CH427776A - Verfahren zur Herstellung von Benzolsulfonylharnstoffen - Google Patents

Verfahren zur Herstellung von Benzolsulfonylharnstoffen

Info

Publication number: CH427776A
Authority: CH; Switzerland
Prior art keywords: sep; benzenesulfonyl; urea; reaction; cyclohexyl
Prior art date: 1962-10-20

Application number

CH1276863A

Other languages

German (de)

English (en)

Inventor

Aumueller Walter

Muth Karl

Weber Helmut

Weyer Rudi

Herr Heinz

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.)

1962-10-20

Filing date

1963-10-17

Publication date

1967-01-15

1962-10-20 Priority claimed from DEF38097A external-priority patent/DE1181209B/de

1963-01-31 Priority claimed from DEF38884A external-priority patent/DE1177632B/de

1963-10-17 Application filed by Hoechst Ag filed Critical Hoechst Ag

1967-01-15 Publication of CH427776A publication Critical patent/CH427776A/de

Links

238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title description 3
-1 alkyl radical Chemical class 0.000 claims description 53
239000012280 lithium aluminium hydride Substances 0.000 claims description 15
239000008280 blood Substances 0.000 claims description 11
210000004369 blood Anatomy 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
239000003795 chemical substances by application 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
150000001447 alkali salts Chemical class 0.000 claims 1
HXCKCCRKGXHOBK-UHFFFAOYSA-N cycloheptane Chemical compound [CH]1CCCCCC1 HXCKCCRKGXHOBK-UHFFFAOYSA-N 0.000 claims 1
NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 claims 1
150000004679 hydroxides Chemical class 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
150000007530 organic bases Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
239000004202 carbamide Substances 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
241000283973 Oryctolagus cuniculus Species 0.000 description 8
239000000047 product Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000155 melt Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
235000013877 carbamide Nutrition 0.000 description 6
239000000126 substance Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000007858 starting material Substances 0.000 description 5
NAAPJKLEGXZKCX-UHFFFAOYSA-N OCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1 Chemical compound OCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1 NAAPJKLEGXZKCX-UHFFFAOYSA-N 0.000 description 4
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000005187 foaming Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZBHNOVZSCJEHTR-UHFFFAOYSA-N OC1=CC(=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C(C)C)C Chemical compound OC1=CC(=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C(C)C)C ZBHNOVZSCJEHTR-UHFFFAOYSA-N 0.000 description 3
KPVOUACUDCJFHV-UHFFFAOYSA-N OCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCC1 Chemical compound OCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCC1 KPVOUACUDCJFHV-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
QYKPRMWZTPVYJC-UHFFFAOYSA-N isocyanatocyclooctane Chemical compound O=C=NC1CCCCCCC1 QYKPRMWZTPVYJC-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229940124530 sulfonamide Drugs 0.000 description 3
238000010792 warming Methods 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
ARTPNDQYRVOJIX-UHFFFAOYSA-N C(=O)(OCC)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1 Chemical compound C(=O)(OCC)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1 ARTPNDQYRVOJIX-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
VMSSLXGOAYAGBG-UHFFFAOYSA-N OC(C(C=C1)=CC=C1S(NC(NC1CCCCCCC1)=O)(=O)=O)=O Chemical compound OC(C(C=C1)=CC=C1S(NC(NC1CCCCCCC1)=O)(=O)=O)=O VMSSLXGOAYAGBG-UHFFFAOYSA-N 0.000 description 2
LMYPNCXDTMCQPZ-UHFFFAOYSA-N OCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C Chemical compound OCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C LMYPNCXDTMCQPZ-UHFFFAOYSA-N 0.000 description 2
DGBWIWREWXSQRP-UHFFFAOYSA-N OCCCC(C=C1)=CC=C1S(NC(NC1CCCCCCC1)=O)(=O)=O Chemical compound OCCCC(C=C1)=CC=C1S(NC(NC1CCCCCCC1)=O)(=O)=O DGBWIWREWXSQRP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000005457 ice water Substances 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
150000007524 organic acids Chemical class 0.000 description 2
230000002269 spontaneous effect Effects 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
RGKZBZGSRPRAEO-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)urea Chemical compound CC(C)C1CCC(NC(N)=O)CC1 RGKZBZGSRPRAEO-UHFFFAOYSA-N 0.000 description 1
XTOBSLUVJNOXGB-UHFFFAOYSA-N 1-cyclooctyl-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCCCC1 XTOBSLUVJNOXGB-UHFFFAOYSA-N 0.000 description 1
UULCVOIRJRJPQS-UHFFFAOYSA-N 4-(hydroxymethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(CO)C=C1 UULCVOIRJRJPQS-UHFFFAOYSA-N 0.000 description 1
SJRHYONYKZIRPM-UHFFFAOYSA-N 4-hydroxytolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C1 SJRHYONYKZIRPM-UHFFFAOYSA-N 0.000 description 1
MFRKYEJMLQUSJX-UHFFFAOYSA-N 4-propan-2-ylcyclohexan-1-amine Chemical compound CC(C)C1CCC(N)CC1 MFRKYEJMLQUSJX-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
BBTUWTLWKXXJGF-UHFFFAOYSA-N C(=O)(OC)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C(C)C Chemical compound C(=O)(OC)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C(C)C BBTUWTLWKXXJGF-UHFFFAOYSA-N 0.000 description 1
VKGQESMQLXQTKN-UHFFFAOYSA-N CCOC(C(C=C1)=CC=C1S(NC(NC1CCCCCC1)=O)(=O)=O)=O Chemical compound CCOC(C(C=C1)=CC=C1S(NC(NC1CCCCCC1)=O)(=O)=O)=O VKGQESMQLXQTKN-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
244000265913 Crataegus laevigata Species 0.000 description 1
DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical group CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 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
DQNHNVJSWPPXFY-UHFFFAOYSA-N N-cyclooctylurea Chemical compound NC(=O)NC1CCCCCCC1 DQNHNVJSWPPXFY-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229940100389 Sulfonylurea Drugs 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001714 carbamic acid halides Chemical class 0.000 description 1
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000013078 crystal Substances 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
SZGLLXJFYCJRPP-UHFFFAOYSA-N cycloheptylurea Chemical compound NC(=O)NC1CCCCCC1 SZGLLXJFYCJRPP-UHFFFAOYSA-N 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
238000000354 decomposition reaction Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
JDKBOPJNCRHTNK-UHFFFAOYSA-N ethyl 2-[4-(cyclooctylcarbamoylsulfamoyl)phenyl]acetate Chemical compound C(=O)(OCC)CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1 JDKBOPJNCRHTNK-UHFFFAOYSA-N 0.000 description 1
UTUVIKZNQWNGIM-UHFFFAOYSA-N ethyl 2-phenylpropanoate Chemical compound CCOC(=O)C(C)C1=CC=CC=C1 UTUVIKZNQWNGIM-UHFFFAOYSA-N 0.000 description 1
DFTXGSKTFDBVQM-UHFFFAOYSA-N ethyl 4-sulfamoylbenzoate Chemical compound CCOC(=O)C1=CC=C(S(N)(=O)=O)C=C1 DFTXGSKTFDBVQM-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
JCNLHDHXQVZQAM-UHFFFAOYSA-N isocyanatocycloheptane Chemical compound O=C=NC1CCCCCC1 JCNLHDHXQVZQAM-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
MWSQYGRYGJGBSJ-UHFFFAOYSA-N methyl 4-[ethoxycarbonyl(methyl)sulfamoyl]benzoate Chemical compound C(=O)(OC)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C MWSQYGRYGJGBSJ-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
BVSPUXSSEOUOMK-UHFFFAOYSA-N n-(hydroxymethyl)benzenesulfonamide Chemical compound OCNS(=O)(=O)C1=CC=CC=C1 BVSPUXSSEOUOMK-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 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
238000002560 therapeutic procedure Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1276863A 1962-10-20 1963-10-17 Verfahren zur Herstellung von Benzolsulfonylharnstoffen CH427776A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEF38097A DE1181209B (de)	1962-10-20	1962-10-20	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DEF38884A DE1177632B (de)	1963-01-31	1963-01-31	Verfahren zur Herstellung von N-(Hydroxyalkyl-benzolsulfonyl)-N-(alkylcyclohexyl)-harnstoffen

Publications (1)

Publication Number	Publication Date
CH427776A true CH427776A (de)	1967-01-15

Family

ID=25975497

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1276863A CH427776A (de)	1962-10-20	1963-10-17	Verfahren zur Herstellung von Benzolsulfonylharnstoffen

Country Status (5)

Country	Link
AT (1)	AT244986B (da)
CH (1)	CH427776A (da)
DK (1)	DK102910C (da)
FR (1)	FR3191M (da)
GB (1)	GB1056823A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1329812A (en) *	1971-02-15	1973-09-12	Science Union & Cie	Benzenesulphonyl semicarbazides and a process for their preparation

1963
- 1963-10-17 CH CH1276863A patent/CH427776A/de unknown
- 1963-10-18 DK DK494163AA patent/DK102910C/da active
- 1963-10-18 AT AT835663A patent/AT244986B/de active
- 1963-10-21 GB GB41554/63A patent/GB1056823A/en not_active Expired
- 1963-12-19 FR FR957739A patent/FR3191M/fr active Active

Also Published As

Publication number	Publication date
FR3191M (fr)	1965-03-15
DK102910C (da)	1965-10-25
AT244986B (de)	1966-02-10
GB1056823A (en)	1967-02-01

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DD141521A5 (de)	1980-05-07	Verfahren zur herstellung neuer heterozyklischer benzamide
DE2723051A1 (de)	1977-12-01	N-(acyl)-p-amino-n'-(monosubstit.)- benzamide sowie diese enthaltende arzneimittel
DE1618465B2 (de)	1978-09-28	Phenylessigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
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DE2734270C2 (da)	1990-06-21
DE1181208B (de)	1964-11-12	Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen
DE2354931C2 (de)	1983-12-08	trans-2-Phenylbicyclooctan-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
DE2008332C3 (de)	1980-05-22	2-Methyl-S-methoxy-3-indolylacetohydroxamsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0672647B1 (de)	1998-12-09	Verfahren zur Herstellung von Aminoethylglycin
CH474490A (de)	1969-06-30	Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe
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