FI63397C - 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
- FI63397C FI63397C FI782237A FI782237A FI63397C FI 63397 C FI63397 C FI 63397C FI 782237 A FI782237 A FI 782237A FI 782237 A FI782237 A FI 782237A FI 63397 C FI63397 C FI 63397C
- Authority
- FI
- Finland
- Prior art keywords
- pyrazolyl
- alkyl
- nhr
- group
- pyridazine
- Prior art date
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
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- RRDJAMIJIKVWHH-UHFFFAOYSA-N 1-[6-(3,5-dimethylpyrazol-1-yl)pyridazin-3-yl]-1-methylhydrazine Chemical compound N1=NC(N(N)C)=CC=C1N1C(C)=CC(C)=N1 RRDJAMIJIKVWHH-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
- 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
- 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
- NZEYPAXAQSCGHD-UHFFFAOYSA-N 3-chloro-6-(4-ethyl-3,5-dimethylpyrazol-1-yl)pyridazine Chemical compound CC1=C(CC)C(C)=NN1C1=CC=C(Cl)N=N1 NZEYPAXAQSCGHD-UHFFFAOYSA-N 0.000 description 1
- GMXJGCJMTDZLER-UHFFFAOYSA-N 3-chloro-6-(4-nitropyrazol-1-yl)pyridazine Chemical compound C1=C([N+](=O)[O-])C=NN1C1=CC=C(Cl)N=N1 GMXJGCJMTDZLER-UHFFFAOYSA-N 0.000 description 1
- OLKAKOLMLGTPCY-UHFFFAOYSA-N 3-chloro-6-(5-chloro-3-methylpyrazol-1-yl)pyridazine Chemical compound N1=C(C)C=C(Cl)N1C1=CC=C(Cl)N=N1 OLKAKOLMLGTPCY-UHFFFAOYSA-N 0.000 description 1
- CSIFGMFVGDBOQC-UHFFFAOYSA-N 3-iminobutanenitrile Chemical compound CC(=N)CC#N CSIFGMFVGDBOQC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-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
- CXSKLCIEINDCRR-UHFFFAOYSA-N CC1=C(Cl)C(C)=NN1C1=CC=NN=C1Cl Chemical compound CC1=C(Cl)C(C)=NN1C1=CC=NN=C1Cl CXSKLCIEINDCRR-UHFFFAOYSA-N 0.000 description 1
- BKWFUUWNTYXAKE-UHFFFAOYSA-N CCC1C(=N)C(=NN1C2=NN=C(C=C2)NN)CC Chemical compound CCC1C(=N)C(=NN1C2=NN=C(C=C2)NN)CC BKWFUUWNTYXAKE-UHFFFAOYSA-N 0.000 description 1
- UWGGRBKQVZVLRV-UHFFFAOYSA-N ClC=1N=NC(=CC=1)N1N=C(C(=C1CC)N)CC Chemical compound ClC=1N=NC(=CC=1)N1N=C(C(=C1CC)N)CC UWGGRBKQVZVLRV-UHFFFAOYSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 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
- 108010020056 Hydrogenase Proteins 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 102000004195 Isomerases Human genes 0.000 description 1
- 108090000769 Isomerases Proteins 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
- 208000001871 Tachycardia Diseases 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- PJHKOSYTSUNMEQ-UHFFFAOYSA-N [6-(3,5-dimethylpyrazol-1-yl)pyridazin-3-yl]hydrazine Chemical compound N1=C(C)C=C(C)N1C1=CC=C(NN)N=N1 PJHKOSYTSUNMEQ-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001381 | 1977-10-25 | ||
| HU77GO1381A HU176100B (en) | 1977-10-25 | 1977-10-25 | Process for preparing new 3-/1-pyrazolyl/-pyridazine derivatives |
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)
| 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)
| 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 IL IL55120A patent/IL55120A/xx unknown
- 1978-07-11 CS CS784648A patent/CS217964B2/cs 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 FI FI782237A patent/FI63397C/fi not_active IP Right Cessation
- 1978-07-13 SE SE7807822A patent/SE437988B/sv unknown
- 1978-07-13 AT AT509278A patent/AT359076B/de not_active IP Right Cessation
- 1978-07-14 CA CA307,397A patent/CA1090337A/en not_active Expired
- 1978-07-14 PL PL1978208409A patent/PL115063B1/pl unknown
- 1978-07-14 BE BE189273A patent/BE868987A/xx not_active IP Right Cessation
- 1978-07-14 NL NL7807572A patent/NL7807572A/xx not_active Application Discontinuation
- 1978-07-14 PL PL1978218031A patent/PL118799B1/pl unknown
- 1978-07-14 DK DK317678A patent/DK317678A/da not_active Application Discontinuation
- 1978-07-14 IT IT25681/78A patent/IT1097156B/it active
- 1978-07-14 SU SU782639448A patent/SU847920A3/ru active
- 1978-07-14 NO NO782446A patent/NO149354C/no unknown
- 1978-07-14 DD DD78206732A patent/DD139848A5/de unknown
- 1978-07-14 CH CH764178A patent/CH637951A5/de not_active IP Right Cessation
- 1978-07-14 GB GB7829820A patent/GB2007644B/en not_active Expired
- 1978-07-14 YU YU01698/78A patent/YU169878A/xx unknown
- 1978-07-14 DE DE19782831072 patent/DE2831072A1/de not_active Withdrawn
- 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI64156B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat | |
| US20030229229A1 (en) | Process for preparing indolinone derivatives | |
| AU2014285733A1 (en) | Bicyclic compounds useful for treating diseases caused by retroviruses | |
| FI63397C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-pyrazolyl)-pyridazinderivat | |
| JP6374436B2 (ja) | 純粋なエルロチニブ | |
| CN101774993A (zh) | 白杨素含氮衍生物及其制备方法和用途 | |
| Greco et al. | Synthesis of sydnones and sydnone imines | |
| RU2193554C2 (ru) | Производные ароматических аминов, обладающих подавляющим оас действием, способ их получения и ингибитор ноас | |
| KR20180032784A (ko) | 신규한 이미다졸일 피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물 | |
| WO2017114843A1 (en) | Xanthine derivative inhibitors of bet proteins | |
| CN106349224A (zh) | 一种含有4‑氨基‑(1h)‑吡唑结构的jak激酶抑制剂及其制备方法和应用 | |
| CN108997176B (zh) | 一种4-氯-n-取代苯基-3-磺酰氨基苯甲酰胺类化合物及其制备和抗肿瘤应用 | |
| HUT61002A (en) | Process for producing 2-aminopyrimdine-4-carboxamide derivatives and pharmaceutical compositions comprising such compounds | |
| Xu et al. | Discovery of novel 4-trifluoromethyl-2-anilinoquinoline derivatives as potential anti-cancer agents targeting SGK1 | |
| US10202349B2 (en) | Asymmetric bis-acridines with antitumour activity and their uses | |
| CS244653B2 (en) | Production method of new pyridazinel-hydrazone derivatives | |
| US6015811A (en) | Antitumor Chrysene derivatives | |
| Eißmann et al. | Synthesis and structural characterization of amino acid and peptide derivatives featuring N-(p-bromobenzoyl) substituents as promising connection unit for bio-inspired hybrid compounds | |
| WO2020017624A1 (ja) | 抗がん剤 | |
| Al-Soud et al. | Nitroimidazoles part 8. Synthesis and anti-HIV activity of new 4-nitroimidazole derivatives using the suzuki cross-coupling reaction | |
| CN114478534B (zh) | 具有抗肿瘤活性的嵌合分子及其制备方法和应用 | |
| WO2024144680A1 (en) | Specific arylidene barbiturate derivative molecules for use as drug candidates in cancer treatment | |
| Moinet-Hedin et al. | In vitro cytotoxicity of carbazole derivatives. V. 9-Halogeno-substituted 5, 11-dimethyl-6H-pyrido [3, 2-b] carbazoles | |
| JP2014156442A (ja) | アリールピペラジン誘導体又はその塩の製造方法 | |
| SU1085204A1 (ru) | 4,9-БИС-АМИНОПРОИЗВОДНЫЕ ДИПИРИМИДО-5Н-(4,5-в)-(4',5 '-е)-(1,4) ТИАЗИНА, ОБЛАДАЮЩИЕ ЦИТОСТАТИЧЕСКИМ, ПРОТИВООПУХОЛЕВЫМ И АНТИРЕДУКТАЗНЫМ ДЕЙСТВИЕМ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYESZETI GYAR R.T. |