US4345069A
Expired / Lapsed
US
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Deformyltylosin derivatives
Assignee: Asahi Kasei Corp
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Filing: 1980-09-05
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Granted: 1982-08-17
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Expires: 2000-09-05
Abstract
Abstract Deformyltylosin derivatives of the formula <IMAGE> wherein A is <IMAGE> -CH=CH- or -CH2-CH2-, R1 is hydrogen, lower alkanoyl or aryl-lower alkanoyl, X1 and X2 are hydrogen or are connected to form a valence bond, Y1 and Y2 are hydrogen or are connected to form a valence bond, Q1 is hydrogen or methyl, Q2 is hydrogen or <IMAGE> R2 is hydrogen or lower alkanoyl, R is hydrogen or <IMAGE> R3 is hydrogen or C2-5 alkanoyl, and R4 is hydrogen or C2-6 alkanoyl, and when R3 is not hydrogen, then R4 is not hydrogen, or a pharmaceutically acceptable salt thereof, have strong antibacterial activities as compared to the known antibiotic tylosin, and also have enhanced antibacterial activities against all macrolide antibiotic-resistant strains such as A, B and C group strains, and have higher blood levels as compared with tylosin.
Inventors
- 👤 Hideo Sakakibara
- 👤 Tatsuro Fujiwara
- 👤 Osamu Okegawa
- 👤 Eiichi Honda
- 👤 Susumu Watanabe
- 👤 Tetsuo Matsuda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 01:49
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
116 words
A compound of the formula ##STR62## wherein A is ##STR63## --CH═CH-- or --CH 2 --CH 2 --, R 1 is hydrogen, lower alkanoyl or phenyl-lower alkanoyl, X 1 and X 2 are hydrogen or are connected to form a valence bond, Y 1 and Y 2 are hydrogen or are connected to form a valence bond, Q 1 is hydrogen or methyl, Q 2 is hydrogen or ##STR64## R 2 is hydrogen or lower alkanoyl, R is hydrogen or ##STR65## R 3 is hydrogen or C 2-5 alkanoyl, and R 4 is hydrogen or C 2-6 alkanoyl, and when R 3 is not hydrogen, then R 4 is not hydrogen, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
116 words
A compound of the formula ##STR62## wherein A is ##STR63## --CH═CH-- or --CH 2 --CH 2 --, R 1 is hydrogen, lower alkanoyl or phenyl-lower alkanoyl, X 1 and X 2 are hydrogen or are connected to form a valence bond, Y 1 and Y 2 are hydrogen or are connected to form a valence bond, Q 1 is hydrogen or methyl, Q 2 is hydrogen or ##STR64## R 2 is hydrogen or lower alkanoyl, R is hydrogen or ##STR65## R 3 is hydrogen or C 2-5 alkanoyl, and R 4 is hydrogen or C 2-6 alkanoyl, and when R 3 is not hydrogen, then R 4 is not hydrogen, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
18 words
A compound as claimed in claim 1, wherein said compound is 19-deformyltylosin or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
28 words
A compound of the formula ##STR66## wherein R 3 is hydrogen or C 2-5 alkanoyl, and R 41 is C 2-6 alkanoyl, or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
28 words
A compound of the formula ##STR66## wherein R 3 is hydrogen or C 2-5 alkanoyl, and R 41 is C 2-6 alkanoyl, or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
12 words
A compound as claimed in claim 3, wherein R 3 is hydrogen.
Claim 7
Dependent Claim
14 words
A compound as claimed in claim 3, wherein R 3 is C 2-5 alkanoyl.
Claim 8
Dependent Claim
18 words
A compound as claimed in claim 5, wherein said compound is 3"-acetyl-19-deformyl-4"-isovaleryltylosin or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
33 words
A compound of the formula ##STR67## wherein R 12 is lower alkanoyl, R 3 is hydrogen or C 2-5 alkanoyl and R 41 is C 2-6 alkanoyl, or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
33 words
A compound of the formula ##STR67## wherein R 12 is lower alkanoyl, R 3 is hydrogen or C 2-5 alkanoyl and R 41 is C 2-6 alkanoyl, or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
18 words
A compound as claimed in claim 7, wherein said compound is 3,3",4"-triacetyl-19-deformyltylosin, or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
38 words
A compound as claimed in claim 1, wherein said compound is represented by the formula ##STR68## wherein R 3 is hydrogen or C 2-5 alkanoyl and R 41 is C 2-6 alkanoyl, or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
19 words
A compound as claimed in claim 9, wherein said compound is 3", 4"-diacetyl-19-deformyl-2,3-didehydro-3-dehydroxytylosin or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
40 words
A compound as claimed in claim 1, wherein said compound is represented by the formula ##STR69## wherein R 1 is hydrogen, lower alkanoyl or phenyl-lower alkanoyl and R 2 is hydrogen or lower alkanoyl, or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
18 words
A compound as claimed in claim 11, wherein said compound is 19-deformyl-4'-demycarosyltylosin or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
24 words
A compound as claimed in claim 11, wherein R 1 is lower alkanoyl and R 2 is hydrogen, or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
18 words
A compound as claimed in claim 13, wherein said compound is 3-acetyl-19-deformyl-4'-demycarosyltylosin or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
18 words
A compound as claimed in claim 13, wherein said compound is 19-deformyl-4'-demycarosyl-3-propionyltylosin or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
18 words
A compound as claimed in claim 13, wherein said compound is 3-butyryl-19-deformyl-4'-demycarosyltylosin or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
24 words
A compound as claimed in claim 11, wherein R 1 is phenyl-lower alkanoyl and R 2 is hydrogen or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
18 words
A compound as claimed in claim 17, wherein said compound is 19-deformyl-4'-demycarosyl-3-phenylacetyltylosin or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
24 words
A compound as claimed in claim 11, wherein R 1 is hydrogen and R 2 is lower alkanoyl, or a pharmaceutically acceptable salt thereof.
Claim 23
Dependent Claim
19 words
A compound as claimed in claim 19, in which said compound is 4'"-butyryl-19-deformyl-4'-demycarosyltylosin or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim
16 words
A compound as claimed in claim 11, wherein R 1 and R 2 are lower alkanoyl.
Claim 25
Dependent Claim
18 words
A compound as claimed in claim 21, wherein said compound is 3,4'"-diacetyl-19-deformyl-4'-demycarosyltylosin or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
18 words
A compound as claimed in claim 1, wherein said compound is 19-deformyl-2,3-didehydro-3-dehydroxy-4'-demyarosyltylosin or a pharmaceutically acceptable salt thereof.
Claim 27
Dependent Claim
18 words
A compound as claimed in claim 1, wherein said compound is 19-deformyl-4'-demycarosyl-10,11,12,13-tetrahydrotylosin or a pharmaceutically acceptable salt thereof.
Claim 28
Dependent Claim
18 words
A compound as claimed in claim 1, wherein said compound is 19-deformyl-3-dehydroxy-4'-demycarosyl-10,11,12,13-tetrahydrotylosin or a pharmaceutically acceptable salt thereof.
Claim 29
Dependent Claim
18 words
A compound as claimed in claim 1, wherein said compound is 19-deformyl-4'-demycarosyl-23-demysinosyltylosin or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim
18 words
A compound as claimed in claim 1, wherein said compound is 20-deoxo-4'-demycarosyltylosin or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
US3321368A
Cited
US3769273A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-08-16 | 1986-02-15 | 1986-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-16 | 1990-02-15 | 1990-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-16 | 1994-02-15 | 1994-08-17 | $7700.00 | Window Closed / Lapsed |