KR920002616A - 아테롬성 동맥경화증 치료제로서의 비스[4-(2,6-디-알킬)페놀]실란 유도체 - Google Patents
아테롬성 동맥경화증 치료제로서의 비스[4-(2,6-디-알킬)페놀]실란 유도체 Download PDFInfo
- Publication number
- KR920002616A KR920002616A KR1019910011223A KR910011223A KR920002616A KR 920002616 A KR920002616 A KR 920002616A KR 1019910011223 A KR1019910011223 A KR 1019910011223A KR 910011223 A KR910011223 A KR 910011223A KR 920002616 A KR920002616 A KR 920002616A
- Authority
- KR
- South Korea
- Prior art keywords
- bis
- compound
- phenol
- reacting
- formula
- Prior art date
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- 201000001320 Atherosclerosis Diseases 0.000 title claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title 1
- 150000004756 silanes Chemical class 0.000 title 1
- 230000003859 lipid peroxidation Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 15
- -1 methylenethio Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- JZZIHCLFHIXETF-UHFFFAOYSA-N dimethylsilicon Chemical group C[Si]C JZZIHCLFHIXETF-UHFFFAOYSA-N 0.000 claims 4
- 229910052749 magnesium Inorganic materials 0.000 claims 4
- 239000011777 magnesium Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 239000000010 aprotic solvent Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- 150000002009 diols Chemical class 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/32—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Materials Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fats And Perfumes (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (24)
- 하기 일반식(Ⅰ)의 화합물 :
-
- 상기식에서, R1,R2,R3및R4는 각각 독립적으로 C1-6알킬그룹이고; Z는 티오, 옥시 또는 메틸렌그룹이며; A는 C1-4알킬렌그룹이다.
- 제1항에 있어서, R1및 R2가 3급-부틸인 화합물.
- 제2항에 있어서, A가 메틸렌인 화합물.
- 제3항에 있어서, Z가 티오인 화합물.
- 제3항에 있어서, Z가 옥시인 화합물.
- 제3항에 있어서, Z가 메틸렌인 화합물.
- 제1항에 있어서, 4,4'-〔(디메틸실릴렌)비스(메틸렌티오)〕-비스〔2,6-디-3급-부틸〕페놀인 화합물.
- 제1항에 있어서, 4,4'-〔(디메틸실릴렌)비스(메틸렌티오)〕-비스〔2,6-디메틸〕페놀인 화합물.
- 제1항에 있어서, 4,4'-〔(디메틸실릴렌)디-2,1-에탄디일〕비스〔2,6-디메틸〕페놀인 화합물.
- 제1항에 있어서, 4,4'-〔(디메틸실릴렌)디-2,1-에탄디일〕비스〔2,6-디에틸〕페놀인 화합물.
- 아테롬성 동맥경화증 치료적 유효량의 제1항에 따른 화합물을 이를 필요로 하는 환자에게 투여하여 아테롬성 동맥경화증 환자의 아테롬성 동맥경화증 진행을 억제하는 방법.
- 산화방지적 유효량의 제1항에 따른 화합물을 이를 필요로 하는 환자에 투여하여 상기 환자에게서의 LDL지질과산화를 억제하는 방법.
- 하기 일반식(2)의 화합물을 적합한 비양자성 용매중에서 비-친핵성 염기 및 적절한 비스-할로알킬렌실란 0.5당량과 반응시켜 하기 일반식(1a)의 화합물을 제조하는 방법 :
-
- 상기식에서, R1,R2,R3및R4는 각각 독립적으로 C1-6알킬 그룹이고; Z'는 티오 또는 옥시그룹이며; A는 C1-4알킬렌 그룹이다.
- (a)적절한 비스-할로알킬실란을 적합한 비양자성 용매중에서 마그네슘 금속과 반응시켜 비스(마그네슘 할로겐화물)염을 형성시키고; (b)비스(마그네슘 할로겐화물)염을 적절한 3,5-디알킬-4-하이드록시-벤즈알데하이드 2당량과 반응시켜 상응하는 디올을 형성시키며; (c)디올을 환원시키는 단계들을 포함하여 하기 일반식(1b)의 화합물을 제조하는 방법 :
-
- 상기식에서, R1,R2,R3및R4는 각각 독립적으로 C1-6알킬그룹이고; A는 C1-6알킬렌 그룹이다.
- (a)적절한 비스-할로알킬실란을 적합한 비양자성 용매중에서 마그네슘 금속과 반응시켜 비스(마그네슘 할로겐화물)염을 형성시키고; (b)비스(마그네슘 할로겐화물)염을 적절한 3,5-디알킬-4-하이드록시-벤질할라이드 2당량과 반응시키는 단계들을 포함하여 하기 일반식(1b)의 화합물을 제조하는 방법 :
-
- 상기식에서, R1,R2,R3및R4는 각각 독립적으로 C1-6알킬그룹이고; A는 C1-4알킬렌 그룹이다.
- ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US54805190A | 1990-07-05 | 1990-07-05 | |
US548,051 | 1990-07-05 | ||
US07/548,051 | 1990-07-05 | ||
US69668491A | 1991-05-07 | 1991-05-07 | |
US696684 | 1991-05-07 | ||
US696,684 | 1991-05-07 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR920002616A true KR920002616A (ko) | 1992-02-28 |
KR0186006B1 KR0186006B1 (ko) | 1999-05-15 |
Family
ID=27068750
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910011223A KR0186006B1 (ko) | 1990-07-05 | 1991-07-03 | 비스(4-(2,6-디-알킬)페놀)실란 유도체, 이의 제조방법 및 이를 포함하는 약제학적 조성물 |
Country Status (20)
Country | Link |
---|---|
US (1) | US5281738A (ko) |
EP (1) | EP0464844B1 (ko) |
JP (1) | JP2963557B2 (ko) |
KR (1) | KR0186006B1 (ko) |
CN (1) | CN1029614C (ko) |
AT (1) | ATE132154T1 (ko) |
AU (1) | AU639807B2 (ko) |
CA (1) | CA2046050C (ko) |
DE (1) | DE69115771T2 (ko) |
DK (1) | DK0464844T3 (ko) |
ES (1) | ES2084062T3 (ko) |
FI (1) | FI101704B (ko) |
GR (1) | GR3018926T3 (ko) |
HU (1) | HU210695B (ko) |
IE (1) | IE72155B1 (ko) |
IL (1) | IL98711A (ko) |
NO (1) | NO179914C (ko) |
NZ (1) | NZ238807A (ko) |
PT (1) | PT98219B (ko) |
TW (1) | TW213919B (ko) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2707989B1 (fr) * | 1993-07-22 | 1995-10-13 | Pf Medicament | Nouveaux dérivés de benzylamines silylées, leurs sels, leurs procédés de fabrication et les compositions pharmaceutiques les renfermant. |
US5677291A (en) * | 1993-12-10 | 1997-10-14 | Hoechst Marion Roussel, Inc. | Method of lowering serum cholesterol levels with 2,6-di-alkyl-4-silyl-phenols |
AU681731B2 (en) * | 1993-12-10 | 1997-09-04 | Aventis Inc. | Method of lowering serum cholesterol levels with 2,6-di-alkyl-4-silyl-phenols |
US5449679A (en) * | 1994-07-29 | 1995-09-12 | Leonard; Robert J. | Process and products for reducing biological fluid levels of a lipid soluble waste |
US5608095A (en) * | 1996-04-30 | 1997-03-04 | Hoechst Marion Roussel, Inc. | Alkyl-4-silyl-phenols and esters thereof as antiatherosclerotic agents |
US5795876A (en) * | 1996-04-30 | 1998-08-18 | Hoechst Marion Rousssel, Inc. | Method of inhibiting vascular cell adhesion molecule-1 and treating chronic inflammatory diseases with 2, 6-di-alkyl-4-silyl-phenols |
US6114572A (en) * | 1996-11-20 | 2000-09-05 | Hoechst Marion Roussel, Inc. | Substituted phenols and thiophenols useful as antioxidant agents |
US6121463A (en) * | 1997-06-24 | 2000-09-19 | Hoechst Marion Roussel, Inc. | Alkyl-4-silylheterocyclic phenols and thiophenols useful as antioxidant agents |
US6133467A (en) * | 1997-06-25 | 2000-10-17 | Hoechst Marion Roussel, Inc. | 2,6-di-t-butyl-4-[(dimethyl-4-methoxyphenylsilyl)-methyl-oxy]phenol and 2,6-di-t-butyl-4-[(dimethyl-2-methoxy-phenylsilyl)methyloxy]phenol |
AUPO787897A0 (en) * | 1997-07-14 | 1997-08-07 | Cardiac Crc Nominees Pty Limited | Silicon-containing chain extenders |
US9000472B2 (en) * | 2011-12-30 | 2015-04-07 | Dow Corning Corporation | Optical assembly and method of forming an optical assembly |
CN104817581B (zh) * | 2015-05-07 | 2018-01-02 | 衢州学院 | 一种含硅二元酚及其制备方法 |
JP2023516912A (ja) * | 2020-02-24 | 2023-04-21 | ダウ グローバル テクノロジーズ エルエルシー | 金属-配位子錯体触媒のヘテロ原子架橋前駆体の非極低温合成 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3506674A (en) * | 1967-07-03 | 1970-04-14 | Gen Electric | Certain pyridyl thio ether silanes |
US3853776A (en) * | 1972-09-29 | 1974-12-10 | Monsanto Co | Low pour point fluids and blends containing same |
US3801617A (en) * | 1973-07-24 | 1974-04-02 | Nasa | Thiophenyl ether disiloxanes and trisiloxanes useful as lubricant fluids |
AR208203A1 (es) * | 1974-09-10 | 1976-12-09 | Cortial | Proceso para la preparacion de acido p-trialquilsilil benzoico y derivados del mismo |
JPS61263988A (ja) * | 1985-05-16 | 1986-11-21 | Shionogi & Co Ltd | シリル置換エ−テル類および殺虫・殺ダニ剤 |
US4636573A (en) * | 1985-09-09 | 1987-01-13 | Pastor Stephen D | Hindered silicon ester stabilizers |
US4804653A (en) * | 1986-05-02 | 1989-02-14 | Uniroyal Chemical Company, Inc. | Thiomethyl-substituted organosilane compounds and their use as pesticides |
US4783495A (en) * | 1987-11-20 | 1988-11-08 | Ciba-Geigy Corporation | (Hydroxyphenyl) silane stabilizers |
US5155250A (en) * | 1990-07-05 | 1992-10-13 | Merrell Dow Pharmaceuticals Inc. | 2,6-di-alkyl-4-silyl-phenols as antiatheroscerotic agents |
DE4031001A1 (de) * | 1990-10-01 | 1992-04-02 | Hoechst Ag | Verfahren zur herstellung von 4-ethoxyphenyl-3-arylpropyl-(dimethyl)silanen |
-
1991
- 1991-07-01 NZ NZ238807A patent/NZ238807A/en unknown
- 1991-07-02 IL IL9871191A patent/IL98711A/en not_active IP Right Cessation
- 1991-07-02 TW TW080105145A patent/TW213919B/zh active
- 1991-07-02 CA CA002046050A patent/CA2046050C/en not_active Expired - Lifetime
- 1991-07-03 AU AU80114/91A patent/AU639807B2/en not_active Ceased
- 1991-07-03 KR KR1019910011223A patent/KR0186006B1/ko not_active IP Right Cessation
- 1991-07-04 AT AT91111220T patent/ATE132154T1/de not_active IP Right Cessation
- 1991-07-04 HU HU912271A patent/HU210695B/hu not_active IP Right Cessation
- 1991-07-04 FI FI913253A patent/FI101704B/fi active
- 1991-07-04 CN CN91104474A patent/CN1029614C/zh not_active Expired - Fee Related
- 1991-07-04 NO NO912629A patent/NO179914C/no unknown
- 1991-07-04 JP JP3189499A patent/JP2963557B2/ja not_active Expired - Lifetime
- 1991-07-04 DE DE69115771T patent/DE69115771T2/de not_active Expired - Lifetime
- 1991-07-04 ES ES91111220T patent/ES2084062T3/es not_active Expired - Lifetime
- 1991-07-04 IE IE234191A patent/IE72155B1/en not_active IP Right Cessation
- 1991-07-04 PT PT98219A patent/PT98219B/pt not_active IP Right Cessation
- 1991-07-05 DK DK91111220.9T patent/DK0464844T3/da active
- 1991-07-05 EP EP91111220A patent/EP0464844B1/en not_active Expired - Lifetime
-
1992
- 1992-09-02 US US07/939,561 patent/US5281738A/en not_active Expired - Lifetime
-
1996
- 1996-02-07 GR GR960400332T patent/GR3018926T3/el unknown
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