FI63397C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat - Google Patents

Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat Download PDF

Info

Publication number: FI63397C
Authority: FI; Finland
Prior art keywords: pyrazolyl; alkyl; nhr; group; pyridazine
Prior art date: 1977-10-25

Application number

FI782237A

Other languages

English (en)

Finnish (fi)

Other versions

FI782237A7 (fi

FI63397B (fi

Inventor

Geza Szilagyi

Endre Kasztreiner

Laszlo Tardos

Edit Kosa

Laszlo Jaszlits

Gyoergy Cseh

Nee 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

1978-07-13

Publication date

1983-06-10

1978-07-13 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1979-04-26 Publication of FI782237A7 publication Critical patent/FI782237A7/fi

1983-02-28 Application granted granted Critical

1983-02-28 Publication of FI63397B publication Critical patent/FI63397B/fi

1983-06-10 Publication of FI63397C publication Critical patent/FI63397C/fi

Links

238000000034 method Methods 0.000 title claims description 14
230000001225 therapeutic effect Effects 0.000 title 2
235000013399 edible fruits Nutrition 0.000 title 1
238000002360 preparation method Methods 0.000 claims description 38
150000001875 compounds Chemical class 0.000 claims description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
SKXBTBMQHHPISZ-UHFFFAOYSA-N 3-pyrazol-1-ylpyridazine Chemical class C1=CC=NN1C1=CC=CN=N1 SKXBTBMQHHPISZ-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 claims 2
101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims 1
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 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
-1 dimethyl-1-pyrazolyl Chemical group 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
150000003180 prostaglandins Chemical class 0.000 description 8
239000002904 solvent Substances 0.000 description 7
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 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 5
229960002474 hydralazine Drugs 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 4
229940127204 compound 29 Drugs 0.000 description 4
230000001077 hypotensive effect Effects 0.000 description 4
230000002401 inhibitory effect Effects 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
239000002244 precipitate Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
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238000003756 stirring Methods 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
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 2
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 2
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 2
KAGZGWUUTROZIC-UHFFFAOYSA-N 3-chloro-6-pyrazol-1-ylpyridazine Chemical compound N1=NC(Cl)=CC=C1N1N=CC=C1 KAGZGWUUTROZIC-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
206010020772 Hypertension Diseases 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
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
230000015556 catabolic process Effects 0.000 description 2
238000006243 chemical reaction Methods 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
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 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
150000007524 organic acids Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
206010038464 renal hypertension Diseases 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
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
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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
GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
ARYJTTGRKRAXMP-UHFFFAOYSA-N 3-(3,5-dimethyl-4-nitropyrazol-1-yl)pyridazine Chemical compound CC1=NN(C(=C1[N+](=O)[O-])C)C=1N=NC=CC=1 ARYJTTGRKRAXMP-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
HCBNIMHZSVRXBO-UHFFFAOYSA-N 3-chloro-6-(3,4,5-trimethylpyrazol-1-yl)pyridazine Chemical compound CC1=C(C)C(C)=NN1C1=CC=C(Cl)N=N1 HCBNIMHZSVRXBO-UHFFFAOYSA-N 0.000 description 1
QWWPATJTWJSXDI-UHFFFAOYSA-N 3-chloro-6-(3,5-diethyl-4-nitropyrazol-1-yl)pyridazine Chemical compound CCC1=C([N+]([O-])=O)C(CC)=NN1C1=CC=C(Cl)N=N1 QWWPATJTWJSXDI-UHFFFAOYSA-N 0.000 description 1
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 1
IJHFMWKKBHPENZ-UHFFFAOYSA-N 3-chloro-6-(3,5-dimethyl-5-propan-2-yl-1H-pyrazol-2-yl)pyridazine Chemical compound ClC=1N=NC(=CC=1)N1NC(C=C1C)(C(C)C)C IJHFMWKKBHPENZ-UHFFFAOYSA-N 0.000 description 1
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150000008282 halocarbons Chemical class 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
201000006370 kidney failure Diseases 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 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
229910052759 nickel Inorganic materials 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
235000005985 organic acids Nutrition 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 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 compound 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
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- 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

Landscapes

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

FI782237A 1977-10-25 1978-07-13 Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat FI63397C (fi)

Applications Claiming Priority (2)

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
HUGO001381		1977-10-25

Publications (3)

Publication Number	Publication Date
FI782237A7 FI782237A7 (fi)	1979-04-26
FI63397B FI63397B (fi)	1983-02-28
FI63397C true FI63397C (fi)	1983-06-10

Family

ID=10996838

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI782237A FI63397C (fi)	1977-10-25	1978-07-13	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat

Country Status (24)

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

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4302456A (en) *	1977-04-13	1981-11-24	The Upjohn Company	Process for therapeutic treatment
US4302457A (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 CS CS784648A patent/CS217964B2/cs unknown
- 1978-07-11 US US05/923,623 patent/US4224325A/en not_active Expired - Lifetime
- 1978-07-11 IL IL55120A patent/IL55120A/xx unknown
- 1978-07-13 FR FR7820938A patent/FR2407211A1/fr active Granted
- 1978-07-13 AU AU37997/78A patent/AU525814B2/en not_active Expired
- 1978-07-13 SE SE7807822A patent/SE437988B/sv unknown
- 1978-07-13 FI FI782237A patent/FI63397C/fi not_active IP Right Cessation
- 1978-07-13 AT AT509278A patent/AT359076B/de not_active IP Right Cessation
- 1978-07-14 GB GB7829820A patent/GB2007644B/en not_active Expired
- 1978-07-14 NL NL7807572A patent/NL7807572A/xx not_active Application Discontinuation
- 1978-07-14 CH CH764178A patent/CH637951A5/de not_active IP Right Cessation
- 1978-07-14 PL PL1978208409A patent/PL115063B1/pl unknown
- 1978-07-14 IT IT25681/78A patent/IT1097156B/it active
- 1978-07-14 SU SU782639448A patent/SU847920A3/ru active
- 1978-07-14 DD DD78206732A patent/DD139848A5/de unknown
- 1978-07-14 NO NO782446A patent/NO149354C/no unknown
- 1978-07-14 DE DE19782831072 patent/DE2831072A1/de not_active Withdrawn
- 1978-07-14 PL PL1978218031A patent/PL118799B1/pl unknown
- 1978-07-14 CA CA307,397A patent/CA1090337A/en not_active Expired
- 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 YU YU01698/78A patent/YU169878A/xx unknown
- 1978-07-15 ES ES471779A patent/ES471779A1/es not_active Expired
- 1978-07-15 JP JP8569878A patent/JPS5461187A/ja active Granted
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
PL208409A1 (cs)	1980-02-25
HU176100B (en)	1980-12-28
ATA509278A (de)	1980-03-15
BE868987A (fr)	1979-01-15
SU847920A3 (ru)	1981-07-15
NO149354B (no)	1983-12-27
FI782237A7 (fi)	1979-04-26
GB2007644B (en)	1982-03-10
ES471779A1 (es)	1979-10-01
DK317678A (da)	1979-04-26
PL118799B1 (en)	1981-10-31
AU3799778A (en)	1980-01-17
US4224325A (en)	1980-09-23
CH637951A5 (de)	1983-08-31
JPS5461187A (en)	1979-05-17
PL218031A1 (cs)	1980-07-14
SU856385A3 (ru)	1981-08-15
DD139848A5 (de)	1980-01-23
GB2007644A (en)	1979-05-23
IL55120A (en)	1982-05-31
SU845786A3 (ru)	1981-07-07
CA1090337A (en)	1980-11-25
CS217964B2 (en)	1983-02-25
AT359076B (de)	1980-10-27
SE437988B (sv)	1985-03-25
IL55120A0 (en)	1978-09-29
AU525814B2 (en)	1982-12-02
FR2407211B1 (cs)	1982-09-03
IT1097156B (it)	1985-08-26
JPS5527063B2 (cs)	1980-07-17
IT7825681A0 (it)	1978-07-14
PL115063B1 (en)	1981-03-31
YU169878A (en)	1983-01-21
NO782446L (no)	1979-04-26
NO149354C (no)	1984-04-04
SE7807822L (sv)	1979-04-26
NL7807572A (nl)	1979-04-27
DE2831072A1 (de)	1979-05-10
FI63397B (fi)	1983-02-28
FR2407211A1 (fr)	1979-05-25

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: RICHTER GEDEON VEGYESZETI GYAR R.T.

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