWHYAHXLFQKJLX-UHFFFAOYSA-N 0.000 description 1
- KSKUHJXBSPUGHZ-UHFFFAOYSA-N methyl 4,4,4-trifluoro-3-[4-(2-methoxy-2-oxoethyl)anilino]but-2-enoate Chemical compound COC(=O)CC1=CC=C(NC(=CC(=O)OC)C(F)(F)F)C=C1 KSKUHJXBSPUGHZ-UHFFFAOYSA-N 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- 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]
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/63—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/14—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
- C07D215/36—Sulfur 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
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- External Artificial Organs (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11100091 | 1991-04-16 | ||
JP11673092A JP3209568B2 (ja) | 1991-04-16 | 1992-04-10 | 新規環状アミノフェニル酢酸誘導体、その製造法及びそれらを有効成分とする免疫応答の修飾剤 |
PCT/JP1992/000476 WO1992018482A1 (fr) | 1991-04-16 | 1992-04-15 | Nouveau derive d'acide aminophenylacetique, production de ce derive et modulateur de reponse immune contenant ce derive comme principe actif |
Publications (2)
Publication Number | Publication Date |
---|---|
BG97173A BG97173A (bg) | 1993-12-24 |
BG61262B1 true BG61262B1 (en) | 1997-04-30 |
Family
ID=26450490
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG97173A BG61262B1 (en) | 1991-04-16 | 1992-12-15 | Cyclic derivatives of the aminophenylacetic acid, method fortheir preparation and application |
Country Status (19)
Country | Link |
---|---|
US (1) | US5359076A (fr) |
EP (1) | EP0538477B1 (fr) |
JP (1) | JP3209568B2 (fr) |
KR (1) | KR960007085B1 (fr) |
AT (1) | ATE226196T1 (fr) |
AU (1) | AU647612B2 (fr) |
BG (1) | BG61262B1 (fr) |
CA (1) | CA2085347C (fr) |
CZ (1) | CZ282165B6 (fr) |
DE (1) | DE69232812T2 (fr) |
DK (1) | DK0538477T3 (fr) |
ES (1) | ES2184730T3 (fr) |
FI (1) | FI101300B (fr) |
HU (2) | HU9203870D0 (fr) |
NO (1) | NO179174C (fr) |
RO (1) | RO114615B1 (fr) |
SK (1) | SK282146B6 (fr) |
TW (1) | TW203606B (fr) |
WO (1) | WO1992018482A1 (fr) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL112567A (en) * | 1994-02-10 | 2000-02-29 | Wyeth John & Brother Ltd | Substituted quinolines their preparation and pharmaceutical compositions containing them |
WO1999067238A2 (fr) | 1998-06-25 | 1999-12-29 | Sepracor, Inc. | Agents antimicrobiens di- et tetra-hydroquinoline-indol, utilisations et compositions correspondantes |
CN102958919A (zh) * | 2010-07-02 | 2013-03-06 | 霍夫曼-拉罗奇有限公司 | 新的四氢喹啉衍生物 |
US8592594B2 (en) * | 2010-07-02 | 2013-11-26 | Hoffmann-La Roche Inc. | Tetrahydro-quinoline derivatives |
US11084787B2 (en) | 2016-02-10 | 2021-08-10 | Sumitomo Chemical Company Limited | Method for producing 1-methylpyrrolidin-3-ol |
JPWO2022138888A1 (fr) | 2020-12-25 | 2022-06-30 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2042352A1 (fr) * | 1969-04-21 | 1971-02-12 | Ciba Geigy Ag | Acides alpha-(1,2,3,4-tetrahydro-6-quinolyl)-carboxyliques et leurs derives |
CH576447A5 (fr) * | 1972-03-10 | 1976-06-15 | Ciba Geigy Ag | |
JPS5665097A (en) * | 1979-05-30 | 1981-06-02 | Lion Corp | Manufacture of fatty acid lower alcohol ester |
JPS58116466A (ja) * | 1981-12-29 | 1983-07-11 | Nippon Zoki Pharmaceut Co Ltd | 新規キノリル酢酸誘導体及び該化合物を含有する医薬組成物 |
US4956372A (en) * | 1987-10-02 | 1990-09-11 | Kyorin Pharmaceutical Co., Ltd. | Cyclic anthranilic acid derivatives and process for their preparation |
US5124325A (en) * | 1989-06-13 | 1992-06-23 | Kyorin Pharmaceutical Co., Ltd. | Therapeutic agents of metabolic bone disease |
-
1992
- 1992-04-10 JP JP11673092A patent/JP3209568B2/ja not_active Expired - Fee Related
- 1992-04-15 RO RO92-01558A patent/RO114615B1/ro unknown
- 1992-04-15 SK SK3651-92A patent/SK282146B6/sk unknown
- 1992-04-15 CZ CS923651A patent/CZ282165B6/cs not_active IP Right Cessation
- 1992-04-15 HU HU9203870A patent/HU9203870D0/hu unknown
- 1992-04-15 AT AT92908279T patent/ATE226196T1/de not_active IP Right Cessation
- 1992-04-15 US US07/956,012 patent/US5359076A/en not_active Expired - Lifetime
- 1992-04-15 CA CA002085347A patent/CA2085347C/fr not_active Expired - Fee Related
- 1992-04-15 WO PCT/JP1992/000476 patent/WO1992018482A1/fr active IP Right Grant
- 1992-04-15 DK DK92908279T patent/DK0538477T3/da active
- 1992-04-15 HU HU9203870A patent/HU222522B1/hu not_active IP Right Cessation
- 1992-04-15 ES ES92908279T patent/ES2184730T3/es not_active Expired - Lifetime
- 1992-04-15 DE DE69232812T patent/DE69232812T2/de not_active Expired - Fee Related
- 1992-04-15 KR KR1019920703236A patent/KR960007085B1/ko not_active IP Right Cessation
- 1992-04-15 AU AU15549/92A patent/AU647612B2/en not_active Ceased
- 1992-04-15 EP EP92908279A patent/EP0538477B1/fr not_active Expired - Lifetime
- 1992-04-25 TW TW081103268A patent/TW203606B/zh active
- 1992-12-15 BG BG97173A patent/BG61262B1/bg unknown
- 1992-12-15 FI FI925697A patent/FI101300B/fi active
- 1992-12-15 NO NO924854A patent/NO179174C/no unknown
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