# US 8,785,452 B2 · Anti-infective compounds

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- Number: US 8,785,452 B2
- Document ID: US8785452B2
- Status: Granted
- Kind: B2
- Application number: 12/999,095
- Filed: 2009-06-17
- Published: 2011-07-21
- Granted: 2014-07-22
- Earliest claimed: 2008-06-17
- Assignees: Institut National de la Sante et de la Recherche Medicale; Institut Pasteur Korea
- Applicants: Priscille Brodin; Thierry Christophe; Zaesung No; Jaeseung Kim; Auguste Genovesio; Denis Philippe Cedric Fenistein; Heekyoung Jeon; Fanny Anne Ewann; Sunhee Kang; Saeyeon Lee; Min Jung Seo; Eunjung Park; Monica Contreras Dominguez; Ji Youn Nam; Eun Hye Kim
- Inventors: Priscille Brodin; Thierry Christophe; Zaesung No; Jaeseung Kim; Auguste Genovesio; Denis Philippe Cedric Fenistein; Heekyoung Jeon; Fanny Anne Ewann; Sunhee Kang; Saeyeon Lee; Min Jung Seo; Eunjung Park; Monica Contreras Dominguez; Ji Youn Nam; Eun Hye Kim
- Web page: https://patentgrep.com/patent/US8785452B2

## CPC

- A61P 31/04: Antibacterial agents
- C12Q 1/18: Testing for antimicrobial activity of a material
- A61P 31/06: for tuberculosis
- C07C 255/66: having cyano groups and nitrogen atoms being part of hydrazine or hydrazone groups bound to the same carbon skeleton
- C07C 335/40: having nitrogen atoms of thiourea or isothiourea groups further bound to other hetero atoms
- C07D 223/24: with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D 233/84: Sulfur atoms
- C07D 251/52: with an oxygen or sulfur atom attached to the third ring carbon atom
- C07D 251/66: Derivatives of melamine in which a hetero atom is directly attached to a nitrogen atom of melamine
- C07D 271/113: with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D 471/04: Ortho-condensed systems
- C07D 498/04: Ortho-condensed systems
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C12Q: MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS (immunoassay G01N33/53); COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to 4H-pyrido[1,2-a]pyrimidin-4-one compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

## Claims

### Claim 1

A compound having the general formula VIIIa:
wherein
X5 is selected from the group consisting of CH2 and C═O;
Z1 is selected from the group consisting of alkoxy, alkylamino, alkylether, alkylthio, alkynyl, amido, amino, aryl, arylalkoxy, arylamino, arylthio, carboxy, cyano, cycloalkyl, ester, halo, haloalkoxy, haloalkyl, heteroaryl, heteroarylamino, heterocycloalkyl, and hydroxyl, any of which is optionally substituted;
Z2 is selected from the group consisting of alkoxy, alkyl, alkylamino, alkylether, alkylthio, alkynyl, amido, amino, aryl, arylalkoxy, arylamino, arylthio, carboxy, cyano, cycloalkyl, ester, halo, haloalkoxy, haloalkyl, heteroaryl, heteroarylamino, heterocycloalkyl, hydroxyl, and hydrogen, any of which is optionally substituted;
R27 and R28 are each independently selected from the group consisting of alkoxy, alkyl, alkyl amino, alkeny, alkylether, alkylthio, alkynyl, amido, amino, aryl, arylether, arylalkoxy, arylamino, arylthio, carboxy, cyano, cycloalkyl, ester, halo, haloalkoxy, haloalkyl, heteroaryl, heteroarylamino, heterocycloalkyl, hydroxyl, hydrogen, nitro, thiol, sulfonate, sulfonyl and sulfonylamino, any of which is optionally substituted; and
R29 and R30 are each independently selected from the group consisting of alkoxy, alkyl, alkylamino, alkenyl, alkylether, alkylthio, alkynyl, amido, amino, aryl, arylether, arylalkoxy, arylamino, arylthio, carboxy, cyano, cycloalkyl, ester, halo, haloalkoxy, haloalkyl, heteroaryl, heteroarylamino, heterocycloalkyl, hydroxyl, hydrogen, nitro, thiol, sulfonate, sulfonyl and sulfonylamino, or two groups are connected to each other to make five or six membered cyclic, heterocyclic, aryl, and heteroaryl rings, any of which is optionally substituted,
wherein Z1 and Z2 may be connected to each other to make five or six membered cyclic, heterocyclic and heteroaryl rings, any of which is optionally substituted.

### Claim 2 (depends on 1)

The compound according to claim 1, having a formula selected from the group consisting of the following formulae 147-159, 173, 180-183, 188, 189, 198-221, 225-238, and 245-301:
9-Methyl-4-oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (147)
2-(3-Chlorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (148)
2-(3-Chlorophenylamino)-8-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (149)
2-(3-Chlorophenylamino)-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (150)
2-(3-Chlorophenylamino)-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (151)
2-(3-Fluorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (152)
9-Methyl-4-oxo-2-(3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (153)
9-Methyl-4-oxo-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (154)
9-Methyl-2-(3-nitrophenylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (155)
2-(3-(Methoxycarbonyl)phenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (156)
2-(3-Hydroxyphenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (157)
2-(4-Hydroxyphenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (158)
2-(4-tert-Butylphenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (159)
2-(3-Chlorophenylamino)-8-(4-methylpiperazin-1-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (173)
Ethyl 4-oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (180)
Ethyl 2-(3-hydroxyphenylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (181)
Ethyl 2-(2-hydroxyphenylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (182)
Ethyl 2-(3-nitrophenylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (183)
Methyl 2-(3-chlorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (188)
Methyl 2-(3-chlorobenzylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (189)
2-(3-Chloro-4-fluorophenylamino)-9-methoxy-N-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxamide (198)
2-(3-Chlorophenylamino)-3-((cyclopentylamino)methyl)-4H-pyrido[1,2-a]pyrimidin-4-one (201)
2-(3-Chlorophenylamino)-3-((cyclohexylamino)methyl)-4H-pyrido[1,2-a]pyrimidin-4-one (202)
2-(3-Chlorophenylamino)-3-((cycloheptylamino)methyl)-4H-pyrido[1,2-a]pyrimidin-4-one (203)
2-(3-Chlorophenylamino)-3-((isopropylamino)methyl)-4H-pyrido[1,2-a]pyrimidin-4-one (204)
2-(3-Chlorophenylamino)-3-((cyclohexylamino)methyl)-8-(4-methylpiperazin-1-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (205)
3-(Hydroxymethyl)-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (206)
2-(3-Chlorophenylamino)-3-(hydroxy methyl)-4H-pyrido-[1,2-a]pyrimidin-4-one (207)
2-(3-Fluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (208)
3-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (209)
3-(Hydroxymethyl)-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (210)
Methyl 3-(3-(hydroxymethyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-ylamino)benzoate (211)
3-(3-(hydroxymethyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-ylamino)benzoic acid (212)
2-(4-Chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (213)
2-(2-Chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (214)
3-(Hydroxymethyl)-2-(3-hydroxyphenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (215)
3-(Hydroxymethyl)-2-(4-hydroxyphenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (216)
3-(Hydroxymethyl)-2-(2-hydroxyphenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (217)
2-(2,6-Dichlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (218)
2-(3,5-Dichlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (219)
2-(3,5-Difluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (220)
2-(2,6-Dimethylphenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (221)
3-(Hydroxymethyl)-9-methyl-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (231)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (232)
2-((3-Chlorophenyl)(methyl)amino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (233)
2-((3-Chlorophenyl)(methyl)amino)-3-(methoxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (234)
3-(Hydroxymethyl)-9-methyl-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (235)
3-(Hydroxymethyl)-2-(3-hydroxyphenylamino)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (236)
3-(Hydroxymethyl)-2-(4-hydroxyphenylamino)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (237)
2-(4-tert-Butylphenylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (238)
7-Bromo-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (245)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-7-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (246)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (247)
8-Chloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (248)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-(methylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (249)
2-(3-Chlorophenylamino)-8-(diethylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (250)
3-(Hydroxymethyl)-8-morpholino-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (251)
2-(3-Fluorophenylamino)-3-(hydroxymethyl)-8-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (252)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (253)
3-(Hydroxymethyl)-8-(4-methylpiperazin-1-yl)-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (254)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-(4-methylpiperazin-1-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (255)
2-(3-Fluorophenylamino)-3-(hydroxymethyl)-8-(4-methylpiperazin-1-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (256)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (257)
2-(4-Chlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (258)
2-(4-Fluorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (259)
2-(3,4-Dichlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (260)
2-(3-Chloro-4-fluorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (261)
9-Chloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (262)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-(trifluoromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (263)
2-(3-Chlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (264)
2-(4-Chlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (265)
9-Fluoro-2-(4-fluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (266)
2-(3-Chloro-4-fluorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (267)
2-(3,4-Difluorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (268)
2-(3,4-Dichlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (269)
2-(1H-Indol-5-ylamino)-9-fluoro-3-(hydroxymethyl)-4,1-pyrido[1,2-a]pyrimidin-4-one (270)
3-(Hydroxymethyl)-9-methoxy-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (271)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (273)
2-(4-Chlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (274)
2-(4-Fluorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (275)
3-(Hydroxymethyl)-9-methoxy-2-(4-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (276)
3-(Hydroxymethyl)-9-methoxy-2-(4-(trifluoromethyl)phenyl amino)-4H-pyrido one (277)
2-(3-Chloro-4-fluorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (278)
2-(3,4-Difluorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (279)
2-(3-Chloro-4-hydroxyphenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido one (280)
2-(3,4-Dichlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (281)
3-(Hydroxymethyl)-9-methoxy-2-(4-methyl-3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (282)
2-(4-Fluoro-3-(trifluoromethyl)phenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (283)
2-(2,3-Dihydro-1H-inden-5-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (284)
2-(Benzo[d][1,3]dioxol-5-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (285)
2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (286)
3-(Hydroxymethyl)-9-methoxy-2-(1-methyl-1H-indol-5-ylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (287)
3-(Hydroxymethyl)-9-methoxy-2-(1-methyl-1H-benzo[d]imidazol-5-ylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (288)
3-(Hydroxymethyl)-9-methoxy-2-(1-methyl-1H-indazol-5-ylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (289)
9-(Difluoromethoxy)-2-(4-fluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (290)
2-(4-Chlorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (291)
9-(Difluoromethoxy)-2-(3,4-difluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (292)
2-(3,4-Dichlorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (293)
2-(3-Chloro-4-fluorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (294)
2-(1H-Indol-5-ylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (295)
2-(3-chlorophenylamino)-3-(hydroxymethyl)-6,8-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one (296)
7,9-Dichloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (297)
2-(3-Chlorophenylamino)-7,9-difluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (298)
(4-Oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-3-yl)methyl benzoate (299)
(4-Oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-3-yl)methyl acetate (300)
and
(4-Oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-3-yl)methyl isobutyrate (301)

### Claim 3 (depends on 2)

The compound, according to claim 2, having a formula selected from the group consisting of the following formulae 180, 199-201, 204, 206-221, 226, 229, 231-238, 245-278, 280-286 and 290-301:
Ethyl 4-oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (180)
2-(3-Chlorophenylamino)-3-((cyclopentylamino)methyl)-4H-pyrido[1,2-a]pyrimidin-4-one (201)
2-(3-Chlorophenylamino)-3-((isopropylamino)methyl)-4H-pyrido[1,2-a]pyrimidin-4-one (204)
3-(Hydroxymethyl)-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (206)
2-(3-Chlorophenylamino)-3-(hydroxy methyl)-4H-pyrido-[1,2-a]pyrimidin-4-one (207)
2-(3-Fluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (208)
3-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (209)
3-(Hydroxymethyl)-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (210)
Methyl 3-(3-(hydroxymethyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-ylamino)benzoate (211)
3-(3-(hydroxymethyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-ylamino)benzoic acid (212)
2-(4-Chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (213)
2-(2-Chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (214)
3-(Hydroxymethyl)-2-(3-hydroxyphenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (215)
3-(Hydroxymethyl)-2-(4-hydroxyphenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (216)
3-(Hydroxymethyl)-2-(2-hydroxyphenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (217)
2-(2,6-Dichlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (218)
2-(3,5-Dichlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (219)
2-(3,5-Difluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (220)
2-(2,6-Dimethylphenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (221)
3-(Hydroxymethyl)-9-methyl-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (231)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (232)
2-((3-Chlorophenyl)(methyl)amino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (233)
2-((3-Chlorophenyl)(methyl)amino)-3-(methoxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (234)
3-(Hydroxymethyl)-9-methyl-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (235)
3-(Hydroxymethyl)-2-(3-hydroxyphenylamino)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (236)
3-(Hydroxymethyl)-2-(4-hydroxyphenylamino)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (237)
2-(4-tert-Butylphenylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (238)
7-Bromo-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (245)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-7-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (246)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (247)
8-Chloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (248)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-(methylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (249)
2-(3-Chlorophenylamino)-8-(diethylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (250)
3-(Hydroxymethyl)-8-morpholino-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (251)
2-(3-Fluorophenylamino)-3-(hydroxymethyl)-8-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (252)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (253)
3-(Hydroxymethyl)-8-(4-methylpiperazin-1-yl)-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (254)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-(4-methylpiperazin-1-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (255)
2-(3-Fluorophenylamino)-3-(hydroxymethyl)-8-(4-methylpiperazin-1-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (256)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (257)
2-(4-Chlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (258)
2-(4-Fluorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (259)
2-(3,4-Dichlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (260)
2-(3-Chloro-4-fluorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (261)
9-Chloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (262)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-(trifluoromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (263)
2-(3-Chlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (264)
2-(4-Chlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (265)
9-Fluoro-2-(4-fluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (266)
2-(3-Chloro-4-fluorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (267)
2-(3,4-Difluorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (268)
2-(3,4-Dichlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (269)
2-(1H-Indol-5-ylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (270)
3-(Hydroxymethyl)-9-methoxy-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (271)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (273)
2-(4-Chlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (274)
2-(4-Fluorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (275)
3-(Hydroxymethyl)-9-methoxy-2-(4-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (276)
3-(Hydroxymethyl)-9-methoxy-2-(4-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (277)
2-(3-Chloro-4-fluorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (278)
2-(3-Chloro-4-hydroxyphenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (280)
2-(3,4-Dichlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (281)
3-(Hydroxymethyl)-9-methoxy-2-(4-methyl-3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (282)
2-(4-Fluoro-3-(trifluoromethyl)phenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (283)
2-(2,3-Dihydro-1H-inden-5-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (284)
2-(Benzo[d][1,3]dioxol-5-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (285)
2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (286)
9-(Difluoromethoxy)-2-(4-fluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (290)
2-(4-Chlorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (291)
9-(Difluoromethoxy)-2-(3,4-difluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (292)
2-(3,4-Dichlorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (293)
2-(3-Chloro-4-fluorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (294)
2-(1H-Indol-5-ylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (295)
2-(3-chlorophenylamino)-3-(hydroxymethyl)-6,8-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one (296)
7,9-Dichloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (297)
2-(3-Chlorophenylamino)-7,9-difluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (298)
(4-Oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-3-yl)methyl benzoate (299)
(4-Oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-3-yl)methyl acetate (300)
and
(4-Oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-3-yl)methyl isobutyrate (301)

### Claim 4

A compound having a formula selected from the group consisting of the following formulae 125, 126, and 132-143:
2-Hydroxy-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (125)
2-Hydroxy-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (126)
9-Methyl-4-oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (132)
2-(3-Chlorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (133)
9-Methyl-4-oxo-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (134)
9-Methyl-4-oxo-2-(3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (135)
2-(4-tert-Butylphenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (136)
2-(3-Chlorobenzylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (137)
9-Methyl-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (138)
2-(4-(2-Chlorophenyl)piperazin-1-yl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (139)
2-(3,4-Dihydroisoquinolin-2(1H)-yl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (140)
2-(Isobutylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (141)
2-(Diethylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (142)
and
2-(Cyclohexylmethylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (143)

### Claim 5

A compound having a formula selected from the group consisting of the following formulae 147-173, 188-189, 198, 205 and 231-298:
9-Methyl-4-oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (147)
2-(3-Chlorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (148)
2-(3-Chlorophenylamino)-8-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (149)
2-(3-Chlorophenylamino)-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (150)
2-(3-Chlorophenylamino)-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (151)
2-(3-Fluorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (152)
9-Methyl-4-oxo-2-(3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (153)
9-Methyl-4-oxo-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (154)
9-Methyl-2-(3-nitrophenylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (155)
2-(3-(Methoxycarbonyl)phenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (156)
2-(3-Hydroxyphenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (157)
2-(4-Hydroxyphenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (158)
2-(4-tert-Butylphenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (159)
2-(3-Chlorobenzylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (160)
2-(Diethylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (161)
2-(Isobutylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (162)
2-(Cyclohexylmethylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (163)
2-(Cyclohexylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (164)
2-(Cyclopentylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (165)
2-(Cycloheptylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (166)
2-(1-(tert-Butoxycarbonyl)piperidin-4-ylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (167)
2-(2-(4-Fluorophenoxy)ethylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (168)
9-Methyl-4-oxo-2-(2-(4-(trifluoromethoxy)phenoxy)ethylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (169)
9-Methyl-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (170)
2-(3,4-Dihydroisoquinolin-2(1H)-yl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (171)
2-(4-(2-Chlorophenyl)piperazin-1-yl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (172)
2-(3-Chlorophenylamino)-8-(4-methylpiperazin-1-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (173)
Methyl 2-(3-chlorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (188)
Methyl 2-(3-chlorobenzylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (189)
2-(3-Chloro-4-fluorophenylamino)-9-methoxy-N-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxamide (198)
2-(3-Chlorophenylamino)-3-((cyclohexylamino)methyl)-8-(4-methylpiperazin-1-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (205)
3-(Hydroxymethyl)-9-methyl-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (231)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (232)
2-((3-Chlorophenyl)(methyl)amino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (233)
2-((3-Chlorophenyl)(methyl)amino)-3-(methoxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (234)
3-(Hydroxymethyl)-9-methyl-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (235)
3-(Hydroxymethyl)-2-(3-hydroxyphenylamino)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (236)
3-(Hydroxymethyl)-2-(4-hydroxyphenylamino)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (237)
2-(4-tert-Butylphenylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (238)
2-(3-Chlorobenzylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (239)
3-(Hydroxymethyl)-2-(isobutylamino)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (240)
2-(Diethylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (241)
2-(Cyclohexylmethylamino)-3-(hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (242)
3-(Hydroxymethyl)-9-methyl-2-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (243)
3-(Hydroxymethyl)-9-methyl-2-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride (244)
7-Bromo-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (245)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-7-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (246)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (247)
8-Chloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (248)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-(methylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (249)
2-(3-Chlorophenylamino)-8-(diethylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (250)
3-(Hydroxymethyl)-8-morpholino-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (251)
2-(3-Fluorophenylamino)-3-(hydroxymethyl)-8-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (252)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (253)
3-(Hydroxymethyl)-8-(4-methylpiperazin-1-yl)-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (254)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-(4-methylpiperazin-1-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (255)
2-(3-Fluorophenylamino)-3-(hydroxymethyl)-8-(4-methylpiperazin-1-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (256)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (257)
2-(4-Chlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (258)
2-(4-Fluorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (259)
2-(3,4-Dichlorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (260)
2-(3-Chloro-4-fluorophenylamino)-3-(hydroxymethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (261)
9-Chloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (262)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-(trifluoromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (263)
2-(3-Chlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (264)
2-(4-Chlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (265)
9-Fluoro-2-(4-fluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (266)
2-(3-Chloro-4-fluorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (267)
2-(3,4-Difluorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (268)
2-(3,4-Dichlorophenylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (269)
2-(1H-Indol-5-ylamino)-9-fluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (270)
3-(Hydroxymethyl)-9-methoxy-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (271)
2-(3-Chlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (273)
2-(4-Chlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (274)
2-(4-Fluorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (275)
3-(Hydroxymethyl)-9-methoxy-2-(4-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (276)
3-(Hydroxymethyl)-9-methoxy-2-(4-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (277)
2-(3-Chloro-4-fluorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (278)
2-(3,4-Difluorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (279)
2-(3-Chloro-4-hydroxyphenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (280)
2-(3,4-Dichlorophenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (281)
3-(Hydroxymethyl)-9-methoxy-2-(4-methyl-3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (282)
2-(4-Fluoro-3-(trifluoromethyl)phenylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (283)
2-(2,3-Dihydro-1H-inden-5-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (284)
2-(Benzo[d][1,3]dioxol-5-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (285)
2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-ylamino)-3-(hydroxymethyl)-9-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one (286)
3-(Hydroxymethyl)-9-methoxy-2-(1-methyl-1H-indol-5-ylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (287)
3-(Hydroxymethyl)-9-methoxy-2-(1-methyl-1H-benzo[d]imidazol-5-ylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (288)
3-(Hydroxymethyl)-9-methoxy-2-(1-methyl-1H-indazol-5-ylamino)-4H-pyrido[1,2-a]pyrimidin-4-one (289)
9-(Difluoromethoxy)-2-(4-fluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (290)
2-(4-Chlorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (291)
9-(Difluoromethoxy)-2-(3,4-difluorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (292)
2-(3,4-Dichlorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (293)
2-(3-Chloro-4-fluorophenylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (294)
2-(1H-Indol-5-ylamino)-9-(difluoromethoxy)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (295)
2-(3-chlorophenylamino)-3-(hydroxymethyl)-6,8-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one (296)
7,9-Dichloro-2-(3-chlorophenylamino)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (297)
and
2-(3-Chlorophenylamino)-7,9-difluoro-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (298)

### Claim 6

A compound having a formula selected from the group consisting of the following formulae 132-135, 137, 139-140, 147, 151-152, 160, 163, and 173:
9-Methyl-4-oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (132)
2-(3-Chlorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (133)
9-Methyl-4-oxo-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (134)
9-Methyl-4-oxo-2-(3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (135)
2-(3-Chlorobenzylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (137)
2-(4-(2-Chlorophenyl)piperazin-1-yl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (139)
2-(3,4-Dihydroisoquinolin-2(1H)-yl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (140)
9-Methyl-4-oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (147)
2-(3-Chlorophenylamino)-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (151)
2-(3-Fluorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (152)
2-(3-Chlorobenzylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (160)
2-(Cyclohexylmethylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (163)
and
2-(3-Chlorophenylamino)-8-(4-methylpiperazin-1-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (173)

### Claim 7

A compound having a formula selected from the group consisting of the following formulae 129-131, 144-146, 174-177 and 187:
2-Chloro-8-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (129)
2-Chloro-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (130)
2-Chloro-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (131)
2-Chloro-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (144)
2-Chloro-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (145)
2-Chloro-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (146)
Ethyl 9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (174)
9-Methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (175)
3-(Hydroxymethyl)-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (176)
9-Methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (177)
and
Methyl 2-chloro-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (187)

### Claim 8

A compound having the general formula VIIIa:
wherein
X5 is C═O;
Z1 and Z2 are each independently selected from the group consisting of alkoxy, alkyl, alkylamino, alkenyl, alkylether, alkylthio, alkynyl, amido, amino, aryl, arylalkoxy, arylamino, arylthio, carboxy, cyano, cycloalkyl, ester, halo, haloalkoxy, haloalkyl, heteroaryl, heteroarylamino, heterocycloalkyl, hydroxyl, and hydrogen, or any two groups are connected to each other to make five or six membered cyclic, heterocyclic and heteroaryl rings, any of which is optionally substituted;
R27 is selected from the group consisting of alkoxy, alkyl, alkyl amino, alkenyl, alkylether, alkylthio, alkynyl, amido, amino, aryl, arylether, arylalkoxy, arylamino, arylthio, carboxy, cyano, cycloalkyl, ester, halo, haloalkoxy, haloalkyl, heteroaryl, heteroarylamino, heterocycloalkyl, hydroxyl, hydrogen, nitro, thiol, sulfonate, sulfonyl and sulfonylamino, any of which is optionally substituted;
R28 is selected from the group consisting of alkoxy, alkyl, alkylamino, alkenyl, alkylether, alkylthio, alkynyl, amido, amino, aryl, arylether, arylalkoxy, arylamino, arylthio, carboxy, cyano, cycloalkyl, ester, halo, haloalkoxy, haloalkyl, heteroaryl, heteroarylamino, heterocycloalkyl, hydroxyl, nitro, thiol, sulfonate, sulfonyl and sulfonylamino, any of which is optionally substituted; and
R29 and R30 are each independently selected from the group consisting of alkoxy, alkyl, alkylamino, alkenyl, alkylether, alkylthio, alkynyl, amido, amino, aryl, arylether, arylalkoxy, arylamino, arylthio, carboxy, cyano, cycloalkyl, ester, halo, haloalkoxy, haloalkyl, heteroaryl, heteroarylamino, heterocycloalkyl, hydroxyl, hydrogen, nitro, thiol, sulfonate, sulfonyl and sulfonylamino, or two groups are connected to each other to make five or six membered cyclic, heterocyclic, aryl, and heteroaryl rings, any of which is optionally substituted.

### Claim 9 (depends on 8)

The compound according to claim 8, having a formula selected from the group consisting of the following formulae 132-136:
9-Methyl-4-oxo-2-(phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (132)
2-(3-Chlorophenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (133)
9-Methyl-4-oxo-2-(3-(trifluoromethoxy)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (134)
9-Methyl-4-oxo-2-(3-(trifluoromethyl)phenylamino)-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (135)
and
2-(4-tert-Butylphenylamino)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (136)

### Claim 10 (depends on 2)

A pharmaceutical composition comprising a compound of claim 2 and a carrier.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 and a carrier.

### Claim 12 (depends on 3)

A pharmaceutical composition comprising a compound of claim 3 and a carrier.

### Claim 13 (depends on 4)

A pharmaceutical composition comprising a compound of claim 4 and a carrier.

### Claim 14 (depends on 5)

A pharmaceutical composition comprising a compound of claim 5 and a carrier.

### Claim 15 (depends on 6)

A pharmaceutical composition comprising a compound of claim 6 and a carrier.

### Claim 16 (depends on 7)

A pharmaceutical composition comprising a compound of claim 7 and a carrier.

### Claim 17 (depends on 8)

A pharmaceutical composition comprising a compound of claim 8 and a carrier.

### Claim 18 (depends on 9)

A pharmaceutical composition comprising a compound of claim 9 and a carrier.

### Claim 19 (depends on 1)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 1, wherein the bacterial infection is tuberculosis.

### Claim 20 (depends on 2)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 2, wherein the bacterial infection is tuberculosis.

### Claim 21 (depends on 3)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 3, wherein the bacterial infection is tuberculosis.

### Claim 22 (depends on 4)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 4, wherein the bacterial infection is tuberculosis.

### Claim 23 (depends on 5)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 5, wherein the bacterial infection is tuberculosis.

### Claim 24 (depends on 6)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 6, wherein the bacterial infection is tuberculosis.

### Claim 25 (depends on 7)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 7, wherein the bacterial infection is tuberculosis.

### Claim 26 (depends on 8)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 8, wherein the bacterial infection is tuberculosis.

### Claim 27 (depends on 9)

A method for treating a bacterial infection wherein said method comprises administering a compound of claim 9, wherein the bacterial infection is tuberculosis.