US5008294A
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Methods of treating tumors with compositions of catecholic butanes
Assignee: WESTERN ENGINEERING & RESEARCH Co
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Filing: 1987-06-03
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Granted: 1991-04-16
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Expires: 2007-06-03
Abstract
Abstract The invention relates to methods useful in the treatment of benign, premalignant and malignant solid tumors, especially those of the skin comprising methods for the administration of pharmacologically active compositions containing catecholic butanes. The invention also relates to methods of preventing the occurence of tumors, and the use of catecholic butanes as a sunscreening agent. The preferred catecholic butane is nordihydroguaiaretic acid. The preferred methods of application of the compositions containing catecholic butanes are by topical application and intratumor injection.
Inventors
- 👤 Edward S. Neiss
- 👤 Larry M. Allen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 05:11
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/21; A61K31/215; A61K31/22; A61K31/045; A61K31/05; A61K31/075; A61K31/085; A61K8/00; A61K8/18; A61K8/30; A61K8/33; A61K8/34; A61K8/347; A61P; A61P35/00; A61Q; A61Q17/00; A61Q17/04
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
114 words
A method for inhibiting the growth of a tumor which comprises topically administering to the situs of the tumor of a mammal in need of said treatment an effective amount of a composition comprising at least 1 catecholic butane of the formula: ##STR3## wherein R 1 and R 2 are independently H, lower alkyl, lower acyl, or alkylene; R 3 , and R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are independently H or lower alkyl; R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy, lower acyloxy, or any two adjacent groups together may be alkylene dioxy.
Claim 2
Independent Claim
114 words
A method for inhibiting the growth of a tumor which comprises topically administering to the situs of the tumor of a mammal in need of said treatment an effective amount of a composition comprising at least 1 catecholic butane of the formula: ##STR3## wherein R 1 and R 2 are independently H, lower alkyl, lower acyl, or alkylene; R 3 , and R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are independently H or lower alkyl; R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy, lower acyloxy, or any two adjacent groups together may be alkylene dioxy.
Claim 3
Dependent Claim
17 words
The method according to claim 1 wherein the composition contains 0.1-10 wt. % of said catecholic butane.
Claim 4
Dependent Claim
13 words
The method according to claim 1 wherein the catecholic butane is nordihydroguaiaretic acid.
Claim 5
Dependent Claim
19 words
The method according to claim 1 wherein said catecholic butane contains at least one lower alkyl ether derivative moiety.
Claim 6
Dependent Claim
19 words
The method according to claim 1 wherein said catecholic butane contains at least one lower acyl esther derivative moiety.
Claim 7
Dependent Claim
37 words
The method according to claim 1, wherein lower alkyl is C 1 -C 6 alkyl, R 3 and R 4 are C 1 -C 3 alkyl and the lower acyl is a C 1 -C 6 acyl.
Claim 8
Dependent Claim
39 words
The method according to claim 1, wherein the catecholic butane is selected from the group consisting of 1,4-bis(3,4-dihydroxphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dihydroxyphenyl)butane; 1,4-bis(3,4-dimethoxyphenyl)-2,3 -dimethylbutane; 1,4-bis(3,4-diethoxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dipropoxyphenyl)-2,3-dimethylbutane; 1-(3,4-dihydroxyphenyl)-4-(3,4,5-trihydroxyphenyl) butane; 1,4-bis(3,4-diacetoxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dipropionyloxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dibutyroyloxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-divaleroyloxphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dipivaloyloxphenyl)-2,3-dimethylbutane; 1,4-bis (3,4-dipivaloyloxyphenyl) butane; 1,4-bis(3,4-dineopentylcarboxylphenyl)-2,3-dimethylbutane; and 1-(3,4-dihydroxyphenyl)-4-phenylbutane; 1-(3,4-dihydroxyphenyl)-4-(2,5 dihydroxyphenyl) butane.
Claim 9
Dependent Claim
14 words
The method according to claim 1 wherein the composition includes a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
46 words
The method according to claim 1 wherein said administering is effectuated by means selected from the group consisting of administration to the surface of the skin at the situs of the tumor and injection of the composition into the interior or near vicinity of the tumor.
Claim 11
Dependent Claim
41 words
The method according to claim 1 wherein the tumor are selected from the group consisting of equine sarcoid, equine papilloma, equine malignant melanoma, equine squamous cell carcinoma, canine perianal adenoma, canine mast cell carcinoma, canine breast adenocarcinoma and canine malignant melanoma.
Claim 12
Dependent Claim
13 words
The method according to claim 10, wherein the catecholic butane is nordihydroguaiaretic acid.
Claim 13
Dependent Claim
19 words
The method according to claim 11, wherein 10 nanomoles of composition are applied to each milliliter of solid tumor.
Claim 14
Dependent Claim
47 words
The method according to claim 10 wherein said administering is effectuated by means selected from the group consisting of topical administration to the surface of the skin at the situs of the tumor and injection of the composition into the interior or near vicinity of the tumor.
Claim 15
Dependent Claim
14 words
The method according to claim 10 wherein said catecholic butane is substantially nordihydroguaiaretic acid.
Claim 16
Dependent Claim
32 words
The method according to claim 1 wherein the tumor is selected from the group consisting of malignant melanoma, mammary tumor, basal cell carcinoma, squamous cell carcinoma, and epidermal tumors of the skin.
Claim 17
Independent Claim
107 words
A method for treating tumors of the skin, which comprises administering to the skin of a mammal in need of said treatment an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR4## wherein R 1 and R 2 are independently H, lower alkyl, lower acyl or alkylene; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are independently H or lower alkyl; R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy, lower acyloxy, or any two adjacent groups may be alkylene dioxy.
Claim 18
Independent Claim
107 words
A method for treating tumors of the skin, which comprises administering to the skin of a mammal in need of said treatment an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR4## wherein R 1 and R 2 are independently H, lower alkyl, lower acyl or alkylene; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are independently H or lower alkyl; R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy, lower acyloxy, or any two adjacent groups may be alkylene dioxy.
Claim 19
Dependent Claim
14 words
The method according to claim 16 wherein the composition includes a pharmaceutically acceptable carrier.
Claim 20
Independent Claim
106 words
The method for treating a keratosis of the skin which comprises administering to the skin of a mammal in need of said treatment at the situs of the keratosis an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR5## wherein R 1 and R 2 are independently H, lower alkyl or lower acyl; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are independently H or lower alkyl; and R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy or lower acyloxy.
Claim 21
Independent Claim
106 words
The method for treating a keratosis of the skin which comprises administering to the skin of a mammal in need of said treatment at the situs of the keratosis an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR5## wherein R 1 and R 2 are independently H, lower alkyl or lower acyl; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are independently H or lower alkyl; and R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy or lower acyloxy.
Claim 22
Dependent Claim
36 words
The method according to claim 18 wherein the catecholic butane is selected from the group consisting of nordihydroguaiaretic acid in any of its racemic forms, nordihydroguaiaretic acid tetrapivalate, nordihydroguaiaretic acid tetrapropionate and all optical configurations thereof.
Claim 23
Dependent Claim
13 words
The method according to claim 19 wherein the catecholic butane is nordihydroguaiaretic acid.
Claim 24
Dependent Claim
17 words
The method according to claim 18 wherein the composition contains 0.1-10 wt. % of said catecholic butane.
Claim 25
Dependent Claim
19 words
The method according to claim 18 wherein said catecholic butane contains at least one lower alkyl ether derivative moiety.
Claim 26
Dependent Claim
19 words
The method according to claim 18 wherein said catecholic butane contains at least one lower acyl ester derivative moiety.
Claim 27
Dependent Claim
37 words
The method according to claim 18, wherein lower alkyl is C 1 -C 6 alkyl, R 3 and R 4 are C 1 -C 3 alkyl and the lower acyl is a C 1 -C 6 acyl.
Claim 28
Dependent Claim
39 words
The method according to claim 18, wherein the catecholic butane is selected from the group consisting of 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dihydroxyphenyl)butane; 1,4-bis(3,4-dimethoxyphenyl)-2,3 -dimethylbutane; 1,4-bis(3,4-diethoxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dipropoxyphenyl)-2,3-dimethylbutane; 1-(3,4-dihydroxyphenyl)-4-(3,4,5-trihydroxyphenyl) butane; 1,4-bis(3,4-diacetoxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dipropionyloxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dibutyroyloxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-divaleroyloxyphenyl)-2,3-dimethylbutane; 1,4-bis(3,4-dipivaloyloxphenyl)-2,3-dimethylbutane; 1,4-bis (3,4-dipivaloyloxyphenyl) butane; 1,4-bis(3,4-dineopentylcarboxylphenyl)-2,3-dimethylbutane; and 1-(3,4-dihydroxyphenyl)-4-phenylbutane; 1-(3,4-dihydroxyphenyl)-4-(2,5 dihydroxyphenyl) butane.
Claim 29
Dependent Claim
14 words
The method according to claim 18 wherein the composition includes a pharmaceutically acceptable carrier.
Claim 30
Dependent Claim
12 words
The method according to claim 18 wherein the keratosis is actinic keratosis.
Claim 31
Independent Claim
122 words
A method for treating actinic keratosis which comprises administering to the skin of a mammal in need of said treatment at the situs of the actinic keratosis an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR6## wherein R 1 and R 2 are independently H, lower alkyl, or lower acyl and R 1 and R 2 together may be alkylene; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are independently H or lower alkyl; and R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy, lower acyloxy, or any two adjacent groups may be aklylene dioxy.
Claim 32
Independent Claim
122 words
A method for treating actinic keratosis which comprises administering to the skin of a mammal in need of said treatment at the situs of the actinic keratosis an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR6## wherein R 1 and R 2 are independently H, lower alkyl, or lower acyl and R 1 and R 2 together may be alkylene; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are independently H or lower alkyl; and R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy, lower acyloxy, or any two adjacent groups may be aklylene dioxy.
Claim 33
Dependent Claim
36 words
The method according got claim 28 wherein the catecholic butane is selected from the group consisting of nordihydroguaiaretic acid in any of its racemic forms, nordihydroguaiaretic acid tetrapivalate, nordihydroguaiaretic acid tetrapropionate and all optical configurations thereof.
Claim 34
Independent Claim
36 words
A method for treating actinic keratosis which comprises administering to the skin of a mammal in need of said treatment at the situs of the actinic keratosis an effective amount of a composition comprising nordihydroguaiaretic acid.
Claim 35
Independent Claim
36 words
A method for treating actinic keratosis which comprises administering to the skin of a mammal in need of said treatment at the situs of the actinic keratosis an effective amount of a composition comprising nordihydroguaiaretic acid.
Claim 36
Independent Claim
119 words
A method for treating tumors of the skin which comprises administering to the skin of a mammal in need of said treatment an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR7## wherein R 1 is H, lower alkyl or lower acyl, R 2 is lower acyl and R 1 and R 2 together may be alkylene; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 R 13 are independently H or lower alkyl; and R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy or lower acyloxy; or any two adjacent groups together may be alkylene dioxy.
Claim 37
Independent Claim
119 words
A method for treating tumors of the skin which comprises administering to the skin of a mammal in need of said treatment an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR7## wherein R 1 is H, lower alkyl or lower acyl, R 2 is lower acyl and R 1 and R 2 together may be alkylene; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 R 13 are independently H or lower alkyl; and R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy or lower acyloxy; or any two adjacent groups together may be alkylene dioxy.
Claim 38
Independent Claim
115 words
A method for treating tumors of the skin which comprises administering to the skin of a mammal in need of said treatment an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR8## wherein R 1 and R 2 are independently H, lower alkyl or lower acyl and R 1 and R 2 together may be alkylene; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are H; and R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy or lower acyloxy; or any two adjacent groups together may be alkylene dioxy.
Claim 39
Independent Claim
115 words
A method for treating tumors of the skin which comprises administering to the skin of a mammal in need of said treatment an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR8## wherein R 1 and R 2 are independently H, lower alkyl or lower acyl and R 1 and R 2 together may be alkylene; R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 and R 13 are H; and R 7 , R 8 and R 9 are independently H, hydroxy, lower alkoxy or lower acyloxy; or any two adjacent groups together may be alkylene dioxy.
Claim 40
Independent Claim
83 words
A method for treating tumors of the skin which comprises administering to the skin of a mammal in need of said treatment an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR9## wherein R 1 , R 2 , R 7 and R 8 are lower acyl; R 3 and R 4 are methyl; and R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are H.
Claim 41
Independent Claim
83 words
A method for treating tumors of the skin which comprises administering to the skin of a mammal in need of said treatment an effective amount of a composition comprising at least one catecholic butane of the formula: ##STR9## wherein R 1 , R 2 , R 7 and R 8 are lower acyl; R 3 and R 4 are methyl; and R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are H.
Claim 42
Dependent Claim
18 words
The method for treating tumors of the skin according to claim 33 wherein the tumor is actinic keratosis.
References Cited (Backward Citations)
US3934034A
Cited
US4695590A
Cited
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