FI95700B - Förfarande för framställning av terapeutiskt användbara kromanderivat - Google Patents
Förfarande för framställning av terapeutiskt användbara kromanderivat Download PDFInfo
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- FI95700B FI95700B FI903863A FI903863A FI95700B FI 95700 B FI95700 B FI 95700B FI 903863 A FI903863 A FI 903863A FI 903863 A FI903863 A FI 903863A FI 95700 B FI95700 B FI 95700B
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- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 14
- 125000003016 chromanyl group Chemical class O1C(CCC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 3
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005479 oxodihydropyridyl group Chemical group 0.000 claims description 3
- HNIREJJTLZILSW-UHFFFAOYSA-N 2-(methoxymethyl)-2-methyl-4-(2-oxopyridin-1-yl)chromene-6-carbonitrile Chemical compound C=1C(COC)(C)OC2=CC=C(C#N)C=C2C=1N1C=CC=CC1=O HNIREJJTLZILSW-UHFFFAOYSA-N 0.000 claims description 2
- DJAXIQDBQLRGMU-UHFFFAOYSA-N 3-hydroxy-2-(methoxymethyl)-2-methyl-4-(2-oxopyridin-1-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound OC1C(COC)(C)OC2=CC=C(C#N)C=C2C1N1C=CC=CC1=O DJAXIQDBQLRGMU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001843 chromanes Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 21
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- -1 isopentyl (3-methylbutyl) Chemical group 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 241000700159 Rattus Species 0.000 description 3
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- 239000013543 active substance Substances 0.000 description 3
- 150000001844 chromium Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 description 3
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- IWAOGOHKIUXSDC-UHFFFAOYSA-N 2-(methoxymethyl)-2-methyl-1a,7b-dihydrooxireno[2,3-c]chromene-6-carbonitrile Chemical compound COCC1(C)OC2=CC=C(C#N)C=C2C2C1O2 IWAOGOHKIUXSDC-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- 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
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (2)
1. Förfarande för framställning av nya, terapeu-tiskt användbara kromanderivat med formeln I 5 L li jLcH5R2 10 °Λι väri R1 är A, R2 är OA,
15 R3 är OH och R4 är H eller R3 och R4 tillsammans betecknar en bindning, R5 är en osubstituerad eller med en A-substituent substituerad oxo-dihydro-pyridylgrupp, och 20 A är en alkyl med 1-6 C-atomer, samt salter därav, kännetecknat av att en kroman med formeln II CN ,/ 25 II UC0^r2 V väri
30 X-Y betecknar -dH-CH- eller -CHE-CHR3- och *·· E betecknar Cl, Br, I eller en reaktiv esteriserad OH-grupp och R1, R2 och R3 betecknar samma som i formeln I, bringas att reagera med en förening med formeln III 35 · · aa.i aie in n 95700 r5-h hi väri R5 har samma betydelse som i formeIn I, 5 och/eller eventuellt föreningen med formeln I, väri R3 är OH och R4 är H, dehydrateras och/eller en eller flera av grupperna R2 och R5 i föreningen med formeln I omvandlas till en annan R2- och/eller R5-grupp och/eller den baslska föreningen med formeln I omvandlas genom behandling med 10 syra till en syraadditionssalt därav.
2. Förfarande enligt patentkrav 1, k ä n n e -tecknat av att a) en 2-metoximetyl-2-metyl-4-(1,2-dihydro-2-oxo- l-pyridyl)-6-cyan-3-kromanol eller 15 b) en 2-metoximetyl-2-metyl-4-(1,2-dihydro-2-oxo- 1-pyridyl)-6-cyan-3-kromen framställs. » · · > · «
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3926001 | 1989-08-05 | ||
| DE3926001A DE3926001A1 (de) | 1989-08-05 | 1989-08-05 | Chromanderivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI903863A0 FI903863A0 (sv) | 1990-08-03 |
| FI95700B true FI95700B (sv) | 1995-11-30 |
| FI95700C FI95700C (sv) | 1996-03-11 |
Family
ID=6386618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI903863A FI95700C (sv) | 1989-08-05 | 1990-08-03 | Förfarande för framställning av terapeutiskt användbara kromanderivat |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5130322A (sv) |
| EP (1) | EP0415065B1 (sv) |
| JP (1) | JPH0366681A (sv) |
| KR (1) | KR910004602A (sv) |
| AR (1) | AR245711A1 (sv) |
| AT (1) | ATE124407T1 (sv) |
| AU (1) | AU623797B2 (sv) |
| DE (2) | DE3926001A1 (sv) |
| DK (1) | DK0415065T3 (sv) |
| ES (1) | ES2073483T3 (sv) |
| FI (1) | FI95700C (sv) |
| HU (1) | HU213391B (sv) |
| IE (1) | IE68313B1 (sv) |
| IL (1) | IL95277A (sv) |
| NO (1) | NO176477C (sv) |
| NZ (1) | NZ234773A (sv) |
| PT (1) | PT94902B (sv) |
| TW (1) | TW209860B (sv) |
| ZA (1) | ZA906144B (sv) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5387587A (en) * | 1986-12-23 | 1995-02-07 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Chroman derivatives |
| US5284838A (en) * | 1987-06-23 | 1994-02-08 | Elf Sanofi | Use of 2,2-dimethylchroman-3-ol derivatives in the treatment of asthma |
| DE4102103A1 (de) * | 1991-01-25 | 1992-08-20 | Bayer Ag | Substituierte benzoxazepine und benzthiazepine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| KR950009862B1 (ko) * | 1991-05-22 | 1995-08-29 | 재단법인한국화학연구소 | 벤조피란 유도체와 그의 제조방법(1) |
| KR950009863B1 (ko) * | 1991-05-22 | 1995-08-29 | 재단법인한국화학연구소 | 벤조피란 유도체와 그의 제조방법 |
| TW257762B (sv) * | 1991-06-14 | 1995-09-21 | Nippon Chemicals Pharmaceutical Co Ltd | |
| US5250547A (en) * | 1991-08-29 | 1993-10-05 | Syntex (U.S.A.) Inc. | Benzopyran derivatives |
| US5719155A (en) * | 1993-11-10 | 1998-02-17 | Japan Tobacco Inc. | Chroman derivative and pharmaceutical use thereof |
| US5470861A (en) * | 1994-08-04 | 1995-11-28 | Hoffmann-La Roche Inc. | Method of promoting hair growth |
| DE19647000A1 (de) * | 1996-11-14 | 1998-05-20 | Hoechst Ag | 3-Amido-chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| JP2001151767A (ja) * | 1999-09-17 | 2001-06-05 | Nissan Chem Ind Ltd | ベンゾピラン誘導体 |
| JP2001158780A (ja) * | 1999-09-24 | 2001-06-12 | Nissan Chem Ind Ltd | ４−オキシベンゾピラン誘導体 |
| JP2001172275A (ja) * | 1999-10-05 | 2001-06-26 | Nissan Chem Ind Ltd | ４−オキシベンゾピラン誘導体 |
| WO2011013987A2 (ko) * | 2009-07-29 | 2011-02-03 | 한국화학연구원 | 2,2-이치환-2h-크로멘 화합물 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3274350D1 (en) * | 1981-09-25 | 1987-01-08 | Beecham Group Plc | Pharmaceutically active benzopyran compounds |
| EP0091748B1 (en) * | 1982-04-08 | 1986-06-18 | Beecham Group Plc | Antihypertensive benzopyranols |
| EP0093534A1 (en) * | 1982-04-28 | 1983-11-09 | Beecham Group Plc | Novel chromanols |
| ATE56007T1 (de) * | 1984-06-22 | 1990-09-15 | Beecham Group Plc | Wirksame benzopyranverbindungen. |
| GB8419516D0 (en) * | 1984-07-31 | 1984-09-05 | Beecham Group Plc | Treatment |
| GB8419515D0 (en) * | 1984-07-31 | 1984-09-05 | Beecham Group Plc | Treatment |
| PT84806B (pt) * | 1986-05-03 | 1989-12-29 | Beecham Group Plc | Processo para a preparacao de benzopiranos |
| DE3726261A1 (de) * | 1986-12-23 | 1988-07-07 | Merck Patent Gmbh | Chromanderivate |
| FR2615191B1 (fr) * | 1987-05-16 | 1991-01-11 | Sandoz Sa | Nouveaux benzo(b)pyrannes et pyrannopyridines, leur preparation et leur utilisation comme medicaments |
| AU618007B2 (en) * | 1987-06-23 | 1991-12-12 | Sanofi | 2,2-dimethylchroman-3-ol derivatives, process for their preparation and pharmaceutical compositions in which they are present |
| FI90343C (sv) * | 1987-06-23 | 1994-01-25 | Merck Patent Gmbh | Förfarande för framställning av antihypertoniska och antiarytmiska trans-2,2-dimetylkroman-3-olderivat |
| US4971982A (en) * | 1987-07-06 | 1990-11-20 | Hoffmann-La Roche Inc. | Benzopyran derivatives |
-
1989
- 1989-08-05 DE DE3926001A patent/DE3926001A1/de not_active Withdrawn
-
1990
- 1990-07-21 DK DK90114008.7T patent/DK0415065T3/da active
- 1990-07-21 ES ES90114008T patent/ES2073483T3/es not_active Expired - Lifetime
- 1990-07-21 AT AT90114008T patent/ATE124407T1/de not_active IP Right Cessation
- 1990-07-21 DE DE59009322T patent/DE59009322D1/de not_active Expired - Fee Related
- 1990-07-21 EP EP90114008A patent/EP0415065B1/de not_active Expired - Lifetime
- 1990-08-02 KR KR1019900011867A patent/KR910004602A/ko not_active Application Discontinuation
- 1990-08-02 TW TW079106412A patent/TW209860B/zh active
- 1990-08-02 AU AU60134/90A patent/AU623797B2/en not_active Ceased
- 1990-08-03 JP JP2205312A patent/JPH0366681A/ja active Pending
- 1990-08-03 FI FI903863A patent/FI95700C/sv not_active IP Right Cessation
- 1990-08-03 IE IE282290A patent/IE68313B1/en not_active IP Right Cessation
- 1990-08-03 AR AR90317525A patent/AR245711A1/es active
- 1990-08-03 US US07/562,542 patent/US5130322A/en not_active Expired - Fee Related
- 1990-08-03 NO NO903431A patent/NO176477C/no unknown
- 1990-08-03 PT PT94902A patent/PT94902B/pt not_active IP Right Cessation
- 1990-08-03 NZ NZ234773A patent/NZ234773A/en unknown
- 1990-08-03 IL IL9527790A patent/IL95277A/en not_active IP Right Cessation
- 1990-08-03 HU HU904889A patent/HU213391B/hu unknown
- 1990-08-03 ZA ZA906144A patent/ZA906144B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU904889D0 (en) | 1991-01-28 |
| IL95277A0 (en) | 1991-06-30 |
| IL95277A (en) | 1995-10-31 |
| DK0415065T3 (da) | 1995-08-28 |
| IE902822A1 (en) | 1991-02-27 |
| FI903863A0 (sv) | 1990-08-03 |
| EP0415065B1 (de) | 1995-06-28 |
| PT94902B (pt) | 1997-06-30 |
| TW209860B (sv) | 1993-07-21 |
| NO176477B (no) | 1995-01-02 |
| ES2073483T3 (es) | 1995-08-16 |
| NO903431D0 (no) | 1990-08-03 |
| IE68313B1 (en) | 1996-06-12 |
| DE59009322D1 (de) | 1995-08-03 |
| AR245711A1 (es) | 1994-02-28 |
| NZ234773A (en) | 1992-10-28 |
| NO903431L (no) | 1991-02-06 |
| ATE124407T1 (de) | 1995-07-15 |
| US5130322A (en) | 1992-07-14 |
| ZA906144B (en) | 1991-05-29 |
| JPH0366681A (ja) | 1991-03-22 |
| AU6013490A (en) | 1991-02-07 |
| EP0415065A1 (de) | 1991-03-06 |
| HUT58713A (en) | 1992-03-30 |
| HU213391B (en) | 1997-06-30 |
| NO176477C (no) | 1995-04-12 |
| PT94902A (pt) | 1991-04-18 |
| DE3926001A1 (de) | 1991-02-07 |
| AU623797B2 (en) | 1992-05-21 |
| KR910004602A (ko) | 1991-03-29 |
| FI95700C (sv) | 1996-03-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: MERCK PATENT GESELLSCHAFT MIT BESCHRAENKTER HAFTUN |