IP Library Granted Patent US 7,709,491
Granted Patent B2
US 7,709,491 · App. 10/534,138 · Granted May 4, 2010

Substituted quinazolines as antiviral agents, especially against cytomegaloviruses

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Quick Facts
Patent No.
US 7,709,491
App. No.
10/534,138
Granted
May 4, 2010
Kind
B2
Abstract

The invention relates to substituted quinazolines and to methods for the production thereof, in addition to the use thereof in the production of medicaments for the treatment and/or prophylaxis of diseases, especially for use as antiviral agents, especially against cytomegaloviruses.

Claims (38)

1. A compound of the formula

in which

R 1 , R 2 and R 3 are independently of one another hydrogen, alkyl, alkoxy, carboxyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, trifluoromethyl, halogen, cyano, hydroxy or nitro,

R 4 and R 5 are independently of one another hydrogen, alkyl, alkoxy, cyano, halogen, nitro, trifluoromethyl or trifluoromethoxy,

R 6 is alkyl, cyano, halogen, nitro or trifluoromethyl,

R 7 and R 8 are independently of one another hydrogen, halogen, alkyl or alkoxy, and

R 9 is aryl or 1,3-benzodioxol-5-yl in which aryl and 1,3-benzodioxol-5-yl may be substituted by 1 to 3 substituents, where the substituents are selected independently of one another from the group consisting of alkyl, alkoxy, alkylthio, carboxyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, trifluoromethyl, halogen, carbamoyl, cyano, hydroxy, amino, alkylamino, nitro and optionally hydroxy-substituted alkyl,

or a salt thereof.

2. A compound according to claim 1 , in which

R 1 , R 2 and R 3 are independently of one another hydrogen, fluorine, chlorine, cyano, hydroxy, aminocarbonyl or nitro,

R 4 and R 5 are independently of one another hydrogen, fluorine, alkyl or alkoxy,

R 6 is trifluoromethyl, isopropyl or tert-butyl,

R 7 and R 8 are independently of one another hydrogen, halogen, C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy, and

R 9 is phenyl or 1,3-benzodioxol-5-yl in which phenyl may be substituted by 1to 3 substituents, where the substituents are selected independently of one another from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, carboxyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, trifluoromethyl, fluorine, chlorine, bromine, cyano, hydroxy, amino, C 1 -C 6 -alkylamino and nitro,

or a salt thereof.

3. A compound according to claim 1 , in which

R 1 and R 2 are hydrogen,

R 3 is fluorine,

R 4 and R 5 are independently of one another hydrogen, fluorine or alkoxy,

R 6 is trifluoromethyl,

R 7 and R 8 are hydrogen and

R 9 is phenyl, in which phenyl may be substituted by 1 or 2 substituents, where the substituents are selected independently of one another from the group consisting of methyl, methoxy, fluorine and chlorine,

or a salt thereof.

4. A process for preparing a compound of the formula (I) as claimed in claim 1 , comprising the step of reacting a compound of the formula

in which

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 have the meaning indicated in claim 1 , and

R 10 is alkyl, with a base.

5. A pharmaceutical composition comprising a compound according to claim 1 in combination with an inert, nontoxic, pharmaceutically suitable excipient.

6. A pharmaceutical composition according to claim 5 for the treatment of viral infections.

7. A method for treating viral infections in humans and animals by administering an antivirally effective amount of at least one compound according to claim 1 .

8. The method of claim 7 wherein said infection is caused by a virus of the group Herpes viridae.

9. The method of claim 8 wherein said virus is a cytomegalovirus.

10. The method of claim 9 wherein said virus is human cytomegalovirus (HCMV).

11. A method for controlling viral infections in humans and animals by administering an antivirally effective amount of a pharmaceutical composition according to claim 5 .

12. The method of claim 11 wherein said infection is caused by a virus of the group Herpes viridae.

13. The method of claim 12 wherein said virus is a cytomegalovirus.

14. The method of claim 13 wherein said virus is human cytomegalovirus (HCMV).

15. The process of claim 4 wherein R 10 is methyl or ethyl.

Assignments (6)
CHANGE OF NAME Recorded Sep 9, 2021
From: AIC246 GMBH & CO. KG
To: AIC246 AG & CO. KG
Reel/Frame 057447/0605 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 2, 2021
From: AICURIS ANTI-INFECTIVE CURES GMBH
To: AIC246 GMBH & CO. KG
Reel/Frame 057371/0159 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2019
From: AICURIS GMBH & CO. KG
To: AICURIS ANTI-INFECTIVE CURES GMBH
Reel/Frame 048208/0077 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2010
From: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
To: AICURIS GMBH & CO. KG
Reel/Frame 025492/0577 →
MERGER Recorded Jan 12, 2010
From: BAYER HEALTHCARE AG
To: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
Reel/Frame 023769/0122 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2005
From: WUNBERG, TOBIAS; BAUMEISTER, JUDITH; JESKE, MARIO; NIKOLIC, SUSANNE; ZIMMERMANN, HOLGER; SUSSMEIER, FRANK; GROSSER, ROLF; HENNINGER, KERSTIN; HEWLETT, GUY; KELDENICH, JORG; LANG, DIETER; LIN, TSE-I
To: BAYER HEALTHCARE AG
Reel/Frame 016772/0738 →