CS277018B6 - Process for preparing novel pharmacologically active derivatives of catechol - Google Patents
Process for preparing novel pharmacologically active derivatives of catechol Download PDFInfo
- Publication number
- CS277018B6 CS277018B6 CS888440A CS844087A CS277018B6 CS 277018 B6 CS277018 B6 CS 277018B6 CS 888440 A CS888440 A CS 888440A CS 844087 A CS844087 A CS 844087A CS 277018 B6 CS277018 B6 CS 277018B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- optionally substituted
- dihydroxy
- yield
- found
- alkyl
- Prior art date
Links
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- -1 cyano, carboxyl Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- RGVBYMSUVGONHN-UHFFFAOYSA-N piperazin-2-ylidenemethanone Chemical group O=C=C1CNCCN1 RGVBYMSUVGONHN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- JNHOFPQUTOBFOM-UHFFFAOYSA-N 4-methyl-3-nitrocatechol Chemical group CC1=CC=C(O)C(O)=C1[N+]([O-])=O JNHOFPQUTOBFOM-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 82
- 239000000047 product Substances 0.000 description 65
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 229910052799 carbon Inorganic materials 0.000 description 55
- 229910052757 nitrogen Inorganic materials 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- BBFJODMCHICIAA-UHFFFAOYSA-N 3,4-dihydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC(C=O)=CC([N+]([O-])=O)=C1O BBFJODMCHICIAA-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- 102000006378 Catechol O-methyltransferase Human genes 0.000 description 24
- 108020002739 Catechol O-methyltransferase Proteins 0.000 description 24
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 23
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 23
- 229960004502 levodopa Drugs 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 238000009835 boiling Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 210000002966 serum Anatomy 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
- 102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 description 7
- 108010035075 Tyrosine decarboxylase Proteins 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 102000010909 Monoamine Oxidase Human genes 0.000 description 6
- 108010062431 Monoamine oxidase Proteins 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229960003638 dopamine Drugs 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 230000002093 peripheral effect Effects 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- VDCDWNDTNSWDFJ-UHFFFAOYSA-N 3,5-dinitrocatechol Chemical compound OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O VDCDWNDTNSWDFJ-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 150000003943 catecholamines Chemical class 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- ALWIABFWRLEAKP-UHFFFAOYSA-N 5-(hydroxymethyl)-3-nitrobenzene-1,2-diol Chemical compound OCC1=CC(O)=C(O)C([N+]([O-])=O)=C1 ALWIABFWRLEAKP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 208000018737 Parkinson disease Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000008499 blood brain barrier function Effects 0.000 description 4
- 210000001218 blood-brain barrier Anatomy 0.000 description 4
- 229960004205 carbidopa Drugs 0.000 description 4
- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- 230000004060 metabolic process Effects 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- NOFJIFYZDAAYQQ-UHFFFAOYSA-N 3,4-diacetyloxy-5-nitrobenzoic acid Chemical compound CC(=O)OC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1OC(C)=O NOFJIFYZDAAYQQ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000005013 brain tissue Anatomy 0.000 description 3
- XOPOEBVTQYAOSV-UHFFFAOYSA-N butyl 3,4,5-trihydroxybenzoate Chemical compound CCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 XOPOEBVTQYAOSV-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- CFLAYISSADVCJH-UHFFFAOYSA-N 2,6-dimethylbenzoyl chloride Chemical compound CC1=CC=CC(C)=C1C(Cl)=O CFLAYISSADVCJH-UHFFFAOYSA-N 0.000 description 2
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- VUGQIIQFXCXZJU-UHFFFAOYSA-N 3,4,5-trimethoxyacetophenone Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1OC VUGQIIQFXCXZJU-UHFFFAOYSA-N 0.000 description 2
- DRUCSFHPUMZHFZ-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=CC=2C=C(C(O)=C(O)C=2)[N+]([O-])=O)=C1 DRUCSFHPUMZHFZ-UHFFFAOYSA-N 0.000 description 2
- UVNLFDRZXWSAQU-UHFFFAOYSA-N 3-cyano-4,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(C#N)=C1 UVNLFDRZXWSAQU-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- YZJVWIUMDDXVEA-UHFFFAOYSA-N 4,5-dihydroxybenzene-1,3-dicarbaldehyde Chemical compound OC1=CC(C=O)=CC(C=O)=C1O YZJVWIUMDDXVEA-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- KANXHIGRABCNET-UHFFFAOYSA-N 5-formyl-2,3-dihydroxybenzonitrile Chemical compound OC1=CC(C=O)=CC(C#N)=C1O KANXHIGRABCNET-UHFFFAOYSA-N 0.000 description 2
- ZEHYRTJBFMZHCY-UHFFFAOYSA-N 5-nitrovanillin Chemical compound COC1=CC(C=O)=CC([N+]([O-])=O)=C1O ZEHYRTJBFMZHCY-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 2
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- IQZLUWLMQNGTIW-UHFFFAOYSA-N acetoveratrone Chemical compound COC1=CC=C(C(C)=O)C=C1OC IQZLUWLMQNGTIW-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 229940079919 digestives enzyme preparation Drugs 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- KZGBADQGBKGUGS-UHFFFAOYSA-N ethyl 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoate Chemical compound CCOC(=O)C(C#N)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 KZGBADQGBKGUGS-UHFFFAOYSA-N 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 2
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 2
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- ILPPXXONOPVBRH-UHFFFAOYSA-N (2-acetyloxy-3,5-dinitrophenyl) acetate Chemical compound CC(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(C)=O ILPPXXONOPVBRH-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N (2-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- HDVRRRKTYZBMIN-UHFFFAOYSA-N (2-butanoyloxy-3,5-dinitrophenyl) butanoate Chemical compound CCCC(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)CCC HDVRRRKTYZBMIN-UHFFFAOYSA-N 0.000 description 1
- MEIAEBUHNIBMIE-UHFFFAOYSA-N (2-hydroxy-3,5-dinitrophenyl) 1-methylcyclohexane-1-carboxylate Chemical compound C=1C([N+]([O-])=O)=CC([N+]([O-])=O)=C(O)C=1OC(=O)C1(C)CCCCC1 MEIAEBUHNIBMIE-UHFFFAOYSA-N 0.000 description 1
- WTVJRTGYZDYQKQ-UHFFFAOYSA-N (2-hydroxy-3,5-dinitrophenyl) 2,6-dimethoxybenzoate Chemical compound COC1=CC=CC(OC)=C1C(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O WTVJRTGYZDYQKQ-UHFFFAOYSA-N 0.000 description 1
- FPIBJZQVGJVNJX-UHFFFAOYSA-N (2-hydroxy-3,5-dinitrophenyl) 2,6-dimethylbenzoate Chemical compound CC1=CC=CC(C)=C1C(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O FPIBJZQVGJVNJX-UHFFFAOYSA-N 0.000 description 1
- VSODBRDFKFLWAA-UHFFFAOYSA-N (2-hydroxy-3,5-dinitrophenyl) benzoate Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C1OC(=O)C1=CC=CC=C1 VSODBRDFKFLWAA-UHFFFAOYSA-N 0.000 description 1
- RKSUGISBLQBEOP-UHFFFAOYSA-N (2-hydroxy-3,5-dinitrophenyl) butanoate Chemical compound CCCC(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O RKSUGISBLQBEOP-UHFFFAOYSA-N 0.000 description 1
- XAYGDRSDGBQVSW-UHFFFAOYSA-N (2-hydroxyphenyl) 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC=CC=C1O XAYGDRSDGBQVSW-UHFFFAOYSA-N 0.000 description 1
- UTCONHFSIFTRPV-HMMKTVFPSA-N (2e,5e)-2,5-bis[(3,4-dihydroxy-5-nitrophenyl)methylidene]cyclopentan-1-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(\C=C/2C(C(=C/C=3C=C(C(O)=C(O)C=3)[N+]([O-])=O)/CC\2)=O)=C1 UTCONHFSIFTRPV-HMMKTVFPSA-N 0.000 description 1
- FRKGVRUSKMHMHK-JEDNCBNOSA-N (2s)-2-amino-3-(3,4-dihydroxy-5-nitrophenyl)propanoic acid;hydrobromide Chemical compound Br.OC(=O)[C@@H](N)CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 FRKGVRUSKMHMHK-JEDNCBNOSA-N 0.000 description 1
- PIONCBYVXNKDLA-LURJTMIESA-N (2s)-2-amino-3-(4-hydroxy-3-methoxy-5-nitrophenyl)propanoic acid Chemical compound COC1=CC(C[C@H](N)C(O)=O)=CC([N+]([O-])=O)=C1O PIONCBYVXNKDLA-LURJTMIESA-N 0.000 description 1
- OXGOWGGJQJJUAJ-UHFFFAOYSA-N (3,5-dinitro-2-propanoyloxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)CC OXGOWGGJQJJUAJ-UHFFFAOYSA-N 0.000 description 1
- VHJLVAABSRFDPM-UHFFFAOYSA-N 1,4-dithiothreitol Chemical compound SCC(O)C(O)CS VHJLVAABSRFDPM-UHFFFAOYSA-N 0.000 description 1
- YTGLKZTVRNTRFM-UHFFFAOYSA-N 1-(3,4-dihydroxy-5-nitrophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one Chemical compound C1=CC(N(C)C)=CC=C1C=CC(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 YTGLKZTVRNTRFM-UHFFFAOYSA-N 0.000 description 1
- RZTRFWLYXYIRAX-UHFFFAOYSA-N 1-(3,4-dihydroxy-5-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 RZTRFWLYXYIRAX-UHFFFAOYSA-N 0.000 description 1
- VNTWJPNLLBXHIY-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-5-(3,4-dihydroxy-5-nitrophenyl)pentan-1-one;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=C(O)C(O)=CC(CCCCC(=O)N2CCN(CC=3C=CC=CC=3)CC2)=C1 VNTWJPNLLBXHIY-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- STPXIOFWKOIYHX-UHFFFAOYSA-N 1-methylcyclohexane-1-carbonyl chloride Chemical compound ClC(=O)C1(C)CCCCC1 STPXIOFWKOIYHX-UHFFFAOYSA-N 0.000 description 1
- 229940002520 2'-hydroxyacetophenone Drugs 0.000 description 1
- AXMCFMRWTCCPDA-UHFFFAOYSA-N 2,2-dimethylpropyl 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoate Chemical compound CC(C)(C)COC(=O)C(C#N)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 AXMCFMRWTCCPDA-UHFFFAOYSA-N 0.000 description 1
- MKXONZIDTWQRSO-UHFFFAOYSA-N 2,2-dimethylpropyl 2-cyanoacetate Chemical compound CC(C)(C)COC(=O)CC#N MKXONZIDTWQRSO-UHFFFAOYSA-N 0.000 description 1
- NNQAESZIAYMADQ-UHFFFAOYSA-N 2,3-dihydroxy-5-nitrobenzonitrile Chemical compound OC1=CC([N+]([O-])=O)=CC(C#N)=C1O NNQAESZIAYMADQ-UHFFFAOYSA-N 0.000 description 1
- XHPDHXXZBWDFIB-UHFFFAOYSA-N 2,3-dihydroxybenzonitrile Chemical compound OC1=CC=CC(C#N)=C1O XHPDHXXZBWDFIB-UHFFFAOYSA-N 0.000 description 1
- NDXRPDJVAUCBOH-UHFFFAOYSA-N 2,6-dimethoxybenzoyl chloride Chemical compound COC1=CC=CC(OC)=C1C(Cl)=O NDXRPDJVAUCBOH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SBPVYFCVGGEBHS-UHFFFAOYSA-N 2-[(3,4-dihydroxy-5-nitrophenyl)methyl]-3-hydroxypropanenitrile Chemical compound OCC(C#N)CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 SBPVYFCVGGEBHS-UHFFFAOYSA-N 0.000 description 1
- CEPGLYJLJRCFFW-UHFFFAOYSA-N 2-[(3,4-dihydroxy-5-nitrophenyl)methyl]propanedinitrile Chemical compound OC1=CC(CC(C#N)C#N)=CC([N+]([O-])=O)=C1O CEPGLYJLJRCFFW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BVNUFRQBMSNFBH-UHFFFAOYSA-N 2-[3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 BVNUFRQBMSNFBH-UHFFFAOYSA-N 0.000 description 1
- QDAWXRKTSATEOP-UHFFFAOYSA-N 2-acetylbenzoic acid Chemical compound CC(=O)C1=CC=CC=C1C(O)=O QDAWXRKTSATEOP-UHFFFAOYSA-N 0.000 description 1
- JRURYQJSLYLRLN-UHFFFAOYSA-N 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide Chemical compound CCN(CC)C(=O)C(C#N)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-UHFFFAOYSA-N 0.000 description 1
- WCXPSMYVWFMUPT-UHFFFAOYSA-N 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C#N)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 WCXPSMYVWFMUPT-UHFFFAOYSA-N 0.000 description 1
- NGYPAALNWRGOQF-UHFFFAOYSA-N 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-n-(3-hydroxypropyl)prop-2-enamide Chemical compound OCCCNC(=O)C(C#N)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 NGYPAALNWRGOQF-UHFFFAOYSA-N 0.000 description 1
- NUDNKWSJIXVGSR-UHFFFAOYSA-N 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C#N)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 NUDNKWSJIXVGSR-UHFFFAOYSA-N 0.000 description 1
- IZXCSWDOAKESAA-UHFFFAOYSA-N 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enamide Chemical compound NC(=O)C(C#N)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 IZXCSWDOAKESAA-UHFFFAOYSA-N 0.000 description 1
- PTDWEZSSIVHKSU-UHFFFAOYSA-N 2-cyano-n-(3-hydroxypropyl)acetamide Chemical compound OCCCNC(=O)CC#N PTDWEZSSIVHKSU-UHFFFAOYSA-N 0.000 description 1
- LOAHXFVORLJMML-UHFFFAOYSA-N 2-cyano-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CC#N LOAHXFVORLJMML-UHFFFAOYSA-N 0.000 description 1
- ZBBIAWJRDSAGIX-UHFFFAOYSA-N 2-hydroxy-3-methoxy-5-nitrobenzonitrile Chemical compound COC1=CC([N+]([O-])=O)=CC(C#N)=C1O ZBBIAWJRDSAGIX-UHFFFAOYSA-N 0.000 description 1
- YOQVTEGXOLPDTD-UHFFFAOYSA-N 3,4-diacetyloxy-5-chlorobenzoic acid Chemical compound CC(=O)OC1=CC(C(O)=O)=CC(Cl)=C1OC(C)=O YOQVTEGXOLPDTD-UHFFFAOYSA-N 0.000 description 1
- WXWAAQMUALBCDM-UHFFFAOYSA-N 3,4-diacetyloxy-5-cyanobenzoic acid Chemical compound CC(=O)OC1=CC(C(O)=O)=CC(C#N)=C1OC(C)=O WXWAAQMUALBCDM-UHFFFAOYSA-N 0.000 description 1
- JRBDMOJXCREXNN-UHFFFAOYSA-N 3,4-dihydroxy-5-nitrobenzonitrile Chemical compound OC1=CC(C#N)=CC([N+]([O-])=O)=C1O JRBDMOJXCREXNN-UHFFFAOYSA-N 0.000 description 1
- AJRXNFCZYZBKKT-UHFFFAOYSA-N 3,4-dihydroxy-n-(3-hydroxypropyl)-5-nitrobenzamide Chemical compound OCCCNC(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 AJRXNFCZYZBKKT-UHFFFAOYSA-N 0.000 description 1
- WMVQYGLKWBXMMT-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=CC=CC=C1C(=O)C=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 WMVQYGLKWBXMMT-UHFFFAOYSA-N 0.000 description 1
- GQBUCKFJGCPIAT-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)C=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 GQBUCKFJGCPIAT-UHFFFAOYSA-N 0.000 description 1
- XFNCZWUJTMVCCW-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)C=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 XFNCZWUJTMVCCW-UHFFFAOYSA-N 0.000 description 1
- KEEJYRVPFGKFOM-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)-1-(4-methylphenyl)prop-2-en-1-one Chemical compound C1=CC(C)=CC=C1C(=O)C=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 KEEJYRVPFGKFOM-UHFFFAOYSA-N 0.000 description 1
- LBDCLHWQPHVBTC-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)-1-(4-nitrophenyl)prop-2-en-1-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=CC(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 LBDCLHWQPHVBTC-UHFFFAOYSA-N 0.000 description 1
- GOWRJXXUELPHCD-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)-1-phenylprop-2-en-1-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=CC(=O)C=2C=CC=CC=2)=C1 GOWRJXXUELPHCD-UHFFFAOYSA-N 0.000 description 1
- VPCLKKWUDVSKID-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)propanethioic s-acid Chemical compound OC(=S)CCC1=CC(O)=C(O)C([N+]([O-])=O)=C1 VPCLKKWUDVSKID-UHFFFAOYSA-N 0.000 description 1
- DQJDDRBJBVKKBY-UHFFFAOYSA-N 3-(4-hydroxy-3-methoxy-5-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound [O-][N+](=O)C1=C(O)C(OC)=CC(C=CC(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 DQJDDRBJBVKKBY-UHFFFAOYSA-N 0.000 description 1
- PQFQIWNHGCVXIB-UHFFFAOYSA-N 3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enoic acid Chemical compound COC1=CC(C=CC(O)=O)=CC([N+]([O-])=O)=C1O PQFQIWNHGCVXIB-UHFFFAOYSA-N 0.000 description 1
- ICVODPFGWCUVJC-UHFFFAOYSA-N 3-bromo-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(Br)=C1OC ICVODPFGWCUVJC-UHFFFAOYSA-N 0.000 description 1
- AMZCHEDPEAQEMC-UHFFFAOYSA-N 3-chloro-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(Cl)=C1OC AMZCHEDPEAQEMC-UHFFFAOYSA-N 0.000 description 1
- YLDREYVTINLSNE-UHFFFAOYSA-N 3-chloro-n,n-diethyl-4,5-dimethoxybenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC(Cl)=C(OC)C(OC)=C1 YLDREYVTINLSNE-UHFFFAOYSA-N 0.000 description 1
- JSHLOPGSDZTEGQ-UHFFFAOYSA-N 3-methoxy-4-phenylmethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 JSHLOPGSDZTEGQ-UHFFFAOYSA-N 0.000 description 1
- JSTMJRRWBOVARV-UHFFFAOYSA-N 3-nitro-5-(1h-pyrrol-2-ylmethyl)benzene-1,2-diol Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(CC=2NC=CC=2)=C1 JSTMJRRWBOVARV-UHFFFAOYSA-N 0.000 description 1
- MQOJOPBNUNCZGI-UHFFFAOYSA-N 3-nitro-5-(2-pyridin-4-ylethenyl)benzene-1,2-diol Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=CC=2C=CN=CC=2)=C1 MQOJOPBNUNCZGI-UHFFFAOYSA-N 0.000 description 1
- KRPOYUUBZXFYOJ-UHFFFAOYSA-N 4-(3,4-dihydroxy-5-nitrophenyl)-3-methylbut-3-en-2-one Chemical compound CC(=O)C(C)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 KRPOYUUBZXFYOJ-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- HAZURIXPAQNHDV-UHFFFAOYSA-N 4-[2-(3-carboxypropyl)-3,4-dihydroxyphenyl]butanoic acid Chemical compound C1=CC(=C(C(=C1CCCC(=O)O)CCCC(=O)O)O)O HAZURIXPAQNHDV-UHFFFAOYSA-N 0.000 description 1
- FONUUYDZGOCKNY-UHFFFAOYSA-N 4-acetyloxy-3-cyano-5-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(C#N)=C1OC(C)=O FONUUYDZGOCKNY-UHFFFAOYSA-N 0.000 description 1
- BVTGNOGSGLFHGO-UHFFFAOYSA-N 4-chloro-5-methoxy-2-nitrophenol Chemical compound COC1=CC(O)=C([N+]([O-])=O)C=C1Cl BVTGNOGSGLFHGO-UHFFFAOYSA-N 0.000 description 1
- QKCCIYGCPIDODX-UHFFFAOYSA-N 4-hydroxy-5-methoxybenzene-1,3-dicarbonitrile Chemical compound COC1=CC(C#N)=CC(C#N)=C1O QKCCIYGCPIDODX-UHFFFAOYSA-N 0.000 description 1
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 description 1
- XLZYKBWZDZHAGM-UHFFFAOYSA-N 4-o-[2-(4-ethoxy-4-oxobutanoyl)oxy-3,5-dinitrophenyl] 1-o-ethyl butanedioate Chemical compound CCOC(=O)CCC(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)CCC(=O)OCC XLZYKBWZDZHAGM-UHFFFAOYSA-N 0.000 description 1
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 1
- NMLXKCGWGRMMJM-UHFFFAOYSA-N 5-(3,4-dihydroxy-5-nitrophenyl)-n-propan-2-ylpentanamide Chemical compound CC(C)NC(=O)CCCCC1=CC(O)=C(O)C([N+]([O-])=O)=C1 NMLXKCGWGRMMJM-UHFFFAOYSA-N 0.000 description 1
- MJUWWBJMGJMFRR-UHFFFAOYSA-N 5-(3,4-dihydroxy-5-nitrophenyl)pentanoic acid Chemical compound OC(=O)CCCCC1=CC(O)=C(O)C([N+]([O-])=O)=C1 MJUWWBJMGJMFRR-UHFFFAOYSA-N 0.000 description 1
- RSFRYHVTJAZYRX-UHFFFAOYSA-N 5-(3-chloro-3,5-dimethoxycyclohexa-1,5-dien-1-yl)pentanoic acid Chemical compound COC1=CC(CCCCC(O)=O)=CC(Cl)(OC)C1 RSFRYHVTJAZYRX-UHFFFAOYSA-N 0.000 description 1
- NDFGAEFSDVIKBY-UHFFFAOYSA-N 5-(3-chloro-4,5-dihydroxyphenyl)pentanoic acid Chemical compound OC(=O)CCCCC1=CC(O)=C(O)C(Cl)=C1 NDFGAEFSDVIKBY-UHFFFAOYSA-N 0.000 description 1
- QBTBCGVYYZJWLL-UHFFFAOYSA-N 5-(3-chloro-4,5-dimethoxyphenyl)penta-2,4-dienoic acid Chemical compound COC1=CC(C=CC=CC(O)=O)=CC(Cl)=C1OC QBTBCGVYYZJWLL-UHFFFAOYSA-N 0.000 description 1
- WWDJBWMMHXMHND-UHFFFAOYSA-N 5-(3-hydroxy-2-methylbut-1-enyl)-3-nitrobenzene-1,2-diol Chemical compound CC(O)C(C)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 WWDJBWMMHXMHND-UHFFFAOYSA-N 0.000 description 1
- QFGKFUXIYCPRDG-UHFFFAOYSA-N 5-(3-methoxy-4-phenylmethoxyphenyl)penta-2,4-dienoic acid Chemical compound COC1=CC(C=CC=CC(O)=O)=CC=C1OCC1=CC=CC=C1 QFGKFUXIYCPRDG-UHFFFAOYSA-N 0.000 description 1
- SMRZGIDXIQIJKZ-UHFFFAOYSA-N 5-(4-hydroxy-3-methoxy-5-nitrophenyl)pentanoic acid Chemical compound COC1=CC(CCCCC(O)=O)=CC([N+]([O-])=O)=C1O SMRZGIDXIQIJKZ-UHFFFAOYSA-N 0.000 description 1
- JQQIWBPHESZYNN-UHFFFAOYSA-N 5-(4-hydroxy-3-methoxyphenyl)pentanoic acid Chemical compound COC1=CC(CCCCC(O)=O)=CC=C1O JQQIWBPHESZYNN-UHFFFAOYSA-N 0.000 description 1
- GXHFTPOHUPPXDP-UHFFFAOYSA-N 5-[3-[3-(3,4-dihydroxy-5-nitrophenyl)-2-methoxypropoxy]-2-methoxypropyl]-3-nitrobenzene-1,2-diol Chemical compound C=1C(O)=C(O)C([N+]([O-])=O)=CC=1CC(OC)COCC(OC)CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 GXHFTPOHUPPXDP-UHFFFAOYSA-N 0.000 description 1
- YUMZFEGWCGNXHR-UHFFFAOYSA-N 5-chloro-3-nitrobenzene-1,2-diol Chemical compound OC1=CC(Cl)=CC([N+]([O-])=O)=C1O YUMZFEGWCGNXHR-UHFFFAOYSA-N 0.000 description 1
- RHFZPDHCWCXLCW-UHFFFAOYSA-N 5-chloro-n,n-diethyl-2,3-dihydroxybenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC(Cl)=CC(O)=C1O RHFZPDHCWCXLCW-UHFFFAOYSA-N 0.000 description 1
- MBSQQVBEWZOIJB-UHFFFAOYSA-N 5-formyl-2,3-dimethoxybenzonitrile Chemical compound COC1=CC(C=O)=CC(C#N)=C1OC MBSQQVBEWZOIJB-UHFFFAOYSA-N 0.000 description 1
- UBFJSCLQBYSJEQ-UHFFFAOYSA-N 7-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-8-oxononanoic acid Chemical compound OC(=O)CCCCCC(C(=O)C)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 UBFJSCLQBYSJEQ-UHFFFAOYSA-N 0.000 description 1
- KNPGTJGXMGNBAY-UHFFFAOYSA-N 8-oxo-nonanoic acid Chemical compound CC(=O)CCCCCCC(O)=O KNPGTJGXMGNBAY-UHFFFAOYSA-N 0.000 description 1
- BOIDUAFSCNHXGP-UHFFFAOYSA-N C#CCNC(=O)CCCCC1=CC(=C(C(=C1)O)O)[N+](=O)[O-] Chemical compound C#CCNC(=O)CCCCC1=CC(=C(C(=C1)O)O)[N+](=O)[O-] BOIDUAFSCNHXGP-UHFFFAOYSA-N 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- RYSHIRFTLKZVIH-UHFFFAOYSA-N N,N-diethylcyanoacetamide Chemical compound CCN(CC)C(=O)CC#N RYSHIRFTLKZVIH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 108091000117 Tyrosine 3-Monooxygenase Proteins 0.000 description 1
- 102000048218 Tyrosine 3-monooxygenases Human genes 0.000 description 1
- QQUVPGFQEJKHST-UHFFFAOYSA-N [2-(2,6-dimethylbenzoyl)oxy-3,5-dinitrophenyl] 2,6-dimethylbenzoate Chemical compound CC1=CC=CC(C)=C1C(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C1=C(C)C=CC=C1C QQUVPGFQEJKHST-UHFFFAOYSA-N 0.000 description 1
- FGMBOCPPYYFLJB-UHFFFAOYSA-N [2-acetyloxy-3-nitro-5-(3-oxo-3-phenylprop-1-enyl)phenyl] acetate Chemical compound [O-][N+](=O)C1=C(OC(C)=O)C(OC(=O)C)=CC(C=CC(=O)C=2C=CC=CC=2)=C1 FGMBOCPPYYFLJB-UHFFFAOYSA-N 0.000 description 1
- CZEJERLLAYSVQJ-UHFFFAOYSA-N [2-acetyloxy-5-(1-adamantylcarbamoyl)-3-chlorophenyl] acetate Chemical compound ClC1=C(OC(C)=O)C(OC(=O)C)=CC(C(=O)NC23CC4CC(CC(C4)C2)C3)=C1 CZEJERLLAYSVQJ-UHFFFAOYSA-N 0.000 description 1
- FGDKGGWWCARTIR-UHFFFAOYSA-N [2-acetyloxy-5-(1-adamantylcarbamoyl)-3-cyanophenyl] acetate Chemical compound N#CC1=C(OC(C)=O)C(OC(=O)C)=CC(C(=O)NC23CC4CC(CC(C4)C2)C3)=C1 FGDKGGWWCARTIR-UHFFFAOYSA-N 0.000 description 1
- UIRWYZJMXSYMTD-UHFFFAOYSA-N [2-acetyloxy-5-(1-adamantylcarbamoyl)-3-nitrophenyl] acetate Chemical compound [O-][N+](=O)C1=C(OC(C)=O)C(OC(=O)C)=CC(C(=O)NC23CC4CC(CC(C4)C2)C3)=C1 UIRWYZJMXSYMTD-UHFFFAOYSA-N 0.000 description 1
- UHPUZYLXKFZVFP-UHFFFAOYSA-N [2-acetyloxy-5-(benzylcarbamoyl)-3-nitrophenyl] acetate Chemical compound [O-][N+](=O)C1=C(OC(C)=O)C(OC(=O)C)=CC(C(=O)NCC=2C=CC=CC=2)=C1 UHPUZYLXKFZVFP-UHFFFAOYSA-N 0.000 description 1
- NTZOGOQNAIGGFG-UHFFFAOYSA-N [2-acetyloxy-5-[4-(cyclohexanecarbonyl)piperidine-1-carbonyl]-3-nitrophenyl] acetate Chemical compound [O-][N+](=O)C1=C(OC(C)=O)C(OC(=O)C)=CC(C(=O)N2CCC(CC2)C(=O)C2CCCCC2)=C1 NTZOGOQNAIGGFG-UHFFFAOYSA-N 0.000 description 1
- WVECYZIRUQVEGW-UHFFFAOYSA-N [2-benzoyloxy-3-nitro-5-(3-oxo-3-phenylprop-1-enyl)phenyl] benzoate Chemical compound C=1C(OC(=O)C=2C=CC=CC=2)=C(OC(=O)C=2C=CC=CC=2)C([N+](=O)[O-])=CC=1C=CC(=O)C1=CC=CC=C1 WVECYZIRUQVEGW-UHFFFAOYSA-N 0.000 description 1
- UBAVSEMCOMZATK-UHFFFAOYSA-N [2-hydroxy-3-nitro-5-(3-oxo-3-phenylprop-1-enyl)phenyl] 2,2-dimethylpropanoate Chemical compound [O-][N+](=O)C1=C(O)C(OC(=O)C(C)(C)C)=CC(C=CC(=O)C=2C=CC=CC=2)=C1 UBAVSEMCOMZATK-UHFFFAOYSA-N 0.000 description 1
- KPHHVYOGNRHXCP-UHFFFAOYSA-N [2-hydroxy-3-nitro-5-(3-oxo-3-phenylprop-1-enyl)phenyl] octadecanoate Chemical compound [O-][N+](=O)C1=C(O)C(OC(=O)CCCCCCCCCCCCCCCCC)=CC(C=CC(=O)C=2C=CC=CC=2)=C1 KPHHVYOGNRHXCP-UHFFFAOYSA-N 0.000 description 1
- QNPGHROFDQAAIB-UHFFFAOYSA-N [5-(2-acetyl-3-oxobut-1-enyl)-2-hydroxy-3-nitrophenyl] 2,2-dimethylpropanoate Chemical compound CC(=O)C(C(C)=O)=CC1=CC(OC(=O)C(C)(C)C)=C(O)C([N+]([O-])=O)=C1 QNPGHROFDQAAIB-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000009056 active transport Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 210000004227 basal ganglia Anatomy 0.000 description 1
- BNQDCRGUHNALGH-UHFFFAOYSA-N benserazide Chemical compound OCC(N)C(=O)NNCC1=CC=C(O)C(O)=C1O BNQDCRGUHNALGH-UHFFFAOYSA-N 0.000 description 1
- 229960000911 benserazide Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- MNAQSDCWEZWEAF-UHFFFAOYSA-N butyl 3-cyano-4,5-dihydroxybenzoate Chemical compound CCCCOC(=O)C1=CC(O)=C(O)C(C#N)=C1 MNAQSDCWEZWEAF-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- XBILPYQIGZIQEK-UHFFFAOYSA-N cyclohexyl(piperidin-1-yl)methanone Chemical compound C1CCCCN1C(=O)C1CCCCC1 XBILPYQIGZIQEK-UHFFFAOYSA-N 0.000 description 1
- BSSKJZZQJGXADF-UHFFFAOYSA-N cyclohexyl-[1-(3,4-dihydroxy-5-nitrobenzoyl)piperidin-4-yl]methanone Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C(=O)N2CCC(CC2)C(=O)C2CCCCC2)=C1 BSSKJZZQJGXADF-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 210000005064 dopaminergic neuron Anatomy 0.000 description 1
- YSKILQPVKFEWDD-UHFFFAOYSA-N ethyl 2-[[2-hydroxy-3-nitro-5-(3-oxo-3-phenylprop-1-enyl)phenoxy]carbonylamino]acetate Chemical compound [O-][N+](=O)C1=C(O)C(OC(=O)NCC(=O)OCC)=CC(C=CC(=O)C=2C=CC=CC=2)=C1 YSKILQPVKFEWDD-UHFFFAOYSA-N 0.000 description 1
- PLQOHSJGIYXROC-UHFFFAOYSA-N ethyl 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)propanoate Chemical compound CCOC(=O)C(C#N)CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 PLQOHSJGIYXROC-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- DUVOZUPPHBRJJO-UHFFFAOYSA-N ethyl 2-isocyanatoacetate Chemical compound CCOC(=O)CN=C=O DUVOZUPPHBRJJO-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- YUYXUNQTIKONFA-UHFFFAOYSA-N methyl 3-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 YUYXUNQTIKONFA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RPUFERHPLAVBJN-UHFFFAOYSA-N n,n-dihydroxy-1-phenylmethanamine Chemical compound ON(O)CC1=CC=CC=C1 RPUFERHPLAVBJN-UHFFFAOYSA-N 0.000 description 1
- IALCRFZLEQENBW-UHFFFAOYSA-N n-(1-adamantyl)-3,4-dihydroxy-5-nitrobenzamide Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C(=O)NC23CC4CC(CC(C4)C2)C3)=C1 IALCRFZLEQENBW-UHFFFAOYSA-N 0.000 description 1
- YLRRYFLYJYRKJG-UHFFFAOYSA-N n-(1-adamantyl)-3-chloro-4,5-dihydroxybenzamide Chemical compound ClC1=C(O)C(O)=CC(C(=O)NC23CC4CC(CC(C4)C2)C3)=C1 YLRRYFLYJYRKJG-UHFFFAOYSA-N 0.000 description 1
- RLPFJGCLLIGOMQ-UHFFFAOYSA-N n-(1-adamantyl)-3-cyano-4,5-dihydroxybenzamide Chemical compound N#CC1=C(O)C(O)=CC(C(=O)NC23CC4CC(CC(C4)C2)C3)=C1 RLPFJGCLLIGOMQ-UHFFFAOYSA-N 0.000 description 1
- OENSXLFBMLMJOF-UHFFFAOYSA-N n-(1-adamantyl)-5-(3,4-dihydroxy-5-nitrophenyl)pentanamide Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(CCCCC(=O)NC23CC4CC(CC(C4)C2)C3)=C1 OENSXLFBMLMJOF-UHFFFAOYSA-N 0.000 description 1
- CCRNCWDQAOTBHN-UHFFFAOYSA-N n-benzyl-3,4-dihydroxy-5-nitrobenzamide Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C(=O)NCC=2C=CC=CC=2)=C1 CCRNCWDQAOTBHN-UHFFFAOYSA-N 0.000 description 1
- HQFYIDOMCULPIW-UHFFFAOYSA-N n-methylprop-2-yn-1-amine Chemical compound CNCC#C HQFYIDOMCULPIW-UHFFFAOYSA-N 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- PGKVPHVPNDBJTO-UHFFFAOYSA-N nitroapocynin Chemical compound COC1=CC(C(C)=O)=CC([N+]([O-])=O)=C1O PGKVPHVPNDBJTO-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- PJZQPGWMGLBVEA-UHFFFAOYSA-N tetradecyl 5-(3,4-diacetyloxy-5-nitrophenyl)pentanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCC1=CC(OC(C)=O)=C(OC(C)=O)C([N+]([O-])=O)=C1 PJZQPGWMGLBVEA-UHFFFAOYSA-N 0.000 description 1
- QZJHVSWEEUPIEC-UHFFFAOYSA-N tetradecyl 5-(3,4-dihydroxy-5-nitrophenyl)pentanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCC1=CC(O)=C(O)C([N+]([O-])=O)=C1 QZJHVSWEEUPIEC-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/22—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/23—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having two nitro groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/34—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/24—[b,e]-condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI864875A FI864875A0 (fi) | 1986-11-28 | 1986-11-28 | Nya farmakologiskt aktiva foereningar, dessa innehaollande kompositioner samt foerfarande och mellanprodukter foer anvaendning vid framstaellning av dessa. |
| GB878712437A GB8712437D0 (en) | 1986-11-28 | 1987-05-27 | Pharmacologically active compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS277018B6 true CS277018B6 (en) | 1992-11-18 |
Family
ID=26158050
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS888440A CS277018B6 (en) | 1986-11-28 | 1987-11-27 | Process for preparing novel pharmacologically active derivatives of catechol |
| CS888439A CS276263B6 (en) | 1986-11-28 | 1987-11-27 | Process for preparing novel pharmacologically active derivatives of catechol |
| CS888440A CS844088A3 (en) | 1986-11-28 | 1988-12-19 | Process for preparing novel pharmacologically active derivatives of catechol |
| CS888439A CS843988A3 (en) | 1986-11-28 | 1988-12-19 | Process for preparing novel pharmacologically active derivatives of catechol |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS888439A CS276263B6 (en) | 1986-11-28 | 1987-11-27 | Process for preparing novel pharmacologically active derivatives of catechol |
| CS888440A CS844088A3 (en) | 1986-11-28 | 1988-12-19 | Process for preparing novel pharmacologically active derivatives of catechol |
| CS888439A CS843988A3 (en) | 1986-11-28 | 1988-12-19 | Process for preparing novel pharmacologically active derivatives of catechol |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US4963590A (it) |
| JP (2) | JP2735834B2 (it) |
| CN (1) | CN1040062C (it) |
| AR (1) | AR243491A1 (it) |
| AT (1) | AT401053B (it) |
| AU (1) | AU621036B2 (it) |
| BE (1) | BE1003279A5 (it) |
| BG (1) | BG60407B2 (it) |
| CA (2) | CA1334967C (it) |
| CH (1) | CH685436A5 (it) |
| CS (4) | CS277018B6 (it) |
| DE (2) | DE19975025I2 (it) |
| DK (1) | DK175394B1 (it) |
| EG (1) | EG18338A (it) |
| ES (1) | ES2008359A6 (it) |
| FR (1) | FR2607493B1 (it) |
| GB (1) | GB2200109B (it) |
| GR (1) | GR871817B (it) |
| HK (1) | HK75594A (it) |
| HU (1) | HU206073B (it) |
| IE (1) | IE60320B1 (it) |
| IS (1) | IS1753B (it) |
| IT (1) | IT1225762B (it) |
| LU (1) | LU87050A1 (it) |
| LV (1) | LV10236B (it) |
| MA (1) | MA21120A1 (it) |
| MT (1) | MTP1012B (it) |
| NL (2) | NL194821C (it) |
| NO (1) | NO171450C (it) |
| NZ (1) | NZ222729A (it) |
| PH (1) | PH26145A (it) |
| PL (1) | PL152642B1 (it) |
| PT (1) | PT86236B (it) |
| RU (1) | RU2014319C1 (it) |
| SE (1) | SE503434C2 (it) |
| YU (3) | YU213587A (it) |
Families Citing this family (140)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5236952A (en) * | 1986-03-11 | 1993-08-17 | Hoffmann-La Roche Inc. | Catechol derivatives |
| US5283352A (en) * | 1986-11-28 | 1994-02-01 | Orion-Yhtyma Oy | Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same |
| GB9004348D0 (en) * | 1990-02-27 | 1990-04-25 | Orion Yhtymae Oy | New use of catechol derivatives and their physiologically acceptable salts and esters |
| AU632992B2 (en) * | 1987-12-24 | 1993-01-21 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Pharmaceutical compositions comprising benzylidene- and cinnamylidene-malononitrile derivatives for the inhibition of proliferative processes in mammalian cells, certain such novel compounds and their preparation |
| MTP1031B (en) * | 1987-12-24 | 1990-10-04 | Orion Yhtymae Oy | New use of cathecol-o-methyl transferase (comt) inhibitors and their physiologically acceptable salts and esters |
| US5232923A (en) * | 1988-03-18 | 1993-08-03 | Mitsui Toatsu Chemicals, Incorporated | Catechol derivatives and pharmaceutical preparations containing same |
| US5063243A (en) * | 1988-04-28 | 1991-11-05 | Suntory, Ltd. | Derivative of caffeic acid and pharmaceutical composition containing the same |
| US5185370A (en) * | 1988-09-01 | 1993-02-09 | Orion-Yhtyma Oy | Substituted β-diketones and their use |
| GB9002337D0 (en) * | 1990-02-02 | 1990-04-04 | Orion Yhtymae Oy | Compounds useful in treating inflammatory bowel disease |
| IL91382A (en) * | 1988-09-01 | 1995-06-29 | Orion Yhtymae Oy | Alkenyl or arylmethylene-substituted beta-diketones their preparation and pharmaceutical compositions containing them |
| JPH085780B2 (ja) * | 1989-04-28 | 1996-01-24 | 呉羽化学工業株式会社 | 変形性関節症治療剤 |
| GB2238047B (en) * | 1989-11-03 | 1993-02-10 | Orion Yhtymae Oy | Stable polymorphic form of (e)-n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide and the process for its preparation |
| GB9113431D0 (en) * | 1991-06-20 | 1991-08-07 | Orion Yhytma Oy | Method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde |
| JPH05301838A (ja) * | 1991-10-15 | 1993-11-16 | Mitsubishi Kasei Corp | スチレン誘導体 |
| ES2179071T3 (es) * | 1993-04-07 | 2003-01-16 | Otsuka Pharma Co Ltd | Agentes vasodilatadores perifericos que comprenden como principio activo derivados de la piperidina 4-amino n-acilada. |
| GB9419274D0 (en) * | 1994-09-23 | 1994-11-09 | Orion Yhtymae Oy | New method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde |
| GB9510481D0 (en) * | 1995-05-24 | 1995-07-19 | Orion Yhtymae Oy | New catechol derivatives |
| GB2316944B (en) * | 1995-05-24 | 1999-01-20 | Orion Yhtymae Oy | New catechol derivatives |
| GB9626472D0 (en) | 1996-12-20 | 1997-02-05 | Aperia Anita C | New use of comt inhibitors |
| FI981521A0 (fi) | 1998-07-01 | 1998-07-01 | Orion Corp | Substituoidut beta-diketonit ja niiden käyttö |
| US6599530B2 (en) * | 1998-09-14 | 2003-07-29 | Orion Corporation | Oral compacted composition comprising catechol derivatives |
| GB2344819A (en) * | 1998-12-18 | 2000-06-21 | Portela & Ca Sa | 2-Phenyl-1-(3,4-dihydroxy-5-nitrophenyl)-1-ethanones |
| US7015338B1 (en) * | 1999-04-15 | 2006-03-21 | Mars Incorporated | Synthetic methods for preparing procyanidin oligomers |
| FI20000635A0 (fi) * | 2000-03-17 | 2000-03-17 | Orion Yhtymae Oyj | COMT-inhibiittoreiden käyttö analgeettina |
| US6486210B2 (en) * | 2000-04-14 | 2002-11-26 | Temple University—Of the Commonwealth System of Higher Education | Substituted styryl benzylsulfones for treating proliferative disorders |
| FI20012242A0 (fi) * | 2001-11-19 | 2001-11-19 | Orion Corp | Uudet farmaseuttiset yhdisteet |
| US20060013875A1 (en) * | 2002-05-29 | 2006-01-19 | Impax Laboratories, Inc. | Combination immediate release controlled release levodopa/carbidopa dosage forms |
| US7094427B2 (en) * | 2002-05-29 | 2006-08-22 | Impax Laboratories, Inc. | Combination immediate release controlled release levodopa/carbidopa dosage forms |
| US8158149B2 (en) * | 2004-05-12 | 2012-04-17 | Chelsea Therapeutics, Inc. | Threo-DOPS controlled release formulation |
| US20060105036A1 (en) | 2003-05-12 | 2006-05-18 | Stephen Peroutka | Threo-dops controlled release formulation |
| US20070010584A1 (en) * | 2003-09-04 | 2007-01-11 | Peroutka Stephen J | Compositions and methods for orthostatic intolerance |
| AU2003296838A1 (en) * | 2003-12-24 | 2005-08-11 | Siddiqui Mohammed Jaweed Mukarram | An efficient process for the manufacture of (e)-entacapone polymorphic form a |
| AU2003288712B2 (en) * | 2003-12-29 | 2010-11-04 | Suven Life Sciences Ltd | Alternative process for the preparation of entacapone |
| WO2005066117A1 (en) * | 2003-12-29 | 2005-07-21 | Wockhardt Limited | Stable polymorphs of (e)-n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide |
| MY142362A (en) | 2004-01-29 | 2010-11-30 | Otsuka Pharma Co Ltd | Pharmaceutical composition for promoting angiogenesis |
| WO2005110462A2 (en) | 2004-05-04 | 2005-11-24 | Children's Medical Center Corporation | Methods and compositions for treatment of preeclampsia |
| US8138342B2 (en) * | 2004-10-12 | 2012-03-20 | High Point Pharmacueticals, LLC | 11β-hydroxysteroid dehydrogenase type 1 active spiro compounds |
| IL169855A (en) * | 2005-07-25 | 2014-05-28 | Elta Systems Ltd | A system and method for locating a receiver location |
| DK1907382T3 (en) | 2005-07-26 | 2015-08-31 | Bial Portela & Ca Sa | Nitrocatecholderivater comt inhibitors as |
| AU2006310519A1 (en) * | 2005-11-01 | 2007-05-10 | High Point Pharmaceuticals, Llc | Pharmaceutical use of substituted amides |
| EA200801243A1 (ru) * | 2005-11-01 | 2008-10-30 | Транстек Фарма | Фармацевтическое применение замещенных амидов |
| ATE445591T1 (de) * | 2005-11-09 | 2009-10-15 | Usv Ltd | Verfahren zur herstellung von hochreinem (e)-n,n- diethyl-2-cyano-3-(3,4-dihydro-5- nitrophenyl)acrylamid (entacapon) |
| EP1976824A1 (en) * | 2006-01-02 | 2008-10-08 | Actavis Group PTC EHF | A process for the preparation of entacapone form-a |
| EA014912B1 (ru) * | 2006-02-06 | 2011-02-28 | Орион Корпорейшн | Способ получения энтакапона |
| CA2646588A1 (en) * | 2006-03-21 | 2007-09-27 | High Point Pharmaceuticals, Llc | Adamantane derivatives for the treatment of the metabolic syndrome |
| WO2007113845A1 (en) * | 2006-04-03 | 2007-10-11 | Alembic Limited | A process for the preparation of (e)-2-cyano-3-(3, 4-dihydroxy-5-nitrophenyl)-n, n-diethyl-2-propenamide (entacapone) |
| EP2010479A1 (en) | 2006-04-07 | 2009-01-07 | High Point Pharmaceuticals, LLC | 11 beta-hydroxysteroid dehydrogenase type 1 active compounds |
| EP1845097A1 (en) * | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| EP2038255A2 (en) * | 2006-06-16 | 2009-03-25 | High Point Pharmaceuticals, LLC | Pharmaceutical use of substituted piperidine carboxamides |
| PL1948155T3 (pl) | 2006-06-28 | 2012-10-31 | Chelsea Therapeutics Inc | Kompozycje farmaceutyczne zawierające droksidopę |
| US20080004343A1 (en) * | 2006-06-29 | 2008-01-03 | Wockhardt Limited | Stable polymorphs of (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide |
| EP1878721A1 (en) * | 2006-07-13 | 2008-01-16 | Novo Nordisk A/S | 4-Piperidylbenzamides as 11-beta-hydroxysteroid dehydrogenase type 1 inhibitors |
| US8048908B2 (en) * | 2006-07-13 | 2011-11-01 | High Point Pharmaceuticals, Llc | 11β-hydroxysteroid dehydrogenase type 1 active compounds |
| EP2099933A4 (en) | 2006-11-21 | 2010-03-24 | Beth Israel Hospital | HYPOXIA-ASSOCIATED GENES AND PROTEINS FOR THE TREATMENT AND DIAGNOSIS OF PREGNANCY-RELATED COMPLICATIONS |
| ES2597705T3 (es) | 2007-01-31 | 2017-01-20 | Bial - Portela & Ca., S.A. | Derivados de nitrocatecol como inhibidores de COMT administrados con un régimen de dosificación específico |
| ES2319024B1 (es) | 2007-02-13 | 2009-12-11 | Quimica Sintetica, S.A. | Procedimiento para la obtencion de entacapona sustancialmente libre de isomero z, sus intermedios de sintesis y nueva forma cristalina. |
| EP2146952A1 (en) * | 2007-02-23 | 2010-01-27 | High Point Pharmaceuticals, LLC | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
| WO2008101886A1 (en) * | 2007-02-23 | 2008-08-28 | High Point Pharmaceuticals, Llc | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
| EP2129652A2 (en) * | 2007-02-23 | 2009-12-09 | High Point Pharmaceuticals, LLC | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
| MX2009008228A (es) | 2007-02-23 | 2009-08-12 | High Point Pharmaceuticals Llc | N-adamantil benzamidas como inhibidores de la dehidrogenasa 11-beta-hidroxiesteroide. |
| CN101652359A (zh) * | 2007-03-09 | 2010-02-17 | 高点制药有限责任公司 | 作为羟类固醇脱氢酶抑制剂的吲哚-和苯并咪唑酰胺类 |
| ES2500053T3 (es) | 2007-03-09 | 2014-09-29 | Chelsea Therapeutics, Inc. | Composición farmacéutica que comprende droxidopa para el tratamiento de la fibromialgia |
| WO2008119017A1 (en) * | 2007-03-28 | 2008-10-02 | High Point Pharmaceuticals, Llc | 11beta-hsd1 active compounds |
| EP1978014A1 (en) * | 2007-04-02 | 2008-10-08 | Esteve Quimica, S.A. | Process for the preparation of entacapone and intermediates thereof |
| ES2399912T3 (es) * | 2007-04-11 | 2013-04-04 | High Point Pharmaceuticals, Llc | Nuevos compuestos |
| CN101711106B (zh) * | 2007-04-24 | 2013-02-06 | 高点制药有限责任公司 | 取代的酰胺类的药物应用 |
| US8383681B2 (en) | 2007-05-07 | 2013-02-26 | Chelsea Therapeutics, Inc. | Droxidopa and pharmaceutical composition thereof for the treatment of mood disorders, sleep disorders or attention deficit disorders |
| WO2009084031A2 (en) * | 2007-12-03 | 2009-07-09 | Neuland Laboratories Ltd | An improved process for preparation of (2e)-2-cyano-3-(3,4- dihydroxy-5-nitrophenyl)n,n-diethyl-2-propenamide polymorphic form a |
| US20110015158A1 (en) | 2007-12-11 | 2011-01-20 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
| CA2708447C (en) | 2007-12-25 | 2016-05-10 | Kissei Pharmaceutical Co., Ltd. | Novel catechol derivative, pharmaceutical composition containing the same, use of the catechol derivative, and use of the pharmaceutical composition |
| CA2715802A1 (en) * | 2008-02-28 | 2009-09-03 | Bial - Portela & C.A., S.A. | Pharmaceutical composition for poorly soluble drugs |
| CA2718772C (en) | 2008-03-17 | 2017-05-02 | David Alexander Learmonth | Crystal forms of 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nit robenzene-1,2-diol |
| ES2402562T3 (es) | 2008-07-04 | 2013-05-06 | Kissei Pharmaceutical Co., Ltd. | Derivado de catecol y su uso |
| CA2744383C (en) * | 2008-11-21 | 2017-04-25 | High Point Pharmaceuticals, Llc | Adamantyl benzamide compounds |
| PL2413912T3 (pl) | 2009-04-01 | 2019-09-30 | Bial-Portela & Ca, S.A. | Preparaty farmaceutyczne zawierające pochodne nitrokatecholu oraz metody ich wytwarzania |
| CN102438595B (zh) * | 2009-04-01 | 2016-04-27 | 巴尔-波特拉及康邦亚股份有限公司 | 包括硝基儿茶酚衍生物的药物制剂及其制备方法 |
| CN102816082B (zh) * | 2010-01-29 | 2015-03-11 | 浙江大学 | 苯甲酰胺类衍生物及制备方法和应用 |
| CN101817761B (zh) * | 2010-01-29 | 2014-06-25 | 浙江大学 | 苯甲酸酯类衍生物及制备方法和应用 |
| ES2496093T3 (es) * | 2010-04-15 | 2014-09-18 | Merck Patent Gmbh | Proceso para la preparación de hidroquinonas |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| JP5880913B2 (ja) | 2011-05-17 | 2016-03-09 | 三郎 佐古田 | パーキンソン病の体幹症状(姿勢反射異常)の治療剤 |
| JPWO2012157612A1 (ja) * | 2011-05-19 | 2014-07-31 | 国立大学法人徳島大学 | 細胞分化誘導剤および分化誘導方法 |
| WO2014037832A2 (en) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment of epilepsy and neurological diseases |
| PT3604299T (pt) | 2011-12-13 | 2023-10-31 | Bial Portela & Ca Sa | Composto químico útil como intermediário para a preparação de um inibidor de catecol-o-metiltransferase |
| SG11201404496PA (en) | 2012-01-31 | 2014-12-30 | Lundbeck Na Ltd | Improving postural stability administering droxidopa |
| WO2013167985A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological disorders |
| WO2013167990A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of depression |
| CA2873093A1 (en) | 2012-05-07 | 2013-11-14 | Cellixbio Private Limited | Compositions and methods for treatment of neuromuscular disorders and neurodegenerative disorders |
| US9266823B2 (en) | 2012-05-08 | 2016-02-23 | Cellix Bio Private Limited | Compositions and methods for the treatment of parkinson's disease |
| US9309233B2 (en) | 2012-05-08 | 2016-04-12 | Cellix Bio Private Limited | Compositions and methods for the treatment of blood clotting disorders |
| WO2013167993A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological degenerative disorders |
| WO2013167992A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of inflammatory disorders |
| US9522884B2 (en) | 2012-05-08 | 2016-12-20 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic disorders |
| US9573927B2 (en) | 2012-05-10 | 2017-02-21 | Cellix Bio Private Limited | Compositions and methods for the treatment of severe pain |
| WO2013168002A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological conditions |
| WO2013168014A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of familial amyloid polyneuropathy |
| US9273061B2 (en) | 2012-05-10 | 2016-03-01 | Cellix Bio Private Limited | Compositions and methods for the treatment of chronic pain |
| US9403857B2 (en) | 2012-05-10 | 2016-08-02 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| WO2013168001A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| WO2013167999A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurologic diseases |
| WO2013168033A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of neurologic diseases |
| WO2013168004A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of fibromyalgia pain |
| WO2013168012A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of respiratory disorders |
| WO2013167997A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic syndrome |
| WO2013168005A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of restless leg syndrome and fibromyalgia |
| US9394288B2 (en) | 2012-05-10 | 2016-07-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of asthma and allergy |
| SG11201407322QA (en) | 2012-05-23 | 2014-12-30 | Cellix Bio Private Ltd | Compositions and methods for the treatment of multiple sclerosis |
| WO2013175376A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of local pain |
| CN104583182A (zh) | 2012-05-23 | 2015-04-29 | 塞利克斯比奥私人有限公司 | 用于治疗粘膜炎的组合物和方法 |
| US9227974B2 (en) | 2012-05-23 | 2016-01-05 | Cellex Bio Private Limited | Compositions and methods for the treatment of respiratory disorders |
| US9434729B2 (en) | 2012-05-23 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of periodontitis and rheumatoid arthritis |
| AU2013264894B2 (en) | 2012-05-23 | 2015-11-19 | Cellix Bio Private Limited | Compositions and methods for treatment of inflammatory bowel disease |
| TWI638802B (zh) * | 2012-05-24 | 2018-10-21 | 芬蘭商奧利安公司 | 兒茶酚o-甲基轉移酶活性抑制化合物 |
| US9108942B1 (en) | 2014-11-05 | 2015-08-18 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| US9187427B2 (en) | 2012-08-03 | 2015-11-17 | Cellix Bio Private Limited | N-substituted nicotinamide compounds and compositions for the treatment migraine and neurologic diseases |
| WO2014037833A2 (en) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment inflammation and lipid disorders |
| WO2014037834A2 (en) | 2012-09-08 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment of inflammation and lipid disorders |
| US9333187B1 (en) | 2013-05-15 | 2016-05-10 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory bowel disease |
| AU2014276346A1 (en) | 2013-06-04 | 2015-12-24 | Cellixbio Private Limited | Compositions and methods for the treatment of diabetes and pre-diabetes |
| AU2014332024B2 (en) | 2013-10-07 | 2019-09-26 | Impax Laboratories, Llc | Muco-adhesive, controlled release formulations of levodopa and/or esters of levodopa and uses thereof |
| US9096537B1 (en) | 2014-12-31 | 2015-08-04 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
| CA2976314C (en) | 2014-09-26 | 2021-02-23 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy and neurological disorders |
| SG11201702554QA (en) | 2014-09-29 | 2017-04-27 | Cellix Bio Private Ltd | Compositions and methods for the treatment of multiple sclerosis |
| CN104311426A (zh) * | 2014-10-27 | 2015-01-28 | 厦门大学 | 芳香硝基乙烯化合物的新用途 |
| SG11201703369WA (en) | 2014-10-27 | 2017-05-30 | Cellix Bio Private Ltd | Three component salts of fumaric acid monomethyl ester with piperazine or ethylene diamine for the treatment of multiple sclerosis |
| US10208014B2 (en) | 2014-11-05 | 2019-02-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological disorders |
| US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| US9150557B1 (en) | 2014-11-05 | 2015-10-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of hyperglycemia |
| US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
| US9173877B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
| US9284287B1 (en) | 2014-11-05 | 2016-03-15 | Cellix Bio Private Limited | Compositions and methods for the suppression of carbonic anhydrase activity |
| RU2017120184A (ru) | 2014-11-28 | 2018-12-28 | БИАЛ - ПОРТЕЛА ЭНД Ка, С.А. | Лекарства для замедления течения болезни паркинсона |
| US9932294B2 (en) | 2014-12-01 | 2018-04-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| CA2973178C (en) | 2015-01-06 | 2022-11-01 | Cellix Bio Private Limited | Bupivacaine derivatives and their use in the treatment of inflammation and pain |
| US10532976B2 (en) * | 2015-06-23 | 2020-01-14 | National Institute Of Biological Sciences, Beijing | FTO inhibitors |
| EP3303283B1 (en) * | 2015-06-23 | 2021-04-21 | National Institute Of Biological Sciences, Beijing | Fto inhibitors |
| EP3500246B1 (en) | 2016-08-18 | 2021-08-04 | Ilko Ilaç Sanayi Ve Ticaret Anonim Sirketi | Antiparkinson tablet formulation with improved dissolution profile |
| CN116283664B (zh) * | 2023-01-12 | 2025-05-16 | 中国药科大学 | 一种硝基儿茶酚衍生物、包含其的药物组合物及其应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB902586A (en) * | 1960-01-01 | 1962-08-01 | Shell Res Ltd | Herbicidal compositions and novel compounds for use therein |
| GB1188364A (en) * | 1967-05-02 | 1970-04-15 | May & Baker Ltd | Quinoline Derivatives |
| BE759266A (fr) * | 1969-11-24 | 1971-05-24 | Hoffmann La Roche | Procede pour la preparation de derives de l'indole |
| IE35838B1 (en) * | 1970-12-07 | 1976-06-09 | Reckitt & Colmann Prod Ltd | Pharmaceutical compositions |
| CA1190223A (en) * | 1977-11-01 | 1985-07-09 | Anthony C. Richardson | Substrates for enzymes |
| JPS5890534A (ja) * | 1981-11-25 | 1983-05-30 | Ono Pharmaceut Co Ltd | 2−アミノフエノ−ル誘導体、その製造方法およびその誘導体を有効成分として含有する治療剤 |
| ES8405409A1 (es) * | 1982-04-03 | 1984-06-01 | Beecham Group Plc | Un procedimiento para la preparacion de derivados de b-lactama. |
| ES8505914A1 (es) * | 1983-05-13 | 1985-06-16 | Yamanouchi Pharma Co Ltd | Un procedimiento para la produccion de un derivado de catecol |
| FR2557098B1 (fr) * | 1983-12-22 | 1986-06-13 | Rhone Poulenc Spec Chim | Procede de preparation de bromobenzaldehydes hydroxy et/ou alkoxy substitues |
| FR2557097B1 (fr) * | 1983-12-22 | 1986-06-13 | Rhone Poulenc Spec Chim | Procede de preparation de bromobenzaldehydes hydroxy et/ou alkoxy substitues |
| EP0155335A1 (de) * | 1984-03-21 | 1985-09-25 | LUDWIG HEUMANN & CO GMBH | Verfahren zur Herstellung von 3,5-Dimethoxy-4-alkoxybenzaldehyden |
| DK175069B1 (da) * | 1986-03-11 | 2004-05-24 | Hoffmann La Roche | Pyrocatecholderivater |
| CH679150A5 (it) * | 1986-11-07 | 1991-12-31 | Oreal |
-
1987
- 1987-11-25 YU YU02135/87A patent/YU213587A/xx unknown
- 1987-11-26 CN CN87108011A patent/CN1040062C/zh not_active Expired - Lifetime
- 1987-11-26 MT MT1012A patent/MTP1012B/xx unknown
- 1987-11-26 EG EG689/87A patent/EG18338A/xx active
- 1987-11-27 HU HU875352A patent/HU206073B/hu active Protection Beyond IP Right Term
- 1987-11-27 JP JP62301387A patent/JP2735834B2/ja not_active Expired - Lifetime
- 1987-11-27 NZ NZ222729A patent/NZ222729A/en unknown
- 1987-11-27 CA CA000552987A patent/CA1334967C/en not_active Expired - Lifetime
- 1987-11-27 ES ES8703401A patent/ES2008359A6/es not_active Expired
- 1987-11-27 NO NO874966A patent/NO171450C/no not_active IP Right Cessation
- 1987-11-27 BE BE8701356A patent/BE1003279A5/fr not_active IP Right Cessation
- 1987-11-27 LU LU87050A patent/LU87050A1/fr unknown
- 1987-11-27 PH PH36138A patent/PH26145A/en unknown
- 1987-11-27 GR GR871817A patent/GR871817B/el unknown
- 1987-11-27 CA CA000552986A patent/CA1289078C/en not_active Expired - Lifetime
- 1987-11-27 SE SE8704751A patent/SE503434C2/sv not_active IP Right Cessation
- 1987-11-27 NL NL8702857A patent/NL194821C/nl not_active IP Right Cessation
- 1987-11-27 DK DK198706230A patent/DK175394B1/da not_active IP Right Cessation
- 1987-11-27 IS IS3290A patent/IS1753B/is unknown
- 1987-11-27 PL PL1987269091A patent/PL152642B1/pl unknown
- 1987-11-27 CS CS888440A patent/CS277018B6/cs not_active IP Right Cessation
- 1987-11-27 FR FR878716457A patent/FR2607493B1/fr not_active Expired - Lifetime
- 1987-11-27 AR AR87309418A patent/AR243491A1/es active
- 1987-11-27 CH CH4633/87A patent/CH685436A5/de not_active IP Right Cessation
- 1987-11-27 MA MA21361A patent/MA21120A1/fr unknown
- 1987-11-27 DE DE1999175025 patent/DE19975025I2/de active Active
- 1987-11-27 PT PT86236A patent/PT86236B/pt unknown
- 1987-11-27 US US07/126,911 patent/US4963590A/en not_active Expired - Lifetime
- 1987-11-27 IT IT8722790A patent/IT1225762B/it active Protection Beyond IP Right Term
- 1987-11-27 RU SU4203731/04A patent/RU2014319C1/ru active
- 1987-11-27 DE DE3740383A patent/DE3740383C2/de not_active Expired - Lifetime
- 1987-11-27 AT AT0312987A patent/AT401053B/de not_active IP Right Cessation
- 1987-11-27 JP JP62301388A patent/JPH085781B2/ja not_active Expired - Lifetime
- 1987-11-27 CS CS888439A patent/CS276263B6/cs not_active IP Right Cessation
- 1987-11-27 GB GB8727854A patent/GB2200109B/en not_active Expired - Lifetime
- 1987-11-27 AU AU81879/87A patent/AU621036B2/en not_active Expired
- 1987-11-30 IE IE324287A patent/IE60320B1/en not_active IP Right Cessation
-
1988
- 1988-12-19 CS CS888440A patent/CS844088A3/cs unknown
- 1988-12-19 CS CS888439A patent/CS843988A3/cs unknown
-
1989
- 1989-01-06 YU YU2189A patent/YU48020B/sh unknown
- 1989-01-06 YU YU2289A patent/YU47790B/sh unknown
-
1993
- 1993-06-30 LV LVP-93-805A patent/LV10236B/en unknown
-
1994
- 1994-01-18 BG BG098383A patent/BG60407B2/bg unknown
- 1994-08-04 HK HK75594A patent/HK75594A/xx not_active IP Right Cessation
-
2003
- 2003-09-26 NL NL300136C patent/NL300136I2/nl unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS277018B6 (en) | Process for preparing novel pharmacologically active derivatives of catechol | |
| US5446194A (en) | Pharmacologically active catechol derivatives | |
| US5112861A (en) | Method of treating parkinson's disease using pentanedione derivatives | |
| KR950011120B1 (ko) | 리폭시게나제 억제 화합물 및 이를 함유하는 약제학적 조성물 | |
| IE58801B1 (en) | Subtituted benzene derivatives | |
| SU1156593A3 (ru) | Способ получени производных бензамида или их кислотно-аддитивных солей,или оптических изомеров | |
| US20040034011A1 (en) | Derivatives of naphthalene with comt inhibiting activity | |
| JPS6261960A (ja) | 不可逆性ド−パミン−β−ヒドロキシラ−ゼ抑制剤 | |
| US5202349A (en) | Substituted phenylacetylenes, pharmaceutical compositions containing these compounds and processes for the preparation of these compounds and compositions | |
| JP3163173B2 (ja) | 置換された3,4− ジヒドロナフタリン、これを化合物を含有する薬剤並びにこの化合物及び薬剤を製造する方法 | |
| EP0502110B1 (fr) | Derives d'(hetero) arylmethyloxy-4 phenyl diazole, leur procede de preparation et leur application en therapeutique | |
| US4051251A (en) | Novel anti-hypertensive compositions | |
| CH618963A5 (en) | Process for the preparation of oxanilic acid derivatives | |
| JPS61161275A (ja) | 新規なアリルアミン類 | |
| US4889874A (en) | Hydroxamic acid derivatives and method of using same | |
| CA1106376A (fr) | Procede de preparation de nouveaux esters anthraniliques | |
| BE878563A (fr) | Nouvelles alpha-alkyl-o-oxybenzylamines, leur preparation et leur application comme medicaments |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20071127 |