GB808071A - Manufacture of new sulphonyl-ureas - Google Patents
Manufacture of new sulphonyl-ureasInfo
- Publication number
- GB808071A GB808071A GB14305/56A GB1430556A GB808071A GB 808071 A GB808071 A GB 808071A GB 14305/56 A GB14305/56 A GB 14305/56A GB 1430556 A GB1430556 A GB 1430556A GB 808071 A GB808071 A GB 808071A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonyl
- benzene
- urea
- methyl
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- -1 sulphonyl ureas Chemical class 0.000 abstract 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 4
- 235000013877 carbamide Nutrition 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 4
- 239000012948 isocyanate Substances 0.000 abstract 4
- 150000002513 isocyanates Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000003973 alkyl amines Chemical class 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 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 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- HXWIBVJGIUIOJW-UHFFFAOYSA-N 1-(benzenesulfonyl)-1-(2-methylpropyl)urea Chemical compound C1(=CC=CC=C1)S(=O)(=O)N(C(=O)N)CC(C)C HXWIBVJGIUIOJW-UHFFFAOYSA-N 0.000 abstract 1
- TUTIQDHBWSGVMU-UHFFFAOYSA-N 1-(benzenesulfonyl)-1-butylurea Chemical compound CCCCN(C(N)=O)S(=O)(=O)C1=CC=CC=C1 TUTIQDHBWSGVMU-UHFFFAOYSA-N 0.000 abstract 1
- ZIRLDYOJRFPDFO-UHFFFAOYSA-N 1-butyl-1-(4-methylphenyl)sulfonylurea Chemical compound CCCCN(C(N)=O)S(=O)(=O)C1=CC=C(C)C=C1 ZIRLDYOJRFPDFO-UHFFFAOYSA-N 0.000 abstract 1
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract 1
- 229920002261 Corn starch Polymers 0.000 abstract 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 235000019759 Maize starch Nutrition 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 235000021307 Triticum Nutrition 0.000 abstract 1
- 241000209140 Triticum Species 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- KGLBPTAIQDBLJM-UHFFFAOYSA-N benzene sulfonylcarbamic acid Chemical compound S(=O)(=O)=NC(=O)O.C1=CC=CC=C1 KGLBPTAIQDBLJM-UHFFFAOYSA-N 0.000 abstract 1
- BVAPOGMQIPODIW-UHFFFAOYSA-N benzene;sulfonylurea Chemical compound C1=CC=CC=C1.NC(=O)N=S(=O)=O BVAPOGMQIPODIW-UHFFFAOYSA-N 0.000 abstract 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 230000006208 butylation Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 150000001714 carbamic acid halides Chemical class 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 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 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- DFWQXANLGSXMKF-UHFFFAOYSA-N ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 DFWQXANLGSXMKF-UHFFFAOYSA-N 0.000 abstract 1
- 229910003439 heavy metal oxide Inorganic materials 0.000 abstract 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 abstract 1
- JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 abstract 1
- XWKAGDYOTYFYPW-UHFFFAOYSA-N n-cyanobenzenesulfonamide Chemical compound N#CNS(=O)(=O)C1=CC=CC=C1 XWKAGDYOTYFYPW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 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 abstract 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 235000012222 talc Nutrition 0.000 abstract 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 abstract 1
- 150000003672 ureas Chemical class 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises sulphonyl ureas of the general formula <FORM:0808071/IV (b)/1> n which R2 and R3 represent hydrogen atoms or alkyl or alkoxy groups containing not more than 6 carbon atoms and R1 represents an aliphatic or cycloaliphatic hydrocarbon radical containing from 2 to 8, more preferably 3 to 5, carbon atoms, and non-toxic salts of these compounds. The products can be prepared by known methods for the production of sulphonyl ureas, for example, (1) a benzene-sulphonyl isocyanate is reacted with a primary alkylamine, cycloalkylamine, alkenylamine or cycloalkyl-alkylamine, or conversely a benzene sulphonamide is reacted with the appropriate isocyanate, or in place of the isocyanate, a compound which is convertible to an isocyanate, such as an azide, or a urethane or carbamic acid halide may be used; (2) a benzene sulphonyl urea which is unsubstituted in the -NH2 group is converted into a benzene sulphonyl alkyl urea by alkylation, for example by butylation with butylamine, or conversely an alkyl urea is reacted with a benzene sulphonamide; (3) a benzene sulphonic acid chloride is reacted with an iso-urea alkyl ether and the product obtained is converted by acid hydrolysis into the desired sulphonyl urea; (4) the corresponding benzene sulphonyl thiourea compound is prepared and the sulphur is eliminated therefrom in a conventional manner, e.g. by treatment with a heavy metal oxide or salt; (5) an N-benzene-sulphonyl-N1-alkylguanidine is made (for example by treating a benzenesulphonyl-cyanamide with butylamine or another primary amine), and the resulting guanidine is hydrolysed. In the above processes, the benzene sulphonyl compound may be alkyl- or alkoxy-substituted and the alkylamine may be an alkenylamine cycloalkylamine or cycloalkyl-alkylamine. The preferred processes are the reaction of a sulphonamide of the formula <FORM:0808071/IV (b)/2> with an isocyanate R1-NCO and the reaction of a benzene sulphonyl carbamic acid ester <FORM:0808071/IV (b)/3> in which R4 is a hydrocarbon residue, with an amine R1NH2. Examples describe the preparation of N-benzenesulphonyl-N1-n-butyl urea and the corresponding p-methyl-, p-ethyl-, p-n-propyl- and p-methoxy-derivatives; p-methyl-, p-methoxy-, m-methyl- and 3:4-dimethoxy-, N - benzenesulphonyl - N1 - isobutyl - urea; N-p - methylphenylsulphonyl - N1 - tert. - butyl-, sec. - butyl -, cyclohexyl -, allyl -, iso - amyl-, n - amyl -, cyclopentyl -, heptyl - (4), cyclo - hexylmethyl-, and n-hexyl-urea; and urea derivatives in which the N- and N1-substituents are respectively p-ethylphenylsulphonyl, cyclohexyl, 2 : 4 - dimethylphenylsulphonyl, cyclohexyl; m-methoxyphenylsulphonyl, n-hexyl; m-methoxyphenylsulphony, cyclohexyl. Many other products are specified. N - 4 - Methyl - benzenesulphonyl - carbamic acid ethyl ester and the corresponding methyl ester are made by treating 4-methylbenzenesulphonamide with ethyl or methyl chloroformate in the presence of potassium carbonate. N - 4 - Methylbenzenesulphonyl - and carbamoyl chloride is made by passing hydrogen chloride into 4-methylbenzenesulphonyl isocyanate.ALSO:Preparations suitable for the oral treatment of diabetes comprise compounds of the formula <FORM:0808071/VI/1> wherein R1 is an aliphatic or cycloaliphatic hydrocarbon radical of 2-8 carbon atoms and R2 and R3 are each hydrogen or an alkyl of alkoxy group of 1-6 carbon atoms, or salts of these compounds with bases which give physiologically tolerable salts in admixture with a pharmaceutically suitable carrier. The preparations suitably take the form of tablets, pills, capsules, cachets, mixtures, solutions or powders containing for example 0.5 grams of sulphonyl urea compound per dosage unit. In the above general formula R1 may suitably be an alkyl group such as propyl, butyl, pentyl, hexyl, heptyl or octyl, an alkenyl group such as allyl or crotyl, a cycloalkyl group such as cyclopentyl or cyclohexyl, or a cycloalkyl-alkyl group such as cyclohexyl-methyl or cyclohexylethyl. The benzene residue containing R2 and R3 is preferably a p-methyl-phenyl group. Many suitable products are specified (see Group IV (b)). In an example N-(4-methyl-benzene-sulphonyl) - N1 - n - butyl - urea is made up into tablets with wheat or maize starch, talc and magnesium stearate.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE342441X | 1955-05-28 | ||
| DE808071X | 1955-08-08 | ||
| DE30955X | 1955-09-03 | ||
| DE141055X | 1955-10-14 | ||
| DE191055X | 1955-10-19 | ||
| DE350170X | 1955-12-19 | ||
| DE280159X | 1959-01-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808071A true GB808071A (en) | 1959-01-28 |
Family
ID=58044242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14305/56A Expired GB808071A (en) | 1955-05-28 | 1956-05-08 | Manufacture of new sulphonyl-ureas |
Country Status (3)
| Country | Link |
|---|---|
| CY (1) | CY188A (en) |
| GB (1) | GB808071A (en) |
| MY (1) | MY6000026A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1179200B (en) * | 1960-01-26 | 1964-10-08 | Hoechst Ag | Process for the preparation of N-benzenesulfonyl-N'-methyl-cyclohexylureas |
| CN104649945A (en) * | 2015-02-05 | 2015-05-27 | 中国农业大学 | Preparation method of sulfonylurea and sulfonamide formate compounds |
| CN117903018A (en) * | 2024-01-11 | 2024-04-19 | 内蒙古科技大学 | Preparation method of tolbutamide crystal |
-
1956
- 1956-05-08 GB GB14305/56A patent/GB808071A/en not_active Expired
-
1959
- 1959-11-23 CY CY18859A patent/CY188A/en unknown
-
1960
- 1960-12-31 MY MY196026A patent/MY6000026A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1179200B (en) * | 1960-01-26 | 1964-10-08 | Hoechst Ag | Process for the preparation of N-benzenesulfonyl-N'-methyl-cyclohexylureas |
| CN104649945A (en) * | 2015-02-05 | 2015-05-27 | 中国农业大学 | Preparation method of sulfonylurea and sulfonamide formate compounds |
| CN117903018A (en) * | 2024-01-11 | 2024-04-19 | 内蒙古科技大学 | Preparation method of tolbutamide crystal |
Also Published As
| Publication number | Publication date |
|---|---|
| CY188A (en) | 1959-11-23 |
| MY6000026A (en) | 1960-12-31 |
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