DE2103249A1 - Verfahren zur Herstellung von 2 Aryl 3 imino s tnazolo eckige Klam mer auf 4,3 alpha eckige Klammer zu 5 Methyl 7 hydroxy pynmidinen - Google Patents
Verfahren zur Herstellung von 2 Aryl 3 imino s tnazolo eckige Klam mer auf 4,3 alpha eckige Klammer zu 5 Methyl 7 hydroxy pynmidinenInfo
- Publication number
- DE2103249A1 DE2103249A1 DE19712103249 DE2103249A DE2103249A1 DE 2103249 A1 DE2103249 A1 DE 2103249A1 DE 19712103249 DE19712103249 DE 19712103249 DE 2103249 A DE2103249 A DE 2103249A DE 2103249 A1 DE2103249 A1 DE 2103249A1
- Authority
- DE
- Germany
- Prior art keywords
- aryl
- diamino
- square brackets
- diketene
- triazole
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 125000003118 aryl group Chemical group 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title 1
- 125000001841 imino group Chemical group [H]N=* 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QCYJCZJMOAWVPC-UHFFFAOYSA-N 1-phenyl-1,2,4-triazole-3,5-diamine Chemical compound N1=C(N)N=C(N)N1C1=CC=CC=C1 QCYJCZJMOAWVPC-UHFFFAOYSA-N 0.000 description 1
- NPNNLGXEAGTSRN-UHFFFAOYSA-N 9-bromo-10-(10-bromoanthracen-9-yl)anthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=C(C=CC=C2)C2=C(Br)C2=CC=CC=C12 NPNNLGXEAGTSRN-UHFFFAOYSA-N 0.000 description 1
- 241001640117 Callaeum Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 102100038803 Somatotropin Human genes 0.000 description 1
- 108050007673 Somatotropin Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- -1 for example Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH108470A CH524624A (de) | 1970-01-27 | 1970-01-27 | Verfahren zur Herstellung von 2-Aryl-3-imino-s-triazolo-(4,3-a)-5-Methyl-7-hydroxy-pyrimidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2103249A1 true DE2103249A1 (de) | 1971-08-26 |
Family
ID=4202076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712103249 Pending DE2103249A1 (de) | 1970-01-27 | 1971-01-25 | Verfahren zur Herstellung von 2 Aryl 3 imino s tnazolo eckige Klam mer auf 4,3 alpha eckige Klammer zu 5 Methyl 7 hydroxy pynmidinen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3758474A (2) |
| JP (1) | JPS4914757B1 (2) |
| CA (1) | CA924723A (2) |
| CH (1) | CH524624A (2) |
| DE (1) | DE2103249A1 (2) |
| FR (1) | FR2077040A5 (2) |
| GB (1) | GB1325664A (2) |
| NL (1) | NL7100815A (2) |
| PL (1) | PL81644B1 (2) |
| SU (1) | SU428604A3 (2) |
-
1970
- 1970-01-27 CH CH108470A patent/CH524624A/de not_active IP Right Cessation
- 1970-12-16 JP JP45111937A patent/JPS4914757B1/ja active Pending
-
1971
- 1971-01-12 SU SU1610651A patent/SU428604A3/ru active
- 1971-01-19 GB GB174571A patent/GB1325664A/en not_active Expired
- 1971-01-21 NL NL7100815A patent/NL7100815A/xx unknown
- 1971-01-22 CA CA103351A patent/CA924723A/en not_active Expired
- 1971-01-22 US US00108949A patent/US3758474A/en not_active Expired - Lifetime
- 1971-01-25 DE DE19712103249 patent/DE2103249A1/de active Pending
- 1971-01-26 PL PL1971145828A patent/PL81644B1/pl unknown
- 1971-01-27 FR FR7102656A patent/FR2077040A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3758474A (en) | 1973-09-11 |
| PL81644B1 (2) | 1975-08-30 |
| CA924723A (en) | 1973-04-17 |
| CH524624A (de) | 1972-06-30 |
| GB1325664A (en) | 1973-08-08 |
| SU428604A3 (ru) | 1974-05-15 |
| NL7100815A (2) | 1971-07-29 |
| JPS4914757B1 (2) | 1974-04-10 |
| FR2077040A5 (2) | 1971-10-15 |
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