ZA200210161B - Coumarin derivatives with COMT inhibiting activity. - Google Patents
Coumarin derivatives with COMT inhibiting activity. Download PDFInfo
- Publication number
- ZA200210161B ZA200210161B ZA200210161A ZA200210161A ZA200210161B ZA 200210161 B ZA200210161 B ZA 200210161B ZA 200210161 A ZA200210161 A ZA 200210161A ZA 200210161 A ZA200210161 A ZA 200210161A ZA 200210161 B ZA200210161 B ZA 200210161B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- cooh
- composition
- substituents
- Prior art date
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- 108020002739 Catechol O-methyltransferase Proteins 0.000 title claims description 17
- 230000002401 inhibitory effect Effects 0.000 title claims description 9
- 102100040999 Catechol O-methyltransferase Human genes 0.000 title claims 2
- 150000001893 coumarin derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- -1 5-tetrazolyl Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 102000006378 Catechol O-methyltransferase Human genes 0.000 description 14
- 125000004076 pyridyl group Chemical group 0.000 description 12
- 125000003831 tetrazolyl group Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 6
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 125000002757 morpholinyl group Chemical group 0.000 description 5
- 125000004193 piperazinyl group Chemical group 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000004775 coumarins Chemical class 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000005936 piperidyl group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CVAKRGWBLNNJJI-UHFFFAOYSA-N 5-(2-aminoethyl)-1-methylcyclohexa-2,4-diene-1,2-diol Chemical compound CC1(O)CC(CCN)=CC=C1O CVAKRGWBLNNJJI-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 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
- 150000007513 acids Chemical class 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical class C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- UNNBMXHASMHOIQ-UHFFFAOYSA-N 4-(2-aminoethyl)-1-methylcyclohexa-3,5-diene-1,2-diol Chemical compound CC1(O)C=CC(CCN)=CC1O UNNBMXHASMHOIQ-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 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 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 101100133572 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nog-2 gene Proteins 0.000 description 1
- 241000080590 Niso Species 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 238000006600 Stobbe condensation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910001506 inorganic fluoride Inorganic materials 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- 150000002515 isoflavone derivatives Chemical class 0.000 description 1
- 235000008696 isoflavones Nutrition 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000006492 vascular dysfunction Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20001593A FI20001593A7 (fi) | 2000-07-03 | 2000-07-03 | Comt-entsyymiõ inhiboivaa aktiivisuutta omaavia kumariinijohdannaisia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200210161B true ZA200210161B (en) | 2004-03-15 |
Family
ID=8558717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200210161A ZA200210161B (en) | 2000-07-03 | 2002-12-13 | Coumarin derivatives with COMT inhibiting activity. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6951870B2 (enExample) |
| EP (1) | EP1301503B1 (enExample) |
| JP (1) | JP4851051B2 (enExample) |
| KR (1) | KR20030040225A (enExample) |
| CN (1) | CN1199963C (enExample) |
| AT (1) | ATE260268T1 (enExample) |
| AU (2) | AU2001272597B9 (enExample) |
| BG (1) | BG107513A (enExample) |
| BR (1) | BR0111969A (enExample) |
| CA (1) | CA2414787C (enExample) |
| DE (1) | DE60102161T2 (enExample) |
| DK (1) | DK1301503T3 (enExample) |
| EE (1) | EE200300008A (enExample) |
| ES (1) | ES2215919T3 (enExample) |
| FI (1) | FI20001593A7 (enExample) |
| HU (1) | HUP0301706A3 (enExample) |
| IL (2) | IL153352A0 (enExample) |
| MX (1) | MXPA02012657A (enExample) |
| NO (1) | NO328699B1 (enExample) |
| NZ (1) | NZ523121A (enExample) |
| PL (1) | PL359068A1 (enExample) |
| PT (1) | PT1301503E (enExample) |
| RU (1) | RU2282627C2 (enExample) |
| SK (1) | SK18452002A3 (enExample) |
| TR (1) | TR200400802T4 (enExample) |
| WO (1) | WO2002002548A1 (enExample) |
| ZA (1) | ZA200210161B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPR846401A0 (en) * | 2001-10-25 | 2001-11-15 | Novogen Research Pty Ltd | 6-Hydroxy isoflavones, derivatives and medicaments involving same |
| AU2003265737B2 (en) * | 2002-10-02 | 2008-10-16 | Novogen Research Pty Ltd | Combination chemotherapy compositions and methods |
| AU2002951833A0 (en) * | 2002-10-02 | 2002-10-24 | Novogen Research Pty Ltd | Compositions and therapeutic methods invloving platinum complexes |
| CN1506359A (zh) | 2002-12-05 | 2004-06-23 | �й�ҽѧ��ѧԺҩ���о��� | 新的香豆素酰胺衍生物及其制法和其药物组合物与用途 |
| CN101056868B (zh) | 2004-09-21 | 2012-05-02 | 马休爱德华兹股份有限公司 | 取代的苯并二氢吡喃衍生物、药物及其在治疗中的应用 |
| US8080675B2 (en) | 2004-09-21 | 2011-12-20 | Marshall Edwards, Inc. | Chroman derivatives, medicaments and use in therapy |
| MY148644A (en) * | 2005-07-18 | 2013-05-15 | Orion Corp | New pharmaceutical compounds |
| EP1917245A1 (de) | 2005-08-21 | 2008-05-07 | Abbott GmbH & Co. KG | Heterocyclische verbindungen und ihre verwendung als bindungspartner für 5-ht5-rezeptoren |
| WO2007124617A1 (fr) * | 2006-04-28 | 2007-11-08 | Institute Of Mataria Medica, Chinese Academy Of Medical Sciences | Dérivés de coumarine, leurs procédés de préparation, compositions pharmaceutiques et utilisations |
| RU2396244C1 (ru) * | 2008-12-23 | 2010-08-10 | Тихоокеанский Институт Биоорганической Химии Дальневосточного Отделения Российской Академии Наук (Тибох Дво Ран) | Способ получения пурпурогаллина |
| ES2343347B2 (es) * | 2009-01-27 | 2011-12-07 | Universidade De Santiago De Compostela | Uso de derivados de 3-fenilcumarinas 6-sustituidas y preparacion de nuevos derivados. |
| JP6013349B2 (ja) | 2010-11-01 | 2016-10-25 | メイ ファーマ, インク.Mei Pharma, Inc. | 癌の処置のためのイソフラボノイド化合物および方法 |
| 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 |
| WO2016126618A1 (en) | 2015-02-02 | 2016-08-11 | Mei Pharma, Inc. | Combination therapies |
| JP7007292B2 (ja) * | 2015-12-18 | 2022-02-10 | ケスター、ヒューバート | 薬剤としての使用のため、特にパーキンソン病の治療のための新規二環式化合物 |
| CN107868069A (zh) * | 2017-10-31 | 2018-04-03 | 山东新华制药股份有限公司 | 7‑羟基‑8‑甲基‑6‑硝基‑2‑氧‑2h‑苯并吡喃‑3‑羧酸的制备工艺 |
| CN116064607B (zh) * | 2022-08-22 | 2025-04-18 | 西南大学 | 一种高活性o-甲基转移酶基因制备滨蒿内酯的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5035393A (enExample) * | 1973-08-01 | 1975-04-04 | ||
| US3973608A (en) * | 1973-08-01 | 1976-08-10 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Microbial production of certain isoflavones |
| 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 |
| GB8816519D0 (en) | 1987-07-23 | 1988-08-17 | Ici Plc | Antibiotic compounds |
| HUT63843A (en) | 1992-02-13 | 1993-10-28 | Biosignal Kutato Fejlesztoe Kf | Process for producing new kumarin derivatives and their analogs inhibiting mammal cell proliferation and tumour growth, as well as pharmaceutical comkpositions comprising such compounds |
| GB9318935D0 (en) * | 1992-10-20 | 1993-10-27 | Zeneca Ltd | Heterocyclic derivatives |
| JP3166094B2 (ja) * | 1993-09-08 | 2001-05-14 | 森永乳業株式会社 | クマリン誘導体及びそれらの用途 |
| JPH0892157A (ja) | 1994-05-02 | 1996-04-09 | F Hoffmann La Roche Ag | プルプロガリン誘導体 |
| GB9626472D0 (en) * | 1996-12-20 | 1997-02-05 | Aperia Anita C | New use of comt inhibitors |
| HRP970529B1 (en) * | 1997-10-02 | 2003-06-30 | Pliva Pharm & Chem Works | Novel hydroxy and polyhydroxy derivatives of cumarin, preparation thereof and antiviral action thereof |
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2000
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