US4665075A
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Derivatives of hydroxy- or amino-substituted (piperidinylalkyl)quinazolines
Assignee: Janssen Pharmaceutica NV
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Filing: 1985-09-26
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Granted: 1987-05-12
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Expires: 2005-09-26
Abstract
Abstract Novel derivatives of hydroxy- or amino-substituted (piperidinylalkyl)quinazolines which are useful agents in the treatment of warmblooded animals suffering from diseases according to the vascular bed in which excessive serotonin release occurs.
Inventors
- 👤 Jan Vandenberk
- 👤 Ludo E. J. Kennis
- 👤 Josephus C. Mertens
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 19:42
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/06; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/30; C07D211/32; C07D239/00; C07D239/70; C07D239/72; C07D239/95; C07D239/96; C07D401/14; C07D405/00; C07D405/02; C07D405/04; C07D405/14
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
156 words
A chemical compound having the formula ##STR11## and a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen or C 1-6 alkyl; R 1 is hydroxy, C 1-10 alkylcarbonyloxy, amino, mono- and di(C 1-6 alkyl)amino, C 1-10 alkyl carbonylamino, phenylmethoxy or an azido group; R 2 is hydrogen or halo; Y 1 and Y 2 are each independently O or S; Alk is a C 1 -C 6 alkanediyl radical; and Q is 1 H-indol-3-yl or a radical of formula --X--Ar (a) wherein X is a bivalent radical selected from the group consisting of, >C═O; >CHOH; >CH--O--C(═O)--R a ; >CH 2 ; >C(O--C 1-6 alkyl) 2 ; ##STR12## >C═NOH and >C═N--NH 2 , said R a being hydrogen or C 1-6 alkyl and said q being the integer 2 or 3; wherein Ar is phenyl optionally substituted with up to three halo-, C 1-6 alkyl-, C 1-6 alkyloxy-, trifluoromethyl or amino groups, thienyl or pyridinyl.
Claim 2
Dependent Claim
156 words
A chemical compound having the formula ##STR11## and a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen or C 1-6 alkyl; R 1 is hydroxy, C 1-10 alkylcarbonyloxy, amino, mono- and di(C 1-6 alkyl)amino, C 1-10 alkyl carbonylamino, phenylmethoxy or an azido group; R 2 is hydrogen or halo; Y 1 and Y 2 are each independently O or S; Alk is a C 1 -C 6 alkanediyl radical; and Q is 1 H-indol-3-yl or a radical of formula --X--Ar (a) wherein X is a bivalent radical selected from the group consisting of, >C═O; >CHOH; >CH--O--C(═O)--R a ; >CH 2 ; >C(O--C 1-6 alkyl) 2 ; ##STR12## >C═NOH and >C═N--NH 2 , said R a being hydrogen or C 1-6 alkyl and said q being the integer 2 or 3; wherein Ar is phenyl optionally substituted with up to three halo-, C 1-6 alkyl-, C 1-6 alkyloxy-, trifluoromethyl or amino groups, thienyl or pyridinyl.
Claim 3
Dependent Claim
27 words
A chemical compound according to claim 1 wherein R 1 is hydrogen, amino, acetylamino or azido, R 2 and R are both hydrogen and Q is --CO--Ar.
Claim 4
Dependent Claim
11 words
A chemical compound according to claim 2 wherein Ar is halophenyl.
Claim 5
Dependent Claim
12 words
A chemical compound according to claim 1 wherein the compound is 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-6-hydroxy-2,4(1H,3H)-quinazolinedione.
Claim 6
Dependent Claim
12 words
A chemical compound according to claim 1 wherein the compound is 7-amino-3-[4-(4-fluorophenyl)-1-piperidinyl]butyl-2,4(1H,3H)-quinazolinedione.
Claim 7
Dependent Claim
12 words
A chemical compound according to claim 1 wherein the compound is 7-azido-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4-(1,3H)-quinazolinedione.
Claim 8
Dependent Claim
171 words
A serotonin-antagonistic composition comprising an inert carrier and as an active ingredient an effective serotonin-antagonistic amount of a chemical compound having the formula ##STR13## or a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen or C 1-6 alkyl; R 1 is hydroxy, C 1-10 alkylcarbonyloxy, amino, mono- and di-(C 1-6 alkyl)amino, C 1-10 alkylcarbonylamino, phenylmethoxy or an azido group; R 2 is hydrogen or halo; Y 1 and Y 2 are each independently O or S; Alk is a C 1 -C 6 alkanediyl radical; and Q is 1 H-indol-3-yl or a radical of formula --X--Ar (a) wherein X is a bivalent radical selected from the group consisting of, >C═O; >CHOH; >CH--O--C(═O)--R a ; >CH 2 ; >C(O--C 1-6 alkyl) 2; ##STR14## >C═NOH and >C═N--NH 2 , said R a being hydrogen or C 1-6 alkyl and said q being the integer 2 or 3; wherein Ar is phenyl optionally substituted with up to three halo-, C 1-6 alkyl-, C 1-6 alkyloxy-, trifluoromethyl or amino groups, thienyl or pyridinyl.
Claim 9
Dependent Claim
171 words
A serotonin-antagonistic composition comprising an inert carrier and as an active ingredient an effective serotonin-antagonistic amount of a chemical compound having the formula ##STR13## or a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen or C 1-6 alkyl; R 1 is hydroxy, C 1-10 alkylcarbonyloxy, amino, mono- and di-(C 1-6 alkyl)amino, C 1-10 alkylcarbonylamino, phenylmethoxy or an azido group; R 2 is hydrogen or halo; Y 1 and Y 2 are each independently O or S; Alk is a C 1 -C 6 alkanediyl radical; and Q is 1 H-indol-3-yl or a radical of formula --X--Ar (a) wherein X is a bivalent radical selected from the group consisting of, >C═O; >CHOH; >CH--O--C(═O)--R a ; >CH 2 ; >C(O--C 1-6 alkyl) 2; ##STR14## >C═NOH and >C═N--NH 2 , said R a being hydrogen or C 1-6 alkyl and said q being the integer 2 or 3; wherein Ar is phenyl optionally substituted with up to three halo-, C 1-6 alkyl-, C 1-6 alkyloxy-, trifluoromethyl or amino groups, thienyl or pyridinyl.
Claim 10
Dependent Claim
27 words
A serotonin-antagonistic composition according to claim 7 wherein R 1 is hydroxy, amino, acetylamino, or azido, R 2 and R are both hydrogen and Q is --CO--Ar.
Claim 11
Dependent Claim
11 words
A serotonin-antagonistic composition according to claim 8 wherein Ar is halophenyl.
Claim 12
Dependent Claim
12 words
A serotonin-antagonistic composition according to claim 7 wherein the compound is 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]-ethyl]-6-hydroxy-2,4(1H,3H)-quinazolinedione.
Claim 13
Dependent Claim
12 words
A serotonin-antagonistic composition according to claim 7 wherein the compound is 7-amino-3-[4-(4-fluorobenzoyl)-1-piperidinyl]butyl-2,4(1H,3H)-quinazolinedione.
Claim 14
Dependent Claim
12 words
A serotonin-antagonistic composition according to claim 7 wherein the compound is 7-azido-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4-(1,3H)-quinazolinedione.
Claim 15
Independent Claim
186 words
A method of treating warm-blooded animals suffering from diseases according to the vascular bed in which excessive serotonin release occurs which comprises the administration thereto of an effective serotonin-antagonistic amount of a chemical compound having the formula ##STR15## or a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen or C 1-6 alkyl; R 1 is hydroxy, C 1-10 alkylcarbonyloxy, amino, mono- and di-(C 1-6 alkyl)amino, C 1-10 alkylcarbonylamino, phenylmethoxy or an azido group; R 2 is hydrogen or halo; Y 1 and Y 2 are each independently O or S; Alk is a C 1 -C 6 alkanediyl radical; and Q is 1 H-indol-3-yl or a radical of formula --X--Ar (a) wherein X is a bivalent radical selected from the group consisting of, >C═O; >CHOH; >CH--O--C(═O)--R a ; >CH 2 ; >C(O--C 1-6 alkyl) 2 ; ##STR16## >C═NOH and >C═N--NH 2 , said R a being hydrogen or C 1-6 alkyl and said q being the integer 2 or 3; wherein Ar is phenyl optionally substituted with up to three halo-, C 1-6 alkyl-, C 1-6 alkyloxy-, trifluoromethyl or amino groups, thienyl or pyridinyl.
Claim 16
Independent Claim
186 words
A method of treating warm-blooded animals suffering from diseases according to the vascular bed in which excessive serotonin release occurs which comprises the administration thereto of an effective serotonin-antagonistic amount of a chemical compound having the formula ##STR15## or a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen or C 1-6 alkyl; R 1 is hydroxy, C 1-10 alkylcarbonyloxy, amino, mono- and di-(C 1-6 alkyl)amino, C 1-10 alkylcarbonylamino, phenylmethoxy or an azido group; R 2 is hydrogen or halo; Y 1 and Y 2 are each independently O or S; Alk is a C 1 -C 6 alkanediyl radical; and Q is 1 H-indol-3-yl or a radical of formula --X--Ar (a) wherein X is a bivalent radical selected from the group consisting of, >C═O; >CHOH; >CH--O--C(═O)--R a ; >CH 2 ; >C(O--C 1-6 alkyl) 2 ; ##STR16## >C═NOH and >C═N--NH 2 , said R a being hydrogen or C 1-6 alkyl and said q being the integer 2 or 3; wherein Ar is phenyl optionally substituted with up to three halo-, C 1-6 alkyl-, C 1-6 alkyloxy-, trifluoromethyl or amino groups, thienyl or pyridinyl.
Claim 17
Dependent Claim
26 words
A method according to claim 13 wherein R 1 is hydroxy, amino, acetylamino or azido, R 2 and R are both hydrogen and Q is --CO--Ar.
Claim 18
Dependent Claim
10 words
A method according to claim 14 wherein Ar is halophenyl.
Claim 19
Dependent Claim
15 words
A method of treating warm-blooded animals according to claim 13 wherein the compound is 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-6-hydroxy-2,4(1H,3H)-quinazolinedione.
Claim 20
Dependent Claim
15 words
A method of treating warm-blooded animals according to claim 13 wherein the compound is 7-amino-3-[4-(4-fluorobenzoyl)-1-piperidinyl]butyl-2,4(1H3,H)-quinazolinedione.
Claim 21
Dependent Claim
15 words
A method of treating warm-blooded animals according to claim 13 wherein the compound is 7-azido-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4-(1,3H)-quinazolinedione.
References Cited (Backward Citations)
US4335127A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-05-11 | 1990-11-10 | 1991-05-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-11 | 1994-11-10 | 1995-05-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-11 | 1998-11-10 | 1999-05-12 | $7700.00 | Window Closed / Lapsed |