Claims
- 1. A compound of the formula: ##STR8## wherein R.sup.1 is 2-methyl-1-propenyl group or isobutyl group;
- R.sup.2 is
- (1) hydrogen atom,
- (2) a C.sub.1-20 alkyl group which may be substituted with (i) amino, (ii) C.sub.1-6 alkylamino, (iii) di-C.sub.1-6 alkylamino, (iv) nitro, (v) halogen, (vi) hydroxyl, (vii) C.sub.1-6 alkylthio, (viii) C.sub.1-6 alkoxycarbonyl, (xiii) carboxy-C.sub.1-6 carbamoyl, (ix) carboxyl, (xii) C.sub.1-6 alkoxycarbonyl, (xiii) carboxy-C.sub.1-6 alkoxy, (xiv) phenyl which may be substituted by (a) C.sub.1-6 alkyl, (b) C.sub.1-6 alkoxy, (c) halogen, (d) halogenated alkyl or (e) nitro, or
- (3) a C.sub.6-12 aryl group which may be substituted with (i) C.sub.2-6 alkyl, (ii) amino, (iii) halogen, (iv) hydroxyl, (v) C.sub.1-6 alkoxy, (vi) cyano, (vii) carbamoyl or (viii) carboxyl;
- R.sup.3 is
- (1) hydrogen atom,
- (2) a C.sub.1-20 alkyl group which may be substituted with (i) amino, (ii) C.sub.1-6 alkylamino, (iii) di-C.sub.1-6 alkylamino, (iv) nitro, (v) halogen, (vi) hydroxyl, (vii) C.sub.1-6 alkylthio, (viii) C.sub.1-6 alkoxy, (ix) cyano, (x) carbamoyl, (xi) carboxyl, (xii) C.sub.1-6 alkoxycarbonyl, (xiii) carboxy-C.sub.1-6 alkoxy, (xiv) phenyl which may be substituted by (a) C.sub.1-6 alkyl, (b) C.sub.1-6 alkoxy, (c) halogen, (d) halogenated alkyl or (e) nitro, or (xv) a 5- to 6-membered aromatic heterocyclic group containing 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and the said alkyl group may be epoxidated at an optional position,
- (3) a C.sub.2-20 alkanoyl group which may be substituted with (i) amino, (ii) C.sub.1-6 alkylamino, (iii) di-C.sub.1-6 alkylamino, (iv) nitro, (v) halogen, (vi) hydroxyl, (vii) C.sub.1-6 alkylthio, (viii) C.sub.1-6 alkoxy, (ix) cyano, (x) carbamoyl, (xi) carboxyl, (xii) C.sub.1-6 alkoxycarbonyl, (xiii) carboxy-C.sub.1-6 alkoxy, (xiv) phenyl which may be substituted by (a) C.sub.1-6 alkyl, (b) C.sub.1-6 alkoxy, (c) halogen, (d) halogenated alkyl or (e) nitro, or (xv) a 5- to 6-membered aromatic heterocyclic group containing 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur,
- (4) a C.sub.6-10 aroyl group which may be substituted with (i) C.sub.2-6 alkyl, (ii) amino, (iii) halogen, (iv) hydroxyl, (v) C.sub.1-6 alkoxy, (vi) cyano, (vii) carbamoyl or (viii) carboxyl,
- (5) carbamoyl group which may be substituted with Ii) C.sub.1-6 alkyl, (ii) C.sub.1-6 alkanoyl, (iii) halogeno-C.sub.1-6 alkanoyl, (iv) C.sub.1-6 alkoxycarbonylmethyl, (v) carboxymethyl, (vi) phenyl which may be substituted by (a) C.sub.1-6 alkyl, (b) C.sub.1-6 alkoxy, (c) halogen, (d) halogenated alkyl or (e) nitro, (vii) naphthyl, (viii) benzoyl, (ix) naphthoyl or (x) substituents forming cyclic amino group, taken together with the nitrogen atom of the carbamoyl group,
- (6) benzenesulfonyl group which may be substituted with (i) C.sub.1-6 alkyl or (ii) halogen,
- (7) a C.sub.1-6 alkylsulfonyl group which may be substituted with the same substituents(s) as those of substituted C.sub.2-20 alkanoyl group mentioned in above (3),
- (8) thiocarbamoyl group which may be substituted with the same substituents(s) as those of a substituted carbamoyl group mentioned in above (5),
- (9) a C.sub.1-6 alkoxycarbonyl group which may be substituted with the same substituent(s) as those of a substituted C.sub.2-20 alkanoyl group mentioned in above (3),
- (10) phenoxycarbonyl group which may be substituted with the same substituent(s) as those of a substituted benzenesulfonyl group mentioned in above (6), or
- (11) a 5- or 6-membered aromatic heterocyclic carbonyl group containing 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur which may be substituted with the same substituent(s) as those of a substituted C.sub.6-10 aroyl group mentioned in above (4), wherein said aromatic heterocyclic carbonyl group is selected from the group consisting of 2-furoyl, 2-thenoyl, nicotinoyl and isonicotinoyl;
- R.sup.2 and R.sup.3 may form pyrolidine, piperidine or isoindoline ring which may be substituted with C.sub.1-3 alkyl or oxo; and the bonding mark .about. represents an .alpha.-linkage or .beta.-linkage, or a salt thereof.
- 2. The compound as claimed in claim 1, wherein R.sup.1 is 2-methyl-1-propenyl group.
- 3. The compound as claimed in claim 1, wherein R.sup.2 is hydrogen; C.sub.1-6 alkyl which may be substituted with phenyl or naphthyl.
- 4. The compound as claimed in claim 1, wherein R.sup.3 is hydrogen; C.sub.2-8 alkanoyl which may be substituted with carboxy; benzoyl or naphthoyl which may be substituted with carboxy; carbamoyl which may be substituted with C.sub.1-6 alkyl, C.sub.1-6 alkanoyl, halogeno C.sub.1-6 alkanoyl, C.sub.1-6 alkoxycarbonylmethyl, phenyl, benzoyl or naphthoyl; benzenesulfonyl which may be substituted with C.sub.1-3 alkyl or halogen; C.sub.1-6 alkylsulfonyl; or thiocarbamoyl which may be substituted with C.sub.1-6 alkyl, C.sub.1-6 alkanoyl, halogeno C.sub.1-6 alkanoyl, C.sub.1-6 alkoxycarbonylmethyl, phenyl, benzoyl or naphthoyl.
- 5. The compound as claimed in claim 1, wherein R.sup.1 is 2-methyl-1-propenyl, R.sup.2 is hydrogen and R.sup.3 is carbamoyl which may be substituted with halogeno C.sub.1-6 alkanoyl.
- 6. The compound as claimed in claim 1, which is 6-.alpha.-(N'-chloroacetylureido)-6-desoxyfumagillol.
- 7. The compound as claimed in claim 1, which is 6-.alpha.-ureido-6-desoxyfumagillol.
- 8. A pharmaceutical composition for inhibiting angiogenesis which comprises an effective amount of the compound as claimed in claim 1 and a pharmaceutically acceptable carrier, diluent or excipent.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1-53535 |
Mar 1989 |
JPX |
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Parent Case Info
This is a continuation of copending application Ser. No. 07/489,370 filed on Mar. 6, 1990, now abandoned.
Foreign Referenced Citations (1)
Number |
Date |
Country |
1918794 |
Nov 1969 |
DEX |
Non-Patent Literature Citations (4)
Entry |
J. A. DiPaolo, et al., Antibiotics Annual (1958-1959), pp. 541-546. |
Journal of American Chem. Society, vol. 83, pp. 3096-3113 (1961). |
The Journal of Antibiotics, vol. 41, pp. 999-1008 (1988). |
Chemical Abstract, 106:176153y, 1987. |
Continuations (1)
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Number |
Date |
Country |
Parent |
489370 |
Mar 1990 |
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