ME00154B - Sel de succinate et de malonate de trans-4-((1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine et son utilisation en tant que medicament - Google Patents

Sel de succinate et de malonate de trans-4-((1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine et son utilisation en tant que medicament

Info

Publication number: ME00154B
Authority: ME; Montenegro
Prior art keywords: compound; salt; formula; process according; phenylindan
Prior art date: 2003-08-18

Application number

MEP-2008-26A

Other languages

English (en)

Unknown language (me)

Inventor

De Diego Heidi Lopez

Ole Nielsen

Lone Munch Ringgard

Henrik Svane

Allan Carsten Dahl

Mark Howells

Andersen Benny Bang

Lars Ole Lyngsø

Original Assignee

H Lundbeck As

Priority date (The priority date 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 date listed.)

2003-08-18

Filing date

2004-08-18

Publication date

2010-10-10

2004-08-18 Application filed by H Lundbeck As filed Critical H Lundbeck As

2004-08-18 Priority claimed from PCT/DK2004/000545 external-priority patent/WO2005016900A1/fr

2010-06-10 Publication of MEP2608A publication Critical patent/MEP2608A/xx

2010-10-10 Publication of ME00154B publication Critical patent/ME00154B/fr

Links

239000003814 drug Substances 0.000 title claims abstract description 11
150000002690 malonic acid derivatives Chemical class 0.000 title claims description 20
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 title claims description 9
150000003839 salts Chemical class 0.000 claims abstract description 88
238000000034 method Methods 0.000 claims abstract description 59
201000000980 schizophrenia Diseases 0.000 claims abstract description 23
238000002360 preparation method Methods 0.000 claims abstract description 16
208000028017 Psychotic disease Diseases 0.000 claims abstract description 15
OFOBLEOULBTSOW-UHFFFAOYSA-M malonate(1-) Chemical compound OC(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-M 0.000 claims abstract description 12
BYPMJBXPNZMNQD-PZJWPPBQSA-N Zicronapine Chemical compound C1C(C)(C)N(C)CCN1[C@H]1C2=CC(Cl)=CC=C2[C@H](C=2C=CC=CC=2)C1 BYPMJBXPNZMNQD-PZJWPPBQSA-N 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 244
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 55
230000008569 process Effects 0.000 claims description 37
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical group OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
239000002904 solvent Substances 0.000 claims description 29
230000002255 enzymatic effect Effects 0.000 claims description 26
KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 claims description 26
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 22
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 21
-1 n. pn Inorganic materials 0.000 claims description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
239000012458 free base Substances 0.000 claims description 17
150000003890 succinate salts Chemical class 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
239000000843 powder Substances 0.000 claims description 12
208000024891 symptom Diseases 0.000 claims description 12
238000000634 powder X-ray diffraction Methods 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 10
230000005855 radiation Effects 0.000 claims description 10
RFAPOGMFZTYBEW-UHFFFAOYSA-N 1,2,2-trimethylpiperazine Chemical compound CN1CCNCC1(C)C RFAPOGMFZTYBEW-UHFFFAOYSA-N 0.000 claims description 9
238000000926 separation method Methods 0.000 claims description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
PIPWSBOFSUJCCO-UHFFFAOYSA-N 2,2-dimethylpiperazine Chemical compound CC1(C)CNCCN1 PIPWSBOFSUJCCO-UHFFFAOYSA-N 0.000 claims description 7
208000020925 Bipolar disease Diseases 0.000 claims description 5
206010026749 Mania Diseases 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
208000007848 Alcoholism Diseases 0.000 claims description 4
208000021465 Brief psychotic disease Diseases 0.000 claims description 4
208000027089 Parkinsonian disease Diseases 0.000 claims description 4
206010034010 Parkinsonism Diseases 0.000 claims description 4
206010001584 alcohol abuse Diseases 0.000 claims description 4
208000025746 alcohol use disease Diseases 0.000 claims description 4
238000002955 isolation Methods 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
208000022610 schizoaffective disease Diseases 0.000 claims description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
208000022497 Cocaine-Related disease Diseases 0.000 claims description 3
206010054089 Depressive symptom Diseases 0.000 claims description 3
206010013654 Drug abuse Diseases 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
208000019022 Mood disease Diseases 0.000 claims description 3
208000019568 Shared Paranoid disease Diseases 0.000 claims description 3
208000028810 Shared psychotic disease Diseases 0.000 claims description 3
206010043903 Tobacco abuse Diseases 0.000 claims description 3
150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
201000001272 cocaine abuse Diseases 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims description 3
239000000945 filler Substances 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
230000011987 methylation Effects 0.000 claims description 3
238000007069 methylation reaction Methods 0.000 claims description 3
239000003176 neuroleptic agent Substances 0.000 claims description 3
230000000701 neuroleptic effect Effects 0.000 claims description 3
150000003335 secondary amines Chemical class 0.000 claims description 3
201000009032 substance abuse Diseases 0.000 claims description 3
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 2
208000024254 Delusional disease Diseases 0.000 claims description 2
229930040373 Paraformaldehyde Natural products 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
229920002866 paraformaldehyde Polymers 0.000 claims description 2
208000002851 paranoid schizophrenia Diseases 0.000 claims description 2
238000006268 reductive amination reaction Methods 0.000 claims description 2
208000019116 sleep disease Diseases 0.000 claims description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 1
MMYNXKNHLGJGFF-LZAGWAHOSA-N butanedioic acid;4-[(1r,3s)-6-chloro-3-phenyl-2,3-dihydro-1h-inden-1-yl]-1,2,2-trimethylpiperazine Chemical compound OC(=O)CCC(O)=O.C1C(C)(C)N(C)CCN1[C@H]1C2=CC(Cl)=CC=C2[C@H](C=2C=CC=CC=2)C1 MMYNXKNHLGJGFF-LZAGWAHOSA-N 0.000 abstract 2
239000000203 mixture Substances 0.000 description 61
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
230000015572 biosynthetic process Effects 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000005917 acylation reaction Methods 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 18
230000010933 acylation Effects 0.000 description 17
230000020176 deacylation Effects 0.000 description 15
238000005947 deacylation reaction Methods 0.000 description 15
239000002244 precipitate Substances 0.000 description 15
239000008346 aqueous phase Substances 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
239000000725 suspension Substances 0.000 description 12
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 10
229910052717 sulfur Inorganic materials 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000012071 phase Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 8
238000000113 differential scanning calorimetry Methods 0.000 description 8
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
238000001914 filtration Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000001384 succinic acid Substances 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229960004592 isopropanol Drugs 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
238000001556 precipitation Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
229910052802 copper Inorganic materials 0.000 description 6
239000010949 copper Substances 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
229940093499 ethyl acetate Drugs 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000012467 final product Substances 0.000 description 6
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
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230000003287 optical effect Effects 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000012453 solvate Substances 0.000 description 5
ZBFIRYWCOIYJDA-UHFFFAOYSA-N 3,3-dimethylpiperazin-2-one Chemical compound CC1(C)NCCNC1=O ZBFIRYWCOIYJDA-UHFFFAOYSA-N 0.000 description 4
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 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
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239000012971 dimethylpiperazine Substances 0.000 description 4
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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 3
UUYMYRKAVSCKOJ-UHFFFAOYSA-N 3,3,4-trimethylpiperazin-2-one Chemical compound CN1CCNC(=O)C1(C)C UUYMYRKAVSCKOJ-UHFFFAOYSA-N 0.000 description 3
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

MEP-2008-26A 2003-08-18 2004-08-18 Sel de succinate et de malonate de trans-4-((1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine et son utilisation en tant que medicament ME00154B (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US49605803P	2003-08-18	2003-08-18
DKPA200301180		2003-08-18
US52024603P	2003-11-14	2003-11-14
PCT/DK2004/000545 WO2005016900A1 (fr)	2003-08-18	2004-08-18	Sel de succinate et de malonate de trans-4-((1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine et son utilisation en tant que medicament

Publications (2)

Publication Number	Publication Date
MEP2608A MEP2608A (en)	2010-06-10
ME00154B true ME00154B (fr)	2010-10-10

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MEP-2008-26A ME00154B (fr)	2003-08-18	2004-08-18	Sel de succinate et de malonate de trans-4-((1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine et son utilisation en tant que medicament

Country Status (4)

Country	Link
CN (2)	CN1835938A (fr)
ME (1)	ME00154B (fr)
UA (2)	UA89617C2 (fr)
ZA (2)	ZA200601421B (fr)

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EP2417101B1 (fr) *	2009-04-09	2013-10-23	Merck Sharp & Dohme B.V.	Dérivés d'indane
WO2012063843A1 (fr) *	2010-11-09	2012-05-18	株式会社カネカ	Indénones halogénées et procédé pour la production d'indanones optiquement actifs ou d'indanoles optiquement actifs utilisant lesdites indénones
US20130331575A1 (en) *	2011-01-07	2013-12-12	Robert Dancer	Method for resolution of 4-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-1,2,2-trimethyl-piperazine and 1-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-3,3-dimethyl-piperazine
CN112359078A (zh) *	2021-01-12	2021-02-12	凯莱英生命科学技术(天津)有限公司	异丁酸酯类化合物的手性拆分方法

2004
- 2004-08-18 ZA ZA200601421A patent/ZA200601421B/en unknown
- 2004-08-18 UA UAA200602709A patent/UA89617C2/ru unknown
- 2004-08-18 UA UAA200909651A patent/UA108342C2/ru unknown
- 2004-08-18 ME MEP-2008-26A patent/ME00154B/fr unknown
- 2004-08-18 ZA ZA200601173A patent/ZA200601173B/en unknown
- 2004-08-18 CN CNA2004800236381A patent/CN1835938A/zh active Pending
- 2004-08-18 CN CN2004800237257A patent/CN1839124B/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1835938A (zh)	2006-09-20
ZA200601421B (en)	2007-05-30
ZA200601173B (en)	2007-04-25
MEP2608A (en)	2010-06-10
CN1839124A (zh)	2006-09-27
CN1839124B (zh)	2010-06-16
UA89617C2 (en)	2010-02-25
UA108342C2 (uk)	2015-04-27

Publication	Publication Date	Title
CA2536144C (fr)	2010-09-14	Sel de succinate et de malonate de trans-4-((1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine et son utilisation en tant que medicament
BRPI0607438A2 (pt)	2010-04-06	métodos para fabricar um composto e para a conversão de composto ivb enantiomericamente enriquecido em composto iv essencialmente racêmico, e, composto
MX2007009816A (es)	2007-09-07	Sales de tartrato y de malato de trans-1-((1r,3s)-6-cloro-3- fenilindan-1-i1)-3,3-dimetilpiperazina.
EP1853576B1 (fr)	2011-07-06	Base cristalline de la trans-1-[(1r,3s)-6-chloro-3-phenylindan-1-yl]-3,3-dimethylpiperazine
ME00154B (fr)	2010-10-10	Sel de succinate et de malonate de trans-4-((1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine et son utilisation en tant que medicament
RS20060121A (sr)	2008-09-29	Sukcinat i malonat soli trans-4-((1r,3s)-6-hloro-3- fenilindan-1-il)-1,2,2-trimetilpiperazin i njihova upotreba kao medikamenata
HK1096089B (en)	2011-02-02	Succinate and malonate salt of trans-4-(ir,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and the use as a medicament
HK1152699B (en)	2013-08-30	Method for preparing trans-4-((1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and the salts thereof and the intermediates used therein