CS217964B2 - Method of making the 3-/1-pyrazolyle-/paridazin derivatives - Google Patents

Method of making the 3-/1-pyrazolyle-/paridazin derivatives Download PDF

Info

Publication number: CS217964B2
Authority: CS; Czechoslovakia
Prior art keywords: pyridazine; pyrazolyl; group; alkyl; hydroxyalkyl
Prior art date: 1977-10-25

Application number

CS784648A

Other languages

Czech (cs)

English (en)

Inventor

Geza Szilagyi

Endre Kasztreiner

Laszlo Tardos

Edit Kosa

Laszlo Jaszlits

Gyoergy Cseh

Szabo Ilona Kovacs

Pal Tolnay

Sandor Elek

Istvan Elekes

Istvan Polgari

Original Assignee

Richter Gedeon Vegyeszet

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-10-25

Filing date

1978-07-11

Publication date

1983-02-25

1978-07-11 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1980-01-18 Priority to CS80370A priority Critical patent/CS217965B2/cs

1983-02-25 Publication of CS217964B2 publication Critical patent/CS217964B2/cs

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 69
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims description 24
238000000034 method Methods 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 8
239000012458 free base Substances 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
SKXBTBMQHHPISZ-UHFFFAOYSA-N 3-pyrazol-1-ylpyridazine Chemical class C1=CC=NN1C1=CC=CN=N1 SKXBTBMQHHPISZ-UHFFFAOYSA-N 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 abstract description 11
239000001257 hydrogen Substances 0.000 abstract description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 11
239000000460 chlorine Substances 0.000 abstract description 9
229910052801 chlorine Inorganic materials 0.000 abstract description 9
125000000217 alkyl group Chemical group 0.000 abstract description 7
125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 7
150000003180 prostaglandins Chemical class 0.000 abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
230000001077 hypotensive effect Effects 0.000 abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 3
108090000790 Enzymes Proteins 0.000 abstract description 3
102000004190 Enzymes Human genes 0.000 abstract description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
230000015556 catabolic process Effects 0.000 abstract description 2
125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 2
230000001105 regulatory effect Effects 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
125000004093 cyano group Chemical group *C#N 0.000 abstract 1
229910052731 fluorine Inorganic materials 0.000 abstract 1
239000011737 fluorine Substances 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
230000000144 pharmacologic effect Effects 0.000 abstract 1
125000004193 piperazinyl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
239000000203 mixture Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000007858 starting material Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
-1 aliphatic alcohols Chemical class 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
239000002904 solvent Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
OVXSFTFBSBIDMM-UHFFFAOYSA-N 3-chloro-6-(3,5-dimethylpyrazol-1-yl)pyridazine Chemical compound N1=C(C)C=C(C)N1C1=CC=C(Cl)N=N1 OVXSFTFBSBIDMM-UHFFFAOYSA-N 0.000 description 5
229960002474 hydralazine Drugs 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
FXYQRYGWWZKUFV-UHFFFAOYSA-N (6-chloropyridazin-3-yl)hydrazine Chemical compound NNC1=CC=C(Cl)N=N1 FXYQRYGWWZKUFV-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000013078 crystal Substances 0.000 description 4
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 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 description 3
101710088194 Dehydrogenase Proteins 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
210000003734 kidney Anatomy 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
ZQSOSVVIIRGJQV-UHFFFAOYSA-N 1-(6-chloropyridazin-3-yl)-3,5-dimethylpyrazol-4-amine Chemical compound CC1=C(N)C(C)=NN1C1=CC=C(Cl)N=N1 ZQSOSVVIIRGJQV-UHFFFAOYSA-N 0.000 description 2
CMGRDLNEHMAXLW-UHFFFAOYSA-N 3-(4-bromo-3,5-dimethylpyrazol-1-yl)-6-chloropyridazine Chemical compound CC1=C(Br)C(C)=NN1C1=CC=C(Cl)N=N1 CMGRDLNEHMAXLW-UHFFFAOYSA-N 0.000 description 2
PVVBIZIQXSFHBE-UHFFFAOYSA-N 3-chloro-6-(3,5-diethylpyrazol-1-yl)pyridazine Chemical compound N1=C(CC)C=C(CC)N1C1=CC=C(Cl)N=N1 PVVBIZIQXSFHBE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
102000004195 Isomerases Human genes 0.000 description 2
108090000769 Isomerases Proteins 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
210000004204 blood vessel Anatomy 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000005191 hydroxyalkylamino group Chemical group 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
206010038464 renal hypertension Diseases 0.000 description 2
BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 description 1
GJNSELBGDLLJPP-UHFFFAOYSA-N (6-pyrazol-1-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1N1N=CC=C1 GJNSELBGDLLJPP-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
QSEFTOYPSHMMDG-UHFFFAOYSA-N 1,3-dicyclopropylpropane-1,3-dione Chemical compound C1CC1C(=O)CC(=O)C1CC1 QSEFTOYPSHMMDG-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DOJSQOIVZKGPED-UHFFFAOYSA-N 1-(6-hydrazinylpyridazin-3-yl)-3,5-dimethylpyrazol-4-amine Chemical compound CC1=C(N)C(C)=NN1C1=CC=C(NN)N=N1 DOJSQOIVZKGPED-UHFFFAOYSA-N 0.000 description 1
GLEZUMPZSBSIJX-UHFFFAOYSA-N 2-(6-chloropyridazin-3-yl)-5-methyl-1h-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1C1=CC=C(Cl)N=N1 GLEZUMPZSBSIJX-UHFFFAOYSA-N 0.000 description 1
XKVWBZNDARWWSH-UHFFFAOYSA-N 2-(6-chloropyridazin-3-yl)-5-methylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=C(Cl)N=N1 XKVWBZNDARWWSH-UHFFFAOYSA-N 0.000 description 1
IFCHLGIEYFIHJN-UHFFFAOYSA-N 2-(6-hydrazinylpyridazin-3-yl)-5-methylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=C(NN)N=N1 IFCHLGIEYFIHJN-UHFFFAOYSA-N 0.000 description 1
MZGGKYQMFPBFBB-UHFFFAOYSA-N 2-(6-hydrazinylpyridazin-3-yl)pyrazol-3-amine Chemical compound N1=NC(NN)=CC=C1N1C(N)=CC=N1 MZGGKYQMFPBFBB-UHFFFAOYSA-N 0.000 description 1
XCWAYHHNGXJBOY-UHFFFAOYSA-N 2-[1-(6-chloropyridazin-3-yl)-3,5-dimethylpyrazol-4-yl]isoindole-1,3-dione Chemical compound CC1=C(N2C(C3=CC=CC=C3C2=O)=O)C(C)=NN1C1=CC=C(Cl)N=N1 XCWAYHHNGXJBOY-UHFFFAOYSA-N 0.000 description 1
LJEYARRIFIKDLQ-UHFFFAOYSA-N 2-[2-[6-(3,5-dimethylpyrazol-1-yl)pyridazin-3-yl]hydrazinyl]ethanol Chemical compound N1=C(C)C=C(C)N1C1=CC=C(NNCCO)N=N1 LJEYARRIFIKDLQ-UHFFFAOYSA-N 0.000 description 1
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QSWNDQWMSOPDHX-UHFFFAOYSA-N 3-chloro-6-(3,5-dicyclopropylpyrazol-1-yl)pyridazine Chemical compound N1=NC(Cl)=CC=C1N1C(C2CC2)=CC(C2CC2)=N1 QSWNDQWMSOPDHX-UHFFFAOYSA-N 0.000 description 1
GNUUNLBHINZXTC-UHFFFAOYSA-N 3-chloro-6-(3,5-dimethyl-1H-pyrazol-4-yl)pyridazine Chemical compound ClC=1N=NC(=CC=1)C=1C(=NNC=1C)C GNUUNLBHINZXTC-UHFFFAOYSA-N 0.000 description 1
OUOOTLVDZIAQNB-UHFFFAOYSA-N 3-chloro-6-(3,5-dimethyl-4-nitropyrazol-1-yl)pyridazine Chemical compound CC1=C([N+]([O-])=O)C(C)=NN1C1=CC=C(Cl)N=N1 OUOOTLVDZIAQNB-UHFFFAOYSA-N 0.000 description 1
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UHJKSQWERGVUAI-UHFFFAOYSA-N 3-chloro-6-(3,5-diphenylpyrazol-1-yl)pyridazine Chemical compound N1=NC(Cl)=CC=C1N1C(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=N1 UHJKSQWERGVUAI-UHFFFAOYSA-N 0.000 description 1
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DZVYUWZLETYXKE-UHFFFAOYSA-N [6-(4-chloro-3,5-dimethylpyrazol-1-yl)pyridazin-3-yl]hydrazine Chemical compound CC1=C(Cl)C(C)=NN1C1=CC=C(NN)N=N1 DZVYUWZLETYXKE-UHFFFAOYSA-N 0.000 description 1
XOFBYGYMCBLZBB-UHFFFAOYSA-N [6-(4-ethyl-3,5-dimethylpyrazol-1-yl)pyridazin-3-yl]hydrazine Chemical compound CC1=C(CC)C(C)=NN1C1=CC=C(NN)N=N1 XOFBYGYMCBLZBB-UHFFFAOYSA-N 0.000 description 1
ODJCGPVWEOYLHP-UHFFFAOYSA-N [6-(4-nitropyrazol-1-yl)pyridazin-3-yl]hydrazine Chemical compound N1=NC(NN)=CC=C1N1N=CC([N+]([O-])=O)=C1 ODJCGPVWEOYLHP-UHFFFAOYSA-N 0.000 description 1
YCOBZYMXCHKSPQ-UHFFFAOYSA-N [6-(5-chloro-3-methylpyrazol-1-yl)pyridazin-3-yl]hydrazine Chemical compound N1=C(C)C=C(Cl)N1C1=CC=C(NN)N=N1 YCOBZYMXCHKSPQ-UHFFFAOYSA-N 0.000 description 1
JFOLLAAECNNNAR-UHFFFAOYSA-N [6-[3,5-di(propan-2-yl)pyrazol-1-yl]pyridazin-3-yl]hydrazine Chemical compound N(N)C=1N=NC(=CC=1)N1N=C(C=C1C(C)C)C(C)C JFOLLAAECNNNAR-UHFFFAOYSA-N 0.000 description 1
231100000460 acute oral toxicity Toxicity 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
HBBRVEMMVUOSTL-UHFFFAOYSA-N butyl n-aminocarbamate Chemical compound CCCCOC(=O)NN HBBRVEMMVUOSTL-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
ZUXNZUWOTSUBMN-UHFFFAOYSA-N hydralazine hydrochloride Chemical compound Cl.C1=CC=C2C(NN)=NN=CC2=C1 ZUXNZUWOTSUBMN-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
201000006370 kidney failure Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
VAWASHJAOJYWGT-UHFFFAOYSA-N n-benzyl-6-(3,5-dicyclopropylpyrazol-1-yl)pyridazin-3-amine Chemical compound C=1C=CC=CC=1CNC(N=N1)=CC=C1N1N=C(C2CC2)C=C1C1CC1 VAWASHJAOJYWGT-UHFFFAOYSA-N 0.000 description 1
REKFTCDQYUKZJD-UHFFFAOYSA-N n-cyclopropyl-6-(3,5-dimethylpyrazol-1-yl)pyridazin-3-amine Chemical compound N1=C(C)C=C(C)N1C(N=N1)=CC=C1NC1CC1 REKFTCDQYUKZJD-UHFFFAOYSA-N 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
230000007017 scission Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
UOWZUVNAGUAEQC-UHFFFAOYSA-N tiratricol Chemical compound IC1=CC(CC(=O)O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 UOWZUVNAGUAEQC-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CS784648A 1977-10-25 1978-07-11 Method of making the 3-/1-pyrazolyle-/paridazin derivatives CS217964B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS80370A CS217965B2 (cs)	1977-10-25	1980-01-18	Způsob výroby derivátů 3-(l-pyrazolyl)pyridazinu

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU77GO1381A HU176100B (en)	1977-10-25	1977-10-25	Process for preparing new 3-/1-pyrazolyl/-pyridazine derivatives

Publications (1)

Publication Number	Publication Date
CS217964B2 true CS217964B2 (en)	1983-02-25

Family

ID=10996838

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS784648A CS217964B2 (en)	1977-10-25	1978-07-11	Method of making the 3-/1-pyrazolyle-/paridazin derivatives

Country Status (24)

Country	Link
US (1)	US4224325A (hu)
JP (1)	JPS5461187A (hu)
AT (1)	AT359076B (hu)
AU (1)	AU525814B2 (hu)
BE (1)	BE868987A (hu)
CA (1)	CA1090337A (hu)
CH (1)	CH637951A5 (hu)
CS (1)	CS217964B2 (hu)
DD (1)	DD139848A5 (hu)
DE (1)	DE2831072A1 (hu)
DK (1)	DK317678A (hu)
ES (1)	ES471779A1 (hu)
FI (1)	FI63397C (hu)
FR (1)	FR2407211A1 (hu)
GB (1)	GB2007644B (hu)
HU (1)	HU176100B (hu)
IL (1)	IL55120A (hu)
IT (1)	IT1097156B (hu)
NL (1)	NL7807572A (hu)
NO (1)	NO149354C (hu)
PL (2)	PL115063B1 (hu)
SE (1)	SE437988B (hu)
SU (3)	SU847920A3 (hu)
YU (1)	YU169878A (hu)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4302457A (en) *	1977-04-13	1981-11-24	The Upjohn Company	Process for therapeutic treatment
US4302456A (en) *	1977-04-13	1981-11-24	The Upjohn Company	Process for therapeutic treatment
DE2935359A1 (de) *	1979-09-01	1981-03-26	Basf Ag, 67063 Ludwigshafen	6-imidazolyl-3-hydrazino-pyridazine
US4304775A (en) *	1979-12-13	1981-12-08	Sterling Drug Inc.	3-Hydrazino-6-(pyridinyl) pyridazines and cardiotonic use thereof
US4503056A (en) *	1982-03-02	1985-03-05	Abbott Laboratories	1-(Pyridazinyl)pyrazoline derivatives
US5001125A (en) *	1984-03-26	1991-03-19	Janssen Pharmaceutica N.V.	Anti-virally active pyridazinamines

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1220428B (de)	1960-03-25	1966-07-07	Takeda Pharmaceutical	Verfahren zur Herstellung von 2-Pyrazolyl-(1')-pyrimidinderivaten und deren Salzen
JPS5831347B2 (ja) *	1975-09-05	1983-07-05	中外製薬株式会社	ピラゾリルピリダジンユウドウタイノセイホウ
HU175471B (hu) *	1977-06-13	1980-08-28	Gyogyszerkutato Intezet	Sposob poluchenija novykh proizvodnykh 3-skobka-1-pirazolil-skobka zakryta-piridazina

1977
- 1977-10-25 HU HU77GO1381A patent/HU176100B/hu unknown
1978
- 1978-07-11 US US05/923,623 patent/US4224325A/en not_active Expired - Lifetime
- 1978-07-11 CS CS784648A patent/CS217964B2/cs unknown
- 1978-07-11 IL IL55120A patent/IL55120A/xx unknown
- 1978-07-13 AU AU37997/78A patent/AU525814B2/en not_active Expired
- 1978-07-13 FR FR7820938A patent/FR2407211A1/fr active Granted
- 1978-07-13 AT AT509278A patent/AT359076B/de not_active IP Right Cessation
- 1978-07-13 SE SE7807822A patent/SE437988B/sv unknown
- 1978-07-13 FI FI782237A patent/FI63397C/fi not_active IP Right Cessation
- 1978-07-14 CH CH764178A patent/CH637951A5/de not_active IP Right Cessation
- 1978-07-14 DK DK317678A patent/DK317678A/da not_active Application Discontinuation
- 1978-07-14 BE BE189273A patent/BE868987A/xx not_active IP Right Cessation
- 1978-07-14 PL PL1978208409A patent/PL115063B1/pl unknown
- 1978-07-14 NO NO782446A patent/NO149354C/no unknown
- 1978-07-14 NL NL7807572A patent/NL7807572A/xx not_active Application Discontinuation
- 1978-07-14 DE DE19782831072 patent/DE2831072A1/de not_active Withdrawn
- 1978-07-14 DD DD78206732A patent/DD139848A5/de unknown
- 1978-07-14 PL PL1978218031A patent/PL118799B1/pl unknown
- 1978-07-14 IT IT25681/78A patent/IT1097156B/it active
- 1978-07-14 YU YU01698/78A patent/YU169878A/xx unknown
- 1978-07-14 SU SU782639448A patent/SU847920A3/ru active
- 1978-07-14 CA CA307,397A patent/CA1090337A/en not_active Expired
- 1978-07-14 GB GB7829820A patent/GB2007644B/en not_active Expired
- 1978-07-15 JP JP8569878A patent/JPS5461187A/ja active Granted
- 1978-07-15 ES ES471779A patent/ES471779A1/es not_active Expired
1979
- 1979-08-23 SU SU792804755A patent/SU856385A3/ru active
- 1979-08-23 SU SU792803900A patent/SU845786A3/ru active

Also Published As

Publication number	Publication date
PL218031A1 (hu)	1980-07-14
NL7807572A (nl)	1979-04-27
NO149354B (no)	1983-12-27
AU525814B2 (en)	1982-12-02
BE868987A (fr)	1979-01-15
SU847920A3 (ru)	1981-07-15
FI782237A (fi)	1979-04-26
IT1097156B (it)	1985-08-26
GB2007644B (en)	1982-03-10
FR2407211A1 (fr)	1979-05-25
SU845786A3 (ru)	1981-07-07
SE437988B (sv)	1985-03-25
CA1090337A (en)	1980-11-25
IL55120A (en)	1982-05-31
NO149354C (no)	1984-04-04
DD139848A5 (de)	1980-01-23
PL115063B1 (en)	1981-03-31
DK317678A (da)	1979-04-26
ES471779A1 (es)	1979-10-01
FI63397B (fi)	1983-02-28
SE7807822L (sv)	1979-04-26
AT359076B (de)	1980-10-27
CH637951A5 (de)	1983-08-31
US4224325A (en)	1980-09-23
SU856385A3 (ru)	1981-08-15
FI63397C (fi)	1983-06-10
FR2407211B1 (hu)	1982-09-03
PL208409A1 (hu)	1980-02-25
NO782446L (no)	1979-04-26
PL118799B1 (en)	1981-10-31
YU169878A (en)	1983-01-21
GB2007644A (en)	1979-05-23
JPS5527063B2 (hu)	1980-07-17
DE2831072A1 (de)	1979-05-10
JPS5461187A (en)	1979-05-17
HU176100B (en)	1980-12-28
IT7825681A0 (it)	1978-07-14
ATA509278A (de)	1980-03-15
IL55120A0 (en)	1978-09-29
AU3799778A (en)	1980-01-17

Publication	Publication Date	Title
US4251658A (en)	1981-02-17	3-(1-Pyrazolyl)-pyridazine derivatives
DK156392B (da)	1989-08-14	Analogifremgangsmaade til fremstilling af aminopropoxyindolderivater
RU2193554C2 (ru)	2002-11-27	Производные ароматических аминов, обладающих подавляющим оас действием, способ их получения и ингибитор ноас
CS405291A3 (en)	1992-04-15	2-aminopyrimidine-4-carboxamide derivatives, process of their preparation and their application in therapy
US4950670A (en)	1990-08-21	6-phenyl-3-(piperazinyalalkyl)-2,4(1H,3H)-pyrimidinedione derivatives, their preparation and their application in therapy
US4585773A (en)	1986-04-29	Isoindolinyl-alkyl-piperazines
CS217964B2 (en)	1983-02-25	Method of making the 3-/1-pyrazolyle-/paridazin derivatives
EP0163240A2 (en)	1985-12-04	Dihydroimidazo[1,2-a]pyrimidine derivatives, methods of preparing said compounds and pharmaceutical compositions constaining said compounds
CA1084929A (en)	1980-09-02	1,2,4-triazolo 4,3-b pyridazin-3-ones
NO810870L (no)	1981-09-28	Fremgangsmaate til fremstilling av pyrimidylkinazoliner
US3478028A (en)	1969-11-11	4-substituted-1-hydroxylaminophthalazines
CS244653B2 (en)	1986-08-14	Production method of new pyridazinel-hydrazone derivatives
US3448105A (en)	1969-06-03	Basic esters of malonic acid
JP7416842B2 (ja)	2024-01-17	縮合多環式化合物の調製方法
JP5079809B2 (ja)	2012-11-21	（３−アルキル−５−ピペリジン−１−イル−３，３ａ−ジヒドロ−ピラゾロ［１，５−ａ］ピリミジン−７−イル）−アミノ誘導体および中間体の合成のための方法および合成のための中間体
US3287454A (en)	1966-11-22	1-substituted 4-isonicotinoylamino-piperazines
CS217965B2 (cs)	1983-02-25	Způsob výroby derivátů 3-(l-pyrazolyl)pyridazinu
US3265693A (en)	1966-08-09	3-phenyl-4-dialkylaminoalkylamino-cinnolines
KR810000804B1 (ko)	1981-07-08	헥사하이드로 피리미딘 화합물의 제조방법
Papoyan et al.	2012	Synthesis of new 6, 7-dihydro-1 H-cyclopenta [d] pyrimidine-2, 4 (3 H, 5 H)-dione derivatives containing the substituted aliphatic ring
JPH02289550A (ja)	1990-11-29	アゾール―１―アルカンアミドおよびそれらの製法
HU208975B (en)	1994-02-28	Process for producing imidazo/5,1-b/ quinazolin-9-one derivatives and pharmaceutically acceptable salts thereof, as well as thrombocyta aggregation inhibiting pharmaceutical compositions comprising such active ingredients
JPH05262774A (ja)	1993-10-12	ピロロ［３，２−ｅピラゾロ［１，５−ａピリミジン誘導体及びこれを含有する循環器系疾患治療剤
MXPA00002946A (en)	2001-07-09	9,10-dihydro-9, 10-ethanoanthracene derivatives as phospholipase inhibitors
IL25525A (en)	1970-04-20	1,2,8,9-tetraazaphenalenes and their preparation