NO122923B - - Google Patents

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Info

Publication number: NO122923B
Authority: NO; Norway
Prior art keywords: benzenesulfonyl; phthalimidino; ethyl; urea; cyclohexyl
Prior art date: 1964-07-30

Application number

NO159136A

Other languages

English (en)

Norwegian (no)

Inventor

W Aumueller

K Muth

W Peschke

H Weber

R Weyer

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1964-07-30

Filing date

1965-07-29

Publication date

1971-09-06

1965-07-29 Application filed by Hoechst Ag filed Critical Hoechst Ag

1971-09-06 Publication of NO122923B publication Critical patent/NO122923B/no

Links

-1 phenylcyclopropyl Chemical group 0.000 claims description 30
239000004202 carbamide Substances 0.000 claims description 25
239000000126 substance Substances 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
239000008280 blood Substances 0.000 claims description 16
210000004369 blood Anatomy 0.000 claims description 16
235000013877 carbamide Nutrition 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000004434 sulfur atom Chemical group 0.000 claims description 9
150000003672 ureas Chemical class 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000001555 benzenes Chemical class 0.000 claims description 3
150000008331 benzenesulfonamides Chemical class 0.000 claims description 3
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims description 3
150000001714 carbamic acid halides Chemical class 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
125000005358 mercaptoalkyl group Chemical group 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000006622 cycloheptylmethyl group Chemical group 0.000 claims description 2
125000006623 cyclooctylmethyl group Chemical group 0.000 claims description 2
150000003560 thiocarbamic acids Chemical class 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
238000003756 stirring Methods 0.000 description 27
238000009835 boiling Methods 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
239000000243 solution Substances 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000000155 melt Substances 0.000 description 21
239000002244 precipitate Substances 0.000 description 20
238000001953 recrystallisation Methods 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
229910021529 ammonia Inorganic materials 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
239000000203 mixture Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
235000011121 sodium hydroxide Nutrition 0.000 description 8
WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
230000020477 pH reduction Effects 0.000 description 5
229940124530 sulfonamide Drugs 0.000 description 5
150000003456 sulfonamides Chemical class 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 4
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
SWSXEZOUBBVKCO-UHFFFAOYSA-N 1-isocyanato-4-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1 SWSXEZOUBBVKCO-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
229940101209 mercuric oxide Drugs 0.000 description 2
RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 description 2
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
PVMBGVAQRSHDBB-UHFFFAOYSA-N benzenesulfonylthiourea Chemical class NC(=S)NS(=O)(=O)C1=CC=CC=C1 PVMBGVAQRSHDBB-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 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
206010012601 diabetes mellitus Diseases 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
QQOVRPBUAUNBAV-UHFFFAOYSA-N ethyl 2-(chloromethyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CCl QQOVRPBUAUNBAV-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical group 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO159136A 1964-07-30 1965-07-29 NO122923B (pt)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEF0043614		1964-07-30
LU47776A LU47776A1 (pt)	1964-07-30	1965-01-13

Publications (1)

Publication Number	Publication Date
NO122923B true NO122923B (pt)	1971-09-06

Family

ID=25976392

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO159136A NO122923B (pt)	1964-07-30	1965-07-29

Country Status (18)

Country	Link
US (1)	US3510496A (pt)
AT (4)	AT273153B (pt)
BE (1)	BE667699A (pt)
BR (1)	BR6571713D0 (pt)
CH (1)	CH471117A (pt)
CY (1)	CY451A (pt)
DK (5)	DK118559B (pt)
ES (1)	ES326227A1 (pt)
FI (1)	FI45330C (pt)
FR (2)	FR1466292A (pt)
GB (1)	GB1093082A (pt)
IL (1)	IL23957A (pt)
LU (1)	LU47776A1 (pt)
MC (1)	MC546A1 (pt)
MY (1)	MY6900087A (pt)
NL (1)	NL142952B (pt)
NO (1)	NO122923B (pt)
OA (1)	OA03369A (pt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MTP848B (en) *	1978-06-27	1980-06-24	Hoechst Ag	Sulfonyl ureas process for their manufacture pharmaceutical preparation on the basis of there compounds and their use
EP0031088A1 (de) *	1979-12-19	1981-07-01	Hoechst Aktiengesellschaft	Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung
DE2951135A1 (de) *	1979-12-19	1981-06-25	Hoechst Ag, 6230 Frankfurt	Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung
FR2533563A1 (fr) *	1982-09-23	1984-03-30	Adir	Nouveaux derives de la sulfonyluree, leurs procedes de preparation et les compositions pharmaceutiques les renfermant
GB8609331D0 (en) *	1986-04-16	1986-05-21	Pfizer Ltd	Anti-arrythmia agents

1965
- 1965-01-13 LU LU47776A patent/LU47776A1/xx unknown
- 1965-02-23 GB GB7813/65A patent/GB1093082A/en not_active Expired
- 1965-07-14 IL IL23957A patent/IL23957A/xx unknown
- 1965-07-23 DK DK381665AA patent/DK118559B/da unknown
- 1965-07-26 FI FI651803A patent/FI45330C/fi active
- 1965-07-27 FR FR26124A patent/FR1466292A/fr not_active Expired
- 1965-07-28 CH CH1058065A patent/CH471117A/de not_active IP Right Cessation
- 1965-07-28 AT AT699365A patent/AT273153B/de active
- 1965-07-28 AT AT920567A patent/AT274833B/de active
- 1965-07-28 AT AT920367A patent/AT269165B/de active
- 1965-07-28 MC MC575A patent/MC546A1/xx unknown
- 1965-07-28 AT AT920267A patent/AT276423B/de active
- 1965-07-28 NL NL656509757A patent/NL142952B/xx unknown
- 1965-07-29 NO NO159136A patent/NO122923B/no unknown
- 1965-07-30 OA OA52129A patent/OA03369A/xx unknown
- 1965-07-30 BR BR171713/65A patent/BR6571713D0/pt unknown
- 1965-07-30 BE BE667699A patent/BE667699A/xx unknown
- 1965-10-26 FR FR36223A patent/FR4852M/fr not_active Expired
1966
- 1966-04-30 ES ES0326227A patent/ES326227A1/es not_active Expired
- 1966-09-12 DK DK468966AA patent/DK118661B/da unknown
- 1966-09-12 DK DK469166AA patent/DK119055B/da unknown
- 1966-09-12 DK DK469066AA patent/DK119007B/da unknown
- 1966-09-12 DK DK469266AA patent/DK123869B/da unknown
1968
- 1968-06-03 US US738729A patent/US3510496A/en not_active Expired - Lifetime
- 1968-08-23 CY CY45168A patent/CY451A/xx unknown
1969
- 1969-12-31 MY MY196987A patent/MY6900087A/xx unknown

Also Published As

Publication number	Publication date
MY6900087A (en)	1969-12-31
NL6509757A (pt)	1966-01-31
ES326227A1 (es)	1967-11-01
CY451A (en)	1968-08-23
AT274833B (de)	1969-10-10
NL142952B (nl)	1974-08-15
DK118661B (da)	1970-09-21
AT276423B (de)	1969-11-25
DK118559B (da)	1970-09-07
MC546A1 (fr)	1966-04-06
DK123869B (da)	1972-08-14
FI45330B (pt)	1972-01-31
DK119055B (da)	1970-11-09
US3510496A (en)	1970-05-05
AT273153B (de)	1969-08-11
GB1093082A (en)	1967-11-29
AT269165B (de)	1969-03-10
BE667699A (pt)	1966-01-31
BR6571713D0 (pt)	1973-08-14
CH471117A (de)	1969-04-15
FI45330C (fi)	1972-05-10
LU47776A1 (pt)	1966-07-13
FR1466292A (fr)	1967-01-20
OA03369A (fr)	1970-12-15
DK119007B (da)	1970-11-02
IL23957A (en)	1970-03-22
FR4852M (pt)	1967-02-20

Publication	Publication Date	Title
NO159136B (no)	1988-08-29	Truseinnlegg.
US3507961A (en)	1970-04-21	Benzenesulfonyl ureas as anti-diabetic agents
NO162257B (no)	1989-08-21	Fremgangm te for flytendegjoering av naturgass samtur dertil.
US3454635A (en)	1969-07-08	Benzenesulfonyl-ureas and process for their manufacture
NO159166B (no)	1988-08-29	Analogifremgangsmaate for fremstilling av farmakologisk aktive benzoazepinderivater.
NO155290B (no)	1986-12-01	Analogifremgangsmaate til fremstilling av terapeutisk virksomme sulfonylurinstoffderivater.
NO155188B (no)	1986-11-17	Bevegelig fottrinn for et kjoeretoey.
NO159754B (no)	1988-10-24	Fremgangsmaate for bestemmelse av karsinoembryonalt antigen (cea).
NO151837B (no)	1985-03-04	Anordning ved fagverk for bruk under bygging av bygninger og andre konstruksjoner
NO171025B (no)	1992-10-05	Takplate
US3406199A (en)	1968-10-15	Benzenesulfonyl ureas and process for their manufacture
NO122923B (pt)	1971-09-06
NO159998B (no)	1988-11-21	Analogifremgangsmaate ved fremstilling av et nytt terapeutisk aktivtsulfonamidderivat.
US3449346A (en)	1969-06-10	Benzenesulfonyl ureas
NO771728L (no)	1977-11-21	Benzensulfonylurinstoffer og fremgangsm}te til deres fremstilling
US3705151A (en)	1972-12-05	Benzene-sulfonyl semicarbazides and process for preparing them
NO165846B (no)	1991-01-07	Vinylkloridmateriale, samt fremgangsmaate for fremstillingav et slikt.
US3336322A (en)	1967-08-15	Benzenesulfonyl ureas and process for their manufacture
NO122920B (pt)	1971-09-06
US3917690A (en)	1975-11-04	Benzenesulfonyl ureas and process for their manufacture
US3435116A (en)	1969-03-25	The treatment of diabetes mellitus with benzenesulfonyl ureas
IL28873A (en)	1973-02-28	Benzenesulfonyl ureas and process for their manufacture
US3621057A (en)	1971-11-16	Benzenesulfonyl-ureas and process for their manufacture
NO162926B (no)	1989-11-27	Apparat for velgbar rett eller retningsbestemt boring i underjordiske formasjoner.
US3790630A (en)	1974-02-05	Benzenesulfonyl-ureas