NL1016012C1 - Tosylaatzouten van 4-(p-fluorfenyl)-piperidine-3-carbinols. - Google Patents

Tosylaatzouten van 4-(p-fluorfenyl)-piperidine-3-carbinols. Download PDF

Info

Publication number: NL1016012C1
Authority: NL; Netherlands
Prior art keywords: compound; formula; group; methyl; impurity
Prior art date: 2000-05-12

Application number

NL1016012A

Other languages

English (en)

Dutch (nl)

Inventor

Jacobus Maria Lemmens

Theodorus Hendricus Ant Peters

Pavel Slanina

Original Assignee

Synthon Bv

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.)

2000-05-12

Filing date

2000-08-24

Publication date

2001-01-30

2000-08-24 Application filed by Synthon Bv filed Critical Synthon Bv

2001-01-30 Application granted granted Critical

2001-01-30 Publication of NL1016012C1 publication Critical patent/NL1016012C1/nl

Links

125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 title claims description 15
125000005490 tosylate group Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 70
239000012535 impurity Substances 0.000 claims description 53
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 45
238000000034 method Methods 0.000 claims description 39
AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 30
238000002360 preparation method Methods 0.000 claims description 29
AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 27
229960002296 paroxetine Drugs 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 14
230000003287 optical effect Effects 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000007787 solid Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 4
239000012453 solvate Substances 0.000 claims description 4
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
239000011265 semifinished product Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000003814 drug Substances 0.000 claims 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
150000003839 salts Chemical class 0.000 description 34
229910052731 fluorine Inorganic materials 0.000 description 23
239000011737 fluorine Substances 0.000 description 23
238000000746 purification Methods 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
239000007858 starting material Substances 0.000 description 11
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
-1 lithium aluminum hydride Chemical compound 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
238000001556 precipitation Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
150000004678 hydrides Chemical class 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
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
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000007423 decrease Effects 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229910052987 metal hydride Inorganic materials 0.000 description 3
150000004681 metal hydrides Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
150000008054 sulfonate salts Chemical class 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
VUYNWBMXOQBJAI-RDJZCZTQSA-N (3s,4r)-3-(1,3-benzodioxol-5-yloxymethyl)-4-phenylpiperidine Chemical compound C1([C@@H]2CCNC[C@H]2COC=2C=C3OCOC3=CC=2)=CC=CC=C1 VUYNWBMXOQBJAI-RDJZCZTQSA-N 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
MOJZPKOBKCXNKG-YJBOKZPZSA-N N-methylparoxetine Chemical compound C1([C@@H]2CCN(C[C@H]2COC=2C=C3OCOC3=CC=2)C)=CC=C(F)C=C1 MOJZPKOBKCXNKG-YJBOKZPZSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
238000002955 isolation Methods 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229960005183 paroxetine hydrochloride Drugs 0.000 description 2
238000000926 separation method Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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 description 1
BNNMDMGPZUOOOE-UHFFFAOYSA-N 4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1 BNNMDMGPZUOOOE-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
CXRHUYYZISIIMT-AAEUAGOBSA-N [(3s,4r)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl]methanol Chemical compound OC[C@@H]1CN(C)CC[C@H]1C1=CC=C(F)C=C1 CXRHUYYZISIIMT-AAEUAGOBSA-N 0.000 description 1
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006115 defluorination reaction Methods 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
FKIUWSNIJDINFT-UHFFFAOYSA-N methanol;1,2,3,4-tetrahydropyridine Chemical class OC.C1CNC=CC1 FKIUWSNIJDINFT-UHFFFAOYSA-N 0.000 description 1
CEXCHYIGFUAPKW-UHFFFAOYSA-N methanol;piperidine Chemical class OC.C1CCNCC1 CEXCHYIGFUAPKW-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000013021 overheating Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
238000004448 titration Methods 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
125000004950 trifluoroalkyl group Chemical group 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NL1016012A 2000-05-12 2000-08-24 Tosylaatzouten van 4-(p-fluorfenyl)-piperidine-3-carbinols. NL1016012C1 (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL0000320		2000-05-12
PCT/NL2000/000320 WO2001085688A1 (fr)	2000-05-12	2000-05-12	Tosylates de 4-(p-fluorophenyl)-piperidine-3-carbinols

Publications (1)

Publication Number	Publication Date
NL1016012C1 true NL1016012C1 (nl)	2001-01-30

Family

ID=19760688

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1016012A NL1016012C1 (nl)	2000-05-12	2000-08-24	Tosylaatzouten van 4-(p-fluorfenyl)-piperidine-3-carbinols.

Country Status (6)

Country	Link
US (1)	US6521758B2 (fr)
EP (1)	EP1280775A1 (fr)
AU (1)	AU2000246280A1 (fr)
CZ (1)	CZ20023694A3 (fr)
NL (1)	NL1016012C1 (fr)
WO (1)	WO2001085688A1 (fr)

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GB9930577D0 (en) *	1999-12-23	2000-02-16	Smithkline Beecham Plc	Novel process
CN101205211B (zh) *	2006-12-19	2011-12-14	北京德众万全药物技术开发有限公司	一种盐酸帕罗西汀重要中间体的制备方法
WO2009143347A2 (fr) *	2008-05-22	2009-11-26	Teva Pharmaceutical Industries Ltd.	Tosylate de varénicline, un intermédiaire dans le procédé de préparation du l-tartrate de varénicline
US8178537B2 (en)	2009-06-22	2012-05-15	Teva Pharmaceutical Industries Ltd.	Solid state forms of varenicline salts and processes for preparation thereof
CN104402800A (zh) *	2014-12-02	2015-03-11	千辉药业（安徽）有限责任公司	一种反式-4-(4-氟苯基)-3-羟甲基-1-甲基哌啶的制备方法

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GB1422263A (en) *	1973-01-30	1976-01-21	Ferrosan As	4-phenyl-piperidine compounds
US4585777A (en)	1984-02-07	1986-04-29	A/S Ferrosan	(-)-Trans-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)methylpiperidine for potentiating 5-HT
EP0190496A3 (fr) *	1984-12-13	1987-05-27	Beecham Group Plc	Dérivés de la pipéridine à activité gastro-intestinale
DE3680184D1 (de) *	1985-08-10	1991-08-14	Beecham Group Plc	Verfahren zur herstellung von arylpiperidincarbinol.
GB8714707D0 (en)	1987-06-23	1987-07-29	Beecham Group Plc	Chemical process
GB9209687D0 (en)	1992-05-06	1992-06-17	Smithkline Beecham Plc	Novel process
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NZ307479A (en)	1995-05-17	1999-08-30	Novo Nordisk As	A process for preparing 4-(4-halo substituted phenyl)-3-(3,4-methylenedioxy phenoxy methyl)piperidine derivatives
JP3446468B2 (ja)	1996-04-15	2003-09-16	旭硝子株式会社	ピペリジンカルビノール類の製造方法
JP3882224B2 (ja)	1996-05-31	2007-02-14	旭硝子株式会社	パロキセチンの製造方法
EP1384720A1 (fr)	1996-06-13	2004-01-28	SUMIKA FINE CHEMICALS Co., Ltd.	Procédé de séchage pour le chlorhydrate de paroxetine
HU221921B1 (hu)	1996-07-08	2003-02-28	Richter Gedeon Vegyészeti Gyár Rt.	N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására
GB9710004D0 (en) *	1997-05-17	1997-07-09	Knoll Ag	Chemical process
ES2155995T3 (es) *	1997-06-10	2001-06-01	Synthon Bv	Compuestos de 4-fenilpiperidina.
AU6360999A (en) *	1998-11-02	2000-05-22	Synthon B.V.	Process for producing 4-arylpiperidine-3-carbinols and related compounds
SI1286965T1 (en) *	2000-05-12	2004-04-30	Synthon B.V.	Piperidine compounds and process for providing such

2000
- 2000-05-12 AU AU2000246280A patent/AU2000246280A1/en not_active Abandoned
- 2000-05-12 WO PCT/NL2000/000320 patent/WO2001085688A1/fr not_active Ceased
- 2000-05-12 EP EP00927978A patent/EP1280775A1/fr not_active Withdrawn
- 2000-05-12 CZ CZ20023694A patent/CZ20023694A3/cs unknown
- 2000-08-24 NL NL1016012A patent/NL1016012C1/nl not_active IP Right Cessation
2001
- 2001-05-14 US US09/853,898 patent/US6521758B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CZ20023694A3 (cs)	2003-05-14
AU2000246280A1 (en)	2001-11-20
WO2001085688A1 (fr)	2001-11-15
US20020082277A1 (en)	2002-06-27
EP1280775A1 (fr)	2003-02-05
US6521758B2 (en)	2003-02-18

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