IE41032L - Pharmaceutical composition containing methylamine¹derivatives - Google Patents
Pharmaceutical composition containing methylamine¹derivativesInfo
- Publication number
- IE41032L IE41032L IE750974A IE97475A IE41032L IE 41032 L IE41032 L IE 41032L IE 750974 A IE750974 A IE 750974A IE 97475 A IE97475 A IE 97475A IE 41032 L IE41032 L IE 41032L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- prepared
- alkyl
- reacting
- acid
- Prior art date
Links
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
- A61K31/13—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/08—Monoamines containing alkyl groups having a different number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1467739 1,1-Dialkyl-alkylamines and precursors LABAZ 15 May 1975 [20 May 1974] 20738/75 Heading C2C [Also in Division A5] Compounds of formula 'wherein R 1 and B 3 are H or alkyl, alkenyl or alkynyl of up to 6 C atoms and R 2 is C 2 -C 7 alkyl, alkenyl or alkynyl, other than CH= CHR 4 or C#CR 4 (wherein R 4 is H or C 1 -C 5 alkyl), and the total number of carbon atoms in R 1 , R 2 and R 3 is not more than 13, are prepared by treating an isocyanate or formamide of the general formula wherein A is -N=C=O or -NHCHO, with a strong acid and treating the resulting acid addition salt with a base. The resulting free base may be reacted with an acid to form a pharmaceutically acceptable salt. Compounds of Formula I wherein R 1 and R 3 are C 1 -C 3 alkyl or C 2 -C 3 alkenyl or alkynyl and R 2 is -CH 2 -R 5 , wherein R 1 , R 3 and R 5 are identical, can also be prepared by heating, in an anhydrous ether, a nitrate of formula with an organo-magnesium compound of formula wherein X is Cl, Br or I, and hydrolysing the complex thus formed. Compounds of Formula I wherein R and R 3 , are H or C 1 -C 6 alkyl and R 2 is ethynyl may be prepared by reacting sodamide with a compound of Formula wherein Hal is Cl or Br. Compounds of Formula I wherein R 1 and R 3 or C 1 -C 6 alkyl and R 2 is a radical of formula -C#CR 4 (wherein R 4 is C 1 -C 5 alkyl) are prepared by reacting a compound of formula wherein Me is alkali metal, with a halide of formula wherein Hal is Cl or Br. Compounds of Formula I wherein R 1 and R 3 are H or C 1 -C 6 alkyl and R 2 is alkenyl of formula -CH=CHR 4 (wherein R 4 is H or C 1 -C 5 alkyl) are prepared by hydrogenating in an appropriate solvent, and in the presence of a Lindlar catalyst, a compound of formula Isocyanates (II) are prepared (a) by reacting an amide of formula with chlorine or bromine in an alkaline medium, or (b) by reacting an acid of formula with a chlorinating agent such as thionyl chloride or oxalyl chloride, to obtain the corresponding acyl chloride, which is then treated with a metal azide, or by heating a compound of Formula (X) with hydrogen azide in an acid medium; the isocyanate thus formed being hydrolysed immediately to the corresponding amine. Formamides (II) are prepared by heating an alcohol of formula with an alkali metal cyanide in the presence of an acid. Amides (IX) may be prepared by reacting anhydrous ammonia with acids of Formula X or with the halides thereof. Acids (X) may be prepared by reacting alcohols (XI) with formic acid in a sulphuric acid medium. Alcohols (XI) may be prepared by reacting an organo-lithium compound with an appropriate ketone in an anhydrous ether medium. Halides (V) may be prepared by treating a 1,1 - dialkyl - 1 - ethynylcarbanol with cuprous chloride and HCl in the presence of copperbronze powder and calcium chloride. The pharmaceutically acceptable acid addition salts of the compounds of Formula I are prepared by reacting the free base with an appropriate acid.
[GB1467739A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE144519A BE815273A (en) | 1974-05-20 | 1974-05-20 | METHYLAMINE ACTIVE DERIVATIVES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41032L true IE41032L (en) | 1975-10-20 |
| IE41032B1 IE41032B1 (en) | 1979-10-10 |
Family
ID=3842664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE974/75A IE41032B1 (en) | 1974-05-20 | 1975-04-30 | Active derivative of methylamine, therapeutic compositions containing the same and processes for preparing the said derivatives and compositions |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS569498B2 (en) |
| AR (1) | AR208548A1 (en) |
| AT (1) | AT341488B (en) |
| BE (1) | BE815273A (en) |
| CA (1) | CA1048549A (en) |
| CH (1) | CH605606A5 (en) |
| DE (1) | DE2522218C3 (en) |
| DK (1) | DK145779C (en) |
| ES (1) | ES437790A1 (en) |
| FI (1) | FI61182C (en) |
| FR (1) | FR2271811B1 (en) |
| GB (2) | GB1467740A (en) |
| HU (1) | HU173890B (en) |
| IE (1) | IE41032B1 (en) |
| IT (1) | IT1049427B (en) |
| NL (1) | NL172120C (en) |
| NO (1) | NO139733C (en) |
| OA (1) | OA05004A (en) |
| SE (1) | SE434262B (en) |
| SU (1) | SU1292666A3 (en) |
| YU (1) | YU39318B (en) |
| ZA (1) | ZA752863B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201725A (en) * | 1974-05-20 | 1980-05-06 | Labaz | Secondary amines |
| GR61148B (en) * | 1976-06-03 | 1978-09-27 | Labaz | Preparation process of active methylamine derivatives |
| JPS5427369A (en) * | 1977-08-01 | 1979-03-01 | Hitachi Ltd | Pattern formation method |
| FR2470758A1 (en) | 1979-12-07 | 1981-06-12 | Sanofi Sa | METHOD FOR FIXING ALKYL GROUPS ON A CARBONIC CHAIN CARRYING A FUNCTIONAL GROUP |
| WO2001008685A1 (en) * | 1999-07-30 | 2001-02-08 | Vertex Pharmaceuticals Incorporated | Acyclic and cyclic amine derivatives |
| CN114235991A (en) * | 2021-11-27 | 2022-03-25 | 山东省烟台市农业科学研究院 | High performance liquid chromatography for determining sec-butylamine content |
-
1974
- 1974-05-20 BE BE144519A patent/BE815273A/en not_active IP Right Cessation
- 1974-05-20 ES ES437790A patent/ES437790A1/en not_active Expired
-
1975
- 1975-04-30 IE IE974/75A patent/IE41032B1/en unknown
- 1975-05-02 ZA ZA00752863A patent/ZA752863B/en unknown
- 1975-05-09 HU HU75LA865A patent/HU173890B/en unknown
- 1975-05-14 YU YU1226/75A patent/YU39318B/en unknown
- 1975-05-15 AT AT371575A patent/AT341488B/en not_active IP Right Cessation
- 1975-05-15 CA CA75227044A patent/CA1048549A/en not_active Expired
- 1975-05-15 SE SE7505606A patent/SE434262B/en not_active IP Right Cessation
- 1975-05-15 GB GB2833676A patent/GB1467740A/en not_active Expired
- 1975-05-15 GB GB2073875A patent/GB1467739A/en not_active Expired
- 1975-05-15 FR FR7515118A patent/FR2271811B1/fr not_active Expired
- 1975-05-16 NO NO75751771A patent/NO139733C/en unknown
- 1975-05-16 NL NLAANVRAGE7505853,A patent/NL172120C/en not_active IP Right Cessation
- 1975-05-16 DK DK216575A patent/DK145779C/en active
- 1975-05-17 OA OA55502A patent/OA05004A/en unknown
- 1975-05-19 AR AR258840A patent/AR208548A1/en active
- 1975-05-20 IT IT23511/75A patent/IT1049427B/en active
- 1975-05-20 FI FI751468A patent/FI61182C/en not_active IP Right Cessation
- 1975-05-20 CH CH643975A patent/CH605606A5/fr not_active IP Right Cessation
- 1975-05-20 DE DE2522218A patent/DE2522218C3/en not_active Expired
- 1975-05-20 JP JP6086675A patent/JPS569498B2/ja not_active Expired
-
1983
- 1983-03-25 SU SU833567049A patent/SU1292666A3/en active
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