Patent US4600721A successfully refreshed from Google Patents.
US4600721A
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Pharmaceutical preparation
Assignee: LUDWIG HEUMANN and CO GmbH
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Filing: 1985-03-27
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Granted: 1986-07-15
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Expires: 2005-03-27
Abstract
Abstract Pharmaceutical preparations having an antiphlogistic action are described. The preparations contain, as active ingredient, a benzazole derivative corresponding to the general tautomeric formulae I ##STR1## wherein X represents a sulphur or oxygen atom and R 1 represents a hydrogen atom and R 2 a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group or R 1 and R 2 together represent the group ##STR2## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group, or they contain a physiologically acceptable salt thereof. These pharmaceutical preparations are suitable in particular for the treatment of inflammatory conditions and for inhibiting the lipoxygenase and/or cyclooxygenase route of arachidonic acid metabolism.
Inventors
- 👤 Peter Morsdorf
- 👤 Helmut Schickaneder
- 👤 Heidrun Engler
- 👤 Istvan Szelenyi
- 👤 Kurt H. Ahrens
- 👤 Kay Brune
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 09:45
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C07D263/54; C07D263/58; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/41; A61K31/42; A61K31/425; A61P; A61P11/00; A61P17/00; A61P27/00; A61P27/02; A61P27/14; A61P29/00; A61P37/00; A61P37/08; A61P43/00; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/82
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
94 words
A method of treating a phlogistic condition which comprises administering to a host in need thereof an antiphlogistic effective amount of a benzazole derivative of the formula ##STR20## wherein X represents a sulphur or oxygen atom and R 1 represents a hydrogen atom and R 2 a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group or R 1 and R 2 together represent the group ##STR21## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group, or a physiologically acceptable salt thereof.
Claim 2
Independent Claim
94 words
A method of treating a phlogistic condition which comprises administering to a host in need thereof an antiphlogistic effective amount of a benzazole derivative of the formula ##STR20## wherein X represents a sulphur or oxygen atom and R 1 represents a hydrogen atom and R 2 a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group or R 1 and R 2 together represent the group ##STR21## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group, or a physiologically acceptable salt thereof.
Claim 3
Dependent Claim
13 words
The method of claim 1 wherein said antiphlogistic effective amount is 0.05-100 mg/kg.
Claim 4
Dependent Claim
11 words
The method of claim 2 wherein said amount is 0.1-10 mg/kg.
Claim 5
Dependent Claim
10 words
The method of claim 1 wherein R 1 is hydrogen.
Claim 6
Dependent Claim
12 words
The method of claim 4 wherein R 2 is formyl or carbethoxy.
Claim 7
Dependent Claim
38 words
The method of claim 1 wherein R 1 and R 2 together represent the group ##STR22## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group.
Claim 8
Dependent Claim
19 words
The method of claim 6 wherein R 3 is hydrogen or methyl and R 4 is methyl or ethyl.
Claim 9
Dependent Claim
48 words
The method of claim 1 wherein said benzazole derivative is selected from the group consisting of N-(benzothiazol-2-yl)-acetaldehyde hydrazone, N-(benzothiazol-2-yl)-acetone hydrazone, N-(benzothiazol-2-yl)-propionaldehyde hydrazone, N-(benzothiazol-2-yl)-methyl ethyl ketone hydrazone, N-(benzoxazol-2-yl)-acetaldehyde hydrazone, N-(benzoxazol-2-yl)-acetone hydrazone, N-(benzoxazol-2-yl)-propionaldehyde hydrazone, benzothiazol-2-one-(β-formyl hydrazone), N 2 -(benzothiazol-2-yl)-hydrazine carboxylic acid ethyl ester and N 2 -(benzothiazol-2-yl)-hydrazinocarboxylic acid tert-butyl ester.
Claim 10
Independent Claim
100 words
A method of inhibiting the lypooxygenase and/or cyclooxygenase route of arachidonic acid metabolism which comprises administering to a host in need thereof an effective inhibitory amount of a benzazole derivative of the formula ##STR23## wherein X represents a sulphur or oxygen atom and R 1 represents a hydrogen atom and R 2 a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group or R 1 and R 2 together represent the group ##STR24## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group, or a physiologically acceptable salt thereof.
Claim 11
Independent Claim
100 words
A method of inhibiting the lypooxygenase and/or cyclooxygenase route of arachidonic acid metabolism which comprises administering to a host in need thereof an effective inhibitory amount of a benzazole derivative of the formula ##STR23## wherein X represents a sulphur or oxygen atom and R 1 represents a hydrogen atom and R 2 a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group or R 1 and R 2 together represent the group ##STR24## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group, or a physiologically acceptable salt thereof.
Claim 12
Dependent Claim
11 words
The method of claim 9 wherein said amount is 0.05-100 mg/kg.
Claim 13
Dependent Claim
11 words
The method of claim 9 wherein said amount is 0.1-10 mg/kg.
Claim 14
Dependent Claim
10 words
The method of claim 9 wherein R 1 is hydrogen.
Claim 15
Dependent Claim
12 words
The method of claim 9 wherein R 2 is formyl for carbethoxy.
Claim 16
Dependent Claim
38 words
The method of claim 9 wherein R 1 and R 2 together represent the group ##STR25## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group.
Claim 17
Dependent Claim
19 words
The method of claim 9 wherein R 3 is hydrogen or methyl and R 4 is methyl or ethyl.
Claim 18
Dependent Claim
48 words
The method of claim 9 wherein said benzazole derivative is selected from the group consisting of N-(benzothiazol-2-yl)-acetaldehyde hydrazone, N-(benzothiazol-2-yl)-acetone hydrazone, N-(benzothiazol-2-yl)-propionaldehyde hydrazone, N-(benzothiazol-2-yl)-methyl ethyl ketone hydrazone, N-(benzoxazol-2-yl)-acetaldehyde hydrazone, N-(benzoxazol-2-yl)-acetone hydrazone, N-(benzoxazol-2-yl)-propionaldehyde hydrazone, benzothiazol-2-one-(β-formyl hydrazone), N 2 -(benzothiazol-2-yl)-hydrazine carboxylic acid ethyl ester and N 2 -(benzothiazol-2-yl)-hydrazinocarboxylic acid tert-butyl ester.
Claim 19
Dependent Claim
87 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an antiphlogistic effective amount of a benzazole derivative of the formula ##STR26## wherein X represents a sulphur or oxygen atom and R 1 represents a hydrogen atom and R 2 a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group or R 1 and R 2 together represent the group ##STR27## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group, or a physiologically acceptable salt thereof.
Claim 20
Dependent Claim
87 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an antiphlogistic effective amount of a benzazole derivative of the formula ##STR26## wherein X represents a sulphur or oxygen atom and R 1 represents a hydrogen atom and R 2 a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group or R 1 and R 2 together represent the group ##STR27## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group, or a physiologically acceptable salt thereof.
Claim 21
Dependent Claim
9 words
The composition of claim 17 wherein X is sulphur.
Claim 22
Dependent Claim
9 words
The composition of claim 17 wherein X is sulphur.
Claim 23
Dependent Claim
23 words
The composition of claim 17 wherein R 1 is hydrogen and R 2 is a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group.
Claim 24
Dependent Claim
12 words
The composition of claim 17 wherein R 2 is formyl or carbethoxy.
Claim 25
Dependent Claim
38 words
The composition of claim 17 wherein R 1 and R 2 together represent the group ##STR28## wherein R 3 and R 4 denote, independently of one another, a hydrogen atom or a C 1 -C 6 -alkyl group.
Claim 26
Dependent Claim
19 words
The composition of claim 22 wherein R 3 is hydrogen or methyl and R 4 is methyl or ethyl.
Claim 27
Dependent Claim
48 words
The composition of claim 17 wherein said benzazole derivative is selected from the group consisting of N-(benzothiazol-2-yl)-acetaldehyde hydrazone, N-(benzothiazol-2-yl)-acetone hydrazone, N-(benzothiazol-2-yl)-propionaldehyde hydrazone, N-(benzothiazol-2-yl)-methyl ethyl ketone hydrazone, N-(benzoxazol-2-yl)-acetaldehyde hydrazone, N-(benzoxazol-2-yl)-acetone hydrazone, N-(benzoxazol-2-yl)-propionaldehyde hydrazone, benzothiazol-2-one-(β-formyl hydrazone), N 2 -(benzothiazol-2-yl)-hydrazine carboxylic acid ethyl ester and N 2 -(benzothiazol-2-yl)-hydrazinocarboxylic acid tert-butyl ester.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-07-14 | 1990-01-13 | 1990-07-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-07-14 | 1994-01-13 | 1994-07-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-07-14 | 1998-01-13 | 1998-07-15 | $7700.00 | Window Closed / Lapsed |