GB762256A - Tertiary-amino-substituted compounds of the tropane and granatanine series - Google Patents
Tertiary-amino-substituted compounds of the tropane and granatanine seriesInfo
- Publication number
- GB762256A GB762256A GB26128/54A GB2612854A GB762256A GB 762256 A GB762256 A GB 762256A GB 26128/54 A GB26128/54 A GB 26128/54A GB 2612854 A GB2612854 A GB 2612854A GB 762256 A GB762256 A GB 762256A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compounds
- mono
- acid
- 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
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises: (a) compounds of the general formul <FORM:0762256/IV(b)/1> and <FORM:0762256/IV(b)/2> wherein Y represents NH, N-(lower-alkyl), N-(lower-alkanoyl), N-(mono-carbocyclic aroyl), N - (lower - alkylcarbamyl), N - (lower - alkenylcarbamyl), N - (mono - carbocyclic arylcarbamyl), N - (lower - alkylthiocarbamyl), N-(lower - alkenylthiocarbamyl), N - (mono-carbocyclic arylthiocarbamyl), O or S, n is an integer from 2 to 6, m is 1 or 2, R represents a lower-alkyl, mono-carbocyclic aryl-lower-alkyl or mono-carbocyclic aryl group, and N=B represents a di-lower-alkylamino, 1-pyrrolidyl, 1-piperidyl, 4-morpholinyl or mono-carbocyclic aryl-lower-alkylamino group (Y and N=B being attached to different carbon atoms of the CnH2n bridge, the mono-carbocyclic aryl groups in all cases including phenyl or phenyl substituted by halogen or by lower-alkyl, loweralkoxy or methylenedioxy groups, and the qualification "lower" denoting that the groups in question contain 1-6 carbon atoms), and their acid addition and quaternary ammonium salts; (b) the preparation of compounds of formula I in which Y is NH by condensing a compound of the formula <FORM:0762256/IV(b)/3> with a tertiary-amino lower-alkylamine H2N-CnH2n-N=B and reducing the unsaturated compound so formed; (c) the preparation of compounds of formula I in which Y is N-acyl (as defined above) by treating the products of (b) with an acylating agent (e.g. an acid, acid anhydride, acid halide, isocyanate or isothiocyanate); (d) the preparation of compounds of formula I in which Y is N-(lower-alkyl) by reducing compounds in which Y is N-(lower-alkanoyl) by means of lithium aluminium hydride; (e) the preparation of compounds of formula I in which Y is N(CH3) (except those in which n=2 and N=B is a mono-carbocyclic aryl-lower-alkylamino group) or of compounds of formula I(a) by heating the products of (b) with formaldehyde and formic acid; (f) the preparation of compounds of formula I in which Y is O or S by reacting a compound of the formula <FORM:0762256/IV(b)/4> with a compound of the formula X1-CnH2n-N=B, where one of X and X1 represents halogen and the other OM or SM, M being an alkali metal. Processes (b) and (f) may be followed by treatment of the resulting base with an acid or a quaternizing agent. The reduction step in process (b) may be effected simultaneously with the condensation, by catalytic hydrogenation, or subsequently thereto, either by catalytic hydrogenation, yielding almost exclusively the stereoisomer corresponding to the normal tropane series, or chemically (e.g. with sodium and a lower alkanol), yielding a mixture of stereoisomers, which can be separated by fractional crystallization of their N-(substituted thiocarbamyl) derivatives. Examples illustrate various combinations of the following meanings of the symbols in formul I and I(a): Y=NH, N(CH3), O, S, N(CSNHC6H5), N(CSNHCH2CH= CH2), N(CSNHC2H5), N(CSNHC6H4OC2H5-4), N(COCH3), N(C2H5), N(COCH2CH3), N(C3H7), N(COCH2CH2CH3), N(C4H9) and N(CHO); m = 1 and 2; n = 2, 3 and 4; R = CH3,C6H5CH2, 4-CH3OC6H4CH2, 2,3-(CH3O)2C6H3CH2, 3,4-CH2O2C6H3CH2, 2- and 4-ClC6H4CH2 and C6H5; N = B = N(C2H5)2, N(CH3)2, NC5H10, NC4H8, NC4H8O, N(CH3)(C6H5) and N(C2H5) (C6H5); lower-alkyl in I(a) = CH3 and C2H5. Salts are prepared in some cases by treatment of the bases with hydrochloric, hydrobromic, picric and perchloric acids, methyl bromide and iodide and ethyl iodide (others being listed). The products (especially the quaternary ammonium salts) are useful as ganglionic blocking agents. Starting materials. Ketones of formula III are prepared by condensing succinic or glutaric dialdehyde with a primary amine (H2NR) and an acetone dicarboxylic acid ester, followed by hydrolysis and decarboxylation. The succinic dialdehyde is conveniently prepared in situ by acid treatment of 2 : 5-diethoxytetrahydrofuran and the glutaric dialdehyde by heating its dioxime with sodium nitrite in hydrochloric acid. The preparation of 8-benzylnortropanone is described in detail. Alcoholates and halides of formula V (X = OM or halogen) are obtainable by reducing the keto group in compounds III and converting the resulting OH group to OM or replacing it by halogen.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US762256XA | 1953-09-17 | 1953-09-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB762256A true GB762256A (en) | 1956-11-28 |
Family
ID=22130692
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26128/54A Expired GB762256A (en) | 1953-09-17 | 1954-09-09 | Tertiary-amino-substituted compounds of the tropane and granatanine series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB762256A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0122580A1 (en) * | 1983-04-14 | 1984-10-24 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyrimidine derivatives, their preparation and pharmaceutical compositions |
-
1954
- 1954-09-09 GB GB26128/54A patent/GB762256A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0122580A1 (en) * | 1983-04-14 | 1984-10-24 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyrimidine derivatives, their preparation and pharmaceutical compositions |
US4590270A (en) * | 1983-04-14 | 1986-05-20 | Hoffmann-La Roche Inc. | 2,4-diamino-[4-piperidinyl]pyrimidines useful as antibacterial agents, antimalarial agents, antitumors agents |
US4774249A (en) * | 1983-04-14 | 1988-09-27 | Hoffmann-La Roche Inc. | Pyrimidine derivatives for treating malaria |
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