AT263756B - Verfahren zur Herstellung neuer substituierter Phenylacetamide - Google Patents
Verfahren zur Herstellung neuer substituierter PhenylacetamideInfo
- Publication number
- AT263756B AT263756B AT778266A AT778266A AT263756B AT 263756 B AT263756 B AT 263756B AT 778266 A AT778266 A AT 778266A AT 778266 A AT778266 A AT 778266A AT 263756 B AT263756 B AT 263756B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- group
- new substituted
- general formula
- production
- Prior art date
Links
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- -1 butyloxy, amyloxy, hexyloxy, octyloxy Chemical group 0.000 claims description 7
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RSMPEQBSFXBQMJ-UHFFFAOYSA-N 2-(4-butoxyphenyl)acetamide Chemical compound CCCCOC1=CC=C(CC(N)=O)C=C1 RSMPEQBSFXBQMJ-UHFFFAOYSA-N 0.000 description 1
- KLJMYYFCWBVKEE-UHFFFAOYSA-N 2-(4-butoxyphenyl)acetic acid Chemical compound CCCCOC1=CC=C(CC(O)=O)C=C1 KLJMYYFCWBVKEE-UHFFFAOYSA-N 0.000 description 1
- QFTGSQHGASRUOE-UHFFFAOYSA-N 2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound CC(C)COC1=CC=C(CC(N)=O)C=C1 QFTGSQHGASRUOE-UHFFFAOYSA-N 0.000 description 1
- VUGNKJWGAHEGGO-UHFFFAOYSA-N 2-[4-(3-methylbutoxy)phenyl]acetamide Chemical compound CC(C)CCOC1=CC=C(CC(N)=O)C=C1 VUGNKJWGAHEGGO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE648892A BE648892A (d) | 1964-06-05 | 1964-06-05 | |
| BE661226A BE661226A (fr) | 1965-03-17 | 1965-03-17 | Acides arylacethydroxamiques, amides correspondants et procedes de preparation. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT263756B true AT263756B (de) | 1968-08-12 |
Family
ID=25655931
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT778266A AT263756B (de) | 1964-06-05 | 1965-06-03 | Verfahren zur Herstellung neuer substituierter Phenylacetamide |
| AT505665A AT262973B (de) | 1964-06-05 | 1965-06-03 | Verfahren zur Herstellung neuer substituierter Phenylacethydroxamsäuren |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT505665A AT262973B (de) | 1964-06-05 | 1965-06-03 | Verfahren zur Herstellung neuer substituierter Phenylacethydroxamsäuren |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3479396A (d) |
| AT (2) | AT263756B (d) |
| BR (1) | BR6569972D0 (d) |
| CS (1) | CS161685B2 (d) |
| DE (2) | DE1280254B (d) |
| DK (1) | DK117353B (d) |
| ES (1) | ES313832A1 (d) |
| FI (1) | FI51806C (d) |
| FR (1) | FR1484624A (d) |
| GB (2) | GB1110520A (d) |
| NL (2) | NL6406688A (d) |
| OA (1) | OA02009A (d) |
| SE (1) | SE345260B (d) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3890377A (en) * | 1968-08-15 | 1975-06-17 | Lilly Co Eli | 3-Substituted phenylalkanohydroxamic acids |
| FR2108943A1 (en) * | 1970-10-22 | 1972-05-26 | Bouchara Emile | Alkenyl-or alkynylthiophenylacetic acid derivs - - as antirheumatic analgesic and antiinflammatory agents |
| US3978116A (en) * | 1971-11-04 | 1976-08-31 | Syntex Corporation | 2-naphthyl acetic acid derivatives and compositions and methods thereof |
| US4082707A (en) * | 1973-01-08 | 1978-04-04 | Societa Italo-Britannica L. Manetti-H. Roberts & Co. | 2-(4-isobutylphenyl)-propiohydroxamic acid and a procedure for its preparation |
| FR2285867A1 (fr) * | 1974-09-30 | 1976-04-23 | Lafon Labor | Derives du diphenylsulfoxyde |
| US4061668A (en) * | 1974-12-06 | 1977-12-06 | Societa Italo-Britannica L. Manetti - H. Roberts & C. | Process for the preparation of 2-(4-isobutylphenyl)-propiohydroxamic acid |
| GB1520812A (en) * | 1975-10-02 | 1978-08-09 | Lafon Labor | Benzhydrylsulphinyl derivatives |
| US4185100A (en) * | 1976-05-13 | 1980-01-22 | Johnson & Johnson | Topical anti-inflammatory drug therapy |
| US4473565A (en) * | 1976-05-13 | 1984-09-25 | Johnson & Johnson | Topical anti-inflammatory drug therapy |
| NL7614113A (nl) * | 1976-12-18 | 1978-06-20 | Akzo Nv | Hydroxamzuren. |
| US4173652A (en) * | 1976-12-18 | 1979-11-06 | Akzona Incorporated | Pharmaceutical hydroxamic acid compositions and uses thereof |
| GB8531839D0 (en) * | 1985-12-30 | 1986-02-05 | Wellcome Found | Aryl derivatives |
| US4792560A (en) * | 1985-04-03 | 1988-12-20 | Rorer Pharmaceutical Corporation | Quinoline hydroxamates and their use as modulators of arachidonic acid metabolic pathways |
| US4604407A (en) * | 1985-04-04 | 1986-08-05 | E. R. Squibb & Sons, Inc. | Hydroxamates |
| US5036157A (en) * | 1986-03-11 | 1991-07-30 | Burroughs Wellcome Co. | Aryl derivatives |
| US4906667A (en) * | 1986-07-30 | 1990-03-06 | E. R. Squibb & Sons, Inc. | Phenyl hydroxamic acids including a hetero-containing substituent |
| US4731382A (en) * | 1986-12-29 | 1988-03-15 | Bristol-Myers Company | Lipoxygenase inhibitory phenylalkanohydroxamic acids |
| US7312247B2 (en) | 2001-03-27 | 2007-12-25 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US7842727B2 (en) | 2001-03-27 | 2010-11-30 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US6495719B2 (en) | 2001-03-27 | 2002-12-17 | Circagen Pharmaceutical | Histone deacetylase inhibitors |
| US8026280B2 (en) | 2001-03-27 | 2011-09-27 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| AU2003243272A1 (en) | 2002-05-22 | 2003-12-12 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on alpha-ketoepoxide compounds |
| EP1567142A4 (en) * | 2002-11-20 | 2005-12-14 | Errant Gene Therapeutics Llc | TREATMENT OF PULMONARY CELLS WITH HISTONE DEACETYLASE INHIBITORS |
| TW200418825A (en) * | 2002-12-16 | 2004-10-01 | Hoffmann La Roche | Novel (R)-and (S) enantiomers of thiophene hydroxamic acid derivatives |
| US8796330B2 (en) * | 2006-12-19 | 2014-08-05 | Methylgene Inc. | Inhibitors of histone deacetylase and prodrugs thereof |
| EP2573069A3 (en) * | 2006-12-19 | 2013-05-22 | MethylGene Inc. | Inhibitors of histone deacetylase and prodrugs thereof |
| US10343993B2 (en) | 2015-03-02 | 2019-07-09 | Pliva Hrvatska D.O.O. | Processes and intermediates for the preparation of Pimavanserin |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2501896A (en) * | 1950-03-28 | Dichlorovinm ethers | ||
| US2279560A (en) * | 1940-05-08 | 1942-04-14 | Du Pont | Viscous hydrocarbon oil |
| US2279973A (en) * | 1940-05-08 | 1942-04-14 | Du Pont | Stabilization of organic substances |
| US2397508A (en) * | 1943-05-29 | 1946-04-02 | Standard Oil Co | Hydroxamic acids |
| US2456785A (en) * | 1945-07-28 | 1948-12-21 | Winthrop Stearns Inc | Production of amides |
| US2489348A (en) * | 1947-01-15 | 1949-11-29 | Hoffmann La Roche | Production of arylacetic acids and amides |
| US3189432A (en) * | 1958-08-04 | 1965-06-15 | Velsicol Chemical Corp | Method of destroying growing weeds |
| DE1166766B (de) * | 1961-08-04 | 1964-04-02 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen Phenylalkylcarbonsaeureamiden |
| BE646803A (d) * | 1963-04-26 | 1964-10-20 | Kuhlmann Ets |
-
1964
- 1964-06-12 NL NL6406688A patent/NL6406688A/xx unknown
-
1965
- 1965-05-25 GB GB23882/67A patent/GB1110520A/en not_active Expired
- 1965-05-25 GB GB22074/65A patent/GB1102867A/en not_active Expired
- 1965-05-27 BR BR169972/65A patent/BR6569972D0/pt unknown
- 1965-06-01 DE DEM65418A patent/DE1280254B/de active Pending
- 1965-06-01 DE DE19651618708 patent/DE1618708A1/de active Pending
- 1965-06-02 FR FR19261A patent/FR1484624A/fr not_active Expired
- 1965-06-03 SE SE7271/65A patent/SE345260B/xx unknown
- 1965-06-03 AT AT778266A patent/AT263756B/de active
- 1965-06-03 AT AT505665A patent/AT262973B/de active
- 1965-06-03 DK DK280465AA patent/DK117353B/da unknown
- 1965-06-04 CS CS3630A patent/CS161685B2/cs unknown
- 1965-06-04 OA OA52053A patent/OA02009A/xx unknown
- 1965-06-04 ES ES0313832A patent/ES313832A1/es not_active Expired
- 1965-06-05 FI FI651347A patent/FI51806C/fi active
- 1965-06-08 NL NL656507265A patent/NL143132B/xx not_active IP Right Cessation
-
1968
- 1968-08-12 US US751710A patent/US3479396A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL143132B (nl) | 1974-09-16 |
| NL6507265A (d) | 1965-12-06 |
| OA02009A (fr) | 1970-05-05 |
| DE1768406A1 (de) | 1972-06-08 |
| ES313832A1 (es) | 1966-02-16 |
| DE1618708A1 (de) | 1969-10-02 |
| FI51806B (d) | 1976-12-31 |
| GB1102867A (en) | 1968-02-14 |
| NL6406688A (d) | 1965-12-06 |
| CS161685B2 (d) | 1975-06-10 |
| DE1280254B (de) | 1968-10-17 |
| FI51806C (fi) | 1977-04-12 |
| GB1110520A (en) | 1968-04-18 |
| US3479396A (en) | 1969-11-18 |
| SE345260B (d) | 1972-05-23 |
| BR6569972D0 (pt) | 1973-08-28 |
| AT262973B (de) | 1968-07-10 |
| FR1484624A (fr) | 1967-06-16 |
| DK117353B (da) | 1970-04-20 |
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