CH642636A5 - Verfahren zur herstellung von 6-n-substituierten 6-amino-3-pyridazinyl-hydrazinen. - Google Patents
Verfahren zur herstellung von 6-n-substituierten 6-amino-3-pyridazinyl-hydrazinen. Download PDFInfo
- Publication number
- CH642636A5 CH642636A5 CH351280A CH351280A CH642636A5 CH 642636 A5 CH642636 A5 CH 642636A5 CH 351280 A CH351280 A CH 351280A CH 351280 A CH351280 A CH 351280A CH 642636 A5 CH642636 A5 CH 642636A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridazinyl
- hydrazine
- substituted
- yield
- general formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 5
- UCLVUFDXMAWDIA-UHFFFAOYSA-N 6-hydrazinylpyridazin-3-amine Chemical class NNC1=CC=C(N)N=N1 UCLVUFDXMAWDIA-UHFFFAOYSA-N 0.000 title description 4
- -1 nitro, methoxy Chemical group 0.000 description 47
- 238000000034 method Methods 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- 239000007858 starting material 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
- 239000002253 acid Substances 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- FXYQRYGWWZKUFV-UHFFFAOYSA-N (6-chloropyridazin-3-yl)hydrazine Chemical compound NNC1=CC=C(Cl)N=N1 FXYQRYGWWZKUFV-UHFFFAOYSA-N 0.000 description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 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 compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000723346 Cinnamomum camphora Species 0.000 description 4
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 229930008380 camphor Natural products 0.000 description 4
- 229960000846 camphor Drugs 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000003960 organic solvent 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
- PHBNMZNMGUQCFK-UHFFFAOYSA-N (6-morpholin-4-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1N1CCOCC1 PHBNMZNMGUQCFK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- 150000003935 benzaldehydes Chemical class 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- DSSYKIVIOFKYAU-OIBJUYFYSA-N (S)-camphor Chemical compound C1C[C@]2(C)C(=O)C[C@H]1C2(C)C DSSYKIVIOFKYAU-OIBJUYFYSA-N 0.000 description 2
- DTXVKPOKPFWSFF-UHFFFAOYSA-N 3(S)-hydroxy-13-cis-eicosenoyl-CoA Chemical group NC1=CC=C(Cl)N=N1 DTXVKPOKPFWSFF-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
- 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
- YRACHDVMKITFAZ-UHFFFAOYSA-N [1,2,4]triazolo[4,3-b]pyridazine Chemical class C1=CC=NN2C=NN=C21 YRACHDVMKITFAZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 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
- 230000001077 hypotensive effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 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 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- SXDDPTLSQSRWTI-UHFFFAOYSA-N (6-pyrrolidin-1-ylpyridazin-3-yl)hydrazine;dihydrochloride Chemical compound Cl.Cl.N1=NC(NN)=CC=C1N1CCCC1 SXDDPTLSQSRWTI-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
- ZEJHFYVAMIWPTN-UHFFFAOYSA-N 1-[(6-hydrazinylpyridazin-3-yl)-methylamino]propan-2-ol;hydron;dichloride Chemical compound Cl.Cl.CC(O)CN(C)C1=CC=C(NN)N=N1 ZEJHFYVAMIWPTN-UHFFFAOYSA-N 0.000 description 1
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 1
- QWBYZZJOPXNTTQ-UHFFFAOYSA-N 3-N-(benzylideneamino)pyridazine-3,6-diamine Chemical class NC1=CC=C(N=N1)NN=CC1=CC=CC=C1 QWBYZZJOPXNTTQ-UHFFFAOYSA-N 0.000 description 1
- CAZDNMWZZXLBSI-UHFFFAOYSA-N 3-chloro-6-methylsulfanylpyridazine Chemical compound CSC1=CC=C(Cl)N=N1 CAZDNMWZZXLBSI-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
- ATYRSERUSOMCNR-UHFFFAOYSA-N 6-chloro-n-[(3-nitrophenyl)methylideneamino]pyridazin-3-amine Chemical compound [O-][N+](=O)C1=CC=CC(C=NNC=2N=NC(Cl)=CC=2)=C1 ATYRSERUSOMCNR-UHFFFAOYSA-N 0.000 description 1
- CKFSOHCIIFDNID-UHFFFAOYSA-N 6-chloro-n-[(4-methoxyphenyl)methylideneamino]pyridazin-3-amine Chemical class C1=CC(OC)=CC=C1C=NNC1=CC=C(Cl)N=N1 CKFSOHCIIFDNID-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
- ZDISBPCSJYBKFJ-UHFFFAOYSA-N 6-methylsulfanylpyridazin-3-amine Chemical class CSC1=CC=C(N)N=N1 ZDISBPCSJYBKFJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 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 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical group [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning 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
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WTIUKIUHXNYLGG-UHFFFAOYSA-N n-(benzylideneamino)-6-morpholin-4-ylpyridazin-3-amine Chemical compound C1COCCN1C(N=N1)=CC=C1NN=CC1=CC=CC=C1 WTIUKIUHXNYLGG-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
- 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 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- YTRGNBTVTHPFJM-UHFFFAOYSA-N pyridazin-3-ylhydrazine Chemical class NNC1=CC=CN=N1 YTRGNBTVTHPFJM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation 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
- 238000003786 synthesis reaction 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 (1)
| Publication Number | Publication Date |
|---|---|
| CH642636A5 true CH642636A5 (de) | 1984-04-30 |
Family
ID=10996892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH351280A CH642636A5 (de) | 1979-05-07 | 1980-05-06 | Verfahren zur herstellung von 6-n-substituierten 6-amino-3-pyridazinyl-hydrazinen. |
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 |
| 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 |
| SE435505B (sv) | 1984-10-01 |
| BE883082A (fr) | 1980-11-03 |
| DK148178B (da) | 1985-04-22 |
| DE3017508A1 (de) | 1980-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |