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US4564616A
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Anti-cancer quinazoline derivatives
Assignee: BTG International Ltd
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Filing: 1984-03-20
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Granted: 1986-01-14
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Expires: 2004-03-20
Abstract
Abstract Quinazoline derivatives of formula: ##STR1## wherein R represents: (1) a straight or branched chain unsaturated hydrocarbon group, or (2) a straight or branched chain saturated or unsaturated hydrocarbon group which is substituted by at least one: heteroatom, the or each heteroatom being halogeno when R is a C 1 hydrocarbon group; or saturated carbocyclic group; or group containing at least one heteroatom, the or each heteroatom being O, N or S when R contains a cyclic group; and n is O or an integer of 1-4; X or, when n is an integer of at least 2, each X independently, represents a halogeno, C 1 -C 4 alkyl, aryl or aralkyl group or a group including at least one heteroatom; and Y represents a group of formula: ##STR2## wherein m≧1 (poly-L-glutamates); and the pharmaceutically acceptable salts and esters thereof, which are suitable as anti-cancer agents.
Inventors
- 👤 Terence R. Jones
- 👤 Kenneth R. Harrap
- 👤 Alan H. Calvert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 09:28
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/70; C07D239/72; C07D239/95; C07D205/00; C07D205/02; C07D205/04
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
133 words
A pharmaceutical composition useful for aiding regression and palliation of cancer, comprising an effective amount of an active compound in association with a pharmaceutically acceptable carrier or diluent wherein the active compound is a compound of formula: ##STR18## wherein R represents a straight or branched chain unsaturated C 2 -C 4 hydrocarbon group or a fluorine-substituted straight or branched chain hydrocarbon group having up to 4 carbon atoms; n is 0, 1 or 2; X, which is linked in a position ortho to the --CO--Y group, represents a halogeno or C 1 -C 4 alkyl group, and where two X's are present these may be the same or different; and Y represents a group of formula: ##STR19## wherein m is an integer of 1-9 (poly-L-glutamates); or a pharmaceutically acceptable salt or ester thereof.
Claim 2
Dependent Claim
133 words
A pharmaceutical composition useful for aiding regression and palliation of cancer, comprising an effective amount of an active compound in association with a pharmaceutically acceptable carrier or diluent wherein the active compound is a compound of formula: ##STR18## wherein R represents a straight or branched chain unsaturated C 2 -C 4 hydrocarbon group or a fluorine-substituted straight or branched chain hydrocarbon group having up to 4 carbon atoms; n is 0, 1 or 2; X, which is linked in a position ortho to the --CO--Y group, represents a halogeno or C 1 -C 4 alkyl group, and where two X's are present these may be the same or different; and Y represents a group of formula: ##STR19## wherein m is an integer of 1-9 (poly-L-glutamates); or a pharmaceutically acceptable salt or ester thereof.
Claim 3
Dependent Claim
12 words
A composition according to claim 1 wherein R is allyl or propargyl.
Claim 4
Dependent Claim
16 words
A composition according to claim 1 wherein n is 1 and X is chloro or methyl.
Claim 5
Dependent Claim
27 words
A composition according to claim 1 wherein Y is an L-glutamic acid residue, one or both of the acid groups optionally being in salt or ester form.
Claim 6
Dependent Claim
17 words
A composition according to claim 1 wherein the active compound is N-(4-(N-((2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamic acid, N-(2-methyl-4-(N-((2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamic acid, N-(2-chloro-4-(N-((2-amino-4-hydroxy-6-quinazolinyl)-methyl)prop-2-ynylamino)benzoyl)-L-glutamic acid.
Claim 7
Dependent Claim
21 words
A composition according to claim 1 wherein the active compound is in the form of a disodium salt or diethyl ester.
Claim 8
Dependent Claim
16 words
A compound according to claim 1 wherein R represents a 2-fluoroethyl group or a 2,2,2-trifluoromethyl group.
Claim 9
Dependent Claim
30 words
A method of aiding regression and palliation of cancer in a host which comprises administering to that host an effective amount of an active compound as defined in claim 1.
Claim 10
Dependent Claim
21 words
A method according to claim 8 wherein the active compound is as defined in any one of claims 3 to 7.
Claim 11
Dependent Claim
90 words
A compound of the formula ##STR20## wherein R 1 is a fluorine substituted straight or branched chain hydrocarbon group having up to 4 carbon atoms, n is 0, 1 or 2; X, which is linked in a position ortho to the --CO--Y group, represents a halogeno or C 1 -C 4 alkyl group, and where two X's are present these may be the same or different; and Y represents a group of formula: ##STR21## wherein m is an integer of 1-9 (poly-L-glutamates); or a pharmaceutically acceptable salt or ester thereof.
Claim 12
Dependent Claim
90 words
A compound of the formula ##STR20## wherein R 1 is a fluorine substituted straight or branched chain hydrocarbon group having up to 4 carbon atoms, n is 0, 1 or 2; X, which is linked in a position ortho to the --CO--Y group, represents a halogeno or C 1 -C 4 alkyl group, and where two X's are present these may be the same or different; and Y represents a group of formula: ##STR21## wherein m is an integer of 1-9 (poly-L-glutamates); or a pharmaceutically acceptable salt or ester thereof.
Claim 13
Dependent Claim
16 words
A compound according to claim 10 wherein n is 1 and X is chloro or methyl.
Claim 14
Dependent Claim
27 words
A compound according to claim 10 wherein Y is an L-glutamic acid residue, one or both of the acid groups optionally being in salt or ester form.
Claim 15
Dependent Claim
16 words
A compound according to claim 10 in the form of a disodium salt or diethyl ester.
Claim 16
Dependent Claim
17 words
A compound according to claim 10 wherein R 1 represents a 2-fluoroethyl group or a 2,2,2-trifluoroethyl group.
Claim 17
Dependent Claim
2 words
N-(4-(N-((2-amino-4-hydroxy-6-quinazolinyl)methyl)-2-fluoroethylamino)benzoyl)-L-glutamic acid.
Claim 18
Dependent Claim
2 words
N-(4-(N-((2-amino-4-hydroxy-6-quinazolinyl)methyl)-2-fluoroethylamino)benzoyl)-L-glutamic acid.
References Cited (Backward Citations)
US3472851A
Cited
US3471498A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-01-13 | 1989-07-15 | 1990-01-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-13 | 1993-07-15 | 1994-01-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-13 | 1997-07-15 | 1998-01-14 | $7700.00 | Window Closed / Lapsed |