NO770014L - Fremgangsm}te til fremstilling av hydroazinderivater. - Google Patents

Fremgangsm}te til fremstilling av hydroazinderivater.

Info

Publication number: NO770014L
Authority: NO; Norway
Prior art keywords: hydrazine; pharmaceutically acceptable; addition salts; acid addition; amidino
Prior art date: 1976-01-07

Application number

NO770014A

Other languages

English (en)

Norwegian (no)

Inventor

Jean-Marie Teulon

Bernard Schweisguth

Jean-Claude Cognacq

Original Assignee

Hexachimie

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-01-07

Filing date

1977-01-04

Publication date

1977-07-08

1977-01-04 Application filed by Hexachimie filed Critical Hexachimie

1977-07-08 Publication of NO770014L publication Critical patent/NO770014L/no

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 20
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
230000007935 neutral effect Effects 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 9
VKGQPUZNCZPZKI-UHFFFAOYSA-N (diaminomethylideneamino)azanium;sulfate Chemical compound NN=C(N)N.NN=C(N)N.OS(O)(=O)=O VKGQPUZNCZPZKI-UHFFFAOYSA-N 0.000 claims description 8
150000002429 hydrazines Chemical class 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
-1 benzylthio Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
DKUKXOSTGVRFAA-UHFFFAOYSA-N 2-[(2-chloro-2H-pyridin-3-ylidene)amino]guanidine Chemical compound NC(=N)NN=C1C=CC=NC1Cl DKUKXOSTGVRFAA-UHFFFAOYSA-N 0.000 claims description 3
CWLHRLIXHQMPDP-UHFFFAOYSA-N 4,5-dihydroimidazol-1-ylhydrazine;hydrobromide Chemical compound Br.NNN1CCN=C1 CWLHRLIXHQMPDP-UHFFFAOYSA-N 0.000 claims description 3
150000001299 aldehydes Chemical class 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000004414 alkyl thio group Chemical group 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 description 2
238000009835 boiling Methods 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
DEDUGEBBGTZSBF-UHFFFAOYSA-N 2-[(1,3,6-trimethyl-2-oxo-4h-benzimidazol-5-ylidene)amino]guanidine Chemical compound C1C(=NNC(N)=N)C(C)=CC2=C1N(C)C(=O)N2C DEDUGEBBGTZSBF-UHFFFAOYSA-N 0.000 claims 1
LFCMKGYNGXSZHI-UHFFFAOYSA-N 2-aminoguanidine;dihydrochloride Chemical compound Cl.Cl.NNC(N)=N LFCMKGYNGXSZHI-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
PEERMPFPCWSJLC-UHFFFAOYSA-N 2-prop-2-ynoxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OCC#C PEERMPFPCWSJLC-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
XLONNWGCEFSFTN-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen sulfate Chemical compound NC(N)=N[NH3+].OS([O-])(=O)=O XLONNWGCEFSFTN-UHFFFAOYSA-N 0.000 description 2
BXCJDECTRRMSCV-UHFFFAOYSA-N 2-prop-2-enoxybenzaldehyde Chemical compound C=CCOC1=CC=CC=C1C=O BXCJDECTRRMSCV-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XWRUIANPZDHTHJ-UHFFFAOYSA-N 1-(2-prop-2-ynoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC#C XWRUIANPZDHTHJ-UHFFFAOYSA-N 0.000 description 1
LGDVLBMOPJJUOX-UHFFFAOYSA-N 2-[(1,3-dimethyl-2-oxo-4h-benzimidazol-5-ylidene)amino]guanidine Chemical compound C1C(=NNC(N)=N)C=CC2=C1N(C)C(=O)N2C LGDVLBMOPJJUOX-UHFFFAOYSA-N 0.000 description 1
KIOJWHFYSREHJK-UHFFFAOYSA-N 2-[(2-benzylsulfanyl-2H-pyridin-3-ylidene)amino]guanidine dihydrochloride Chemical compound Cl.Cl.NC(=N)NN=C1C=CC=NC1SCC1=CC=CC=C1 KIOJWHFYSREHJK-UHFFFAOYSA-N 0.000 description 1
ZJBTXAUVOYMVOR-UHFFFAOYSA-N 2-[(2-cyclopropylphenyl)methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=CC=C1C1CC1 ZJBTXAUVOYMVOR-UHFFFAOYSA-N 0.000 description 1
CRIOBLFUSRSNFJ-UHFFFAOYSA-N 2-benzylpyridine-3-carbothialdehyde Chemical compound S=CC1=CC=CN=C1CC1=CC=CC=C1 CRIOBLFUSRSNFJ-UHFFFAOYSA-N 0.000 description 1
KHPAGGHFIDLUMB-UHFFFAOYSA-N 2-chloropyridine-3-carbaldehyde Chemical compound ClC1=NC=CC=C1C=O KHPAGGHFIDLUMB-UHFFFAOYSA-N 0.000 description 1
ZVDXHSUCDWVQEY-UHFFFAOYSA-N 2-cyclopropylbenzaldehyde Chemical compound O=CC1=CC=CC=C1C1CC1 ZVDXHSUCDWVQEY-UHFFFAOYSA-N 0.000 description 1
PZCVDBMEAFEAHK-UHFFFAOYSA-N 2-methylpyridine-3-carbothialdehyde Chemical compound CC1=NC=CC=C1C=S PZCVDBMEAFEAHK-UHFFFAOYSA-N 0.000 description 1
CUDNMHPROXHRNR-UHFFFAOYSA-N 4,5-dihydroimidazol-1-ylhydrazine Chemical compound NNN1CCN=C1 CUDNMHPROXHRNR-UHFFFAOYSA-N 0.000 description 1
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
SOOZKZVZLZIMGK-UHFFFAOYSA-N 4-methoxy-1,3-dimethylimidazol-2-one Chemical compound COC1=CN(C)C(=O)N1C SOOZKZVZLZIMGK-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 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
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000004873 systolic arterial blood pressure Effects 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO770014A 1976-01-07 1977-01-04 Fremgangsm}te til fremstilling av hydroazinderivater. NO770014L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB562/76A GB1550401A (en)	1976-01-07	1976-01-07	Hydrazine derivatives their preparation and their use

Publications (1)

Publication Number	Publication Date
NO770014L true NO770014L (no)	1977-07-08

Family

ID=9706555

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO770014A NO770014L (no)	1976-01-07	1977-01-04	Fremgangsm}te til fremstilling av hydroazinderivater.

Country Status (19)

Country	Link
US (1)	US4109008A (da)
JP (1)	JPS5285131A (da)
AR (1)	AR210781A1 (da)
AT (1)	AT350584B (da)
AU (1)	AU2105877A (da)
BE (1)	BE850089A (da)
DD (1)	DD128401A5 (da)
DE (1)	DE2700561A1 (da)
DK (1)	DK3177A (da)
ES (1)	ES454830A1 (da)
FR (1)	FR2337550A1 (da)
GB (1)	GB1550401A (da)
HU (1)	HU172023B (da)
NL (1)	NL7700152A (da)
NO (1)	NO770014L (da)
PT (1)	PT66029B (da)
SE (1)	SE7614568L (da)
SU (1)	SU607547A3 (da)
ZA (1)	ZA767698B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES8302665A1 (es) *	1981-04-06	1983-02-16	Hexachimie	"procedimiento de preparacion de nuevos derivados de la hidrazina, utiles como fungicidas y bactericidas".
FR2549049B1 (fr) *	1983-07-13	1986-06-20	Chauvin Blache Lab	Nouvelles amidines, leur procede de preparation et leur application therapeutique
RU2137750C1 (ru) *	1998-05-19	1999-09-20	Институт органического синтеза Уральского отделения РАН	Замещенные ди(формиларил)полиэфиры, или их координационные соединения, или их фармацевтически приемлемые аддитивные соли, способ их получения и фармацевтическая композиция на их основе
GB0019357D0 (en) *	2000-08-07	2000-09-27	Melacure Therapeutics Ab	Novel phenyl guanidines
GB0624987D0 (en) *	2006-12-14	2007-01-24	Acure Pharma Ab	Novel aminoguanidines as melanocortin receptor ligands
EP3280404B1 (en)	2015-04-08	2021-10-06	United Kingdom Research and Innovation	Methods for selecting phosphatase selective and non-selective phosphatase inhibitors

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4024125A (en) *	1973-01-19	1977-05-17	Hoechst Aktiengesellschaft	Dis-azo pigments deriving from bis-diazotized diamino-2-phenyl-benzazolones
USRE29358E (en)	1973-03-01	1977-08-16	American Cyanamid Company	1,5-Bis substituted-1,4-pentadien-3-one substituted amidino hydrazone salts and method of preparing the same
CH610000A5 (da) *	1973-06-06	1979-03-30	Hoechst Ag
CH591540A5 (da) *	1974-03-12	1977-09-30	Ciba Geigy Ag

1976
- 1976-01-07 GB GB562/76A patent/GB1550401A/en not_active Expired
- 1976-12-22 FR FR7638736A patent/FR2337550A1/fr not_active Withdrawn
- 1976-12-27 SE SE7614568A patent/SE7614568L/xx unknown
- 1976-12-29 US US05/755,194 patent/US4109008A/en not_active Expired - Lifetime
- 1976-12-30 ZA ZA767698A patent/ZA767698B/xx unknown
- 1976-12-30 AT AT980776A patent/AT350584B/de not_active IP Right Cessation
1977
- 1977-01-04 DD DD7700196810A patent/DD128401A5/xx unknown
- 1977-01-04 NO NO770014A patent/NO770014L/no unknown
- 1977-01-04 PT PT66029A patent/PT66029B/pt unknown
- 1977-01-05 ES ES454830A patent/ES454830A1/es not_active Expired
- 1977-01-05 AU AU21058/77A patent/AU2105877A/en not_active Expired
- 1977-01-05 DK DK3177A patent/DK3177A/da unknown
- 1977-01-05 BE BE2055568A patent/BE850089A/xx unknown
- 1977-01-06 HU HU77HE00000725A patent/HU172023B/hu unknown
- 1977-01-06 SU SU772435953A patent/SU607547A3/ru active
- 1977-01-07 JP JP71977A patent/JPS5285131A/ja active Pending
- 1977-01-07 NL NL7700152A patent/NL7700152A/xx not_active Application Discontinuation
- 1977-01-07 DE DE19772700561 patent/DE2700561A1/de active Pending
- 1977-01-08 AR AR266095A patent/AR210781A1/es active

Also Published As

Publication number	Publication date
ATA980776A (de)	1978-11-15
ZA767698B (en)	1977-11-30
DD128401A5 (de)	1977-11-16
NL7700152A (nl)	1977-07-11
BE850089A (fr)	1977-05-02
AU2105877A (en)	1978-07-13
PT66029A (fr)	1977-02-01
JPS5285131A (en)	1977-07-15
US4109008A (en)	1978-08-22
ES454830A1 (es)	1978-01-01
HU172023B (hu)	1978-05-28
GB1550401A (en)	1979-08-15
FR2337550A1 (fr)	1977-08-05
SU607547A3 (ru)	1978-05-15
SE7614568L (sv)	1977-07-08
PT66029B (fr)	1978-06-19
DE2700561A1 (de)	1977-07-14
DK3177A (da)	1977-07-08
AR210781A1 (es)	1977-09-15
AT350584B (de)	1979-06-11

Publication	Publication Date	Title
NO152048B (no)	1985-04-15	Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 5h-2,3-benzodiazepinderivater
SU1153829A3 (ru)	1985-04-30	Способ получени 2-гуанидино-4-имидазотиазолов или их фармацевтически приемлемых аддитивных солей кислот
NO157175B (no)	1987-10-26	Analogifremgangsmaate ved fremstilling av terapeutisk aktive aroylimidazoloner.
EP0198456A2 (en)	1986-10-22	1,7-Naphthyridine derivatives and medicinal preparations containing same
PL119501B1 (en)	1982-01-30	Process for manufacturing novel,condensed pyrimidine derivatives pirimidina
NO782108L (no)	1978-12-19	Nye hexahydropyrimidiner, fremgangsmaate til deres fremstilling og legemidler som inneholder disse forbindelser
US4435396A (en)	1984-03-06	Antiulcer 2-guanidino-4-(2-substituted-amino-4-imidazolyl)thiazoles and process therefor
NO770014L (no)	1977-07-08	Fremgangsm}te til fremstilling av hydroazinderivater.
GB1568398A (en)	1980-05-29	Triazolo pyridazine derivatives
JPH0377867A (ja)	1991-04-03	新規オキサゾロピリジン誘導体
NO144928B (no)	1981-08-31	Analogifremgangsmaate for fremstilling av fysiologisk aktive zantinderivater
EP0074229B1 (en)	1986-04-09	Triazole gastric anti-secretory agents
US4025508A (en)	1977-05-24	6-(Trifluoromethyl)-benzothiadiazines
US4808727A (en)	1989-02-28	Imidazolium hydrogen carbonates
SU1217258A3 (ru)	1986-03-07	Способ получени производных 2-гуанидино-4-гетероарилтиазола или их фармацевтически приемлемых кислотно-аддитивных солей
US3467662A (en)	1969-09-16	1-para-chlorophenyl-3-hydrazino - 1,5,6,7,8,8a-hexahydroimidazo(1,5-a)pyridine and process for its preparation
FI69842C (fi)	1986-05-26	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3-amino-5-(4-pyridyl)-1,2,4-triazolbaser och farmaceutisktgodtagbara syraadditionssalter daerav
US4093627A (en)	1978-06-06	3-[(4-Chromanylidene)amino]-2-oxazolidinones
US3954984A (en)	1976-05-04	Triazolocycloalkylthiadiazine derivatives
US4018793A (en)	1977-04-19	Benzo (b) thiophene derivatives
NO143904B (no)	1981-01-26	Analogifremgangsmaate til fremstilling av terapeutisk virksomme substituerte triazoler
US4056526A (en)	1977-11-01	Benzo(b)thiophene derivatives
US3984560A (en)	1976-10-05	Composition for and method of treating disease caused by protozon
NO762124L (da)	1977-01-11
US3609155A (en)	1971-09-28	1-para-chlorophenyl-1,5,6,7,8,8{11 -hexahydroimidazo{8 1,5-{11 {9 pyridines and intermediates therefor