US5216024A
Expired / Lapsed
US
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Cell growth inhibitors and methods of treating cancer and cell proliferative diseases
Assignee: Baylor College of Medicine
•
Filing: 1988-07-15
•
Granted: 1993-06-01
•
Expires: 2008-07-15
Abstract
Abstract The present invention discloses new and useful compounds including methyl p-hydroxyphenyllactate, its analogues, chemical derivatives and chemically related compounds and their use as antitumor agents, as inhibitors of proliferative cell growth and as prophylactic agents to inhibit and prevent cancer and non-malignant cell growth.
Inventors
- 👤 Barry M. Markaverich
- 👤 James H. Clark
- 👤 Rebecca Gregory
- 👤 Mary Alejandro
- 👤 Brian S. Middleditch
- 👤 Gregory A. Johnson
- 👤 Rajender S. Varma
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 18:18
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/075; A61K31/085; A61K31/12; A61K31/185; A61K31/19; A61K31/21; A61K31/215; A61P; A61P13/00; A61P13/02; A61P15/00; A61P35/00; C; C07; C07C; C07C59/00; C07C59/40; C07C59/42; C07C59/48
Claims Analysis
Total Claims: 84
Claim 1
Independent Claim
105 words
A method of regulating cell growth and proliferation in normal and malignant cells, comprising the step of administering, to an individual in need of said treatment, a therapeutic dose of a compound selected from the group consisting of the formulae: ##STR10## wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 is selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 2
Independent Claim
105 words
A method of regulating cell growth and proliferation in normal and malignant cells, comprising the step of administering, to an individual in need of said treatment, a therapeutic dose of a compound selected from the group consisting of the formulae: ##STR10## wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 is selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 3
Dependent Claim
29 words
The method of claim 1, wherein said compound is selected from the group consisting of methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, n-propyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, n-butyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, 3-(4-hydroxyphenyl)-2-propenoic acid, 1-(4-hydroxyphenyl)-3-butanone, 1-(4-hydroxyphenyl)-3-pentanone, methyl-(4-hydroxyphenoxy)acetate, and methyl 3-(3,4-dihydroxyphenyl)-2-propenoate.
Claim 4
Independent Claim
107 words
A method of inhibiting the growth of proliferating cells which include a Type II nuclear estrogen binding site comprising the step of administering, to the proliferating cells, a biologically inhibiting dose of a compound selected from the group consisting of the formulae: ##STR11## wherein R 1 is selected from the group consisting of H, alkyl group containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 is selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 5
Independent Claim
107 words
A method of inhibiting the growth of proliferating cells which include a Type II nuclear estrogen binding site comprising the step of administering, to the proliferating cells, a biologically inhibiting dose of a compound selected from the group consisting of the formulae: ##STR11## wherein R 1 is selected from the group consisting of H, alkyl group containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 is selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 6
Dependent Claim
30 words
The method of claim 3, wherein said compound is selected from the group consisting of methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, n-propyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, n-butyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, 3-(4-hydroxyphenyl)-2-propenoic acid, 1-(4-hydroxyphenyl)-3-butanone, 1-(4-hydroxyphenyl)-3-pentanone, methyl (4-hydroxyphenoxy)acetate, and methyl 3-(3,4-dihydroxyphenyl)-2-propenoate.
Claim 7
Dependent Claim
27 words
The method of claim 3, wherein said proliferating cells are estrogen responsive tissue selected from the group consisting of uterus, mammary gland, uterine tumors and mammary tumors.
Claim 8
Dependent Claim
15 words
The method of claim 5, wherein said estrogen responsive tissue is human breast cancer cells.
Claim 9
Independent Claim
91 words
A method for treating benign prostatic hyperplasia, comprising the step of administering a therapeutic dose of a compound selected from the group consisting of the formulae: ##STR12## wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 is selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 10
Independent Claim
91 words
A method for treating benign prostatic hyperplasia, comprising the step of administering a therapeutic dose of a compound selected from the group consisting of the formulae: ##STR12## wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 is selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 11
Dependent Claim
31 words
The method of claim 7, wherein said compound is selected from the group consisting of methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, n-propyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, n-butyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, 3-(4-hydroxyphenyl)-2-propenoic acid, 1-(4-hydroxyphenyl)-3-butanone, 1-(4-hydroxyphenyl)-3-pentanone, methyl (4-hydroxyphenoxy)acetate, and methyl 3-(3,4-dihydroxyphenyl)-2-propenoate acid.
Claim 12
Dependent Claim
89 words
As an agent for regulating cell growth and proliferation in normal and malignant cells, a compound selected from the group consisting of the formulae: ##STR13## wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 is selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 13
Dependent Claim
89 words
As an agent for regulating cell growth and proliferation in normal and malignant cells, a compound selected from the group consisting of the formulae: ##STR13## wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 is selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 14
Dependent Claim
30 words
The agent of claim 9, wherein said compound is selected from the group consisting of methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, n-propyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, n-butyl 3-(4-hydroxyphenyl)-2-hydroxypropionate, 3-(4-hydroxyphenyl)-2-propenoic acid, 1-(4-hydroxyphenyl)-3-butanone, 1-(4-hydroxyphenyl)-3-pentanone, methyl-(4-hydroxyphenoxy)acetate, and methyl 3-(3,4-dihydroxyphenyl)-2-propenoate acid.
Claim 15
Independent Claim
79 words
A method for inhibiting the growth of proliferating cells comprising administration of a biologically inhibiting dose of a compound selected from the group consisting of: ##STR14## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons, and substituted or unsubstituted aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 16
Independent Claim
79 words
A method for inhibiting the growth of proliferating cells comprising administration of a biologically inhibiting dose of a compound selected from the group consisting of: ##STR14## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons, and substituted or unsubstituted aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 17
Dependent Claim
16 words
The method of claim 11 wherein said compound is selected from the group consisting of ##STR15##
Claim 18
Dependent Claim
29 words
The method of claim 11 wherein said compound is selected from the group consisting of 3-(4-Hydroxyphenyl)-1-phenyl-2-propen-1-one and 4-(4-Hydroxyphenyl)-3-buten-2-one, analogs, chemical derivatives and chemically related compounds to the proliferating cells.
Claim 19
Independent Claim
77 words
A method of treating benign prostatic hyperplasia, comprising the administration of a therapeutic dose of a compound selected from the group consisting of: ##STR16## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons, and substituted and unsubstituted aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 20
Independent Claim
77 words
A method of treating benign prostatic hyperplasia, comprising the administration of a therapeutic dose of a compound selected from the group consisting of: ##STR16## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons, and substituted and unsubstituted aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 21
Dependent Claim
16 words
The method of claim 14, wherein said compound is selected from the group consisting of ##STR17##
Claim 22
Dependent Claim
32 words
The method of claim 14, wherein said compound is selected from the group consisting of 3-(4-Hydroxyphenyl)-1-phenyl-2-propen-1-one and 4-(4-Hydroxyphenyl)-3-buten-2-one, and their analogs, chemical derivatives and chemically related compounds and pharmaceutically related salts thereof.
Claim 23
Dependent Claim
23 words
The method of claim 14, wherein said compound is selected from the group consisting of 3-(4-Hydroxyphenyl)-1-phenyl-2-propen-1-one and 4-(4-Hydroxyphenyl)-3-buten-2-one, and pharmaceutically related salts thereof.
Claim 24
Dependent Claim
60 words
The method of claim 1, wherein said compound is: ##STR18## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 25
Dependent Claim
60 words
The method of claim 1, wherein said compound is: ##STR19## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 26
Dependent Claim
60 words
The method of claim 1, wherein said compound is: ##STR20## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 27
Dependent Claim
60 words
The method of claim 1, wherein said compound is: ##STR21## and pharmaceutically acceptable salt thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 28
Dependent Claim
60 words
The method of claim 1, wherein said compound is: ##STR22## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 29
Dependent Claim
60 words
The method of claim 1, wherein said compound is: ##STR23## and pharmaceutically acceptable salt thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 30
Dependent Claim
60 words
The method of claim 1, wherein said compound is: ##STR24## and pharmaceutically acceptable salt thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 31
Dependent Claim
78 words
The method of claim 3 wherein said compound is: ##STR25## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 32
Dependent Claim
60 words
The method of claim 3 wherein said compound is: ##STR26## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 33
Dependent Claim
60 words
The method of claim 3 wherein said compound is: ##STR27## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 34
Dependent Claim
60 words
The method of claim 3 wherein said compound is: ##STR28## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 35
Dependent Claim
60 words
The method of claim 3 wherein said compound is: ##STR29## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 36
Dependent Claim
60 words
The method of claim 3 wherein said compound is: ##STR30## and pharmaceutically accetable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 37
Dependent Claim
60 words
The method of claim 3 wherein said compound is: ##STR31## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 38
Dependent Claim
60 words
The method of claim 3 wherein said compound is: ##STR32## and pharmaceutically acceptable salts thereof wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 39
Dependent Claim
11 words
The method of claim 2, wherein said compound is methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 40
Dependent Claim
11 words
The method of claim 2, wherein said compound is n-propyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 41
Dependent Claim
11 words
The method of claim 2, wherein said compound is n-butyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 42
Dependent Claim
11 words
The method of claim 2, wherein said compound is 3-(4-hydroxyphenyl)-2-propenoic acid.
Claim 43
Dependent Claim
10 words
The method of claim 2, wherein said compound is 1-(4-hydroxyphenyl)-3-butanone.
Claim 44
Dependent Claim
10 words
The method of claim 2, wherein said compound is 1-(4-hydroxyphenyl)-3-pentanone.
Claim 45
Dependent Claim
10 words
The method of claim 2, wherein said compound is methyl-(4-hydroxyphenoxy)acetate.
Claim 46
Dependent Claim
11 words
The method of claim 2, wherein said compound is methyl 3-(3,4-dihydroxyphenyl)-2-propenoate.
Claim 47
Dependent Claim
11 words
The method of claim 4, wherein said compound is methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 48
Dependent Claim
11 words
The method of claim 4, wherein said compound is n-propyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 49
Dependent Claim
11 words
The method of claim 4, wherein said compound is n-butyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 50
Dependent Claim
11 words
The method of claim 4, wherein said compound is 3-(4-hydroxyphenyl)-2-propenoic acid.
Claim 51
Dependent Claim
10 words
The method of claim 4, wherein said compound is 1-(4-hydroxyphenyl)-3-butanone.
Claim 52
Dependent Claim
10 words
The method of claim 4, wherein said compound is 1-(4-hydroxyphenyl)-3-pentanone.
Claim 53
Dependent Claim
10 words
The method of claim 4, wherein said compound is methyl-(4-hydroxyphenoxy)acetate.
Claim 54
Dependent Claim
11 words
The method of claim 4, wherein said compound is methyl 3-(3,4-dihydroxyphenyl)-2-propenoate.
Claim 55
Dependent Claim
78 words
The method of claim 7 wherein said compound is: ##STR33## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 ; and R 4 selected from the group consisting of H and an alkyl group of 1 to 6 carbons.
Claim 56
Dependent Claim
60 words
The method of claim 7 wherein said compound is: ##STR34## and pharmaceutically acceptable salts thereof wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 57
Dependent Claim
60 words
The method of claim 7 wherein said compound is: ##STR35## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 58
Dependent Claim
60 words
The method of claim 7 wherein said compound is: ##STR36## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 59
Dependent Claim
60 words
The method of claim 7 wherein said compound is: ##STR37## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 60
Dependent Claim
60 words
The method of claim 7 wherein said compound is: ##STR38## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group. consisting of H, OH and OCH 3 .
Claim 61
Dependent Claim
60 words
The method of claim 7 wherein said compound is: ##STR39## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 62
Dependent Claim
60 words
The method of claim 7 wherein said compound is: ##STR40## and pharmaceutically acceptable salts thereof, wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 63
Dependent Claim
11 words
The method of claim 7, wherein said compound is methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 64
Dependent Claim
11 words
The method of claim 7, wherein said compound is n-propyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 65
Dependent Claim
11 words
The method of claim 7, wherein said compound is n-butyl 3-(4-hydroxyphenyl)-2-hydroxypropionate.
Claim 66
Dependent Claim
11 words
The method of claim 7, wherein said compound is 3-(4-hydroxyphenyl)-2-propenoic acid.
Claim 67
Dependent Claim
10 words
The method of claim 7, wherein said compound is 1-(4-hydroxyphenyl)-3-butanone.
Claim 68
Dependent Claim
10 words
The method of claim 7, wherein said compound is 1-(4-hydroxyphenyl)-3-pentanone.
Claim 69
Dependent Claim
10 words
The method of claim 7, wherein said compound is methyl-(4-hydroxyphenoxy)acetate.
Claim 70
Dependent Claim
11 words
The method of claim 7, wherein said compound is methyl 3-(3,4-dihydroxyphenyl)-2-propenoate.
Claim 71
Dependent Claim
62 words
The method of claim 11 wherein said compound is: ##STR41## and pharmaceutically acceptable salts thereof wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and substituted or unsubstituted aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 72
Dependent Claim
62 words
The method of claim 11 wherein said compound is: ##STR42## and pharmaceutically acceptable salts thereof wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and substituted or unsubstituted aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 73
Dependent Claim
62 words
The method of claim 11 wherein said compound is: ##STR43## and pharmaceutically acceptable salts thereof wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and substituted or unsubstituted aryl groups; R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 74
Dependent Claim
15 words
The method of claim 11 wherein said compound is: ##STR44## and pharmaceutically acceptable salts thereof.
Claim 75
Dependent Claim
15 words
The method of claim 11 wherein said compound is: ##STR45## and pharmaceutically acceptable salts thereof.
Claim 76
Dependent Claim
15 words
The method of claim 11 wherein said compound is: ##STR46## and pharmaceutically acceptable salts thereof.
Claim 77
Dependent Claim
15 words
The method of claim 11 wherein said compound is: ##STR47## and pharmaceutically acceptable salts thereof.
Claim 78
Dependent Claim
63 words
The method of claim 14 wherein said compound is: ##STR48## and pharmaceutically acceptable salts thereof wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and substituted or unsubstituted aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 79
Dependent Claim
63 words
The method of claim 14 wherein said compound is: ##STR49## and pharmaceutically acceptable salts thereof wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and substituted or unsubstituted aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 80
Dependent Claim
63 words
The method of claim 14 wherein said compound is: ##STR50## and pharmaceutically acceptable salts thereof wherein, R 1 is selected from the group consisting of H, alkyl groups containing 1 to 6 carbons and substituted or unsubstituted aryl groups; and R 2 and R 3 are not both H and are selected from the group consisting of H, OH and OCH 3 .
Claim 81
Dependent Claim
15 words
The method of claim 14 wherein said compound is: ##STR51## and pharmaceutically acceptable salts thereof.
Claim 82
Dependent Claim
15 words
The method of claim 14 wherein said compound is: ##STR52## and pharmaceutically acceptable salts thereof.
Claim 83
Dependent Claim
15 words
The method of claim 14 wherein said compound is: ##STR53## and pharmaceutically acceptable salts thereof.
Claim 84
Dependent Claim
15 words
The method of claim 14 wherein said compound is: ##STR54## and pharmaceutically acceptable salts thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-05-31 | 1996-11-30 | 1997-06-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-05-31 | 2000-11-30 | 2001-06-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-05-31 | 2004-11-30 | 2005-06-01 | $7700.00 | Window Closed / Lapsed |