US4205163A
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US
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Tylosin derivatives
Assignee: Mercian Corp
•
Filing: 1978-10-23
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Granted: 1980-05-27
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Expires: 1998-10-23
Abstract
Abstract A number of 4''-acyl derivatives of tylosin and acetyltylosin which are prepared by first protectively acylating at the 2'-hydroxyl group of tylosin or acetyltylosin, secondly at the 4'''-hydroxyl group thereof, thirdly at the 4''-hydroxyl group thereof and finally deacylating the 2'- and 4'''-acyl groups to produce new 4''-acyl derivatives of tylosin or acetyltylosin which effect high blood level compared to those tylosin derivatives heretofore are disclosed.
Inventors
- 👤 Shunro Mori
- 👤 Rokuro Okamoto
- 👤 Taiji Inui
- 👤 Tomio Takeuchi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 01:54
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
150 words
An acyl derivative of tylosin of the following formula I: ##STR36## wherein R 1 represents hydrogen or acetyl, R 2 represents hydrogen, acetyl, propionyl or chlorinated acetyl, R 3 represents hydrogen, chlorinated acetyl, carboethoxy or phenoxyacetyl, and R 4 represents hydrogen or ##STR37## wherein R 5 represents hydrogen, methyl, ethyl, hydroxyl or acetoxy, and R 6 represents an alkyl having 3 to 8 carbons (when the number of the carbons is 3, R 5 being a group other than hydrogen), phenyl, 4-nitrophenyl, 4-acetoxyphenyl, naphthyl, benzyl, 4-acetoxybenzyl, cyclohexylmethyl, thienyl, pyridyl, N-acetylanilino, imidazolylmethyl, phenylthio, 4-methylphenylthio, 3-methylphenylthio, 4-chlorophenylthio, benzylthio, phenylthiomethyl, cyclohexylthio, pyridylthio, benzenesulfonyl, phenoxy, naphthoxy or phenoxymethyl, with the proviso that when R 4 represents hydrogen, R 2 and R 3 each represents a group other than hydrogen, and when R 4 represents a group other than hydrogen, R 2 and R 3 each represents hydrogen and a nontoxic acid addition salt thereof.
Claim 2
Dependent Claim
150 words
An acyl derivative of tylosin of the following formula I: ##STR36## wherein R 1 represents hydrogen or acetyl, R 2 represents hydrogen, acetyl, propionyl or chlorinated acetyl, R 3 represents hydrogen, chlorinated acetyl, carboethoxy or phenoxyacetyl, and R 4 represents hydrogen or ##STR37## wherein R 5 represents hydrogen, methyl, ethyl, hydroxyl or acetoxy, and R 6 represents an alkyl having 3 to 8 carbons (when the number of the carbons is 3, R 5 being a group other than hydrogen), phenyl, 4-nitrophenyl, 4-acetoxyphenyl, naphthyl, benzyl, 4-acetoxybenzyl, cyclohexylmethyl, thienyl, pyridyl, N-acetylanilino, imidazolylmethyl, phenylthio, 4-methylphenylthio, 3-methylphenylthio, 4-chlorophenylthio, benzylthio, phenylthiomethyl, cyclohexylthio, pyridylthio, benzenesulfonyl, phenoxy, naphthoxy or phenoxymethyl, with the proviso that when R 4 represents hydrogen, R 2 and R 3 each represents a group other than hydrogen, and when R 4 represents a group other than hydrogen, R 2 and R 3 each represents hydrogen and a nontoxic acid addition salt thereof.
Claim 3
Dependent Claim
46 words
An acyl derivative of tylosin according to claim 1 having the following formula II: ##STR38## wherein R 1 represents hydrogen or acetyl, R 2 represents acetyl, propionyl or chlorinated acetyl, and R 3 represents chlorinated acetyl, carboethoxy or phenoxyacetyl and a nontoxic acid addition salt thereof.
Claim 4
Dependent Claim
21 words
An acyl derivative according to claim 1 or 2 wherein the derivative is 2'-acetyl-4'''-monochloroacetyltylosin and a nontoxic acid addition salt thereof.
Claim 5
Dependent Claim
21 words
An acyl derivative according to claim 1 or 2 wherein the derivative is 2'-acetyl-4'''-trichloroacetyltylosin and a nontoxic acid addition salt thereof.
Claim 6
Dependent Claim
21 words
An acyl derivative according to claim 1 or 2 wherein the derivative is 3,2'-diacetyl-4'''-monochloroacetyltylosin and a nontoxic acid addition salt thereof.
Claim 7
Dependent Claim
21 words
An acyl derivative according to claim 1 or 2 wherein the derivative is 3,2'-diacetyl-4'''-trichloroacetyltylosin and a nontoxic acid addition salt thereof.
Claim 8
Dependent Claim
21 words
An acyl derivative according to claim 1 or 2 wherein the derivative is 2'-acetyl-4'''-phenoxyacetyltylosin and a nontoxic acid addition salt thereof.
Claim 9
Dependent Claim
21 words
An acyl derivative according to claim 1 or 2 wherein the derivative is 3,2'-diacetyl-4'''-carboethoxytylosin and a nontoxic acid addition salt thereof.
Claim 10
Dependent Claim
97 words
An acyl derivative of tylosin according to claim 1 having the following formula IV: ##STR39## wherein R 1 represents hydrogen or acetyl, R 2 represents hydrogen, R 3 represents hydrogen, R 5 represents hydrogen, methyl, ethyl, hydroxyl or acetoxy, and R 6 represents an alkyl having 3 to 8 carbons (when the number of the carbons is 3, R 5 being a group other than hydrogen), phenyl, 4-nitrophenyl, 4-acetoxyphenyl, naphthyl, benzyl, 4-acetoxybenzyl, cyclohexylmethyl, thienyl, pyridyl, N-acetylanilino, imidazolylmethyl, phenylthio, 4-methylphenylthio, 3-methylphenylthio, 4-chlorophenylthio, benzylthio, phenylthiomethyl, cyclohexylthio, pyridylthio, benzenesulfonyl, phenoxy, naphthoxy or phenoxymethyl, and a nontoxic acid addition salt thereof.
Claim 11
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-n-caproyltylosin and a nontoxic acid addition salt thereof.
Claim 12
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-n-caproyltylosin and a nontoxic acid addition salt thereof.
Claim 13
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-n-caprylyltylosin and a nontoxic acid addition salt thereof.
Claim 14
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-n-capryltylosin and a nontoxic acid addition salt thereof.
Claim 15
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-iso-caproyltylosin and a nontoxic acid addition salt thereof.
Claim 16
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-methyl-n-valeryltylosin and a nontoxic acid addition salt thereof.
Claim 17
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-ethyl-n-butyryltylosin and a nontoxic acid addition salt thereof.
Claim 18
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-(4-nitrophenyl)acetyltylosin and a nontoxic acid addition salt thereof.
Claim 19
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-α-phenylpropionyltylosin and a nontoxic acid addition salt thereof.
Claim 20
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-α-phenyl-n-butyryltylosin and a nontoxic acid addition salt thereof.
Claim 21
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-D-(α-hydroxyphenylacetyl)tylosin and a nontoxic acid addition salt thereof.
Claim 22
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-L-(α-hydroxyphenylacetyl)tylosin and a nontoxic acid addition salt thereof.
Claim 23
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-D-(α-acetoxyphenylacetyl)tylosin and a nontoxic acid addition salt thereof.
Claim 24
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-L-(α-acetoxyphenylacetyl)tylosin and a nontoxic acid addition salt thereof.
Claim 25
Dependent Claim
22 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-[α-acetoxy-(4-acetoxyphenyl)acetyl] tylosin and a nontoxic acid addition salt thereof.
Claim 26
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-α-naphthylacetyltylosin and a nontoxic acid addition salt thereof.
Claim 27
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-α-naphthylacetyltylosin and a nontoxic acid addition salt thereof.
Claim 28
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-β-phenylpropionyltylosin and a nontoxic acid addition salt thereof.
Claim 29
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-β-phenylpropionyltylosin and a nontoxic acid addition salt thereof.
Claim 30
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-L-[(α-hydroxy-β-phenyl)propionyl]tylosin and a nontoxic acid addition salt thereof.
Claim 31
Dependent Claim
22 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-L-[(α-acetoxy-β-phenyl)propionyl] tylosin and a nontoxic acid addition salt thereof.
Claim 32
Dependent Claim
22 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-[α-acetoxy-β-(4-acetoxyphenyl)propionyl] tylosin and a nontoxic acid addition salt thereof.
Claim 33
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-β-cyclohexylpropionyltylosin and a nontoxic acid addition salt thereof.
Claim 34
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-thienylacetyltylosin and a nontoxic acid addition salt thereof.
Claim 35
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-(3-pyridyl)acetyltylosin and a nontoxic acid addition salt thereof.
Claim 36
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-(N-acetylanilino)acetyltylosin and a nontoxic acid addition salt thereof.
Claim 37
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-(1-imidazolyl)propionyltylosin and a nontoxic acid addition salt thereof.
Claim 38
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-phenylthioacetyltylosin and a nontoxic acid addition salt thereof.
Claim 39
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-(4-methylphenyl)thioacetyltylosin and a nontoxic acid addition salt thereof.
Claim 40
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-(3-methylphenyl)thioacetyltylosin and a nontoxic acid addition salt thereof.
Claim 41
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-(4-chlorophenyl)thioacetyltylosin and a nontoxic acid addition salt thereof.
Claim 42
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-benzylthioacetyltylosin and a nontoxic acid addition salt thereof.
Claim 43
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-β-phenylthiopropionyltylosin and a nontoxic acid addition salt thereof.
Claim 44
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-cyclohexylthioacetyltylosin and a nontoxic acid addition salt thereof.
Claim 45
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-(4-pyridyl)thioacetyltylosin and a nontoxic acid addition salt thereof.
Claim 46
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-(4-pyridyl)thioacetyltylosin and a nontoxic acid addition salt thereof.
Claim 47
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-benzenesulfonylacetyltylosin and a nontoxic acid addition salt thereof.
Claim 48
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-phenoxyacetyltylosin and a nontoxic acid addition salt thereof.
Claim 49
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 3-acetyl-4"-phenoxyacetyltylosin and a nontoxic acid addition salt thereof.
Claim 50
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-α-phenoxypropionyltylosin and a nontoxic acid addition salt thereof.
Claim 51
Dependent Claim
21 words
An acyl derivative according to claim 1 or 9 wherein the derivative is 4"-β-naphthoxyacetyltylosin and a nontoxic acid addition salt thereof.
References Cited (Backward Citations)
US4092473A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-05-27 | 1983-11-26 | 1984-05-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-05-27 | 1987-11-26 | 1988-05-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-05-27 | 1991-11-26 | 1992-05-27 | $7700.00 | Window Closed / Lapsed |