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US4443451A
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Bicyclic pyrimidin-5-one derivatives
Assignee: Janssen Pharmaceutica NV
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Filing: 1982-04-21
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Granted: 1984-04-17
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Expires: 2002-04-21
Abstract
Abstract Novel 5H-thiazolo- and 5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one and 3,4-dihydro-2H,6H-pyrimido[2,1-b] [1,3]-thiazin-6-one derivatives, which compounds are useful psychotropic agents.
Inventors
- 👤 Ludo E. J. Kennis
- 👤 Josephus C. Mertens
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 15:41
CPC Classifications
C; C07; C07D; C07D513/00; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/56; A; A61; A61P; A61P25/00; A61P25/18; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/30; C07D211/32; C07D401/00; C07D401/02; C07D401/04; C07D513/02; C07D513/04
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
216 words
A chemical compound having the formula ##STR40## the pharmaceutically acceptable acid-addition salts and the stereochemically isomeric forms thereof, wherein: R 1 is hydrogen, lower alkyl or Ar; R 2 is hydrogen, lower alkyl or Ar; R 3 is hydrogen or lower alkyl; Alk is a lower alkanediyl radical; A is a bivalent radical having the formula ##STR41## having the carbon atom attached to the S-atom, wherein R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and lower alkyl and wherein R 4 and R 5 may also complete a saturated or unsaturated 5- or 6-membered carbocyclic ring, optionally substituted with a lower alkyl radical; and Q is a member selected from the group consisting of a radical having the formula --X--Ar (a) wherein X is a member selected from the group consisting of ##STR42## said R 7 being hydrogen or lower alkyl and said q being the integer 2 or 3; and a radical having the formula ##STR43## wherein R 8 is hydrogen or loweer alkyl and R 9 , R 10 and R 11 are each independently selected from the group consisting of hydrogen and halo; wherein Ar is phenyl or substituted phenyl, said substituted phenyl bearing an amino group and/or 1,2 or 3 halo atoms.
Claim 2
Dependent Claim
216 words
A chemical compound having the formula ##STR40## the pharmaceutically acceptable acid-addition salts and the stereochemically isomeric forms thereof, wherein: R 1 is hydrogen, lower alkyl or Ar; R 2 is hydrogen, lower alkyl or Ar; R 3 is hydrogen or lower alkyl; Alk is a lower alkanediyl radical; A is a bivalent radical having the formula ##STR41## having the carbon atom attached to the S-atom, wherein R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and lower alkyl and wherein R 4 and R 5 may also complete a saturated or unsaturated 5- or 6-membered carbocyclic ring, optionally substituted with a lower alkyl radical; and Q is a member selected from the group consisting of a radical having the formula --X--Ar (a) wherein X is a member selected from the group consisting of ##STR42## said R 7 being hydrogen or lower alkyl and said q being the integer 2 or 3; and a radical having the formula ##STR43## wherein R 8 is hydrogen or loweer alkyl and R 9 , R 10 and R 11 are each independently selected from the group consisting of hydrogen and halo; wherein Ar is phenyl or substituted phenyl, said substituted phenyl bearing an amino group and/or 1,2 or 3 halo atoms.
Claim 3
Dependent Claim
13 words
A chemical compound according to claim 1 wherein R 1 is lower alkyl.
Claim 4
Dependent Claim
58 words
A chemical compound according to claim 1 wherein R 1 is lower alkyl, Q is a radical of formula (a) wherein X is >C═O or a radical of formula (b) wherein R 9 , R 10 and R 11 are hydrogen, Ar is other than aminophenyl, R 2 is hydrogen or lower alkyl and R 3 is hydrogen.
Claim 5
Dependent Claim
17 words
A chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 6
Dependent Claim
17 words
A chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 7
Dependent Claim
17 words
A chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 8
Dependent Claim
17 words
A chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 9
Dependent Claim
17 words
A chemical compound selected from the group consisting of 6-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 10
Dependent Claim
17 words
A chemical compound selected from the group consisting of 6-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 11
Dependent Claim
247 words
A pharmaceutical composition for treating psychotropic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound selected from the group consisting of a bicyclic pyrimidin-5-one derivative having the formula ##STR44## the pharmaceutically acceptable acid-addition salts and the stereochemically isomeric forms thereof, wherein: R 1 is hydrogen, lower alkyl or Ar; R 2 is hydrogen, lower alkyl or Ar; R 3 is hydrogen or lower alkyl; Alk is a lower alkanediyl radical; A is a bivalent radical having the formula ##STR45## having the carbon atom attached to the S-atom, wherein R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and lower alkyl and wherein R 4 and R 5 may also complete a saturated or unsaturated 5- or 6-membered carbocyclic ring, optionally substituted with a lower alkyl radical; and Q is a member selected from the group consisting of a radical having the formula --X--Ar (a) wherein X is a member selected from the group consisting of ##STR46## said R 7 being hydrogen or lower alkyl and said q being the integer 2 or 3; and a radical having the formula ##STR47## wherein R 8 is hydrogen or lower alkyl and R 9 , R 10 and R 11 are each independently selected from the group consisting of hydrogen and halo; wherein Ar is phenyl or substituted phenyl, said substituted phenyl bearing an amino group and/or 1,2 or 3 halo atoms.
Claim 12
Dependent Claim
247 words
A pharmaceutical composition for treating psychotropic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound selected from the group consisting of a bicyclic pyrimidin-5-one derivative having the formula ##STR44## the pharmaceutically acceptable acid-addition salts and the stereochemically isomeric forms thereof, wherein: R 1 is hydrogen, lower alkyl or Ar; R 2 is hydrogen, lower alkyl or Ar; R 3 is hydrogen or lower alkyl; Alk is a lower alkanediyl radical; A is a bivalent radical having the formula ##STR45## having the carbon atom attached to the S-atom, wherein R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and lower alkyl and wherein R 4 and R 5 may also complete a saturated or unsaturated 5- or 6-membered carbocyclic ring, optionally substituted with a lower alkyl radical; and Q is a member selected from the group consisting of a radical having the formula --X--Ar (a) wherein X is a member selected from the group consisting of ##STR46## said R 7 being hydrogen or lower alkyl and said q being the integer 2 or 3; and a radical having the formula ##STR47## wherein R 8 is hydrogen or lower alkyl and R 9 , R 10 and R 11 are each independently selected from the group consisting of hydrogen and halo; wherein Ar is phenyl or substituted phenyl, said substituted phenyl bearing an amino group and/or 1,2 or 3 halo atoms.
Claim 13
Dependent Claim
13 words
A pharmaceutical composition according to claim 7 wherein R 1 is lower alkyl.
Claim 14
Dependent Claim
58 words
A pharmaceutical composition according to claim 7 wherein R 1 is lower alkyl, Q is a radical of formula (a) wherein X is >C═O or a radical of formula (b) wherein R 9 , R 10 and R 11 are hydrogen, Ar is other than aminophenyl, R 2 is hydrogen or lower alkyl and R 3 is hydrogen.
Claim 15
Dependent Claim
38 words
A pharmaceutical composition for treating psychotropic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 16
Dependent Claim
38 words
A pharmaceutical composition for treating psychotropic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 17
Dependent Claim
38 words
A pharmaceutical composition for treating psychotropic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-methyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 18
Dependent Claim
38 words
A pharmaceutical composition for treating psychotropic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-methyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 19
Dependent Claim
38 words
A pharmaceutical composition for treating psychotropic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 20
Dependent Claim
38 words
A pharmaceutical composition for treating psychotropic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 21
Independent Claim
247 words
A method of treating warm-blooded animals suffering from psychotropic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound selected from the group consisting of a bicyclic pyrimidin-5-one derivative having the formula ##STR48## the pharmaceutically acceptable acid-addition salts and the stereochemically isomeric forms thereof, wherein: R 1 is hydrogen, lower alkyl or Ar; R 2 is hydrogen, lower alkyl or Ar; R 3 is hydrogen or lower alkyl; Alk is a lower alkanediyl radical; A is a bivalent radical having the formula ##STR49## having the carbon atom attached to the S-atom, wherein R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and lower alkyl and wherein R 4 and R 5 may also complete a saturated or unsaturated 5- or 6-membered carbocyclic ring, optionally substituted with a lower alkyl radical; and Q is a member selected from the group consisting of a radical having the formula --X--Ar (a) wherein X is a member selected from the group consisting of ##STR50## said R 7 being hydrogen or lower alkyl and said q being the integer 2 or 3; and a radical having the formula ##STR51## wherein R 8 is hydrogen or lower alkyl and R 9 , R 10 and R 11 are each independently selected from the group consisting of hydrogen and halo; wherein Ar is phenyl or substituted phenyl, said substituted phenyl bearing an amino group and/or 1,2 or 3 halo atoms.
Claim 22
Independent Claim
247 words
A method of treating warm-blooded animals suffering from psychotropic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound selected from the group consisting of a bicyclic pyrimidin-5-one derivative having the formula ##STR48## the pharmaceutically acceptable acid-addition salts and the stereochemically isomeric forms thereof, wherein: R 1 is hydrogen, lower alkyl or Ar; R 2 is hydrogen, lower alkyl or Ar; R 3 is hydrogen or lower alkyl; Alk is a lower alkanediyl radical; A is a bivalent radical having the formula ##STR49## having the carbon atom attached to the S-atom, wherein R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and lower alkyl and wherein R 4 and R 5 may also complete a saturated or unsaturated 5- or 6-membered carbocyclic ring, optionally substituted with a lower alkyl radical; and Q is a member selected from the group consisting of a radical having the formula --X--Ar (a) wherein X is a member selected from the group consisting of ##STR50## said R 7 being hydrogen or lower alkyl and said q being the integer 2 or 3; and a radical having the formula ##STR51## wherein R 8 is hydrogen or lower alkyl and R 9 , R 10 and R 11 are each independently selected from the group consisting of hydrogen and halo; wherein Ar is phenyl or substituted phenyl, said substituted phenyl bearing an amino group and/or 1,2 or 3 halo atoms.
Claim 23
Dependent Claim
12 words
A method according to claim 13 wherein R 1 is lower alkyl.
Claim 24
Dependent Claim
57 words
A method according to claim 13 wherein R 1 is lower alkyl, Q is a radical of formula (a) wherein X is >C═O or a radical of formula (b) wherein R 9 , R 10 and R 11 are hydrogen, Ar is other than aminophenyl, R 2 is hydrogen or lower alkyl and R 3 is hydrogen.
Claim 25
Independent Claim
38 words
A method of treating warm-blooded animals suffering from psychotropic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-fluorobenzoyl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 26
Independent Claim
38 words
A method of treating warm-blooded animals suffering from psychotropic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-fluorobenzoyl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 27
Independent Claim
38 words
A method of treating warm-blooded animals suffering from psychotropic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 28
Independent Claim
38 words
A method of treating warm-blooded animals suffering from psychotropic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 29
Independent Claim
38 words
A method of treating warm-blooded animals suffering from psychotropic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
Claim 30
Independent Claim
38 words
A method of treating warm-blooded animals suffering from psychotropic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound selected from the group consisting of 6-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one and the pharmaceutically acceptable acid-addition salts thereof.
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) | 1987-04-17 | 1987-10-17 | 1988-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-04-17 | 1991-10-17 | 1992-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-04-17 | 1995-10-17 | 1996-04-17 | $7700.00 | Window Closed / Lapsed |