Therapeutic methods and compositions involving isoflavones

Details Therapeutic methods and compositions involving isoflavones Therapeutic methods and compositions involving isoflavones

1999-08-05

2003-11-18

Criares, Theodore J. (Department: 1617)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

Reexamination Certificate

active

06649648

ABSTRACT:

This invention relates to therapeutic uses, methods, compounds, formulations, drinks and food stuffs involving, containing, comprising and/or including certain isoflavone compounds.
The isoflavone compounds according to this invention are described by general formula I,
in which
Z is H,
R
1
is H, or R
A
CO where R
A
is C
1-10
alkyl or an amino acid,
R
2
is H, OH, or OR
B
where R
B
is an amino acid or COR
A
where R
A
is as previously defined, W is H, A is H or OH, and B is selected from
W is H, and A and B taken together form a six membered ring selected from
W, A and B taken with the groups with which they are associated comprise
W and A taken together with the groups with which they are associated comprise
and B is
wherein
R
3
is H, COR
A
where R
A
is as previously defined, CO
2
R
C
where R
C
is C
1-10
alkyl, or COR
B
where R
B
is as previously defined,
R
4
is H, COR
D
where R
D
is H, OH, C
1-10
alkyl or an amino acid, CO
2
R
C
where R
C
is as previously defined, COR
E
where R
E
is H, C
1-10
alkyl or an amino acid, COOH, COR
C
where R
C
is as previously defined, or CONHR
E
where R
E
is as previously defined,
R
5
is H, CO
2
R
C
where R
C
is as previously defined, or COR
C
OR
E
where R
C
and R
E
are as previously defined, and where the two R
5
groups are attached to the same group they are the same or different,
R
6
is H or hydroxy C
1-10
alkyl,
X is preferably O, but may be N or S, and
Y is
where R
7
is H, or C
1-10
alkyl.
provided that compounds of the formula I where
R
1
, W and Z are H
R
2
is H or OH
A and B taken together are a six membered ring
Y is as defined above
and R
7
is H or OCH
3
,
are specifically excluded, and
provided that where the method is a method for the treatment or prophylaxis of menopausal syndrome or premenstrual tension syndrome compounds of the formula I where
R
1
is H, W and Z are H, and R
2
is H or OH,
A and B taken together are a six membered ring
or A is OH and B is
where Y is as defined above and R
7
is H are specifically excluded, and further provided that where the method is a method for the treatment of a form of cancer or rheumatoid arthritis compounds of the formula I where:
R
1
and W are H, Z is H or OCH
3
and R
2
is H or OH, and
A and B taken together are a six membered ring of the formula
Y is as defined above, R
4
is CO
2
H or CO
2
CH
2
CH
3
, and R
7
is H are specifically excluded.
Preferably the compounds of the formula I are selected from:
wherein
R
8
is COR where R
D
is as previously defined,
R
9
CO
2
R
C
or COR
E
where R
C
and R
E
are as previously defined,
R
10
is COR
C
or COR
C
OR
E
where R
C
and R
E
are as previously defined,
R
11
is H or OH,
R
12
is H, COOH, CO
2
R
C
where R
C
and is as previously defined, or CONHR
E
where R
E
is as previously defined,
R
13
is OH, OR
B
where R
B
is as previously defined, or COR
A
where R
A
is as previously defined,
R
14
is H, or COR
A
where R
A
is as previously defined,
R
15
is COR
A
where R
A
is as previously defined,
R
16
is H, COR
B
or CO
2
R
C
where R
B
and R
C
are as previously defined,
R
17
is H or hydroxy C
1-10
alkyl,
R
18
is H or C
1-10
alkyl,
and “
---
” represents either a single bond or a double bond.
Alkyl groups may be straight or branched chains. C
1-10
alkyl preferably contains from 1 to 5 carbons, more preferably methyl, ethyl or propyl.
Certain of the above compounds may be referred to by the names dihydrodaidzein (compound 1 where R
8
is H), dihydrogenestein (compounds 2 and 5), dehydro-O-desmethylangolensin (compound 11), tetrahydrodaidzein (compound 8), equol and dehydroequol (compound 10), O-desmethyl-angolensin (ODMA—compound 13), and 6-hydroxy-O-desmethylangolensin (6-hydroxy-ODMA—compound 14).
It has surprisingly been found by the inventors that compounds of the formula I, and more specifically compounds of the formulae 1 to 19 have particular utility and effectiveness in the treatment, prophylaxis, amelioration defence against, and/or prevention of menopausal syndrome including hot flushes, anxiety, and depression, mood swings, night sweats, headaches, and urinary incontinence; osteoporosis; premenstrual syndrome, including fluid retention, cyclical mastalgia, and dysmenorrhoea; Reynaud's Syndrome; Reynaud's Phenomenon; Buergers Disease; coronary artery spasm; migraine headaches; hypertension; benign prostatic hypertrophy; breast cancer; uterine cancer; ovarian cancer; testicular cancer; large bowel cancer; endometrial cancer; prostatic cancer uterine cancer; atherosclerosis; Alzheimers disease; inflammatory diseases including inflammatory bowel disease, ulcerative colitis, Crohns disease; rheumatic diseases including rheumatoid arthritis; acne; baldness including male pattern baldness (alopecia hereditaria); psoriasis and diseases associated with oxidant stress including cancer, myocardial infarction stroke, arthritis, sunlight induced skin damage or cataracts.
According to a first aspect of the present invention there is provided a method for the treatment, prophylaxis, amelioration, defence against, and/or prevention of menopausal syndrome including hot flushes, anxiety, and depression, mood swings, night sweats, headaches, and urinary incontinence; osteoporosis; premenstrual syndrome, including fluid retention, cyclical mastalgia, and dysmenorrhoea; Reynaud's Syndrome; Reynaud's Phenomenon; Buergers Disease; coronary artery spasm; migraine headaches; hypertension; benign prostatic hypertrophy; breast cancer; uterine cancer; ovarian cancer; testicular cancer; large bowel cancer; endometrial cancer; prostatic cancer; uterine cancer; atherosclerosis; Alzheimers disease; inflammatory diseases including inflammatory bowel disease, ulcerative colitis, Crohns disease; rheumatic diseases including rheumatoid arthritis; acne; baldness including male pattern baldness (alopecia hereditaria); psoriasis and diseases associated with oxidant stress including cancer, myocardial infarction stroke, arthritis, sunlight induced skin damage or cataracts which comprises administering to a subject a therapeutically effective amount of one or more compounds of the formula I:
where R
1
, R
2
, Z, W, A and B are as previously defined, either alone or in association with one or more pharmaceutically acceptable carriers and/or excipients.
Preferably, one or more compounds of the formulae 1 to 19 may be used in the treatment, prophylaxis, amelioration of menopausal syndrome including hot flushes, anxiety, and depression, mood swings, night sweats, headaches, and urinary incontinence; osteoporosis; premenstnial syndrome, including fluid retention, cyclical mastalgia, and dysmenorrhoea; Reynaud's Syndrome; Reynaud's Phenomenon; Buergers Disease; coronary artery spasm; migraine headaches; hypertension; benign prostatic hypertrophy; breast cancer; uterine cancer; ovarian cancer; testicular cancer; large bowel cancer; endometrial cancer; prostatic cancer; uterine cancer; atherosclerosis; Alzheimers disease; inflammatory diseases including inflammatory bowel disease, ulcerative colitis, Crohns disease; rheumatic diseases including rheumatoid arthritis; acne; baldness including male pattern baldness (alopecia hereditaria); psoriasis and diseases associated with oxidant stress including cancer, myocardial infarction stroke, arthritis, sunlight induced skin damage or cataracts (for convenience hereafter referred to as the “therapeutic indications”). Cancer, myocardial infarction, stroke, arthritis, sunlight induced skin damage and cataracts are generally regarded to be associated with oxidant stress. This invention includes the treatment of diseases associated with oxidant stress.
A second aspect of the present invention is the use of compounds of the formula I for the manufacture of a medicament for the treatment, amelioration, defence against, prophylaxis and/or prevention of one or more of the therapeutic indications. It is particularly preferred that one or more compounds of the formulae 1 to 19 are employed in the treatment, prophylaxis, amelioration, defence against

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