DE1057125B - Verfahren zur Herstellung von 5-Arylsulfonamido-1,2,4-thiodiazolen - Google Patents
Verfahren zur Herstellung von 5-Arylsulfonamido-1,2,4-thiodiazolenInfo
- Publication number
- DE1057125B DE1057125B DEF24589A DEF0024589A DE1057125B DE 1057125 B DE1057125 B DE 1057125B DE F24589 A DEF24589 A DE F24589A DE F0024589 A DEF0024589 A DE F0024589A DE 1057125 B DE1057125 B DE 1057125B
- Authority
- DE
- Germany
- Prior art keywords
- thiodiazoles
- thiodiazole
- aryl
- acid
- preparation
- 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
- 239000002253 acid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical group CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- -1 des Thiodiazole radical Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- VMSZFGJMDPANBP-UHFFFAOYSA-N 3-ethyl-1,2,4-thiadiazol-5-amine Chemical compound CCC1=NSC(N)=N1 VMSZFGJMDPANBP-UHFFFAOYSA-N 0.000 description 1
- JDQDSEVNMTYMOC-UHFFFAOYSA-N 3-methylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1 JDQDSEVNMTYMOC-UHFFFAOYSA-N 0.000 description 1
- LTAJGPXOHCRTDH-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonylbutylurea Chemical compound NC(=O)NCCCCS(=O)(=O)C1=CC=C(N)C=C1 LTAJGPXOHCRTDH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24589A DE1057125B (de) | 1957-12-10 | 1957-12-10 | Verfahren zur Herstellung von 5-Arylsulfonamido-1,2,4-thiodiazolen |
| AT838858A AT208856B (de) | 1957-12-10 | 1958-12-03 | Verfahren zur Herstellung von neuen Sulfonamidverbindungen |
| DK451558AA DK93843C (da) | 1957-12-10 | 1958-12-09 | Fremgangsmåde til fremstilling af 5-alkylphenyl-1,2,4-thiodiazolsulfonamidforbindelser. |
| BE573715A BE573715A (fr) | 1957-12-10 | 1958-12-09 | Procédé de préparation de composés sulfonamidés. |
| NL234076A NL105698C (en:Method) | 1957-12-10 | 1958-12-10 | |
| US843907A US3010872A (en) | 1957-12-10 | 1959-09-30 | 5-arylsulfonamido-3-substituted 1, 2, 4-thiodiazole derivatives and their therapeutic use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24589A DE1057125B (de) | 1957-12-10 | 1957-12-10 | Verfahren zur Herstellung von 5-Arylsulfonamido-1,2,4-thiodiazolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1057125B true DE1057125B (de) | 1959-05-14 |
Family
ID=7091279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF24589A Pending DE1057125B (de) | 1957-12-10 | 1957-12-10 | Verfahren zur Herstellung von 5-Arylsulfonamido-1,2,4-thiodiazolen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3010872A (en:Method) |
| AT (1) | AT208856B (en:Method) |
| BE (1) | BE573715A (en:Method) |
| DE (1) | DE1057125B (en:Method) |
| DK (1) | DK93843C (en:Method) |
| NL (1) | NL105698C (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8071631B2 (en) * | 2006-08-16 | 2011-12-06 | The J. David Gladstone Institutes, A Testamentary Trust Established Under The Will Of J. David Gladstone | Small molecule inhibitors of kynurenine-3-monooxygenase |
| EP2054397B1 (en) | 2006-08-16 | 2015-10-07 | The J. David Gladstone Institutes, A Testamentary Trust Established under The Will of J. David Gladstone | Small molecule inhibitors of kynurenine-3-monooxygenase |
-
1957
- 1957-12-10 DE DEF24589A patent/DE1057125B/de active Pending
-
1958
- 1958-12-03 AT AT838858A patent/AT208856B/de active
- 1958-12-09 DK DK451558AA patent/DK93843C/da active
- 1958-12-09 BE BE573715A patent/BE573715A/fr unknown
- 1958-12-10 NL NL234076A patent/NL105698C/xx active
-
1959
- 1959-09-30 US US843907A patent/US3010872A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK93843C (da) | 1962-07-09 |
| AT208856B (de) | 1960-05-10 |
| NL105698C (en:Method) | 1963-08-15 |
| BE573715A (fr) | 1959-04-01 |
| US3010872A (en) | 1961-11-28 |
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