HRP20130103T1 - Postupak dobivanja montelukastove kiseline u ionskom tekuä†em mediju - Google Patents
Postupak dobivanja montelukastove kiseline u ionskom tekuä†em mediju Download PDFInfo
- Publication number
- HRP20130103T1 HRP20130103T1 HRP20130103AT HRP20130103T HRP20130103T1 HR P20130103 T1 HRP20130103 T1 HR P20130103T1 HR P20130103A T HRP20130103A T HR P20130103AT HR P20130103 T HRP20130103 T HR P20130103T HR P20130103 T1 HRP20130103 T1 HR P20130103T1
- Authority
- HR
- Croatia
- Prior art keywords
- image
- hexafluorophosphate
- bromide
- butyl
- group
- Prior art date
Links
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 title claims 3
- 229960005127 montelukast Drugs 0.000 title claims 3
- 239000002253 acid Substances 0.000 title claims 2
- 239000002608 ionic liquid Substances 0.000 title claims 2
- -1 thiol compound Chemical class 0.000 claims 12
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 150000008040 ionic compounds Chemical class 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 3
- GWQYPLXGJIXMMV-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;bromide Chemical compound [Br-].CCN1C=C[N+](C)=C1 GWQYPLXGJIXMMV-UHFFFAOYSA-M 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 claims 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (7)
1. Postupak dobivanja Montelukastove kiseline formule 1 ili njezine natrijeve soli,
[image]
,
naznačen time što se sastoji u koraku kondenziranja tiolnog spoja formule 2
[image]
s Montelukastovim međuproduktom formule 3
[image]
,
u prisutnosti baze, u mediju koji sadrži tekući ionski spoj, kojeg se bira iz skupine koju čine spojevi formula 4a do 4e:
[image]
[image]
[image]
[image]
[image]
gdje
R1 je vodik, metil ili etil;
L-O je izlazna skupina, gdje se L bira iz skupine koju čine metansulfonil, p-toluensulfonil, dimetilfosforil, dietilfosforil i difenilfosforil;
svaki od R2 i R3 je neovisno vodik ili C1-12 alkil; i
X je Cl, Br, BF4, PF6, SbF6, bis((trifluormetan)sulfonil)imid) (NTf2), (tritluormetan)sulfonat (OTf), acetat (OAc), NO3 ili metansulfonat.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što L je difenilfosforil.
3. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se tekući ionski spoj bira iz skupine koju čine 1-etil-3-metilimidazolijev bromid, 1-metil-3-metilimidazolijev heksafluorofosfat, N-butil-N-metilpirolidijev bromid, N-butil-N-metilpirolidijev heksafluorofosfat, N-butil-3-metilpiridijev bromid, N-butil-3-metilpiridijev heksafluorofosfat, tetra-N-butilamonijev bromid, tetra-N-butilamonijev heksafluorofosfat, tetra-N-butilfosfonijev bromid i tetra-N-butilfosfonijev heksafluorofosfat.
4. Postupak u skladu s patentnim zahtjevom 3, naznačen time što ionski tekući spoj je 1-etil-3-metilimidazolijev bromid ili N-butil-N-metilpirolidijev heksafluorofosfat.
5. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se tekući ionski spoj upotrebljava u rasponu količina koje su 0,1 do 100-struka težina spoja formule 3.
6. Postupak u skladu s patentnim zahtjevom 1, naznačen time što baza se bira iz skupine koju čine kalijev t-butoksid, natrijev t-butoksid, NaH, NaOH, te KOH.
7. Postupak u skladu s patentnim zahtjevom 6, naznačen time što baza je kalijev t-butoksid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020070101486A KR101072896B1 (ko) | 2007-10-09 | 2007-10-09 | 이온성 액체 매개체를 이용한 몬테루카스트산의 제조 방법 |
| PCT/KR2008/005794 WO2009048236A1 (en) | 2007-10-09 | 2008-10-01 | Method for the preparation of montelukast acid in ionic liquid medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20130103T1 true HRP20130103T1 (hr) | 2013-02-28 |
Family
ID=40549354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20130103AT HRP20130103T1 (hr) | 2007-10-09 | 2013-02-06 | Postupak dobivanja montelukastove kiseline u ionskom tekuä†em mediju |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8426599B2 (hr) |
| EP (1) | EP2195295B1 (hr) |
| JP (1) | JP5210389B2 (hr) |
| KR (1) | KR101072896B1 (hr) |
| CN (1) | CN101808998B (hr) |
| AR (1) | AR068755A1 (hr) |
| CA (1) | CA2701912C (hr) |
| CL (1) | CL2008002996A1 (hr) |
| DK (1) | DK2195295T3 (hr) |
| ES (1) | ES2398732T3 (hr) |
| HR (1) | HRP20130103T1 (hr) |
| MX (1) | MX2010001864A (hr) |
| PE (2) | PE20091369A1 (hr) |
| PL (1) | PL2195295T3 (hr) |
| PT (1) | PT2195295E (hr) |
| RU (1) | RU2436774C1 (hr) |
| TW (1) | TWI350284B (hr) |
| WO (1) | WO2009048236A1 (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP1000425A2 (en) | 2010-08-11 | 2012-03-28 | Richter Gedeon Nyrt | Process for the production of montelukast sodium |
| CN103570618A (zh) * | 2013-09-30 | 2014-02-12 | 浙江车头制药股份有限公司 | 一种孟鲁司特钠盐的制备方法 |
| CN105294556A (zh) * | 2014-06-06 | 2016-02-03 | 上海迪赛诺化学制药有限公司 | 一种制备孟鲁司特酸的方法 |
| KR20210042412A (ko) | 2018-09-06 | 2021-04-19 | 주식회사 이노파마스크린 | 천식 또는 파킨슨병 치료를 위한 방법 및 조성물 |
| KR102181155B1 (ko) * | 2019-09-26 | 2020-11-20 | 대봉엘에스 주식회사 | 이온성 액체를 매개로 한 에피나코나졸의 신규 제조방법 |
| CN111892535B (zh) * | 2020-08-27 | 2023-04-11 | 鲁南制药集团股份有限公司 | 一种孟鲁司特钠的合成方法 |
| CN111961083B (zh) * | 2020-08-27 | 2022-11-25 | 鲁南制药集团股份有限公司 | 一种孟鲁司特钠中间体化合物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19875039I2 (de) | 1990-10-12 | 2003-05-22 | Merck Frosst Canada Inc | Ungesaettigte Hydroxyalkylchinolinsaeuren als Leukotrien-Antagonisten |
| TW448160B (en) * | 1993-12-28 | 2001-08-01 | Merck & Co Inc | Novel dicyclohexylamine salt and process for the preparation of leukotriene antagonists |
| US5523477A (en) | 1995-01-23 | 1996-06-04 | Merck & Co., Inc. | Process for the preparation of 1-(thiomethyl)-cyclopropaneacetic acid |
| WO2005074935A1 (en) * | 2004-01-30 | 2005-08-18 | Teva Pharmaceutical Industries Ltd. | Montelukast free acid polymorphs |
| MXPA06012220A (es) | 2004-04-21 | 2007-07-18 | Teva Pharma | Procesos para preparar sodio de montelukast. |
| JP2006089463A (ja) * | 2004-08-24 | 2006-04-06 | Sumitomo Chemical Co Ltd | アリールエーテル類の製造方法 |
| WO2006064269A2 (en) * | 2004-12-17 | 2006-06-22 | Cipla Limited | Salts of leukotriene antagonist montelukast |
| GB0500029D0 (en) * | 2005-01-04 | 2005-02-09 | Univ Belfast | Basic ionic liquids |
| AU2006302237C1 (en) | 2005-10-07 | 2012-11-08 | The University Of Alabama | Multi-functional ionic liquid compositions |
| EP1783117A1 (en) | 2005-11-04 | 2007-05-09 | Esteve Quimica, S.A. | Process for the preparation of a leukotriene antagonist and intermediates thereof |
| EP1968943B1 (en) | 2005-12-13 | 2013-01-23 | MSN Laboratories Limited | An improved process for the preparation of montelukast and its pharmaceutically acceptable salts |
| US20090182148A1 (en) * | 2005-12-23 | 2009-07-16 | Harmander Singh Pal Chawla | Process for the manufacture of montelukast sodium |
| WO2007096889A2 (en) * | 2006-02-27 | 2007-08-30 | Chemagis Ltd. | Process for preparing montelukast and salts thereof |
| KR100774088B1 (ko) | 2006-12-14 | 2007-11-06 | 한미약품 주식회사 | 몬테루카스트의 제조방법 및 이에 사용되는 중간체 |
-
2007
- 2007-10-09 KR KR1020070101486A patent/KR101072896B1/ko active IP Right Grant
-
2008
- 2008-10-01 PL PL08838092T patent/PL2195295T3/pl unknown
- 2008-10-01 JP JP2010528789A patent/JP5210389B2/ja not_active Expired - Fee Related
- 2008-10-01 WO PCT/KR2008/005794 patent/WO2009048236A1/en active Application Filing
- 2008-10-01 DK DK08838092.8T patent/DK2195295T3/da active
- 2008-10-01 CA CA2701912A patent/CA2701912C/en not_active Expired - Fee Related
- 2008-10-01 MX MX2010001864A patent/MX2010001864A/es active IP Right Grant
- 2008-10-01 CN CN2008801090046A patent/CN101808998B/zh not_active Expired - Fee Related
- 2008-10-01 RU RU2010118618/04A patent/RU2436774C1/ru not_active IP Right Cessation
- 2008-10-01 ES ES08838092T patent/ES2398732T3/es active Active
- 2008-10-01 EP EP08838092A patent/EP2195295B1/en not_active Not-in-force
- 2008-10-01 PT PT88380928T patent/PT2195295E/pt unknown
- 2008-10-01 US US12/674,118 patent/US8426599B2/en not_active Expired - Fee Related
- 2008-10-08 AR ARP080104395A patent/AR068755A1/es unknown
- 2008-10-08 TW TW097138680A patent/TWI350284B/zh not_active IP Right Cessation
- 2008-10-09 PE PE2008001742A patent/PE20091369A1/es not_active Application Discontinuation
- 2008-10-09 PE PE2013000260A patent/PE20131219A1/es not_active Application Discontinuation
- 2008-10-09 CL CL2008002996A patent/CL2008002996A1/es unknown
-
2013
- 2013-02-06 HR HRP20130103AT patent/HRP20130103T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2195295B1 (en) | 2013-01-23 |
| KR20090036349A (ko) | 2009-04-14 |
| JP2011500555A (ja) | 2011-01-06 |
| DK2195295T3 (da) | 2013-05-06 |
| US8426599B2 (en) | 2013-04-23 |
| CA2701912A1 (en) | 2009-04-16 |
| MX2010001864A (es) | 2010-03-15 |
| PT2195295E (pt) | 2013-02-28 |
| PL2195295T3 (pl) | 2013-06-28 |
| CA2701912C (en) | 2013-04-02 |
| KR101072896B1 (ko) | 2011-10-17 |
| ES2398732T3 (es) | 2013-03-21 |
| PE20131219A1 (es) | 2013-11-16 |
| TWI350284B (en) | 2011-10-11 |
| US20110105757A1 (en) | 2011-05-05 |
| CN101808998B (zh) | 2012-10-24 |
| JP5210389B2 (ja) | 2013-06-12 |
| CN101808998A (zh) | 2010-08-18 |
| CL2008002996A1 (es) | 2009-04-13 |
| EP2195295A1 (en) | 2010-06-16 |
| PE20091369A1 (es) | 2009-10-01 |
| EP2195295A4 (en) | 2011-04-13 |
| TW200920737A (en) | 2009-05-16 |
| WO2009048236A1 (en) | 2009-04-16 |
| AR068755A1 (es) | 2009-12-02 |
| RU2436774C1 (ru) | 2011-12-20 |
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