CH524629A - Verfahren zur Herstellung von neuen Sulfonyl-semicarbaziden - Google Patents
Verfahren zur Herstellung von neuen Sulfonyl-semicarbazidenInfo
- Publication number
- CH524629A CH524629A CH1549568A CH1549568A CH524629A CH 524629 A CH524629 A CH 524629A CH 1549568 A CH1549568 A CH 1549568A CH 1549568 A CH1549568 A CH 1549568A CH 524629 A CH524629 A CH 524629A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- methyl
- ethyl
- benzenesulfonyl
- carboxamido
- Prior art date
Links
- ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000006181 N-acylation Effects 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 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
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 2
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- -1 6-amino-6-azabicyclo [3.2.1] -octane Chemical compound 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 16
- UGBKOURNNQREPE-UHFFFAOYSA-N azepan-1-amine Chemical compound NN1CCCCCC1 UGBKOURNNQREPE-UHFFFAOYSA-N 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- BSWGZCMLNFBDEZ-UHFFFAOYSA-N 4,5-dimethyl-1,2-oxazole Chemical compound CC=1C=NOC=1C BSWGZCMLNFBDEZ-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical compound CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 5
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
- CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical compound CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 125000005518 carboxamido group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- YUTQRQJTFPEEPB-UHFFFAOYSA-N 4-methyl-1,2-thiazole Chemical compound CC=1C=NSC=1 YUTQRQJTFPEEPB-UHFFFAOYSA-N 0.000 description 3
- XMVNMWDLOGSUSM-UHFFFAOYSA-N 5-methyl-1,2-oxazole-3-carbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=NO1 XMVNMWDLOGSUSM-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YIGSCEUQIQKFPL-UHFFFAOYSA-N 4-(1-aminoethyl)benzenesulfonamide Chemical compound CC(N)C1=CC=C(S(N)(=O)=O)C=C1 YIGSCEUQIQKFPL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- IAERAFZPWNQKDJ-UHFFFAOYSA-N [4-(2-aminoethyl)phenyl]sulfonylazanium;chloride Chemical compound [Cl-].NS(=O)(=O)C1=CC=C(CC[NH3+])C=C1 IAERAFZPWNQKDJ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960005371 tolbutamide Drugs 0.000 description 2
- SIACJRVYIPXFKS-UHFFFAOYSA-N (4-sulfamoylphenyl)methylazanium;chloride Chemical compound Cl.NCC1=CC=C(S(N)(=O)=O)C=C1 SIACJRVYIPXFKS-UHFFFAOYSA-N 0.000 description 1
- BADBQYAILRGCBB-UHFFFAOYSA-N 1,5-dimethylpyrazole-3-carbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=NN1C BADBQYAILRGCBB-UHFFFAOYSA-N 0.000 description 1
- GCHDAONHPITGRX-UHFFFAOYSA-N 1-ethenylsulfonylprop-1-ene Chemical compound CC=CS(=O)(=O)C=C GCHDAONHPITGRX-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
- KYOUKUFLSLXHNL-UHFFFAOYSA-N 3,4-dichloro-1,2-thiazole Chemical compound ClC1=CSN=C1Cl KYOUKUFLSLXHNL-UHFFFAOYSA-N 0.000 description 1
- MSSXWKAJMRSAGF-UHFFFAOYSA-N 3,4-dichloro-1,2-thiazole-5-carbonyl chloride Chemical compound ClC(=O)C=1SN=C(Cl)C=1Cl MSSXWKAJMRSAGF-UHFFFAOYSA-N 0.000 description 1
- JPVKCHIPRSQDKL-UHFFFAOYSA-N 3-aminobenzenesulfonamide Chemical compound NC1=CC=CC(S(N)(=O)=O)=C1 JPVKCHIPRSQDKL-UHFFFAOYSA-N 0.000 description 1
- SNGRYJSFEVUFBF-UHFFFAOYSA-N 3-aminopropane-1-sulfonamide Chemical compound NCCCS(N)(=O)=O SNGRYJSFEVUFBF-UHFFFAOYSA-N 0.000 description 1
- JATKRPGDXDPAOX-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octan-3-amine Chemical compound C1CC2N(N)CC1CC2 JATKRPGDXDPAOX-UHFFFAOYSA-N 0.000 description 1
- NYIDBIWYWWPALZ-UHFFFAOYSA-N 3-azabicyclo[3.2.0]heptan-3-amine Chemical compound NN1CC2CCC2C1 NYIDBIWYWWPALZ-UHFFFAOYSA-N 0.000 description 1
- BZWIERAEDHKQEK-UHFFFAOYSA-N 3-azabicyclo[3.2.1]octan-3-amine Chemical compound C1N(N)CC2CCC1C2 BZWIERAEDHKQEK-UHFFFAOYSA-N 0.000 description 1
- PTGWHSJNHJKONG-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-amine Chemical compound C1N(N)CC2CCC1CC2 PTGWHSJNHJKONG-UHFFFAOYSA-N 0.000 description 1
- RFKPNMKSMMUVRI-UHFFFAOYSA-N 3-azabicyclo[3.3.1]nonan-3-amine Chemical compound NN1CC2CCCC(C1)C2 RFKPNMKSMMUVRI-UHFFFAOYSA-N 0.000 description 1
- HOSKPQXIYUHSEU-UHFFFAOYSA-N 4-(1-aminopropyl)benzenesulfonamide Chemical compound CCC(N)C1=CC=C(S(N)(=O)=O)C=C1 HOSKPQXIYUHSEU-UHFFFAOYSA-N 0.000 description 1
- CRADEZLCQMNNCF-UHFFFAOYSA-N 4-(3-aminopropyl)benzenesulfonamide;hydrochloride Chemical compound Cl.NCCCC1=CC=C(S(N)(=O)=O)C=C1 CRADEZLCQMNNCF-UHFFFAOYSA-N 0.000 description 1
- FJVAYUUWTJKKNC-UHFFFAOYSA-N 4-(methylamino)benzenesulfonamide Chemical compound CNC1=CC=C(S(N)(=O)=O)C=C1 FJVAYUUWTJKKNC-UHFFFAOYSA-N 0.000 description 1
- XZMIAZCXISFPEJ-UHFFFAOYSA-N 4-aminobenzenesulfonamide;hydrochloride Chemical compound Cl.NC1=CC=C(S(N)(=O)=O)C=C1 XZMIAZCXISFPEJ-UHFFFAOYSA-N 0.000 description 1
- CHRAJVQLWOMYQI-UHFFFAOYSA-N 5,8,8-trimethyl-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1(C)C2(C)C CHRAJVQLWOMYQI-UHFFFAOYSA-N 0.000 description 1
- WDGWKCWPCNKPKD-UHFFFAOYSA-N 5-ethyl-1,2-oxazole-3-carbonyl chloride Chemical compound CCC1=CC(C(Cl)=O)=NO1 WDGWKCWPCNKPKD-UHFFFAOYSA-N 0.000 description 1
- SREMZRGHZGDSCI-UHFFFAOYSA-N 5-hexyl-1,2-oxazole Chemical compound CCCCCCC1=CC=NO1 SREMZRGHZGDSCI-UHFFFAOYSA-N 0.000 description 1
- AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical compound CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 description 1
- HXEVQMXCHCDPSO-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride Chemical compound ClC(=O)C1=C(C)ON=C1C1=CC=CC=C1 HXEVQMXCHCDPSO-UHFFFAOYSA-N 0.000 description 1
- KMRXZGHPUUAQOH-UHFFFAOYSA-N 5-octyl-1,2-oxazole Chemical compound CCCCCCCCC1=CC=NO1 KMRXZGHPUUAQOH-UHFFFAOYSA-N 0.000 description 1
- ATPGYYPVVKZFGR-UHFFFAOYSA-N 9-azabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1N2 ATPGYYPVVKZFGR-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- TYMRLRRVMHJFTF-UHFFFAOYSA-N Mafenide Chemical compound NCC1=CC=C(S(N)(=O)=O)C=C1 TYMRLRRVMHJFTF-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PKFUZCSOBWMUHH-UHFFFAOYSA-N ethyl N-(sulfonylmethyl)carbamate Chemical compound S(=O)(=O)=CNC(=O)OCC PKFUZCSOBWMUHH-UHFFFAOYSA-N 0.000 description 1
- 229940058172 ethylbenzene Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- IAFSUZIBZMPMPK-UHFFFAOYSA-N thiomorpholin-4-amine Chemical compound NN1CCSCC1 IAFSUZIBZMPMPK-UHFFFAOYSA-N 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- 229960002277 tolazamide Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671670952 DE1670952C3 (de) | 1967-11-25 | 1967-11-25 | ArylsuHonylsemicarbazide, Verfahren zu deren Herstellung und orales Antidiabetikum |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH524629A true CH524629A (de) | 1972-06-30 |
Family
ID=5686352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1549568A CH524629A (de) | 1967-11-25 | 1968-10-16 | Verfahren zur Herstellung von neuen Sulfonyl-semicarbaziden |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH524629A (enrdf_load_html_response) |
| ES (1) | ES360650A1 (enrdf_load_html_response) |
| IL (1) | IL30929A (enrdf_load_html_response) |
| NO (1) | NO129577B (enrdf_load_html_response) |
-
1968
- 1968-10-16 CH CH1549568A patent/CH524629A/de not_active IP Right Cessation
- 1968-10-22 IL IL6830929A patent/IL30929A/xx unknown
- 1968-11-16 NO NO04558/68A patent/NO129577B/no unknown
- 1968-11-25 ES ES360650A patent/ES360650A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL30929A (en) | 1973-06-29 |
| ES360650A1 (es) | 1970-07-16 |
| IL30929A0 (en) | 1968-12-26 |
| NO129577B (enrdf_load_html_response) | 1974-04-29 |
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