SE435505B - Nytt sett att framstella 6-(substituerad amino)-3-pyridazinylhydrazin - Google Patents
Nytt sett att framstella 6-(substituerad amino)-3-pyridazinylhydrazinInfo
- Publication number
- SE435505B SE435505B SE8003394A SE8003394A SE435505B SE 435505 B SE435505 B SE 435505B SE 8003394 A SE8003394 A SE 8003394A SE 8003394 A SE8003394 A SE 8003394A SE 435505 B SE435505 B SE 435505B
- Authority
- SE
- Sweden
- Prior art keywords
- carbon atoms
- group
- pyridazinyl
- hydrazine
- general formula
- Prior art date
Links
- -1 6- (SUBSTITUTED AMINO) -3-PYRIDAZINYL HYDRAZINE Chemical class 0.000 title claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 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 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- 230000001077 hypotensive effect Effects 0.000 claims 2
- 150000002429 hydrazines Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 239000002904 solvent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- FXYQRYGWWZKUFV-UHFFFAOYSA-N (6-chloropyridazin-3-yl)hydrazine Chemical compound NNC1=CC=C(Cl)N=N1 FXYQRYGWWZKUFV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 4
- 241000723346 Cinnamomum camphora Species 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229930008380 camphor Chemical class 0.000 description 4
- 229960000846 camphor Drugs 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- PHBNMZNMGUQCFK-UHFFFAOYSA-N (6-morpholin-4-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1N1CCOCC1 PHBNMZNMGUQCFK-UHFFFAOYSA-N 0.000 description 3
- 150000003935 benzaldehydes Chemical class 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- FTMUIFNGBPUUEA-UHFFFAOYSA-N 6-morpholin-4-yl-n-[(4-nitrophenyl)methylideneamino]pyridazin-3-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=NNC1=CC=C(N2CCOCC2)N=N1 FTMUIFNGBPUUEA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BJYPFYDGNROOPO-UHFFFAOYSA-N acetic acid;6-chloro-n-[(7,7-dimethyl-3-bicyclo[2.2.1]heptanylidene)amino]-n-methylpyridazin-3-amine Chemical compound CC(O)=O.C1C(C2(C)C)CCC2C1=NN(C)C1=CC=C(Cl)N=N1 BJYPFYDGNROOPO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- LQBIUKQHHHZEGN-UHFFFAOYSA-N n-[(7,7-dimethyl-3-bicyclo[2.2.1]heptanylidene)amino]-n-methyl-6-morpholin-4-ylpyridazin-3-amine Chemical compound C1C(C2(C)C)CCC2C1=NN(C)C(N=N1)=CC=C1N1CCOCC1 LQBIUKQHHHZEGN-UHFFFAOYSA-N 0.000 description 2
- PASFMPAKQJFVOG-UHFFFAOYSA-N n-methyl-6-morpholin-4-yl-n-[(4-nitrophenyl)methylideneamino]pyridazin-3-amine Chemical compound C=1C=C(N2CCOCC2)N=NC=1N(C)N=CC1=CC=C([N+]([O-])=O)C=C1 PASFMPAKQJFVOG-UHFFFAOYSA-N 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000004892 pyridazines Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- YGPAJUBACUQPDB-UHFFFAOYSA-N (4-methoxyphenyl)methylidenehydrazine Chemical class COC1=CC=C(C=NN)C=C1 YGPAJUBACUQPDB-UHFFFAOYSA-N 0.000 description 1
- VMNXLLDFGVEBLE-UHFFFAOYSA-N (4-methylsulfonylphenyl)methanamine Chemical compound CS(=O)(=O)C1=CC=C(CN)C=C1 VMNXLLDFGVEBLE-UHFFFAOYSA-N 0.000 description 1
- CUGVKCJTONTOPS-UHFFFAOYSA-N (6-morpholin-4-ylpyridazin-3-yl)hydrazine;dihydrochloride Chemical compound Cl.Cl.N1=NC(NN)=CC=C1N1CCOCC1 CUGVKCJTONTOPS-UHFFFAOYSA-N 0.000 description 1
- ZUTZIMYUEFESGE-UHFFFAOYSA-N (6-piperidin-1-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1N1CCCCC1 ZUTZIMYUEFESGE-UHFFFAOYSA-N 0.000 description 1
- LZOKSMYDAPAXOX-UHFFFAOYSA-N (6-pyrrolidin-1-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1N1CCCC1 LZOKSMYDAPAXOX-UHFFFAOYSA-N 0.000 description 1
- CRKDNNLDFYKBEE-RMKNXTFCSA-N (e)-benzylidenehydrazine Chemical class N\N=C\C1=CC=CC=C1 CRKDNNLDFYKBEE-RMKNXTFCSA-N 0.000 description 1
- HBGQTGGDURWSRC-UHFFFAOYSA-N 1-methyl-1-(6-morpholin-4-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(N(N)C)=CC=C1N1CCOCC1 HBGQTGGDURWSRC-UHFFFAOYSA-N 0.000 description 1
- OZNVZPWTJZHXFC-UHFFFAOYSA-N 2-(2-amino-2-pyridazin-3-ylhydrazinyl)ethanol Chemical compound OCCNN(C=1N=NC=CC=1)N OZNVZPWTJZHXFC-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- MAJCSAQXYOYMDQ-UHFFFAOYSA-N 6-chloro-N-(heptylideneamino)pyridazin-3-amine Chemical compound C(CCCCCC)=NNC=1N=NC(=CC=1)Cl MAJCSAQXYOYMDQ-UHFFFAOYSA-N 0.000 description 1
- CKFSOHCIIFDNID-UHFFFAOYSA-N 6-chloro-n-[(4-methoxyphenyl)methylideneamino]pyridazin-3-amine Chemical compound C1=CC(OC)=CC=C1C=NNC1=CC=C(Cl)N=N1 CKFSOHCIIFDNID-UHFFFAOYSA-N 0.000 description 1
- VVBIJCFLZWBSAU-UHFFFAOYSA-N 6-chloro-n-[(4-methylsulfonylphenyl)methylideneamino]pyridazin-3-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C=NNC1=CC=C(Cl)N=N1 VVBIJCFLZWBSAU-UHFFFAOYSA-N 0.000 description 1
- CFYXIAFKDLLULQ-UHFFFAOYSA-N 6-chloro-n-[(4-nitrophenyl)methylideneamino]pyridazin-3-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=NNC1=CC=C(Cl)N=N1 CFYXIAFKDLLULQ-UHFFFAOYSA-N 0.000 description 1
- ASFRWZJVUWDCEQ-UHFFFAOYSA-N 6-chloro-n-[(7,7-dimethyl-3-bicyclo[2.2.1]heptanylidene)amino]-n-methylpyridazin-3-amine Chemical compound C1C(C2(C)C)CCC2C1=NN(C)C1=CC=C(Cl)N=N1 ASFRWZJVUWDCEQ-UHFFFAOYSA-N 0.000 description 1
- PTWOTPSPVMARJR-UHFFFAOYSA-N 6-chloro-n-methyl-n-[(4-nitrophenyl)methylideneamino]pyridazin-3-amine Chemical compound C=1C=C(Cl)N=NC=1N(C)N=CC1=CC=C([N+]([O-])=O)C=C1 PTWOTPSPVMARJR-UHFFFAOYSA-N 0.000 description 1
- AUMDUHDIFCDVGW-UHFFFAOYSA-N 6-hydrazinyl-n,n-dimethylpyridazin-3-amine Chemical compound CN(C)C1=CC=C(NN)N=N1 AUMDUHDIFCDVGW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical class COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- FQBCKWYSLBKCTR-UHFFFAOYSA-N n-(benzylideneamino)-6-chloropyridazin-3-amine Chemical class N1=NC(Cl)=CC=C1NN=CC1=CC=CC=C1 FQBCKWYSLBKCTR-UHFFFAOYSA-N 0.000 description 1
- PDENUHSYBJCEDA-UHFFFAOYSA-N n-(benzylideneamino)pyridazin-3-amine Chemical class C=1C=CN=NC=1NN=CC1=CC=CC=C1 PDENUHSYBJCEDA-UHFFFAOYSA-N 0.000 description 1
- MZRKZWHARUTPOD-UHFFFAOYSA-N n-cyclohexyl-6-hydrazinylpyridazin-3-amine Chemical compound N1=NC(NN)=CC=C1NC1CCCCC1 MZRKZWHARUTPOD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- YTRGNBTVTHPFJM-UHFFFAOYSA-N pyridazin-3-ylhydrazine Chemical class NNC1=CC=CN=N1 YTRGNBTVTHPFJM-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (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)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79GO1445A HU179191B (en) | 1979-05-07 | 1979-05-07 | New process for preparing 6-/substituted amino/-3-pyridazinyl-hydrazines and salts thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8003394L SE8003394L (sv) | 1980-11-08 |
| SE435505B true SE435505B (sv) | 1984-10-01 |
Family
ID=10996892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8003394A SE435505B (sv) | 1979-05-07 | 1980-05-06 | Nytt sett att framstella 6-(substituerad amino)-3-pyridazinylhydrazin |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4329457A (OSRAM) |
| JP (1) | JPS55153773A (OSRAM) |
| AT (1) | AT372952B (OSRAM) |
| AU (1) | AU531409B2 (OSRAM) |
| BE (1) | BE883082A (OSRAM) |
| CH (1) | CH642636A5 (OSRAM) |
| DE (1) | DE3017508A1 (OSRAM) |
| DK (1) | DK148178C (OSRAM) |
| ES (1) | ES491240A0 (OSRAM) |
| FR (1) | FR2456092A1 (OSRAM) |
| GB (1) | GB2049691B (OSRAM) |
| HU (1) | HU179191B (OSRAM) |
| IL (1) | IL60008A (OSRAM) |
| IT (1) | IT1174668B (OSRAM) |
| NL (1) | NL8002598A (OSRAM) |
| SE (1) | SE435505B (OSRAM) |
| SU (1) | SU999967A3 (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1150070B (it) * | 1980-12-22 | 1986-12-10 | Lepetit Spa | Procedimento per preparare derivati n-pirrolipiridazinamminici |
| IT1164198B (it) * | 1983-04-28 | 1987-04-08 | Isf Spa | Preparazione di un derivato piridazinico farmacologicamente attivo |
| FR2668151A1 (fr) * | 1990-10-23 | 1992-04-24 | Rhone Poulenc Agrochimie | Composes a groupe triazolopyridazine leurs preparations et compositions herbicides les contenant. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2858311A (en) * | 1955-08-31 | 1958-10-28 | Sterling Drug Inc | 3, 6-bis(tertiary-amino-aliphatic) substituted pyridazines, and their preparation |
| IT1054107B (it) * | 1970-12-15 | 1981-11-10 | Isf Spa | Nuove 3,idrazinopiridazine 6,sostituite ad attivita antiiperten siva e loro preparazione |
| US3717632A (en) * | 1971-01-29 | 1973-02-20 | Sandoz Ag | Substituted-3-hydrazino pyridazines |
| ES431009A1 (es) * | 1974-05-09 | 1976-10-16 | Isf Spa | Procedimiento para la preparacion de derivados de 3-benci- lidenhidracino-6-aminopiridacina. |
| HU176972B (hu) * | 1977-06-13 | 1981-06-28 | Gyogyszerkutato Intezet | Sposob poluchenija novykh proizvodnykh piridazinil-gidrazona |
-
1979
- 1979-05-07 HU HU79GO1445A patent/HU179191B/hu unknown
-
1980
- 1980-05-02 BE BE1/9807A patent/BE883082A/fr not_active IP Right Cessation
- 1980-05-05 FR FR8009947A patent/FR2456092A1/fr active Granted
- 1980-05-06 IT IT21807/80A patent/IT1174668B/it active
- 1980-05-06 AT AT0242180A patent/AT372952B/de not_active IP Right Cessation
- 1980-05-06 GB GB8014998A patent/GB2049691B/en not_active Expired
- 1980-05-06 SE SE8003394A patent/SE435505B/sv not_active IP Right Cessation
- 1980-05-06 JP JP5878880A patent/JPS55153773A/ja active Pending
- 1980-05-06 US US06/147,224 patent/US4329457A/en not_active Expired - Lifetime
- 1980-05-06 IL IL60008A patent/IL60008A/xx unknown
- 1980-05-06 NL NL8002598A patent/NL8002598A/nl not_active Application Discontinuation
- 1980-05-06 DK DK198280A patent/DK148178C/da active
- 1980-05-06 CH CH351280A patent/CH642636A5/de not_active IP Right Cessation
- 1980-05-06 AU AU58122/80A patent/AU531409B2/en not_active Ceased
- 1980-05-07 ES ES491240A patent/ES491240A0/es active Granted
- 1980-05-07 DE DE19803017508 patent/DE3017508A1/de not_active Withdrawn
- 1980-05-07 SU SU802917855A patent/SU999967A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2456092B1 (OSRAM) | 1983-08-05 |
| AU531409B2 (en) | 1983-08-25 |
| US4329457A (en) | 1982-05-11 |
| CH642636A5 (de) | 1984-04-30 |
| IT8021807A0 (it) | 1980-05-06 |
| IL60008A (en) | 1983-05-15 |
| IL60008A0 (en) | 1980-07-31 |
| AU5812280A (en) | 1980-11-13 |
| FR2456092A1 (fr) | 1980-12-05 |
| SU999967A3 (ru) | 1983-02-23 |
| GB2049691A (en) | 1980-12-31 |
| DK198280A (da) | 1980-11-08 |
| AT372952B (de) | 1983-12-12 |
| JPS55153773A (en) | 1980-11-29 |
| ES8104248A1 (es) | 1981-04-01 |
| NL8002598A (nl) | 1980-11-11 |
| ATA242180A (de) | 1983-04-15 |
| SE8003394L (sv) | 1980-11-08 |
| HU179191B (en) | 1982-09-28 |
| DK148178C (da) | 1985-10-07 |
| IT1174668B (it) | 1987-07-01 |
| GB2049691B (en) | 1983-07-20 |
| ES491240A0 (es) | 1981-04-01 |
| BE883082A (fr) | 1980-11-03 |
| DK148178B (da) | 1985-04-22 |
| DE3017508A1 (de) | 1980-11-20 |
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| NUG | Patent has lapsed |
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