DE2253615A1 - Verfahren zur herstellung von neuen triazenen-verbindungen - Google Patents
Verfahren zur herstellung von neuen triazenen-verbindungenInfo
- Publication number
- DE2253615A1 DE2253615A1 DE19722253615 DE2253615A DE2253615A1 DE 2253615 A1 DE2253615 A1 DE 2253615A1 DE 19722253615 DE19722253615 DE 19722253615 DE 2253615 A DE2253615 A DE 2253615A DE 2253615 A1 DE2253615 A1 DE 2253615A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- general formula
- carbon atoms
- amidine
- formula
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000001409 amidines Chemical class 0.000 claims description 9
- -1 methoxy, butoxy Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000001476 alcoholic effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000004654 triazenes Chemical class 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- SGZTZYQJFPLMQG-UHFFFAOYSA-N n'-butylethanimidamide Chemical compound CCCCNC(C)=N SGZTZYQJFPLMQG-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IKZLMSPFYNDYIL-UHFFFAOYSA-N (5E)-5-diazoimidazole-4-carboxamide Chemical compound NC(=O)C1=NC=NC1=[N+]=[N-] IKZLMSPFYNDYIL-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- YWOITFUKFOYODT-UHFFFAOYSA-N methanol;sodium Chemical compound [Na].OC YWOITFUKFOYODT-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
- C07D231/38—Nitrogen atoms
-
- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
-
- 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/3924—Heterocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001190 HU164584B (enExample) | 1971-11-19 | 1971-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2253615A1 true DE2253615A1 (de) | 1973-05-24 |
Family
ID=10994423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722253615 Pending DE2253615A1 (de) | 1971-11-19 | 1972-11-02 | Verfahren zur herstellung von neuen triazenen-verbindungen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4947365A (enExample) |
| AT (1) | AT321908B (enExample) |
| CH (1) | CH582671A5 (enExample) |
| DE (1) | DE2253615A1 (enExample) |
| FR (1) | FR2160448B1 (enExample) |
| GB (1) | GB1403050A (enExample) |
| HU (1) | HU164584B (enExample) |
| SU (1) | SU455537A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1000525B (de) * | 1954-05-03 | 1957-01-10 | Licentia Gmbh | Xenon-Farbabmusterungsleuchte |
| CA3075664C (en) * | 2017-11-16 | 2020-12-29 | Montdorex Inc. | Mono- and di-amidine endo-exonuclease inhibitors and methods for inhibiting endo-exonuclease activity |
| CN114044757B (zh) * | 2021-08-30 | 2023-06-09 | 浙江大学 | 三氮唑-4-(n-取代甲酰胺)-5-三氮烯类化合物及其制备方法和应用 |
-
1971
- 1971-11-19 HU HUCI001190 patent/HU164584B/hu unknown
-
1972
- 1972-11-02 DE DE19722253615 patent/DE2253615A1/de active Pending
- 1972-11-06 AT AT938772A patent/AT321908B/de not_active IP Right Cessation
- 1972-11-08 GB GB5154272A patent/GB1403050A/en not_active Expired
- 1972-11-14 FR FR7240355A patent/FR2160448B1/fr not_active Expired
- 1972-11-17 CH CH1678272A patent/CH582671A5/xx not_active IP Right Cessation
- 1972-11-17 SU SU1847751A patent/SU455537A3/ru active
- 1972-11-17 JP JP47114887A patent/JPS4947365A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2160448A1 (enExample) | 1973-06-29 |
| FR2160448B1 (enExample) | 1975-11-28 |
| SU455537A3 (ru) | 1974-12-30 |
| GB1403050A (en) | 1975-08-13 |
| JPS4947365A (enExample) | 1974-05-08 |
| HU164584B (enExample) | 1974-03-28 |
| CH582671A5 (enExample) | 1976-12-15 |
| AT321908B (de) | 1975-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1670536B2 (de) | Neue 2-Anilino-5-acylamino-pyrimidlne | |
| CH534687A (de) | Verfahren zur Herstellung von Derivaten des 2-Oxo-1,2-dihydro-chinolins | |
| DE1445878A1 (de) | Verfahren zur Herstellung von Benzodiazepin-Derivaten | |
| DE1906401A1 (de) | Verfahren zur Herstellung von 4-Acyloxy-azetidin-2-onen | |
| EP0534904A1 (de) | Imidazolylmethyl-Pyridine | |
| US2677686A (en) | Pyrazine derivatives and method of preparing the same | |
| US2717268A (en) | Process for preparing phenyldichloro-acetamidopropanediols | |
| DE1470070B1 (de) | Verfahren zur Herstellung von Benzimidazolderivaten | |
| DE881194C (de) | Verfahren zur Herstellung von Thiophosphorsaeureestern der 3-Halogenoxycumarine | |
| DE870418C (de) | Verfahren zur Herstellung von Pyrazolinverbindungen | |
| DE1595894A1 (de) | Neue 1,5-Diazabicyclo[3,3,0]octan-2,6-dione | |
| DE2417063C2 (de) | Tricyclische Sulfoximid-Derivate | |
| DE1172671B (de) | Verfahren zur Herstellung von 17ª-Hydroxy-androstan-(3, 2-c)-pyrazol oder eines 17ª-Hydroxy-17ª-niederes-Alkyl-androstan-(3, 2-c)-pyrazols | |
| DE2024299A1 (de) | Neue Sulfonamide, Verfahren zu ihrer Herstellung und ihre Verwendung in einem pharmazeutischen Präparat | |
| US2460747A (en) | 5-alkoxy-alkyl, 5-cyclohexyl hydantoins | |
| DE832891C (de) | Verfahren zur Herstellung von Thiosemicarbaziden | |
| DE1445873A1 (de) | Verfahren zur Herstellung von Benzodiazepin-Derivaten | |
| DE872912C (de) | Verfahren zum Sensibilisieren photographischer Emulsionen | |
| DE2012943A1 (de) | Neue Triazol-Derivate und Verfahren zur Herstellung derselben | |
| DE913287C (de) | Verfahren zur Herstellung von 4-Amino-5-keto-1,3,4,5-tetrahydro-benz-(cd)-indol und von Derivaten desselben | |
| US2931813A (en) | 1-alkenyl-3-alkyl-5-sulfonamido-6-aminouracil | |
| DE1545702A1 (de) | Verfahren zur Herstellung von Dihydro-3,4[2H]-Benzothiazin-1,4-on-3-Verbindungen | |
| DE936686C (de) | Verfahren zur Herstellung von 2-Amino-5-(2'-oxyaethyl)-oxazol-(1, 3) | |
| DE839349C (de) | Verfahren zur Herstellung von Thiosemicarbaziden | |
| DE1470070C (de) | Verfahren zur Herstellung von Benzimidazolderivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |