NL8101592A - Cholesterol-biosynthese-remstoffen, hun bereiding en gebruik. - Google Patents
Cholesterol-biosynthese-remstoffen, hun bereiding en gebruik. Download PDFInfo
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- NL8101592A NL8101592A NL8101592A NL8101592A NL8101592A NL 8101592 A NL8101592 A NL 8101592A NL 8101592 A NL8101592 A NL 8101592A NL 8101592 A NL8101592 A NL 8101592A NL 8101592 A NL8101592 A NL 8101592A
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- 238000002360 preparation method Methods 0.000 title claims description 10
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 title abstract description 19
- 230000015572 biosynthetic process Effects 0.000 title abstract description 11
- 235000012000 cholesterol Nutrition 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000002252 acyl group Chemical group 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 238000005917 acylation reaction Methods 0.000 claims abstract description 10
- 230000010933 acylation Effects 0.000 claims abstract description 9
- 241000228347 Monascus <ascomycete fungus> Species 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- WWSNTLOVYSRDEL-UHFFFAOYSA-N desmethylmonacolin J Natural products CC1C=CC2=CCCC(O)C2C1CCC1CC(O)CC(=O)O1 WWSNTLOVYSRDEL-UHFFFAOYSA-N 0.000 claims description 181
- WWSNTLOVYSRDEL-DZSDEGEFSA-N compactin diol lactone Chemical compound C([C@@H]1[C@H]2[C@@H](O)CCC=C2C=C[C@@H]1C)C[C@@H]1C[C@@H](O)CC(=O)O1 WWSNTLOVYSRDEL-DZSDEGEFSA-N 0.000 claims description 179
- LXZBFUBRYYVRQJ-AXHZAXLDSA-M sodium;(3r,5r)-7-[(1s,2s,6r,8s,8ar)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C=C21 LXZBFUBRYYVRQJ-AXHZAXLDSA-M 0.000 claims description 108
- -1 methylenedioxy groups Chemical group 0.000 claims description 90
- 239000007788 liquid Substances 0.000 claims description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 244000005700 microbiome Species 0.000 claims description 18
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 7
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- 241000031003 Monascus ruber Species 0.000 claims description 6
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims description 4
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- 239000000126 substance Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
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- 125000004429 atom Chemical group 0.000 claims 2
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
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- 239000003085 diluting agent Substances 0.000 claims 1
- QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
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- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 114
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 36
- 238000000921 elemental analysis Methods 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
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- 239000011541 reaction mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- 238000004458 analytical method Methods 0.000 description 6
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- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 4
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- JDKQTIKEGOOXTJ-UHFFFAOYSA-N pent-4-enoyl chloride Chemical compound ClC(=O)CCC=C JDKQTIKEGOOXTJ-UHFFFAOYSA-N 0.000 description 3
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- MBIZFBDREVRUHY-UHFFFAOYSA-N 2,6-Dimethoxybenzoic acid Chemical compound COC1=CC=CC(OC)=C1C(O)=O MBIZFBDREVRUHY-UHFFFAOYSA-N 0.000 description 2
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-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55041292A JPH0692381B2 (ja) | 1980-03-31 | 1980-03-31 | Ｍｂ−５３０ａ誘導体 |
| JP4129280 | 1980-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8101592A true NL8101592A (nl) | 1981-10-16 |
Family
ID=12604367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8101592A NL8101592A (nl) | 1980-03-31 | 1981-03-31 | Cholesterol-biosynthese-remstoffen, hun bereiding en gebruik. |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPH0692381B2 (ja) |
| AT (1) | ATA150781A (ja) |
| AU (1) | AU6893281A (ja) |
| BE (1) | BE888214A (ja) |
| CH (1) | CH646966A5 (ja) |
| DE (2) | DE3112566A1 (ja) |
| DK (3) | DK151273C (ja) |
| FI (1) | FI810991L (ja) |
| FR (1) | FR2479222A1 (ja) |
| GB (1) | GB2073193A (ja) |
| IE (1) | IE52367B1 (ja) |
| IT (1) | IT1144325B (ja) |
| MX (1) | MX9203567A (ja) |
| NL (1) | NL8101592A (ja) |
| SE (1) | SE461590B (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472426A (en) * | 1982-12-22 | 1984-09-18 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| DE3682557D1 (de) * | 1985-09-13 | 1992-01-02 | Sankyo Co | Hydroxy-ml-236b-derivate, deren herstellung und anwendung. |
| US4997848A (en) * | 1987-10-27 | 1991-03-05 | Sankyo Company, Limited | Octahydronaphthalene oxime derivatives for cholesterol synthesis inhibition |
| US5075327A (en) * | 1988-08-10 | 1991-12-24 | Hoffmann-La Roche Inc. | Antipsoriatic agents |
| US5021451A (en) * | 1988-11-14 | 1991-06-04 | Hoffman-La Roche Inc. | Method for inhibiting hyperproliferative diseases |
| US5200549A (en) * | 1988-11-14 | 1993-04-06 | Hoffman-La Roche Inc. | Antipsoriatic agents |
| US5073568A (en) * | 1988-11-14 | 1991-12-17 | Hoffmann-La Roche Inc. | Antipsoriatic agents |
| US5159104A (en) * | 1991-05-01 | 1992-10-27 | Merck & Co., Inc. | Process to simvastatin ester |
| FR2937537A1 (fr) * | 2008-10-29 | 2010-04-30 | Centre Nat Rech Scient | Nanoparticules de statine |
| KR101820099B1 (ko) | 2013-01-18 | 2018-01-18 | 에스프린팅솔루션 주식회사 | 저항 발열체, 이를 채용한 가열 부재, 및 정착 장치 |
| RU2020126177A (ru) | 2018-01-09 | 2022-02-10 | Лиганд Фармасьютикалз, Инк. | Ацетальные соединения и их терапевтическое применение |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5612114B2 (ja) * | 1974-06-07 | 1981-03-18 | ||
| JPS5925599B2 (ja) * | 1979-02-20 | 1984-06-19 | 三共株式会社 | 新生理活性物質モナコリンｋおよびその製造法 |
| US4231938A (en) * | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| AU535944B2 (en) * | 1979-06-15 | 1984-04-12 | Merck & Co., Inc. | Hypocholestermic fermentation products from aspergillus |
| PT72394B (en) * | 1980-02-04 | 1982-09-06 | Merck & Co Inc | Process for preparing dihydro and tetrahydromevinoline hypocholesterolimics |
| US4282155A (en) * | 1980-02-04 | 1981-08-04 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| AU548996B2 (en) * | 1980-02-04 | 1986-01-09 | Merck & Co., Inc. | Tetrahydro-2h-pyran-2-one derivatives |
| ZA81703B (en) * | 1980-02-04 | 1982-09-29 | Merck & Co Inc | New antihypercholesterolemic compounds,intermediates and processes |
-
1980
- 1980-03-31 JP JP55041292A patent/JPH0692381B2/ja not_active Expired - Lifetime
-
1981
- 1981-03-27 IE IE698/81A patent/IE52367B1/en not_active IP Right Cessation
- 1981-03-30 DE DE19813112566 patent/DE3112566A1/de active Granted
- 1981-03-30 CH CH215381A patent/CH646966A5/de not_active IP Right Cessation
- 1981-03-30 IT IT67438/81A patent/IT1144325B/it active
- 1981-03-30 DE DE3153666A patent/DE3153666C2/de not_active Expired - Lifetime
- 1981-03-31 BE BE0/204328A patent/BE888214A/fr not_active IP Right Cessation
- 1981-03-31 AT AT0150781A patent/ATA150781A/de not_active IP Right Cessation
- 1981-03-31 FI FI810991A patent/FI810991L/fi not_active Application Discontinuation
- 1981-03-31 GB GB8110075A patent/GB2073193A/en not_active Withdrawn
- 1981-03-31 NL NL8101592A patent/NL8101592A/nl not_active Application Discontinuation
- 1981-03-31 DK DK145481A patent/DK151273C/da not_active IP Right Cessation
- 1981-03-31 FR FR8106403A patent/FR2479222A1/fr active Granted
- 1981-03-31 AU AU68932/81A patent/AU6893281A/en not_active Abandoned
- 1981-03-31 SE SE8102047A patent/SE461590B/sv not_active Application Discontinuation
-
1990
- 1990-02-07 DK DK032290A patent/DK32290A/da not_active Application Discontinuation
- 1990-02-07 DK DK032190A patent/DK167805B1/da not_active IP Right Cessation
-
1992
- 1992-06-26 MX MX9203567A patent/MX9203567A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU6893281A (en) | 1981-10-08 |
| SE8102047L (sv) | 1981-10-01 |
| DK145481A (da) | 1981-10-01 |
| DE3112566A1 (de) | 1982-03-11 |
| IT1144325B (it) | 1986-10-29 |
| BE888214A (fr) | 1981-09-30 |
| ATA150781A (de) | 1983-03-15 |
| DK32290D0 (da) | 1990-02-07 |
| DK32290A (da) | 1990-02-07 |
| DK167805B1 (da) | 1993-12-20 |
| FR2479222B1 (ja) | 1983-08-26 |
| MX9203567A (es) | 1992-09-01 |
| DK32190D0 (da) | 1990-02-07 |
| GB2073193A (en) | 1981-10-14 |
| JPS56138181A (en) | 1981-10-28 |
| FR2479222A1 (fr) | 1981-10-02 |
| CH646966A5 (de) | 1984-12-28 |
| DK32190A (da) | 1990-02-07 |
| SE461590B (sv) | 1990-03-05 |
| DK151273C (da) | 1988-07-04 |
| IT8167438A0 (it) | 1981-03-30 |
| IE810698L (en) | 1981-09-30 |
| DE3153666C2 (de) | 1993-11-11 |
| DK151273B (da) | 1987-11-16 |
| FI810991L (fi) | 1981-10-01 |
| JPH0692381B2 (ja) | 1994-11-16 |
| DE3112566C2 (ja) | 1990-04-05 |
| IE52367B1 (en) | 1987-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BT | A notification was added to the application dossier and made available to the public | ||
| BV | The patent application has lapsed |