CH363335A - Verfahren zur Herstellung von Sulfonylharnstoffen - Google Patents

Verfahren zur Herstellung von Sulfonylharnstoffen

Info

Publication number: CH363335A
Authority: CH; Switzerland
Prior art keywords: urea; butyl; alkali; reaction; alkaline earth
Prior art date: 1956-09-17

Application number

CH5058157A

Other languages

German (de)

English (en)

Inventor

Martin Chemerda John

James Tull Roger

Original Assignee

Merck & Co Inc

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.)

1956-09-17

Filing date

1957-09-16

Publication date

1962-07-31

1957-09-16 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1962-07-31 Publication of CH363335A publication Critical patent/CH363335A/de

Links

238000000034 method Methods 0.000 title claims description 20
229940100389 Sulfonylurea Drugs 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 6
-1 alkaline earth metal salt Chemical class 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 19
AQSQFWLMFCKKMG-UHFFFAOYSA-N 1,3-dibutylurea Chemical compound CCCCNC(=O)NCCCC AQSQFWLMFCKKMG-UHFFFAOYSA-N 0.000 claims description 18
229940124530 sulfonamide Drugs 0.000 claims description 18
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 14
239000003513 alkali Substances 0.000 claims description 13
239000004202 carbamide Substances 0.000 claims description 10
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
150000003456 sulfonamides Chemical class 0.000 claims description 8
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 claims description 6
VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 claims description 6
LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 claims description 6
HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
239000007795 chemical reaction product Substances 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
235000013877 carbamide Nutrition 0.000 description 14
239000000203 mixture Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000008280 blood Substances 0.000 description 11
210000004369 blood Anatomy 0.000 description 11
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
150000003672 ureas Chemical class 0.000 description 9
230000002218 hypoglycaemic effect Effects 0.000 description 8
159000000000 sodium salts Chemical class 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
YWXUADNLTYADPN-UHFFFAOYSA-N 1-butyl-3-(4-chlorophenyl)sulfonylurea Chemical group CCCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 YWXUADNLTYADPN-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000007086 side reaction Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 4
BBQLCKFJEDETJU-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-phenylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC=C1 BBQLCKFJEDETJU-UHFFFAOYSA-N 0.000 description 3
TYRVXLIAZXPCND-UHFFFAOYSA-N 1-ethyl-3-(4-methylphenyl)sulfonylurea Chemical compound CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 TYRVXLIAZXPCND-UHFFFAOYSA-N 0.000 description 3
QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
229940126904 hypoglycaemic agent Drugs 0.000 description 3
ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-UHFFFAOYSA-N 0.000 description 2
CVYAATGPNZIRSG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(OC)=CC=C1NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 CVYAATGPNZIRSG-UHFFFAOYSA-N 0.000 description 2
MGPSBPIAKKOJQX-UHFFFAOYSA-N 1-butyl-3-(4-nitrophenyl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 MGPSBPIAKKOJQX-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
239000003472 antidiabetic agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical class CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 2
ZIFOWKKZIWXFJO-UHFFFAOYSA-N n-[4-(butylcarbamoylsulfamoyl)phenyl]acetamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 ZIFOWKKZIWXFJO-UHFFFAOYSA-N 0.000 description 2
235000020075 ouzo Nutrition 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
OLOWDQIMFNQPJS-UHFFFAOYSA-N (4-nitrophenyl)sulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 OLOWDQIMFNQPJS-UHFFFAOYSA-N 0.000 description 1
AURPMRPZTDOADA-UHFFFAOYSA-N 1,3-bis(3-methylbutyl)urea Chemical compound CC(C)CCNC(=O)NCCC(C)C AURPMRPZTDOADA-UHFFFAOYSA-N 0.000 description 1
229940057054 1,3-dimethylurea Drugs 0.000 description 1
RLXNWBVDCNYQJV-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-phenylurea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1=CC=CC=C1 RLXNWBVDCNYQJV-UHFFFAOYSA-N 0.000 description 1
XVNQDOYXXCSYPH-UHFFFAOYSA-N 1-butyl-3-(3,4-dichlorophenyl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 XVNQDOYXXCSYPH-UHFFFAOYSA-N 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
238000004737 colorimetric analysis Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
DFTXGSKTFDBVQM-UHFFFAOYSA-N ethyl 4-sulfamoylbenzoate Chemical class CCOC(=O)C1=CC=C(S(N)(=O)=O)C=C1 DFTXGSKTFDBVQM-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical class CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical class NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229950010053 sulfacarbamide Drugs 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH5058157A 1956-09-17 1957-09-16 Verfahren zur Herstellung von Sulfonylharnstoffen CH363335A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US61041856A	1956-09-17	1956-09-17

Publications (1)

Publication Number	Publication Date
CH363335A true CH363335A (de)	1962-07-31

Family

ID=24444933

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5058157A CH363335A (de)	1956-09-17	1957-09-16	Verfahren zur Herstellung von Sulfonylharnstoffen

Country Status (4)

Country	Link
CH (1)	CH363335A (es)
DE (1)	DE1418307A1 (es)
ES (1)	ES237496A1 (es)
GB (1)	GB835811A (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1188589B (de) *	1963-12-14	1965-03-11	Hoechst Ag	Verfahren zur Herstellung von Benzolsulfonylharnstoffen

1957
- 1957-09-02 GB GB2765657A patent/GB835811A/en not_active Expired
- 1957-09-03 ES ES0237496A patent/ES237496A1/es not_active Expired
- 1957-09-12 DE DE19571418307 patent/DE1418307A1/de active Pending
- 1957-09-16 CH CH5058157A patent/CH363335A/de unknown

Also Published As

Publication number	Publication date
ES237496A1 (es)	1958-03-01
GB835811A (en)	1960-05-25
DE1418307A1 (de)	1968-10-10

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