CH395059A - Verfahren zur Herstellung von neuen Sulfonylharnstoffen - Google Patents
Verfahren zur Herstellung von neuen SulfonylharnstoffenInfo
- Publication number
- CH395059A CH395059A CH1337364A CH1337364A CH395059A CH 395059 A CH395059 A CH 395059A CH 1337364 A CH1337364 A CH 1337364A CH 1337364 A CH1337364 A CH 1337364A CH 395059 A CH395059 A CH 395059A
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- benzenesulfonyl
- urea
- maximum
- radical
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 229940100389 Sulfonylurea Drugs 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 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
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- -1 ethylphenyl Chemical group 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 9
- 239000008280 blood Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003472 antidiabetic agent Substances 0.000 description 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 229940100445 wheat starch Drugs 0.000 description 3
- TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 2
- RLFFWWKJSJOYMQ-UHFFFAOYSA-N 1,3-diazepan-2-one Chemical compound O=C1NCCCCN1 RLFFWWKJSJOYMQ-UHFFFAOYSA-N 0.000 description 2
- PNCNMJWEZVCIHP-UHFFFAOYSA-N 3-(benzenesulfonyl)-1,1-diethylurea Chemical compound CCN(CC)C(=O)NS(=O)(=O)C1=CC=CC=C1 PNCNMJWEZVCIHP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000003178 anti-diabetic effect Effects 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- QNMWSLMZPATZTD-UHFFFAOYSA-N 1-benzyl-3-methylurea Chemical compound CNC(=O)NCC1=CC=CC=C1 QNMWSLMZPATZTD-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- IABRWXCXQSTUSS-UHFFFAOYSA-N 1-ethyl-3-methylurea Chemical compound CCNC(=O)NC IABRWXCXQSTUSS-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010018473 Glycosuria Diseases 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- JKLMYXKPKAVMKI-UHFFFAOYSA-N S(=O)(C=1C(=CC=CC=1)N)(=O)NC=1SC(=NN=1)C(C)C Chemical compound S(=O)(C=1C(=CC=CC=1)N)(=O)NC=1SC(=NN=1)C(C)C JKLMYXKPKAVMKI-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 241000282485 Vulpes vulpes Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical compound NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000035780 glucosuria Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 210000002700 urine Anatomy 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- 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
- 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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound 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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF26804A DE1157599B (de) | 1958-10-14 | 1958-10-14 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH395059A true CH395059A (de) | 1965-07-15 |
Family
ID=7092170
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1337364A CH395059A (de) | 1958-10-14 | 1959-10-12 | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |
| CH7932659A CH385818A (de) | 1958-10-14 | 1959-10-12 | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |
| CH1337264A CH395058A (de) | 1958-10-14 | 1959-10-12 | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7932659A CH385818A (de) | 1958-10-14 | 1959-10-12 | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |
| CH1337264A CH395058A (de) | 1958-10-14 | 1959-10-12 | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE583616A (pm) |
| CH (3) | CH395059A (pm) |
| DE (1) | DE1157599B (pm) |
| FR (6) | FR1312411A (pm) |
| GB (1) | GB863451A (pm) |
| NL (1) | NL244329A (pm) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4448491A2 (en) * | 2021-12-16 | 2024-10-23 | The United States of America, as represented by the Secretary, Department of Health and Human Services | N-((adamantan-1-yl)carbamoyl)-benzenesulfonamide derivatives as soluble epoxide hydrolase inhibitors for the treatment of hypertension |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1003716B (de) * | 1956-01-07 | 1957-03-07 | Hoechst Ag | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen |
-
0
- BE BE583616D patent/BE583616A/fr unknown
-
1958
- 1958-10-14 DE DEF26804A patent/DE1157599B/de active Pending
-
1959
- 1959-10-12 CH CH1337364A patent/CH395059A/de unknown
- 1959-10-12 CH CH7932659A patent/CH385818A/de unknown
- 1959-10-12 CH CH1337264A patent/CH395058A/de unknown
- 1959-10-13 FR FR807380A patent/FR1312411A/fr not_active Expired
- 1959-10-14 NL NL244329A patent/NL244329A/xx unknown
- 1959-10-14 GB GB34894/59A patent/GB863451A/en not_active Expired
-
1960
- 1960-08-31 FR FR837337A patent/FR545M/fr active Active
- 1960-08-31 FR FR837336A patent/FR544M/fr active Active
- 1960-08-31 FR FR837339A patent/FR547M/fr active Active
- 1960-08-31 FR FR837338A patent/FR546M/fr active Active
- 1960-08-31 FR FR837340A patent/FR548M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| DE1157599B (de) | 1963-11-21 |
| FR548M (pm) | 1961-05-29 |
| FR546M (pm) | 1961-05-29 |
| FR544M (pm) | 1961-05-29 |
| CH385818A (de) | 1964-12-31 |
| BE583616A (pm) | |
| CH395058A (de) | 1965-07-15 |
| FR547M (pm) | 1961-05-29 |
| NL244329A (pm) | 1964-01-27 |
| FR1312411A (fr) | 1962-12-21 |
| FR545M (pm) | 1961-05-29 |
| GB863451A (en) | 1961-03-22 |
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