SU1591805A3 - Способ получения производного сульфонамцца - Google Patents
Способ получения производного сульфонамцца Download PDFInfo
- Publication number
- SU1591805A3 SU1591805A3 SU874202474A SU4202474A SU1591805A3 SU 1591805 A3 SU1591805 A3 SU 1591805A3 SU 874202474 A SU874202474 A SU 874202474A SU 4202474 A SU4202474 A SU 4202474A SU 1591805 A3 SU1591805 A3 SU 1591805A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compound
- solution
- ethane
- methyl
- evaporated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- -1 4-methanesulfonamidophenoxy Chemical group 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 11
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 206010003119 arrhythmia Diseases 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000001810 electrochemical catalytic reforming Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002085 irritant Substances 0.000 description 2
- 231100000021 irritant Toxicity 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 2
- 229960002370 sotalol Drugs 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- YQWCBDNNEZHPMA-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(OCCBr)C=C1 YQWCBDNNEZHPMA-UHFFFAOYSA-N 0.000 description 1
- OBCFOPGCTNULTG-UHFFFAOYSA-N 1-(2-chloroethoxy)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(OCCCl)C=C1 OBCFOPGCTNULTG-UHFFFAOYSA-N 0.000 description 1
- WQYDIXCUOGOFRF-UHFFFAOYSA-N 4-(2-chloroethoxy)aniline;hydrochloride Chemical compound Cl.NC1=CC=C(OCCCl)C=C1 WQYDIXCUOGOFRF-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 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
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- QOOOSPCWFVCKFK-UHFFFAOYSA-N N-benzyl-N'-(2-methylnaphthalen-1-yl)oxamide Chemical compound C1=CC=CC2=C1C=CC(C)=C2NC(=O)C(=O)NCC1=CC=CC=C1 QOOOSPCWFVCKFK-UHFFFAOYSA-N 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- MXWRJMIKMODSCY-UHFFFAOYSA-N ethane;dihydrochloride Chemical compound Cl.Cl.CC MXWRJMIKMODSCY-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- OPWXJASBLYLBIH-UHFFFAOYSA-N n-[4-(2-chloroethoxy)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(OCCCl)C=C1 OPWXJASBLYLBIH-UHFFFAOYSA-N 0.000 description 1
- PTPPVTUXJDJAGY-UHFFFAOYSA-N n-methyl-2-(4-nitrophenyl)ethanamine Chemical compound CNCCC1=CC=C([N+]([O-])=O)C=C1 PTPPVTUXJDJAGY-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 210000003540 papillary muscle Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LV931305A LV5466A3 (lv) | 1986-05-01 | 1993-12-03 | Sulfonamida atvasinajuma iegusanas panemiens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868610668A GB8610668D0 (en) | 1986-05-01 | 1986-05-01 | Anti-arrhythmia agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1591805A3 true SU1591805A3 (ru) | 1990-09-07 |
Family
ID=10597176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU874202474A SU1591805A3 (ru) | 1986-05-01 | 1987-04-30 | Способ получения производного сульфонамцца |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS62267250A (OSRAM) |
| DD (1) | DD268937A5 (OSRAM) |
| GB (1) | GB8610668D0 (OSRAM) |
| LV (1) | LV5466A3 (OSRAM) |
| MX (1) | MX6311A (OSRAM) |
| SU (1) | SU1591805A3 (OSRAM) |
| UA (1) | UA6154A1 (OSRAM) |
| ZA (1) | ZA873078B (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69531691T2 (de) * | 1994-08-04 | 2004-07-08 | C & C Research Labs | Neues amin-derivat, verfahren zur herstellung und dessen verwendung als anti-arrhythmisches mittel |
| HUE028976T2 (en) | 2003-06-17 | 2017-02-28 | Arena Pharm Inc | 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| KR20130087622A (ko) | 2004-12-23 | 2013-08-06 | 아레나 파마슈티칼스, 인크. | 5ｈｔ２ｃ 수용체 조정물질 조성물 및 그의 사용 방법 |
| WO2007120517A2 (en) | 2006-04-03 | 2007-10-25 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto |
| KR20100045983A (ko) * | 2007-06-29 | 2010-05-04 | 에모리 유니버시티 | 신경보호를 위한 ｎｍｄａ 수용체 길항물질 |
| CN102648170A (zh) | 2009-06-18 | 2012-08-22 | 艾尼纳制药公司 | 制备5-ht2c受体激动剂的方法 |
| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| US9365521B2 (en) | 2010-09-01 | 2016-06-14 | Arena Pharmaceuticals, Inc. | Non-hygroscopic salts of 5-HT2C agonists |
| SG188362A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| EA201390335A1 (ru) | 2010-09-01 | 2013-09-30 | Арена Фармасьютикалз, Инк. | Введение лоркасерина индивидуумам с почечной недостаточностью |
| WO2012030938A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Salts of lorcaserin with optically active acids |
| WO2014058441A1 (en) | 2012-10-09 | 2014-04-17 | Arena Pharmaceuticals, Inc. | Method of weight management |
-
1986
- 1986-05-01 GB GB868610668A patent/GB8610668D0/en active Pending
-
1987
- 1987-04-29 ZA ZA873078A patent/ZA873078B/xx unknown
- 1987-04-30 UA UA4202474A patent/UA6154A1/uk unknown
- 1987-04-30 MX MX631187A patent/MX6311A/es unknown
- 1987-04-30 SU SU874202474A patent/SU1591805A3/ru active
- 1987-04-30 DD DD87302295A patent/DD268937A5/de not_active IP Right Cessation
- 1987-05-01 JP JP62108720A patent/JPS62267250A/ja active Granted
-
1993
- 1993-12-03 LV LV931305A patent/LV5466A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX6311A (es) | 1993-08-01 |
| LV5466A3 (lv) | 1994-03-10 |
| ZA873078B (en) | 1988-12-28 |
| DD268937A5 (de) | 1989-06-14 |
| JPS62267250A (ja) | 1987-11-19 |
| UA6154A1 (uk) | 1994-12-29 |
| JPH0360814B2 (OSRAM) | 1991-09-17 |
| GB8610668D0 (en) | 1986-06-04 |
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