CS250688B2 - Method of pyridazine's derivatives production substituted in position 3 by substituted aminogroup - Google Patents
Method of pyridazine's derivatives production substituted in position 3 by substituted aminogroup Download PDFInfo
- Publication number
- CS250688B2 CS250688B2 CS854090A CS409085A CS250688B2 CS 250688 B2 CS250688 B2 CS 250688B2 CS 854090 A CS854090 A CS 854090A CS 409085 A CS409085 A CS 409085A CS 250688 B2 CS250688 B2 CS 250688B2
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- Czechoslovakia
- Prior art keywords
- formula
- alk
- alkyl
- phenyl
- defined above
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000004892 pyridazines Chemical class 0.000 title description 3
- 125000003277 amino group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical class ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- -1 3- (3-ethoxycarbonylpropylamino) -4-methyl-6-phenylpyridazine hydrochloride Chemical compound 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 229910017849 NH2—NH2 Inorganic materials 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 1
- 206010003549 asthenia Diseases 0.000 claims 1
- 230000003542 behavioural effect Effects 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 230000001079 digestive effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 206010022437 insomnia Diseases 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000003340 mental effect Effects 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 230000003236 psychic effect Effects 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Vynález se týká způsobu výroby derivátů pyridazinu substituovaných v poloze 3 karboxamidoalkylaminoskupinou, jakož i jejich adičních solí s kyselinami.BACKGROUND OF THE INVENTION The present invention relates to a process for the preparation of carboxamidoalkylamino group-substituted pyridazine derivatives as well as their acid addition salts.
Tyto sloučeniny se vyznačují účinky na centrální nervovou soustavu a lze jich proto použít jako účinné složky ve farmaceutických prostředcích.These compounds have central nervous system effects and can therefore be used as active ingredients in pharmaceutical compositions.
Sloučeniny vyrobené způsobem podle vynálezu je možno znázornit obecným vzorcem IThe compounds of the present invention can be represented by Formula I
Ri —y“ NH - Atk V-ÍV ve kterém váný halogenem, naftylový zbytek, cyklohexylový zbytek, thien-2-ylový zbytek nebo thien-2-ylový zbytek,R 1 -y "NH-Atk V-IV in which halogenated, naphthyl, cyclohexyl, thien-2-yl or thien-2-yl,
R2 znamená vodík, alkylovou skupinu s 1 až 4 atomy uhlíku nebo fenylový zbytek,R 2 is hydrogen, C 1 -C 4 alkyl or phenyl,
R3 znamená vodík, alkylovou skupinu s 1 až 4 atomy uhlíku, fenylový zbytek nebo kyanoskupinu,R3 is hydrogen, (C1-C4) alkyl, phenyl or cyano,
R4 znamená skupinu —CONH2, aR4 represents a group —CONH2, and
Alk znamená skupinu (CH2)n, kde n znamená celé číslo 2, 3 nebo 4.Alk is (CH 2) n wherein n is an integer of 2, 3 or 4.
Sloučeniny obecného vzorce I skýtají s minerálními nebo organickými kyselinami adiční soli. Do rámce vynálezu spadá rovněž příprava adičních solí sloučenin obecného vzorce I s farmaceuticky vhodnými kyselinami.The compounds of formula I provide addition salts with mineral or organic acids. It is also within the scope of the invention to prepare addition salts of compounds of formula I with pharmaceutically acceptable acids.
Způsob podle vynálezu k výrobě sloučenin obecného vzorce I spočívá v tom, že se příslušně substituovaný 3-chlorpyridazin 0becného vzorce IIThe process according to the invention for the preparation of the compounds of the general formula I is characterized in that the correspondingly substituted 3-chloropyridazine of the general formula II
Ri znamená vodík, alkylovou skupinu s 1 až 4 atomy uhlíku, fenylový zbytek, fenylový zbytek monosubstituovaný halogenem nebo nitroskupinou nebo alkylovou skupinou s 1 až 4 atomy uhlíku nebo alkoxyskupinou s 1 až 4 atomy uhlíku nebo hydroxylovou skupinou, fenylový zbytek disubstituoRi-\' N-N lil)R 1 is hydrogen, C 1 -C 4 alkyl, phenyl, phenyl monosubstituted with halogen or nitro or C 1 -C 4 alkyl or C 1 -C 4 alkoxy or hydroxyl, disubstituted R 1 -NN phenyl lil)
230688 ve kterém230688 in which
Ri, R2 a R3 mají výše uvedený význam, nechá reagovat s nadbytkem hydrátu hydrazinu NH2—NH2, vzniklý hydrazinoderivát obecného vzorce III se nechá; reagovat .*s ω-halogenovanou sloučeninou Obécného vzorce VR1, R2 and R3 are as defined above, reacted with an excess of hydrazine hydrate NH2-NH2, and the resulting hydrazino derivative of formula (III) is left ; with a ω-halogenated compound of Formula V
X—Alk—R4‘ (V) ve kterémX — Alk — R4 ‘(V) in which
X znamená halogen, s výhodou brom, R4l znamená skupinu COO-alkyl s 1 až 4 atomy uhlíku v alkylové části a Alk má výše uvedený význam, a vzniklý ester obecného vzorce Γ ve kterémX is halogen, preferably bromine, R < 4 > is C1-C4 alkyl in the alkyl moiety, and Alk is as defined above, and the resulting ester of formula (I) in which:
Ri, R2 ia R3 mají výše uvedený význam, se katalyticky hydrogenuje, vzniklý aminoderivát obecného vzorce IVR1, R2 and R3 are as defined above, the resulting amino derivative of formula IV is catalytically hydrogenated
Nl i^Nl i ^
N-N (IVI ve kterémN-N (IVI in which
Ri, R2 a R3 mají výše uvedený význam, Rr^\ //-NR-AU-RJR 1, R 2 and R 3 are as defined above ;
N~Ň (/'} ve kterémN ~ Ň (/ '} in which
Rl, R2, R3, Rá‘ a Alk mají výše uvedený význam, se působením amoniaku převede ve sloučeninu obecného vzorce I, ve kterém Ri, R2, R3, R4 a Alk mají význam uvedený pod obecným vzorce I, načež se získaná sloučenina obecného vzorce I popřípadě přemění ve svou adiční sůl s kyselinou.R 1, R 2, R 3, R a 'and Alk are as defined above, converted by ammonia treatment to a compound of formula I wherein R 1, R 2, R 3, R 4 and Alk are as defined under formula I, then the compound of formula I obtained If desired, it is converted into its acid addition salt.
Postup podle vynálezu je možno znázornit reakčním schématem:The process of the invention can be illustrated by the following reaction scheme:
(II 1(II 1
,r, r
Aík-fí, ' h (VI y-NH-AI-h- R,' —ϊ N~n ((') (R4‘ — COO-alkyl s 1 až 4 atomy uhlíku v alkylové části)Al-phi, h (VI-NH-Al-h-R, '- N - n ((') (R 4 - COO alkyl of 1 to 4 carbon atoms in the alkyl moiety)
R, R3 nh3 R, R 3, nh 3
->· Rr\\ NH-Mk ~ CONH?-> · R r \\ NH- MK ~ CONH?
N-N (IIN-N (II
Jako výchozí látky se použije pyridazinu obecného vzorce II, chlorovaného v poloze 3, který se přemění v příslušný 3-amínoderivát obecného vzorce IV. Poněvadž při praktickém provádění je přímá cesta k získání aminoderivátu spojena s obtížemi, postupuje se přes hydrazinovaný meziprodukt obecného vzorce III, který se získá v dobrém výtěžku varem chlorovaného pyridazinu obecného vzorce II pod zpětným chladičem s nadbytkem hydrazinhydrátu. Z hydrazinovaného derivátu obecného vzorce III se hydrogenací v přítomnosti katalyzátoru, jako je například Raneyův nikl, připraví aminoderivát obecného, vzorce IV,The starting material used is a pyridazine of the formula II, chlorinated in the 3-position, which is converted to the corresponding 3-amino derivative of the formula IV. Since in practice the direct route to obtain the amino derivative is difficult, the hydrazinated intermediate of formula III is obtained, which is obtained in good yield by refluxing the chlorinated pyridazine of formula II with an excess of hydrazine hydrate. From the hydrazinated derivative of formula (III), an amino derivative of formula (IV) is prepared by hydrogenation in the presence of a catalyst such as Raney nickel,
Působením ω-halogenovaného esteru obecného vzorce V na aminoderivát obecného vzorce IV se získá sloučenina obecného vzorce Γ. Reakce se provádí zahříváním reakčních složek v prostředí rozpouštědla, nanapříklad dimethylformamidu, při teplotě 50 až 100 °C.Treatment of the amino derivative of formula IV with a ω-halogenated ester of formula V yields a compound of formula Γ. The reaction is carried out by heating the reactants in a solvent medium such as dimethylformamide at a temperature of 50 to 100 ° C.
Sloučeniny obecného vzorce I, ve kterém R4 znamenají skupinu —CONH.2, se získají ze sloučenin obecného vzorce Γ, ve kterém R41 znamená skupinu -COO-alkyl s 1 až 4 atomy uhlíku v alkylové části, působením amoniaku, rozpuštěného v alifatickém alkoholu, například methanolu.Compounds of formula (I) in which R 4 is -CONH 2 are obtained from compounds of formula (Γ) in which R 4 is -COO-alkyl of 1 to 4 carbon atoms in the alkyl moiety by treatment with ammonia dissolved in an aliphatic alcohol such as methanol.
3-Chlorpyridaziny, použité jako výchozí látky, jsou známé sloučeniny nebo je lze připravit známými postupy, zejména působením nadbytku oxychloridu fosforečného na příslušné 2H-pyridaz-3-ony.The 3-chloropyridazines used as starting materials are known compounds or can be prepared by known methods, in particular by treating excess 2H-pyridaz-3-ones with an excess of phosphorus oxychloride.
Vynález je blíže objasněn dále uvedenými příklady provedení.The invention is illustrated by the following examples.
Příklad 1.Example 1.
3- (3-Karboxyamidopropylamino j -6- (4-chlor f enyl) -pyr idazin obecného vzorce I, ve kterém3- (3-Carboxyamidopropylamino) -6- (4-chlorophenyl) -pyridazine of formula I, wherein:
R2=R3 = H, Alk = (CH2)3, R4 = CONH2R 2 = R 3 = H, Alk = (CH 2) 3, R 4 = CONH 2
1,3 g 3-{3-ethoxykarbonylpropylamino)-6-(4-chlorfenyl)-pyridazinu se rozpustí ve 100 ml methanolu. Ve vzniklém roztoku, který se ochladí v ledové lázni, se rozpustí 13 gramů amoniaku. Reakční směs se míchá 6 dnů při teplotě místnosti, načež se odpaří do sucha za sníženého tlaku. Po překrystalování zbytku z acetonitrilu se získá 0,7 g v záhlaví uvedené sloučeniny o teplotě tání 180 °C.1.3 g of 3- (3-ethoxycarbonylpropylamino) -6- (4-chlorophenyl) pyridazine are dissolved in 100 ml of methanol. 13 grams of ammonia are dissolved in the resulting solution, which is cooled in an ice bath. The reaction mixture was stirred at room temperature for 6 days and then evaporated to dryness under reduced pressure. After recrystallization of the residue from acetonitrile, 0.7 g of the title compound of melting point 180 DEG C. is obtained.
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS854090A CS250688B2 (en) | 1984-01-27 | 1985-06-07 | Method of pyridazine's derivatives production substituted in position 3 by substituted aminogroup |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS84613A CS245789B2 (en) | 1984-01-27 | 1984-01-27 | Production method of pyridazine substituted derivatives in position 3 by substituted amino group |
CS854090A CS250688B2 (en) | 1984-01-27 | 1985-06-07 | Method of pyridazine's derivatives production substituted in position 3 by substituted aminogroup |
Publications (1)
Publication Number | Publication Date |
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CS250688B2 true CS250688B2 (en) | 1987-05-14 |
Family
ID=5338545
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS84613A CS245789B2 (en) | 1983-01-27 | 1984-01-27 | Production method of pyridazine substituted derivatives in position 3 by substituted amino group |
CS854090A CS250688B2 (en) | 1984-01-27 | 1985-06-07 | Method of pyridazine's derivatives production substituted in position 3 by substituted aminogroup |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS84613A CS245789B2 (en) | 1983-01-27 | 1984-01-27 | Production method of pyridazine substituted derivatives in position 3 by substituted amino group |
Country Status (1)
Country | Link |
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CS (2) | CS245789B2 (en) |
-
1984
- 1984-01-27 CS CS84613A patent/CS245789B2/en unknown
-
1985
- 1985-06-07 CS CS854090A patent/CS250688B2/en unknown
Also Published As
Publication number | Publication date |
---|---|
CS245789B2 (en) | 1986-10-16 |
CS61384A2 (en) | 1985-06-13 |
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