PT95324A - Process for preparation of 20(S) or 20(RS)-camptothecins, the salts thereof, and pharmaceutical compositions that contain them, and for inhibition of the enzyme topoisomerase I - Google Patents
Process for preparation of 20(S) or 20(RS)-camptothecins, the salts thereof, and pharmaceutical compositions that contain them, and for inhibition of the enzyme topoisomerase IInfo
- Publication number
- PT95324A PT95324A PT9532490A PT9532490A PT95324A PT 95324 A PT95324 A PT 95324A PT 9532490 A PT9532490 A PT 9532490A PT 9532490 A PT9532490 A PT 9532490A PT 95324 A PT95324 A PT 95324A
- Authority
- PT
- Portugal
- Prior art keywords
- alkyl
- camptothecin
- amino
- group
- methylenedioxy
- Prior art date
Links
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to the process for preparation of a 20(S) or 20(RS) camptothecin having the structure shown below <IMAGE> in which Z is H or C1-8 alkyl and R is NO2, NH2, N3, H, halogen, COOH, OH, C1-3 O-alkyl, SH, C1-3 S-alkyl, CN, CH2NH2, C1-3 NH-alkyl, C1-3 CH2-NH-alkyl, N-(C1-3 alkyl)2, CH2N(C1-3 alkyl)2, O-, NH- or S-CH2CH2N(CH2CH2OH)2, O-, NH- or S-CH2CH2CH2N(CH2CH2OH)2, O-, NH- or S-CH2CH2N(CH2CH2CH2OH)2, O-, -NH- or S-CH2CH2CH2N(CH2CH2CH2OH2)2, O-, NH- or S-CH2CH2N(C1-3 alkyl)2, O-, NH- or S-CH2CH2CH2N(C1-3 alkyl)2, CHO, C1-3 alkyl or NHCOCHR1NR2R3, in which R1 is a side chain of an α-amino acid and R2 and R3 are, independently of each other, hydrogen or a lower alkyl group or R3 is a peptide unit containing l-3 amino acid units bound to nitrogen, via a peptide bond; NHCO-alkyleno-C2-8-X or NHCO-alkenyleno-C2-8-X, in which X is COOH, CONR2-(CH2)n- NR2R3, where n = 1-10 and R2 and R3 are defined as above; NHCO-B-(CH2)n-NR2R3, where B = oxygen or NH; or <IMAGE> where m + y = 3-6. The process involves, when appropriate: diazotizing a 9-amino-10,11-methylenedioxy-20(S)- or 20(RS)-camptothecin and displacing the diazo group with a corresponding nucleophil, or reducing the group R = CN; or alkylating the group R = OH, SH, NH2 or CH2NH2 with an alkylating agent; or reacting 10,11-methylenedioxy-20(S) or 20(RS)- camptothecin with a mixture of concentrated sulphuric and nitric acid; or nitrating 10,11-methylenedioxy-20(S)- or 20(RS)- camptothecin in order to obtain 9-nitro-10,11- methylenedioxy-20(S) or 20(RS)-camptothecin and then reducing the 9-nitro group; or reacting 9-amino or 9-amino-7-alkyl C1-8-10,11- methylenedioxy-20(S)- or 20(RS)-camptothecin with an amino acid with a protected amino group or peptide containing 1-4 amino acid units, a saturated or unsaturated C4-10 carboxylic acid anhydride or phosgene, and then with a primary or secondary straight, branched- chain or cyclic diamine, or with a tertiary amino- alcohol. The invention also relates to the process for preparation of salts of the abovementioned compounds, as well as the process for preparation of pharmaceutical compositions containing the compounds or salts.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US40777989A | 1989-09-15 | 1989-09-15 | |
US07/581,916 US5180722A (en) | 1987-04-14 | 1990-09-13 | 10,11-methylenedioxy-20(RS)-camptothecin and 10,11-methylenedioxy-20(S)-camptothecin analogs |
Publications (2)
Publication Number | Publication Date |
---|---|
PT95324A true PT95324A (en) | 1991-05-22 |
PT95324B PT95324B (en) | 1997-06-30 |
Family
ID=27020007
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PT9532490A PT95324B (en) | 1989-09-15 | 1990-09-14 | PREPARATION PROCEDURE OF 20 (S) OR 20 (RS) -CAMPTOTECINS, OF ITS SALTS AND INTERMEDIARIES AND OF PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU640950B2 (en) |
IE (1) | IE903347A1 (en) |
PT (1) | PT95324B (en) |
-
1990
- 1990-09-14 IE IE334790A patent/IE903347A1/en not_active IP Right Cessation
- 1990-09-14 PT PT9532490A patent/PT95324B/en not_active IP Right Cessation
- 1990-09-17 AU AU63404/90A patent/AU640950B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
PT95324B (en) | 1997-06-30 |
AU640950B2 (en) | 1993-09-09 |
AU6340490A (en) | 1991-04-18 |
IE903347A1 (en) | 1991-04-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
BB1A | Laying open of patent application |
Effective date: 19910115 |
|
FG3A | Patent granted, date of granting |
Effective date: 19970320 |
|
MM4A | Annulment/lapse due to non-payment of fees;searched & examined patent |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20090921 |