GB1031078A - New yohimbane compounds and a new process for their manufacture - Google Patents
New yohimbane compounds and a new process for their manufactureInfo
- Publication number
- GB1031078A GB1031078A GB34123/63A GB3412363A GB1031078A GB 1031078 A GB1031078 A GB 1031078A GB 34123/63 A GB34123/63 A GB 34123/63A GB 3412363 A GB3412363 A GB 3412363A GB 1031078 A GB1031078 A GB 1031078A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- acid
- esters
- acid addition
- lactone
- 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
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
17a - Hydroxy - 18b - acyloxy - 20a - yohimbane - 16b 8 carboxylic acid esters, including novel compounds of general formula <FORM:1031078/C2/1> wherein R is acyl, R1 is a lower alkyl group optionally substituted by a lower alkoxy group a di-(lower-alkyl) amino group, a lower alkyleneimino group, or a morpholino, thiamopholino or piperazino group, R4 + R5 are hydrogen, lower alkoxy, lower alkyl, lower alkylmercapto, phenyl-lower alkoxy, di-(lower alkyl) amino or halogen, or R4 + R5 in vicinal positions together represent a methylenedioxy group and R6 is hydrogen or lower alkyl and where lower is used above it means groups containing up to 7 carbon atoms (pseudoresepine, raunescine and neocindine and disclaimed as not being novel); and their N-oxides and acid addition salts, are prepared by hydrogenolysis or acid hydrolysis of the corresponding 17-ethers or 17-esters or N-oxides or acid addition salts thereof, including novel 17a - tetrahydropyranyl - (2) - oxy - 18b - acyloxy-3b ,20a - yohimbane - 16b - carboxylic acid esters, in which the ester or ether is difficult to eliminate by alkaline hydrolysis, e.g. oxacycloalkyl-(2) ethers with at least 5 atoms as ring members and carbobenzoyl esters. The above 17-ethers and -esters are prepared by a process wherein in a 16,18-lactone of a 17a ,18b - dihydroxy - 20a - yohimbane - 16b -carboxylic acid or an N-oxide or acid addition salt thereof, the 17-hydroxyl group is etherified or esterified with a group which is difficult to eliminate by alkaline hydrolysis but easy to eliminate by hydrogenolysis or acid hydrolysis, the resulting lactone, which may be novel 17 - O - tetrahydropyranyl - pseudoreserpic acid lactone, is split with an alkaline reagent or by alcoholysis any resulting compound containing a free carbocyclic group in the 16-position is esterified and the hydroxy group in the 18-position is acylated. A product obtained above at any stage may be isomerized in the 3-position and/or any resulting compound may be oxidized to the N-oxide and/or an N-oxide may be reduced and/or a base may be converted into an acid addition salt or an acid addition salt may be converted into a free base. 16,18 - Lactones of 17a ,18b - dihydroxy-20a -yohembane 16b -carboxylic acids are prepared by formation of the lactone ring from the free acid by heating in the presence of N,N1-dicyclohexyl-carbodiimide. Pharmaceutical or veterinary compositions in conventional forms for enteral or parenteral administration and animal feedstuffs contain a hereinbefore mentioned novel compound and a carrier therefor.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1017062 | 1962-08-28 | ||
CH873363 | 1963-07-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1031078A true GB1031078A (en) | 1966-05-25 |
Family
ID=25703710
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB34123/63A Expired GB1031078A (en) | 1962-08-28 | 1963-08-28 | New yohimbane compounds and a new process for their manufacture |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1031078A (en) |
-
1963
- 1963-08-28 GB GB34123/63A patent/GB1031078A/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE2966269D1 (en) | 1-, 6- and 2-substituted-1-carba-2-penem-3-carboxylic acids, process for preparing the same and pharmaceutical compositions containing the same | |
ES378092A1 (en) | Carboxylic esters of hydroxyphenylalkanolamines | |
ES440079A1 (en) | 3-Quinoline-substituted 4-oxy-carboxamides | |
SE323866B (en) | ||
GB1031078A (en) | New yohimbane compounds and a new process for their manufacture | |
GB1399162A (en) | 6-keto-delta1,3,5-10-steroids and process for the manufacture of 6-keto-delta1,3,5-10-steroids | |
ES445489A1 (en) | Antibiotic substances derived from antibiotic 67-694(rosamicin)and processes for their preparation | |
GB1382121A (en) | Polybasic ether carboxylic acids | |
ES421098A1 (en) | Fluoro-substituted thiaxanthene derivatives | |
ES428213A1 (en) | Dialkylaminoalkyl esters of penicillin and process for the preparation thereof | |
ES422465A1 (en) | Preparation of 2-alkylaminoalkyl 6-methyl-7-nitro- 1,2,3,4-tetrahydroquinolines | |
GB1117456A (en) | 1ªß-methyl-2,3ª-methylene steroids and a process for their manufacture | |
GB1366665A (en) | Tricyclic compounds and a process for the preparation thereof | |
GB1457200A (en) | Process for the preparation of 6-substituted penicillins parcel holder | |
GB1127457A (en) | Carboxylic acid-n-methyl-piperazides and process for their manufacture | |
KR880002879A (en) | (5R, 6S, 8R) -6- (1-hydroxyethyl) -2- (3R-pyrrolidin-2-one-3-yl) thiophenem-3-carboxylic acid | |
GB748846A (en) | A process for the manufacture of pregnan-3(-a)-ol-20-one and derivatives thereof | |
GB1340512A (en) | Production of esters of chromone-2-carboxylic acids | |
GB1018780A (en) | Steroid (2,3í¬c) furazan compounds and the process for the production thereof | |
GB1423743A (en) | Derivatives of cephalosporin processes for their preparation and compositions incorporating them | |
JPS51131821A (en) | Process for preparation of gamma-halo-delta-unsaturated carboxylic acids | |
GB1282896A (en) | New 4-oxo-1,4-dihydro-3-quinolyl-carboxylic acid derivatives and process for their preparation | |
GB1118335A (en) | A process for the manufacture of carbocyclic compounds | |
GB1070115A (en) | New 1,2ª‰-methylene steroids and a process for their manufacture | |
ES363954A1 (en) | Organic compounds based upon benzoxazocines and intermediates and processes therefor |