Claims
- 1. A demethylmaytansinoid compound of the formula: ##STR22## wherein X is Cl or H; R.sub.1 is H or an acyl group, the acyl group being represented by one of the formulae:
- --CO--R.sub.2 (a)
- wherein R.sub.2 is hydrogen, C.sub.1-18 alkyl, C.sub.2-18 alkenyl, C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkenyl, phenyl, a heterocyclic group selected from the class consisting of azetidinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1,2,3,4-tetrahydropyridyl, piperidyl, quinolyl, 1,2-dihydroquinolyl, 3-isoquinolyl, 4-isoquinolyl, 1,2-dihydroisoquinolyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, indolyl, furyl, pyranyl, dihydropyranyl, benzofuryl, benzopyranyl, thienyl, benzothienyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, 2-imidazolyl, imidazolidinyl, benzoimidazolyl, indazolyl, quinoxalkyl, quinazolinyl, cinnolinyl, 1,4-dioxanyl, 1,4-benzodioxanyl, 1,2-dithiolanyl, 1,3-dithiolanyl, 1,3-dithianyl, isooxazolyl, oxazolyl, morpholinyl, benzoisoxazolyl, benzoxazolyl, isothiazolyl, thiazolyl, benzoisothiazolyl, benzothiazolyl, benzothiazinyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,3,5-triazinyl, benzotriazolyl, and 1,2,3,4,-tetrazolyl, said cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being attached directly to the carbonyl carbon or through a C.sub.1-4 alkylene chain, said alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkoxy, C.sub.2-4 alkanoyl, C.sub.2-4 alkanoyloxy, C.sub.2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C.sub.1-4 -alkylamino, C.sub.1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C.sub.1-4 alkanoylamido, and said cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkyl; ##STR23## wherein R.sub.3 is hydrogen, C.sub.1-8 alkyl, C.sub.3-10 cycloalkyl, phenyl, indolyl, or imidazolyl group, said cycloalkyl, phenyl, indolyl or imidazolyl groups being attached directly to the alpha-carbon atom or through a C.sub.1-4 alkylene chain, said alkyl, cycloalkyl, phenyl, indolyl or imidazolyl being unsubstituted or substituted by C.sub.1-4 alkoxy, C.sub.2-4 alkanoyl, C.sub.2-4 alkanyloxy, C.sub.2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C.sub.1-4 alkylamino, C.sub.1-4 alkylthio, methyl- sulfinyl, methylsulfonyl, oxo, thioxo or C.sub.1-4 alkanoylamido, and said cycloalkyl, phenyl, indolyl or imidazolyl being unsubstituted or substituted by C.sub.1-4 alkyl;
- R.sub.4 is hydrogen, C.sub.1-18 alkyl, C.sub.3-10 cycloalkyl, C.sub.4-14 cycloalkylalkyl, phenyl or benzyl group, said alkyl, cycloalkyl, cycloalkylalkyl, phenyl or benzyl group being unsubstituted or substituted by C.sub.1-4 alkoxy, C.sub.2-4 alkanoyl, C.sub.2-4 alkanoyloxy, C.sub.2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C.sub.1-4 -alkylamino, C.sub.1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C.sub.1-4 alkanoylamido, and said cycloalkyl, cycloalkylalkyl, phenyl or benzyl group being unsubstituted or substituted by C.sub.1-4 alkyl;
- R.sub.5 is hydrogen, C.sub.1-7 alkoxy, bornyloxy, isobornyloxy, benzyloxy, C.sub.1-18 alkyl, C.sub.2-18 alkenyl, C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkenyl, phenyl or a heterocyclic group selected from the class consisting of azetidinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1,2,3,4-tetrahydropyridyl, piperidyl, quinolyl, 1,2-dihydroquinolyl, 3-isoquinolyl, 4-isoquinolyl, 1,2-dihydroisoquinolyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, indolyl, furyl, pyranyl, dihydropyranyl, benzofuryl, benzopyranyl, thienyl, benzothienyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, 2-imidazolyl, imidazolidinyl, benzoimidazolyl, indazolyl, quinoxalyl, quinozolinyl, cinnolinyl, 1,4-dioxanyl, 1,4-benzodioxanyl, 1,2-dithiolanyl, 1,3-dithiolanyl, 1,3-dithianyl, isooxazolyl, oxazolyl, morpholinyl, benzoisoxazolyl, benzoxazolyl, isothiazolyl, thiazolyl, benzoisothiazolyl, benzothiazolyl, benzothiazinyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,3,5-triazinyl, benzotriazolyl and 1,2,3,4-tetrazolyl, said cycloalkyl, cycloalkenyl, phenyl or heterocyclic groups being attached directly to the carbonyl carbon atom adjacent the nitrogen atom or through a C.sub.1-4 alkylene chain, said alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkoxy, C.sub.2-4 alkanoyl, C.sub.2-4 alkanoyloxy, C.sub.2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C.sub.1-4 -alkylamino, C.sub.1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C.sub.1-4 alkanoylamido, and said cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkyl; ##STR24## wherein R.sub.6 and R.sub.7 may be the same or different and each is hydrogen, C.sub.1-18 alkyl, C.sub.2-18 alkenyl, C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkenyl, C.sub.4-14 cycloalkylalkyl, C.sub.4-10 cycloalkenylalkyl, phenyl, phenyl-C.sub.1-14 alkyl, phenyl-C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkylphenyl, biphenyl or heterocyclic group selected from the class consisting of azetidinyl, pyrrolyl, furyl, thienyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyrazolyl, imidazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolyl, quinazolyl, quinoxalyl, indolyl, benzofuranyl and benzothienyl, and wherein R.sub.6 and R.sub.7 together may form a heterocyclic group of azetidinyl, pyrrolidinyl, piperidinyl or morpholinyl taken together with the adjacent nitrogen atom, these groups being unsubstituted or substituted by C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, phenoxy, phenylthio, cyclohexyloxy, halogen, cyano, C.sub.2-5 alkoxycarbonyl, benzyloxycarbonyl, nitro, aminosulfonyl, or di-C.sub.1-4 -alkylamino, and said cyclic moiety or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkyl; or
- --CO--O--R.sub.8 (d)
- wherein R.sub.8 is C.sub.1-18 alkyl, C.sub.3-10 cycloalkyl, phenyl or phenyl-C.sub.1-4 -alkyl, said groups being unsubstituted or substituted by C.sub.1-4 alkoxy, phenoxy, benzyloxy, halogen or cyano, and said cyclic moiety being unsubstituted or substituted by C.sub.1-4 alkyl, C.sub.3-10 -cycloalkyl, C.sub.3-10 -cycloalkenyl or phenyl.
- 2. A compound as claimed in claim 1, wherein R.sub.1 is an acyl group derived from a carboxylic acid, carbamic acid or half ester of carbonic acid derivative having a molecular weight of no more than about 300.
- 3. A compound as claimed in claim 1, wherein R.sub.1 is an acyl group derived from a carboxylic acid, carbamic acid or half ester of carbonic acid derivative having a molecular weight of no more than about 300 or an acyl group containing about 1 to about 20 carbon atoms.
- 4. A compound as claimed in claim 1, wherein R.sub.1 is an acyl group selected from the group consisting of saturated or unsaturated aliphatic acyl groups; saturated or unsaturated alicyclic acyl groups; aromatic acyl groups; saturated or unsaturated heterocyclic acyl groups; N-acyl-.alpha.-amino acid type acyl groups; carbamoyl type acyl groups, and an acyl group derived from half ester of carbonic acid.
- 5. A compound of claim 1, wherein X is Cl or H and R.sub.1 is an acyl group represented by the formula:
- --CO--R.sub.2
- wherein R.sub.2 is hydrogen, C.sub.1-6 alkyl, C.sub.2-4 alkenyl, C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkenyl, phenyl or a heterocyclic group selected from the class consisting of azetidinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1,2,3,4-tetrahydropyridyl, piperidyl, quinolyl, 1,2-dihydroquinolyl, 3-isoquinolyl, 4-isoquinolyl, 1,2-dihydroisoquinolyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, indolyl, furyl, pyranyl, dihydropyranyl, benzofuryl, benzopyranyl thienyl, benzothienyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, 2-imidazolyl, imidazolidinyl, benzoimidazolyl, indazolyl, quinoxalyl, quinazolinyl, cinnolinyl, 1,4-dioxanyl, 1,4-benzodioxanyl, 1,2-dithiolanyl, 1,3-dithiolanyl, 1,3-dithianyl, isooxazolyl, oxazolyl, morpholinyl, benzoisoxazolyl, benzoxazolyl, isothiazolyl, thiazolyl, benzoizothiazolyl, benzothiazolyl, benzothiazinyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,3,5-triazinyl, benzotriazolyl and 1,2,3,4-tetrazolyl, said cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being attached directly to the carbonyl carbon or through C.sub.1-4 alkylene chain, said alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkoxy, halogen, nitro, trifluoromethyl, and said cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkyl.
- 6. A compound of claim 1, wherein X is Cl or H and R.sub.1 is an acyl group represented by the formula: ##STR25## wherein R.sub.3 is hydrogen, C.sub.1-6 alkyl, C.sub.3-10 cycloalkyl, phenyl, indolyl or imidazolyl group, said cycloalkyl, phenyl, indolyl or imidazolyl group being attached directly to the alpha-carbon atom or through C.sub.1-4 alkylene chain, said alkyl, cycloalkyl, phenyl, indolyl or imidazolyl being unsubstituted or substituted by C.sub.1-4 alkoxy, halogen, nitro or trifluoromethyl, and said cycloalkyl, phenyl, indolyl or imidazolyl being unsubstituted or substituted by C.sub.1-4 alkyl;
- R.sub.4 is hydrogen, C.sub.1-16 alkyl, C.sub.3-10 cycloalkyl, C.sub.4-14 cycloalkylalkyl, phenyl or benzyl group, said alkyl, cycloalkyl, cycloalkylalkyl, phenyl or benzyl group being unsubstituted or substituted by C.sub.1-4 alkoxy, halogen, nitro, trifluoromethyl, and said cycloalkyl, cycloalkylalkyl, phenyl or benzyl group being unsubstituted or substituted by C.sub.1-4 alkyl;
- R.sub.5 is hydrogen, C.sub.1-7 alkoxy, bornyloxy, isobornyloxy, benzyloxy, C.sub.1-6 alkyl, C.sub.2-4 alkenyl, C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkenyl, phenyl or heterocyclic group selected from the class consisting of azetidinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1,2,3,4-tetrahydropyridyl, piperidyl, quinolyl, 1,2-dihydroquinolyl, 3-isoquinolyl, 4-isoquinolyl, 1,2-dihydroisoquinolyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, indolyl, furyl, pyranyl, dihydropyranyl, benzofuryl, benzopyranyl, thienyl, benzothienyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, 2-imidazolyl, imidazolidinyl, benzoimidazolyl, indazolyl, quinoxalyl, quinazolinyl, cinnolinyl, 1,4-dioxanyl, 1,4-benzodioxanyl, 1,2-dithiolanyl, 1,3-dithiolanyl, 1,3-dithianyl, isooxazolyl, oxazolyl, morpholinyl, benzoisoxazolyl, benzoxazolyl, isothiazolyl, thiazolyl, benzoisothiazolyl, benzothiazolyl, benzothiazinyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,3,5-triazinyl, benzotriazolyl and 1,2,3,4-tetrazolyl,
- said cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being attached directly to the carbonyl carbon atom adjacent the nitrogen atom or through C.sub.1-4 alkylene chain, said alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkoxy, halogen, nitro, trifluoromethyl, and said cycloalkyl, cycloalkenyl, phenyl or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkyl.
- 7. A compound of claim 1, wherein X is Cl or H and R.sub.1 is an acyl group represented by the formula: ##STR26## wherein R.sub.6 and R.sub.7 may be the same or different and each is hydrogen, C.sub.1-6 alkyl, C.sub.2-4 alkenyl, C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkenyl, C.sub.4-14 cycloalkylalkyl, C.sub.4-10 cycloalkenylalkyl, phenyl, benzyl, phenyl-C.sub.3-10 -cycloalkyl, C.sub.3-10 cycloalkyl-phenyl, biphenyl or a heterocyclic group selected from the class consisting of azetidinyl, pyrrolyl, furyl, thienyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolyl, quinazolyl, quinoxalyl, indolyl, benzofuranyl and benzothienyl, and wherein R.sub.6 and R.sub.7 together may form a heterocyclic group of azetidinyl, pyrrolidinyl, piperidinyl or morpholinyl when taken together with the adjacent nitrogen atom, said groups being unsubstituted or substituted by halogen or nitro, and said cyclic moiety or heterocyclic group being unsubstituted or substituted by C.sub.1-4 alkyl.
- 8. A compound as claimed in claim 1, wherein X is Cl or H and R.sub.1 is an acyl group represented by the formula:
- --CO--O--R.sub.8
- wherein R.sub.8 is C.sub.1-6 alkyl, C.sub.3-10 cycloalkyl, phenyl or benzyl, said groups being unsubstituted or substituted by C.sub.1-4 alkoxy or halogen, and said cyclic moiety being unsubstituted or substituted by C.sub.1-4 alkyl.
- 9. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytanacine.
- 10. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol propionate.
- 11. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-isobutyrate.
- 12. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-butyrate.
- 13. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-isovalerate.
- 14. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-valerate.
- 15. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-hexanoate.
- 16. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-heptanoate.
- 17. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-octanoate.
- 18. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-cyclohexanecarboxylate.
- 19. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-cyclopropanecarboxylate.
- 20. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-benzoate.
- 21. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-p-chlorobenzoate.
- 22. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-phenylacetate.
- 23. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-phenylpropionate.
- 24. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-nicotinate.
- 25. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-isonicotinate.
- 26. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-picolinate.
- 27. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(2-furan)-carboxylate.
- 28. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxydechloromaytansinol 3-phenylacetate.
- 29. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxydechloromaytansinol 3-isobutyrate.
- 30. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxydechloromaytansinol 3-cyclohexanecarboxylate.
- 31. A compound as claimed in claim 5, wherein the compound is 20-demethoxy-20-hydroxydechloromaytansinol 3-nicotinate.
- 32. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxydechloro-D-maytansine.
- 33. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxy-L-maytansine.
- 34. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxy-D-maytansine.
- 35. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxy-L-maytanprine.
- 36. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxy-D-maytanprine.
- 37. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxy-L-maytanbutine.
- 38. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxy-D-maytanbutine.
- 39. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxy-L-maytanvaline.
- 40. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxy-D-maytanvaline.
- 41. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(N-acetyl-N-benzyl)alanine ester.
- 42. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(N-acetyl-N-methyl)-L-leucine ester.
- 43. A compound as claimed in claim 6, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(N-acetyl-N-methyl)phenylalanine ester.
- 44. A compound as claimed in claim 7, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(N-methyl)-carbamate.
- 45. A compound as claimed in claim 7, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(N-butyl)-carbamate.
- 46. A compound as claimed in claim 7, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(N-phenyl)-carbamate.
- 47. A compound as claimed in claim 7, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(N-cyclohexyl)carbamate.
- 48. A compound as claimed in claim 7, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-(N-pyridyl)carbamate.
- 49. A compound as claimed in claim 8, wherein the compound is 20-demethoxy-20-hydroxymantansinol 3-isopropylcarbonate.
- 50. A compound as claimed in claim 8, wherein the compound is 20-demethoxy-20-hydroxydechloromaytansinol 3-benzylcarbonate.
- 51. A compound as claimed in claim 8, wherein the compound is 20-demethoxy-20-hydroxymaytansinol 3-phenylcarbonate.
- 52. A compound as claimed in claim 1, wherein the compound is 20-demethoxy-20-hydroxymantansinol.
- 53. A compound as claimed in claim 1, wherein the compound is 20-demethoxy-20-hydroxydechloromaytansinol.
Priority Claims (4)
Number |
Date |
Country |
Kind |
53-34645 |
Mar 1978 |
JPX |
|
53-160787 |
Dec 1978 |
JPX |
|
54-119959 |
Sep 1979 |
JPX |
|
2968 |
Aug 1979 |
KRX |
|
Parent Case Info
This Application is a continuation-in-part of Application Ser. No. 19,612, filed Mar. 12, 1979, now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3896111 |
Kupchan et al. |
Jul 1975 |
|
4137230 |
Hashimoto et al. |
Jan 1979 |
|
4162490 |
Higashide et al. |
Jul 1979 |
|
Non-Patent Literature Citations (1)
Entry |
Kupchan et al. "J. Med. Chem." vol. 21, No. 1, pp. 31-37 (1978). |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
19612 |
Mar 1979 |
|