HUP0401715A2 - Eljárás racém és enantiomerszerűen tiszta 1,5-diaril-3-trifluormetil-delta2-pirazol-származékok előállítására - Google Patents
Eljárás racém és enantiomerszerűen tiszta 1,5-diaril-3-trifluormetil-delta2-pirazol-származékok előállításáraInfo
- Publication number
- HUP0401715A2 HUP0401715A2 HU0401715A HUP0401715A HUP0401715A2 HU P0401715 A2 HUP0401715 A2 HU P0401715A2 HU 0401715 A HU0401715 A HU 0401715A HU P0401715 A HUP0401715 A HU P0401715A HU P0401715 A2 HUP0401715 A2 HU P0401715A2
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- trifluoromethyl
- enantiomerically pure
- reacted
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 2
- -1 methoxy, trifluoromethoxy, methylsulfonyl Chemical group 0.000 abstract 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000003219 pyrazolines Chemical class 0.000 abstract 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 abstract 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000001099 ammonium carbonate Substances 0.000 abstract 1
- 235000012501 ammonium carbonate Nutrition 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 abstract 1
- 229960002179 ephedrine Drugs 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 150000004031 phenylhydrazines Chemical class 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- 235000010265 sodium sulphite Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A találmány tárgya eljárás az (1) általános képletű vegyületek -amelyek közé tartoznak (+)-1 jelölésű racém elegyek és (-)-1 és (+)-Ijelölésű enantiomerszerűen tiszta vegyületek az (1) általánosképletben R2 és R3 azonos vagy eltérő jelentéssel hidrogén-, klór-vagy fluoratomot vagy metil-, trifluormetil- vagy metoxicsoportotjelent; R2 jelentése hidrogén-, klór- vagy fluoratom vagy metil-,trifluormetil-, metoxi-, trifluormetoxi-, metilszulfonil- vagyaminoszulfonilcsoport; R4 jelentése hidrogén-, klór- vagy fluoratomvagy metil-, trifluormetil-, metoxi-, trifluormetoxi-, metilszulfonil-vagy aminoszulfonilcsoport; azzal a megkötéssel; hogy R2 és R4helyettesítők közül az egyik metilszulfonil- vagyaminoszulfonilcsoportot jelent - előállítására. A találmány értelmébenúgy járnak el, hogy (+)-1 jelölésű racém elegyet állítanak elő úgy,hogy valamely (I) általános képletű (E)-1,1,l-trifluor-4-aril-3-butén-2-on-származékot valamely (II) általános képletű fenilhidrazin-származékkal reagáltatnak, egy így kapott pirazolin-származékotklórszulfonsavval, majd nátriumhidroxiddal és végül tionilkloriddalreagáltatnak. Az említett reakciók valamelyikével kapottpirazolinszármazékot ammóniumkarbonáttal vagy ammóniával, vagy pedignátriumszulfittal és metiljodiddal vagy metilszulfáttal reagáltatják.Járulékosan, (I) általános képletű, enantiomerszerűen tisztavegyületeket állítanak elő úgy, hogy egy (+)-1 általános képletű racémelegyet enantiomerjeire választanak szét úgy, hogy optikailag aktívefedrinnel végeznek reagáltatást, ezután az egyes enantiamereknekelőállítják a nátriumsóját, az utóbbit tionilkloriddal, majdnátriumszulfttal és metiljodiddal vagy metilszulfáttal reagáltatják,amikor külön-külön enantiomerszerűen tiszta (-)-1 és (+)-1 általánosképletű vegyületeket kapnak. Ó
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200101412A ES2183720B1 (es) | 2001-06-18 | 2001-06-18 | Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras. |
| PCT/ES2002/000274 WO2002102781A1 (es) | 2001-06-18 | 2002-06-06 | Procedimiento para la preparación de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racémicas y enantioméricamente puras |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0401715A2 true HUP0401715A2 (hu) | 2005-01-28 |
| HUP0401715A3 HUP0401715A3 (en) | 2005-06-28 |
Family
ID=8498105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0401715A HUP0401715A3 (en) | 2001-06-18 | 2002-06-06 | Method of preparing derivatives of 1,5-diaryl-3-trifluoromethyl-delta2-pyrazolines that are racemic and enantiomerically pure |
Country Status (27)
| Country | Link |
|---|---|
| US (3) | US6846935B2 (hu) |
| EP (1) | EP1408035B1 (hu) |
| JP (1) | JP2005502604A (hu) |
| KR (1) | KR20040018275A (hu) |
| CN (1) | CN1275946C (hu) |
| AR (1) | AR036050A1 (hu) |
| AT (1) | ATE315030T1 (hu) |
| BG (1) | BG108524A (hu) |
| BR (1) | BR0211009A (hu) |
| CA (1) | CA2451132C (hu) |
| CZ (1) | CZ200481A3 (hu) |
| DE (1) | DE60208551T2 (hu) |
| DK (1) | DK1408035T3 (hu) |
| EE (1) | EE200400016A (hu) |
| ES (2) | ES2183720B1 (hu) |
| HK (1) | HK1077058A1 (hu) |
| HU (1) | HUP0401715A3 (hu) |
| IL (1) | IL159367A0 (hu) |
| MX (1) | MXPA03011783A (hu) |
| NO (1) | NO20035642L (hu) |
| PL (1) | PL367773A1 (hu) |
| PT (1) | PT1408035E (hu) |
| RU (1) | RU2288915C2 (hu) |
| SI (1) | SI1408035T1 (hu) |
| SK (1) | SK422004A3 (hu) |
| WO (1) | WO2002102781A1 (hu) |
| ZA (1) | ZA200400343B (hu) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2183720B1 (es) * | 2001-06-18 | 2004-01-16 | Esteve Labor Dr | Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras. |
| US20080138282A1 (en) * | 2004-06-03 | 2008-06-12 | The Trustees Of Columbia University In The City Of New York | Radiolabeled Arylsulfonyl Compounds and Uses Thereof |
| DE102004057303A1 (de) * | 2004-11-26 | 2006-06-01 | Merck Patent Gmbh | Stabile Kristallmodifikationen von DOTAP Chlorid |
| EP1757587A1 (en) * | 2005-07-15 | 2007-02-28 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| US9376420B2 (en) * | 2012-10-25 | 2016-06-28 | Yuhan Corporation | 4,5-dihydro-1H-pyrazole derivative or salts thereof, and pharmaceutical composition comprising same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788658R (fr) * | 1971-09-09 | 1973-03-12 | Hoechst Ag | Derives de 3-(3', 4'-dichloro-6'-alkylphenyl) -delta2-pyrazolines, leurpreparation et leur utilisation comme agents d'azurage |
| ES2137138B1 (es) * | 1998-05-29 | 2000-09-16 | Esteve Labor Dr | Derivados de pirazolinas, su preparacion y su aplicacion como medicamentos. |
| CA2377153A1 (en) * | 1999-06-16 | 2000-12-21 | Temple University - Of The Commonwealth System Of Higher Education | 1-(4-sulfamylaryl)-3-substituted-5-aryl-2-pyrazolines as inhibitors of cyclooxygenase-2 |
| ES2183720B1 (es) * | 2001-06-18 | 2004-01-16 | Esteve Labor Dr | Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras. |
-
2001
- 2001-06-18 ES ES200101412A patent/ES2183720B1/es not_active Expired - Fee Related
-
2002
- 2002-06-06 HU HU0401715A patent/HUP0401715A3/hu unknown
- 2002-06-06 DE DE60208551T patent/DE60208551T2/de not_active Expired - Lifetime
- 2002-06-06 BR BR0211009-1A patent/BR0211009A/pt not_active IP Right Cessation
- 2002-06-06 EP EP02735442A patent/EP1408035B1/en not_active Expired - Lifetime
- 2002-06-06 MX MXPA03011783A patent/MXPA03011783A/es active IP Right Grant
- 2002-06-06 CZ CZ200481A patent/CZ200481A3/cs unknown
- 2002-06-06 EE EEP200400016A patent/EE200400016A/xx unknown
- 2002-06-06 SI SI200230277T patent/SI1408035T1/sl unknown
- 2002-06-06 JP JP2003505323A patent/JP2005502604A/ja active Pending
- 2002-06-06 RU RU2004101050/04A patent/RU2288915C2/ru not_active IP Right Cessation
- 2002-06-06 CN CNB028143280A patent/CN1275946C/zh not_active Expired - Fee Related
- 2002-06-06 AT AT02735442T patent/ATE315030T1/de active
- 2002-06-06 IL IL15936702A patent/IL159367A0/xx unknown
- 2002-06-06 KR KR10-2003-7016500A patent/KR20040018275A/ko not_active Application Discontinuation
- 2002-06-06 ES ES02735442T patent/ES2256483T3/es not_active Expired - Lifetime
- 2002-06-06 PL PL02367773A patent/PL367773A1/xx not_active Application Discontinuation
- 2002-06-06 WO PCT/ES2002/000274 patent/WO2002102781A1/es active IP Right Grant
- 2002-06-06 US US10/312,194 patent/US6846935B2/en not_active Expired - Fee Related
- 2002-06-06 CA CA2451132A patent/CA2451132C/en not_active Expired - Fee Related
- 2002-06-06 SK SK42-2004A patent/SK422004A3/sk unknown
- 2002-06-06 DK DK02735442T patent/DK1408035T3/da active
- 2002-06-06 PT PT02735442T patent/PT1408035E/pt unknown
- 2002-06-12 AR ARP020102218A patent/AR036050A1/es not_active Application Discontinuation
-
2003
- 2003-12-17 NO NO20035642A patent/NO20035642L/no not_active Application Discontinuation
-
2004
- 2004-01-13 BG BG108524A patent/BG108524A/bg unknown
- 2004-01-16 ZA ZA2004/00343A patent/ZA200400343B/en unknown
- 2004-12-08 US US11/006,931 patent/US20050096474A1/en not_active Abandoned
- 2004-12-08 US US11/007,449 patent/US6958403B2/en not_active Expired - Fee Related
-
2005
- 2005-10-13 HK HK05109018A patent/HK1077058A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |