JPH04230213A - ある種のビス（３，５−ジ−アルキル−４−ヒドロキシフェニルチオ）メタン類の血中トリグリセリド減少への用途 - Google Patents
ある種のビス（３，５−ジ−アルキル−４−ヒドロキシフェニルチオ）メタン類の血中トリグリセリド減少への用途Info
- Publication number
- JPH04230213A JPH04230213A JP3173445A JP17344591A JPH04230213A JP H04230213 A JPH04230213 A JP H04230213A JP 3173445 A JP3173445 A JP 3173445A JP 17344591 A JP17344591 A JP 17344591A JP H04230213 A JPH04230213 A JP H04230213A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydroxyphenylthio
- bis
- blood
- triglyceride
- 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.)
- Pending
Links
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- 239000008280 blood Substances 0.000 title claims abstract description 14
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title abstract description 13
- 230000009467 reduction Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 238000011282 treatment Methods 0.000 claims abstract description 20
- GAABJUNZYPATIQ-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylmethylsulfanyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(SCSC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GAABJUNZYPATIQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003626 triacylglycerols Chemical class 0.000 claims description 20
- 230000000544 hyperemic effect Effects 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
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- 208000006575 hypertriglyceridemia Diseases 0.000 abstract 1
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- 239000008194 pharmaceutical composition Substances 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- NFVMNXZFSKGLDR-UHFFFAOYSA-N 2,6-ditert-butyl-4-sulfanylphenol Chemical compound CC(C)(C)C1=CC(S)=CC(C(C)(C)C)=C1O NFVMNXZFSKGLDR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 238000005588 Kraus reaction Methods 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
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- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
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- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
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- 210000004324 lymphatic system Anatomy 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 239000000346 nonvolatile oil Substances 0.000 description 1
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- 210000000496 pancreas Anatomy 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
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- 235000004252 protein component Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZFMRLFXUPVQYAU-UHFFFAOYSA-N sodium 5-[[4-[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-2-hydroxybenzoic acid Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3O)N)S(=O)(=O)O)N=NC5=CC(=C(C=C5)O)C(=O)O.[Na+] ZFMRLFXUPVQYAU-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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Classifications
-
- 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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
-
- 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
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/540,657 US5122542A (en) | 1990-06-19 | 1990-06-19 | Hypotriglyceridemic use of certain bis (3,5-di-alkyl-4-hydroxyphenylthio)methanes |
| US540,657 | 1990-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04230213A true JPH04230213A (ja) | 1992-08-19 |
Family
ID=24156398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3173445A Pending JPH04230213A (ja) | 1990-06-19 | 1991-06-19 | ある種のビス（３，５−ジ−アルキル−４−ヒドロキシフェニルチオ）メタン類の血中トリグリセリド減少への用途 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5122542A (OSRAM) |
| EP (1) | EP0462556B1 (OSRAM) |
| JP (1) | JPH04230213A (OSRAM) |
| KR (1) | KR0168649B1 (OSRAM) |
| AT (1) | ATE129151T1 (OSRAM) |
| AU (1) | AU640486B2 (OSRAM) |
| DE (1) | DE69113871T2 (OSRAM) |
| DK (1) | DK0462556T3 (OSRAM) |
| ES (1) | ES2080854T3 (OSRAM) |
| GR (1) | GR3018351T3 (OSRAM) |
| IE (1) | IE69315B1 (OSRAM) |
| TW (1) | TW205542B (OSRAM) |
| ZA (1) | ZA914538B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100004333A1 (en) * | 2004-12-17 | 2010-01-07 | Stocker Roland O | Compositions and methods for treating cardiovascular disorders |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734527A (en) * | 1986-10-17 | 1988-03-29 | Merrell Dow Pharmaceuticals Inc. | Process for preparing 2,6-di-tertiarybutyl-4-mercaptophenol |
| US4954528A (en) * | 1988-12-08 | 1990-09-04 | Merrell Dow Pharmaceuticals Inc. | Hypocholesterolemic use of bis(3,5-di-tertiary-butly-4-hydroxyphenylthio)methane |
| US4900757A (en) * | 1988-12-08 | 1990-02-13 | Merrell Dow Pharmaceuticals Inc. | Hypocholesterolemic and antiatherosclerotic uses of bix(3,5-di-tertiary-butyl-4-hydroxyphenylthio)methane |
| US4959392A (en) * | 1989-07-24 | 1990-09-25 | Merrell Dow Pharmaceuticals Inc. | Method of treating diabetes mellitus |
-
1990
- 1990-06-19 US US07/540,657 patent/US5122542A/en not_active Expired - Fee Related
-
1991
- 1991-06-13 ZA ZA914538A patent/ZA914538B/xx unknown
- 1991-06-14 TW TW080104654A patent/TW205542B/zh active
- 1991-06-14 AU AU78365/91A patent/AU640486B2/en not_active Ceased
- 1991-06-18 IE IE208791A patent/IE69315B1/en not_active IP Right Cessation
- 1991-06-18 ES ES91109943T patent/ES2080854T3/es not_active Expired - Lifetime
- 1991-06-18 KR KR1019910010091A patent/KR0168649B1/ko not_active Expired - Fee Related
- 1991-06-18 AT AT91109943T patent/ATE129151T1/de not_active IP Right Cessation
- 1991-06-18 DE DE69113871T patent/DE69113871T2/de not_active Expired - Fee Related
- 1991-06-18 DK DK91109943.0T patent/DK0462556T3/da active
- 1991-06-18 EP EP91109943A patent/EP0462556B1/en not_active Expired - Lifetime
- 1991-06-19 JP JP3173445A patent/JPH04230213A/ja active Pending
-
1995
- 1995-12-08 GR GR950403470T patent/GR3018351T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69113871T2 (de) | 1996-04-04 |
| DE69113871D1 (de) | 1995-11-23 |
| IE912087A1 (en) | 1992-01-01 |
| EP0462556B1 (en) | 1995-10-18 |
| US5122542A (en) | 1992-06-16 |
| GR3018351T3 (en) | 1996-03-31 |
| IE69315B1 (en) | 1996-09-04 |
| KR920000327A (ko) | 1992-01-29 |
| DK0462556T3 (da) | 1995-11-27 |
| ES2080854T3 (es) | 1996-02-16 |
| KR0168649B1 (ko) | 1999-01-15 |
| TW205542B (OSRAM) | 1993-05-11 |
| EP0462556A2 (en) | 1991-12-27 |
| AU640486B2 (en) | 1993-08-26 |
| ATE129151T1 (de) | 1995-11-15 |
| AU7836591A (en) | 1992-01-02 |
| EP0462556A3 (en) | 1992-03-11 |
| ZA914538B (en) | 1992-03-25 |
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