GB666778A - Pyridyldialkylaminoalkyl acetonitriles and their piperidino and morpholino-analogues - Google Patents
Pyridyldialkylaminoalkyl acetonitriles and their piperidino and morpholino-analoguesInfo
- Publication number
- GB666778A GB666778A GB25947/48A GB2594748A GB666778A GB 666778 A GB666778 A GB 666778A GB 25947/48 A GB25947/48 A GB 25947/48A GB 2594748 A GB2594748 A GB 2594748A GB 666778 A GB666778 A GB 666778A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethylaminoethyl
- pyridyl
- pyridylacetonitrile
- halide
- 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
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 title abstract 2
- -1 cycloaliphatic Chemical group 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 abstract 2
- ZJWDEMJHVZBLFG-UHFFFAOYSA-N 1,2-dichloro-n,n-diethylethanamine Chemical compound CCN(CC)C(Cl)CCl ZJWDEMJHVZBLFG-UHFFFAOYSA-N 0.000 abstract 1
- JRPNCILONFCLQX-UHFFFAOYSA-N 1,2-dichloro-n,n-dimethylethanamine Chemical compound CN(C)C(Cl)CCl JRPNCILONFCLQX-UHFFFAOYSA-N 0.000 abstract 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- CAXNYFPECZCGFK-UHFFFAOYSA-N 2-phenyl-2-pyridin-2-ylacetonitrile Chemical compound C=1C=CC=NC=1C(C#N)C1=CC=CC=C1 CAXNYFPECZCGFK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- QRNZDUNTKDCVAB-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-2-ylbutanenitrile Chemical compound CN(C(C)C(C#N)C1=NC=CC=C1)C QRNZDUNTKDCVAB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 150000007960 acetonitrile Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Pyridyl aminonitriles of formula <FORM:0666778/IV (b)/1> where R1 is aralkyl, aryl, cycloaliphatic, or heterocyclic, all of which may be substituted by chlorine, bromine, lower alkyl or alkoxy groups, R2 is lower alkyl or hydrogen, R3 is a di-(lower alkyl) amino group, piperidino or morpholino, and R is an alkylene group of 2-4 carbon atoms, are prepared by condensing a substituted acetonitrile with a pyridyl or alkylpyridyl halide, and with a di-(lower-alkyl) aminoalkyl, piperidinoalkyl or morpholinoalkyl halide all together or successively in either order. The pyridylaminonitriles when heated with acids lose the cyano group to give pyridylamines. In the examples, 2 - pyridylphenylacetonitrile, prepared from a 2-pyridyl halide and phenylacetonitrile, is condensed in presence of sodamide with (1) b -dimethylaminoethyl chloride; (2) b -diethylaminoethyl chloride to give the corresponding a -phenyl-a -(b 1-dialkylaminoethyl)-2-pyridylacetonitrile. Ten other examples are given illustrating the preparation of, for example, a - (2 - thienyl) - a - (b 1 - dimethylaminoethyl) - 2 - pyridylacetonitrile, a - (p - methoxyphenyl) - a - b (1-dimethylaminoethyl)-2 - pyridylacetonitrile, a - (p - bromophenyl) - a - (b 1 - dimethylaminoethyl) - 2 - pyridylaceto-nitrile, and b -cyclohexyl-a -(b 1-dimethylaminoethyl)-a -(2-pyridyl) propionitrile. The Specification as open to inspection under Sect. 91 comprises the additional compound a - (2 - furyl) - a - (b - dimethylaminoethyl) - 2 - pyridylacetonitrile, a ,a - bis - (2 - pyridyl) - a - (N,N - dimethylaminoethyl) octonitrile and other aminonitriles in which the group R1 is 2-thiazyl, 2-pyrimidyl, and 5-chloro-2-thienyl. It is also stated that R1 may be alkyl, and additional solvents and catalysts are specified as suitable for the reaction. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US666778XA | 1947-10-13 | 1947-10-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB666778A true GB666778A (en) | 1952-02-20 |
Family
ID=22070999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25947/48A Expired GB666778A (en) | 1947-10-13 | 1948-10-05 | Pyridyldialkylaminoalkyl acetonitriles and their piperidino and morpholino-analogues |
Country Status (3)
| Country | Link |
|---|---|
| FR (1) | FR1013690A (en) |
| GB (1) | GB666778A (en) |
| NL (1) | NL70757C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029189A (en) * | 1962-04-10 | S-aryl-z-mno-x-qxazolibinones | ||
| EP0027412A1 (en) * | 1979-10-11 | 1981-04-22 | Sanofi S.A. | Pyridine derivatives, process for their preparation and medicaments containing them |
| EP0105458A2 (en) * | 1982-09-30 | 1984-04-18 | Fujisawa Pharmaceutical Co., Ltd. | Alpha-aryl-alpha-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same |
| US4783537A (en) * | 1985-11-13 | 1988-11-08 | Pennwalt Corporation | α-(aminoalkyl)-arylacetic acid derivatives |
| US4847301A (en) * | 1985-11-13 | 1989-07-11 | Pennwalt Corporation | Methods of use of α-(aminoalkyl)-arylacetic acid derivatives |
-
0
- NL NL70757D patent/NL70757C/xx active
-
1948
- 1948-10-05 GB GB25947/48A patent/GB666778A/en not_active Expired
- 1948-10-08 FR FR1013690D patent/FR1013690A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029189A (en) * | 1962-04-10 | S-aryl-z-mno-x-qxazolibinones | ||
| EP0027412A1 (en) * | 1979-10-11 | 1981-04-22 | Sanofi S.A. | Pyridine derivatives, process for their preparation and medicaments containing them |
| EP0105458A2 (en) * | 1982-09-30 | 1984-04-18 | Fujisawa Pharmaceutical Co., Ltd. | Alpha-aryl-alpha-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same |
| EP0105458A3 (en) * | 1982-09-30 | 1985-11-27 | Fujisawa Pharmaceutical Co., Ltd. | Alpha-aryl-alpha-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same |
| US4564621A (en) * | 1982-09-30 | 1986-01-14 | Fujisawa Pharmaceutical Co., Ltd. | α-Aryl-α-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same |
| US4783537A (en) * | 1985-11-13 | 1988-11-08 | Pennwalt Corporation | α-(aminoalkyl)-arylacetic acid derivatives |
| US4847301A (en) * | 1985-11-13 | 1989-07-11 | Pennwalt Corporation | Methods of use of α-(aminoalkyl)-arylacetic acid derivatives |
| AU596805B2 (en) * | 1985-11-13 | 1990-05-17 | Fisons Corporation | Alpha-(aminoalkyl)-arylacetic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1013690A (en) | 1952-08-01 |
| NL70757C (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE39835B1 (en) | Oxepin derivatives | |
| GB1494943A (en) | 1,1-diaryl-1-oxadiazol-alkylamines | |
| GB666778A (en) | Pyridyldialkylaminoalkyl acetonitriles and their piperidino and morpholino-analogues | |
| SE7602144L (en) | QUATER IMIDAZOLIUM ASSOCIATIONS | |
| Miller et al. | The Synthesis of Some 6-Substituted-2-thiouracils1 | |
| GB1492528A (en) | Pyrazinyl piperazine derivatives | |
| GB1230675A (en) | ||
| GB676812A (en) | Improvements in or relating to piperazine derivatives | |
| IE43730L (en) | Pyridine carboxamides. | |
| GB1252479A (en) | ||
| US3536723A (en) | P - (2 - alkyloxy - benzoyl) - aminobenzoates of n - dialkylamine - alkyl and their quaternary salts | |
| US3624085A (en) | Pyrazinylthioamides | |
| US2489777A (en) | Alpha-aminopyridine antifflstaminic | |
| DE2501286A1 (en) | NEW THIOAMIDES | |
| KR840001106B1 (en) | Method for preparing pyridine derivative | |
| SE8301785L (en) | SET TO MAKE 2-THIOPHENIC ACETIC ACID DERIVATIVES AND INTERMEDIATES REQUIRED FOR THEIR PREPARATION | |
| US2655503A (en) | Quaternary salts of y-stilbazolines | |
| GB704416A (en) | Improvements in or relating to thiaxanthones and the preparation thereof | |
| GB1120082A (en) | Improvements in or relating to acetaldehyde diacylates and the manufacture thereof | |
| JPS57106663A (en) | 1,4-disubstituted piperazine derivative and its preparation | |
| ES478219A1 (en) | Disubstituted piperazines | |
| GB608208A (en) | Process for the preparation of phenthiazine derivatives | |
| GB1329493A (en) | N-alkyl-pyridyl-furamides | |
| GB631755A (en) | Alkyl and di-alkylaminoalkyl and analogous pyridazones | |
| GB923357A (en) | Cinnamamide derivatives and process for their preparation |