IL26023A - 4-chloro-3-sulfamoyl-benzene sulphonamides and their production - Google Patents
4-chloro-3-sulfamoyl-benzene sulphonamides and their productionInfo
- Publication number
- IL26023A IL26023A IL2602366A IL2602366A IL26023A IL 26023 A IL26023 A IL 26023A IL 2602366 A IL2602366 A IL 2602366A IL 2602366 A IL2602366 A IL 2602366A IL 26023 A IL26023 A IL 26023A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- chloro
- sulphonamido
- ethoxy
- compound
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- NENBAISIHCWPKP-UHFFFAOYSA-N Clofenamide Chemical class NS(=O)(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NENBAISIHCWPKP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- -1 BENZENE SULPHONAMIDES Chemical class 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UPQXFVNGCXRRTR-UHFFFAOYSA-N 2-methoxy-n,2-dimethylpropan-1-amine Chemical compound CNCC(C)(C)OC UPQXFVNGCXRRTR-UHFFFAOYSA-N 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XPAJSMLZWVNHGU-UHFFFAOYSA-N 1-(1-ethoxycyclopentyl)-n-methylmethanamine Chemical compound CCOC1(CNC)CCCC1 XPAJSMLZWVNHGU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WAFLIFILRXTZOB-UHFFFAOYSA-N 1-(1-methoxycyclopentyl)-n-methylmethanamine Chemical compound CNCC1(OC)CCCC1 WAFLIFILRXTZOB-UHFFFAOYSA-N 0.000 description 1
- HJXIDGGCRTZQJL-UHFFFAOYSA-N 1-(trichloromethyl)cyclopentan-1-ol Chemical compound ClC(Cl)(Cl)C1(O)CCCC1 HJXIDGGCRTZQJL-UHFFFAOYSA-N 0.000 description 1
- TYWVTQSZDVHDEM-UHFFFAOYSA-N 1-methoxycyclopentane-1-carboxylic acid Chemical compound COC1(C(O)=O)CCCC1 TYWVTQSZDVHDEM-UHFFFAOYSA-N 0.000 description 1
- PQQOECAUUMXPLV-UHFFFAOYSA-N 2-ethoxy-n,2-dimethylbutan-1-amine Chemical compound CCOC(C)(CC)CNC PQQOECAUUMXPLV-UHFFFAOYSA-N 0.000 description 1
- MRCYJNBEXCNWCW-UHFFFAOYSA-N 2-ethoxy-n,2-dimethylpropan-1-amine Chemical compound CCOC(C)(C)CNC MRCYJNBEXCNWCW-UHFFFAOYSA-N 0.000 description 1
- QUJLSJJOXQPWGI-UHFFFAOYSA-N 3-ethoxy-n,3-dimethylbutan-1-amine Chemical compound CCOC(C)(C)CCNC QUJLSJJOXQPWGI-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- 241000486634 Bena Species 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- DZFVZXVSCVXNGG-UHFFFAOYSA-N CNCC(CC)(CC)OCC Chemical compound CNCC(CC)(CC)OCC DZFVZXVSCVXNGG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- XXCDWNZJCDCQRI-UHFFFAOYSA-N ethyl 3-ethoxy-3-methylbutanoate Chemical compound CC(CC(=O)OCC)(C)OCC XXCDWNZJCDCQRI-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- VAHDSBMHHNXLQD-UHFFFAOYSA-N methyl 1-methoxycyclopentane-1-carboxylate Chemical compound COC(=O)C1(OC)CCCC1 VAHDSBMHHNXLQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XACRLNVZZAPUQF-UHFFFAOYSA-N n,2-dimethyl-2-(2-methylpropoxy)propan-1-amine Chemical compound CNCC(C)(C)OCC(C)C XACRLNVZZAPUQF-UHFFFAOYSA-N 0.000 description 1
- ORYHKOFVOOCAOT-UHFFFAOYSA-N n,2-dimethyl-2-propan-2-yloxypropan-1-amine Chemical compound CNCC(C)(C)OC(C)C ORYHKOFVOOCAOT-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0046470 | 1965-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL26023A true IL26023A (en) | 1969-12-31 |
Family
ID=7101050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2602366A IL26023A (en) | 1965-06-30 | 1966-06-24 | 4-chloro-3-sulfamoyl-benzene sulphonamides and their production |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT266077B (en, 2012) |
| CH (1) | CH473099A (en, 2012) |
| DE (1) | DE1493723A1 (en, 2012) |
| DK (1) | DK112585B (en, 2012) |
| FR (1) | FR5887M (en, 2012) |
| GB (1) | GB1086426A (en, 2012) |
| IL (1) | IL26023A (en, 2012) |
| SE (1) | SE321673B (en, 2012) |
-
1965
- 1965-06-30 DE DE19651493723 patent/DE1493723A1/de active Pending
-
1966
- 1966-06-24 IL IL2602366A patent/IL26023A/en unknown
- 1966-06-27 CH CH924366A patent/CH473099A/de not_active IP Right Cessation
- 1966-06-29 GB GB2920766A patent/GB1086426A/en not_active Expired
- 1966-06-29 DK DK337666A patent/DK112585B/da unknown
- 1966-06-29 AT AT621066A patent/AT266077B/de active
- 1966-06-29 SE SE890266A patent/SE321673B/xx unknown
- 1966-09-29 FR FR78187A patent/FR5887M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE321673B (en, 2012) | 1970-03-16 |
| AT266077B (de) | 1968-11-11 |
| DE1493723A1 (de) | 1969-02-13 |
| GB1086426A (en) | 1967-10-11 |
| CH473099A (de) | 1969-05-31 |
| DK112585B (da) | 1968-12-30 |
| FR5887M (en, 2012) | 1968-03-18 |
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