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US4760136A
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Chartreusin derivatives and salts thereof
Assignee: Ishihara Sangyo Kaisha Ltd
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Filing: 1985-04-23
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Granted: 1988-07-26
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Expires: 2005-04-23
Abstract
Abstract This invention relates to a novel chartreusin derivative of the general formula (I): ##STR1## and a salt thereof. This chartreusin derivative and a salt thereof have an excellent antitumor activity, which is exhibited even when the site of cancer inoculation and the site of drug administration are different. This invention further relates to a antitumorous composition containing the above-mentioned compound as active ingredient. This invention furthermore relates to a process for producing the above-mentioned chartreusin derivative or salt thereof.
Inventors
- 👤 Hiroyuki Mori
- 👤 Nobutoshi Yamada
- 👤 Hideo Sugi
- 👤 Kenji Kon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:21
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; A; A61; A61K; A61K31/00; A61K31/70
Claims Analysis
Total Claims: 55
Claim 1
Independent Claim
1092 words
A chartreusin derivative fo the formula (I) or a salt thereof: ##STR172## wherein X 1 is a hydrogen atom or a C 1-3 alkyl group which may be substituted by a halogen atom, a C 1-2 alkoxy group, or a C 1-2 alkylthio group; X 2 is a C 1-3 alkyl group which may be substituted by a halogen atom or a C 1-2 alkoxy group or a C 1-2 alkylthio group, a C 1-2 alkylcarbonyl-C 1-2 alkyl group which may be substituted by a halogen atom, a pheynyl group, a phenyl-C 1-2 alkyl group, a furyl group, or a thienyl group wherein each of the phenyl group, the phenyl-C 1-2 alkyl group, the furyl group and the thienyl group may be subsituted by a halogen atom, a cyano group, a nitro group, a C 1-3 alkyl group, a C 1-3 alkoxy group, a C 1-3 alkylthio group, a C 1-3 alkycarbonyl group, a C 1-3 alkoxycarbonyl group or a di-C 1-3 alkylamino group wherein each of the C 1-3 alkyl group, the C 1-3 alkoxy group, the C 1-3 alkylthio group, the C 1-3 alkylcarbonyl group, the C 1-3 alkoxycarbonyl group and the di-C 1-3 alkylamino group may be substituted by a halogen atom; in the case where both X 1 and X 2 are said alkyl groups, the total number of carbon atoms of these alkyl groups is 4 or less; X 1 is a hdyrogen atom in the case where X 2 is said phenyl group, said phenyl-C 1-2 alkyl group, said furyl group, or said thienyl group; X 1 and X 2 , when taken together with the adjacent carbon atom, may form a C 3-7 cycloalkylidene which may be substituted by a halogen atom, a C 1-2 alkoxy group or a C 1-2 alkylthio group; and Q is ##STR173## wherein each of R, R' and R" is a C 1-11 alkanediyl group, a C 2-11 alkenediyl group, a C 2-11 alkynediyl group, a C 3-10 cycloalkanediyl group, a C 5-10 cycloalkenediyl group wherein each of the C 1-11 alkanediyl group, the C 2-11 alkenediyl group, the C 2-11 alkynediyl group, the C 3-10 cycloalkanediyl group and the C 5-10 cycloalkenediyl group may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, an aminocarbonyl group, a hydroxycarbonyl group, a C 1-5 alkoxycarbonyl group, a phenyl group which may be sbustituted by a halogen atom or a hydroxyl group or a mercapto group or a C 1-3 alkoxy group or a C 1-3 alkylthio group, or a 3-indolyl group which may be substittued by a halogen atom, or each of R, R' and R" is a phenylene group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, an aminocarbonyl group, a hydroxycarbonyl group, or a C 1-5 alkoxycarbonyl group;, atom, or each of Z 1 , Z' 1 and Z" 1 is a hydrogen atom, on a C 1-6 alkyl group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-3 alkoxy group, or a C 1-3 alkylthio group; Z 2 is a hydrogen atom, a formyl group, a C 1-6 alkyl group, a C 1-6 alkylcarbonyl group, a benzoyl group wherein each of the C 1-6 alkyl group, the C 1-6 alkylcarbonyl group and the benzoyl group may be substituted by the same substituent as substituent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z" l , or Z 2 is a benzyloxycarbonyl group which may be substituted by a halogen atom; Z 1 and Z 2 , when taken together with the nitrogen atom, may form a nitrogen-containing C 2-10 heterocyclic group which may be substituted by the same substituent as substituent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z" 1 , or Q is a C 1-11 alkyl group, a C 2-11 alkenyl group, a C 3-11 alkynyl group, a C 3-10 cycloalkyl group, a C 5-10 cycloalkenyl group, a C 1-10 alkylcarbonyl group, a C 1-10 alkoxycarbonyl group wherein each of the C 1-11 alkyl group, the C 2-11 alkenyl group, the C 3-11 alkynyl group, the C 3-10 cycloalkyl group, the C 5-10 cycloalkenyl group, the C 1-10 alkylcarbonyl group and the C 1-10 alkoxycarbonyl group may be substituted by a halogen atom a hydroxyl group, a mercapto group, a cyano group, a nitro group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, a phenoxycarbonyl group, a C 1-6 alkylcarbonyloxy group, a C 3-7 cycloakyl group, a phenyl group, a phenoxy group, a phenylthio group, a phenylsulfinyl group, a phenylsulfonyl group, a benzoyl group, a benzolyoxy group or a benzyloxy group wherein each of the C 1-6 alkoxy group, the C 1-6 alkylthio group, the C 1-6 alkylsulfinyl group, the C 1-6 alkylsulfonyl group, the C 1-6 alkylcarbonyl group, the C 1-6 alkoxycarbonyl group, the phenoxycarbonyl group, the C 1-6 alkylcarbonyloxy group, the C 3-7 cycloalkyl group, the phenyl group, the phenyoxy group, the phenylthio group, the phenylsulfinyl group, the phenylsulfonyl group, the benzoyl group, the benzoyloxy group, and benzyloxy group may be substituted by the same substituent as substituted for said C 1-6 alkyl group as each of Z 1 , Z' 1 , and Z 1 ", or Q is a phenyl group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a nitro group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alkyl group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, or a C 1-6 alkylcarbonyloxy group wherein each of the C 1-6 alkyl group, the C 1-6 alkoxy group, the C 1-6 alkylthio group, the C 1-6 alkylcarbonyl group, the C 1-6 alkoxycaronyl group, and the C 1-6 alkylcarbonyloxy group may be substituted by the same substituent as substituent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z 1 ", the total number of atoms of Q other than hydrogen atom being 30 or less.
Claim 2
Dependent Claim
1092 words
A chartreusin derivative fo the formula (I) or a salt thereof: ##STR172## wherein X 1 is a hydrogen atom or a C 1-3 alkyl group which may be substituted by a halogen atom, a C 1-2 alkoxy group, or a C 1-2 alkylthio group; X 2 is a C 1-3 alkyl group which may be substituted by a halogen atom or a C 1-2 alkoxy group or a C 1-2 alkylthio group, a C 1-2 alkylcarbonyl-C 1-2 alkyl group which may be substituted by a halogen atom, a pheynyl group, a phenyl-C 1-2 alkyl group, a furyl group, or a thienyl group wherein each of the phenyl group, the phenyl-C 1-2 alkyl group, the furyl group and the thienyl group may be subsituted by a halogen atom, a cyano group, a nitro group, a C 1-3 alkyl group, a C 1-3 alkoxy group, a C 1-3 alkylthio group, a C 1-3 alkycarbonyl group, a C 1-3 alkoxycarbonyl group or a di-C 1-3 alkylamino group wherein each of the C 1-3 alkyl group, the C 1-3 alkoxy group, the C 1-3 alkylthio group, the C 1-3 alkylcarbonyl group, the C 1-3 alkoxycarbonyl group and the di-C 1-3 alkylamino group may be substituted by a halogen atom; in the case where both X 1 and X 2 are said alkyl groups, the total number of carbon atoms of these alkyl groups is 4 or less; X 1 is a hdyrogen atom in the case where X 2 is said phenyl group, said phenyl-C 1-2 alkyl group, said furyl group, or said thienyl group; X 1 and X 2 , when taken together with the adjacent carbon atom, may form a C 3-7 cycloalkylidene which may be substituted by a halogen atom, a C 1-2 alkoxy group or a C 1-2 alkylthio group; and Q is ##STR173## wherein each of R, R' and R" is a C 1-11 alkanediyl group, a C 2-11 alkenediyl group, a C 2-11 alkynediyl group, a C 3-10 cycloalkanediyl group, a C 5-10 cycloalkenediyl group wherein each of the C 1-11 alkanediyl group, the C 2-11 alkenediyl group, the C 2-11 alkynediyl group, the C 3-10 cycloalkanediyl group and the C 5-10 cycloalkenediyl group may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, an aminocarbonyl group, a hydroxycarbonyl group, a C 1-5 alkoxycarbonyl group, a phenyl group which may be sbustituted by a halogen atom or a hydroxyl group or a mercapto group or a C 1-3 alkoxy group or a C 1-3 alkylthio group, or a 3-indolyl group which may be substittued by a halogen atom, or each of R, R' and R" is a phenylene group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, an aminocarbonyl group, a hydroxycarbonyl group, or a C 1-5 alkoxycarbonyl group;, atom, or each of Z 1 , Z' 1 and Z" 1 is a hydrogen atom, on a C 1-6 alkyl group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-3 alkoxy group, or a C 1-3 alkylthio group; Z 2 is a hydrogen atom, a formyl group, a C 1-6 alkyl group, a C 1-6 alkylcarbonyl group, a benzoyl group wherein each of the C 1-6 alkyl group, the C 1-6 alkylcarbonyl group and the benzoyl group may be substituted by the same substituent as substituent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z" l , or Z 2 is a benzyloxycarbonyl group which may be substituted by a halogen atom; Z 1 and Z 2 , when taken together with the nitrogen atom, may form a nitrogen-containing C 2-10 heterocyclic group which may be substituted by the same substituent as substituent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z" 1 , or Q is a C 1-11 alkyl group, a C 2-11 alkenyl group, a C 3-11 alkynyl group, a C 3-10 cycloalkyl group, a C 5-10 cycloalkenyl group, a C 1-10 alkylcarbonyl group, a C 1-10 alkoxycarbonyl group wherein each of the C 1-11 alkyl group, the C 2-11 alkenyl group, the C 3-11 alkynyl group, the C 3-10 cycloalkyl group, the C 5-10 cycloalkenyl group, the C 1-10 alkylcarbonyl group and the C 1-10 alkoxycarbonyl group may be substituted by a halogen atom a hydroxyl group, a mercapto group, a cyano group, a nitro group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, a phenoxycarbonyl group, a C 1-6 alkylcarbonyloxy group, a C 3-7 cycloakyl group, a phenyl group, a phenoxy group, a phenylthio group, a phenylsulfinyl group, a phenylsulfonyl group, a benzoyl group, a benzolyoxy group or a benzyloxy group wherein each of the C 1-6 alkoxy group, the C 1-6 alkylthio group, the C 1-6 alkylsulfinyl group, the C 1-6 alkylsulfonyl group, the C 1-6 alkylcarbonyl group, the C 1-6 alkoxycarbonyl group, the phenoxycarbonyl group, the C 1-6 alkylcarbonyloxy group, the C 3-7 cycloalkyl group, the phenyl group, the phenyoxy group, the phenylthio group, the phenylsulfinyl group, the phenylsulfonyl group, the benzoyl group, the benzoyloxy group, and benzyloxy group may be substituted by the same substituent as substituted for said C 1-6 alkyl group as each of Z 1 , Z' 1 , and Z 1 ", or Q is a phenyl group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a nitro group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alkyl group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, or a C 1-6 alkylcarbonyloxy group wherein each of the C 1-6 alkyl group, the C 1-6 alkoxy group, the C 1-6 alkylthio group, the C 1-6 alkylcarbonyl group, the C 1-6 alkoxycaronyl group, and the C 1-6 alkylcarbonyloxy group may be substituted by the same substituent as substituent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z 1 ", the total number of atoms of Q other than hydrogen atom being 30 or less.
Claim 3
Dependent Claim
15 words
A chartreusin derivative or a salt thereof according to claim 1 wherein Q is ##STR174##
Claim 4
Dependent Claim
64 words
A chartreusin derivative or a salt thereof according to claim 1 wherein X 1 is a hydrogen atom; X 2 is said phenyl group, said furyl group, or said thienyl group; each of R, R' and R" is said C 1-11 alkanediyl group or said C3-10 cycloalkanediyl group; and the total number of atoms of Q other than hydrogen atom is 20 or less.
Claim 5
Dependent Claim
18 words
A chartreusin derivative or a salt thereof according to claim 3, wherein X 2 is said phenyl group.
Claim 6
Dependent Claim
51 words
A chartreusin derivative or a salt thereof according to calim 4 wherein X 2 is said phenyl group which may be substituted in the o-position, the m-position or the o-, m-positions of the benzene nucleus; and the total number of atoms of Q other than hydrogen atom is 15 or less.
Claim 7
Dependent Claim
51 words
A chartreusin derivative or a salt thereof according to calim 4 wherein X 2 is said phenyl group which may be substituted in the o-position, the m-position or the o-, m-positions of the benzene nucleus; and the total number of atoms of Q other than hydrogen atom is 15 or less.
Claim 8
Dependent Claim
16 words
A chartreusin derivative or a salt thereof acording to claim 5, which is in exo form.
Claim 9
Dependent Claim
32 words
A chartreusin derivative or salt thereof according to claim 6, wherein X 2 is a phenyl group which may be substituted by a fluorine atom in the m-position of the benzene nucleus.
Claim 10
Dependent Claim
17 words
A chartreusin derivative or salt thereof according to claim 78 wherein X 2 is a phenyl group.
Claim 11
Dependent Claim
48 words
A chartreusin derivative according to claim 1, wherein Q is said C 1-11 alkyl group, said C 2-11 alkenyl group, said C 3-11 alknyl group, said C 3-10 cycloalkyl group, said C 5-10 cycloalkenyl group, said C 1-10 alkylcarbonyl group, said C 1-10 alkoxycarbonylgroup or said phenyl group.
Claim 12
Dependent Claim
64 words
A chartreusin derivative according to claim 1, wherein X 1 is a hydrogne atom; X 2 is said phenyl group, said furyl group, or said thienyl group; and Q is said C 1-11 alkyl group, said C 2-11 alkenyl group, said C 3-10 cycloalkyl group or said phenyl group, the total number of atoms of Q other than hydrogen atom being 20 or less.
Claim 13
Dependent Claim
27 words
A chartreusin derivative according to claim 10, wherein X 2 is said phenyl group; Q is said C 1-11 alkyl group or said C 3-10 cycloalkyl group.
Claim 14
Dependent Claim
45 words
A chartreusin derivative according to claim 11, wherein X 2 is said phenyl group which may be substituted in the o-position, m-position, or o-, m-positions of the benzene nucleus; and the total number of atoms of Q other than hydrogen atom is 15 or less.
Claim 15
Dependent Claim
13 words
A chartreusin derivative according to claim 12, which is in the exo form.
Claim 16
Dependent Claim
29 words
A chartreusin derivative according to claim 13 wherein X 2 is a phenyl group which may be substituted by a flourine atom in the m-position for the benzene nucleus.
Claim 17
Dependent Claim
13 words
A chartreusin derivative according to claim 14, wherein X 2 is phenyl group.
Claim 18
Dependent Claim
21 words
A chartreusin derivative or a salt thereof ccording to claim 2, wherein the derivative is the exo form of 6-O-(N,N-dimethyl-β-amino-isobutyryl)-3', 4'-O-benzylidene-chartreusin.
Claim 19
Dependent Claim
21 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(N-isopropyl-β-amino-isobutyryl)-3', 4'-O-benzylindene-chartreusin.
Claim 20
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(N-glycyl-β-amino-isobutyryl)-3',4'-O-benzylidene-chartreusin.
Claim 21
Dependent Claim
19 words
A chartreusin derivative or a salt thereof according,to claim 2, wherein the derivative is the exo form of 6-O-[N-(N',N'-dimethyl-glycyl)-]-amino-isobutyryl]-3',4'-O-benzylidene-chartreusin.
Claim 22
Dependent Claim
22 words
A chartreusin derivative or a salt thereof 6-O-(β-amino-isobutyryl)-3',''-O- enzylidene-chartreusin. according to claim 2, wherein the derivative is the exo form of 6-O-(β-amino-isobutryl)3',4'-O-benzylidene-chartreusin.
Claim 23
Dependent Claim
20 words
Achartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(N,N-diethyl-β-alanyl)-3', 4'-O-benzylidene-chartreusin.
Claim 24
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(β-1-pyrrolidinyl-propionyl)-3',4'-O-benzylidene-chartreusin.
Claim 25
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(N-glycyl-β-alanyl)-3',4'-O-benzylidene-chartreusin.
Claim 26
Dependent Claim
16 words
A chartreusin derivative according to claim 2, wherein the derivative is the exo form of 6-O-(N-trifluoroacetyl-β-amino-isobutyrl)-3',4'-O-benzylidene-chartreusin.
Claim 27
Dependent Claim
16 words
A chartreusin derivative according to claim 2, wherein the derivative is the exo form of 6-O-(N-benzoyl-β-aminoisobutyryl)-3',4'-O-benzylidene-chartreusin.
Claim 28
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(β-amino-isobutyryl)-3',4',-O-(m-fluorobenzylidene)-chartreusin.
Claim 29
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(β-alanyl)-3',4'-O-benzylidene-chartreusin.
Claim 30
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(β-morpholino-propionyl)-3',4'-O-benzylidene-chartreusin.
Claim 31
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(N,N-dimethyl-α-ethyl-propionyl)-3',4'-O-benzylindene-chartreusin.
Claim 32
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(N,N-dimetyl-β-alanyl)-3',4'-O-benzylidene-chartreusin.
Claim 33
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(N-methyl-β-amino-isobutyryl)-3',4'-O-benzylidene-chartreusin.
Claim 34
Dependent Claim
20 words
A chartreusin derivative or a salt thereof according to claim 2, wherein the derivative is the exo form of 6-O-(N-methyl-β-alanyl)-3',4'-O-benzylidene-chartreusin.
Claim 35
Dependent Claim
16 words
A chartreusin derivative according to claim 9, wherein the, derivative is the exo form of 6-O-(4-hydroxy-n-butyryl)-3',4'-O-benzylidene-chartreusin.
Claim 36
Dependent Claim
17 words
A chartreusin derivative according to claim 9, wherein the derivative is the exo form of 6-O-(2-acetoxyacetyl)-3', 4'-O-benzylidene-chartreusin.
Claim 37
Dependent Claim
16 words
A chartreusin derivative according to claim 9, wherein the derivative is the exo form of 6-O-[2-(3-chloropropionyloxy)-acetyl]-3',4'-O-benzylidene-chartreusin.
Claim 38
Dependent Claim
16 words
A chartreusin derivative according to claim 9, wherein the derivative is the exo form of 6-O-(3-methanesulfinyl-propionyl)-3',4'-O-benzylidene-chartreusin.
Claim 39
Dependent Claim
17 words
A chartreusin derivative according to claim 9, wherein the derivative is the exo form of 6-O-(3-methyl-carbonylpropionyl)-3', 4'-O-benzylidene-chartreusin.
Claim 40
Dependent Claim
17 words
A chartreusin derivative according to claim 9, wherein the derivative is the exo form of 6-O-(3-phenylpropionyl)-3', 4'-O-benzylidene-chartreusin.
Claim 41
Dependent Claim
16 words
A chartreusin derivative according to claim 9, wherein the derivative is the exo form of 6-O-(3-methyl-n-butyryl)-3',4'-O-benzylidene-chartreusin.
Claim 42
Dependent Claim
335 words
A chartreusin derivative, as an intermediate, of the formula: ##STR175## wherein X 1 is a hydrogen atom or a C 1-3 alkyl group which may be substituted by a halogen atom, a C 1-2 alkoxy group, or a C 1-2 alkylthio group; X 2 is a C 1-3 alkyl group which may be substituted by a halogen atom or a C 1-2 alkoxy group or a C 1-2 alkylthio group, a C 1-2 alkylcarbonyl-C 1-2 alkyl group which may be substituted by a halogen atom, a phenyl group, a phenyl-C 1-2 alkyl group, a furyl group or a thienyl group wherein each of the phenyl group, the phenyl-C 1-2 alkyl group, the fury group and the thienyl group may be substituted by a halogen atom, a cyano group, a nitro group, a C 1-3 alkyl group, a C 1-3 alkoxy group, a C 1-3 alkylthio group, a C 1-3 alkycarbonyl group, a C 1-3 alkoxycarbonyl group or a di-C 1-3 alkylamino group wherein each of the C 1-3 alkyl group, the C 1-3 alkoxy group, the C 1-3 akylthio group, the C 1-3 alkylcarbonyl group, the C 1-3 alkoxycarbonyl group and the di-C 1-3 akylamino group may be substituted by a halogen atom; in the case where, both X 1 and X 2 are said alkyl groups, the total number of carbon atoms of these alkyl groups is 4 or less; X 1 is a hydrogen atom in the case where X 2 is said phenyl group, said phenyl-C 1-2 alkyl group, said furyl group, or said thienyl group; X 1 and X 2 , when taken together with the adjacent carbon atom, may form a C 3-7 cycloalkylidene which may be substituted by a halogen atom, a C 1-2 alkoxy group or a C 1-2 alkylthio group; each of T 1 and T 2 is a hydrogen atom or a silyl group substituted by a text-butyl dimetyl group, T 1 being said silyl group in the case where T 2 is said silyl group.
Claim 43
Dependent Claim
335 words
A chartreusin derivative, as an intermediate, of the formula: ##STR175## wherein X 1 is a hydrogen atom or a C 1-3 alkyl group which may be substituted by a halogen atom, a C 1-2 alkoxy group, or a C 1-2 alkylthio group; X 2 is a C 1-3 alkyl group which may be substituted by a halogen atom or a C 1-2 alkoxy group or a C 1-2 alkylthio group, a C 1-2 alkylcarbonyl-C 1-2 alkyl group which may be substituted by a halogen atom, a phenyl group, a phenyl-C 1-2 alkyl group, a furyl group or a thienyl group wherein each of the phenyl group, the phenyl-C 1-2 alkyl group, the fury group and the thienyl group may be substituted by a halogen atom, a cyano group, a nitro group, a C 1-3 alkyl group, a C 1-3 alkoxy group, a C 1-3 alkylthio group, a C 1-3 alkycarbonyl group, a C 1-3 alkoxycarbonyl group or a di-C 1-3 alkylamino group wherein each of the C 1-3 alkyl group, the C 1-3 alkoxy group, the C 1-3 akylthio group, the C 1-3 alkylcarbonyl group, the C 1-3 alkoxycarbonyl group and the di-C 1-3 akylamino group may be substituted by a halogen atom; in the case where, both X 1 and X 2 are said alkyl groups, the total number of carbon atoms of these alkyl groups is 4 or less; X 1 is a hydrogen atom in the case where X 2 is said phenyl group, said phenyl-C 1-2 alkyl group, said furyl group, or said thienyl group; X 1 and X 2 , when taken together with the adjacent carbon atom, may form a C 3-7 cycloalkylidene which may be substituted by a halogen atom, a C 1-2 alkoxy group or a C 1-2 alkylthio group; each of T 1 and T 2 is a hydrogen atom or a silyl group substituted by a text-butyl dimetyl group, T 1 being said silyl group in the case where T 2 is said silyl group.
Claim 44
Dependent Claim
20 words
A chartreusin derivative as an intermediate according to claim 40, wherein both T 1 and T 2 are hydrogen atoms.
Claim 45
Dependent Claim
30 words
A chartreusin derivative as an intermediate according to claim 40 wherein X 1 is a hydrogen atom; X 2 is said phenyl group, said furyl group, or said thienyl group.
Claim 46
Dependent Claim
17 words
A chartreusin derivative as an intermediate according to claim 42, wherein X 2 is said phenyl group.
Claim 47
Dependent Claim
38 words
A chartreusin derivative as an intermediate according to claim 43, which is in the exo form and wherein X 2 is said phenyl group which may be substituted in the o-position, m-position or o-,m-positions of the benzene nucleus.
Claim 48
Dependent Claim
28 words
A chartreusin derivative as an intermediate according to claim 44 wherein X 2 is said phenyl group which may be substituted in the m-position of the benzene nucleus.
Claim 49
Dependent Claim
17 words
A chartreusin derivatie as an intermediate according to claim 45 wherein X 2 is a phenyl group.
Claim 50
Dependent Claim
23 words
A chartreusin derivative as an intermediate according to claim 40, wherein T 1 is tert-bytyldimethysilyl group, and T 2 is a hydrogen atom.
Claim 51
Dependent Claim
20 words
A chartreusin derivative as an intermediate according to claim 40, wherein both T 1 and T 2 are tertbutyldimethyl groups.
Claim 52
Dependent Claim
792 words
A 6-O-substituted chartreusin derivative of the formula (XII): ##STR176## wherein Q is ##STR177## wherein each of R and R' and R" is a C 1-11 alkanediyl group, a C 2-11 alkenediyl group, a C 2-11 alkynediyl group, a C 3-10 cycloalkanediyl group, a C 5-10 cycloalkenediyl group wherein each of the C 1-11 alkanediyl group, the C 2-11 akenediyl group, the C 2-11 alkynediyl group, the C 3-10 cycloalkanediyl group and the C 5-10 cycloalkenediyl group may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-6 alkoxy group, a C 1-6 alkythio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, an aminocarbonyl group, a hydroxycarbonyl group, a C 1-5 alkoxycarbonyl group, a phenyl group which may be substituted by a halogen atom or a hydroxy group or a mercapto group or a C 1-3 alkoxy group or a C 1-3 alkylthio group, or a 3-indolyl group which may be substituted by a halogen atom, or each or R, R' and R" is a phenyllene group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-6 akoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsufinyl group, or a C 1-5 akoxycarbonyl group; each of Z 1 , Z' 1 and Z" 1 is a hydrogen atom, or a C 1-6 alkyl group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-3 alkoxy group, or a C 1-3 alkylthio group; Z 2 is a hydrogen atom, a formyl group, a C 1-6 alkyl group, a C 1-6 alkylcarbonyl group, a benzoyl group wherein each of the C 1-6 alkyl group, the C 1-6 alkylcarbonyl group and the benzoyl group may be substituted by the same substitutent as substitutent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z" 1 , or Z 2 is a benzyloxycarbonyl group which may be substituted by a halogen atom; Z 1 and Z 2 , when taken togehter with the nitrogen atom, may form a nitrogen-containing C 2-10 heterocyclic group which may be substituted by the same substituent as substitutent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z" 1 , or Q is a C 1-11 alkyl group, a C 2-11 alkenyl group, a C 3-11 alkynyl group, a C 3-10 cycloalkyl group, a C 5-10 cycloalkenyl group, a C 1-10 alkylcarbonyl group, a C 1-10 akoxycarbonyl group, wherein each of the C 1-11 alkyl group, the C 2 -alkenyl group, the C 3-11 alkynyl group, the C 3-10 cycloalkyl group, the C 5-10 cycloalkenyl group, the C 1-10 alkylcarbonyl group and the C 1-10 alkxoycarbonyl group may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a notro group, a C 1-6 alkoxy group, a C 1-6 akylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, a C 1-6 phenyoxycarbonyl group, a C 1-6 alkylcarbonyloxy group, a C 3-7 cycloalkyl group, a phenyl group, a phenoxy group, a phenylthio group, a phenylsulfinyl group, a phenylsulfonyl group, a benzoyl group, a benzoyloxy group or a benzyloxy group wherein each of the C 1-6 alkoxy group, the C 1-6 alkylthio group, the C 1-6 akylsulfinyl group, the C 1-6 alkylsulfonyl group, the C 1-6 alkylcarbonyl group, the C 1-6 alkoxycarbonyl group, the phenoxycarbonyl group, the C 1-6 alkylcarbonyloxy group, the C 3-7 cycloalkyl group, the phenyl group, the phenoxy group, the phenylthio group, the phenylsulfinyl group, the phenylsulfonyl group, the benzoyl group, the benzoyloxy group, and benzyloxy group may be substituted by the same substituent as substituent for sadi C 1-6 alkyl group as each of Z 1 , Z 1 ', and Z 1 ", or Q is a phenyl group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a nitro group, a C 1-6 akylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alky group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylcarbonyl group, a C 1-6 akoxycarbonyl group, or a C 1-6 alkylcarbonyloxy group wherein each of the C 1-6 alkyl group, the C 1-6 alkoxy group, the C 1-6 akylthio group, the C 1-6 alkylcarbonyl group, the C 1-6 alkoxycarbonyl group, and the C 1-6 alkylcarbonyloxy group may be substituted by teh same substitutent as substituent for said C 1-6 alkyl group as each of Z 1 , Z 1 ', and Z 1 ", the total number of atoms of Q other than hydrogen atoms being 30 or less.
Claim 53
Dependent Claim
792 words
A 6-O-substituted chartreusin derivative of the formula (XII): ##STR176## wherein Q is ##STR177## wherein each of R and R' and R" is a C 1-11 alkanediyl group, a C 2-11 alkenediyl group, a C 2-11 alkynediyl group, a C 3-10 cycloalkanediyl group, a C 5-10 cycloalkenediyl group wherein each of the C 1-11 alkanediyl group, the C 2-11 akenediyl group, the C 2-11 alkynediyl group, the C 3-10 cycloalkanediyl group and the C 5-10 cycloalkenediyl group may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-6 alkoxy group, a C 1-6 alkythio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, an aminocarbonyl group, a hydroxycarbonyl group, a C 1-5 alkoxycarbonyl group, a phenyl group which may be substituted by a halogen atom or a hydroxy group or a mercapto group or a C 1-3 alkoxy group or a C 1-3 alkylthio group, or a 3-indolyl group which may be substituted by a halogen atom, or each or R, R' and R" is a phenyllene group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-6 akoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsufinyl group, or a C 1-5 akoxycarbonyl group; each of Z 1 , Z' 1 and Z" 1 is a hydrogen atom, or a C 1-6 alkyl group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a C 1-3 alkoxy group, or a C 1-3 alkylthio group; Z 2 is a hydrogen atom, a formyl group, a C 1-6 alkyl group, a C 1-6 alkylcarbonyl group, a benzoyl group wherein each of the C 1-6 alkyl group, the C 1-6 alkylcarbonyl group and the benzoyl group may be substituted by the same substitutent as substitutent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z" 1 , or Z 2 is a benzyloxycarbonyl group which may be substituted by a halogen atom; Z 1 and Z 2 , when taken togehter with the nitrogen atom, may form a nitrogen-containing C 2-10 heterocyclic group which may be substituted by the same substituent as substitutent for said C 1-6 alkyl group as each of Z 1 , Z' 1 and Z" 1 , or Q is a C 1-11 alkyl group, a C 2-11 alkenyl group, a C 3-11 alkynyl group, a C 3-10 cycloalkyl group, a C 5-10 cycloalkenyl group, a C 1-10 alkylcarbonyl group, a C 1-10 akoxycarbonyl group, wherein each of the C 1-11 alkyl group, the C 2 -alkenyl group, the C 3-11 alkynyl group, the C 3-10 cycloalkyl group, the C 5-10 cycloalkenyl group, the C 1-10 alkylcarbonyl group and the C 1-10 alkxoycarbonyl group may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a notro group, a C 1-6 alkoxy group, a C 1-6 akylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, a C 1-6 phenyoxycarbonyl group, a C 1-6 alkylcarbonyloxy group, a C 3-7 cycloalkyl group, a phenyl group, a phenoxy group, a phenylthio group, a phenylsulfinyl group, a phenylsulfonyl group, a benzoyl group, a benzoyloxy group or a benzyloxy group wherein each of the C 1-6 alkoxy group, the C 1-6 alkylthio group, the C 1-6 akylsulfinyl group, the C 1-6 alkylsulfonyl group, the C 1-6 alkylcarbonyl group, the C 1-6 alkoxycarbonyl group, the phenoxycarbonyl group, the C 1-6 alkylcarbonyloxy group, the C 3-7 cycloalkyl group, the phenyl group, the phenoxy group, the phenylthio group, the phenylsulfinyl group, the phenylsulfonyl group, the benzoyl group, the benzoyloxy group, and benzyloxy group may be substituted by the same substituent as substituent for sadi C 1-6 alkyl group as each of Z 1 , Z 1 ', and Z 1 ", or Q is a phenyl group which may be substituted by a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a nitro group, a C 1-6 akylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alky group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylcarbonyl group, a C 1-6 akoxycarbonyl group, or a C 1-6 alkylcarbonyloxy group wherein each of the C 1-6 alkyl group, the C 1-6 alkoxy group, the C 1-6 akylthio group, the C 1-6 alkylcarbonyl group, the C 1-6 alkoxycarbonyl group, and the C 1-6 alkylcarbonyloxy group may be substituted by teh same substitutent as substituent for said C 1-6 alkyl group as each of Z 1 , Z 1 ', and Z 1 ", the total number of atoms of Q other than hydrogen atoms being 30 or less.
Claim 54
Dependent Claim
39 words
A 6-O-substituted chartreusin derivative according to claim 49, wherein each of R, R' and R" in Q is said C 1-11 alkanediyl group and the total number of atoms of Q other than hydrogen atom is 15 or less.
Claim 55
Dependent Claim
38 words
A 6-0-substituted chartreusin derivative according to claim 49, wherein Q is said C 1-11 alkyl group or said C 3-10 cycloalkyl group; and the total number of atoms of Q other than hydrogen atom being 15 or less.
References Cited (Backward Citations)
US4521240A
Cited
US4518589A
Cited
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