DE1193952B - Verfahren zur Herstellung von Benzol-sulfonamidopyrimidinen - Google Patents
Verfahren zur Herstellung von Benzol-sulfonamidopyrimidinenInfo
- Publication number
- DE1193952B DE1193952B DEF33151A DEF0033151A DE1193952B DE 1193952 B DE1193952 B DE 1193952B DE F33151 A DEF33151 A DE F33151A DE F0033151 A DEF0033151 A DE F0033151A DE 1193952 B DE1193952 B DE 1193952B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compound
- preparation
- methyl
- acetylpyrimidine
- 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 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- LWZQQJIAMSDELT-UHFFFAOYSA-N 1-(2-amino-4-methylpyrimidin-5-yl)ethanone Chemical compound CC(=O)C1=CN=C(N)N=C1C LWZQQJIAMSDELT-UHFFFAOYSA-N 0.000 claims description 4
- HLBLNLYCFFWMFF-UHFFFAOYSA-N n-pyrimidin-2-ylbenzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NC1=NC=CC=N1 HLBLNLYCFFWMFF-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- COTYNDRSENVEFI-UHFFFAOYSA-N 1-pyrimidin-5-ylethanone Chemical compound CC(=O)C1=CN=CN=C1 COTYNDRSENVEFI-UHFFFAOYSA-N 0.000 description 2
- YMXFYAAVYBVOKE-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonylguanidine Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=N)C=C1 YMXFYAAVYBVOKE-UHFFFAOYSA-N 0.000 description 2
- -1 4-methylbenzenesulfonyl Chemical group 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ULLKFRGCRYFTHF-UHFFFAOYSA-N 1-(4-methylpyrimidin-5-yl)ethanone Chemical compound CC(=O)C1=CN=CN=C1C ULLKFRGCRYFTHF-UHFFFAOYSA-N 0.000 description 1
- ZIRLDYOJRFPDFO-UHFFFAOYSA-N 1-butyl-1-(4-methylphenyl)sulfonylurea Chemical compound CCCCN(C(N)=O)S(=O)(=O)C1=CC=C(C)C=C1 ZIRLDYOJRFPDFO-UHFFFAOYSA-N 0.000 description 1
- BRSRNTJGTDYRFT-UHFFFAOYSA-N 2-(benzenesulfonyl)guanidine Chemical compound NC(N)=NS(=O)(=O)C1=CC=CC=C1 BRSRNTJGTDYRFT-UHFFFAOYSA-N 0.000 description 1
- FIFOCEFOCMXMKA-UHFFFAOYSA-N 6-ethoxyhex-5-ene-2,4-dione Chemical compound CCOC=CC(=O)CC(C)=O FIFOCEFOCMXMKA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- RYLHMXPGTMYTTF-UHFFFAOYSA-N acetyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)=O RYLHMXPGTMYTTF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
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)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE622086D BE622086A (en, 2012) | 1961-01-26 | ||
| BE622085D BE622085A (en, 2012) | 1961-01-26 | ||
| DEF33151A DE1193952B (de) | 1961-01-26 | 1961-02-07 | Verfahren zur Herstellung von Benzol-sulfonamidopyrimidinen |
| CH1135966A CH421120A (de) | 1961-01-26 | 1962-01-16 | Verfahren zur Herstellung von Sulfapyrimidinen |
| CH52062A CH420168A (de) | 1961-01-26 | 1962-01-16 | Verfahren zur Herstellung von Sulfapyrimidinen |
| US168232A US3180866A (en) | 1961-01-26 | 1962-01-23 | Substituted sulfapyrimidine derivatives |
| FR885925A FR1492756A (fr) | 1961-01-26 | 1962-01-25 | Procédé de fabrication de sulfapyrimidines |
| GB3103/62A GB939608A (en) | 1961-01-26 | 1962-01-26 | New sulphapyrimidines |
| FR887299A FR1492757A (fr) | 1961-01-26 | 1962-02-07 | Procédé de production de sulfapyrimidines |
| FR914836A FR2753M (fr) | 1961-01-26 | 1962-11-08 | Médicament a base de 2-(benzenesulfonyl)-amino-5-phénylpyrimidine pour réduire le taux de la glycémie. |
| FR914837A FR2253M (fr) | 1961-01-26 | 1962-11-08 | Médicament a base de 2-(benzenesulfonyl)-amino-4-méhtyl-5-acéthylpyrimidine pour réduire le taux de la glycémie. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF33067A DE1147948B (de) | 1961-01-26 | 1961-01-26 | Verfahren zur Herstellung von Benzolsulfonamidopyrimidinen |
| DEF33151A DE1193952B (de) | 1961-01-26 | 1961-02-07 | Verfahren zur Herstellung von Benzol-sulfonamidopyrimidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1193952B true DE1193952B (de) | 1965-06-03 |
Family
ID=25974885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF33151A Pending DE1193952B (de) | 1961-01-26 | 1961-02-07 | Verfahren zur Herstellung von Benzol-sulfonamidopyrimidinen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3180866A (en, 2012) |
| BE (2) | BE622086A (en, 2012) |
| CH (2) | CH420168A (en, 2012) |
| DE (1) | DE1193952B (en, 2012) |
| FR (2) | FR2753M (en, 2012) |
| GB (1) | GB939608A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3694436A (en) * | 1970-03-02 | 1972-09-26 | Toyama Chemical Co Ltd | Substituted 2-(benzenesulfonamido)-pyrimidines |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1545944A1 (de) * | 1964-06-19 | 1969-12-11 | Hoffmann La Roche | Verfahren zur Herstellung von neuen Sulfonamiden der Pyrimidinreihe |
| US3293259A (en) * | 1965-08-13 | 1966-12-20 | American Home Prod | Certain 1-arylsulfonyl-1, 2, 4-triazoles |
| DE1670168C3 (de) * | 1966-11-29 | 1975-04-10 | Boehringer Mannheim Gmbh, 6800 Mannheim | 2-Benzolsulfonamido-4-methyl-5alkyl-pyrimidine und Verfahren zu ihrer Herstellung |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE933340C (de) * | 1939-11-24 | 1955-09-22 | Schering Ag | Verfahren zur Herstellung von therapeutisch wertvollen Mitteln der p-Aminobenzolsulfonamid-Reihe |
| DE1027674B (de) | 1944-12-01 | 1958-04-10 | Schering Ag | Verfahren zur Herstellung von Sulfonamiden |
| DE975041C (de) * | 1941-07-25 | 1961-07-20 | Ici Ltd | Verfahren zur Herstellung von Sulfonamidderivaten des Pyrimidins |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055899A (en) * | 1962-09-25 | N-pyrazinyl-benzkne sulfonamides | ||
| BE447992A (en, 2012) * | 1942-01-30 | |||
| US2494524A (en) * | 1943-01-12 | 1950-01-10 | Sharp & Dohme Inc | 2-(benzene sulfonamido)-tetra-hydrobenzothiazoles |
| US2540356A (en) * | 1949-03-12 | 1951-02-06 | Sharp & Dohme Inc | Sulfonamide derivatives |
-
0
- BE BE622085D patent/BE622085A/xx unknown
- BE BE622086D patent/BE622086A/xx unknown
-
1961
- 1961-02-07 DE DEF33151A patent/DE1193952B/de active Pending
-
1962
- 1962-01-16 CH CH52062A patent/CH420168A/de unknown
- 1962-01-16 CH CH1135966A patent/CH421120A/de unknown
- 1962-01-23 US US168232A patent/US3180866A/en not_active Expired - Lifetime
- 1962-01-26 GB GB3103/62A patent/GB939608A/en not_active Expired
- 1962-11-08 FR FR914836A patent/FR2753M/fr not_active Expired
- 1962-11-08 FR FR914837A patent/FR2253M/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE933340C (de) * | 1939-11-24 | 1955-09-22 | Schering Ag | Verfahren zur Herstellung von therapeutisch wertvollen Mitteln der p-Aminobenzolsulfonamid-Reihe |
| DE975041C (de) * | 1941-07-25 | 1961-07-20 | Ici Ltd | Verfahren zur Herstellung von Sulfonamidderivaten des Pyrimidins |
| DE1027674B (de) | 1944-12-01 | 1958-04-10 | Schering Ag | Verfahren zur Herstellung von Sulfonamiden |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3694436A (en) * | 1970-03-02 | 1972-09-26 | Toyama Chemical Co Ltd | Substituted 2-(benzenesulfonamido)-pyrimidines |
Also Published As
| Publication number | Publication date |
|---|---|
| CH421120A (de) | 1966-09-30 |
| FR2253M (fr) | 1964-01-06 |
| US3180866A (en) | 1965-04-27 |
| FR2753M (fr) | 1962-08-31 |
| BE622086A (en, 2012) | |
| CH420168A (de) | 1966-09-15 |
| GB939608A (en) | 1963-10-16 |
| BE622085A (en, 2012) |
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