US4282322A
Expired / Lapsed
US
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Process for enzymatic deacylation of antibiotics
Assignee: Merck and Co Inc
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Filing: 1979-08-27
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Granted: 1981-08-04
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Expires: 1999-08-27
Abstract
Abstract This invention relates to two new antibiotics, desacetyl 890A1 and desacetyl 890A3, active against both gram-positive and gram-negative bacteria, which are produced by treating 890A1 and 890A3, respectively, with an N-acetylthienamycin amidohydrolase produced by a soil microorganism isolated by enrichment techniques. This invention also relates to the process whereby N-acetylated structures of the thienamycin class of antibiotics such as N-acetyl thienamycin can be enzymatically deacetylated.
Inventors
- 👤 Jean S. Kahan
- 👤 Frederick M. Kahan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 05:58
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20; C12; C12N; C12N9/00; C12N9/14; C12N9/78; C12N9/80; C12P; C12P17/00; C12P17/18; C12P17/182; C12P17/184; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
95 words
A process for producing the compound desacetyl 890A 1 having the structure: ##STR5## produced by enzymatic cleavage of the compound 890A 1 wherein 890A 1 has the following structure: ##STR6## and wherein said 890A 1 has 100 MHz nuclear magnetic reasonance signals having chemical shifts in ppm and multiplicities indicated as 1.35 (d, J=6.5); 1.98 (s); 3.63 (d of d, J=5.2 and J=9.8); ˜4.02-4.26 (m); 3.18 (d of d, J=2 and J=10); 3.41 (t, J=6); 2.97 (d of t, J=3.5 and J=6), wherein the enzymatic cleavage utilizes an amidohydrolase capable of hydrolyzing the N-acetyl group.
Claim 2
Dependent Claim
95 words
A process for producing the compound desacetyl 890A 1 having the structure: ##STR5## produced by enzymatic cleavage of the compound 890A 1 wherein 890A 1 has the following structure: ##STR6## and wherein said 890A 1 has 100 MHz nuclear magnetic reasonance signals having chemical shifts in ppm and multiplicities indicated as 1.35 (d, J=6.5); 1.98 (s); 3.63 (d of d, J=5.2 and J=9.8); ˜4.02-4.26 (m); 3.18 (d of d, J=2 and J=10); 3.41 (t, J=6); 2.97 (d of t, J=3.5 and J=6), wherein the enzymatic cleavage utilizes an amidohydrolase capable of hydrolyzing the N-acetyl group.
Claim 3
Dependent Claim
95 words
A process for producing the compound desacetyl 890A 3 having the structure: ##STR7## produced by enzymatic cleavage of the compound 890A 3 wherein 890A 3 has the following structure: ##STR8## and wherein said 890A 3 has 100 MHz nuclear magnetic reasonance signals having chemical shifts in ppm and multiplicities indicated as 1.35 (d, J=6.5); 1.98 (s); 3.63 (d of d, J=5.2 and J=9.8); ˜4.02-4.26 (m); 3.18 (d of d, J=2 and J=10); 3.41 (t, J=6); 2.97 (d of t, J=3.5 and J=6), wherein the enzymatic cleavage utilizes an amidohydrolase capable of hydrolyzing the N-acetyl group.
Claim 4
Dependent Claim
95 words
A process for producing the compound desacetyl 890A 3 having the structure: ##STR7## produced by enzymatic cleavage of the compound 890A 3 wherein 890A 3 has the following structure: ##STR8## and wherein said 890A 3 has 100 MHz nuclear magnetic reasonance signals having chemical shifts in ppm and multiplicities indicated as 1.35 (d, J=6.5); 1.98 (s); 3.63 (d of d, J=5.2 and J=9.8); ˜4.02-4.26 (m); 3.18 (d of d, J=2 and J=10); 3.41 (t, J=6); 2.97 (d of t, J=3.5 and J=6), wherein the enzymatic cleavage utilizes an amidohydrolase capable of hydrolyzing the N-acetyl group.
Claim 5
Dependent Claim
13 words
The process according to claim 1 wherein the amidohydrolase is an N-acetylthienamycin amidohydrolase.
Claim 6
Dependent Claim
13 words
The process according to claim 2 wherein the amidohydrolase is an N-acetylthienamycin amidohydrolase.
Claim 7
Dependent Claim
13 words
The process according to claim 1 wherein the amidohydrolase is an N-acetylethanolamine amidohydrolase.
Claim 8
Dependent Claim
13 words
The process according to claim 2 wherein the amidohydrolase is an N-acetylethanolamine amidohydrolase.
Claim 9
Dependent Claim
21 words
The process according to claim 1 wherein an amidohydrolase produced by an amidohydrolase-producing strain of the microorganism Protaminobacter ruber is utilized.
Claim 10
Dependent Claim
21 words
The process according to claim 2 wherein an amidohydrolase produced by an amidohydrolase-producing strain of the microorganism Protaminobacter ruber is utilized.
Claim 11
Dependent Claim
25 words
The process for producing thienamycin which comprises intimately contacting N-acetylthienamycin with the enzyme N-acetylthienamycin amidohydrolase produced by an amidohydrolase-producing strain of the microorganism Protaminobacter ruber.
Claim 12
Dependent Claim
25 words
The process for producing thienamycin which comprises intimately contacting N-acetylthienamycin with the enzyme N-acetylthienamycin amidohydrolase produced by an amidohydrolase-producing strain of the microorganism Protaminobacter ruber.
Claim 13
Dependent Claim
28 words
The process for producing desacetyl 890A 1 which comprises intimately contacting 890A 1 with the enzyme N-acetylthienamycin amidohydrolase produced by an amidohydrolase-producing strain of the microorganism Protaminobacter ruber.
Claim 14
Dependent Claim
28 words
The process for producing desacetyl 890A 1 which comprises intimately contacting 890A 1 with the enzyme N-acetylthienamycin amidohydrolase produced by an amidohydrolase-producing strain of the microorganism Protaminobacter ruber.
Claim 15
Dependent Claim
28 words
The process for producing desacetyl 890A 3 which comprises intimately contacting 890A 3 with the enzyme N-acetylthienamycin amidohydrolase produced by an amidohydrolase-producing strain of the microorganism Protaminobacter ruber.
Claim 16
Dependent Claim
28 words
The process for producing desacetyl 890A 3 which comprises intimately contacting 890A 3 with the enzyme N-acetylthienamycin amidohydrolase produced by an amidohydrolase-producing strain of the microorganism Protaminobacter ruber.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-03 | 1985-02-02 | 1985-08-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-03 | 1989-02-02 | 1989-08-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-03 | 1993-02-02 | 1993-08-04 | $7700.00 | Window Closed / Lapsed |