GB685696A - Process for the manufacture of anti-histaminic compounds - Google Patents
Process for the manufacture of anti-histaminic compoundsInfo
- Publication number
- GB685696A GB685696A GB26316/49A GB2631649A GB685696A GB 685696 A GB685696 A GB 685696A GB 26316/49 A GB26316/49 A GB 26316/49A GB 2631649 A GB2631649 A GB 2631649A GB 685696 A GB685696 A GB 685696A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridyl
- phenyl
- give
- carbinol
- alkyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Pyridylpropylamines of the formula Py-CHAr-CH2-CH2-R, wherein Ar stands for phenyl or an alkyl-, alkoxy-, dialkylamino-, chloro-, or bromo-phenyl, or for 2-thienyl, Py stands for 2-pyridyl and R stands for a dialkylamino-, piperidino-, pyrrolidino-, or morpholino-group are prepared by reacting a ketone Ar-CO-CH2-CH2-R with an organometallic 2-pyridyl compound, e.g. 2-pyridyllithium or 2-pyridyl magnesium halide) to give a carbinol Py-CAr(OH)-CH2-CH2-R, followed by replacement of the hydroxyl group by a hydrogen atom. The alkyl and alkoxy groups have less than 6 carbon atoms. The carbinol may be dehydrated to give a compound of formula Py-C(Ar)=CH-CH2-R, followed by hydrogenation. Alternatively, the carbinol is reacted to give Py-C(Ar) (Cl)-CH2-CH2-R, or with phosphorus tribromide or hydrogen bromide to give the corresponding bromine compound, followed by removal of hydrogen bromide, e.g. by heating with dimethylamine, to give the unsaturated amine, and reducing the latter. Or the carbinol may be converted with thionyl chloride to the chloride, which on reduction with zinc dust and acetic acid gives the substituted propane. The starting compounds are made by the Mannich reaction from formaldehyde and the appropriate amine, e.g. dialkylamines, piperidine, pyrrolidine or morpholine and acetophenone or its substitution products. The products may be converted to salts with, e.g. hydrochloric, hydrobromic, sulphuric, phosphoric, salicylic, tartaric, maleic, succinic, citric or lactic acids. In examples: (1) 2-pyridyllithium and b - dimethylaminopropiophenone are reacted to give phenyl-(21-pyridyl1) b -dimethylaminoethylcarbinol. The latter is converted to the bromide with phosphorus tribromide or hydrogen bromide and the product on heating quinoline or dimethyl aniline gives 1 - phenyl - 1 - (21 - pyridyl) - 3 - dimethyl - aminopropene-1 and the latter is hydrogenated to 1-phenyl-1-(21-pyridyl)-3-dimethylaminopropane. The substituted carbinol may alternatively be converted to the substituted propane by reaction with thionyl chloride, and reduction of the product with zinc dust and acetic acid. By similar reactions are prepared (2) 1-(p-methoxyphenyl) - 1 - (21 - pyridyl) - 3 - dimethylaminopropane; (3) 1-(p-chlorophenyl)-1-(21 - pyridyl) - 3 - dimethylaminopropane; (4) 1-(phenyl)-1-(21-pyridyl)-3-diethylaminopropane; (5) 1 - phenyl - 1 - (21 - pyridyl) - 3 - N - piperidinopropane; (6) 1-phenyl-1-(21-pyridyl)-3-pyrrolidyl - propane; (7) 1 - (p - chlorophenyl)-1 - (21 - pyridyl) - 3 - pyrrolidyl - propane. Also mentioned are 1 - (211 - pyridyl) - 3 - dimethylaminopropanes substituted at the 1-position by a (21-thienyl)-, (p-methylphenyl)-, (4-dimethyl - aminophenyl) -, (2,3 - dimethoxyphenyl)-, or (p-isopropylphenyl)-radical. Specifications 307,304, [Class 2 (iii)], and 646,198 are referred to. As open to inspection under Sect. 91, the Specification comprises also the preparation by the above methods of 1-(21-thiazyl-1-(211-pyridyl) - 3 - dimethylaminopropane and of other compounds of the general formula Py-CH(R2)-CH2)n-R1, where Py is a pyridine ring generally which may be substituted by halogen, alkoxy, or alkyl groups, n is an integer from 2 to 4, R1 is dialkylamino, piperidino, pyrrolidino or morpholino, and R2 is an aryl, aralkyl, or heterocyclic group which may have alkyl, alkoxy, dialkylamino, chloro- or bromo-substituents, or is an alkyl or cycloalkyl group or their chloro or bromo substituents. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US685696XA | 1948-11-23 | 1948-11-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB685696A true GB685696A (en) | 1953-01-07 |
Family
ID=22083390
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26316/49A Expired GB685696A (en) | 1948-11-23 | 1949-10-13 | Process for the manufacture of anti-histaminic compounds |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR1015149A (en) |
GB (1) | GB685696A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7230030B2 (en) | 1998-05-12 | 2007-06-12 | Schwarz Pharma Ag | Derivatives of 3,3-diphenylpropylamines |
US7989654B2 (en) | 2003-04-08 | 2011-08-02 | Ucb Pharma Gmbh | High purity bases of 3,3-diphenylpropylamino monoesters |
-
1949
- 1949-10-13 GB GB26316/49A patent/GB685696A/en not_active Expired
- 1949-10-14 FR FR1015149D patent/FR1015149A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7230030B2 (en) | 1998-05-12 | 2007-06-12 | Schwarz Pharma Ag | Derivatives of 3,3-diphenylpropylamines |
US7384980B2 (en) | 1998-05-12 | 2008-06-10 | Schwarz Pharma Ag | Derivatives of 3,3-diphenylpropylamines |
US7855230B2 (en) | 1998-05-12 | 2010-12-21 | Ucb Pharma Gmbh | Derivatives of 3,3-diphenylpropylamines |
US7985772B2 (en) | 1998-05-12 | 2011-07-26 | Ucb Pharma Gmbh | Derivatives of 3,3-diphenylpropylamines |
US8338478B2 (en) | 1998-05-12 | 2012-12-25 | Ucb Pharma Gmbh | Derivatives of 3,3-diphenylpropylamines |
US7989654B2 (en) | 2003-04-08 | 2011-08-02 | Ucb Pharma Gmbh | High purity bases of 3,3-diphenylpropylamino monoesters |
Also Published As
Publication number | Publication date |
---|---|
FR1015149A (en) | 1952-08-27 |
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