JPS60228483A - 1h,7h-pyrazolo(1,5-a)pyrimidin-7-one derivative and manufacture - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention]

The present invention relates to novel IH,7H-pyrazo o[1,5-a)pyrimidin-7-one derivatives, processes for their preparation and pharmaceutical compositions containing them. The present invention has the following general formula (1). R1a) C1-C6 alkyl or benzyl. b) unsubstituted or auto-c6 alkyl-substituted pyridyl, C) unsubstituted or halogen, trif-10-methyl, C1
-C6 a*, Cl-C6 alkoxy, hydroxy, formyloxy, C2-C6 alkanoyloxy, nitro, amino, phenyl substituted with - or more substituents selected from formylamino and C2-C6 alkanoylamino . Yes. R2 is a) pyridyl or b) phenyl, unsubstituted or substituted with - or 7' or more substituents selected from halogen, triheromethyl, nitro, Cl-C6 alkoxy and 01-C6 alkyl; R3 is hydrogen or unsubstituted, or halogen, hydroxy sC1-C6 alkoxy, formyloxy, C2-
c6 alkanoyloxy and the group is hydrogen, cl<6 alkyl, phenyl or benzyl, or R5 and R
6 together with their bonded nitrogen atoms. N-imidazolyl, hexahydro-N-acevinyl, N
- substituted with - or more substituents selected from pyrrolidinyl, N-piperazinyl, piperidino, thiomorpholino and morpholino, and forming an unsubstituted or c 1-c 6 alkyl substituted heterocycle is C1-C6 alkyl, and R4 is hydrogen, halogen, CIA-06 alkyl, hydroxyl/, C1-C6
The present invention also provides compounds having the following formula: alkoxy, C3 (4-alkenoyloxy, formyloxy, or c2-c6-alkanoyloxy) and pharmaceutically acceptable salts thereof. It also includes metabolites and metabolic precursors of the compounds of formula (1) and all possible isomers, such as optical isomers and mixtures thereof, of the compounds of formula (1). The amino group can be a branched or straight chain group. The halogen atom is, for example, chlorine, bromine or fluorine, but
It is preferably chlorine or fluorine. The trihalomethyl group is preferably a trifluoromethyl group. A c2-c6 alkanoyloxy group is, for example, acetoxy, propionyloxy, butyryloxy or valeryloxy, preferably it is acetoxy. The C1-C6 alkyl group is preferably a C1-04 alkyl group, especially methyl, ethyl, propyl or tert-butyl. The C1-C6 alkoxy group is preferably cl-1c4
Alkoxy, % methoxy, ethoxy, propoxy or butoxy. A C2''-C,S alkanoylamino group is, for example, acetylamino, propionylamino, butyrylamino or valerylamino, preferably acetylamino. If R1 and/or R2 is phenyl substituted as defined above, or when R3 is C1<6 alkyl substituted as defined above. They are preferably disubstituted with 1,2 or rj3 substituents. R1 is a 01<6 alkyl group If R1 is for example methyl, ethyl, propyl, inpropyl, butyl, isobutyl, t or tert-butyl, preferably it is methyl, ethyl, propyl or tert-butyl. In the case of a pyridyl group substituted with 1 by a group, the alkyl group is, for example, methyl,
Ethyl or propyl, preferably methyl. When R1 and/or R2 is a phenyl ring substituted as defined above, it is more preferably selected from tt, da1 mata fi
It is di-substituted with the substituent of 2. When R3 and/or R4 is an unsubstituted c 1-c 6 alkyl group, it is, for example, methyl. ethyl, propyl, isopropyl or butyl;
Preferably it is methyl, ethyl, propyl or isopropyl. When R3 is an 01-C6 alkyl group substituted by - or more halogen atoms, it is preferably an 01-C3 alkyl group substituted by 1 to 3 chlorine or fluorine atoms. c in which R3 is substituted with - or more 01-C6 alkoxy groups
In the case of a 1-c6 alkyl group, it is preferably
C 1- substituted with ~3 01-C2 alkoxy groups
03 is an alkyl group. If R4 is a halogen atom, it is for example chlorine, bromine or fluorine, preferably it is chlorine or bromine. When R4 is a C1-C6 alkoxy group, it is for example methoxy, ethoxy, propoxy, impropoxy or butoxy, preferably it is methoxy, ethoxy or propoxy, R
one or both of 5 and R6 are the same or different;
When it is a C6 alkyl group it is for example methyl, ethyl, propyl, impropyl or butyl, preferably it is methyl, ethyl, propyl or isopropyl. R5 and R6 together with their bonding nitrogen atoms form a compound as defined above and the group is 01
When substituted by -04 alkyl, the alkyl group is preferably aC1-C4C1-c4 alkyl, or ethyl. Preferred compounds of the invention are R1ka') CI-c4 alkyl or benzyl 5b
l) Unsubstituted or methyl-substituted pyridyl. C unsubstituted or halogen, trifluoromethyl,
cl-c4 alkyl, C1-(l!4 alkoxy, nitro, amino, formylamino and phenyl substituted with one or two substituents selected from C2-C6 alkanoylamino, and R2 is unsubstituted, or R3 is hydrogen or unsubstituted, or chlorine, fluorine. Hydroxy, 01-C4 alkoxy, formyloxy, R
5 ′・0′″<67 k h /i″″shi2yohi base □
6 (in the formula, each of R5 and R6 is independently hydrogen, 01-c
d-alkyl, or phenyl, or R5 and only 6
together with their bonded nitrogen atoms, N-
1-3 selected from imidazolyl, hexahydro-N-azepinyl, N-pyrrolidinyl, N-piperazinyl, piperidino, thiomorpholino and morpholino, and forming an unsubstituted or 01-c3 alkyl-substituted heterocycle) 01-C4 alkyl substituted with 4 substituents, and R4 is hydrogen, halogen, C1-C4 alkyl, hydroxy, C1-C4 alkoxy V% C3-C4 alkenyloxy% or C2-C6 alkanoyloxy (
1) and its pharmaceutically acceptable salts. More preferred compounds of the present invention are: R1 a") Cl-c4 alkyl, benzyl or pyridyl, b") unsubstituted or unsubstituted, fluorine, trifluoromethyl, methyl, Cl-02 alkoxy. It is phenyl substituted with one or two substituents selected from nitro, amino, formylamino and C2-c4 alkanoylamino. R2 is unsubstituted or halogen, trifluoromethyl,
phenyltehF) substituted with one or two substituents selected from nitro, 01-C4 alkyl and 01-C4 alkoxy. R3 is hydrogen, unsubstituted, or halogen. Hydroxy% C1-C2 alkoxy, formyloxy,
C2-C4 alkanoyloxy and the group -N<6, where each R5 and R16 are independently hydrogen or C1<4
Alkyl or R5 and R6 together with the nitrogen atom to which they are attached. Unsubstituted N-imidazolyl, unsubstituted hexahydro-N
- forming a heterocycle selected from azepinyl, unsubstituted N-pyrrolidinyl, unsubstituted or 3-alkyl-substituted N-piperazinyl, unsubstituted or methyl-substituted piperidino and morpholino, and unsubstituted thiomorpholino; 01-4 alkyl substituted with 1 to 5 tilN9L groups selected from
Compounds of formula (1) which are hydroxy, C1-C3 alkoxy, allyloxy, or C2-4 alkanoyloxy, and pharmaceutically acceptable salts thereof. Pharmaceutically acceptable salts include salts with inorganic acids such as nitric acid, hydrochloric acid, hydrobromic acid and sulfuric acid and with organic acids such as citric acid, tartaric acid, maleic acid, malic acid, ferric acid, methanesulfonic acid and ethanesulfonic acid. It is a salt with an acid. Particularly preferred examples of compounds of the invention are as follows. 1.2-diphenyl-5-methyl-IH, 7H-pyrazolo(1,S-a]pyrimidin-7-one. 1.2-diphenyl-5-trifluoromethyl-IH,
7H-pyrazolo[1,5-a]pyrimidin-7-one. 1,2-diphenyl-IH,7H-pyrano” [1,5
-a) Pyrimidin-7-one. 5-Methyl-1-(4-methyl-phenyl)-2-phenyl-IH,7H-pyran0 (L5-a]pyrimidin-7-one. 5-Methyl-1-(4-nitro-phenyl)-2 -Phenyl-IH,7H-pyran o [1,5-a]pyrimidin-7-one. 1-(4-chloro-phenyl)-5-methyl-2-phenyl-IH,7H-pyran o [1,5 -a]pyrimidin-7-one. 1-(3-chloro-7ale)-5-methyl-2-phenyl-IH,7H-pyran o [1,5-a]pyrimidin-7-one. 1-( 4-fluoro-phenyl)-5-methyl-2-phenyl-IH,7H-pyran" (L5-a) pyrimidin-7-one. 5-methyl-2-phenyl-1-(3-)lifluoro methyl-phenyl)-11(,7H-hirazolo[1,5
-a]pyrimidin-7-one, 1-benzyl-5-methyl-2-phenyl-IH,7H-pyran O[1,5-a
] Pyrimidin-7-one. 1-5th blue f-5-methyl-2-phenyl-IH,7
)(-pyran O[1,5-a]pyrimidin-7-one. 1,5-dimethyl-2-phenyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one. 5-methyl- 2-phenyl-1-(2-pyridyl) -
1H,7I(-pyran o [1,5-a]pyrimidine-
7-on. 5-methyl-2-phenyl-1-(5-pyridyl) -
1H,7H-pyran o [l,5-a]pyrimidine-7
-On. 1.2-bis(3-chloro-phenyl)-5-methyl-
1]-1,7H-pyrazolo[1,5-a]pyrimidine-
7-on. 1-(5-chloro-phenyl)-2-(4-methoxy-
fer)-5-methyl-IH,7H-pyrazolo[1,
5-a] pyrimidin-7-one. 1,2-diphenyl-5,6-dimethyl-IH,7H-
Pyrazolo [L5-a, J pyrimidin-7-one. 6-10Rho 1,2-diphenyl-5-mef-Rhu I
H,7H-virazo' [1*5-a) pyrimidine-7-
on, 1,2-diphenyl-6-medoxy5-methyl-IH
,7H-pyrano [L5-a) Pyrimidin-7-one. 1.2-diphenyl-6-ethoxy5-methyl-IH
, 7I (-pyrazolo, 5-a) pyrimidin-7-one. 5-(N,N-diethylamino-methyl)-1,2-
diphenyl-IH,7H-pyran' (L5-a) pyribadin-7-one, 1,2-diphenyl-5-(pyrrolidin-1-yl-methyl) -1H,7H-pyrazolo(1,5-a ) pyrimidin-7-one. 1,2-diphenyl-5-(imidazol-1-yl-
methyl) -1H,7H-pyran" [1,5-a]pyrimidin-7-one. 1,2-diphenyl-5-methoxymethyl-IH. 7H-pyrazolo[1,5-a]pyrimidin-7-one and their pharmacologically measurable salts, the compounds of the present invention have a) the following formula (II) and R7 is a compound of the formula (which is a nucleophilic ≠ medium ≠ group that can be cleaved from the anthrax atom to which it is bonded during the closure of the chemical compound or a salt thereof) b )Next 2〇ll) (In the formula, R1 and R7u through the above definition, and R
8 is hydrogen or unsubstituted C1-C6 alkyl) is decarboxylated to obtain a compound of formula (1) where R3 is hydrogen or unsubstituted C, -06 alkyl, p and R4 is hydrogen. or (wherein R1, R2 and R8 are as defined above,
And each of R9 and Rln is independently self-c.
6 alkyl) is thermally ring-closed to form a compound in which R3 is a water reservoir or unsubstituted C1-C6 alkyl, and R4
is lime scale, and optionally converting the compound of formula (1) to other compounds of formula (1), and/or P9r optionally converting the compound of formula (1) to other compounds of formula (1). 1
) into its physiologically acceptable salt, and/or optionally converting the compound of the formula
Where R7 is a nucleophilic group as defined above, it can be prepared by a process comprising forming the free compound and/or optionally separating the isomer mixture into single isomers. For example, it is hydroxy, tri(~Cs)alkyl-silyloxy or c 1
-c 6 Alfoxy, the compound 2〇) is reciprocal,
T can also be represented by the formula (Ha)R70C' R4 \/ (wherein R1, R2, R3, R4 and R7 are as defined above). Preferred salts of compounds of formula 0 are, for example, with inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid and (iiiic acid). At temperatures between 50 and about 150° C., the acid condensation agent is carried out by treatment with polyphosphoric acid (alone or in the presence of Ogishihanka phosphorus) with sulfuric acid, side L methanesulfonic acid or p-)luenesulfonic acid. The reaction can be carried out in organic solvents such as dimethylformamide, dimethylacetamide, dimethyl sulfoxide, benzene, toluene, chiresine, ethylene glycol monomethyl ether, or dichloroethane, but it is preferably carried out in the absence of solvent. Alternatively, the ring closure of the compound of formula (II) is carried out by dissolving the compound in an inert high-boiling organic solvent, eg evadiphenyl ether, at a temperature in the range from about 150 to about 350°C, preferably from 200 to 300°C. Decarboxylation of compounds of formula (2) can also be carried out by heating in the absence of a solvent.Decarboxylation of compounds of formula (2) can be carried out, for example, in the presence of copper powder in a solvent such as quinoline, at a temperature between 150 and 200°C. or by melting in the presence of CuO at a temperature between 200 and 300° C. Thermal closure of the compound of formula (mV) can be carried out, for example, by heating to Examples of active solvents are nitrobenzene, diethyl phthalate,
in mineral oil, diphenyl ether or Dowtherm A (eutectic mixture of diphenyl and diphenyl ether),
VCX treatment can be carried out by heating to a temperature of 200 to 300C, preferably 260 to 270C. The compound of formula (1) can be prepared by the known method as described above.
It can be converted into other compounds of 1). For example, Fi free hydroxyl group Fi base such as NaOH, KOH
, Na2CO3, Na)1. In the presence of NaNH2, sodium methoxide, x2co5 or sodium ethoxide, a solvent selected from the group consisting of, for example, methanol, ethanol, dioxane, acetone, dimethylformamide, hexamethylphosphorotriamide, tetrahydrofuran, water and mixtures thereof. In addition, the etherified hydroxy group can be etherified by reaction with a suitable alkyl halide, preferably at a temperature in the range from about Ω to about 150C; Hydrogen or Lewis acids such as AlCl2. '! or BBr3, it can be converted to a free hydroxyl group. Further illustratively, the nitro group is optionally treated in an organic solvent such as acetic acid. Amine groups can be converted to f by treatment with stannous chloride in concentrated hydrochloric acid at temperatures from room temperature to about 100° C. using dioxane, tetrahydrofuran. Further illustration: an amino or hydroxy group can be prepared without solvent, for example with formic acid or with the corresponding alkanoyl anhydride,
or from 0 to about 1000 in an organic solvent such as dioxane, dimethylformamide, tetrahydrofuran, usually in the presence of a base such as pyridine or triethylamine.
formylamino, 02-C6 kanoylamino or 02-C6 by reacting at a temperature of
Further, the compound of formula (1) in which R4 is hydrogen, which can be converted into an alkanoyloxy group, can be reacted with a suitable halogenating agent such as chlorosuccinimide or promosuccinimide, 807C42 or pyridinium bromid perpromide at a temperature in the range of Q 0 to 100°C. cct4 at a temperature of 1, e.g. in the case of reaction with 5o2cz2 as solvent
or dichloroethane is reacted by operating with pyridine in the reaction with pyridinium bromide perpromide and with inzene in the reaction with herosuccinimide of the formula ( It can be converted into the compound of 1)≧. Furthermore, for example, c1 to C6 in which R3 is substituted with a herogen atom
Compounds of formula 0) which are alkyl groups can be reacted at temperatures between 20° and 150° C. with organic solvents such as methyl ethyl ketone, toluene, xylene, dimethylform (wherein R5 and R6 are as previously defined) groups. -c 6
It can be converted into a compound of formula (1) which is an alkyl group. Also, any salt formation of the compound of formula (1) and the conversion of the salt into the free compound and the separation of the isomer mixture into single isomers can be carried out by conventional methods. For example, separation of optical isomer mixtures into individual isomers can be carried out by salt formation using optically active bases or acids and subsequent fractional crystallization. The compound of formula (1) is, for example, a compound of formula (V) (wherein R1 and R2 are as defined above) or a compound thereof (formula LVI) R7°C\/R4 (wherein R3) R4 and R7 is as defined above, and R11t; is preferably hydroxy, amine, 01
-C6 alkoxy, or tri(01-Cs)alkyl-silyloxy). Preferred salts of the compound of formula (V) are with free acids such as hydrochloric acid, hydrobromic acid, phosphoric acid and sulfuric acid. The reaction between the compound of formula (■ and the compound of formula (Vl) is, for example,
For example, dioxane, toluene, xylene, acetonitrile, cl-c4 alkyl alcohol, acetic acid,
in dimethylformamide, dimethylacetamide, diphenyl ether or in the absence of a solvent from room temperature to about 2
Preferably, when August is hydroxy, the reaction between the compound of formula (■) and the compound of formula (Vl) can be carried out by heating at a temperature of It is carried out using the same experimental conditions as described for the ring closure of the compound of formula (II) above in the presence of the acid 5p-)luenesulfonic acid or acetic acid. Under these specific conditions, the formula (I
The reaction between compounds of formula 1 (■ and formula CM) can be carried out without the need to isolate the intermediate products of I) until compounds of formula 0) are obtained. The compound of formula (2) is, for example, 1 formula (■) (in the formula R1*
R2 and R3 are the same as above and R12 is a cyano or Nisderyl carboxy group or a tri(C,S)alkyl-silyloxycarbonyl group), such as mineral acids such as HCt, HBr5H, etc. in water or in acetic acid or dioxane or a mixture thereof. It can be produced by treatment and hydrolysis at temperatures ranging from room temperature to about 120°C. The compound of formula LfV) is, for example, the compound of formula (V) RB-C(QRls)s (■) (wherein R8 is as defined above, and R and 5 are self- to 06 alkyl) and a compound of formula (IK) (wherein R
9 and R10 are as defined above). The reaction of a compound of formula (mV) with a mixture of a compound of formula (■) and a compound of formula (K) can be carried out, for example, without a solvent or in an inert solvent such as benzene, ethanol, dioxane, tetrahydrofuran, acetonitrile, dimethylformamide. The present invention can be carried out at temperatures from room temperature to about 150<0>C. The compound of formula (■) is a compound of formula (X) (wherein R1, 2s, R5-R7 and R12 are as defined above) to the closing plate of the compound of formula (...). Can be prepared by ring closure using the same experimental conditions as specifically described. The compounds of the formulas LV), (Vl), (■) and (K) are known compounds or can be prepared by conventional methods. In some cases, they are commercially available products. The compounds of this invention are active in the central nervous system (CN8) and are active in 1% as central nervous system depressants, ie, sedatives, anticonvulsants, minor 7-chillizers, and somnolants. CNS of uninvented compounds
For example, Irwin's technique [I rv
1 n * S −tPSychOpbarmaQOI
Ogla (Berl,) + 13 + 222 + (196
8)) was evaluated using the experimental thread of behavioral evaluation. In this test, the compound 8F41J of the present invention was active in CNB inhibition, particularly as a sedative and secondary tranquilizer, and in hypnotic induction in mice and rats, for example. Animals treated with oral doses ranging from 5 to 10019/IKt body weight showed concomitant muscle tone, respiratory rate, rectal temperature and other smaller indicative reflexes.
He showed loss of righting reflex without inhibition of active reflex. The toxicity of the compounds of the invention is negligible. They can therefore be safely used in therapy. 9
Mice and rats that had been deprived of food for a period of time were treated orally with a single dose of escalating herbal water, then caged and fed normally. orientative
acute toxicity (LDso) was assessed 7 days after this treatment. This was generally higher than 6001R9/9. The compounds of the invention can be prepared in various dosage forms, for example in the form of oral tablets, capsules, sugar- or film-coated tablets, in the form of liquid baths or suspensions, in whole rectally, parenterally. The amount of drug that can be administered enterally, for example intramuscularly or by intravenous injection or infusion, depends on the age, weight, condition and route of administration of the patient. For example, dosages employed for oral administration to adults may range from about 10 to about 100 mg per dose, 1 to 5 times per day. The present invention encompasses drug Ff4m formulations that include a compound of the present invention in combination with a pharmaceutically acceptable excipient (which may be a carrier or diluent). Pharmaceutical compositions containing the compounds of this invention are usually prepared according to conventional methods and administered in a pharmaceutically suitable form. For example, solid oral forms may contain the active compound together with diluents such as whey, textrose, saccharose, cellulose, corn starch or potato starch, lubricants such as silica, talc, stearic acid, magnesium or calcium stearate and/or polyethylene. glycol. Binders such as starch, gum arabic, gelatin, methylcellulose, carboxymethylcellulose or polyvinylpyrrolidone, dispersants such as starch, alginic acid, alginate or sodium starch glyflate, boiling mixtures,
Said medicinal preparations may contain dyes, sweeteners, humectants 1, such as lecithin, porin rubate, lauryl sulfate, and generally non-toxic and pharmaceutically inert substances used in mulberry formulations. It can be manufactured in a manner such as by mixing, granulating, tabletting, sugar coating or film coating methods. Liquid dispersions for oral administration can be, for example, syrups, emulsions and suspensions. The syrup may contain, for example, sucrose or sucrose containing glycerin and/or mannitol and/or sorbitol as carrier. In particular, syrups to be administered to diabetic patients can contain as carrier only products that cannot be metabolized to glucose or can be metabolized only to very small amounts of glucose, such as sorbitol. Suspensions or emulsions may be prepared using carriers such as natural comb, agar, sodium alginate, /-? It may contain cutin, methylcellulose, carboxymethylcellulose or polyvinyl alcohol. Suspensions or baths for intramuscular injection contain the active compound together with a pharmaceutically acceptable carrier, such as sterile water. It may contain olive oil, ethyl oleate, glycols such as propylene glycol, and optionally a suitable base salt. Solutions for intravenous injection or infusion may contain as a carrier, for example sterile water. Alternatively, preferably it may be in the form of a sterile aqueous isotonic salt bath. The active compound may contain together with the active compound a pharmaceutically acceptable carrier such as cocoa butter, polyethylene glyfur, polyoxyethylene sorbitan fatty acid surfactant or lecithin. The following examples illustrate, but do not limit, the present invention. Example 1 5-Amino-1,5-diphenyl-pyrazole (52f, 28t
After cooling, the reaction mixture was diluted with ice water. Then, it was neutralized with 35*NaOH. The solution was extracted with ethyl acetate and the organic phase was then evaporated to dryness under vacuum. Crystallization from chloroform-isopropyl ether gives 2.5f of 1,2-diphenyl-5-methyl-IH,7H-hirazolo[1,5-a)pyrimidine-7
-on, m, p, 147-148°C, NMR (CDC1
3) δppm=2.37(s) (3H,CHs)-5
, 91 (ba) (IH, C-6 proton), 6.55 (
a) (ILC-3 proton), 7.40 (m) (10
H, phenyl proton) was obtained. The first order compound was prepared by interpolation processing. 5-Methyl-1-(2-methyl-phenyl)-2-phe-L-IH,7H-virazo' (:1.5-a)pyrimidin-7-one. 5-Methyl-1-(2-nitro-phenyl)-2-phenyl-IH,7H-virazo' [1,5-a) Pyrimidin-7-one. 1-(2-chloro-phenyl)-5-methyl-2-phenyl-IH17H-virazo'l: 1.5-a) pyrimidin-7-one, 1-(2,4-lichlorophenyl)-5 -Methyl-
2-Fe-ru 1H,7H-pyra7o(1,5-a)pyrimidin-7-one. 1-(2,5-dichloro-phenyl)-5-methyl-
2-7A-IH,7H-Pira7o [1,5-a]
Pyrimidin-7-one. 5-Methyl-2-phenyl-1-(2-)lifluoromethyl-phenyl)-1H,7H-pyrazolo(1,5-
a) Pyrimidin-7-one, 5-methyl-1-(5-methyl-phenyl)-2-phenyl-IH,7H-pyrazolo(1,5-a:l pyrimidin-7-one. 5-methyl-1 -(3-Nitro-phenyl)-2-phe=IH,7H-Virazo0 [1,5-a) Pyrimidin-7-one. 1-(4-Methoxy-phenyl)-5-methyl-2-phenyl-IH,7H-pyrazolo[L5-a]pyrimidin-7-one. 1-(2,6-dichloro-phenyl)-5-methyl-
2-phenyl-1H,7H-pyra7o lj ,5-a
) pyrimidin-7-one. 1-(3-Fluoro-phenyl)-5-methyl-2-phenyl-IH,7I(-pyra7O[1,5-a)pyrimidin-7-one. 5-Methyl-2-phenyl-1-(3-,)lifluoromethyl-phenyl)-1H,7H-hirazolo[1,5
-a]pyrimidin-7-one, m, p, 149-1
50℃ 5-methyl-1-

[4-Methyl-phenyl]-2-phenyl-II (, 7H-virazo Ij, 5-a) pyrimidin-7-one, 5-methyl-1-(4-nitrophenyl) + 2-
centre! =Rue IH,7H-Pyrazolo 1.5-a) Pyrimidin-7-one. 1-(4-chloro-phenyl)-5-methyl-2-phenyl-IH,7H-pyra7" [1,5-a)pyrimidin-7-one, 1-(6-chloro-phenyl)-5- Methyl-2-phenyl-IH, 7H-pyrazolo, 5-a]pyrimidine-
7-on. 1-(4-Fluoro-phenyl)-5-methyl-2-phenyl-IH,7H-pyrazolo[1+5-a]pyrimidin-7-one. 5-Methyl-2-phenyl-1-(4-)lifluoromethyl-phenyl)-1H,7H-pyrazolo[1,5-
a) Pyrimidin-7-one, 1-benzyl-5-methyl-2-phenyl-IH,7H-virazo[1,5-a
] Pyrimidin-7-one. 1-tert-butyl-5-methyl-2-phenyl-IH,7
H-pyrazolo[1,5-a]biviridin-7-one. 1,5-dimethyl-2-phenyl-IH, 7H-pyrazolo[L5-a]pyrimidin-7-one, 5-methyl-2
-Phenyl-1-(2-pyridyl)-1H,7H-virazo[1,5-a]pyrimidin-7-one. 5-Methyl-2-phenyl-1-(3-pyridik)
-1L71(-pyra70 [1,5-a]pyrimidine-
7-on. 2-(4-chloro-phenyl)-1-7er-5-methyl-IH,7H-pyra7O(1,5-a)pyrimidin-7-one. 2-(4-methoxy-phenyl)-1-phenyl-5-
Methyl-IH,7H-virazo' (L5-a]pyrimidin-7-one. 5-Methyl-1-7er-2-(S-viridik)
-1H,7H-pyra7' [L5-a]pyrimidine-7
-one, 1,2-bis-(3-chloro-phenyl)-5-methy3
- jH,7H-virazo” [1,5-a]pyrimidin-7-one. 1-(5-chloro-phenyl)-2-(4-methoxy-
Fer) ~5-methyl-IH,7H-pyrazolo, 5
-a] pyrimidin-7-one. Example 2 The following compound was prepared by following the procedure of Example 1 using the appropriate substituted acetoacetate. 1.2-diphenyl-5-)lifluoromethyl-iH,
7H-vilazoo [1,5-a]pyrimidin-7-one, m, p, 142-143°C 1.2-diphenyl-6-ethyl-5-methyl-IH,
7H-pyra7o [1,5-a]biviridin-7-one, C2-') 7 Engineering-2-5-methyl-6-broby-IH,7)]-pipyrano [1,5-a]pyrimidine-7- on. 1.2-diphenyl-6-isopropyl-5-methyl-
IH, 7H-pyrazolo[1,5-a)pyrimidine-7-
on, 5,6-dimethyl-1,2-diphenyl-IH, 7H-
Pyrazolo[1,5-a]pyrimidin-7-one, m-p
-178~180℃ 6-/Roro 1.2-'; Phenyl-5-Mef-Lu
LH,7H-pyrano I:l [1,5-a]pyrimidin-7-one, m-p, 208-21 D C1,2-
diphenyl-6-methoxy-5-methy#-IH,7H-
Pyrazo'[1n5-a]pyrimidin-7-one, 1,2-u phenyl-6-ethoxy5-methyl-IH
,7H-pyrano'[1,5-a]pyridin-7-one. C2-u phenyl-6-hydroxy-5-methyl-1H
,7H-pyrano[1,5-a]pyrimidin-7-one. 6-acetoxy-1,2-diphenyl-5-methyl-I
H,7H-pyrano[1,5-a]pyrimidine-7-
on. 1,2-diphenyl-6-inpropoquin-5-methyl-IH, 7H-pyrazolo[1,5-a]pyrimidine-7
-On. 1.2-diphenyl-5-methyl-6--1'ropoxy-IH,7H-pyrano [1,5-a) pyrimidin-7-one, 6-allyloxy-1,2-'; phenyl-5-/ f
RuIH,7H-pyrano[1,5-a]pyrimidin-7-one. 1.2-Diphenyl-5-ethyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one. 1.2-Diphenyl-5-propyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one, m, p. 120-122°C 1.2-diphenyl-5-inpropyl-IH,7H-
Pyrazolo[1,5-a]pyrimidin-7-one, 5-chloromethyl-1,2-diphenyl-IH, 7H-pyrazolo[1,5-4)pyrimidin-7-one, m, p. 138-140℃ 5-di/lolomethyl-1,2-diphenyl-IH,7H
-pyrazolo[1,5-a:l pyrimidin-7-one. 1.2-diphenyl-5-methoxymethyl-IH,7I
(-pyrano" [1+ 5-a) pyrimidin-7-one. 1,2-diphenyl-5-nitoxymethyl-1H,7H
-pyrano (1,5-a)pyrimidin-7-one. 5-jethoxymethyl-1,2-diphenyl-IH,7
H-pyrazolo[1z 5-a]pyrimidin-7-one. 1 *2-diphenyl-5-hydroxymethyl-IH
,7H-pyrano[1,5-a]pyrimidin-7-one. 5-acetoxymethyl-1,2-diphenyl-IH,7
) i-pyrano (1,5-a)pyrimidin-7-one. 1-(4-methyl-phenyl)-2-phenyl-5-trifluoromethyl-18,7H-pyrazolo(1,5-a
) pyrimidin-7-one. 1-(4-nitro-phenyl)-2-7er-5-trifluoromethyl-IH, 7H-pyrazolo[1,5-a
) pyrimidin-7-one. 1-(4-chloro-phenyl)-2-phenyl-5-trifluoromethyl-IH,7H-hirazolo(1,5-a
] Pyrimidin-7-one. 1-(5-chloro-phenyl)-2-phenyl-5-trifluoromethyl-1H,7H-pyrazolo[1,5-a
] Pyrimidin-7-one, 1-(4-fluoro-phenyl)-2-7er-5-trifluoromethyl-IH,
7H-Hirazolo[1,5-alpyrimidin-7-one. 2-phenyl-5-trifluoromethyl-1-(5-)
(lifluoromethyl-phenyl)-1H,7H-virazo [1+ 5-a]pyrimidin-7-one. 1.2-Bis-(3-chloro-phenyl)-5-trifluoromedyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one. 1-(3-chloro-phenyl)-2-phenyl-(4-
methoxy-phenyl)-5-trifluoromethyl #-1)
(,7H-pyrazoloCI +5-a)pyrimidine-7-
on, 6-chloro-5-methyl-1-(4-methyl-7ale)-2-phenyl-IH,7H-pyrazolo[1,5-a
) pyrimidin-7-one. 6-chloro-5-methyl-1-(4-nitro-phenyl)-2-phenyl-IH,7H-pyrazolo(1,5-a
) pyrimidin-7-one. 6-ChloD-1-(4-chloro-phenyl)-5-methyl-2-phenyl-IH,7H-pyrazolo[1,5-a
] Pyrimidin-7-one. 6-chloro-1-(5-chloro-phenyl)-5-methyl-2-phenyl-IH,7T(-pyrazoloC1,5-
alpyrimidin-7-one. 6-chloro-1-(4-fluoro-phenyl-5-methyl-2-phenyl-1)(,7I(-pyrazolo(1,
5-a) Pyrimidin-7-one. 6-chloro-5-methyl-2-phenyl-1-(3-)
IJ fluoromethyl-phenyl)-1H. 7H-Virazo”[1,5-a]pyrimidin-7-one. 6-chloro-1,2-bis-(3-chloro-phenyl)
-5-Methyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one. 6-chloro-1-(3-chloro-phenyl)-2-(4
-methoxy-phenyl)-5-methyl-IH,7H-pyrazoo[1,5-a]pyrimidin-7-one. 5.6-dimethyl-1-(4-methyl-phenyl)-2
-Fenik -IH,7H-pyra゛” [1*5-a
] Pyrimidin-7-one. 5.6-dimethyl-1-(4-nitro-phenyl)-2
-Phenyl-IH,7H-pyrazolo[1,5-a:]pyrimidin-7-one. 1-(4-chloro-phenyl)-5,6-dimethyl-2-phenyl-IB, 7H-virazo' Ll, 5-a]
Pyrimidin-7-one. 1-(3-chloro-phenyl)-5,6-dimethyl-2-phenyl-IH,7H-pyrazo' (1* 5-a
] Pyrimidin-7-one. 1-(4-fluoro-phenyl)-5,6-dimethyl-2-phenyl-E,7H-pyrazolo-[1,5-a)
Pyrimidin-7-one, 5,6-dimethyl-2-phenyl-1-(3-trifluoromethyl-phenyl)-1H,7H-hirazolo(1
,5-a) Pyrimidin-7-one, 1,2-bis-(3
-chloro-phenyl-5,6-dimethy#-IH,71(
-virazo*[1,5-a]pyrimidin-7-one. 1-(5-chloro-phenyl)-2-(4-methoxy-
phenyl) -5,6-cymethyl-IB, 7) T-pyrazolo(1,5-alpyrimidin-7-one, 6-medoxy5-methyl-1-(4-methyl-phenyl)-2-
Phenyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one, 6-medoxy5-methyl-1-(4
-nitrophenyl)-2-phenyl-IH,7H-pyrazolo[1,5-alpyrimidin-7-one, 1-(4
-chloro-phenyl)-6-medoxy5-methyl-2
-Phenyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one. 1-(3-chloro-phenyl)-6-medoxy5-methyl-2-phenyl-IH,7H-pyrazolo[1,5-
a] Pyrimidin-7-one. 1-(4-fluoro-phenyl)-6-medoxy 5
-Methyl-2-phenyl-1H,7H-pyrazolo[1,
5-a] pyrimidin-7-one. 6-medoxy5-methyl-2-phenyl-1-(5-
) IJ fluoromethyl-phenyl)-1H,7H-vilazo o [1,5”a]pyrimidin-7-one. 1.2-bis-(3-chloro-phenyl)-6-medoxy5-methyl-II ( ,7H-pyrazolo[1,5-a
] Pyrimidin-7-one. 1-(5-chloro-phenyl)-6-medoxy2-(
4-methoxyphenyl)-5-methyl-IB, 7H-pyrazolo, 5-alpyrimidin-7-one. Example 5 Improhyritene-N-(1,2-diphenyl-pyrazole-3) dissolved in diphenylneedle (30π/)
-yl)-amino-methylene malonate, m, p, 23
5-237°C (3f) was heated to reflux temperature for 8 minutes. After cooling, the solvent is distilled off under a vacuum, and the residue is used as eluent with ethyl acetate. Purified by flash chromatography. The purified product is crystallized from cH2cz2/isopropyl ether to give 1 of 0.99
．． 2-Schiffx 2#-1H,7H-pyrazoo [1,
5-a]pyrimidin-7-one was obtained. m, p, 1
46-148℃sNMR (CDCLs) δ ppm:
5.91 (d) (IH. C-6 proton), 6.52Ls) <1H, C-5 proton), 7.22 (m) (10H, phenyl proton)
tZss(d) (IH, C-5 proton). 1-(4-methyl-phenyl)-2-phenyl-IH,
7H-virazoo[1*5-']pyrimidin-7-one, 1-(4-nitro-phenyl)-2-phenyl-IH,
7H-pyrazoo[1,5-alpyrimidin-7-one. 1-(4-chloro-phel)-2-phenyl-IH,
7H-pyrazolo5-a]pyrimidin-7-one. 1-(3-chloro-phenyl)-2-pheny #-IH,
7H-Pyrazolo, 5-a) Pyrimidin-7-one. 1-(4-fluoro-phenyl)-2-phenyl-II
(,7B-pyrazo” (1,5-a)pyrimidine-7-
on. 2-Phenyl-1-(3-trifluoromethyl-phenyl)-1H,7H-pyrazoo[1,5-a]pyrimidin-7-one. 1-Phenyl-2-(6-pyridyl)-1H,7H-pyrazolo[1,5-a]pyrimidin-7-one. 2-phenyl-1-(2-pyridyl)-1H,7)1-
Pyrazolo(1,5-a)pyrimidin-7-one. 1.2-bis-(5-chloro-phenyl)-1H. 7H-virazo'[1#5-11)pyrimidin-7-one, and 1-methyl-2-phenyl-IH,7H-pyrazolo[1
,5-a]pyrimidin-7-one. Example 4 1,2-diphenyl-5-methyl-II (,7H-pyrazolo, 5-a)pyrimidin-7-one (14f) dissolved in benzene (5(ld)) for 2 hours at room temperature under stirring. , N-bromosuccinimide (0,95f). The precipitate was dissolved by adding chloroform and the solution was washed with water. Evaporated to dryness in vacuo and the residue was dissolved in chloroform/isopropyl alcohol. crystallization from 169 6-bromo1,2-diphenyl-5-methyl-IH,7H-pyrazo
-a:] gave pyrimidin-7-one. The following compounds were prepared by similar VC operation. 6-Bromo1,2-diphenyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one. 6-bromo-1,2-diphenyl-5-trifluoromethyl-IH,7H-virazo[1,5-a]pyrimidin-7-one, 6-bromo-5-methyl-1-(4-methyl-phenyl )-2-phenyl-IH,7H-pyrazolo[1,5-a
] Pyrimidin-7-one. 6-bromo5-methyl-1-(4-nitro-phenyl)-2-phenyl-IH,7H-pyrazolo[1,5-a
] Pyrimidin-7-one. 6-bromo 1-(4-chloro-phenyl)-5-methyl-2-7er-IH,7H-pyrazolo[1,5-a
] Pyrimidin-7-one. 6-Bromo-1-(5-chloro-phel)-5-methyl-2-phenyl-IH,7H-pyrazolo[1,5-a
) pyrimidin-7-one. 6-/'Romo1-(4-fluoro-phenyl)-5-
Methyl-2-phenyl-IH, 7) I-pyrazolo[1,
5-a] pyrimidin-7-one. 6-bromo-5-methyl-2-phenyl-1-(5-)
IJ fluoromethyl-phenyl) -1H. 7H-Pyrazolo[1,5-a]pyrimidin-7-one, 6-chloro-1,2-diphenyl-IH, 7H-pyrazolo[1,5-a]pyrimidin-7-one. 6-chloro-1 ,2-diphenyl-5-trifluoromethyl-IH,7H-pyrazo[1,5-a]pyrimidin-7-one, Example 5 5-methyl-1-(4-nitro-phenyl)-2-phenyl- IH, 7H-Virazo'(1# 5-a)pyrimidin-7-one (4t) was dissolved in 57ToHC1 (15m) and acetic acid (45m) for 2 hours at 60 °C under stirring for 8
It was reacted with nCt2, 2H20 (25t). After cooling, the precipitate was filtered and washed with water, and then suspended in 2N NaOH under stirring. The product is filtered, washed with water until neutral, and crystallized from chloroform-ethanol. 2.8t of 1-(4-amino-phenyl)-5-methyl-2-phenyl-IH,7H-pyrazolo[1,5-a]
Pyrimidin-7-one was obtained. The following compounds were produced by the same treatment. 1-(4-amino-phenyl)-2-phenyl-IH,
7H-pyrazoo[1+5-a)pyrimidin-7-one, 1-(4-amino-phenyl)-2-phenyl-5-trifluoromethyl-II(,7H-pyrazolo[1,5-
a] Pyrimidin-7-one. 1-(4-Amino-phenyl)-5,6-dimethyl-2-phenyl-IH,7)]-pipyrazolo 1.5-a)
Pyrimidin-7-one, 1-(4-amino-phenyl)-6-chloro-5-methyl-2-phenyl-IH,7H-pyrazoloi0S-a)
Pyrimidin-7-one, and 1-(4-minophenyl)-6-medoxy5-methyl-2-phenyl-I
H,7H-pyrazolo[1,5-a)pyrimidin-7-one, Example 6 5-chloromethyl-1,2-diphenyl-IH. 7H-Biran'(1,5-a]pyribadin-7-one. m, p, 138-14 DC (2,2f) in 2-butane y(150-) at reflux temperature at 16:5 3. Reacted with pyrrolidine (1 g).After cooling, the bath liquid was evaporated to dryness in vacuum, and the residue was purified on an 8102 column at a ratio of 97:3.
It was purified using a chloroform/methanol solution. The recovered product was converted to cn2. When crystallized from cz2-isopropyl ether. 1.62 of 1,2-diphenyl-5-(pyrrolidine-1
-yl-methyl) -1) 1.7H-pyrazolo[1,5
-3pyrimidin-7-one was obtained. By similar treatment, the following compound was prepared, 5-([1q-diethylamino-methyl)-1,2
-diphenyl-IH,7H-pyrazolo,5-a]pyrimidin-7-one, 1,2-diphenyl-5-(morpholino-methyl)-
1H,7H-bilane o [1,5-a)pyrimidine-7
-On. 5-(N,N-dimethylamino-methyl)-1,2-
Diphenyl-1H,7H-bilane o [1,5-11:
] Pyrimidin-7-one. 1.2-Schiff, xnyl-5-(thiomorpholino-methy/
) -1H,7H-Biran O[1,sa]pyrimidin-7-one. 5-(N-i, soprobylaminomethyl)-1,2-
Diphenyl-IH,7H-Birano (1,5-a)pyrimidin-7-one. 1,2-Diphenyl-5-(imidazol-1-yl-methyk)-1H,7H-pyrazolo[1*5-a ]pyrimidin-7-one, 5-(N-tert-butylamino-methyl)-1,2-diphenyl-1H,7H-bilan' [1,5-a]pyrimidin-7-one, 1,2-diphenyl -5-(Hisuridinomethyl) -
1H,7H-bilane” [1,5-a]pyrimidine-7
-On. 5-(hexahydro-1H-azepin-1-yl-methyl)-L2-:) phenyl-1) 1.7)(-pyrazolo[1,5-a3pyrimidin-7-one. 1.2-diphenyl-5 -C(4-methyl-piperazin-1-yl)-methyl]-1n, 7■+-pyrazolo[1
,5-a]pyrimidin-7-one. Example 7 l-(4-amino-phenyl)-5-methyl-2-phenyl-1H,7H-bilane o [1,5-a]pyrimidin-7-one (2t) was added to 37 kHCl(5-) After cooling, the precipitate was filtered and washed with acetic acid and then with water to give 1.9 F of 1-(4-amino-phenyl). −
5-Methyl-2-phenyl-IH,7H-bilane o [
j, 5-a] pyrimidine-7-one hydrochloride m-p, >3
50°C was obtained. The following compound was produced by the same operation. 1-(4-minophenyl)-2-phenyl-IH,
7) 1-pyrazolo(1,5-a:l pyrimidin-7-one Hanasuka and 1-(4-amino-phenyl)-2-phenyl-5-trifluoromethyl-IH,7H-pyrazolo(1, 5-a
] Pyrimidin-7-one. Example 8 Tablets each weighing 7511 g and containing 25 sy of active substance were prepared as follows. Composition (for 10,000 tablets) 1,2-diphenyl-5-methyl-IH,7H-pyrazolo (1,5-a
) Pyrimidin-7-one 250 lactose 655t Corn starch 120f Talc powder 17.5 ? Magnesium stearate 7.5 fl, 2-diphenyl-5-methyl-IH,7H-pyrazolo[1,5-a
] The pyrimidin-7-one, lactose and half the corn starch are mixed together. The mixture is then forced through a sieve having a 0.5 inch opening. Corn starch (10
f) is suspended in warm water (100 m). The resulting paste is used to granulate the powder. The granules were dried and micronized on a 14M sieve size sieve, then the remaining amount of starch, Merck and magnesium stearate were added, mixed carefully, and tableted using a 6II11 diameter punch. Process it into Patent applicant: Firmitalia Calguchi Elba Societa Bel Azzio and two others Continuation of 1st page ■Int, CI,' Identification symbol Office board A 61 K
31154 AAF 66e@ Inventor Calguchi Patusarotzte Italy [I

Claims (1)

[Claims] 1) General formula [in the formula. R1 is a) C1-C,5 alkyl or benzyl. b) Pyridyl, unsubstituted or substituted with 01-c6 alkyl. C) Unsubstituted or halogen, trihalomethyl, C
l-06 alkyl, 01-6 alkyl, hydroxy,
Formyloxy, C2-c6 alkanoyloxy. phenyl substituted with one or more substituents selected from nitro, amine, formylamino and C26alkanoylamino. R2 is a) pyridyl or b) unsubstituted or halogen, trihalomethyl, nitro, c 1-c 6 alkoxy and c 1-c 6
phenyl substituted with one or more substituents selected from alkyl; 69°R5 is hydrogen or unsubstituted % or halogen; Hydroxy, C1-06 alkoxy, formyloxy,
02~C6 Alkanoyloxy may independently be hydrogen, auto~
C6 alkyl, phenyl or benzyl or R5 and R6 taken together with the nitrogen atom to which they are attached, N-imidazolyl, hexahydro-N-acevinyl, N-pyrrolidinyl, N-piperazinyl, bilysine; 01-C6 alkyl substituted with one or more h substituents selected from thiomorpholino and morpholino, forming an unsubstituted or substituted 01-C6 alkyl heterocycle; , R4 is hydrogen, halogen, -C6 alkyl, hydroxy, 01-C6 alkoxy, c5-c4 alkenoyloxy, formyloxy or c2-c6 alkanoyloxy] and its pharmaceutically acceptable compounds. Urushio. 2) R1 is aI) -C4 alkyl or benzyl, b
/) Unsubstituted or methyl-substituted pyridyl, C-unsubstituted or halogen, trifluoromethyl, 01-
C4 alkyl, cl-c4 alkoxy, nitro, amino, formylamino and phenyl substituted with one or two substituents selected from 02-C6 alkanoylamino, R2 is unsubstituted, chlorine, fluorine, trifluoromethyl, nitro, phenyl substituted with one or two substituents selected from 01-C4 alkyl and self-C4 alkoxy, R3 is hydrogen or unsubstituted,
or chlorine, fluorine, hydroxy, auto-C4 alkoxy,
formyloxy, C2-C6 alkanoyloxy and dihydrogen, 01-C4 alkyl, or phenylte or R5 and R6 together with the nitrogen atom to which they are attached, N-imidazolyl, hexahydro-N-azepinyl, N-pyrrolidinyl, N-piperazinyl, piperidino. -C substituted with 1 to 3 substituents selected from thiomorpholino and morpholino (forming an unsubstituted heterocycle or substituted with 01-C3 alkyl)
4 alkyl, R4 is water X, eight hegen, C1-C
4 alkyl, hydroxy, cl-c4 alkoxy IC3
-C4 alkenyloxy, or C2-C6 alkanoyloxy, the formula (1
) and pharmaceutically acceptable salts thereof. 3) R1-C4 alkyl, benzyl or pyridyl, f) unsubstituted or chlorine, fluorine, trifluoromethyl, methyl, auto-c2 alkoxy, nitro, amine, formylamino, and C2-C4 alkanoylamino phenyl substituted with one or two substituents selected from R2 is unsubstituted or halogen, trifluoromethyl,
Nitro, phenyl substituted with one or two substituents selected from 01-C4 alkyl and 01-C4 alkoxy, and R3 is hydrogen, unsubstituted or halogen. hydroxy, cl-c2 alkoxy, formyloxy IC2-C4 alkanoyloxy and the radical hydrogen, or 01-C4 alkyl or R5 and R6 taken together with the nitrogen atom to which they are attached, unsubstituted N-
imidazolyl, unsubstituted hexahydro-N-azepinyl, unsubstituted N-pyrrolidinyl, unsubstituted or 01-C
3-alkyl-substituted N-piperazinyl, unsubstituted or methyl-substituted piperidino and morpholino, and unsubstituted thiomorpholino to form selected heterocycles)
01-C4 alkyl substituted with 1 to 3 substituents selected from Ra hydrogen b halogen, C1-C6 alkyl, hydroxy, cl-c3 alkoxy, allyloxy. or C2-04 alkanoyloxy, and a pharmaceutically acceptable compound thereof according to the formula (1) according to claim 1. 4) 1,2-diphenyl-5-methyl-IH,7H-
Pyrazolo[1ts-a]pyrimidin-7-one. 1.2-diphenyl-5-trifluoromethyl-IH,
7H-bilane D (1,5-alpyrimidin-7-one, 1,2-diphenyl-IH,7B-pyrazolo[1,5-
a] Pyrimidin-7-one, 5-methyl-1-(4-methyl-phenyl)-2-phenyl-IH,7H-bilane o [1,5-a]pyrimidin-7-one, 5-methyl-1 -(4-nitro-phenyl)-2-phenyl-1)(,7H-bilane' C1C5-a)pyrimidin-7-one, 1-(4-chloro-phenyl)-5-methyl-2-7x
=h -IH,7H-pyrazolo[1,5-a]pyrimidin-7-one, 1-(6-chloro-phenyl)-5-methyl-2-phx
=Rue IH,7H-pyrazolo[1,5-a]pyrimidin-7-one, 1-(4-fluoro-phenyl)-5-methyl-2-phenyl-IH,7H-pyrazolo[1,5-a] Pyrimidin-7-one. 5-Methyl-2-phenyl-1-(!l-)lifluoromethyl-phenyl)-1H,7E-hirazolo[1,
5-a]pyrimidin-7-one, 1-benzyl-5-methyl-2-phenyl-IH,7H-pyrazolo[1,5-
a) Pyrimidin-7-one. 1-tert-butyl-5-methyl-2-phenyl-IH17
H-bilane o [1,5-a,]pyrimidin-7-one. 1,5-dimethyl-2-phenyl-IH,7H-pyrazolo[1,5-a]pyrimidin-7-one, 5-meth-2-phenyl-1-(2-pyridyl)-1H,7H
-Biran o [1,5-a,]pyrimidin-7-one. 5-methyl-2-phenyl-1-[6-pyridyl) -
1H,7H-bilane 0 [1,5-a]pyrimidine-7
-one, 1,2-bis(6-chloro-phenyl)-5-methy/L
/ -I B + 7) (-bilane O[C5-a)pyrimidin-7-one, 1-(6-chloro-phenyl)-2-(4-methoxy-
phenyl)-5-methyl-IH,7H-pyrazolo[1,
5-a) Pyrimidin-7-one. 1.2-diphenyl-5+6-:)methyl-IH,7H
-pyrazolo[1,5-a]pyrimidin-7-one. 6-ri p-1,2-diphenyl-5-methyl-IH,
7H-pyrazolo[1,5-a]pyrimidin-7-one. 1.2-diphenyl-6-medoxy5-methyl-IH
,7H-bilane o C1,5-alpyrimidin-7-one, 1,2-diphenyl-6-ethoxy5-methyl-IH
,7H-bilane o (1,5-a)pyrimidin-7-one, 5- (N,N-diethylamino-methyl)-1,2-
Diphenyl-IH, 7B-pyrazolo[1,5-a]pyrimidin-7-one. 1.2-Diphenyl-5-(pyrrolidin-1-yl-methyl)-1H,7H-bilane O[1,s-a]pyrimidin-7-one. 1.2-diphenyl-5-(imidazol-1-yl-
methyl) -1H,7H-pyrazolo[1,5-a]pyrimidin-7-one. 1.2-diphenyl-5-methoxymethyl-IH,7H
- A compound selected from the group consisting of bi2zo[1,5-a]pyrimidin-7-one and pharmaceutically acceptable salts thereof. 5) a) The following formula (n) (wherein R1, R2, R5 and R4 are as defined in Claim 1 above, and R7 is a compound of formula (II) during ring closure) is a new nuclear group which can be cleaved from the carbon atom to which it is bonded, or a salt thereof; b) ring-closing a compound of the following formula (II) (wherein R1 and R2 are within the scope of the above claims); As defined in Section 1, and R8 is hydrogen or unsubstituted 01-C
6 alkyl) to produce a compound of formula 0) where R4 is hydrogen or unsubstituted 01-C6 alkyl and R4 is hydrogen, or C) (IV) (wherein R1 and R2 are as defined in claim 1 above, and R is as defined above, and each of R9 and RIG is independently Cj
R3 is hydrogen or unsubstituted 01-C6 alkyl, and R4
is hydrogen, and optionally converting the compound of formula (1) to other compounds of formula (1) and/or optionally converting the compound of formula (1) to other compounds of formula (1). converting the compound into its pharmaceutically acceptable salt and/or optionally from that salt to the formula (
1), forming the free compound and/or optionally separating the isomer mixture into single isomers. 6) a method for producing a compound of formula (1) and a pharmaceutically acceptable substance thereof as claimed in claim 1; 6) a suitable carrier and/or diluent and as an active ingredient A pharmaceutical composition containing the compound of formula (1) according to claim 1 or a pharmaceutically acceptable salt thereof. -7) A compound of formula (1) as defined in claim 1 described herein other than the compound or group described in claim 4 or a pharmaceutically acceptable salt thereof. 8) A compound of formula (R) or a pharmaceutically acceptable salt thereof as defined in claim 1 for use in a method of therapeutic treatment of a human or extended animal body. 9) Central nervous system. A compound of formula (1) or a salt thereof according to claim 8 for use as a sedative. 10) Substantially described in any one of statements 1 to 6 herein. A method for producing a compound of formula (1) as defined in claim 1. 11) A process for producing a pharmaceutically acceptable salt of a compound of formula (1) as defined in Claim 1 Jji substantially as described in Example 7 herein. 12) A pharmaceutical composition substantially as described in Example 8 herein.