GB809286A - Basically substituted butyric acid anilides and process for their manufacture - Google Patents
Basically substituted butyric acid anilides and process for their manufactureInfo
- Publication number
- GB809286A GB809286A GB19411/55A GB1941155A GB809286A GB 809286 A GB809286 A GB 809286A GB 19411/55 A GB19411/55 A GB 19411/55A GB 1941155 A GB1941155 A GB 1941155A GB 809286 A GB809286 A GB 809286A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- phenetidide
- butyric acid
- compounds
- butylamino
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- UHANVDZCDNSILX-UHFFFAOYSA-N n-phenylbutanamide Chemical class CCCC(=O)NC1=CC=CC=C1 UHANVDZCDNSILX-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Chemical group 0.000 abstract 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 abstract 2
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 2
- FRFKEFWFWCOJQG-MBXJOHMKSA-N (Z)-2-amino-N-phenylbut-2-enamide Chemical compound N/C(/C(=O)NC1=CC=CC=C1)=C\C FRFKEFWFWCOJQG-MBXJOHMKSA-N 0.000 abstract 1
- XIZLDQRMOTWJQD-DAXSKMNVSA-N (z)-2-(butylamino)but-2-enoic acid Chemical compound CCCCN\C(=C/C)C(O)=O XIZLDQRMOTWJQD-DAXSKMNVSA-N 0.000 abstract 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 abstract 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 abstract 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 abstract 1
- WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
Abstract
The invention comprises compounds of the general formula <FORM:0809286/IV (b)/1> in which R1 is hydrogen or an alkyl or alkoxy group of 1-4 carbon atoms, and is preferably a para-alkoxy group of 1 to 3 carbon atoms, and R2 is hydrogen or an alkyl group, and acid addition salts of these compounds. The compounds are made by reacting an acetoacetic acid anilide with ammonia or a primary alkylamine and a reducing agent and if desired subjecting the product to alkylation. Suitable acetoacetic acid anilides include the acetoacetyl derivatives of p-anisidine, p-phenetidine, p-toluidine and p-ethyl aniline, and the corresponding o- and m-derivatives. Suitable amines include methylamine, ethylamine, isopropylamine, butylamine and isobutylamine. The reaction may be carried out in a single stage or in two stages with isolation of the intermediate aminocrotonic acid anilide. The reduction is suitably effected by nascent hydrogen, aluminium or sodium amalgam in alcohol, lithium aluminium hydride, sodium boron hydride, electrolytic reduction or catalytic hydrogenation, preferably in solution in a solvent such as methanol or ethanol. The basic anilides may be converted into their salts with for example formic, acetic, malonic, maleic, succinic, lactic, malic, tartaric, citric, hydroxyethane sulphonic, aceturic, 1-phenyl-2 : 3 - dimethyl - pyrazolone - (5) - 4 - methylaminomethane sulphonic, ethylenediaminetetracetic, benzoic and salicyclic acids. Examples describe the preparation of b -n-butylamino-butyric acid-p-phenetidide, b -n-butylamino-butyric acid anilide, methylamino-butyric acid-p-phenetidide and b -amino-butyric acid-p-phenetidide, and the isolation of these compounds as free bases or acid addition salts. Butylamino-crotonic acid para-phenetidide is obtained as an intermediate by the reaction of acetoacetic acid p-phenetidide with n-butylamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE809286X | 1954-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB809286A true GB809286A (en) | 1959-02-18 |
Family
ID=6723276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19411/55A Expired GB809286A (en) | 1954-07-05 | 1955-07-05 | Basically substituted butyric acid anilides and process for their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB809286A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3096237A (en) * | 1959-05-13 | 1963-07-02 | Bayer Ag | Methods of combating mites and fungi |
| US4237068A (en) * | 1971-07-28 | 1980-12-02 | Astra Pharmaceutical Products, Inc. | Primary aminoacylanilides |
| US4353914A (en) | 1978-02-07 | 1982-10-12 | Orion-Yhtyma Oy | Antitussive anilides |
| GB2129424A (en) * | 1982-08-27 | 1984-05-16 | Pharmaton Sa | Basic acetanilides |
-
1955
- 1955-07-05 GB GB19411/55A patent/GB809286A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3096237A (en) * | 1959-05-13 | 1963-07-02 | Bayer Ag | Methods of combating mites and fungi |
| US4237068A (en) * | 1971-07-28 | 1980-12-02 | Astra Pharmaceutical Products, Inc. | Primary aminoacylanilides |
| US4353914A (en) | 1978-02-07 | 1982-10-12 | Orion-Yhtyma Oy | Antitussive anilides |
| GB2129424A (en) * | 1982-08-27 | 1984-05-16 | Pharmaton Sa | Basic acetanilides |
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