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Generated: June 18, 2018

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Claims for Patent: 5,663,169

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Summary for Patent: 5,663,169
Title: Benzoxazinones as inhibitors of HIV reverse transcriptase
Abstract:Certain benzoxazinones are useful in the inhibition of HIV reverse transcriptase (including its resistant varieties), the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable saks, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
Inventor(s): Young; Steven D. (Lansdale, PA), Payne; Linda S. (Lansdale, PA), Britcher; Susan F. (Norristown, PA), Tran; Lekhanh O. (West Chester, PA), Lumma, Jr.; William C. (Pennsburg, PA)
Assignee: Merck & Co., Inc. (Rahway, NJ)
Application Number:08/458,528
Patent Claims: 1. A method of inhibiting HIV reverse transcriptase comprising administering to a mammal a pharmaceutically acceptable carrier and an effective amount of a compound of Formula I: ##STR82## or pharmaceutically acceptable salt thereof, wherein: X is halo,

X.sup.1 is trihalomethyl, or pentahaloethyl;

Z is O;

R is:

(a) C .sub.1-8 alkyl, unsubsdtuted or substituted with A, and A is halo, C.sub.3-6 cycloalkyl, CN, hydroxy, C.sub.1-4 alkoxy, C.sub.2-4 alkynyl-C.sub.1-4 alkoxy, aryloxy, C.sub.1-4 alkylcarbonyl, nitro, di(C.sub.1-2 alkyl)amino, C.sub.1-4 alkylamino- C.sub.1-2 alkyl, heterocycle, or arylthio;

(b) C.sub.2-4 alkenyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstituted or substituted with A;

(c) C.sub.2-5 alkynyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstituted or substituted with A; or

(d) C.sub.3-4 cycloalkyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstituted or substituted with A,

or a compound of Formula II: ##STR83## or pharmaceutically acceptable salt thereof, wherein: X is halo;

X.sup.1 is trihalomethyl; pentahaloethyl; C.sub.2-5 alkyl;

C.sub.2-5 alkynyl;

C.sub.3-5 cycloalkyl; or aryl;

Z is O or S; and

R is:

(a) C.sub.1-8 alkyl, unsubstituted or substituted with A, and A is halo, C.sub.3-6 cycloalkyl, CN, hydroxy, C.sub.1-4 alkoxy, C.sub.2-4 alkynyl-C.sub.1-4 alkoxy, aryloxy, C.sub.1-4 alkylcarbonyl, nitro, di(C.sub.1-2 alkyl)amino, C.sub.1-4 alkylamino-C.sub.1-2 alkyl, heterocycle, or arylthio;

(b) C.sub.2-4 alkenyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstituted or substituted with A;

(c) C.sub.2-5 alkynyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstituted or substituted with A; or

(d) C.sub.3-4 cycloalkyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstituted or substituted with A.

2. A method of inhibiting HIV reverse transcriptase comprising administering to a mammal a pharmaceutically acceptable carrier and an effective amount of a compound selected from the group consisting of:

(-) 6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxa zin-2-one,

(-) 6-chloro-4-phenylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2 -one, (+/-) 6-chloro-4-(2-cyanophenyl)ethynyl-4-(1,1,1-trifluoromethyl)-1,4-dihydro-2H -3,1-benzoxazin-2-one,

(+/-)4-(1-chloro-1,1-difluoromethyl)-4-(2-phenylethynyl)-6-chloro-1,4-dihyd ro-2H-3,1-benzoxazin-2-one, or

(+/-)4-(2-[dimethylaminomethyl]ethynyl)-4-trifluoromethyl-6-chloro-1,4-dihy dro-2H-3,1-benzoxazin-2-one,

or a pharmaceutically acceptable saIt thereof.

3. A method of preventing infection of HIV, or of treating infection by HIV or of treating AIDS or ARC comprising administering to a mammal a pharmaceutically acceptable carder and an effective mount of a compound of Formula I: ##STR84## or pharmaceutically acceptable salt thereof, wherein: X is halo,

X.sup.1 is trihalomethyl, or pentahaloethyl;

Z is O;

R is:

(a) C.sub.1-8 alkyl, unsubstituted or substituted with A, and A is halo, C.sub.3-6 cycloalkyl, CN, hydroxy, C.sub.1-4 alkoxy, C.sub.2-4 alkynyl-C.sub.1-4 alkoxy, aryloxy, C.sub.1-4 alkylcarbonyl, nitro, di(C.sub.1-2 alkyl)amino, C.sub.1-4 alkylamino- C.sub.1-2 alkyl, heterocycle, or arylthio;

(b) C.sub.2-4 alkenyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstimted or substituted with A;

(c) C.sub.2-5 alkynyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstimted or substituted with A; or

(d) C.sub.3-4 cycloalkyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstimted or substituted with A,

or a compound of Formula II: ##STR85## or pharmaceutically acceptable salt thereof, wherein: X is halo;

X.sup.1 is trihalomethyl; pentahaloethyl; C.sub.2-5 alkyl;

C.sub.2-5 alkynyl;

C.sub.3-5 cycloalkyl; or aryl;

Z is O or S;

R is:

(a) C.sub.1-8 alkyl, unsubstimted or substituted with A, and A is halo, C.sub.3-6 cycloalkyl, CN, hydroxy, C.sub.1-4 alkoxy, C.sub.2-4 alkynyl-C.sub.1-4 alkoxy, aryloxy, C.sub.1-4 alkylcarbonyl, nitro, di(C.sub.1-2 alkyl)amino, C.sub.1-4 alkylamino-C.sub.1-2 alkyl, heterocycle, or arylthio;

(b) C.sub.2-4 alkenyl, unsubstimted or substituted with

(i) A, or

(ii) aryl, unsubstituted or substituted with A;

(c) C.sub.2-5 alkynyl, unsubstituted or substituted with

i) A, or

(ii) aryl, unsubstituted or substituted with A; or

(d) C.sub.3-4 cycloalkyl, unsubstituted or substituted with

(i) A, or

(ii) aryl, unsubstituted or substituted with A.

4. A method of preventing infection of HIV, or of treating infection by HIV or of treating AIDS or ARC, comprising administering to a mammal a pharmaceutically acceptable carder and an effective amount of a compound selected from the group consisting of:

(-) 6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxa zin-2-one,

(-) 6-chloro-4-phenylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2 -one,

(+/-) 6-chloro-4-(2-cyanophenyl)ethynyl-4-(1,1,1-trifluoromethyl)-1,4-dihydro-2H -3,1-benzoxazin-2-one,

(+/-) 4-(1-chloro-1,1-difluoromethyl)-4-(2-phenylethynyl)-6-chloro-1,4-dihydro-2 H-3,1-benzoxazin-2-one, or

(+/-) 4-(2-[dimethylaminomethyl]ethynyl)-4-trifluoromethyl-6-chloro-1,4-dihydro- 2H-3,1-benzoxazin-2-one,

or a pharmaceutically acceptable salt thereof.

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