US6063561A
Expired / Lapsed
US
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Polyketide derivatives and recombinant methods for making same
Assignee: Abbott Laboratories
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Filing: 1998-05-13
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Granted: 2000-05-16
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Expires: 2018-05-13
Abstract
Abstract The invention provides novel erythromycin derivatives in which methyl groups on the macrolactone ring have been substituted with --H, -Et, and/or --OH and the ethyl side-chain has been substituted with hydroxymethyl or dihydroxycyclohexylmethyl side-chains. The invention also provides reagents such as isolated polynucleotides, vectors comprising the polynucleotides and host cells transformed with the vectors for making the novel compounds. Methods for making the compounds utilizing genetic engineering techniques are also disclosed.
Inventors
- 👤 Leonard Katz
- 👤 Diane L. Stassi
- 👤 Richard G. Summers, Jr.
- 👤 Xiaoan Ruan
- 👤 Ana Pereda-Lopez
- 👤 Stephan J. Kakavas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 23:49
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08; C12; C12N; C12N15/00; C12N15/09; C12N15/11; C12N15/52; C12P; C12P19/00; C12P19/44; C12P19/60; C12P19/62
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
110 words
A compound of the formula: ##STR4## wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from Q wherein Q is selected from the group consisting of (a) --H, (b) -Me, (c) -Et, and (d) --OH; R 7 is selected from the group consisting of -Et, --HOMe (hydroxymethyl), and 3,4-dihydroxycyclohexylmethyl; L 1 and L 2 are independently --H or --OH; L 3 is D-desosamine or --OH; and L 4 is L-mycarose, L-cladinose or --OH with the proviso that when R 7 is -Et and R 1 -R 5 are -Me, R 6 is other than --H or -Me.
Claim 2
Dependent Claim
110 words
A compound of the formula: ##STR4## wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from Q wherein Q is selected from the group consisting of (a) --H, (b) -Me, (c) -Et, and (d) --OH; R 7 is selected from the group consisting of -Et, --HOMe (hydroxymethyl), and 3,4-dihydroxycyclohexylmethyl; L 1 and L 2 are independently --H or --OH; L 3 is D-desosamine or --OH; and L 4 is L-mycarose, L-cladinose or --OH with the proviso that when R 7 is -Et and R 1 -R 5 are -Me, R 6 is other than --H or -Me.
Claim 3
Dependent Claim
38 words
The compound of claim 1 wherein Q is selected from the group consisting of (a), (b), and (c), R 7 is -Et and L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 4
Dependent Claim
38 words
The compound of claim 1 wherein Q is selected from the group consisting of (a), (b), and (d), R 7 is -Et and L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 5
Dependent Claim
38 words
The compound of claim 1 wherein Q is selected from the group consisting of (a), (c), and (d), R 7 is -Et and L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 6
Dependent Claim
38 words
The compound of claim 1 wherein Q is selected from the group consisting of (b), (c), and (d), R 7 is -Et and L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 7
Dependent Claim
357 words
The compound of claim 1 wherein (a) R 6 and R 1 are --H and R 2 , R 3 , R 4 and R 5 are -Me, (b) R 5 and R 1 are --H and R 2 , R 3 , R 4 and R 6 are -Me, (c) R 4 and R 1 are --H and R 2 , R 3 , R 5 and R 6 are -Me, (d) R 3 and R 1 are --H and R 2 , R 4 , R 5 and R 6 are -Me, (e) R 2 and R 1 are --H and R 3 , R 4 , R 5 and R 6 are -Me, (f) R 6 and R 2 are --H and R 1 , R 3 , R 4 and R 5 are -Me, (g) R 5 and R 2 are --H and R 1 , R 3 , R 4 and R 6 are -Me, (h) R 4 and R 2 are --H and R 1 , R 3 , R 5 and R 6 are -Me, (i) R 3 and R 2 are --H and R 1 , R 4 , R 5 and R 6 are -Me, (j) R 6 and R 3 are --H and R 1 , R 2 , R 4 and R 5 are -Me, (k) R 5 and R 3 are --H and R 1 , R 2 , R 4 and R 6 are -Me, (l) R 4 and R 3 are --H and R 1 , R 2 , R 5 and R 6 are -Me, (m) R 6 and R 4 are --H and R 1 , R 2 , R 3 and R 5 are -Me, (n) R 5 and R 4 are --H and R 1 , R 2 , R 3 and R 6 are -Me, or (o) R 6 and R 5 are --H and R 1 , R 2 , R 3 and R 4 are -Me; R 7 is -Et; and L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 8
Dependent Claim
30 words
The compound of claim 6 wherein (a)-(o) and R 7 are as defined therein, L 1 and L 2 are --OH, L 3 is D-desosamine and L 4 is L-cladinose.
Claim 9
Dependent Claim
467 words
The compound of claim 1 wherein (a) R 6 , R 2 and R 1 are --H and R 3 , R 4 and R 5 are -Me, (b) R 5 , R 2 and R 1 are --H and R 3 , R 4 and R 6 are -Me, (c) R 4 , R 2 and R 1 are --H and R 3 , R 5 and R 6 are -Me, (d) R 3 , R 2 and R 1 are --H and R 4 , R 5 and R 6 are -Me, (e) R 6 , R 3 and R 1 are --H and R 2 , R 4 and R 5 are -Me, (f) R 5 , R 3 and R 1 are --H and R 2 , R 4 and R 6 are -Me, (g) R 4 , R 3 and R 1 are --H and R 2 , R 5 and R 6 are -Me, (h) R 6 , R 4 and R 1 are --H and R 2 , R 3 and R 5 are -Me, (i) R 5 , R 4 and R 1 are --H and R 2 , R 3 and R 6 are -Me, (j) R 6 , R 5 and R 1 are --H and R 2 , R 3 and R 4 are -Me, (k) R 6 , R 3 and R 2 are --H and R 1 , R 4 and R 5 are -Me, (l) R 5 , R 3 and R 2 are --H and R 1 , R 4 and R 6 are -Me, (m) R 4 , R 3 and R 2 are --H and R 1 , R 5 and R 6 are -Me, (n) R 6 , R 4 and R 2 are --H and R 1 , R 3 and R 5 are -Me, (o) R 5 , R 4 and R 2 are --H and R 1 , R 3 and R 6 are -Me, (p) R 6 , R 5 and R 2 are --H and R 1 , R 3 and R 4 are -Me, (q) R 6 , R 4 and R 3 are --H and R 1 , R 2 and R 5 are -Me, (r) R 5 , R 4 and R 3 are --H and R 1 , R 2 and R 6 are -Me, (s) R 6 , R 5 and R 3 are --H and R 1 , R 2 and R 4 are -Me, or (t) R 6 , R 5 and R 4 are --H and R 1 , R 2 and R 3 are -Me; R 7 is -Et and L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 10
Dependent Claim
30 words
The compound of claim 8 wherein (a)-(t) and R 7 are as defined therein, L 1 and L 2 are --OH, L 3 is D-desosamine and L 4 is L-cladinose.
Claim 11
Dependent Claim
349 words
The compound of claim 1 wherein (a) R 6 , R 3 , R 2 and R 1 are --H and R 5 , and R 4 are -Me, (b) R 5 , R 3 , R 2 and R 1 are --H and R 6 , and R 4 are -Me, (c) R 4 , R 3 , R 2 and R 1 are --H and R 5 , and R 6 are -Me, (d) R 6 , R 4 , R 2 and R 1 are --H and R 3 , and R 5 are -Me, (e) R 5 , R 4 , R 2 and R 1 are --H and R 3 , and R 6 are -Me, (f) R 6 , R 5 , R 2 and R 1 are --H and R 3 , and R 4 are -Me, (g) R 6 , R 4 , R 3 and R 1 are --H and R 2 , and R 5 are -Me, (h) R 5 , R 4 , R 3 and R 1 are --H and R 2 , and R 6 are -Me, (i) R 6 , R 5 , R 4 and R 1 are --H and R 2 , and R 3 are -Me, (j) R 2 , R 4 , R 3 and R 1 are --H and R 5 , and R 6 are -Me, (k) R 6 , R 4 , R 3 and R 2 are --H and R 1 , and R 5 are -Me, (l) R 5 , R 4 , R 3 and R 2 are --H and R 1 , and R 6 are -Me, (m) R 6 , R 5 , R 3 and R 2 are --H and R 1 , and R 4 are -Me, or (n) R 6 , R 5 , R 4 and R 3 are --H and R 1 , and R 2 are -Me; R 7 is -Et and L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 12
Dependent Claim
30 words
The compound of claim 10 wherein (a)-(n) and R 7 are as defined therein, L 1 and L 2 are --OH, L 3 is D-desosamine and L 4 is L-cladinose.
Claim 13
Dependent Claim
159 words
The compound of claim 1 wherein (a) R 5 , R 4 , R 3 , R 2 and R 1 are --H and R 6 is -Me, (b) R 6 , R 4 , R 3 , R 2 and R 1 are --H and R 5 is -Me, (c) R 6 , R 5 , R 3 , R 2 and R 1 are --H and R 4 is -Me, (d) R 6 , R 5 , R 4 , R 2 and R 1 are --H and R 3 is -Me, (e) R 6 , R 5 , R 4 , R 3 and R 1 are --H and R 2 is -Me, or (f) R 6 , R 5 , R 4 , R 3 and R 2 are --H and R 1 is -Me; R 7 is -Et and L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 14
Dependent Claim
30 words
The compound of claim 12 wherein (a)-(f) and R 7 are as defined therein, L 1 and L 2 are --OH, L 3 is D-desosamine and L 4 is L-cladinose.
Claim 15
Dependent Claim
44 words
The compound of claim 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are --H and R 7 , L 1 , L 2 , L 3 and L 4 are as defined therein.
Claim 16
Dependent Claim
46 words
The compound of claim 14 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined therein, L 1 and L 2 are --OH, L 3 is D-desosamine and L 4 is L-cladinose.
Claim 17
Dependent Claim
22 words
The compound of claim 1 selected from the group consisting of 6,10-didesmethyl-6-ethylerythromycin A; 10,12-didesmethyl-12-deoxy-12-ethylerythromycin A; 10,12-didesmethyl-12-deoxy-10-hydroxyerythromycin A; 6,10,12-tridesmethyl-6,12-diethylerythromycin A, and 6,10,12-tridesmethyl-6-deoxy-6,12-diethylerythromycin A.
Claim 18
Dependent Claim
52 words
The compound of claim 1 selected from the group consisting of 10-desmethylerythronolide B, 10-desmethyl-6-deoxyerythronolide B, 12-desmethylerythronolide B, 12-desmethyl-6-deoxyerythronolide B, 12-desmethyl-12-ethylerythronolide B, 6-desmethyl-6-deoxy-6-ethylerythronolide B, 10-desmethylerythromycin A, 10-desmethyl-12-deoxyerythromycin A, 10-desmethyl-6,12-dideoxyerythromycin A, 12-desmethylerythromycin A, 12-desmethyl-12-deoxyerythromycin A, 12-desmethyl-6,12-dideoxyerythromycin A, 6-desmethyl-6-ethylerythromycin A, 12-desmethyl-12-ethylerythromycin A, 12-desmethyl-12-deoxy-12-ethylerythromycin A, 10-desmethyl-10-hydroxyerythromycin A, 12-desmethyl-12-epihydroxyerythromycin A, 10,12-didesmethylerythromycin A, 10,12-didesmethyl-12-deoxyerythromycin A, and 10,12-didesmethyl-6,12-dideoxyerythromycin A.
Claim 19
Dependent Claim
38 words
The compound of claim 1 selected from the group consisting of 10-desmethylerythronolide B, 10-desmethyl-6-deoxyerythronolide B, 12-desmethylerythronolide B, 12-desmethyl-6-deoxyerythronolide B, 10-desmethylerythromycin A, 10-desmethyl-12-deoxyerythromycin A, 10-desmethyl-6,12-dideoxyerythromycin A, 12-desmethylerythromycin A, 12-desmethyl-12-deoxyerythromycin A, 12-desmethyl-6,12-dideoxyerythromycin A, 10,12-didesmethylerythromycin A, 10,12-didesmethyl-12-deoxyerythromycin A, and 10,12-didesmethyl-6,12-dideoxyerythromycin A.
Claim 20
Dependent Claim
15 words
A compound selected from the group consisting of 10-desmethylerythromycin A, 10-desmethyl-12-deoxyerythromycin A, and 12-desmethyl-12-deoxyerythromycin A.
Claim 21
Dependent Claim
15 words
A compound selected from the group consisting of 10-desmethylerythromycin A, 10-desmethyl-12-deoxyerythromycin A, and 12-desmethyl-12-deoxyerythromycin A.
Claim 22
Dependent Claim
23 words
The compound of claim 1 selected from the group consisting of 8-desmethyl-8-hydroxyerythromycin A, 6-desmethyl-6-epierythromycin A, 4-desmethyl-4-hydroxyerythromycin A, 2-desmethyl-2-hydroxyerythromycin A and 13-desethyl-13-hydroxymethol erythromycin A.
Claim 23
Dependent Claim
18 words
The compound of claim 1 selected from the group consisting of 2,12-didesmethyl-2,12-dihydroxyerythromycin, 4,10-didesmethyl-4, 10-dihydroxyerythromycin, 10,12-didesmethyl-10-hydroxyerythromycin, and 6,10-didesmethyl-6-ethyl-10-hydroxyerythromycin A.
Claim 24
Dependent Claim
9 words
The compound of claim 1 which is 13-desethyl-13-(3',4'-dihydroxycyclohexyl)methylerythromycin A.
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