ES2060541A1 - New procedure for the synthesis of a derivative of 2-(2- pyridylmethylsulphinyl)benzimidazole, and new intermediate products obtained therewith - Google Patents
New procedure for the synthesis of a derivative of 2-(2- pyridylmethylsulphinyl)benzimidazole, and new intermediate products obtained therewithInfo
- Publication number
- ES2060541A1 ES2060541A1 ES09300384A ES9300384A ES2060541A1 ES 2060541 A1 ES2060541 A1 ES 2060541A1 ES 09300384 A ES09300384 A ES 09300384A ES 9300384 A ES9300384 A ES 9300384A ES 2060541 A1 ES2060541 A1 ES 2060541A1
- Authority
- ES
- Spain
- Prior art keywords
- benzimidazole
- methyl
- new
- pyridylmethylsulphinyl
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract 3
- HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000013067 intermediate product Substances 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- CFMTVTYBZMKULI-UHFFFAOYSA-N 2,3-dimethyl-4-nitro-1-oxidopyridin-1-ium Chemical compound CC1=C(C)[N+]([O-])=CC=C1[N+]([O-])=O CFMTVTYBZMKULI-UHFFFAOYSA-N 0.000 abstract 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 abstract 1
- 238000010586 diagram Methods 0.000 abstract 1
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 abstract 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The method according to the invention is a multi-step process (Diagram 1) for preparing 2-(((3-methyl-4-(2,2,2- trifluoroethoxy)-2-pyridyl)methyl)sulphinyl)-1H- benzimidazole which comprises the following steps: step a): nucleophilic substitution of the Z group of 2- (((3-methyl-4-Z-2-pyridyl)methyl)sulphinyl)-1H- benzimidazole by 2,2,2-trifluoroethanol step b): obtaining 2-(((3-methyl-4-Z-2- pyridyl)methyl)sulphinyl)-1H-benzimidazole by oxidation of 2-(((3-methyl-4-Z-2-pyridyl)methyl)thio)-1H- benzimidazole step c): preparation of 2-(((3-methyl-4-Z-2- pyridyl)methyl)thio)-1H-benzimidazole from 2,3-dimethyl-4- nitropyridine N-oxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9300384A ES2060541B1 (en) | 1993-02-26 | 1993-02-26 | NEW PROCEDURE FOR THE SYNTHESIS OF A DERIVATIVE OF 2- (2-PIRIDILMETILSUFINIL) BENCIMIDAZOLE, AND NEW INTERMEDIATE PRODUCTS OBTAINED WITH THE SAME. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9300384A ES2060541B1 (en) | 1993-02-26 | 1993-02-26 | NEW PROCEDURE FOR THE SYNTHESIS OF A DERIVATIVE OF 2- (2-PIRIDILMETILSUFINIL) BENCIMIDAZOLE, AND NEW INTERMEDIATE PRODUCTS OBTAINED WITH THE SAME. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2060541A1 true ES2060541A1 (en) | 1994-11-16 |
| ES2060541B1 ES2060541B1 (en) | 1995-11-16 |
Family
ID=8280919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9300384A Expired - Fee Related ES2060541B1 (en) | 1993-02-26 | 1993-02-26 | NEW PROCEDURE FOR THE SYNTHESIS OF A DERIVATIVE OF 2- (2-PIRIDILMETILSUFINIL) BENCIMIDAZOLE, AND NEW INTERMEDIATE PRODUCTS OBTAINED WITH THE SAME. |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2060541B1 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001004109A1 (en) * | 1999-07-14 | 2001-01-18 | Quimica Sintetica, S.A. | Process for the production of 2-(2-pyridinylmethylsulphinyl)-1h-benzimidazoles |
| WO2001068594A1 (en) * | 2000-03-13 | 2001-09-20 | Esteve Quimica, S.A. | Method for oxidizing a thioether group into a sulfoxide group |
| WO2002028852A1 (en) * | 2000-10-02 | 2002-04-11 | Dinamite Dipharma | A process for the preparation of pantoprazole and intermediates therefor |
| ES2187248A1 (en) * | 2000-08-25 | 2003-05-16 | Sint Quimica Sa | Procedure is for obtaining derivatives of 2-(2-pyridinyl methyl-sulphinyl)-benzimidazole to be used in treatment or prevention of peptic ulcers |
| EP1334956A3 (en) * | 2002-02-07 | 2004-02-11 | Sumitomo Chemical Company, Limited | Method for preparing sulfone or sulfoxide compound |
| WO2005054228A1 (en) * | 2003-12-05 | 2005-06-16 | Hetero Drugs Limited | A process for the preparation of substitited pyridinylmethylsulfinyl- benzimidazole enantiomers |
| ES2264362A1 (en) * | 2004-12-22 | 2006-12-16 | Laboratorios Viñas S.A. | Procedure is for obtaining derivatives of 2-(2-) pyridinil-methylsulfinil-1H-benzimidazols of general formula useful as inhibitors of acid secretion or as anti-ulcerous agents |
| WO2009010937A1 (en) | 2007-07-17 | 2009-01-22 | Ranbaxy Laboratories Limited | Process for the preparation op pantoprazole sodium and pantoprazole sodium sesquihydrate |
| ITMI20082046A1 (en) * | 2008-11-18 | 2010-05-19 | Dipharma Francis Srl | PROCEDURE FOR THE PREPARATION OF DEXLANSOPRAZOL |
| US8314241B2 (en) | 2009-07-29 | 2012-11-20 | Dipharma Francis S.R.L. | Process for the preparation of crystalline dexlansoprazole |
| US20160230010A1 (en) * | 2013-10-25 | 2016-08-11 | Toyo Kohan Co., Ltd. | Nonlinear optical dye, photorefractive material composition, photorefractive substrate and hologram recording medium |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2343935B1 (en) * | 2008-12-29 | 2011-04-28 | Laboratorios Viñas S.A. | USEFUL INTERMEDIATES FOR OBTAINING 2- (2-PIRIDINILMETILSULFINIL) -1H-BENZIMIDAZOLES AND CORRESPONDING PROCEDURES. |
| ES2363075B1 (en) * | 2009-12-23 | 2012-03-27 | Laboratorios Viñas S.A. | Procedure for obtaining 4-chloro-2-chloromethyl-3-methylpyridine |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8404993A1 (en) * | 1982-08-26 | 1984-05-16 | Haessle Ab | Intermediates for the preparation of omeprazole. |
| ES8607288A1 (en) * | 1984-08-16 | 1986-05-16 | Takeda Chemical Industries Ltd | Pyridine derivatives and their production. |
| EP0302720A1 (en) * | 1987-08-04 | 1989-02-08 | Takeda Chemical Industries, Ltd. | Production of 2-(2-Pyridylmethylsulfinyl)-benzimidazole compounds |
| ES2023609A6 (en) * | 1990-11-29 | 1992-01-16 | Inke Sa | Process for obtaining 2-[[[3-methyl-4-(2,2,2- trifluoroethoxy)-2-pyridinyl]methyl]sulphinyl]-1H- benzimidazole |
| ES2036948A1 (en) * | 1991-11-21 | 1993-06-01 | Genesis Para La Investigacion | Procedure for obtaining compounds derived from pyridine. |
-
1993
- 1993-02-26 ES ES9300384A patent/ES2060541B1/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8404993A1 (en) * | 1982-08-26 | 1984-05-16 | Haessle Ab | Intermediates for the preparation of omeprazole. |
| ES8607288A1 (en) * | 1984-08-16 | 1986-05-16 | Takeda Chemical Industries Ltd | Pyridine derivatives and their production. |
| EP0302720A1 (en) * | 1987-08-04 | 1989-02-08 | Takeda Chemical Industries, Ltd. | Production of 2-(2-Pyridylmethylsulfinyl)-benzimidazole compounds |
| ES2023609A6 (en) * | 1990-11-29 | 1992-01-16 | Inke Sa | Process for obtaining 2-[[[3-methyl-4-(2,2,2- trifluoroethoxy)-2-pyridinyl]methyl]sulphinyl]-1H- benzimidazole |
| ES2036948A1 (en) * | 1991-11-21 | 1993-06-01 | Genesis Para La Investigacion | Procedure for obtaining compounds derived from pyridine. |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001004109A1 (en) * | 1999-07-14 | 2001-01-18 | Quimica Sintetica, S.A. | Process for the production of 2-(2-pyridinylmethylsulphinyl)-1h-benzimidazoles |
| ES2166269A1 (en) * | 1999-07-14 | 2002-04-01 | Sint Quimica Sa | Process for the production of 2-(2-pyridinylmethylsulphinyl)-1h-benzimidazoles |
| WO2001068594A1 (en) * | 2000-03-13 | 2001-09-20 | Esteve Quimica, S.A. | Method for oxidizing a thioether group into a sulfoxide group |
| ES2163372A1 (en) * | 2000-03-13 | 2002-01-16 | Esteve Quimica Sa | Method for oxidizing a thioether group into a sulfoxide group |
| US6603009B2 (en) | 2000-03-13 | 2003-08-05 | Esteve Quimica, S.A. | Method for oxidizing a thioether group into a sulfoxide group |
| ES2187248A1 (en) * | 2000-08-25 | 2003-05-16 | Sint Quimica Sa | Procedure is for obtaining derivatives of 2-(2-pyridinyl methyl-sulphinyl)-benzimidazole to be used in treatment or prevention of peptic ulcers |
| WO2002028852A1 (en) * | 2000-10-02 | 2002-04-11 | Dinamite Dipharma | A process for the preparation of pantoprazole and intermediates therefor |
| ES2185459A1 (en) * | 2000-10-02 | 2003-04-16 | Dinamite Dipharma Spa | A process for the preparation of pantoprazole and intermediates therefor |
| EP1334956A3 (en) * | 2002-02-07 | 2004-02-11 | Sumitomo Chemical Company, Limited | Method for preparing sulfone or sulfoxide compound |
| US6916938B2 (en) | 2002-02-07 | 2005-07-12 | Sumitomo Chemical Company, Limited | Method for preparing sulfone or sulfoxide compound |
| WO2005054228A1 (en) * | 2003-12-05 | 2005-06-16 | Hetero Drugs Limited | A process for the preparation of substitited pyridinylmethylsulfinyl- benzimidazole enantiomers |
| ES2264362A1 (en) * | 2004-12-22 | 2006-12-16 | Laboratorios Viñas S.A. | Procedure is for obtaining derivatives of 2-(2-) pyridinil-methylsulfinil-1H-benzimidazols of general formula useful as inhibitors of acid secretion or as anti-ulcerous agents |
| ES2264362B1 (en) * | 2004-12-22 | 2007-11-01 | Laboratorios Viñas S.A. | "PROCEDURE FOR OBTAINING DERIVATIVES OF 2- (2-PIRIDINILMETILSUFINIL-1H-BENZIMIDAZOLES"). |
| WO2009010937A1 (en) | 2007-07-17 | 2009-01-22 | Ranbaxy Laboratories Limited | Process for the preparation op pantoprazole sodium and pantoprazole sodium sesquihydrate |
| ITMI20082046A1 (en) * | 2008-11-18 | 2010-05-19 | Dipharma Francis Srl | PROCEDURE FOR THE PREPARATION OF DEXLANSOPRAZOL |
| US8198455B2 (en) | 2008-11-18 | 2012-06-12 | Dipharma Francis S.R.L. | Process for the preparation of dexlansoprazole |
| US8314241B2 (en) | 2009-07-29 | 2012-11-20 | Dipharma Francis S.R.L. | Process for the preparation of crystalline dexlansoprazole |
| US20160230010A1 (en) * | 2013-10-25 | 2016-08-11 | Toyo Kohan Co., Ltd. | Nonlinear optical dye, photorefractive material composition, photorefractive substrate and hologram recording medium |
| US9902858B2 (en) * | 2013-10-25 | 2018-02-27 | Toyo Kohan Co., Ltd. | Nonlinear optical dye, photorefractive material composition, photorefractive substrate and hologram recording medium |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2060541B1 (en) | 1995-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD2A | Announcement of lapse in spain |
Effective date: 20141120 |