CH510029A - Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden - Google Patents

Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Info

Publication number: CH510029A
Authority: CH; Switzerland
Prior art keywords: urea; semicarbazides; compounds; octanyl; benzenesulphonyl
Prior art date: 1966-11-04

Application number

CH1534567A

Other languages

German (de)

English (en)

Inventor

Erich Dr Phil Haack

Nat Heerdt Ruth Dr Rer

Nat Schmidt Felix Helmut D Rer

Stach Kurt Ing Dr

Karl Dr Muth

Original Assignee

Boehringer Mannheim Gmbh

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.)

1966-11-04

Filing date

1967-11-02

Publication date

1971-07-15

1967-11-02 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1971-07-15 Publication of CH510029A publication Critical patent/CH510029A/de

Links

LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 title claims abstract description 6
239000003472 antidiabetic agent Substances 0.000 title description 2
230000003178 anti-diabetic effect Effects 0.000 title 1
239000004202 carbamide Substances 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 6
125000002252 acyl group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 5
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
239000008280 blood Substances 0.000 abstract description 3
210000004369 blood Anatomy 0.000 abstract description 3
206010012601 diabetes mellitus Diseases 0.000 abstract description 3
230000000694 effects Effects 0.000 abstract description 3
150000003863 ammonium salts Chemical class 0.000 abstract description 2
230000004069 differentiation Effects 0.000 abstract description 2
229940127017 oral antidiabetic Drugs 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
-1 4-methyl-benzenesulfonyl Chemical group 0.000 description 11
235000013877 carbamide Nutrition 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical class C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
150000004008 N-nitroso compounds Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
150000001714 carbamic acid halides Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
KWHXRPOBVUXTNC-UHFFFAOYSA-N ethyl N-(4-methoxyphenyl)sulfonyl-N-methylcarbamate Chemical compound COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C KWHXRPOBVUXTNC-UHFFFAOYSA-N 0.000 description 1
FACGRORYCNHVPV-UHFFFAOYSA-N ethyl n-(4-chlorophenyl)sulfonylcarbamate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 FACGRORYCNHVPV-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
239000003538 oral antidiabetic agent Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003349 semicarbazides Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
150000003673 urethanes Chemical class 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
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CH1534567A 1966-11-04 1967-11-02 Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden CH510029A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEB0089688		1966-11-04

Publications (1)

Publication Number	Publication Date
CH510029A true CH510029A (de)	1971-07-15

Family

ID=6984887

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1534567A CH510029A (de)	1966-11-04	1967-11-02	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Country Status (6)

Country	Link
AT (1)	AT276424B (fr)
CH (1)	CH510029A (fr)
DE (1)	DE1670164A1 (fr)
FR (1)	FR1552976A (fr)
GB (1)	GB1137380A (fr)
NL (1)	NL6714889A (fr)

1966
- 1966-11-04 DE DE19661670164 patent/DE1670164A1/de active Pending
1967
- 1967-11-02 GB GB4981167A patent/GB1137380A/en not_active Expired
- 1967-11-02 CH CH1534567A patent/CH510029A/de not_active IP Right Cessation
- 1967-11-02 NL NL6714889A patent/NL6714889A/xx unknown
- 1967-11-03 AT AT993267A patent/AT276424B/de active
- 1967-11-03 FR FR1552976D patent/FR1552976A/fr not_active Expired

Also Published As

Publication number	Publication date
FR1552976A (fr)	1969-01-10
DE1670164A1 (de)	1970-11-05
AT276424B (de)	1969-11-25
NL6714889A (fr)	1968-05-06
GB1137380A (en)	1968-12-18

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Legal Events

Date	Code	Title	Description
1974-06-14	PL	Patent ceased