US3886133A
Expired / Lapsed
US
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Process for preparing 3-aminopropyl ester of bleomycinic acid and bleomycinic acid including an acid salt and a copper complex thereof
Assignee: Microbial Chemistry Research Foundation
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Filing: 1973-02-20
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Granted: 1975-05-27
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Expires: 1993-02-20
Abstract
Abstract A process of preparing the 3-aminopropyl ester of bleomycinic acid or salts thereof and bleomycinic acid or salts thereof which comprises reacting 3-methylmercaptopropylamino bleomycin or acid salts thereof with a halide compound having the formula R-X, wherein R represents -CN, -CH2CO2H, - CH2CO2R1, -CH2CONH2 and WHEREIN R1 represents a lower alkyl group; and X represents a halogen atom in an acidic aqueous medium, and then hydrolyzing the resulting 3-aminopropyl ester of bleomycinic acid in an acidic medium if bleomycinic acid is the product desired.
Inventors
- 👤 Hamao Umezawa
- 👤 Tomohisa Takita
- 👤 Akio Fujii
- 👤 Takeyo Fukuoka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 20:19
CPC Classifications
C; C07; C07K; C07K9/00; C07K9/001; C07K9/003; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/19
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
64 words
A PROCESS FOR PREPARING A 3-AMINOPROPYL ESTER OF BLEOMYCINIC ACID OR AN ACID SALT THEREOF WHICH COMPRISES REACTING A 3-METHYL-MECAPTOPROPYLAMINOBLEMYCIN OR AN ACID SALT THEREOF AT THE MERCAPTO SULFUR ATOM WITH A HALIDE COMPOUND HAVING THE FORMULA: R-X WHEREIN R REPRESENTS -CN, -CH2COOH, -CH2COOR1, -CH2CONH2 AND 2,4-DI(O2N-)PHENYL; R1 REPRESENTS A LOWER ALKYL GROUP, AND X REPRESENTS A HALOGEN ATOM IN AN ACIDIC AQUEOUS MEDIUM.
Claim 2
Dependent Claim
64 words
A PROCESS FOR PREPARING A 3-AMINOPROPYL ESTER OF BLEOMYCINIC ACID OR AN ACID SALT THEREOF WHICH COMPRISES REACTING A 3-METHYL-MECAPTOPROPYLAMINOBLEMYCIN OR AN ACID SALT THEREOF AT THE MERCAPTO SULFUR ATOM WITH A HALIDE COMPOUND HAVING THE FORMULA: R-X WHEREIN R REPRESENTS -CN, -CH2COOH, -CH2COOR1, -CH2CONH2 AND 2,4-DI(O2N-)PHENYL; R1 REPRESENTS A LOWER ALKYL GROUP, AND X REPRESENTS A HALOGEN ATOM IN AN ACIDIC AQUEOUS MEDIUM.
Claim 3
Dependent Claim
33 words
The process of claim 1, wherein said 3-methylmercaptopropylaminobleomycin or an acid salt thereof is a copper complex, and said 3-aminopropyl ester of bleomycinic acid or an acid salt thereof is a copper complex.
Claim 4
Dependent Claim
31 words
The process of claim 1, wherein the 3-aminopropyl ester of bleomycinic acid or an acid salt thereof is isolated from the reaction products by treating said ester with an ion-exchange resin.
Claim 5
Dependent Claim
15 words
The process of claim 1, wherein said acidic medium contains hydrochloric acid or sulfuric acid.
Claim 6
Dependent Claim
26 words
The process of claim 1, wherein said acidic medium contains an organic acid selected from the group consisting of formic acid, acetic acid and trifluoroacetic acid.
Claim 7
Dependent Claim
31 words
The process of claim 1 wherein said acidic aqueous medium contains an organic solvent selected from the group consisting of methanol, ethanol, acetone, dioxane, dimethylsulfoxide, dimethylformamide and ethylene glycol monomethyl ether.
Claim 8
Dependent Claim
22 words
The process of claim 1, wherein 3-methylmercaptopropylaminobleomycin is reacted with said halide compound at 0* - 90* C. for 14- 48 hours.
Claim 9
Dependent Claim
19 words
The 3-aminopropyl ester of bleomycinic acid having the following formula, an acid salt thereof or a copper complex thereof:
Claim 10
Dependent Claim
19 words
The 3-aminopropyl ester of bleomycinic acid having the following formula, an acid salt thereof or a copper complex thereof:
Claim 11
Dependent Claim
38 words
A process for preparing bleomycinic acid which comprises reacting 3-methylmercaptopropylaminobleomycin or an acid salt thereof at the mercapto sulfur atom with a halide compound having the formula R - X wherein R represents -CN, -CH2COOH, -CH2COOR1, -CH2CONH2 and
Claim 12
Dependent Claim
38 words
A process for preparing bleomycinic acid which comprises reacting 3-methylmercaptopropylaminobleomycin or an acid salt thereof at the mercapto sulfur atom with a halide compound having the formula R - X wherein R represents -CN, -CH2COOH, -CH2COOR1, -CH2CONH2 and
Claim 13
Dependent Claim
31 words
The process of claim 9, wherein said acidic aqueous medium contains an organic solvent selected from the group consisting of methanol, ethanol, acetone, dioxane, dimethylsulfoxide, dimethylformamide and ethylene glycol monomethyl ether.
Claim 14
Dependent Claim
18 words
A process for preparing bleomycinic acid which comprises hydrolyzing 3-aminopropyl ester of bleomycinic acid in an acidic medium.
Claim 15
Dependent Claim
18 words
A process for preparing bleomycinic acid which comprises hydrolyzing 3-aminopropyl ester of bleomycinic acid in an acidic medium.
Claim 16
Dependent Claim
36 words
The process of claim 9, wherein said 3-aminopropyl ester of bleomycinic acid or an acid salt thereof is hydrolyzed at 40* -120* C for 1- 24 hours in an acidic medium having a pH of 2.-5.5.
Claim 17
Dependent Claim
21 words
The process of claim 9, wherein said 3-aminopropyl ester of bleomycinic acid or an acid salt thereof is a copper complex.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-05-26 | 1978-11-25 | 1979-05-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-05-26 | 1982-11-25 | 1983-05-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-05-26 | 1986-11-25 | 1987-05-27 | $7700.00 | Window Closed / Lapsed |