GB1109924A - Novel substituted diphenylalkyl amines and a process for the manufacture thereof - Google Patents
Novel substituted diphenylalkyl amines and a process for the manufacture thereofInfo
- Publication number
- GB1109924A GB1109924A GB50543/65A GB5054365A GB1109924A GB 1109924 A GB1109924 A GB 1109924A GB 50543/65 A GB50543/65 A GB 50543/65A GB 5054365 A GB5054365 A GB 5054365A GB 1109924 A GB1109924 A GB 1109924A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- symbol
- symbols
- phenyl group
- phenyl
- 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
- 150000001412 amines Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- -1 aralkyl cyanide Chemical compound 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 230000002353 algacidal effect Effects 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds of the general formula <FORM:1109924/C2/1> wherein one of the symbols R1 and R2 represents a phenyl group carrying 1 to 3 halogen atoms and the other symbol represents a phenyl group carrying 1 to 3 halogen, hydroxyl, nitro, trifluoromethyl, lower-alkyl or lower alkoxy substituents, the symbol R3 represents a lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, halo-substituted lower alkanoyl or halo-substituted phenyl-(lower alkanoyl) group or a group of the formula B-R2 and wherein the symbols A and B (of which two of the latter may be present according to the value of R3 if present) each represent a straight chain or branched chain alkylene group containing up to 5 carbon atoms which may be substituted at the carbon atom in the a -position to the phenyl group by a hydroxyl group and wherein at least one of the phenyl groups R1 and R2 is linked with the nitrogen atom through at least 2 carbon atoms (except those compounds in which the symbols R1 and R2 each represent a 3,4-dihalo-phenyl group, the symbol R3 is absent and the symbols A and B each represent the ethylene group and those compounds in which the symbol R1 represents a monohalophenyl group, the symbol R2 represents a 3,4-dialkoxy-phenyl group, the symbol R3 is either absent or represents a lower alkyl group and the symbols A and B each represent an unsubstituted alkylene group) are obtained in a process which comprises either subjecting an aralkyl cyanide of the formula R2-X-CN to a hydrogenation-cum-condensation or aralkylating ammonia or an amine of the formula R1-A1-NH-[H or R3] with an aralkylating agent having the labile group -B1R2 or halogenating a compound of the formula <FORM:1109924/C2/2> and in either case where required, reducing any carbonyl group or groups present to a hydroxymethylene group or groups, splitting off any R3 group present if desired, introducing the R3 group if desired and/or converting the product into an acid addition or quaternary ammonium salt if desired; in which formulae the symbol X represents an alkylene group containing up to 4 carbon atoms, the symbols A1 and B1 have the significance according to the symbols A and B or represent an alkylene group containing up to 4 carbon atoms which is linked with the respective phenyl group by means of a carbonyl group, the symbol R11 represents an unsubstituted phenyl group or a phenyl group carrying 1 or 2 halogen substituents and the symbol R21 represents an unsubstituted-phenyl group or phenyl group carrying 1 or 2 halogen, hydroxyl, nitro, trifluoromethyl, lower alkyl or lower alkoxy substituents. Pharmaceutical compositions having fungicidal, antiprotozoal, algicidal, bactericidal and anthelmintic activities and containing the above compounds are administered enterally, parenterally or topically.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB50543/65A GB1109924A (en) | 1965-11-29 | 1965-11-29 | Novel substituted diphenylalkyl amines and a process for the manufacture thereof |
| DE19661543672 DE1543672A1 (en) | 1965-11-29 | 1966-11-10 | Process for the preparation of substituted diphenylalkylamines |
| BR18478766A BR6684787D0 (en) | 1965-11-29 | 1966-11-23 | PROCESS FOR THE PREPARATION OF REPLACED DIPHENYL-ALCOHYL-AMINES |
| FR84923A FR7001M (en) | 1965-11-29 | 1966-11-25 | |
| BE690183D BE690183A (en) | 1965-11-29 | 1966-11-25 | |
| ES333873A ES333873A1 (en) | 1965-11-29 | 1966-11-28 | Novel substituted diphenylalkyl amines and a process for the manufacture thereof |
| NL6616723A NL6616723A (en) | 1965-11-29 | 1966-11-28 | |
| FR85148A FR1505657A (en) | 1965-11-29 | 1966-11-28 | Process for the preparation of substituted diphenylalkylamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB50543/65A GB1109924A (en) | 1965-11-29 | 1965-11-29 | Novel substituted diphenylalkyl amines and a process for the manufacture thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1109924A true GB1109924A (en) | 1968-04-18 |
Family
ID=10456293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB50543/65A Expired GB1109924A (en) | 1965-11-29 | 1965-11-29 | Novel substituted diphenylalkyl amines and a process for the manufacture thereof |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE690183A (en) |
| BR (1) | BR6684787D0 (en) |
| DE (1) | DE1543672A1 (en) |
| ES (1) | ES333873A1 (en) |
| FR (2) | FR7001M (en) |
| GB (1) | GB1109924A (en) |
| NL (1) | NL6616723A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4585796A (en) * | 1982-08-10 | 1986-04-29 | Hoffmann-La Roche Inc. | Novel phenethanolamines |
| FR2597475A1 (en) * | 1986-01-29 | 1987-10-23 | Solvay | USE OF AROMATIC AND HETEROCYCLIC AMINES AS MEDICAMENTS AND AGROCHEMICAL PRODUCTS. |
| JPH0334958A (en) * | 1989-06-30 | 1991-02-14 | Tookemu Prod:Kk | 4,4'-difluorodibenzylamine and production thereof |
| US5017619A (en) * | 1985-04-16 | 1991-05-21 | Hoffmann-La Roche Inc. | Phenethanolamine derivatives |
| US5981599A (en) * | 1996-05-01 | 1999-11-09 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor active compounds |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6087346A (en) * | 1993-06-23 | 2000-07-11 | Cambridge Neuroscience, Inc. | Sigma receptor ligands and the use thereof |
| US6211244B1 (en) | 1994-10-21 | 2001-04-03 | Nps Pharmaceuticals, Inc. | Calcium receptor-active compounds |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| WO2010059711A1 (en) * | 2008-11-18 | 2010-05-27 | Wisconsin Alumni Research Foundation | Sigma-1 receptor ligands and methods of use |
| CN113735715A (en) * | 2021-10-12 | 2021-12-03 | 山东金城柯瑞化学有限公司 | Bis (2, 4-dichlorophenethyl) amine hydrochloride and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022321A1 (en) * | 1979-07-10 | 1981-01-14 | Beecham Group Plc | Benzene derivatives, their preparation and use in pharmaceutical compositions |
-
1965
- 1965-11-29 GB GB50543/65A patent/GB1109924A/en not_active Expired
-
1966
- 1966-11-10 DE DE19661543672 patent/DE1543672A1/en active Pending
- 1966-11-23 BR BR18478766A patent/BR6684787D0/en unknown
- 1966-11-25 FR FR84923A patent/FR7001M/fr not_active Expired
- 1966-11-25 BE BE690183D patent/BE690183A/xx unknown
- 1966-11-28 FR FR85148A patent/FR1505657A/en not_active Expired
- 1966-11-28 ES ES333873A patent/ES333873A1/en not_active Expired
- 1966-11-28 NL NL6616723A patent/NL6616723A/xx unknown
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4585796A (en) * | 1982-08-10 | 1986-04-29 | Hoffmann-La Roche Inc. | Novel phenethanolamines |
| US5017619A (en) * | 1985-04-16 | 1991-05-21 | Hoffmann-La Roche Inc. | Phenethanolamine derivatives |
| FR2597475A1 (en) * | 1986-01-29 | 1987-10-23 | Solvay | USE OF AROMATIC AND HETEROCYCLIC AMINES AS MEDICAMENTS AND AGROCHEMICAL PRODUCTS. |
| BE1001550A5 (en) * | 1986-01-29 | 1989-12-05 | Sandoz Sa | USE OF AROMATIC AND HETEROCYCLIC AMINES AS MEDICINES AND AGROCHEMICALS. |
| JPH0334958A (en) * | 1989-06-30 | 1991-02-14 | Tookemu Prod:Kk | 4,4'-difluorodibenzylamine and production thereof |
| JP2727359B2 (en) | 1989-06-30 | 1998-03-11 | 株式会社トーケムプロダクツ | 4,4'-Difluorodibenzylamine and process for producing the same |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6087346A (en) * | 1993-06-23 | 2000-07-11 | Cambridge Neuroscience, Inc. | Sigma receptor ligands and the use thereof |
| US6211244B1 (en) | 1994-10-21 | 2001-04-03 | Nps Pharmaceuticals, Inc. | Calcium receptor-active compounds |
| US5981599A (en) * | 1996-05-01 | 1999-11-09 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor active compounds |
| US6342532B1 (en) | 1996-05-01 | 2002-01-29 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor active compounds |
| US6710088B2 (en) | 1996-05-01 | 2004-03-23 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| WO2010059711A1 (en) * | 2008-11-18 | 2010-05-27 | Wisconsin Alumni Research Foundation | Sigma-1 receptor ligands and methods of use |
| US8349898B2 (en) | 2008-11-18 | 2013-01-08 | Wisconsin Alumni Research Foundation | Sigma-1 receptor ligands and methods of use |
| US8946302B2 (en) | 2008-11-18 | 2015-02-03 | Wisconsin Alumni Research Foundation | Selective sigma-1 receptor ligands |
| CN113735715A (en) * | 2021-10-12 | 2021-12-03 | 山东金城柯瑞化学有限公司 | Bis (2, 4-dichlorophenethyl) amine hydrochloride and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1543672A1 (en) | 1969-09-18 |
| BR6684787D0 (en) | 1973-12-04 |
| BE690183A (en) | 1967-05-25 |
| NL6616723A (en) | 1967-05-30 |
| FR1505657A (en) | 1967-12-15 |
| ES333873A1 (en) | 1968-03-01 |
| FR7001M (en) | 1969-06-02 |
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