ES2385975T3 - Procedimiento para la preparación de citalopram diol racémico y/o S- O R-citalopram dioles y el uso de tales dioles para la preparación de citalopram racémico, R-citalopram y/o S-citalopram - Google Patents
Procedimiento para la preparación de citalopram diol racémico y/o S- O R-citalopram dioles y el uso de tales dioles para la preparación de citalopram racémico, R-citalopram y/o S-citalopram Download PDFInfo
- Publication number
- ES2385975T3 ES2385975T3 ES03767476T ES03767476T ES2385975T3 ES 2385975 T3 ES2385975 T3 ES 2385975T3 ES 03767476 T ES03767476 T ES 03767476T ES 03767476 T ES03767476 T ES 03767476T ES 2385975 T3 ES2385975 T3 ES 2385975T3
- Authority
- ES
- Spain
- Prior art keywords
- diol
- free base
- acid addition
- addition salt
- acid
- 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.)
- Expired - Lifetime
Links
- 150000002009 diols Chemical class 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 63
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 229960001653 citalopram Drugs 0.000 title claims description 57
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 title claims description 39
- -1 citalopram diol Chemical class 0.000 title claims description 16
- 239000002253 acid Substances 0.000 claims abstract description 254
- 150000003839 salts Chemical class 0.000 claims abstract description 239
- 239000012458 free base Substances 0.000 claims abstract description 201
- 239000000203 mixture Substances 0.000 claims abstract description 144
- 239000002244 precipitate Substances 0.000 claims abstract description 71
- 239000002904 solvent Substances 0.000 claims abstract description 67
- 238000000746 purification Methods 0.000 claims abstract description 21
- 239000002585 base Substances 0.000 claims abstract description 16
- 238000000926 separation method Methods 0.000 claims abstract description 15
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 11
- GNULRNVWXYXBQY-UHFFFAOYSA-N 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile Chemical compound C=1C=C(C#N)C=C(CO)C=1C(O)(CCCN(C)C)C1=CC=C(F)C=C1 GNULRNVWXYXBQY-UHFFFAOYSA-N 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
- 239000000243 solution Substances 0.000 claims description 52
- 238000001556 precipitation Methods 0.000 claims description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000004090 dissolution Methods 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000001704 evaporation Methods 0.000 claims description 11
- 230000008020 evaporation Effects 0.000 claims description 11
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000010413 mother solution Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 235000006408 oxalic acid Nutrition 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 150000003891 oxalate salts Chemical class 0.000 claims description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000005191 phase separation Methods 0.000 claims description 2
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000007787 solid Substances 0.000 description 27
- 239000012071 phase Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000011550 stock solution Substances 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 10
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 9
- 238000009826 distribution Methods 0.000 description 8
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 description 8
- 229960004341 escitalopram Drugs 0.000 description 8
- 238000007429 general method Methods 0.000 description 8
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012485 toluene extract Substances 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GNULRNVWXYXBQY-HXUWFJFHSA-N 4-[(1r)-4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile Chemical compound C1([C@](O)(CCCN(C)C)C=2C(=CC(=CC=2)C#N)CO)=CC=C(F)C=C1 GNULRNVWXYXBQY-HXUWFJFHSA-N 0.000 description 1
- RVGFHORHCHHPCZ-UHFFFAOYSA-N 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile;hydrobromide Chemical compound Br.C=1C=C(C#N)C=C(CO)C=1C(O)(CCCN(C)C)C1=CC=C(F)C=C1 RVGFHORHCHHPCZ-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000004170 methylsulfonyl group Chemical class [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43611702P | 2002-12-23 | 2002-12-23 | |
| US436117P | 2002-12-23 | ||
| DK200202004 | 2002-12-23 | ||
| DKPA200202004 | 2002-12-23 | ||
| PCT/DK2003/000907 WO2004056754A1 (en) | 2002-12-23 | 2003-12-18 | A process for the preparation of racemic citalopram diol and/or s- or r- citalopram diols and the use of such diols for the preparation of racemic citalopram, r-citalopram and/or s-citalopram |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2385975T3 true ES2385975T3 (es) | 2012-08-06 |
Family
ID=35423357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03767476T Expired - Lifetime ES2385975T3 (es) | 2002-12-23 | 2003-12-18 | Procedimiento para la preparación de citalopram diol racémico y/o S- O R-citalopram dioles y el uso de tales dioles para la preparación de citalopram racémico, R-citalopram y/o S-citalopram |
Country Status (17)
| Country | Link |
|---|---|
| KR (1) | KR101076640B1 (ru) |
| CN (1) | CN100334071C (ru) |
| AR (1) | AR042655A1 (ru) |
| BR (1) | BR0317629A (ru) |
| DK (1) | DK1581483T3 (ru) |
| EA (1) | EA009061B1 (ru) |
| ES (1) | ES2385975T3 (ru) |
| ME (1) | MEP5708A (ru) |
| MY (1) | MY142404A (ru) |
| PE (1) | PE20050065A1 (ru) |
| PT (1) | PT1581483E (ru) |
| RS (1) | RS52152B (ru) |
| SI (1) | SI1581483T1 (ru) |
| TW (1) | TWI331605B (ru) |
| UA (1) | UA84859C2 (ru) |
| UY (1) | UY28146A1 (ru) |
| ZA (1) | ZA200504715B (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA95199U (uk) | 2014-07-09 | 2014-12-10 | Дозатор з точним дозуванням для сипучих продуктів | |
| CN110590602B (zh) * | 2019-09-25 | 2022-04-05 | 浙江海森药业股份有限公司 | 外消旋西酞普兰二醇的拆分精制方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8814057D0 (en) * | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
| AR034612A1 (es) * | 2001-06-25 | 2004-03-03 | Lundbeck & Co As H | Proceso para la preparacion del citalopram racemico y/o del s- o r-citalopram mediante la separacion de una mezcla de r- y s-citalopram |
-
2003
- 2003-12-18 CN CNB200380107283XA patent/CN100334071C/zh not_active Expired - Lifetime
- 2003-12-18 PT PT03767476T patent/PT1581483E/pt unknown
- 2003-12-18 KR KR1020057011898A patent/KR101076640B1/ko not_active IP Right Cessation
- 2003-12-18 RS YU20050488A patent/RS52152B/sr unknown
- 2003-12-18 ES ES03767476T patent/ES2385975T3/es not_active Expired - Lifetime
- 2003-12-18 UA UAA200506921A patent/UA84859C2/ru unknown
- 2003-12-18 ME MEP-57/08A patent/MEP5708A/xx unknown
- 2003-12-18 BR BR0317629-0A patent/BR0317629A/pt not_active Application Discontinuation
- 2003-12-18 DK DK03767476.9T patent/DK1581483T3/da active
- 2003-12-18 SI SI200332174T patent/SI1581483T1/sl unknown
- 2003-12-18 EA EA200501042A patent/EA009061B1/ru not_active IP Right Cessation
- 2003-12-18 TW TW092135925A patent/TWI331605B/zh not_active IP Right Cessation
- 2003-12-22 AR ARP030104781A patent/AR042655A1/es unknown
- 2003-12-22 MY MYPI20034948A patent/MY142404A/en unknown
- 2003-12-22 UY UY28146A patent/UY28146A1/es not_active Application Discontinuation
-
2004
- 2004-01-05 PE PE2004000033A patent/PE20050065A1/es not_active Application Discontinuation
-
2005
- 2005-06-09 ZA ZA200504715A patent/ZA200504715B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ME00034B (me) | 2010-02-10 |
| UY28146A1 (es) | 2004-07-30 |
| MY142404A (en) | 2010-11-30 |
| RS52152B (sr) | 2012-08-31 |
| DK1581483T3 (da) | 2012-07-23 |
| CN1729164A (zh) | 2006-02-01 |
| EA200501042A1 (ru) | 2005-12-29 |
| PE20050065A1 (es) | 2005-02-18 |
| KR20050093801A (ko) | 2005-09-23 |
| MEP5708A (xx) | 2010-02-10 |
| PT1581483E (pt) | 2012-07-24 |
| KR101076640B1 (ko) | 2011-10-27 |
| BR0317629A (pt) | 2005-11-29 |
| RS20050488A (en) | 2007-06-04 |
| SI1581483T1 (sl) | 2012-09-28 |
| AR042655A1 (es) | 2005-06-29 |
| EA009061B1 (ru) | 2007-10-26 |
| CN100334071C (zh) | 2007-08-29 |
| TWI331605B (en) | 2010-10-11 |
| TW200512202A (en) | 2005-04-01 |
| UA84859C2 (ru) | 2008-12-10 |
| ZA200504715B (en) | 2006-08-30 |
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