GB1583555A - Open ring aldehyde derivatives of sandwicin and a method of producing them - Google Patents
Open ring aldehyde derivatives of sandwicin and a method of producing them Download PDFInfo
- Publication number
- GB1583555A GB1583555A GB41140/79A GB4114079A GB1583555A GB 1583555 A GB1583555 A GB 1583555A GB 41140/79 A GB41140/79 A GB 41140/79A GB 4114079 A GB4114079 A GB 4114079A GB 1583555 A GB1583555 A GB 1583555A
- Authority
- GB
- United Kingdom
- Prior art keywords
- open ring
- sandwicin
- alkali
- ring aldehyde
- chloroform
- 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
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Classifications
-
- 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
- C07D471/22—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 systems contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
PATENT SPECIFICATION
( 11) 1583555 1 t ( 21) C ( 62) ( 31) m ( 32) Uks ( 33) ( 44) ( 51) Application No 41140/79 ( 22) Filed 11 March 1977 Divided out of No 1 583 554 Convention Application No 2 611 162 Filed 17 March 1976 in Fed Rep of Germany (DE)
Complete Specification published 28 Jan 1981
INT CL 3 C 07 D 471/18; (C 07 D 471/18, 209/00, 221/00) ( 52) Index at acceptance C 2 C 136 X 213 214 21 X 247 248 250 252 259 25 Y 30 Y 350 360 362 36 Y 40 Y 623 672 AA TA ( 72) The inventors of this invention in the sense of being the actual devisers thereof within the meaning of Section 16 of the Patents Act 1949 are PETER PATT, 6720 Speyer, Im Rochschild 16 and MICHAEL SCHNEIDER, 8000 Munchen 40, Kunigudenstr 33, both citizens of the Federal Republic of Germany and both residing in the Federal Republic of Germany.
( 54) OPEN RING ALDEHYDE DERIVATIVES OF SANDWICIN AND A METHOD OF PRODUCING THEM ( 71) We, KALI-CHEMIE PHARMA GMBH, a body corporate organised under the laws of the German Federal Republic of HansBockler-Allee 20, D-3000 Hannover, German Federal Republic, do hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: -
This invention relates to open ring aldehyde derivatives of sandwicin and to a method of producing them These open ring aldehyde derivatives are intermediates for the production of the quaternary derivatives of sandwicin described and claimed in the Specification of our co-pending Patent Application No.
10521/77 (Serial No 1 583 554).
The present open ring aldehyde derivatives of sandwicin have the general formula I; CH 3 ' C = O in which R is a straight-chaim or branched alkyl radical containing up to 5 carbon atoms, preferably a methyl, ethyl, or propyl radical.
These compounds are prepared by reacting sandwicin with an alkyl halide in which the alkyl radical is a straight chain or branched alkyl radical containing up to 5 carbon atoms, and converting the resulting sandwicinium halide by treatment with an alkali into the corresponding open ring aminoaldehyde of the above general formula I.
In this method, the starting substances are reacted in equimolar amounts, but the alkyl halide may be used in excess, in which case it simultaneously serves the function of a solvent Suitable solvents in which the method may be performed also include for example, acetonitrile, chloroform and dimethyl formamide.
The open ring aminoaldehyde is obtained either by reacting the sandwicinium halide with a 10 % aqueous sodium hydroxide solution or by reacting it with another aqueous alkali solution, such as for example, a solution of sodium bicarbonate or of sodium carbonate It is expedient to work in the presence of a suitable extraction medium which may be any inert water-immiscible solvent, such as chloroform on diethyl ether, in which the base has adequate solubility After the extraction medium has been distilled off, preferably by vacuum distillation, the base is obtained in an amorphous form.
The base produced in this manner (i e an open ring aminoaldehyde) can then be reacted with a physiologically compatible inorganic or organic acid, preferably tartaric acid, oxalic acid, citric acid or phosphoric acid to produce the corresponding quaternary derivative as described in the Specification of our aforesaid co-pending Patent Application.
The invention will now be illustrated by the following Example:
Example 1.
A: N-methyl-sandwicinium iodide 12.0 g of sandwicin are heated under reflux for about 7 to 9 hours with 12 0 ml of 2 1,583,555 2 methyl iodide in 500 ml of acetonitrile and then evaporated to dryness 16 0 g of Nmethyl-sandwicinium iodide in the form of an amorphous yellow product are obtained.
Yield: 93 % of theory.
B: Open ring aldehyde base 16.0 g of N-methyl-sandwicinium iodide are suspended in 500 ml of water, 12 0 ml of % sodium hydroxide solution are added, and the mixture is stirred for 30 minutes with 1000 ml of chloroform The chloroform phases are united and dried over sodium sulphate An amorphous residue of 11 5 g of open ring aldehyde base of formula I (R=CHI) is obtained.
Yield: quantitative Example 2.
A: N-propyl-sandwicinium bromide 22.0 g of sandwicin are heated under reflux for about 7 to 9 hours with 20 ml of n-propyl bromide in 1000 ml of acetonitrile, whereby a light-coloured precipitate is formed.
where R is a straight-chain or branched alkyl radical containing up to 5 carbon atoms.
2 An open ring aldehyde derivative of sandwicin of the general formula defined in
Claims (1)
- Claim 1 substantially as hereinbefore des-cribed in either of the foregoing Examples.3 A method of producing an open ring aldehyde derivative of sandwicin of the general formula defined in Claim 1, wherein sandwicin is reacted with an alkyl halide in which the alkyl radical is a straight chain or branched alkyl radical containing up to 5 carbon atoms, and wherein the resulting sandwicinium halide is converted into the open ring aldehyde of the formula defined in Claim 1 by treatment with an alkali.4 A method as claimed in Claim 3, wherein the reaction with alkyl halide is conducted in a solvent.A method as claimed in Claim 3, wherein the alkyl halide is present in excess and serves as a solvent.6 A method as claimed in any one of Claims The precipitate is sucked off, washed with acetonitrile, and dried at 50 C 20 8 g of Npropyl-sandwicinium bromide, MP 314316 o C are obtained.Yield: 69 % of theory.B: Open ring aldehyde base 20.8 g of N-propyl-sandwicinium bromide are suspended in 200 ml of water, 20 ml of % sodium hydroxide solution are added, and the mixture is stirred with 200 ml of chloroform for 30 minutes After separation of the chloroform phase, the product is stirred twice with 200 ml of chloroform The chloroform phases are united, dried over sodium sulphate, and evaporated in vacuo.Residue: 16 2 g ot amorphous aldehyde base of formula I (R=C 3 H 7) Yield: quantitative.WHAT WE CLAIM IS:1 An open ring aldehyde derivative of sandwicin of the general formula 3 to 5, wherein the alkali is in the form of an aqueous alkali solution.7 A method as claimed in Claim 6, wherein the alkali is a 10 % aqueous sodium hydroxide solution.8 A method as claimed in Claims 6 or 7, wherein the treatment with alkali is carried out in the presence of an inert water-immiscible solvent as an extraction medium.9 A method of producing an open ring aldehyde derivative of sandwicin of the general formula defined in Claim 1 substantially as hereinbefore described in either of the foregoing Examples.TREGEAR, THIEMANN & BLEACH, Chartered Patent Agents, Enterprise House, Isambard Brunel Road, Portsmouth PO 1 2 AN -and49-51, Bedford Row, London WC 1 V 6 RL.Printed for Her Majesty's Stationery Office by the Courier Press, Leamington Spa, 1981.Published by the Patent Office, 25 Southampton Buildings, London, WC 2 A l AY, from which copies may be obtained.1,583,555
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762611162 DE2611162A1 (en) | 1976-03-17 | 1976-03-17 | NEW QUARTERLY DERIVATIVES OF SANDWICIN AND THE METHOD FOR THEIR PRODUCTION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1583555A true GB1583555A (en) | 1981-01-28 |
Family
ID=5972662
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB41140/79A Expired GB1583555A (en) | 1976-03-17 | 1977-03-11 | Open ring aldehyde derivatives of sandwicin and a method of producing them |
| GB10521/77A Expired GB1583554A (en) | 1976-03-17 | 1977-03-11 | Quaternary derivatives of sandwicin and a method of producing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10521/77A Expired GB1583554A (en) | 1976-03-17 | 1977-03-11 | Quaternary derivatives of sandwicin and a method of producing them |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS52113988A (en) |
| AR (1) | AR211567A1 (en) |
| AT (1) | AT353986B (en) |
| BE (1) | BE852493A (en) |
| CA (1) | CA1072959A (en) |
| CH (1) | CH631714A5 (en) |
| CS (1) | CS197287B2 (en) |
| DD (1) | DD128774A5 (en) |
| DE (1) | DE2611162A1 (en) |
| DK (1) | DK143602C (en) |
| ES (1) | ES456755A1 (en) |
| FI (1) | FI61898C (en) |
| FR (2) | FR2344557A1 (en) |
| GB (2) | GB1583555A (en) |
| GR (1) | GR62637B (en) |
| IL (1) | IL51630A (en) |
| IN (1) | IN146149B (en) |
| IT (1) | IT1084656B (en) |
| MX (1) | MX4788E (en) |
| NL (1) | NL7702609A (en) |
| NO (1) | NO146282C (en) |
| PT (1) | PT66298B (en) |
| SE (1) | SE7702907L (en) |
| YU (1) | YU70177A (en) |
| ZA (1) | ZA771569B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2941530A1 (en) * | 1979-10-13 | 1981-04-23 | Kali-Chemie Pharma Gmbh, 3000 Hannover | N (DOWN ARROW) B (UP ARROW) QUARTERS DERIVATIVES OF SANDWICIN AND ISOSANDWICIN, METHODS AND INTERMEDIATE PRODUCTS FOR THE PRODUCTION OF THE DERIVATIVES, THE MEDICINAL PRODUCT CONTAINING THE DERIVATIVES AND THE USE OF THE DERIVATIVES |
| DE2941531A1 (en) * | 1979-10-13 | 1981-04-23 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 10-BROMSANDWICIN AND 10-BROMISOSANDWICIN, METHOD FOR THE PRODUCTION AND USE THEREOF |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1154120B (en) * | 1962-01-10 | 1963-09-12 | Thomae Gmbh Dr K | Process for the production of new ajmaline derivatives |
| GB1582627A (en) * | 1976-01-16 | 1981-01-14 | Inverni Della Beffa Spa | Derivatives of sandwicine and isosandwicine and pharmaceutical compositions comprising sandwicine isosandwicine and derivatives thereof |
-
1976
- 1976-03-17 DE DE19762611162 patent/DE2611162A1/en active Granted
-
1977
- 1977-02-23 MX MX775461U patent/MX4788E/en unknown
- 1977-03-02 AR AR266736A patent/AR211567A1/en active
- 1977-03-04 CH CH275377A patent/CH631714A5/en not_active IP Right Cessation
- 1977-03-04 CS CS771481A patent/CS197287B2/en unknown
- 1977-03-08 IL IL51630A patent/IL51630A/en unknown
- 1977-03-08 IT IT21028/77A patent/IT1084656B/en active
- 1977-03-10 NL NL7702609A patent/NL7702609A/en not_active Application Discontinuation
- 1977-03-11 GB GB41140/79A patent/GB1583555A/en not_active Expired
- 1977-03-11 ES ES456755A patent/ES456755A1/en not_active Expired
- 1977-03-11 GB GB10521/77A patent/GB1583554A/en not_active Expired
- 1977-03-14 PT PT66298A patent/PT66298B/en unknown
- 1977-03-15 DD DD7700197869A patent/DD128774A5/en unknown
- 1977-03-15 FR FR7707630A patent/FR2344557A1/en active Granted
- 1977-03-15 SE SE7702907A patent/SE7702907L/en not_active Application Discontinuation
- 1977-03-15 GR GR53002A patent/GR62637B/en unknown
- 1977-03-15 BE BE6045928A patent/BE852493A/en not_active IP Right Cessation
- 1977-03-16 NO NO770934A patent/NO146282C/en unknown
- 1977-03-16 ZA ZA00771569A patent/ZA771569B/en unknown
- 1977-03-16 DK DK114677A patent/DK143602C/en active
- 1977-03-16 YU YU00701/77A patent/YU70177A/en unknown
- 1977-03-16 AT AT179277A patent/AT353986B/en not_active IP Right Cessation
- 1977-03-17 FI FI770855A patent/FI61898C/en not_active IP Right Cessation
- 1977-03-17 CA CA274,191A patent/CA1072959A/en not_active Expired
- 1977-03-17 JP JP2976377A patent/JPS52113988A/en active Pending
- 1977-05-11 IN IN707/CAL/77A patent/IN146149B/en unknown
-
1978
- 1978-09-05 FR FR7825511A patent/FR2392995A1/en active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |