http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1206439-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_14effe3850d2129f863b969dac4f1db8 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/H01J37-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/B23K15-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C231-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/H01J37-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C67-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/B23K15-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C231-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C237-26 |
| filingDate | 1967-12-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_5c6024f576dfbec7b002d95e4a68c90f |
| publicationDate | 1970-09-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1206439-A |
| titleOfInvention | 7-substituted tetracyclines |
| abstract | 1,206,439. 7 - Bis - substituted hydrazino tetracyclines. AMERICAN CYANAMID CO. 15 Dec., 1967 [10 Jan., 1967; 3 March, 1967], No. 57186/67. Heading C2A. The invention comprises 7-[bis-substituted hydrazino] tetracyclines of formulµ wherein R is C 1 -C 6 alkoxy, phenyl C 1 -C 6 alkoxy, phenoxy, amino, C 1 -C 6 alkylamino, phenyl C 1 -C 6 alkylamino or anilino; R 1 is H, alpha-CH3 or beta-CH 3 ; R 2 is H or beta OH with the proviso that when R 1 is beta-CH 3 then R 2 is H; R 1 and R 2 taken together is CH 2 ; R 3 is H or OH with the proviso that when R 3 is OH then R 1 is CH 3 or R 1 and R 2 taken together is CH 2 ; and X is F, Cl or Br. The compounds are prepared by reacting a compound of Formula (I) or Formula (II) wherein the 7-position of the tetracycline nucleus is H, with a substituted azodicarbonyl derivative of formula wherein R has the above meaning, in an acidic medium, e.g. an inert organic solvent such as tetrahydrofuran and a strong acid such as methane-sulphonic acid. The corresponding 7-amino tetracyclines are obtained by treating the compounds of Formulµ (I) and (II) with 57% hydriodic acid at 100‹ C. or with hydrogen in the presence of a catalyst. The 7-[1,2-bis- (carbobenzyloxy) hydrazino] tetracycline may be subjected to reductive alkylation by treatment with a carbonyl compound of formula wherein R 4 is H or C 1 -C 6 alkyl and R 5 is H or C 1 -C 6 alkyl in the presence of a reducing agent (e.g. hydrogen), a catalyst and an inert solvent. The compound produced is the 7- mono-(C 1-6 alkyl) amino or 7-di-(C 1-6 alkyl) amino tetracycline wherein R 1 , R 2 , R 3 and X of the 7-hydrazino compound remain unchanged. A typical compound is 7-[1,2-bis-(carbobenzyloxy) hydrazino] -6-demethyl-6-deoxytetracycline. Salts may be formed with mineral acids (e.g. hydrochloric acid) and organic acids (e.g. trichloroacetic acid). |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CZ-301835-B6 |
| priorityDate | 1967-01-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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