GB908986A - Sulphur-containing dicarboxylic acids and derivatives thereof and a process for the manufacture of same - Google Patents
Sulphur-containing dicarboxylic acids and derivatives thereof and a process for the manufacture of sameInfo
- Publication number
- GB908986A GB908986A GB691161A GB691161A GB908986A GB 908986 A GB908986 A GB 908986A GB 691161 A GB691161 A GB 691161A GB 691161 A GB691161 A GB 691161A GB 908986 A GB908986 A GB 908986A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- acid
- dimercapto
- alkyl
- succinic
- 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
- 238000000034 method Methods 0.000 title abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title 1
- 239000005864 Sulphur Substances 0.000 title 1
- 150000001991 dicarboxylic acids Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- IGEPXHZQIGLLRI-UHFFFAOYSA-N 2,3-bis(acetylsulfanyl)butanedioic acid Chemical compound CC(=O)SC(C(O)=O)C(C(O)=O)SC(C)=O IGEPXHZQIGLLRI-UHFFFAOYSA-N 0.000 abstract 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- ACTRVOBWPAIOHC-UHFFFAOYSA-N succimer Chemical compound OC(=O)C(S)C(S)C(O)=O ACTRVOBWPAIOHC-UHFFFAOYSA-N 0.000 abstract 2
- ACXHQDLWPZQCMF-UHFFFAOYSA-N 3,4-diacetyl-5-sulfanylideneoxolan-2-one Chemical compound C(C)(=O)C1C(=S)OC(C1C(C)=O)=O ACXHQDLWPZQCMF-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 208000002848 Schistosomiasis mansoni Diseases 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 238000007259 addition reaction Methods 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical class [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 abstract 1
- 150000003935 benzaldehydes Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 abstract 1
- -1 carboxylic acid compounds Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000003223 protective agent Substances 0.000 abstract 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony compounds
- C07F9/902—Compounds without antimony-carbon linkages
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises racemic and optically active compounds of the formula, <FORM:0908986/IV (b)/1> wherein R10 stands for a hydrogen atom or an alkyl group other than methyl when R0 is acetyl, and each R0 is a hydrogen atom or an alkyl group or an acyl group other than acetyl when R10 is methyl, or together for a methylene group which may contain an alkylene or aryl group or one or two alkyl groups as substituents, and the anhydrides of the carboxylic acid compounds, specifically DL-2,3-dimercapto-succinic, D-2,3-dimercaptosuccinic, and L-2,3-dimercapto-succinic acids and 2,3-diacetylthiosuccinic acid anhydride, and a process for the preparation of compounds of the above formula in which R10 is a hydrogen or an alkyl group and R0 is a hydrogen or an alkyl or acyl group or the R's together stand for a methylene group which may contain an alkylene or aryl group or one or two alkyl groups as substituents and the anhydrides of carboxylic acids, by reacting thioacetic acid with an acetylene-dicarboxylic acid and either dehydrating or hydrolysing the resulting 2,3-diacetylmercapto-succinic acid and where required esterifying or etherifying the resulting 2,3-dimercapto-succinic acid and/or condensing it with the appropriate aldehyde or ketone, or esterifying the 2,3-diacetylmercapto-succinic acid and isolating the DL-form and if desired resolving the racemic form into the optically active forms. The addition reaction may be carried out in an inert solvent and the hydrolysis in an acidic or basic media. The 2,3-dimercapto-succinic acid or alkyl ester may be condensed with an alkanol or benzaldehyde or substituted benzaldehyde or an alkanone or cycloalkanone. The products have antifungal properties and may be used as plant protecting agents in solvents, as emulsions or as dusting powders with a compatible carrier. They are also suitable in the formation of metal complexes e.g. with trivalent antimony compounds to form complexes useful in the treatment of Schistosoma mansoni infections.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215160A CH395967A (en) | 1960-02-26 | 1960-02-26 | Process for the preparation of racemic and optically active 2,3-dimercaptosuccinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB908986A true GB908986A (en) | 1962-10-24 |
Family
ID=4227064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB691161A Expired GB908986A (en) | 1960-02-26 | 1961-02-24 | Sulphur-containing dicarboxylic acids and derivatives thereof and a process for the manufacture of same |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE600511A (en) |
| CH (1) | CH395967A (en) |
| GB (1) | GB908986A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2214507A (en) * | 1988-01-19 | 1989-09-06 | Erling Sundrehagen | 2,3-dithiosuccinic acid derivative and their use |
| WO2005080325A3 (en) * | 2004-02-17 | 2006-05-04 | Chevron Phillips Chemical Co | Sulfur-containing compositions and processes for making same |
| JP2007525459A (en) * | 2003-04-24 | 2007-09-06 | インサイト・コーポレイション | Azaspiroalkane derivatives as inhibitors of metalloproteases |
| US7585932B2 (en) | 2005-08-16 | 2009-09-08 | Chevron Phillips Chemical Company Lp | Polymer compositions and processes for making and using same |
| US7910666B2 (en) | 2005-08-16 | 2011-03-22 | Chevron Phillips Chemical Company Lp | Mercaptan-hardened epoxy polymer compositions and processes for making and using same |
| US8003748B2 (en) | 2004-02-17 | 2011-08-23 | Chevron Phillips Chemical Company, Lp | Polythiourethane compositions and processes for making and using same |
| US20140091008A1 (en) * | 2010-11-25 | 2014-04-03 | The Queen's University Of Belfast | Process for removing naphthenic acids from crude oil and crude oil distillates |
| CN104211679A (en) * | 2013-06-05 | 2014-12-17 | 首都医科大学 | 1,3-dithiolane derivatives, synthesis, nano structure, activity, and application thereof as lead dispelling agent |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4550193A (en) * | 1982-06-07 | 1985-10-29 | Johnson & Johnson Baby Products Company | Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters |
-
1960
- 1960-02-26 CH CH215160A patent/CH395967A/en unknown
-
1961
- 1961-02-23 BE BE600511A patent/BE600511A/en unknown
- 1961-02-24 GB GB691161A patent/GB908986A/en not_active Expired
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2214507A (en) * | 1988-01-19 | 1989-09-06 | Erling Sundrehagen | 2,3-dithiosuccinic acid derivative and their use |
| US10226459B2 (en) | 2003-04-24 | 2019-03-12 | Incyte Holdings Corporation | Aza spiro alkane derivatives as inhibitors of metalloproteases |
| JP2007525459A (en) * | 2003-04-24 | 2007-09-06 | インサイト・コーポレイション | Azaspiroalkane derivatives as inhibitors of metalloproteases |
| US9801877B2 (en) | 2003-04-24 | 2017-10-31 | Incyte Corporation | AZA spiro alkane derivatives as inhibitors of metalloproteases |
| US9403775B2 (en) | 2003-04-24 | 2016-08-02 | Incyte Corporation | AZA spiro alkane derivatives as inhibitors of metalloproteases |
| US8637497B2 (en) | 2003-04-24 | 2014-01-28 | Incyte Corporation | AZA spiro alkane derivatives as inhibitors of metalloproteases |
| JP4841429B2 (en) * | 2003-04-24 | 2011-12-21 | インサイト・コーポレイション | Azaspiroalkane derivatives as inhibitors of metalloproteases |
| US8039471B2 (en) | 2003-04-24 | 2011-10-18 | Incyte Corporation | Aza spiro alkane derivatives as inhibitors of metalloproteases |
| US7989655B2 (en) | 2004-02-17 | 2011-08-02 | Chevron Phillips Chemical Company Lp | Thiol ester compositions and processes for making and using same |
| US8003748B2 (en) | 2004-02-17 | 2011-08-23 | Chevron Phillips Chemical Company, Lp | Polythiourethane compositions and processes for making and using same |
| US7781484B2 (en) | 2004-02-17 | 2010-08-24 | Chevron Phillips Chemical Company Lp | Thiol ester compositions and processes for making and using same |
| US7713326B2 (en) | 2004-02-17 | 2010-05-11 | Agrium Inc. | Controlled release fertilizer material and process for production thereof |
| US7557236B2 (en) | 2004-02-17 | 2009-07-07 | Chevron Phillips Chemical Company Lp | Thiol ester compositions and processes for making and using same |
| WO2005080325A3 (en) * | 2004-02-17 | 2006-05-04 | Chevron Phillips Chemical Co | Sulfur-containing compositions and processes for making same |
| US7910666B2 (en) | 2005-08-16 | 2011-03-22 | Chevron Phillips Chemical Company Lp | Mercaptan-hardened epoxy polymer compositions and processes for making and using same |
| US7585932B2 (en) | 2005-08-16 | 2009-09-08 | Chevron Phillips Chemical Company Lp | Polymer compositions and processes for making and using same |
| US20140091008A1 (en) * | 2010-11-25 | 2014-04-03 | The Queen's University Of Belfast | Process for removing naphthenic acids from crude oil and crude oil distillates |
| US9856422B2 (en) * | 2010-11-25 | 2018-01-02 | The Queen's University Of Belfast | Process for removing naphthenic acids from crude oil and crude oil distillates |
| CN104211679A (en) * | 2013-06-05 | 2014-12-17 | 首都医科大学 | 1,3-dithiolane derivatives, synthesis, nano structure, activity, and application thereof as lead dispelling agent |
Also Published As
| Publication number | Publication date |
|---|---|
| BE600511A (en) | 1961-08-23 |
| CH395967A (en) | 1965-07-31 |
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