NO328699B1 - Nye forbindelser, sammensetninger inneholdende nevnte forbindelser, samt anvendelse derav som inhibitorer av katekol-O-metyltransferase (COMT) enzymet - Google Patents
Nye forbindelser, sammensetninger inneholdende nevnte forbindelser, samt anvendelse derav som inhibitorer av katekol-O-metyltransferase (COMT) enzymet Download PDFInfo
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- NO328699B1 NO328699B1 NO20026095A NO20026095A NO328699B1 NO 328699 B1 NO328699 B1 NO 328699B1 NO 20026095 A NO20026095 A NO 20026095A NO 20026095 A NO20026095 A NO 20026095A NO 328699 B1 NO328699 B1 NO 328699B1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 108020002739 Catechol O-methyltransferase Proteins 0.000 title abstract description 17
- 239000000203 mixture Substances 0.000 title description 18
- 102000006378 Catechol O-methyltransferase Human genes 0.000 title description 16
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- 108090000790 Enzymes Proteins 0.000 title description 4
- 239000003112 inhibitor Substances 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
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- 238000001727 in vivo Methods 0.000 claims description 7
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- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
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- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 238000001356 surgical procedure Methods 0.000 claims 1
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- 238000011978 dissolution method Methods 0.000 description 1
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- NAOHMNNTUFFTBF-UHFFFAOYSA-N ethyl 2-(2h-tetrazol-5-yl)acetate Chemical compound CCOC(=O)CC=1N=NNN=1 NAOHMNNTUFFTBF-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
- CMWAWVMXRVRPFX-UHFFFAOYSA-N ethyl 6,7-dihydroxy-2-iminochromene-3-carboxylate Chemical compound OC1=C(O)C=C2OC(=N)C(C(=O)OCC)=CC2=C1 CMWAWVMXRVRPFX-UHFFFAOYSA-N 0.000 description 1
- JXAIAZYGEYXKGM-UHFFFAOYSA-N ethyl 7,8-dimethoxy-6-nitro-2-oxochromene-3-carboxylate Chemical compound [O-][N+](=O)C1=C(OC)C(OC)=C2OC(=O)C(C(=O)OCC)=CC2=C1 JXAIAZYGEYXKGM-UHFFFAOYSA-N 0.000 description 1
- LFPNYZFIEJHSMC-UHFFFAOYSA-N ethyl 7-hydroxy-6-methoxy-2-oxochromene-3-carboxylate Chemical compound COC1=C(O)C=C2OC(=O)C(C(=O)OCC)=CC2=C1 LFPNYZFIEJHSMC-UHFFFAOYSA-N 0.000 description 1
- NSEBATSRASFYRC-UHFFFAOYSA-N ethyl 7-hydroxy-6-methoxy-8-nitro-2-oxochromene-3-carboxylate Chemical compound COC1=C(O)C([N+]([O-])=O)=C2OC(=O)C(C(=O)OCC)=CC2=C1 NSEBATSRASFYRC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 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
- 229910001506 inorganic fluoride Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 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
- 229960004502 levodopa Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000006492 vascular dysfunction Effects 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Medicines Containing Plant Substances (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20001593A FI20001593A (fi) | 2000-07-03 | 2000-07-03 | Comt-entsyymiõ inhiboivaa aktiivisuutta omaavia kumariinijohdannaisia |
| PCT/FI2001/000613 WO2002002548A1 (en) | 2000-07-03 | 2001-06-28 | Coumarin derivatives with comt inhibiting activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20026095D0 NO20026095D0 (no) | 2002-12-18 |
| NO20026095L NO20026095L (no) | 2003-03-03 |
| NO328699B1 true NO328699B1 (no) | 2010-04-26 |
Family
ID=8558717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20026095A NO328699B1 (no) | 2000-07-03 | 2002-12-18 | Nye forbindelser, sammensetninger inneholdende nevnte forbindelser, samt anvendelse derav som inhibitorer av katekol-O-metyltransferase (COMT) enzymet |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6951870B2 (ru) |
| EP (1) | EP1301503B1 (ru) |
| JP (1) | JP4851051B2 (ru) |
| KR (1) | KR20030040225A (ru) |
| CN (1) | CN1199963C (ru) |
| AT (1) | ATE260268T1 (ru) |
| AU (2) | AU2001272597B9 (ru) |
| BG (1) | BG107513A (ru) |
| BR (1) | BR0111969A (ru) |
| CA (1) | CA2414787C (ru) |
| DE (1) | DE60102161T2 (ru) |
| DK (1) | DK1301503T3 (ru) |
| EE (1) | EE200300008A (ru) |
| ES (1) | ES2215919T3 (ru) |
| FI (1) | FI20001593A (ru) |
| HU (1) | HUP0301706A3 (ru) |
| IL (2) | IL153352A0 (ru) |
| MX (1) | MXPA02012657A (ru) |
| NO (1) | NO328699B1 (ru) |
| NZ (1) | NZ523121A (ru) |
| PL (1) | PL359068A1 (ru) |
| PT (1) | PT1301503E (ru) |
| RU (1) | RU2282627C2 (ru) |
| SK (1) | SK18452002A3 (ru) |
| TR (1) | TR200400802T4 (ru) |
| WO (1) | WO2002002548A1 (ru) |
| ZA (1) | ZA200210161B (ru) |
Families Citing this family (15)
| 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 |
| AU2002951833A0 (en) * | 2002-10-02 | 2002-10-24 | Novogen Research Pty Ltd | Compositions and therapeutic methods invloving platinum complexes |
| AU2003265737B2 (en) * | 2002-10-02 | 2008-10-16 | Novogen Research Pty Ltd | Combination chemotherapy compositions and methods |
| 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 |
| US8080675B2 (en) | 2004-09-21 | 2011-12-20 | Marshall Edwards, Inc. | Chroman derivatives, medicaments and use in therapy |
| ATE532777T1 (de) | 2004-09-21 | 2011-11-15 | Marshall Edwards Inc | Substituierte chromanderivate, medikamente und anwendungen in der therapie |
| MY148644A (en) * | 2005-07-18 | 2013-05-15 | Orion Corp | New pharmaceutical compounds |
| WO2007022946A1 (de) | 2005-08-21 | 2007-03-01 | 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 |
| 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. |
| EP2635121B1 (en) | 2010-11-01 | 2020-01-08 | MEI Pharma, Inc. | Isoflavonoid compounds and methods for the treatment of cancer |
| 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 |
| PL3253208T3 (pl) | 2015-02-02 | 2021-11-08 | Mei Pharma, Inc. | Terapie kombinowane do zastosowania w leczeniu nowotworu piersi |
| CN108698984B (zh) | 2015-12-18 | 2022-05-10 | H·科斯特 | 用作药物、特别是用于治疗帕金森氏病的双环化合物 |
| 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5035393A (ru) * | 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 |
| 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 |
-
2000
- 2000-07-03 FI FI20001593A patent/FI20001593A/fi unknown
-
2001
- 2001-06-28 EE EEP200300008A patent/EE200300008A/xx unknown
- 2001-06-28 JP JP2002507800A patent/JP4851051B2/ja not_active Expired - Fee Related
- 2001-06-28 KR KR1020027017767A patent/KR20030040225A/ko not_active Application Discontinuation
- 2001-06-28 HU HU0301706A patent/HUP0301706A3/hu unknown
- 2001-06-28 SK SK1845-2002A patent/SK18452002A3/sk unknown
- 2001-06-28 AU AU2001272597A patent/AU2001272597B9/en not_active Ceased
- 2001-06-28 CA CA2414787A patent/CA2414787C/en not_active Expired - Fee Related
- 2001-06-28 NZ NZ523121A patent/NZ523121A/en not_active IP Right Cessation
- 2001-06-28 PT PT01951741T patent/PT1301503E/pt unknown
- 2001-06-28 DK DK01951741T patent/DK1301503T3/da active
- 2001-06-28 US US10/312,817 patent/US6951870B2/en not_active Expired - Fee Related
- 2001-06-28 CN CNB018121934A patent/CN1199963C/zh not_active Expired - Fee Related
- 2001-06-28 BR BR0111969-9A patent/BR0111969A/pt not_active IP Right Cessation
- 2001-06-28 EP EP01951741A patent/EP1301503B1/en not_active Expired - Lifetime
- 2001-06-28 AT AT01951741T patent/ATE260268T1/de active
- 2001-06-28 DE DE60102161T patent/DE60102161T2/de not_active Expired - Lifetime
- 2001-06-28 TR TR2004/00802T patent/TR200400802T4/xx unknown
- 2001-06-28 PL PL01359068A patent/PL359068A1/xx not_active Application Discontinuation
- 2001-06-28 MX MXPA02012657A patent/MXPA02012657A/es active IP Right Grant
- 2001-06-28 ES ES01951741T patent/ES2215919T3/es not_active Expired - Lifetime
- 2001-06-28 IL IL15335201A patent/IL153352A0/xx unknown
- 2001-06-28 WO PCT/FI2001/000613 patent/WO2002002548A1/en active IP Right Grant
- 2001-06-28 AU AU7259701A patent/AU7259701A/xx active Pending
- 2001-06-28 RU RU2003102894/04A patent/RU2282627C2/ru not_active IP Right Cessation
-
2002
- 2002-12-10 IL IL153352A patent/IL153352A/en not_active IP Right Cessation
- 2002-12-13 ZA ZA200210161A patent/ZA200210161B/en unknown
- 2002-12-18 NO NO20026095A patent/NO328699B1/no not_active IP Right Cessation
-
2003
- 2003-01-31 BG BG107513A patent/BG107513A/bg unknown
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| MM1K | Lapsed by not paying the annual fees |