GB1206439A - 7-substituted tetracyclines - Google Patents
7-substituted tetracyclinesInfo
- Publication number
- GB1206439A GB1206439A GB5718667A GB5718667A GB1206439A GB 1206439 A GB1206439 A GB 1206439A GB 5718667 A GB5718667 A GB 5718667A GB 5718667 A GB5718667 A GB 5718667A GB 1206439 A GB1206439 A GB 1206439A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrazino
- bis
- alkyl
- compound
- amino
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J37/00—Discharge tubes with provision for introducing objects or material to be exposed to the discharge, e.g. for the purpose of examination or processing thereof
- H01J37/02—Details
- H01J37/18—Vacuum locks ; Means for obtaining or maintaining the desired pressure within the vessel
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K15/00—Electron-beam welding or cutting
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US608264A US3403179A (en) | 1967-01-10 | 1967-01-10 | Novel 7-(1, 2-bis-substituted-hydrazino)-tetracyclines and methods of preparing same |
US62029467A | 1967-03-03 | 1967-03-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1206439A true GB1206439A (en) | 1970-09-23 |
Family
ID=27085712
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5718667A Expired GB1206439A (en) | 1967-01-10 | 1967-12-15 | 7-substituted tetracyclines |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS5215594B1 (en) |
BE (1) | BE709112A (en) |
DE (1) | DE1643767C3 (en) |
ES (1) | ES352203A1 (en) |
FR (1) | FR1550023A (en) |
GB (1) | GB1206439A (en) |
NL (1) | NL162066C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ301835B6 (en) * | 1999-09-14 | 2010-07-07 | Trustees Of Tufts College | Process for preparing 7-, 9- or 13-substituted tetracycline compound, reactive tetracycline chemical complex and tetracycline compound substituted in position 7 or 9 |
-
1967
- 1967-12-15 GB GB5718667A patent/GB1206439A/en not_active Expired
-
1968
- 1968-01-05 FR FR1550023D patent/FR1550023A/fr not_active Expired
- 1968-01-09 BE BE709112D patent/BE709112A/xx not_active IP Right Cessation
- 1968-01-10 NL NL6800362A patent/NL162066C/en not_active IP Right Cessation
- 1968-01-10 DE DE1968A0057905 patent/DE1643767C3/en not_active Expired
- 1968-03-30 ES ES352203A patent/ES352203A1/en not_active Expired
-
1972
- 1972-08-10 JP JP7954472A patent/JPS5215594B1/ja active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ301835B6 (en) * | 1999-09-14 | 2010-07-07 | Trustees Of Tufts College | Process for preparing 7-, 9- or 13-substituted tetracycline compound, reactive tetracycline chemical complex and tetracycline compound substituted in position 7 or 9 |
Also Published As
Publication number | Publication date |
---|---|
BE709112A (en) | 1968-07-09 |
DE1643767C3 (en) | 1981-01-08 |
DE1643767B2 (en) | 1980-04-17 |
NL162066B (en) | 1979-11-15 |
FR1550023A (en) | 1968-12-13 |
JPS5215594B1 (en) | 1977-04-30 |
NL6800362A (en) | 1968-07-11 |
NL162066C (en) | 1980-04-15 |
DE1643767A1 (en) | 1972-03-02 |
ES352203A1 (en) | 1970-02-01 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PE20 | Patent expired after termination of 20 years |