WO2009093258A3 - A new and improved process for the preparation of ibandronate sodium monohydrate - Google Patents
A new and improved process for the preparation of ibandronate sodium monohydrate Download PDFInfo
- Publication number
- WO2009093258A3 WO2009093258A3 PCT/IN2008/000454 IN2008000454W WO2009093258A3 WO 2009093258 A3 WO2009093258 A3 WO 2009093258A3 IN 2008000454 W IN2008000454 W IN 2008000454W WO 2009093258 A3 WO2009093258 A3 WO 2009093258A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- methyl
- preparation
- new
- improved process
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- VBDRTGFACFYFCT-UHFFFAOYSA-M sodium;hydroxy-[(1r)-1-hydroxy-3-[methyl(pentyl)amino]-1-phosphonopropyl]phosphinate;hydrate Chemical compound O.[Na+].CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)([O-])=O VBDRTGFACFYFCT-UHFFFAOYSA-M 0.000 title abstract 3
- YDWXRULMHQZBEX-UHFFFAOYSA-N 3-[methyl(pentyl)amino]propanoic acid;hydrochloride Chemical compound Cl.CCCCCN(C)CCC(O)=O YDWXRULMHQZBEX-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 abstract 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- YQEMKWHTUQTZKV-UHFFFAOYSA-N ethyl 3-(pentylamino)propanoate Chemical compound CCCCCNCCC(=O)OCC YQEMKWHTUQTZKV-UHFFFAOYSA-N 0.000 abstract 1
- GXFODLVRWQVTIF-UHFFFAOYSA-N ethyl 3-[methyl(pentyl)amino]propanoate Chemical compound CCCCCN(C)CCC(=O)OCC GXFODLVRWQVTIF-UHFFFAOYSA-N 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 229940100684 pentylamine Drugs 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-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
Classifications
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- 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
- C07F9/386—Polyphosphonic acids containing hydroxy substituents in the hydrocarbon radicals
-
- 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
The present invention discloses a new and an improved process for preparation of Ibandronate sodium monohydrate. According to the process pentylamine is reacted with ethylacrylate to give N-pentyl-β-alanine ethyl ester (XXIV), which on methylation provided N-methyl-N-pentyl-β-alanine ethylester formula (XXV). The reresulting ester on hydrolysis and subsequent treatment with hydrochloric acid furnished 3-(N-methyl-N-pentylamino)propionic acid hydrochloride formula (II). Bisphosphorylation of 3-(N-methyl-N-pentylamino)propionic acid hydrochloride formula (II) with phosphorous acid and phosphorous trichloride followed by hydrolysis and subsequent treatment with a base provided Ibandronate monosodium monohydrate of formula (I).
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN189CH2008 | 2008-01-24 | ||
| IN189/CHE/2008 | 2008-01-24 | ||
| IN679CH2008 | 2008-03-19 | ||
| IN679/CHE/2008 | 2008-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2009093258A2 WO2009093258A2 (en) | 2009-07-30 |
| WO2009093258A3 true WO2009093258A3 (en) | 2011-01-20 |
Family
ID=40901513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2008/000454 WO2009093258A2 (en) | 2008-01-24 | 2008-07-16 | A new and improved process for the preparation of ibandronate sodium monohydrate |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2009093258A2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011016738A1 (en) * | 2009-08-05 | 2011-02-10 | Zaklady Farmaceutyczne Polpharma Sa | A process for the synthesis of 1-hydroxy-3-(n-methylpentylamino) propylidene bisphosphonic acid monosodium salt, monohydrate |
| EP2609101B1 (en) | 2010-07-14 | 2015-01-28 | Pharmathen S.A. | Process for the preparation of 3-(n-methyl-n-pentyl)amino-1-hydroxypropane-1,1-diphosphonic acid salt or derivatives thereof |
| CN103450064A (en) * | 2013-07-30 | 2013-12-18 | 中国科学院上海微系统与信息技术研究所 | Preparation method for aryl vinyl propylene imide and detection method for primary amine |
| CN103396332A (en) * | 2013-08-19 | 2013-11-20 | 四川协力制药有限公司 | 3-[(N-methyl-N-pentyl)amino]propionic acid hydrochloride preparation method |
| CN109608492B (en) * | 2018-12-19 | 2021-02-09 | 深圳市第二人民医院 | Diphosphonic acid compound for osteoporosis and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0252504A1 (en) * | 1986-07-11 | 1988-01-13 | Roche Diagnostics GmbH | Diphosphonic-acid derivatives, process for their preparation and medicines containing these compounds |
| WO2006045578A2 (en) * | 2004-10-29 | 2006-05-04 | F. Hoffmann-La Roche Ag | Process for the preparation of ibandronate |
| WO2007013097A1 (en) * | 2005-07-25 | 2007-02-01 | Natco Pharma Limited | Improved process for the preparation of ibandronate sodium |
-
2008
- 2008-07-16 WO PCT/IN2008/000454 patent/WO2009093258A2/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0252504A1 (en) * | 1986-07-11 | 1988-01-13 | Roche Diagnostics GmbH | Diphosphonic-acid derivatives, process for their preparation and medicines containing these compounds |
| WO2006045578A2 (en) * | 2004-10-29 | 2006-05-04 | F. Hoffmann-La Roche Ag | Process for the preparation of ibandronate |
| WO2007013097A1 (en) * | 2005-07-25 | 2007-02-01 | Natco Pharma Limited | Improved process for the preparation of ibandronate sodium |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009093258A2 (en) | 2009-07-30 |
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