DE2759241C3 - N-(4-(2-(pyrazol-1-carbonamido)-athyl)-benzolsulfonyl) carbonide, verfahren zu ihrer herstellung und arzneimittel - Google Patents
N-(4-(2-(pyrazol-1-carbonamido)-athyl)-benzolsulfonyl) carbonide, verfahren zu ihrer herstellung und arzneimittelInfo
- Publication number
- DE2759241C3 DE2759241C3 DE772759241A DE2759241A DE2759241C3 DE 2759241 C3 DE2759241 C3 DE 2759241C3 DE 772759241 A DE772759241 A DE 772759241A DE 2759241 A DE2759241 A DE 2759241A DE 2759241 C3 DE2759241 C3 DE 2759241C3
- Authority
- DE
- Germany
- Prior art keywords
- melting point
- carbonamido
- ethyl
- crystallization
- benzenesulfonyl
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title description 10
- 229940126601 medicinal product Drugs 0.000 title description 2
- 239000004202 carbamide Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- 238000002844 melting Methods 0.000 description 50
- 230000008018 melting Effects 0.000 description 50
- 150000001875 compounds Chemical class 0.000 description 43
- 238000002425 crystallisation Methods 0.000 description 39
- 230000008025 crystallization Effects 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 16
- 210000004369 blood Anatomy 0.000 description 15
- 239000008280 blood Substances 0.000 description 15
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 14
- 239000008103 glucose Substances 0.000 description 14
- SEFWPFZOECXWQL-UHFFFAOYSA-N n-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-3-methylpyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 SEFWPFZOECXWQL-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 11
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- RMTYNAPTNBJHQI-LLDVTBCESA-N glibornuride Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N[C@H]1[C@H](C2(C)C)CC[C@@]2(C)[C@H]1O RMTYNAPTNBJHQI-LLDVTBCESA-N 0.000 description 8
- 229960001764 glibornuride Drugs 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- -1 cycloalkyl radical Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000002218 hypoglycaemic effect Effects 0.000 description 6
- CZALJDQHONFVFU-UHFFFAOYSA-N isocyanatocyclopentane Chemical compound O=C=NC1CCCC1 CZALJDQHONFVFU-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- WHYQCQRHPQBZHM-UHFFFAOYSA-N pyrazole-1-carboxylic acid Chemical class OC(=O)N1C=CC=N1 WHYQCQRHPQBZHM-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- JUMVRMAJYJPEKH-UHFFFAOYSA-N 3-methylpyrazole-1-carboxylic acid Chemical compound CC=1C=CN(C(O)=O)N=1 JUMVRMAJYJPEKH-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZQTSRIDUHMMUBQ-UHFFFAOYSA-N 3-ethyl-4-methylpyrazole-1-carboxylic acid Chemical compound CCC1=NN(C(O)=O)C=C1C ZQTSRIDUHMMUBQ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229960003362 carbutamide Drugs 0.000 description 3
- DIGOIFUBVQCQTA-UHFFFAOYSA-N 3,4-dimethylpyrazole-1-carboxylic acid Chemical compound CC1=CN(C(O)=O)N=C1C DIGOIFUBVQCQTA-UHFFFAOYSA-N 0.000 description 2
- WMXDHTDKVGBIBO-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboxylic acid Chemical compound CC=1C=C(C)N(C(O)=O)N=1 WMXDHTDKVGBIBO-UHFFFAOYSA-N 0.000 description 2
- 208000013016 Hypoglycemia Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 230000002045 lasting effect Effects 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
- 239000000126 substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- NMBWXBWFDHVLGS-UHFFFAOYSA-N 2-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1S(N)(=O)=O NMBWXBWFDHVLGS-UHFFFAOYSA-N 0.000 description 1
- UZAFKQQKGUDIJU-UHFFFAOYSA-N 3,4,5-trimethylpyrazole-1-carboxylic acid Chemical compound CC1=NN(C(O)=O)C(C)=C1C UZAFKQQKGUDIJU-UHFFFAOYSA-N 0.000 description 1
- PNZZQMXKKNDHNS-UHFFFAOYSA-N 3-methylpyrazole-1-carboxamide Chemical compound CC=1C=CN(C(N)=O)N=1 PNZZQMXKKNDHNS-UHFFFAOYSA-N 0.000 description 1
- OTJQIMGXZSYBBE-UHFFFAOYSA-N 4-butyl-3,5-dimethylpyrazole-1-carboxylic acid Chemical compound CCCCC=1C(C)=NN(C(O)=O)C=1C OTJQIMGXZSYBBE-UHFFFAOYSA-N 0.000 description 1
- VQZUGFKXFRMILB-UHFFFAOYSA-N 4-chloro-3-methylpyrazole-1-carboxylic acid Chemical compound CC1=NN(C(O)=O)C=C1Cl VQZUGFKXFRMILB-UHFFFAOYSA-N 0.000 description 1
- BAVLEZBPVIRHKC-UHFFFAOYSA-N 4-chloropyrazole-1-carboxylic acid Chemical compound OC(=O)N1C=C(Cl)C=N1 BAVLEZBPVIRHKC-UHFFFAOYSA-N 0.000 description 1
- IZGZQDNFGBBDGK-UHFFFAOYSA-N 4-ethylpyrazole-1-carboxylic acid Chemical compound CCC=1C=NN(C(O)=O)C=1 IZGZQDNFGBBDGK-UHFFFAOYSA-N 0.000 description 1
- QWAVQVCZEIBDLE-UHFFFAOYSA-N 4-methylpyrazole-1-carboxylic acid Chemical compound CC=1C=NN(C(O)=O)C=1 QWAVQVCZEIBDLE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 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
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229960004580 glibenclamide Drugs 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
- 210000000777 hematopoietic system Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100001252 long-term toxicity Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D231/16—Halogen atoms or nitro radicals
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon 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
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Endocrinology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1976195000A PL106114B1 (pl) | 1976-12-31 | 1976-12-31 | Sposob wytwarzania nowych n-(4-/2-/pirazolo-1-karbonamido/-etylo/-benzenosulfonylo)-mocznikow |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2759241A1 DE2759241A1 (de) | 1978-07-06 |
| DE2759241B2 DE2759241B2 (de) | 1980-07-24 |
| DE2759241C3 true DE2759241C3 (de) | 1981-05-21 |
Family
ID=19980256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE772759241A Expired DE2759241C3 (de) | 1976-12-31 | 1977-12-31 | N-(4-(2-(pyrazol-1-carbonamido)-athyl)-benzolsulfonyl) carbonide, verfahren zu ihrer herstellung und arzneimittel |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4153710A (enExample) |
| JP (1) | JPS53149974A (enExample) |
| DE (1) | DE2759241C3 (enExample) |
| GB (1) | GB1592380A (enExample) |
| PL (1) | PL106114B1 (enExample) |
| SU (2) | SU789520A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0402309A3 (en) * | 2001-12-21 | 2008-09-29 | Novo Nordisk As | Amide derivatives as glucokinase activators and pharmaceutical compositions containing them |
| BR0312023A (pt) * | 2002-06-27 | 2005-03-22 | Novo Nordisk As | Composto, composto ativador da glicose cinase, método para evitar a hipoglicemia, uso de um composto, e, composição farmacêutica |
| DK1723128T3 (da) * | 2004-01-06 | 2013-02-18 | Novo Nordisk As | Heteroarylurinstoffer og deres anvendelse som glucokinaseaktivatorer |
| CA2614518A1 (en) * | 2005-07-08 | 2007-01-18 | Novo-Nordisk A/S | Dicycloalkyl urea glucokinase activators |
| JP2009500378A (ja) * | 2005-07-08 | 2009-01-08 | ノボ・ノルデイスク・エー／エス | グルコキナーゼ活性化剤としてのジシクロアルキルカルバモイル尿素 |
| EP2377856A1 (en) | 2005-07-14 | 2011-10-19 | Novo Nordisk A/S | Urea glucokinase activators |
| JP2010515701A (ja) * | 2007-01-09 | 2010-05-13 | ノボ・ノルデイスク・エー／エス | ウレアグルコキナーゼアクチベーター |
| AU2008204530B2 (en) | 2007-01-11 | 2013-08-01 | Vtv Therapeutics Llc | Urea glucokinase activators |
| AU2019287437A1 (en) | 2018-06-12 | 2020-09-10 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| WO2021167840A1 (en) | 2020-02-18 | 2021-08-26 | Vtv Therapeutics Llc | Sulfoxide and sulfone glucokinase activators and methods of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH516578A (de) * | 1967-11-02 | 1971-12-15 | Bayer Ag | Verfahren zur Herstellung von heterocyclische Acylaminogruppen enthaltenden Arylsulfonylharnstoffen mit blutdrucksenkender Wirkung |
| US3668215A (en) * | 1967-11-25 | 1972-06-06 | Bayer Ag | Aryl-sulphonyl-semicarbazides containing heterocyclic acylamino groups |
| US3887709A (en) * | 1971-09-16 | 1975-06-03 | Zdzislaw Brzozowski | 2-Pyrazoline-1-carboxamide sulfonamide derivatives useful as hypoglycemic agents |
| CH593263A5 (enExample) * | 1974-02-22 | 1977-11-30 | Hoffmann La Roche | |
| AU473887B2 (en) * | 1975-05-30 | 1975-07-10 | Kyorin Pharmaceutical Co. Ltd. | Novel pyrazole derivatives |
-
1976
- 1976-12-31 PL PL1976195000A patent/PL106114B1/pl unknown
-
1977
- 1977-12-13 SU SU772552354A patent/SU789520A1/ru active
- 1977-12-20 US US05/862,755 patent/US4153710A/en not_active Expired - Lifetime
- 1977-12-21 GB GB53313/77A patent/GB1592380A/en not_active Expired
- 1977-12-28 JP JP16094077A patent/JPS53149974A/ja active Granted
- 1977-12-31 DE DE772759241A patent/DE2759241C3/de not_active Expired
-
1978
- 1978-11-24 SU SU782688156A patent/SU816398A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5633391B2 (enExample) | 1981-08-03 |
| JPS53149974A (en) | 1978-12-27 |
| GB1592380A (en) | 1981-07-08 |
| DE2759241B2 (de) | 1980-07-24 |
| SU816398A3 (ru) | 1981-03-23 |
| DE2759241A1 (de) | 1978-07-06 |
| PL195000A1 (pl) | 1978-11-20 |
| US4153710A (en) | 1979-05-08 |
| SU789520A1 (ru) | 1980-12-23 |
| PL106114B1 (pl) | 1979-11-30 |
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