GB999391A - Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture - Google Patents
Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufactureInfo
- Publication number
- GB999391A GB999391A GB28117/61A GB2811761A GB999391A GB 999391 A GB999391 A GB 999391A GB 28117/61 A GB28117/61 A GB 28117/61A GB 2811761 A GB2811761 A GB 2811761A GB 999391 A GB999391 A GB 999391A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- salts
- sulphonic acid
- epi
- reserpate
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of general formula <FORM:0999391/C2/1> in which R1 and R2 are alkyl (1-5 C), and X is hydroxy, chlorine, bromine, iodine or OR2; and their preparation by reacting a compound BrCR1(COOR2)2 with an alkali metal benzylate to form the diesters I (X = OR2), which are saponified with an alcoholic solution of an alkali metal hydroxide to the ester-acids I (X = ON), from which the halides are obtainable by known methods.ALSO:The invention comprises methyl 18-epi-OR-reserpates, in which R is methyl, ethyl, n-propyl or isopropyl, and their acid addition salts; and the preparation of these compounds by subjecting a methyl reserpate, esterified in the 18 position with an organic sulphonic acid, to alcoholysis with an alcohol ROH and, if desired, converting the resulting bases into salts or the resulting salts into bases. A tertiary amine catalyst is usually used for the alcoholysis reaction. The organic radical of the sulphonic acid ester starting material may be lower alkyl, unsubstituted phenyl or a phenyl radical substituted with, for example, halogen atoms or nitro, carboxyl, carbalkoxy, carbamyl, cyano or methyl groups; these sulphonic acid esters are prepared by reacting a methyl reserpate with the appropriate sulphonic acid halide in the presence of a base such as pyridine or collidine. Pharmaceutical preparations comprise the methyl 18-epi-OR-reserpates and their salts, which are sedatives, tranquillizers, antifibrillatory agents and local anaesthetics, together with a pharmaceutically suitable carrier. They may be in forms suitable for enteral or parenteral administration, e.g. tablets, dragees, capsules, solutions, suspensions or emulsions. Veterinary preparations, e.g. in the form of animal feedstuffs, are also mentioned. Salts specified include those with ascorbic, salicylic and p-aminosalicylic acids, methionine, tryptophan, lysine and arginine. Specifications 999,394 and 999,397 are referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4691160A | 1960-08-02 | 1960-08-02 | |
| US7349060A | 1960-12-05 | 1960-12-05 | |
| US11032061A | 1961-05-16 | 1961-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB999391A true GB999391A (en) | 1965-07-28 |
Family
ID=27367016
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49912/64A Expired GB999398A (en) | 1960-08-02 | 1961-08-02 | New esters of the yohimbane series and process for their manufacture |
| GB46383/64A Expired GB999397A (en) | 1960-08-02 | 1961-08-02 | New esters of the vohimbane series and process for their manufacture |
| GB52687/64A Expired GB999399A (en) | 1960-08-02 | 1961-08-02 | New esters of the yohimbane series and process for their manufacture |
| GB28119/61A Expired GB999393A (en) | 1960-08-02 | 1961-08-02 | New ethers of the yohimbane series and process for their manufacture |
| GB28117/61A Expired GB999391A (en) | 1960-08-02 | 1961-08-02 | Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture |
| GB28118/61A Expired GB999392A (en) | 1960-08-02 | 1961-08-02 | New ethers of the yohimbane series and process for their manufacture |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49912/64A Expired GB999398A (en) | 1960-08-02 | 1961-08-02 | New esters of the yohimbane series and process for their manufacture |
| GB46383/64A Expired GB999397A (en) | 1960-08-02 | 1961-08-02 | New esters of the vohimbane series and process for their manufacture |
| GB52687/64A Expired GB999399A (en) | 1960-08-02 | 1961-08-02 | New esters of the yohimbane series and process for their manufacture |
| GB28119/61A Expired GB999393A (en) | 1960-08-02 | 1961-08-02 | New ethers of the yohimbane series and process for their manufacture |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28118/61A Expired GB999392A (en) | 1960-08-02 | 1961-08-02 | New ethers of the yohimbane series and process for their manufacture |
Country Status (6)
| Country | Link |
|---|---|
| AT (7) | AT249273B (en) |
| CH (8) | CH407145A (en) |
| ES (3) | ES269516A1 (en) |
| GB (6) | GB999398A (en) |
| NL (1) | NL139529B (en) |
| SE (7) | SE301478B (en) |
-
1961
- 1961-07-12 CH CH308665A patent/CH407145A/en unknown
- 1961-07-12 CH CH308565A patent/CH407144A/en unknown
- 1961-07-12 CH CH819361A patent/CH410969A/en unknown
- 1961-07-12 CH CH819061A patent/CH398627A/en unknown
- 1961-07-12 CH CH819161A patent/CH398628A/en unknown
- 1961-07-12 CH CH819261A patent/CH416658A/en unknown
- 1961-07-12 CH CH308765A patent/CH407146A/en unknown
- 1961-07-12 CH CH308465A patent/CH407143A/en unknown
- 1961-08-01 AT AT594861A patent/AT249273B/en active
- 1961-08-01 AT AT100262A patent/AT252461B/en active
- 1961-08-01 AT AT100362A patent/AT252462B/en active
- 1961-08-01 AT AT594961A patent/AT249274B/en active
- 1961-08-01 AT AT100162A patent/AT252460B/en active
- 1961-08-01 NL NL61267779A patent/NL139529B/en unknown
- 1961-08-01 AT AT887662A patent/AT252463B/en active
- 1961-08-01 AT AT100062A patent/AT252459B/en active
- 1961-08-02 ES ES0269516A patent/ES269516A1/en not_active Expired
- 1961-08-02 SE SE7892/61A patent/SE301478B/xx unknown
- 1961-08-02 GB GB49912/64A patent/GB999398A/en not_active Expired
- 1961-08-02 GB GB46383/64A patent/GB999397A/en not_active Expired
- 1961-08-02 GB GB52687/64A patent/GB999399A/en not_active Expired
- 1961-08-02 GB GB28119/61A patent/GB999393A/en not_active Expired
- 1961-08-02 ES ES0269514A patent/ES269514A1/en not_active Expired
- 1961-08-02 ES ES0269515A patent/ES269515A1/en not_active Expired
- 1961-08-02 SE SE7893/61A patent/SE301650B/xx unknown
- 1961-08-02 GB GB28117/61A patent/GB999391A/en not_active Expired
- 1961-08-02 GB GB28118/61A patent/GB999392A/en not_active Expired
-
1965
- 1965-06-08 SE SE7479/65A patent/SE301484B/xx unknown
- 1965-06-08 SE SE7482/65A patent/SE301487B/xx unknown
- 1965-06-08 SE SE7481/65A patent/SE301486B/xx unknown
- 1965-06-08 SE SE7478/65A patent/SE301321B/xx unknown
- 1965-06-08 SE SE7480/65A patent/SE301485B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE301321B (en) | 1968-06-04 |
| AT252460B (en) | 1967-02-27 |
| CH407146A (en) | 1966-02-15 |
| GB999393A (en) | 1965-07-28 |
| CH407145A (en) | 1966-02-15 |
| CH398627A (en) | 1966-03-15 |
| ES269514A1 (en) | 1962-04-16 |
| CH407144A (en) | 1966-02-15 |
| AT252459B (en) | 1967-02-27 |
| SE301486B (en) | 1968-06-10 |
| GB999398A (en) | 1965-07-28 |
| SE301478B (en) | 1968-06-10 |
| GB999397A (en) | 1965-07-28 |
| AT252461B (en) | 1967-02-27 |
| CH398628A (en) | 1966-03-15 |
| SE301487B (en) | 1968-06-10 |
| NL139529B (en) | 1973-08-15 |
| ES269515A1 (en) | 1962-04-16 |
| SE301485B (en) | 1968-06-10 |
| SE301484B (en) | 1968-06-10 |
| AT249273B (en) | 1966-09-12 |
| GB999392A (en) | 1965-07-28 |
| AT252462B (en) | 1967-02-27 |
| AT252463B (en) | 1967-02-27 |
| ES269516A1 (en) | 1962-04-16 |
| AT249274B (en) | 1966-09-12 |
| CH416658A (en) | 1966-07-15 |
| SE301650B (en) | 1968-06-17 |
| CH407143A (en) | 1966-02-15 |
| GB999399A (en) | 1965-07-28 |
| CH410969A (en) | 1966-04-15 |
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