DE2160674C3 - Verfahren zur Herstellung von 4(5)-Aminoimidazol-5(4)-carboxamid aus 4(5)-Aminoimidazol-5(4)-carbonitril - Google Patents
Verfahren zur Herstellung von 4(5)-Aminoimidazol-5(4)-carboxamid aus 4(5)-Aminoimidazol-5(4)-carbonitrilInfo
- Publication number
- DE2160674C3 DE2160674C3 DE19712160674 DE2160674A DE2160674C3 DE 2160674 C3 DE2160674 C3 DE 2160674C3 DE 19712160674 DE19712160674 DE 19712160674 DE 2160674 A DE2160674 A DE 2160674A DE 2160674 C3 DE2160674 C3 DE 2160674C3
- Authority
- DE
- Germany
- Prior art keywords
- aminoimidazole
- aica
- reaction
- aicn
- carbonitrile
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 28
- DVNYTAVYBRSTGK-UHFFFAOYSA-N Aminoimidazole carboxamide Natural products NC(=O)C=1N=CNC=1N DVNYTAVYBRSTGK-UHFFFAOYSA-N 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 8
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 239000000047 product Substances 0.000 description 18
- MXCUYSMIELHIQL-UHFFFAOYSA-N (4-carbamoyl-1h-imidazol-5-yl)azanium;chloride Chemical compound Cl.NC(=O)C=1NC=NC=1N MXCUYSMIELHIQL-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 210000005097 arteria cerebelosa anteroinferior Anatomy 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- FQZSGFVLPVDJOR-UHFFFAOYSA-N 2,3-diamino-3-iminopropanamide;dihydrochloride Chemical compound Cl.Cl.NC(=N)C(N)C(N)=O FQZSGFVLPVDJOR-UHFFFAOYSA-N 0.000 description 1
- DUTJFFGOOSJANZ-UHFFFAOYSA-N 2-phenyldiazenylpropanediimidamide Chemical compound NC(=N)C(C(N)=N)N=NC1=CC=CC=C1 DUTJFFGOOSJANZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- YJHHUXIIKAYKJJ-UHFFFAOYSA-N 4-nitro-1h-imidazole-5-carboxamide Chemical compound NC(=O)C=1NC=NC=1[N+]([O-])=O YJHHUXIIKAYKJJ-UHFFFAOYSA-N 0.000 description 1
- 238000007167 Hofmann rearrangement reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- -1 purine compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- 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
- C07D233/66—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 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/36—Sulfur atom
- C07D473/38—Sulfur atom attached in position 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10857870A JPS5417758B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-09 | 1970-12-09 | |
| JP10857970A JPS515000B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-09 | 1970-12-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2160674A1 DE2160674A1 (de) | 1972-06-29 |
| DE2160674B2 DE2160674B2 (de) | 1977-12-29 |
| DE2160674C3 true DE2160674C3 (de) | 1978-08-24 |
Family
ID=26448423
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712166506 Ceased DE2166506A1 (de) | 1970-12-09 | 1971-12-07 | Verfahren zur herstellung von purinverbindungen |
| DE19712160674 Expired DE2160674C3 (de) | 1970-12-09 | 1971-12-07 | Verfahren zur Herstellung von 4(5)-Aminoimidazol-5(4)-carboxamid aus 4(5)-Aminoimidazol-5(4)-carbonitril |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712166506 Ceased DE2166506A1 (de) | 1970-12-09 | 1971-12-07 | Verfahren zur herstellung von purinverbindungen |
Country Status (6)
-
1971
- 1971-11-29 GB GB5540771A patent/GB1377388A/en not_active Expired
- 1971-12-07 DE DE19712166506 patent/DE2166506A1/de not_active Ceased
- 1971-12-07 DE DE19712160674 patent/DE2160674C3/de not_active Expired
- 1971-12-08 NL NL7116866A patent/NL7116866A/xx unknown
- 1971-12-08 CH CH86375A patent/CH574415A5/xx not_active IP Right Cessation
- 1971-12-08 CH CH1789271A patent/CH584713A5/xx not_active IP Right Cessation
- 1971-12-09 IT IT5462871A patent/IT986009B/it active
- 1971-12-09 FR FR7144299A patent/FR2117605A5/fr not_active Expired
-
1976
- 1976-06-30 CH CH835676A patent/CH584712A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7116866A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-06-13 |
| IT986009B (it) | 1975-01-10 |
| DE2160674A1 (de) | 1972-06-29 |
| DE2166506A1 (de) | 1974-09-05 |
| DE2160674B2 (de) | 1977-12-29 |
| CH574415A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-04-15 |
| GB1377388A (en) | 1974-12-11 |
| CH584712A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-15 |
| FR2117605A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-07-21 |
| CH584713A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |