GB1148550A - Substituted benzylphenyl sulfides and their use as antioxidants - Google Patents
Substituted benzylphenyl sulfides and their use as antioxidantsInfo
- Publication number
- GB1148550A GB1148550A GB5494767A GB5494767A GB1148550A GB 1148550 A GB1148550 A GB 1148550A GB 5494767 A GB5494767 A GB 5494767A GB 5494767 A GB5494767 A GB 5494767A GB 1148550 A GB1148550 A GB 1148550A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- denotes
- reacting
- carbon atoms
- denote
- 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
Links
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical class C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 title abstract 3
- 239000003963 antioxidant agent Substances 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 abstract 2
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical compound OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,148,550. Substituted benzylphenyl sulphides. UNIROYAL Inc. 2 Dec., 1967, No. 54947/67. Heading C2C. [Also in Division C3] The invention comprises substituted benzylphenyl sulphides of the formula in which R 1 , R 2 , R 8 and R 4 denote alkyl groups of 1-12 carbon atoms, cycloalkyl groups of 6-8 carbon atoms or aralkyl groups of 7-9 carbon atoms. Alternatively, R 4 may denote hydrogen. The compounds may be prepared by reacting (a) a mercaptophenol of the formula under alkaline conditions with (b) a compound of the formula in which X denotes a benzothiazolyl sulphide radical or an N,N-dialkyldithiocarbamate residue of the formula -SC(S)NR 5 R 6 , in which R 5 and R 6 denote lower alkyl groups. A number of mercaptophenols suitable as reagents (a) are specified. The reaction may be effected at a temperature up to 100‹ C. in an aqueous medium, preferably containing a water-miscible solvent, or in a two-phase system. Examples are given. The products are useful as antioxidants (see Divisions C3 and C5). Intermediates of the third formula above in which X denotes a benzothiazolyl sulphide radical are obtainable by reacting a phenol of the formula with one molar equivalent each of formaldehyde and 2-mercaptobenzothiazole under acid conditions. A number of phenols which may participate in this reaction are specified. Intermediates of the third formula above in which X denotes an N,N-dialkyldithiocarbamate residue are obtainable by reacting a compound of the formula with carbon disulphide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5494767A GB1148550A (en) | 1967-12-02 | 1967-12-02 | Substituted benzylphenyl sulfides and their use as antioxidants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5494767A GB1148550A (en) | 1967-12-02 | 1967-12-02 | Substituted benzylphenyl sulfides and their use as antioxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1148550A true GB1148550A (en) | 1969-04-16 |
Family
ID=10472537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5494767A Expired GB1148550A (en) | 1967-12-02 | 1967-12-02 | Substituted benzylphenyl sulfides and their use as antioxidants |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1148550A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2448415A1 (en) * | 1973-10-11 | 1975-04-24 | Raychem Corp | ANTIOXYDANTS AND POLYMER COMPOUNDS CONTAINING THESE ANTIOXYDANTS |
| US4611023A (en) * | 1984-02-03 | 1986-09-09 | Ciba-Geigy Corporation | Di-(substituted hydroxyphenylthio) alkane and cycloalkane stabilizers and stabilized compositions |
| WO1998051662A3 (en) * | 1997-05-14 | 2000-03-02 | Atherogenics Inc | Compounds and methods for the inhibition of the expression of vcam-1 |
| US6670398B2 (en) | 1997-05-14 | 2003-12-30 | Atherogenics, Inc. | Compounds and methods for treating transplant rejection |
| US6852878B2 (en) | 1998-05-14 | 2005-02-08 | Atherogenics, Inc. | Thioketals and thioethers for inhibiting the expression of VCAM-1 |
| AU2002300328B2 (en) * | 1997-05-14 | 2006-04-13 | Atherogenics, Inc | Compounds and methods for the inhibition of the expression of VCAM-1 |
| EP1695959A1 (en) * | 1997-05-14 | 2006-08-30 | Atherogenics, Inc. | Compouds and methods for the inhibition of the expression of VCAM-1 |
| US7294737B2 (en) | 2004-04-20 | 2007-11-13 | Atherogenics, Inc. | Process of preparing esters and ethers of probucol and derivatives thereof |
| AU2006202461B2 (en) * | 1997-05-14 | 2009-12-03 | Atherogenics, Inc. | Compositions and methods for the inhibition of the expression of VCAM-1 |
| US8252840B2 (en) | 2007-03-26 | 2012-08-28 | Salutria Pharmaceuticals Llc | Methods of derivatives of probucol for the treatment of type II diabetes |
-
1967
- 1967-12-02 GB GB5494767A patent/GB1148550A/en not_active Expired
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2448415A1 (en) * | 1973-10-11 | 1975-04-24 | Raychem Corp | ANTIOXYDANTS AND POLYMER COMPOUNDS CONTAINING THESE ANTIOXYDANTS |
| US4611023A (en) * | 1984-02-03 | 1986-09-09 | Ciba-Geigy Corporation | Di-(substituted hydroxyphenylthio) alkane and cycloalkane stabilizers and stabilized compositions |
| AU2002300328B2 (en) * | 1997-05-14 | 2006-04-13 | Atherogenics, Inc | Compounds and methods for the inhibition of the expression of VCAM-1 |
| US7087645B2 (en) | 1997-05-14 | 2006-08-08 | Atherogenics, Inc. | Compounds and methods for treating transplant rejection |
| US6548699B1 (en) | 1997-05-14 | 2003-04-15 | Atherogenics, Inc. | Compounds and methods for the inhibition of the expression of VCAM-1 |
| US6602914B2 (en) | 1997-05-14 | 2003-08-05 | Atherogenics, Inc. | Compounds and methods for the inhibition of the expression of VCAM-1 |
| US6617352B2 (en) | 1997-05-14 | 2003-09-09 | Atherogenics, Inc. | Compounds and methods for the inhibition of the expression of VCAM-1 |
| US6670398B2 (en) | 1997-05-14 | 2003-12-30 | Atherogenics, Inc. | Compounds and methods for treating transplant rejection |
| US6828447B2 (en) | 1997-05-14 | 2004-12-07 | Atherogenics, Inc. | Compounds and methods for the inhibition of the expression of VCAM-1 |
| AU2006202461B2 (en) * | 1997-05-14 | 2009-12-03 | Atherogenics, Inc. | Compositions and methods for the inhibition of the expression of VCAM-1 |
| WO1998051662A3 (en) * | 1997-05-14 | 2000-03-02 | Atherogenics Inc | Compounds and methods for the inhibition of the expression of vcam-1 |
| US6121319A (en) * | 1997-05-14 | 2000-09-19 | Atherogenics, Inc. | Monoesters of probucol for the treatment of cardiovascular and inflammatory disease |
| EP1695959A1 (en) * | 1997-05-14 | 2006-08-30 | Atherogenics, Inc. | Compouds and methods for the inhibition of the expression of VCAM-1 |
| US7189870B2 (en) | 1997-05-14 | 2007-03-13 | Atherogenic, Inc. | Compounds and methods for the inhibition of the expression of VCAM-1 |
| US7375252B2 (en) | 1997-05-14 | 2008-05-20 | Atherogenics, Inc. | Compounds and method for the inhibition of the expression of VCAM-1 |
| EA009370B1 (en) * | 1997-05-14 | 2007-12-28 | Атеродженикс, Инк. | Compound and pharmaceutical composition for the inhibition of the expression of vcam-1 |
| EA009987B1 (en) * | 1997-05-14 | 2008-04-28 | Атеродженикс, Инк. | Probucol derivatives for the treatment of diseases mediated by vcam-1 |
| US6852878B2 (en) | 1998-05-14 | 2005-02-08 | Atherogenics, Inc. | Thioketals and thioethers for inhibiting the expression of VCAM-1 |
| US7294737B2 (en) | 2004-04-20 | 2007-11-13 | Atherogenics, Inc. | Process of preparing esters and ethers of probucol and derivatives thereof |
| US8252840B2 (en) | 2007-03-26 | 2012-08-28 | Salutria Pharmaceuticals Llc | Methods of derivatives of probucol for the treatment of type II diabetes |
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