FI64156C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat Download PDFInfo
- Publication number
- FI64156C FI64156C FI781856A FI781856A FI64156C FI 64156 C FI64156 C FI 64156C FI 781856 A FI781856 A FI 781856A FI 781856 A FI781856 A FI 781856A FI 64156 C FI64156 C FI 64156C
- Authority
- FI
- Finland
- Prior art keywords
- group
- general formula
- compound
- pyrazolyl
- cyano
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 230000001225 therapeutic effect Effects 0.000 title 2
- 235000013399 edible fruits Nutrition 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 cyano, carboxyl Chemical group 0.000 claims description 16
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- SKXBTBMQHHPISZ-UHFFFAOYSA-N 3-pyrazol-1-ylpyridazine Chemical compound C1=CC=NN1C1=CC=CN=N1 SKXBTBMQHHPISZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 150000004892 pyridazines Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 150000003180 prostaglandins Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LMNKIHGNJVOKAJ-UHFFFAOYSA-N 5-amino-1-(6-chloropyridazin-3-yl)pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=CC=C(Cl)N=N1 LMNKIHGNJVOKAJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 239000013078 crystal 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
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 229960002474 hydralazine Drugs 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- FXYQRYGWWZKUFV-UHFFFAOYSA-N (6-chloropyridazin-3-yl)hydrazine Chemical compound NNC1=CC=C(Cl)N=N1 FXYQRYGWWZKUFV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101710088194 Dehydrogenase Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- TXXNCHKKIABOJX-UHFFFAOYSA-N ethyl 5-amino-1-(6-chloropyridazin-3-yl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(Cl)N=N1 TXXNCHKKIABOJX-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OEICGMPRFOJHKO-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedinitrile Chemical compound CCOC=C(C#N)C#N OEICGMPRFOJHKO-UHFFFAOYSA-N 0.000 description 1
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-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
- 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 1
- KAGZGWUUTROZIC-UHFFFAOYSA-N 3-chloro-6-pyrazol-1-ylpyridazine Chemical compound N1=NC(Cl)=CC=C1N1N=CC=C1 KAGZGWUUTROZIC-UHFFFAOYSA-N 0.000 description 1
- JEPRVQOWVBIKSZ-UHFFFAOYSA-N 5-amino-1-(6-hydrazinylpyridazin-3-yl)pyrazole-4-carbohydrazide Chemical compound NC1=C(C(=O)NN)C=NN1C1=CC=C(NN)N=N1 JEPRVQOWVBIKSZ-UHFFFAOYSA-N 0.000 description 1
- IMEZMMYAGFXMFX-UHFFFAOYSA-N 5-amino-1-[6-[amino(methyl)amino]pyridazin-3-yl]pyrazole-4-carbonitrile Chemical compound N1=NC(N(N)C)=CC=C1N1C(N)=C(C#N)C=N1 IMEZMMYAGFXMFX-UHFFFAOYSA-N 0.000 description 1
- CWEWHPGGDUXDIU-UHFFFAOYSA-N 5-amino-1-[6-[bis(2-hydroxyethyl)amino]pyridazin-3-yl]pyrazole-4-carbohydrazide Chemical compound NC1=C(C(=O)NN)C=NN1C1=CC=C(N(CCO)CCO)N=N1 CWEWHPGGDUXDIU-UHFFFAOYSA-N 0.000 description 1
- DFQHZNILPSDYOG-UHFFFAOYSA-N 5-amino-1-pyridazin-3-ylpyrazole-4-carbohydrazide Chemical compound C(NN)(=O)C=1C=NN(C=1N)C=1N=NC=CC=1 DFQHZNILPSDYOG-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- JGXMHBNNUWTAOD-UHFFFAOYSA-N C1=C(N=CC(=N1)Cl)N2C(=C(C=N2)C(=O)N)N Chemical compound C1=C(N=CC(=N1)Cl)N2C(=C(C=N2)C(=O)N)N JGXMHBNNUWTAOD-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920013685 Estron Polymers 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- XJZBZTSBZQJAQZ-UHFFFAOYSA-N ethyl 5-amino-1-pyridazin-3-ylpyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=CN=N1 XJZBZTSBZQJAQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration 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
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- YTRGNBTVTHPFJM-UHFFFAOYSA-N pyridazin-3-ylhydrazine Chemical compound NNC1=CC=CN=N1 YTRGNBTVTHPFJM-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035488 systolic blood pressure Effects 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
- 230000002792 vascular 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
-
- 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001373 | 1977-06-13 | ||
| HU77GO1373A HU175471B (hu) | 1977-06-13 | 1977-06-13 | Sposob poluchenija novykh proizvodnykh 3-skobka-1-pirazolil-skobka zakryta-piridazina |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI781856A7 FI781856A7 (fi) | 1978-12-14 |
| FI64156B FI64156B (fi) | 1983-06-30 |
| FI64156C true FI64156C (fi) | 1983-10-10 |
Family
ID=10996834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI781856A FI64156C (fi) | 1977-06-13 | 1978-06-09 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4251658A (cs) |
| JP (1) | JPS5416487A (cs) |
| AT (1) | AT357548B (cs) |
| AU (1) | AU521394B2 (cs) |
| BE (1) | BE867967A (cs) |
| BG (1) | BG28709A3 (cs) |
| CA (1) | CA1095912A (cs) |
| CH (1) | CH638202A5 (cs) |
| CS (1) | CS204029B2 (cs) |
| DD (1) | DD140043A5 (cs) |
| DE (1) | DE2825906A1 (cs) |
| DK (1) | DK263078A (cs) |
| ES (1) | ES470750A1 (cs) |
| FI (1) | FI64156C (cs) |
| FR (1) | FR2394542A1 (cs) |
| GB (1) | GB1603958A (cs) |
| HU (1) | HU175471B (cs) |
| IL (1) | IL54816A (cs) |
| IT (1) | IT1098216B (cs) |
| NL (1) | NL7806380A (cs) |
| NO (1) | NO149210C (cs) |
| PL (1) | PL111252B1 (cs) |
| SE (1) | SE437517B (cs) |
| SU (2) | SU797577A3 (cs) |
| YU (1) | YU140078A (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU176100B (en) * | 1977-10-25 | 1980-12-28 | Gyogyszerkutato Intezet | Process for preparing new 3-/1-pyrazolyl/-pyridazine derivatives |
| DE2935359A1 (de) * | 1979-09-01 | 1981-03-26 | Basf Ag, 67063 Ludwigshafen | 6-imidazolyl-3-hydrazino-pyridazine |
| DE3130251A1 (de) * | 1981-07-31 | 1983-02-17 | A. Nattermann & Cie GmbH, 5000 Köln | 6-(4-((omega)-(1-imidazolyl)-alkyl)-phenyl)-3-oxo -2,3,4,5-tetrahydro-pyridazine und deren saeureadditionssalze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4353905A (en) * | 1981-09-17 | 1982-10-12 | Warner-Lambert Company | Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones |
| US4590194A (en) * | 1981-10-05 | 1986-05-20 | Sterling Drug Inc. | 3-[methyl or dimethyl)amino]-6-(pyridinyl)pyridazines and their cardiotonic use |
| US4503056A (en) * | 1982-03-02 | 1985-03-05 | Abbott Laboratories | 1-(Pyridazinyl)pyrazoline derivatives |
| DE3825867A1 (de) * | 1988-03-04 | 1989-09-14 | Bayer Ag | Heterocyclisch substituierte sulfonylaminoazole und ihre verwendung als herbizide |
| US5536701A (en) * | 1994-10-11 | 1996-07-16 | Monsanto Company | 3-pyrazolyloxypyridazines, herbicidal compositions and uses thereof |
| FR2847160A1 (fr) * | 2002-11-20 | 2004-05-21 | Oreal | Composition capillaire contenant un compose pyrasol-carboxamide, son utilisation pour stimuler la pousse des cheveux et/ou freiner leur chute |
| WO2004047776A1 (fr) * | 2002-11-20 | 2004-06-10 | L'oreal | Utilisation d’un compose pyrazolcarboxamide pour stimuler la pousse des fibres keratiniques et/ou freiner leur chute |
| RU2442775C2 (ru) * | 2005-07-04 | 2012-02-20 | Хай Пойнт Фармасьютикалс, ЛЛС | Антагонисты гистаминовых н3-рецепторов |
| MX2007015675A (es) * | 2005-07-04 | 2008-02-20 | Novo Nordisk As | Antagonistas del receptor de histamina h3. |
| CA2653062A1 (en) * | 2006-05-23 | 2007-11-29 | Transtech Pharma, Inc. | 6- (4-cyclopropylpiperazin-1-yl) -2 ' -methyl- [3, 4 ' ] -bipyridine and its use as a medicament |
| BRPI0711370A2 (pt) * | 2006-05-29 | 2011-11-01 | High Point Pharmaceuticals Llc | 3-(1,3-benzodioxol-5-il)-6-(4-ciclopropilpiperazin-1-il)pi ridazina e seus sais e solvatos e seu uso como antagonista receptor h3 de histamina |
| EP2014656A3 (en) * | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | New heteocyclic h3 antagonists |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) * | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| WO2011133920A1 (en) | 2010-04-23 | 2011-10-27 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1595920B2 (de) * | 1964-11-04 | 1978-08-10 | Merck Patent Gmbh, 6100 Darmstadt | 4-(co-Piperazinoalkyl)-pyrazole, ihre Salze und Verfahren zu ihrer Herstellung |
| 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 |
-
1977
- 1977-06-13 HU HU77GO1373A patent/HU175471B/hu unknown
-
1978
- 1978-05-30 IL IL54816A patent/IL54816A/xx unknown
- 1978-05-31 GB GB25603/78A patent/GB1603958A/en not_active Expired
- 1978-06-02 AU AU36836/78A patent/AU521394B2/en not_active Expired
- 1978-06-05 SE SE7806576A patent/SE437517B/sv unknown
- 1978-06-07 AT AT414478A patent/AT357548B/de not_active IP Right Cessation
- 1978-06-09 DD DD78205915A patent/DD140043A5/de unknown
- 1978-06-09 BE BE1008923A patent/BE867967A/xx not_active IP Right Cessation
- 1978-06-09 CS CS783783A patent/CS204029B2/cs unknown
- 1978-06-09 CA CA305,147A patent/CA1095912A/en not_active Expired
- 1978-06-09 FI FI781856A patent/FI64156C/fi not_active IP Right Cessation
- 1978-06-09 US US05/914,084 patent/US4251658A/en not_active Expired - Lifetime
- 1978-06-12 DK DK263078A patent/DK263078A/da not_active Application Discontinuation
- 1978-06-12 BG BG040047A patent/BG28709A3/xx unknown
- 1978-06-12 NO NO782043A patent/NO149210C/no unknown
- 1978-06-12 CH CH636678A patent/CH638202A5/de not_active IP Right Cessation
- 1978-06-12 FR FR7817429A patent/FR2394542A1/fr active Granted
- 1978-06-12 SU SU782626901A patent/SU797577A3/ru active
- 1978-06-12 PL PL1978207570A patent/PL111252B1/pl unknown
- 1978-06-13 NL NL7806380A patent/NL7806380A/xx not_active Application Discontinuation
- 1978-06-13 DE DE19782825906 patent/DE2825906A1/de not_active Withdrawn
- 1978-06-13 JP JP7043978A patent/JPS5416487A/ja active Granted
- 1978-06-13 IT IT24490/78A patent/IT1098216B/it active
- 1978-06-13 YU YU01400/78A patent/YU140078A/xx unknown
- 1978-06-13 ES ES470750A patent/ES470750A1/es not_active Expired
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1979
- 1979-06-18 SU SU792777209A patent/SU860703A1/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYESZETI GYOER R.T. |