CH421118A - Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen - Google Patents
Verfahren zur Herstellung von neuen Sulfonamiden und von deren SalzenInfo
- Publication number
- CH421118A CH421118A CH1003366A CH1003366A CH421118A CH 421118 A CH421118 A CH 421118A CH 1003366 A CH1003366 A CH 1003366A CH 1003366 A CH1003366 A CH 1003366A CH 421118 A CH421118 A CH 421118A
- Authority
- CH
- Switzerland
- Prior art keywords
- meaning
- interrupted
- general formula
- ring
- process according
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims description 12
- 150000003456 sulfonamides Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 sulfonamide derivatives of thiodiazole Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WLSUNIXHBRXXFV-UHFFFAOYSA-N n-(5-methylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1 WLSUNIXHBRXXFV-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WMTOIVOXCKKOGT-UHFFFAOYSA-N sodium (4-methoxyphenyl)sulfonylazanide Chemical compound [Na+].COC1=CC=C(S([NH-])(=O)=O)C=C1 WMTOIVOXCKKOGT-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000456 subacute toxicity Toxicity 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- RSUBGBZOMBTDTI-UHFFFAOYSA-N 2-chloro-5-methoxypyrimidine Chemical compound COC1=CN=C(Cl)N=C1 RSUBGBZOMBTDTI-UHFFFAOYSA-N 0.000 description 1
- LSEAFZZPTHTUDZ-UHFFFAOYSA-N 4-methoxy-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide Chemical compound COC1=CC=C(C=C1)S(=O)(=O)NC1=NC=C(C=N1)OC LSEAFZZPTHTUDZ-UHFFFAOYSA-N 0.000 description 1
- OWJVDKUMHJYFDO-UHFFFAOYSA-N 5-ethoxy-N,N-dimethylpyrimidin-2-amine Chemical compound CN(C1=NC=C(C=N1)OCC)C OWJVDKUMHJYFDO-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CTRTZNUCBQNRCK-UHFFFAOYSA-N COC1=CN=C(NS(=O)(=O)CCC(C)C)N=C1 Chemical compound COC1=CN=C(NS(=O)(=O)CCC(C)C)N=C1 CTRTZNUCBQNRCK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- JJZCJFOIERCODT-UHFFFAOYSA-N N-(5-ethoxypyrimidin-2-yl)-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(C=C1)S(=O)(=O)NC1=NC=C(C=N1)OCC JJZCJFOIERCODT-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- ANVDYLHKNDBHCA-UHFFFAOYSA-N NC1=CC=C(C=C1)S(=O)(=O)NN1N=C(C=C1)SC(C)C Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NN1N=C(C=C1)SC(C)C ANVDYLHKNDBHCA-UHFFFAOYSA-N 0.000 description 1
- 208000015906 Necrobiotic disease Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000010030 glucose lowering effect Effects 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 206010019692 hepatic necrosis Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 231100000149 liver necrosis Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QBHACRJLGYNGIF-UHFFFAOYSA-N n-(5-propoxypyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(OCCC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QBHACRJLGYNGIF-UHFFFAOYSA-N 0.000 description 1
- HLBLNLYCFFWMFF-UHFFFAOYSA-N n-pyrimidin-2-ylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=NC=CC=N1 HLBLNLYCFFWMFF-UHFFFAOYSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC028634 | 1960-10-18 | ||
| DE1961SC029273 DE1445142B2 (de) | 1960-10-18 | 1961-02-22 | 2-(benzolsulfonamido)-5-methoxyaethoxy- pyrimidinderivate |
| DESCH29280A DE1175680B (de) | 1961-02-22 | 1961-02-23 | Verfahren zur Herstellung von 2-Sulfonamidopyrimidinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH421118A true CH421118A (de) | 1966-09-30 |
Family
ID=27212278
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1003366A CH421118A (de) | 1960-10-18 | 1961-10-10 | Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen |
| CH1003566A CH438327A (de) | 1960-10-18 | 1961-10-10 | Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen |
| CH1003466A CH421119A (de) | 1960-10-18 | 1961-10-10 | Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1003566A CH438327A (de) | 1960-10-18 | 1961-10-10 | Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen |
| CH1003466A CH421119A (de) | 1960-10-18 | 1961-10-10 | Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen |
Country Status (3)
| Country | Link |
|---|---|
| CH (3) | CH421118A (enrdf_load_stackoverflow) |
| GB (1) | GB997631A (enrdf_load_stackoverflow) |
| SE (4) | SE220351C1 (enrdf_load_stackoverflow) |
-
1961
- 1961-10-10 CH CH1003366A patent/CH421118A/de unknown
- 1961-10-10 CH CH1003566A patent/CH438327A/de unknown
- 1961-10-10 CH CH1003466A patent/CH421119A/de unknown
- 1961-10-12 GB GB36693/61A patent/GB997631A/en not_active Expired
- 1961-10-16 SE SE1025661A patent/SE220351C1/sv unknown
-
1964
- 1964-01-07 SE SE012464A patent/SE220353C1/sv unknown
- 1964-01-07 SE SE012664A patent/SE220355C1/sv unknown
- 1964-01-07 SE SE012564A patent/SE220354C1/sv unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH438327A (de) | 1967-06-30 |
| CH421119A (de) | 1966-09-30 |
| SE220354C1 (enrdf_load_stackoverflow) | 1968-05-07 |
| SE220355C1 (enrdf_load_stackoverflow) | 1968-05-07 |
| SE220351C1 (enrdf_load_stackoverflow) | 1968-05-07 |
| SE220353C1 (enrdf_load_stackoverflow) | 1968-05-07 |
| GB997631A (en) | 1965-07-07 |
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