CA2251991C - Alkyl-4-silyl-phenols and esters thereof as antiatherosclerotic agents - Google Patents
Alkyl-4-silyl-phenols and esters thereof as antiatherosclerotic agents Download PDFInfo
- Publication number
- CA2251991C CA2251991C CA002251991A CA2251991A CA2251991C CA 2251991 C CA2251991 C CA 2251991C CA 002251991 A CA002251991 A CA 002251991A CA 2251991 A CA2251991 A CA 2251991A CA 2251991 C CA2251991 C CA 2251991C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- phenol
- butyl
- methyloxy
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 230000000879 anti-atherosclerotic effect Effects 0.000 title claims description 9
- 150000002148 esters Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 202
- -1 hydroxy, methoxy, ethoxy Chemical group 0.000 claims abstract description 107
- 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 claims abstract description 70
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 claims abstract description 51
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 claims abstract description 51
- 230000014509 gene expression Effects 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 25
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 claims abstract description 25
- 102000015271 Intercellular Adhesion Molecule-1 Human genes 0.000 claims abstract description 25
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 102000004127 Cytokines Human genes 0.000 claims abstract description 14
- 108090000695 Cytokines Proteins 0.000 claims abstract description 14
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 14
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 10
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 10
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 8
- 238000005502 peroxidation Methods 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 144
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- HXIGAGXVWIFWDN-UHFFFAOYSA-N 2-tert-butyl-4-[[dimethyl(phenyl)silyl]methoxy]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=CC=CC=2)=C1 HXIGAGXVWIFWDN-UHFFFAOYSA-N 0.000 claims description 4
- 238000008214 LDL Cholesterol Methods 0.000 claims description 4
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 230000006020 chronic inflammation Effects 0.000 claims description 4
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 3
- GCKFMZQFZPUPJV-UHFFFAOYSA-N 4-[[dimethyl(phenyl)silyl]methoxy]-2,3,5-trimethylphenol Chemical compound CC1=CC(O)=C(C)C(C)=C1OC[Si](C)(C)C1=CC=CC=C1 GCKFMZQFZPUPJV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- HTUAUFIWJUMFOE-UHFFFAOYSA-N butanedioic acid;2,6-ditert-butyl-4-(trimethylsilylmethylsulfanyl)phenol Chemical compound OC(=O)CCC(O)=O.CC(C)(C)C1=CC(SC[Si](C)(C)C)=CC(C(C)(C)C)=C1O HTUAUFIWJUMFOE-UHFFFAOYSA-N 0.000 claims description 3
- LUDQZZOBGAUKQC-UHFFFAOYSA-N butanedioic acid;2,6-ditert-butyl-4-[[dimethyl(phenyl)silyl]methoxy]phenol Chemical compound OC(=O)CCC(O)=O.CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=CC=CC=2)=C1 LUDQZZOBGAUKQC-UHFFFAOYSA-N 0.000 claims description 3
- OVAGRPMJPLBNQI-UHFFFAOYSA-N butanedioic acid;2-tert-butyl-4-[[dimethyl(phenyl)silyl]methoxy]phenol Chemical compound OC(=O)CCC(O)=O.C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=CC=CC=2)=C1 OVAGRPMJPLBNQI-UHFFFAOYSA-N 0.000 claims description 3
- ZMJRWWKRZNFRGQ-UHFFFAOYSA-N 2,5-ditert-butyl-4-[[dimethyl(phenyl)silyl]methoxy]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=CC=CC=2)=C1C(C)(C)C ZMJRWWKRZNFRGQ-UHFFFAOYSA-N 0.000 claims description 2
- RIICOPAJNTVLAM-UHFFFAOYSA-N 2,6-ditert-butyl-4-[[dimethyl-[4-(trifluoromethyl)phenyl]silyl]methoxy]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=CC(=CC=2)C(F)(F)F)=C1 RIICOPAJNTVLAM-UHFFFAOYSA-N 0.000 claims description 2
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 claims description 2
- FSQIGEJCTBDCBK-UHFFFAOYSA-N 2-tert-butyl-4-[[dimethyl(phenyl)silyl]methylsulfanyl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(SC[Si](C)(C)C=2C=CC=CC=2)=C1 FSQIGEJCTBDCBK-UHFFFAOYSA-N 0.000 claims description 2
- NITGWAPUTQFYRC-UHFFFAOYSA-N 4-[[benzyl(dimethyl)silyl]methoxy]-2-tert-butylphenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)CC=2C=CC=CC=2)=C1 NITGWAPUTQFYRC-UHFFFAOYSA-N 0.000 claims description 2
- POVWSFOZQKXMAD-UHFFFAOYSA-N acetic acid;2-tert-butyl-4-[[dimethyl(phenyl)silyl]methoxy]phenol Chemical compound CC(O)=O.C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=CC=CC=2)=C1 POVWSFOZQKXMAD-UHFFFAOYSA-N 0.000 claims description 2
- CYWHLPAWWSEOQM-UHFFFAOYSA-N acetic acid;4-[[dimethyl(phenyl)silyl]methoxy]-2,3,6-trimethylphenol Chemical compound CC(O)=O.CC1=C(O)C(C)=CC(OC[Si](C)(C)C=2C=CC=CC=2)=C1C CYWHLPAWWSEOQM-UHFFFAOYSA-N 0.000 claims description 2
- HQVIRBJFKWKPPK-UHFFFAOYSA-N butanedioic acid;2,6-ditert-butyl-4-[[dimethyl(phenyl)silyl]methylsulfanyl]phenol Chemical compound OC(=O)CCC(O)=O.CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(SC[Si](C)(C)C=2C=CC=CC=2)=C1 HQVIRBJFKWKPPK-UHFFFAOYSA-N 0.000 claims description 2
- 230000005747 tumor angiogenesis Effects 0.000 claims description 2
- CZHOOTVWJKWDAK-UHFFFAOYSA-N 4-(benzhydrylsilylmethoxy)-2,6-ditert-butylphenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(OC[SiH2]C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 CZHOOTVWJKWDAK-UHFFFAOYSA-N 0.000 claims 2
- LTERTWMSLJHISJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-[[dimethyl-[3-(trifluoromethyl)phenyl]silyl]methoxy]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=C(C=CC=2)C(F)(F)F)=C1 LTERTWMSLJHISJ-UHFFFAOYSA-N 0.000 claims 1
- RSJJXPGMBGBHBV-UHFFFAOYSA-N 2-tert-butyl-4-[[(4-methoxyphenyl)-dimethylsilyl]methoxy]phenol Chemical compound C1=CC(OC)=CC=C1[Si](C)(C)COC1=CC=C(O)C(C(C)(C)C)=C1 RSJJXPGMBGBHBV-UHFFFAOYSA-N 0.000 claims 1
- FMJCNQNHDMSLOS-UHFFFAOYSA-N 4-(benzhydrylsilylmethoxy)-2,5-ditert-butylphenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(OC[SiH2]C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C(C)(C)C FMJCNQNHDMSLOS-UHFFFAOYSA-N 0.000 claims 1
- NNSSCZGSOCSUQL-UHFFFAOYSA-N acetic acid;2,5-ditert-butyl-4-[[dimethyl(phenyl)silyl]methoxy]phenol Chemical compound CC(O)=O.C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=CC=CC=2)=C1C(C)(C)C NNSSCZGSOCSUQL-UHFFFAOYSA-N 0.000 claims 1
- JZFFZWJALJWXOK-UHFFFAOYSA-N acetic acid;2,6-ditert-butyl-4-[[dimethyl(phenyl)silyl]methoxy]phenol Chemical compound CC(O)=O.CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(OC[Si](C)(C)C=2C=CC=CC=2)=C1 JZFFZWJALJWXOK-UHFFFAOYSA-N 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 abstract description 17
- 239000000126 substance Substances 0.000 abstract description 5
- 230000006866 deterioration Effects 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 2
- 239000000654 additive Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 117
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- 210000002966 serum Anatomy 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 239000000203 mixture Substances 0.000 description 62
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000003921 oil Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 46
- 210000004185 liver Anatomy 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000000034 method Methods 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- 239000010410 layer Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 241000283973 Oryctolagus cuniculus Species 0.000 description 22
- 239000000524 Thiobarbituric Acid Reactive Substance Substances 0.000 description 22
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 18
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- 108010007622 LDL Lipoproteins Proteins 0.000 description 16
- 102000007330 LDL Lipoproteins Human genes 0.000 description 16
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
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- 235000005911 diet Nutrition 0.000 description 12
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 12
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 12
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Classifications
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- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/637,968 US5608095A (en) | 1996-04-30 | 1996-04-30 | Alkyl-4-silyl-phenols and esters thereof as antiatherosclerotic agents |
| US08/637,968 | 1996-04-30 | ||
| PCT/US1997/003335 WO1997041129A1 (en) | 1996-04-30 | 1997-03-03 | Alkyl-4-silyl-phenols and esters thereof as antiatherosclerotic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2251991A1 CA2251991A1 (en) | 1997-11-06 |
| CA2251991C true CA2251991C (en) | 2002-05-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002251991A Expired - Fee Related CA2251991C (en) | 1996-04-30 | 1997-03-03 | Alkyl-4-silyl-phenols and esters thereof as antiatherosclerotic agents |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5608095A (enExample) |
| EP (1) | EP0900225B1 (enExample) |
| JP (1) | JP4309473B2 (enExample) |
| KR (1) | KR100503181B1 (enExample) |
| CN (1) | CN1216993A (enExample) |
| AR (1) | AR006890A1 (enExample) |
| AT (1) | ATE212639T1 (enExample) |
| AU (1) | AU711322B2 (enExample) |
| BR (1) | BR9709190A (enExample) |
| CA (1) | CA2251991C (enExample) |
| DE (1) | DE69710191T2 (enExample) |
| DK (1) | DK0900225T3 (enExample) |
| ES (1) | ES2167716T3 (enExample) |
| IL (1) | IL126758A0 (enExample) |
| NO (1) | NO985039L (enExample) |
| PT (1) | PT900225E (enExample) |
| TW (1) | TW474940B (enExample) |
| WO (1) | WO1997041129A1 (enExample) |
| ZA (1) | ZA973503B (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2209097A (en) * | 1996-04-30 | 1997-11-19 | Hoechst Marion Roussel, Inc. | Method of inhibiting vascular cell adhesion molecule-1 and treating chronic inflammatory diseases with 2,6-di-alkyl-4-silyl-phenols |
| DE69829966T2 (de) * | 1997-05-14 | 2006-02-09 | Atherogenics, Inc. | Ein monoether von probucol und methoden zur hemmung der vcam-1 expression |
| US6670398B2 (en) | 1997-05-14 | 2003-12-30 | Atherogenics, Inc. | Compounds and methods for treating transplant rejection |
| 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 |
| WO1998058937A1 (en) * | 1997-06-25 | 1998-12-30 | Hoechst Marion Roussel, Inc. | 2,6-DI-t-BUTYL-4-[ (DIMETHYL-4-METHOXYPHENYLSILYL) -METHYLOXY]PHENOL AND 2,6-DI-t-BUTYL-4-[ (DIMETHYL-2-METHOXY-PHENYLSILYL) -METHYLOXY]PHENOL |
| JP2002511878A (ja) * | 1997-07-01 | 2002-04-16 | アセロジエニクス・インコーポレイテツド | 抗酸化剤による過増殖状態の治療の増強 |
| CA2350316A1 (en) * | 1998-11-09 | 2000-05-18 | Atherogenics, Inc. | Methods and compositions to lower plasma cholesterol levels |
| US6887712B1 (en) | 1998-11-09 | 2005-05-03 | Atherogenics, Inc. | Methods and compositions to lower plasma cholesterol levels |
| US6020383A (en) * | 1999-01-11 | 2000-02-01 | Eastman Chemicals Company | Method for reducing blood cholesterol and/or blood triglycerides |
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-
1996
- 1996-04-30 US US08/637,968 patent/US5608095A/en not_active Expired - Fee Related
-
1997
- 1997-03-03 KR KR1019980708692A patent/KR100503181B1/ko not_active Expired - Fee Related
- 1997-03-03 AT AT97907998T patent/ATE212639T1/de not_active IP Right Cessation
- 1997-03-03 PT PT97907998T patent/PT900225E/pt unknown
- 1997-03-03 CN CN97194267A patent/CN1216993A/zh active Pending
- 1997-03-03 DE DE69710191T patent/DE69710191T2/de not_active Expired - Fee Related
- 1997-03-03 WO PCT/US1997/003335 patent/WO1997041129A1/en not_active Ceased
- 1997-03-03 DK DK97907998T patent/DK0900225T3/da active
- 1997-03-03 AU AU19854/97A patent/AU711322B2/en not_active Ceased
- 1997-03-03 EP EP97907998A patent/EP0900225B1/en not_active Expired - Lifetime
- 1997-03-03 JP JP53886297A patent/JP4309473B2/ja not_active Expired - Fee Related
- 1997-03-03 BR BR9709190A patent/BR9709190A/pt active Search and Examination
- 1997-03-03 IL IL12675897A patent/IL126758A0/xx unknown
- 1997-03-03 ES ES97907998T patent/ES2167716T3/es not_active Expired - Lifetime
- 1997-03-03 CA CA002251991A patent/CA2251991C/en not_active Expired - Fee Related
- 1997-04-23 TW TW086105269A patent/TW474940B/zh active
- 1997-04-23 ZA ZA9703503A patent/ZA973503B/xx unknown
- 1997-04-29 AR ARP970101749A patent/AR006890A1/es unknown
-
1998
- 1998-10-29 NO NO985039A patent/NO985039L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE212639T1 (de) | 2002-02-15 |
| KR100503181B1 (ko) | 2006-03-03 |
| TW474940B (en) | 2002-02-01 |
| DE69710191T2 (de) | 2002-07-25 |
| JP4309473B2 (ja) | 2009-08-05 |
| CA2251991A1 (en) | 1997-11-06 |
| AR006890A1 (es) | 1999-09-29 |
| BR9709190A (pt) | 1999-08-10 |
| IL126758A0 (en) | 1999-08-17 |
| CN1216993A (zh) | 1999-05-19 |
| KR20000065101A (ko) | 2000-11-06 |
| JP2001509782A (ja) | 2001-07-24 |
| ZA973503B (en) | 1997-10-30 |
| NO985039L (no) | 1998-12-21 |
| US5608095A (en) | 1997-03-04 |
| ES2167716T3 (es) | 2002-05-16 |
| EP0900225A1 (en) | 1999-03-10 |
| DK0900225T3 (da) | 2002-05-13 |
| EP0900225B1 (en) | 2002-01-30 |
| PT900225E (pt) | 2002-06-28 |
| AU1985497A (en) | 1997-11-19 |
| AU711322B2 (en) | 1999-10-14 |
| NO985039D0 (no) | 1998-10-29 |
| DE69710191D1 (de) | 2002-03-14 |
| WO1997041129A1 (en) | 1997-11-06 |
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