DE2711686C3 - Verfahren zur Herstellung von Isobutyramiden - Google Patents
Verfahren zur Herstellung von IsobutyramidenInfo
- Publication number
- DE2711686C3 DE2711686C3 DE2711686A DE2711686A DE2711686C3 DE 2711686 C3 DE2711686 C3 DE 2711686C3 DE 2711686 A DE2711686 A DE 2711686A DE 2711686 A DE2711686 A DE 2711686A DE 2711686 C3 DE2711686 C3 DE 2711686C3
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- isobutyramides
- preparation
- bromo
- isobutyramide
- 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 claims description 6
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical class CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 title claims 3
- 229940047889 isobutyramide Drugs 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 239000012454 non-polar solvent Substances 0.000 claims 2
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 claims 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical group OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WNWIKDZYZPGMDJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(2-cyanoethyl)-2-methylpropanamide Chemical compound N#CCCNC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 WNWIKDZYZPGMDJ-UHFFFAOYSA-N 0.000 description 1
- RUQYIZFMVMFTAE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(4-cyanobutyl)-2-methylpropanamide Chemical compound N#CCCCCNC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RUQYIZFMVMFTAE-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 230000000999 hypotriglyceridemic effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VMMXVYZCORHEDE-UHFFFAOYSA-N n-(2-cyanoethyl)-2-(4-fluorophenoxy)-2-methylpropanamide Chemical compound N#CCCNC(=O)C(C)(C)OC1=CC=C(F)C=C1 VMMXVYZCORHEDE-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10634/76A GB1518764A (en) | 1976-03-17 | 1976-03-17 | Isobutyramides their preparation and therapeutic composititions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2711686A1 DE2711686A1 (de) | 1977-09-29 |
| DE2711686B2 DE2711686B2 (de) | 1979-04-12 |
| DE2711686C3 true DE2711686C3 (de) | 1979-11-29 |
Family
ID=9971495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2711686A Expired DE2711686C3 (de) | 1976-03-17 | 1977-03-17 | Verfahren zur Herstellung von Isobutyramiden |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4131617A (enExample) |
| JP (1) | JPS52113932A (enExample) |
| AR (1) | AR213430A1 (enExample) |
| AT (1) | AT346315B (enExample) |
| BE (1) | BE852557A (enExample) |
| CH (1) | CH598201A5 (enExample) |
| DE (1) | DE2711686C3 (enExample) |
| DK (1) | DK118177A (enExample) |
| ES (1) | ES456943A1 (enExample) |
| FR (1) | FR2344528A1 (enExample) |
| GB (1) | GB1518764A (enExample) |
| MX (1) | MX4593E (enExample) |
| MY (1) | MY8000099A (enExample) |
| NL (1) | NL7702892A (enExample) |
| NZ (1) | NZ183560A (enExample) |
| OA (1) | OA05605A (enExample) |
| PT (1) | PT66305B (enExample) |
| ZA (1) | ZA771613B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965825A (en) | 1981-11-03 | 1990-10-23 | The Personalized Mass Media Corporation | Signal processing apparatus and methods |
| US7910624B1 (en) | 1995-03-03 | 2011-03-22 | The Trustees Of Boston University | Compositions for the treatment of blood disorders |
| AU696167B2 (en) * | 1993-10-29 | 1998-09-03 | Trustees Of Boston University | Physiologically stable compositions of butyric acid, and butyric acid salts and derivatives as anti-neoplastic agents |
| US6011000A (en) * | 1995-03-03 | 2000-01-04 | Perrine; Susan P. | Compositions for the treatment of blood disorders |
| CA2324426A1 (en) * | 1998-02-11 | 1999-08-19 | Douglas V. Faller | Compositions and methods for the treatment of cystic fibrosis |
| WO2010105112A1 (en) * | 2009-03-11 | 2010-09-16 | Hemaquest Pharmaceuticals, Inc. | Detection of short-chain fatty acids in biological samples |
| US20110086869A1 (en) | 2009-09-24 | 2011-04-14 | The Trustees Of Boston University | Methods for treating viral disorders |
| MA33899B1 (fr) | 2009-12-08 | 2013-01-02 | Hemaquest Pharmaceuticals Inc | Procedes et regimes a faible dose pour des troubles des globules rouges |
| WO2011113013A2 (en) | 2010-03-11 | 2011-09-15 | Hemaquest Pharmaceuticals, Inc. | Methods and compositions for treating viral or virally-induced conditions |
| GB2567093A (en) | 2016-07-15 | 2019-04-03 | Viracta Therapeutics Inc | Histone deacetylase inhibitors for use in immunotherapy |
| AU2020283590A1 (en) | 2019-05-31 | 2022-01-20 | Viracta Subsidiary, Inc. | Methods of treating virally associated cancers with histone deacetylase inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1041982A (en) * | 1963-09-30 | 1966-09-07 | Boots Pure Drug Co Ltd | Herbicidal compounds and compositions |
-
1976
- 1976-03-17 GB GB10634/76A patent/GB1518764A/en not_active Expired
-
1977
- 1977-03-09 NZ NZ183560A patent/NZ183560A/xx unknown
- 1977-03-15 PT PT66305A patent/PT66305B/pt unknown
- 1977-03-16 MX MX775542U patent/MX4593E/es unknown
- 1977-03-17 JP JP2874477A patent/JPS52113932A/ja active Granted
- 1977-03-17 ES ES456943A patent/ES456943A1/es not_active Expired
- 1977-03-17 CH CH332477A patent/CH598201A5/xx not_active IP Right Cessation
- 1977-03-17 AT AT183077A patent/AT346315B/de not_active IP Right Cessation
- 1977-03-17 FR FR7707923A patent/FR2344528A1/fr active Granted
- 1977-03-17 OA OA56107A patent/OA05605A/xx unknown
- 1977-03-17 US US05/778,724 patent/US4131617A/en not_active Expired - Lifetime
- 1977-03-17 BE BE175857A patent/BE852557A/xx not_active IP Right Cessation
- 1977-03-17 DK DK118177A patent/DK118177A/da not_active Application Discontinuation
- 1977-03-17 ZA ZA00771613A patent/ZA771613B/xx unknown
- 1977-03-17 AR AR266882A patent/AR213430A1/es active
- 1977-03-17 NL NL7702892A patent/NL7702892A/xx unknown
- 1977-03-17 DE DE2711686A patent/DE2711686C3/de not_active Expired
-
1980
- 1980-12-31 MY MY198099A patent/MY8000099A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ183560A (en) | 1978-07-28 |
| ATA183077A (de) | 1978-03-15 |
| FR2344528A1 (fr) | 1977-10-14 |
| DK118177A (da) | 1977-09-18 |
| AT346315B (de) | 1978-11-10 |
| JPS52113932A (en) | 1977-09-24 |
| PT66305B (en) | 1978-08-11 |
| US4131617A (en) | 1978-12-26 |
| OA05605A (fr) | 1981-04-30 |
| MX4593E (es) | 1982-06-25 |
| FR2344528B1 (enExample) | 1980-03-14 |
| JPS5647179B2 (enExample) | 1981-11-07 |
| AR213430A1 (es) | 1979-01-31 |
| BE852557A (fr) | 1977-07-18 |
| ZA771613B (en) | 1978-02-22 |
| GB1518764A (en) | 1978-07-26 |
| NL7702892A (nl) | 1977-09-20 |
| MY8000099A (en) | 1980-12-31 |
| PT66305A (en) | 1977-04-01 |
| ES456943A1 (es) | 1978-01-16 |
| DE2711686B2 (de) | 1979-04-12 |
| DE2711686A1 (de) | 1977-09-29 |
| CH598201A5 (enExample) | 1978-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |