DE1183075B - Verfahren zur Herstellung von N-Benzolsulfonyl-N'-bicyclo-[2, 2, 1]-heptyl-harnstoffe - Google Patents
Verfahren zur Herstellung von N-Benzolsulfonyl-N'-bicyclo-[2, 2, 1]-heptyl-harnstoffeInfo
- Publication number
- DE1183075B DE1183075B DES85962A DES0085962A DE1183075B DE 1183075 B DE1183075 B DE 1183075B DE S85962 A DES85962 A DE S85962A DE S0085962 A DES0085962 A DE S0085962A DE 1183075 B DE1183075 B DE 1183075B
- Authority
- DE
- Germany
- Prior art keywords
- heptyl
- bicyclo
- urea
- trimethyl
- group
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- -1 bicyclic amine Chemical class 0.000 description 33
- 239000004202 carbamide Substances 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229940100389 Sulfonylurea Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VJWUPQYVKKINMS-UHFFFAOYSA-N 2,2,3-trimethylbicyclo[2.2.1]heptan-3-amine Chemical compound C1CC2C(N)(C)C(C)(C)C1C2 VJWUPQYVKKINMS-UHFFFAOYSA-N 0.000 description 2
- MDFWXZBEVCOVIO-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptan-3-amine Chemical compound C1CC2(C)C(N)CC1C2(C)C MDFWXZBEVCOVIO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 230000023852 carbohydrate metabolic process Effects 0.000 description 2
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 2
- 229940126904 hypoglycaemic agent Drugs 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LPQZZTSZMIMKQK-UHFFFAOYSA-N 3,3-dimethylbicyclo[2.2.1]heptan-2-amine Chemical compound C1CC2C(N)C(C)(C)C1C2 LPQZZTSZMIMKQK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
- 206010018473 Glycosuria Diseases 0.000 description 1
- 208000013016 Hypoglycemia Diseases 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
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960001761 chlorpropamide Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DDNCKBTWKYSFTE-UHFFFAOYSA-N ethyl n-(4-acetylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(C(C)=O)C=C1 DDNCKBTWKYSFTE-UHFFFAOYSA-N 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007449 liver function test Methods 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 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
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
-
- 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)
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25241/62A GB1007019A (en) | 1962-07-02 | 1962-07-02 | New terpenic derivatives and the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1183075B true DE1183075B (de) | 1964-12-10 |
Family
ID=10224493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES85962A Pending DE1183075B (de) | 1962-07-02 | 1963-07-02 | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-bicyclo-[2, 2, 1]-heptyl-harnstoffe |
Country Status (8)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH474519A (de) * | 1966-07-12 | 1969-06-30 | Geigy Ag J R | Verfahren zur Herstellung von neuen N'- substituierten N-Arylsulfonylharnstoffen |
| US3832397A (en) * | 1970-03-19 | 1974-08-27 | Hoffmann La Roche | Process for substituted sulfonylureas |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2762842A (en) * | 1952-06-10 | 1956-09-11 | Geigy Ag J R | N-aryl-n'-aminoalkyl-ureas |
| DE1237094B (de) * | 1957-02-26 | 1967-03-23 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von oral anwendbaren, antidiabetisch wirksamen Sulfonylharnstoffen |
| US2928871A (en) * | 1957-10-01 | 1960-03-15 | Hoffmann La Roche | 1-terpenyl-3-arylsulfonylureas |
| US3072527A (en) * | 1959-07-01 | 1963-01-08 | Horner Frank W Ltd | Use of tolbutamide in the treatment of acne |
| US3072720A (en) * | 1960-04-07 | 1963-01-08 | Upjohn Co | Novel n-arylsulfonyl-n'-(2, 5-endomethylene-1, 2, 5, 6-tetrahydrobenzyl) ureas |
| US3048519A (en) * | 1961-02-20 | 1962-08-07 | American Cyanamid Co | Benzenesulfonamido-halo-pyrimidines: antibacterials |
| CH457415A (de) * | 1961-06-03 | 1968-06-15 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| DE1157211B (de) * | 1961-07-28 | 1963-11-14 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| US3155721A (en) * | 1961-11-30 | 1964-11-03 | Lilly Co Eli | Novel sulfonylureas |
| US3136814A (en) * | 1962-04-07 | 1964-06-09 | Irikura Tsutomu | Sulfonylurea derivatives |
-
0
- NL NL294761D patent/NL294761A/xx unknown
-
1962
- 1962-07-02 GB GB25241/62A patent/GB1007019A/en not_active Expired
-
1963
- 1963-06-28 US US291244A patent/US3334302A/en not_active Expired - Lifetime
- 1963-06-28 BR BR150247/63A patent/BR6350247D0/pt unknown
- 1963-07-01 DK DK312063AA patent/DK115913B/da unknown
- 1963-07-01 CH CH814463A patent/CH414592A/fr unknown
- 1963-07-02 DE DES85962A patent/DE1183075B/de active Pending
- 1963-09-30 FR FR949029A patent/FR3094M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CH414592A (fr) | 1966-06-15 |
| NL294761A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| US3334302A (en) | 1967-08-01 |
| DK115913B (da) | 1969-11-24 |
| GB1007019A (en) | 1965-10-13 |
| BR6350247D0 (pt) | 1973-08-14 |
| FR3094M (fr) | 1965-02-01 |
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