CA2646368A1 - Substantially pure o-desmethylvenlafaxine and processes for preparing it - Google Patents
Substantially pure o-desmethylvenlafaxine and processes for preparing it Download PDFInfo
- Publication number
- CA2646368A1 CA2646368A1 CA002646368A CA2646368A CA2646368A1 CA 2646368 A1 CA2646368 A1 CA 2646368A1 CA 002646368 A CA002646368 A CA 002646368A CA 2646368 A CA2646368 A CA 2646368A CA 2646368 A1 CA2646368 A1 CA 2646368A1
- Authority
- CA
- Canada
- Prior art keywords
- desmethylvenlafaxine
- substantially pure
- preparing
- mixture
- desmethylvenlafaxine according
- 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.)
- Abandoned
Links
- KYYIDSXMWOZKMP-UHFFFAOYSA-N O-desmethylvenlafaxine Chemical compound C1CCCCC1(O)C(CN(C)C)C1=CC=C(O)C=C1 KYYIDSXMWOZKMP-UHFFFAOYSA-N 0.000 title claims abstract description 132
- 238000000034 method Methods 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 claims description 102
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 60
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 55
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 51
- 238000004519 manufacturing process Methods 0.000 claims description 51
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims description 47
- 229960004688 venlafaxine Drugs 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 42
- 239000012535 impurity Substances 0.000 claims description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 36
- 239000003480 eluent Substances 0.000 claims description 36
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 238000003556 assay Methods 0.000 claims description 24
- BHCUWXACHAFFSK-UHFFFAOYSA-N 4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenol Chemical compound C1CCCCC1(O)C(CN)C1=CC=C(O)C=C1 BHCUWXACHAFFSK-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 239000000725 suspension Substances 0.000 claims description 20
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 17
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
- -1 C1-C8 alkyl thiolate Chemical class 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 13
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
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- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 239000001384 succinic acid Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 6
- 150000007944 thiolates Chemical class 0.000 claims description 6
- 239000012296 anti-solvent Substances 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- XRZRPHKMCVBSLA-UHFFFAOYSA-M sodium;dodecane-1-thiolate Chemical group [Na+].CCCCCCCCCCCC[S-] XRZRPHKMCVBSLA-UHFFFAOYSA-M 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
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- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000011877 solvent mixture Substances 0.000 claims 2
- 230000001335 demethylating effect Effects 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000007787 solid Substances 0.000 description 31
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- 238000002360 preparation method Methods 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 235000015165 citric acid Nutrition 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 9
- 239000008187 granular material Substances 0.000 description 8
- 210000003739 neck Anatomy 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- 108010010803 Gelatin Proteins 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
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- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 3
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79280106P | 2006-04-17 | 2006-04-17 | |
| US60/792,801 | 2006-04-17 | ||
| US79673906P | 2006-05-01 | 2006-05-01 | |
| US60/796,739 | 2006-05-01 | ||
| US87295506P | 2006-12-04 | 2006-12-04 | |
| US60/872,955 | 2006-12-04 | ||
| US89916607P | 2007-02-01 | 2007-02-01 | |
| US60/899,166 | 2007-02-01 | ||
| US90241807P | 2007-02-20 | 2007-02-20 | |
| US60/902,418 | 2007-02-20 | ||
| US90398807P | 2007-02-27 | 2007-02-27 | |
| US60/903,988 | 2007-02-27 | ||
| PCT/US2007/009558 WO2007120923A1 (en) | 2006-04-17 | 2007-04-17 | Substantially pure o-desmethylvenlafaxine and processes for preparing it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2646368A1 true CA2646368A1 (en) | 2007-10-25 |
Family
ID=39750904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002646368A Abandoned CA2646368A1 (en) | 2006-04-17 | 2007-04-17 | Substantially pure o-desmethylvenlafaxine and processes for preparing it |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2007708A1 (de) |
| JP (1) | JP2008546718A (de) |
| CA (1) | CA2646368A1 (de) |
| IL (1) | IL193398A0 (de) |
| MX (1) | MX2007016172A (de) |
| WO (1) | WO2007120923A1 (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2007016179A (es) | 2006-04-17 | 2008-03-11 | Teva Pharma | Formas cristalinas de o-desmetilvenlafaxina. |
| WO2008035369A2 (en) * | 2006-06-30 | 2008-03-27 | Alembic Limited | Novel form of o-desmethyl venlafaxine |
| CA2656285A1 (en) * | 2006-07-26 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Processes for the synthesis of o-desmethylvenlafaxine |
| EP1934168A2 (de) | 2006-07-26 | 2008-06-25 | Teva Pharmaceutical Industries Ltd | Tridesmethylvenlafaxin und verfahren zur synthese von o-desmethylvenlafaxin |
| US20090069601A1 (en) * | 2006-07-26 | 2009-03-12 | Valerie Niddam-Hildesheim | Processes for the synthesis of O-desmethylvenlafaxine |
| EP2061750A2 (de) * | 2006-08-04 | 2009-05-27 | Medichem, S.A. | Verbessertes verfahren zur synthetisierung einer desvenlafaxin-freien base und von salzen oder solvaten daraus |
| EP2049465A2 (de) * | 2007-03-14 | 2009-04-22 | Teva Pharmaceutical Industries Ltd. | Verfahren zur herstellung von o-desmethylvenlafaxin in festem zustand |
| EP2200968A1 (de) * | 2007-10-26 | 2010-06-30 | Generics Ýuk¨Limited | Verfahren zur herstellung von o-desmethylvenlafaxin |
| WO2009070311A2 (en) | 2007-11-26 | 2009-06-04 | Teva Pharmaceutical Industries Ltd. | Crystal forms of o-desmethylvenlafaxine fumarate |
| WO2009084038A2 (en) * | 2007-12-28 | 2009-07-09 | Ind-Swift Laboratories Limited | Improved process for the preparation of 0-desmethyl-venlafaxine |
| CA2717580A1 (en) * | 2008-03-06 | 2009-12-17 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of o-desmethylvenlafaxine, free from its dimer impurities |
| CZ301503B6 (cs) | 2008-11-27 | 2010-03-24 | Zentiva, A. S. | Zpusob prípravy desvenlafaxinu a jeho solí |
| ES2343050B1 (es) * | 2008-12-16 | 2011-06-14 | Chemo Iberica, S.A. | Procedimiento para la preparacion de desvenlafaxina y sus sales de adicion de acido farmaceuticamente aceptables. |
| CZ200969A3 (cs) | 2009-02-06 | 2010-06-30 | Zentiva, K.S. | Nové soli desvenlafaxinu a zpusob jejich prípravy |
| CZ2009454A3 (cs) | 2009-07-15 | 2010-11-10 | Zentiva, K. S. | Zpusob prípravy desvenlafaxinu a jeho solí |
| EP2539313A2 (de) | 2010-03-29 | 2013-01-02 | Pliva Hrvatska D.O.O. | Kristalline formen von o-desmethylvenlafaxinfumarat |
| CZ303249B6 (cs) | 2010-04-06 | 2012-06-20 | Zentiva, K.S. | Zpusob výroby 4-(2-(substituovaných)-1-(1-hydroxycyklohexyl)ethyl)fenolu O-demethylací jejich methyletheru pomocí nepáchnoucích aromatických thiolu |
| WO2018146529A1 (en) | 2017-02-09 | 2018-08-16 | R L Finechem Private Limited | A process for preparation of1-[2-(dimethylamino)-1-(4-hydroxyphenyl) ethyl]-cyclohexanol and salts thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6197828B1 (en) * | 1998-12-01 | 2001-03-06 | Sepracor, Inc. | Derivatives of (+)-venlafaxine and methods of preparing and using the same |
| EP1905757A1 (de) | 1999-04-06 | 2008-04-02 | Sepracor Inc. | Derivate von Venlafaxin und Verfahren zu ihrer Herstellung und Verwendung |
| US6673838B2 (en) | 2001-02-12 | 2004-01-06 | Wyeth | Succinate salt of O-desmethyl-venlafaxine |
| UA80543C2 (en) * | 2001-12-04 | 2007-10-10 | Wyeth Corp | Method for the preparation of o-desmethylvenlafaxine |
| WO2007071404A1 (en) * | 2005-12-20 | 2007-06-28 | Synthon B.V. | Process for making desvenlafaxine |
-
2007
- 2007-04-17 JP JP2008517241A patent/JP2008546718A/ja active Pending
- 2007-04-17 WO PCT/US2007/009558 patent/WO2007120923A1/en active Application Filing
- 2007-04-17 EP EP07755727A patent/EP2007708A1/de not_active Withdrawn
- 2007-04-17 MX MX2007016172A patent/MX2007016172A/es unknown
- 2007-04-17 CA CA002646368A patent/CA2646368A1/en not_active Abandoned
-
2008
- 2008-08-12 IL IL193398A patent/IL193398A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008546718A (ja) | 2008-12-25 |
| WO2007120923A1 (en) | 2007-10-25 |
| MX2007016172A (es) | 2008-03-10 |
| EP2007708A1 (de) | 2008-12-31 |
| IL193398A0 (en) | 2009-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |