WO2007013097A8 - Improved process for the preparation of ibandronate sodium - Google Patents
Improved process for the preparation of ibandronate sodiumInfo
- Publication number
- WO2007013097A8 WO2007013097A8 PCT/IN2006/000251 IN2006000251W WO2007013097A8 WO 2007013097 A8 WO2007013097 A8 WO 2007013097A8 IN 2006000251 W IN2006000251 W IN 2006000251W WO 2007013097 A8 WO2007013097 A8 WO 2007013097A8
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- acid
- ibandronate
- gave
- preparation
- Prior art date
Links
- MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 5
- 229960005236 ibandronic acid Drugs 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 229940015872 ibandronate Drugs 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 abstract 1
- 229940078581 Bone resorption inhibitor Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 238000010960 commercial process Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000005954 phosphonylation reaction Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Present invention discloses an improved and commercial process for the preparation of ibandronic acid or its monosodium salt. According to the process 3-N-methylaminopropionitrile is reacted with n-pentylbromide to get the tertiary amine of formula-II. Hydrolysis of the nitrile compound of formula-II with hydrochloric acid gave the b-alanine derivative of formula-X. Bis-phosphonylation of the acid compound of formula-X with phorphorous trichloride and phosphorous acid, followed by water hydrolysis gave aqueous ibandronic acid. Treatment of this with sodium hydroxide, followed by dilution of the aqueous solution with methanol gave ibandronate monosodium of formula-Ia as white crystalline solid. Present process utilizes simple raw materials and avoids the column chromatography technique used in the prior art process for isolation of ibandronic acid. Overall yield of ibandronate is more than 60% from the nitrile intermediate of formula-II. Ibandronate is widely used as bone resorption inhibitor.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN996CH2005 | 2005-07-25 | ||
| IN996/CHE/2005 | 2005-07-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2007013097A1 WO2007013097A1 (en) | 2007-02-01 |
| WO2007013097A8 true WO2007013097A8 (en) | 2007-12-06 |
Family
ID=37390836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2006/000251 WO2007013097A1 (en) | 2005-07-25 | 2006-07-17 | Improved process for the preparation of ibandronate sodium |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2007013097A1 (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007074475A2 (en) * | 2005-12-27 | 2007-07-05 | Natco Pharma Limited | Novel polymorphic forms of ibandronate |
| EP1966227A1 (en) * | 2006-11-16 | 2008-09-10 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of ibandronate sodium |
| PL2144919T3 (en) * | 2007-04-11 | 2016-05-31 | Hoffmann La Roche | Multi step synthesis of ibandronate |
| WO2008131160A1 (en) * | 2007-04-19 | 2008-10-30 | Dr. Reddy's Laboratories Ltd. | Ibandronate sodium polymorphs |
| CA2689504A1 (en) * | 2007-06-19 | 2008-12-24 | Albemarle Corporation | Processes for manufacturing bisphosphonic acids |
| US20090042839A1 (en) * | 2007-08-09 | 2009-02-12 | Sharon Avhar-Maydan | Crystalline forms of ibandronate sodium |
| WO2009093258A2 (en) * | 2008-01-24 | 2009-07-30 | Fleming Laboratories Limited | A new and improved process for the preparation of ibandronate sodium monohydrate |
| CN101279985B (en) * | 2008-06-02 | 2012-09-05 | 苏州汉德森医药科技有限公司 | Synthetic method of ibandronate |
| WO2012007021A1 (en) * | 2010-07-14 | 2012-01-19 | Pharmathen S.A. | Process for the preparation of 3-(n-methyl-n-pentyl)amino-1-hydroxypropane-1,1-diphosphonic acid salt or derivatives thereof |
| CN103030661B (en) * | 2012-11-16 | 2015-12-02 | 湖南方盛制药股份有限公司 | The preparation method of ibronate sodium |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3623397A1 (en) * | 1986-07-11 | 1988-01-14 | Boehringer Mannheim Gmbh | NEW DIPHOSPHONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
-
2006
- 2006-07-17 WO PCT/IN2006/000251 patent/WO2007013097A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007013097A1 (en) | 2007-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2007013097A8 (en) | Improved process for the preparation of ibandronate sodium | |
| MX2007005114A (en) | Process for the preparation of ibandronate. | |
| BRPI0607092A2 (en) | 3- (n-methyl-n-pentyl) amino-1-hydroxypropane-1,1-diphosphonic acid monosodium salt monohydrate crystalline polymorph, process for the preparation of a crystalline ibandronate polymorph, and pharmaceutical composition which understand | |
| ES2324015T1 (en) | SYNTHESIS PROCESS OF GEMINAL BISPHOSPHONIC ACIDS OR THEIR PHARMACEUTICALLY ACCEPTABLE SALTS OR THEIR HYDRATS. | |
| TW200640940A (en) | Ibandronate polymorph B | |
| WO2008007392A3 (en) | Process for the preparation of tenofovir | |
| IL172513A0 (en) | Zoledronic acid crystal forms, zoledronate sodium salt crystal forms, amorphous zoledronate sodium salt, and processes for their preparation | |
| CA2281922A1 (en) | Melamine melam melem double salt of a polyphosphoric acid and process for its production | |
| PL1656386T3 (en) | A process for preparation of bisphosphonic acid compounds | |
| HRP20080619T3 (en) | Process for the preparation of [1-hydroxy-2-(3-pyridinyl)ethyliden]bisphosphonic acid and hemi-pentahydrate monosodium salt thereof | |
| WO2007074475A3 (en) | Novel polymorphic forms of ibandronate | |
| HRP20120958T1 (en) | Processes for preparing a substituted gamma-amino acid | |
| ES2153794A1 (en) | Process for producing 4-amino-1-hidroxybutylidene-1,1-bisphosphonic acid and its trihydrated monosodic salt | |
| CA2570461A1 (en) | Process for the preparation of gabapentin | |
| AU606516B2 (en) | Process for the preparation of n-phosphonomethylglycine | |
| AU5372299A (en) | A process for the preparation of zofenopril calcium salt | |
| ES2200921T3 (en) | PROCESS FOR PREPARATION OF METHYLENE-BISPHOSPHONIC ACIDS AND ITS SALTS. | |
| WO2007083243A3 (en) | An improved process for the preparation of risedronate sodium hemi-pentahydrate | |
| IL201307A (en) | Process for the preparation of ibandronate | |
| US5750774A (en) | Method for producing N-phosphonomethylglycine | |
| EP0816369B1 (en) | Method for producing N-phosphonomethylglycine | |
| TW200600450A (en) | Purification method of phosphoric acid | |
| TW200736268A (en) | Synthesis of alendronate sodium trihydrate | |
| JP4330097B2 (en) | 2- (Hydroxycarbonyl) ethyl-3-amino-3- (hydroxycarbonyl) propylphosphinic acid and method for producing the same | |
| WO2008065542A2 (en) | An improved process for the preparation of risedronate sodium |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| NENP | Non-entry into the national phase in: |
Ref country code: DE |
|
| WWW | Wipo information: withdrawn in national office |
Country of ref document: DE |
|
| 122 | Ep: pct app. not ent. europ. phase |
Ref document number: 06780533 Country of ref document: EP Kind code of ref document: A1 |