SI21236A - Postopek kristalizacije losartan kalija - Google Patents
Postopek kristalizacije losartan kalija Download PDFInfo
- Publication number
- SI21236A SI21236A SI200120042A SI200120042A SI21236A SI 21236 A SI21236 A SI 21236A SI 200120042 A SI200120042 A SI 200120042A SI 200120042 A SI200120042 A SI 200120042A SI 21236 A SI21236 A SI 21236A
- Authority
- SI
- Slovenia
- Prior art keywords
- losartan
- potassium
- acetone
- methanol
- losartan potassium
- Prior art date
Links
- 239000002083 C09CA01 - Losartan Substances 0.000 title claims abstract description 45
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 229960000519 losartan potassium Drugs 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002425 crystallisation Methods 0.000 title description 4
- 230000008025 crystallization Effects 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 55
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 50
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 239000012296 anti-solvent Substances 0.000 claims abstract description 7
- QQPGGBNMTNDKEY-UHFFFAOYSA-N [2-butyl-5-chloro-3-[[4-[2-(2-trityltetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NN(N=N2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 QQPGGBNMTNDKEY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 3
- -1 triphenylmethyl (trityl) protecting group Chemical group 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 229960004773 losartan Drugs 0.000 abstract description 18
- 150000001875 compounds Chemical class 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 abstract 1
- PSIFNNKUMBGKDQ-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 PSIFNNKUMBGKDQ-UHFFFAOYSA-N 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 2
- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- RBWFVUDBNNXTFZ-UHFFFAOYSA-N 1h-imidazole;potassium Chemical compound [K].C1=CNC=N1 RBWFVUDBNNXTFZ-UHFFFAOYSA-N 0.000 description 1
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 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
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
- 238000001237 Raman spectrum Methods 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN403CH2001 | 2001-05-18 | ||
| PCT/IN2001/000205 WO2002094816A1 (en) | 2001-05-18 | 2001-11-20 | Process for the crystallization of losartan potassium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI21236A true SI21236A (sl) | 2003-12-31 |
Family
ID=11097003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI200120042A SI21236A (sl) | 2001-05-18 | 2001-11-20 | Postopek kristalizacije losartan kalija |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1294712A1 (OSRAM) |
| JP (1) | JP2004520446A (OSRAM) |
| BG (1) | BG107478A (OSRAM) |
| SI (1) | SI21236A (OSRAM) |
| SK (1) | SK722003A3 (OSRAM) |
| WO (1) | WO2002094816A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030135041A1 (en) | 2002-01-04 | 2003-07-17 | Orchid Chemicals & Pharmaceuticals Limited, India | Synthesis of ceftiofur intermediate |
| WO2004039352A2 (en) * | 2002-10-31 | 2004-05-13 | Ranbaxy Laboratories Limited | Amorphous form of losartan potassium |
| ITMI20030328A1 (it) * | 2003-02-25 | 2004-08-26 | Dinamite Dipharma S P A In Forma A Bbreviata Diph | Polimorfi di losartan potassio e procedimento per la loro preparazione. |
| WO2004076442A1 (en) * | 2003-02-28 | 2004-09-10 | Ranbaxy Laboratories Limited | Polymorphs of losartan |
| AU2003269470A1 (en) * | 2003-04-03 | 2004-10-25 | Ipca Laboratories Limited | A process for the synthesis of losartan potassium |
| US7345071B2 (en) | 2003-05-07 | 2008-03-18 | Ipca Laboratories Limited | Process for the synthesis of Losartan potassium |
| PL1658281T3 (pl) * | 2003-08-27 | 2010-12-31 | Zentiva Ks | Sposób usuwania trifenylometanowej grupy zabezpieczającej |
| ITMI20032472A1 (it) * | 2003-12-16 | 2005-06-17 | Dinamite Dipharma S P A In Forma A Bbreviata Diph | Procedimento per la preparazione di losartan potassio cristallino |
| EP1709034A2 (en) * | 2004-01-06 | 2006-10-11 | IPCA Laboratories Limited | An improved process for the synthesis of losartan potassium |
| US7692023B2 (en) | 2004-02-11 | 2010-04-06 | Teva Pharmaceutical Industries Ltd. | Candesartan cilexetil polymorphs |
| EP1729766A1 (en) * | 2004-03-01 | 2006-12-13 | LEK Pharmaceuticals D.D. | Pharmaceutical formulation |
| KR100908308B1 (ko) * | 2004-05-05 | 2009-07-17 | 테바 파마슈티컬 인더스트리즈 리미티드 | 순도가 높은 칸데사르탄 실렉세틸의 제조 |
| WO2010046804A2 (en) * | 2008-10-21 | 2010-04-29 | Alembic Limited | A process for preparation of losartan potassium form i |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5138069A (en) * | 1986-07-11 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| EP1384717B1 (en) * | 1991-11-18 | 2008-05-14 | E.I. Dupont De Nemours And Company | 2-(2'-triphenylmethyl-2'H-tetrazol-5'-yl)phenylboronic acid intermediates for the synthesis of A II receptor antagonists |
| ATE214388T1 (de) * | 1996-10-29 | 2002-03-15 | Merck & Co Inc | Verfahren zur kristallisation von losartan |
| HU222773B1 (hu) * | 2000-04-21 | 2003-10-28 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás egy ismert tetrazolszármazék előállítására |
-
2001
- 2001-11-20 JP JP2002591489A patent/JP2004520446A/ja active Pending
- 2001-11-20 SI SI200120042A patent/SI21236A/sl not_active IP Right Cessation
- 2001-11-20 WO PCT/IN2001/000205 patent/WO2002094816A1/en not_active Ceased
- 2001-11-20 EP EP01274254A patent/EP1294712A1/en not_active Withdrawn
- 2001-11-20 SK SK72-2003A patent/SK722003A3/sk unknown
-
2003
- 2003-01-17 BG BG107478A patent/BG107478A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG107478A (bg) | 2004-01-30 |
| EP1294712A1 (en) | 2003-03-26 |
| WO2002094816A1 (en) | 2002-11-28 |
| JP2004520446A (ja) | 2004-07-08 |
| SK722003A3 (en) | 2003-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF | Valid on the event date | ||
| KO00 | Lapse of patent |
Effective date: 20050822 |