CH466281A - Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden - Google Patents

Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden

Info

Publication number: CH466281A
Authority: CH; Switzerland
Prior art keywords: methyl; methoxy; benzenesulfonyl; dimethyl; preparation
Prior art date: 1961-10-03

Application number

CH972166A

Other languages

German (de)

English (en)

Inventor

Aumueller Walter

Weyer Rudi

Weber Helmut

Haack Erich

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.)

1961-10-03

Filing date

1962-10-01

Publication date

1968-12-15

1962-10-01 Application filed by Hoechst Ag filed Critical Hoechst Ag

1968-12-15 Publication of CH466281A publication Critical patent/CH466281A/de

Links

238000000034 method Methods 0.000 title claims description 12
LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
239000008280 blood Substances 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
-1 methoxy, ethoxy, propoxy, butyloxy, pentyloxy Chemical group 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000003839 salts Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001555 benzenes Chemical class 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
231100000053 low toxicity Toxicity 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
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
ZXLNOQLIBVACTD-UHFFFAOYSA-N (methylideneamino)urea Chemical compound NC(=O)NN=C ZXLNOQLIBVACTD-UHFFFAOYSA-N 0.000 description 1
ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
241000699670 Mus sp. Species 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
JWPWVPPTDSULMI-UHFFFAOYSA-N benzenesulfonamidothiourea Chemical class NC(=S)NNS(=O)(=O)C1=CC=CC=C1 JWPWVPPTDSULMI-UHFFFAOYSA-N 0.000 description 1
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 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
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006477 desulfuration reaction Methods 0.000 description 1
230000023556 desulfurization Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 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
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
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 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
150000007530 organic bases Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 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
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/56—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms

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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

CH972166A 1961-10-03 1962-10-01 Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden CH466281A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0035040		1961-10-03

Publications (1)

Publication Number	Publication Date
CH466281A true CH466281A (de)	1968-12-15

Family

ID=7095831

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH972166A CH466281A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
CH1151862A CH418327A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH972066A CH466280A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH1151862A CH418327A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH972066A CH466280A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden

Country Status (4)

Country	Link
CH (3)	CH466281A (da)
DK (2)	DK101978C (da)
FR (1)	FR2837M (da)
GB (1)	GB979007A (da)

1962
- 1962-10-01 CH CH972166A patent/CH466281A/de unknown
- 1962-10-01 CH CH1151862A patent/CH418327A/de unknown
- 1962-10-01 CH CH972066A patent/CH466280A/de unknown
- 1962-10-02 DK DK330363AA patent/DK101978C/da active
- 1962-10-02 DK DK330163AA patent/DK102801C/da active
- 1962-10-02 GB GB37347/62A patent/GB979007A/en not_active Expired
1963
- 1963-10-12 FR FR920243A patent/FR2837M/fr active Active

Also Published As

Publication number	Publication date
FR2837M (fr)	1964-10-12
DK102801C (da)	1965-10-11
CH466280A (de)	1968-12-15
DK101978C (da)	1965-06-21
GB979007A (en)	1965-01-01
CH418327A (de)	1966-08-15

Publication	Publication Date	Title
DE1147947B (de)	1963-05-02	Verfahren zur Herstellung neuer 1, 2-Benzisothiazolone
CH466281A (de)	1968-12-15	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
AT236412B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
DE1246754B (de)	1967-08-10	Verfahren zur Herstellung von Derivaten des 7-Oxycumarins
DE1095836B (de)	1960-12-29	Verfahren zur Herstellung von in 10-Stellung basisch substituierten Phenthiazinderivaten
AT234111B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
DE1645901C3 (de)	1975-01-30	gamma-(4-Alkylp!peridino)-p-fluorbutyrophenone und Verfahren zu ihrer Herstellung
DE1795153A1 (de)	1971-12-30	Neue N-substituierte Piperidinspiroverbindungen,ihre Verwendung und Herstellung
AT234109B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
AT266075B (de)	1968-11-11	Verfahren zur Herstellung von neuen Sulfonaniliden und deren Säureadditions- und Metallsalzen
AT234110B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT236409B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT236410B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-alkylen-semicarbaziden
AT262269B (de)	1968-06-10	Verfahren zur Herstellung von neuen 1-Phenly-2-alkylcyclohexyl-aminoäthyl-äthern und deren Säureadditionssalzen
AT236401B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT250342B (de)	1966-11-10	Verfahren zur Herstellung von neuen Derivaten des 1-Phenyl-2, 3-dimethyl-4-amino-pyrazolons-(5)
AT235850B (de)	1964-09-25	Verfahren zur Herstellung von neuen Benzolsulfonylalkylensemicarbaziden
AT236411B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT236407B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-alkylen-semicarbaziden
AT339324B (de)	1977-10-10	Verfahren zur herstellung von neuen 1,4-disubstituierten piperazin-derivaten und deren saureadditionsverbindungen
DE1695595A1 (de)	1972-01-20	Verfahren zur Herstellung von 1,2,3,4-Tetrahydro-4a(H)-pyrimido-[5,4-b][1,4]-benzothiazin-2,4-dionen
AT268323B (de)	1969-02-10	Verfahren zur Herstellung von neuen 3,1-Benzothiazin-Derivaten und ihren Salzen
AT236414B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
AT238218B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT234113B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden