OA11223A - Novel process - Google Patents

Novel process Download PDF

Info

Publication number: OA11223A
Authority: OA; OAPI
Prior art keywords: hydrogen; compound; aryl; alkyl; fluorophenyl
Prior art date: 1997-05-29

Application number

OA9900263A

Other languages

English (en)

Inventor

Marvin Yu Sungwhan

Victor Witold Jacewicz

Evgeny Shapiro

Original Assignee

Smithkline Beecham Corp

Smithkline Beecham Plc

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.)

1997-05-29

Filing date

1999-11-29

Publication date

2003-06-17

1997-05-29 Priority claimed from GBGB9711095.1A external-priority patent/GB9711095D0/en

1997-07-15 Priority claimed from GBGB9714875.3A external-priority patent/GB9714875D0/en

1999-11-29 Application filed by Smithkline Beecham Corp, Smithkline Beecham Plc filed Critical Smithkline Beecham Corp

2003-06-17 Publication of OA11223A publication Critical patent/OA11223A/en

Links

238000000034 method Methods 0.000 title claims description 36
150000001875 compounds Chemical class 0.000 claims abstract description 66
-1 3,4-methylenedioxyphenyl group Chemical group 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
239000005864 Sulphur Chemical group 0.000 claims description 6
LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 5
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
125000004185 ester group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
150000003840 hydrochlorides Chemical class 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
230000000069 prophylactic effect Effects 0.000 claims 1
AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 abstract description 31
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 abstract description 15
229960002296 paroxetine Drugs 0.000 abstract description 15
239000000543 intermediate Substances 0.000 abstract description 14
239000000243 solution Substances 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
230000002829 reductive effect Effects 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
229940083608 sodium hydroxide Drugs 0.000 description 9
ZCLNVLFDOBHPDS-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)-6-oxopiperidin-3-yl]propanoic acid Chemical compound OC(=O)CCC1CNC(=O)CC1C1=CC=C(F)C=C1 ZCLNVLFDOBHPDS-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
229960005183 paroxetine hydrochloride Drugs 0.000 description 8
239000000284 extract Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
MHGHQXGVKZMRJH-UHFFFAOYSA-N diethyl 2-cyano-3-(4-fluorophenyl)pentanedioate Chemical compound CCOC(=O)CC(C(C#N)C(=O)OCC)C1=CC=C(F)C=C1 MHGHQXGVKZMRJH-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
ZZAHLTSAUSODSU-QGZVFWFLSA-N (3r)-1-benzyl-3-(4-fluorophenyl)piperidin-2-one Chemical compound C1=CC(F)=CC=C1[C@@H]1C(=O)N(CC=2C=CC=CC=2)CCC1 ZZAHLTSAUSODSU-QGZVFWFLSA-N 0.000 description 3
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 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
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 3
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 3
AELJBFRPEBTCSA-HKUYNNGSSA-N [(3s,4r)-1-benzyl-4-(4-fluorophenyl)piperidin-3-yl]methanol Chemical compound C([C@H]([C@@H](CC1)C=2C=CC(F)=CC=2)CO)N1CC1=CC=CC=C1 AELJBFRPEBTCSA-HKUYNNGSSA-N 0.000 description 3
239000012267 brine Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229960004132 diethyl ether Drugs 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
IBMRTYCHDPMBFN-UHFFFAOYSA-N monomethyl glutaric acid Chemical compound COC(=O)CCCC(O)=O IBMRTYCHDPMBFN-UHFFFAOYSA-N 0.000 description 3
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
VZSAZXSNAZICDQ-ROUUACIJSA-N 2-[(3s,4r)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidin-3-yl]acetic acid Chemical compound C([C@H]([C@@H](C1=O)CC(=O)O)C=2C=CC(F)=CC=2)CN1CC1=CC=CC=C1 VZSAZXSNAZICDQ-ROUUACIJSA-N 0.000 description 2
XCHBPAPQPRVEJT-UHFFFAOYSA-N 2-cyano-3-(4-fluorophenyl)pentanedioic acid Chemical class OC(=O)CC(C(C#N)C(O)=O)C1=CC=C(F)C=C1 XCHBPAPQPRVEJT-UHFFFAOYSA-N 0.000 description 2
KHIPXSSWTTYVBZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(hydroxymethyl)piperidin-2-one Chemical compound OCC1CNC(=O)CC1C1=CC=C(F)C=C1 KHIPXSSWTTYVBZ-UHFFFAOYSA-N 0.000 description 2
CJSSSTZFSUNNJL-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidin-2-one Chemical compound C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNC(=O)C1 CJSSSTZFSUNNJL-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
206010036618 Premenstrual syndrome Diseases 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
MXIFCNZZUPFATE-UHFFFAOYSA-N [4-(4-fluorophenyl)-1-methyl-3,6-dihydro-2h-pyridin-3-yl]methanol Chemical compound OCC1CN(C)CC=C1C1=CC=C(F)C=C1 MXIFCNZZUPFATE-UHFFFAOYSA-N 0.000 description 2
CXRHUYYZISIIMT-UHFFFAOYSA-N [4-(4-fluorophenyl)-1-methylpiperidin-3-yl]methanol Chemical group OCC1CN(C)CCC1C1=CC=C(F)C=C1 CXRHUYYZISIIMT-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
BJBLSDWTKDQYDO-UHFFFAOYSA-N dimethyl 3-(4-fluorophenyl)pentanedioate Chemical compound COC(=O)CC(CC(=O)OC)C1=CC=C(F)C=C1 BJBLSDWTKDQYDO-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
229940052303 ethers for general anesthesia Drugs 0.000 description 2
UNAXNPTZJKKUGO-VMPITWQZSA-N ethyl (e)-3-(4-fluorophenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=C(F)C=C1 UNAXNPTZJKKUGO-VMPITWQZSA-N 0.000 description 2
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000011282 treatment Methods 0.000 description 2
YCDQTTZPMJRWCQ-SECBINFHSA-N (3r)-3-(4-fluorophenyl)-5-methoxy-5-oxopentanoic acid Chemical compound COC(=O)C[C@@H](CC(O)=O)C1=CC=C(F)C=C1 YCDQTTZPMJRWCQ-SECBINFHSA-N 0.000 description 1
VAZUALNXCVLSGB-MRXNPFEDSA-N (4r)-1-benzyl-4-(4-fluorophenyl)piperidin-2-one Chemical compound C1=CC(F)=CC=C1[C@H]1CC(=O)N(CC=2C=CC=CC=2)CC1 VAZUALNXCVLSGB-MRXNPFEDSA-N 0.000 description 1
ZCLNVLFDOBHPDS-PWSUYJOCSA-N 3-[(3s,4r)-4-(4-fluorophenyl)-6-oxopiperidin-3-yl]propanoic acid Chemical compound OC(=O)CC[C@@H]1CNC(=O)C[C@H]1C1=CC=C(F)C=C1 ZCLNVLFDOBHPDS-PWSUYJOCSA-N 0.000 description 1
KFXTZZJAWWTKKH-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)-6-oxopiperidin-3-yl]propanoic acid 3-[4-(4-fluorophenyl)piperidin-3-yl]propanoic acid Chemical compound OC(=O)CCC1CNCCC1c1ccc(F)cc1.OC(=O)CCC1CNC(=O)CC1c1ccc(F)cc1 KFXTZZJAWWTKKH-UHFFFAOYSA-N 0.000 description 1
FYGWJEDFEJZMIC-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-methyl-3,6-dihydro-2h-pyridine Chemical compound C1N(C)CCC(C=2C=CC(F)=CC=2)=C1 FYGWJEDFEJZMIC-UHFFFAOYSA-N 0.000 description 1
GKRBZKLEBAMWJV-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-oxopiperidine-3-carbaldehyde Chemical group C1=CC(F)=CC=C1C1C(=O)CNCC1C=O GKRBZKLEBAMWJV-UHFFFAOYSA-N 0.000 description 1
QVBZFCLOWHRIAR-UHFFFAOYSA-N 4-(4-fluorophenyl)-6-oxopiperidine-3-carbaldehyde Chemical compound C1=CC(F)=CC=C1C1C(C=O)CNC(=O)C1 QVBZFCLOWHRIAR-UHFFFAOYSA-N 0.000 description 1
TWKUJYBXYMEBHP-UHFFFAOYSA-N 4-(4-fluorophenyl)-6-oxopiperidine-3-carboxylic acid Chemical compound OC(=O)C1CNC(=O)CC1C1=CC=C(F)C=C1 TWKUJYBXYMEBHP-UHFFFAOYSA-N 0.000 description 1
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
NBSVQJVZYVYKMG-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yloxy)-1,3-benzodioxole Chemical compound C1=C2OCOC2=CC(OC2=CC=C3OCOC3=C2)=C1 NBSVQJVZYVYKMG-UHFFFAOYSA-N 0.000 description 1
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 1
208000007848 Alcoholism Diseases 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
208000000094 Chronic Pain Diseases 0.000 description 1
SDXUVFASLYVNSG-UHFFFAOYSA-N FC1=CC=C(C=O)C=C1.FC1=CC=C(C=C1)C(CC(=O)OC)CC(=O)OC Chemical compound FC1=CC=C(C=O)C=C1.FC1=CC=C(C=C1)C(CC(=O)OC)CC(=O)OC SDXUVFASLYVNSG-UHFFFAOYSA-N 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
206010039966 Senile dementia Diseases 0.000 description 1
206010041250 Social phobia Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
IBOPBHBOBJYXTD-UHFFFAOYSA-N [4-(4-fluorophenyl)piperidin-3-yl]methanol Chemical compound OCC1CNCCC1C1=CC=C(F)C=C1 IBOPBHBOBJYXTD-UHFFFAOYSA-N 0.000 description 1
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
201000007930 alcohol dependence Diseases 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
230000000648 anti-parkinson Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000000939 antiparkinson agent Substances 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229960002376 chymotrypsin Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
208000024732 dysthymic disease Diseases 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
VVQFVFIVIHHUQV-UHFFFAOYSA-N ethyl 4-(3-methoxyphenyl)-2-oxopiperidine-3-carboxylate Chemical compound C1CNC(=O)C(C(=O)OCC)C1C1=CC=CC(OC)=C1 VVQFVFIVIHHUQV-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
FIMAYKDZLLQUDW-UHFFFAOYSA-N fluoro(dioxido)borane;trimethyloxidanium Chemical compound C[O+](C)C.C[O+](C)C.[O-]B([O-])F FIMAYKDZLLQUDW-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
239000000401 methanolic extract Substances 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
MNHJHRLVLCVXON-UHFFFAOYSA-N methyl 3-(4-fluorophenyl)-5-hydroxypentanoate Chemical compound COC(=O)CC(CCO)C1=CC=C(F)C=C1 MNHJHRLVLCVXON-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
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 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229960001407 sodium bicarbonate Drugs 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
201000009032 substance abuse Diseases 0.000 description 1
231100000736 substance abuse Toxicity 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004291 sulphur dioxide Substances 0.000 description 1
235000010269 sulphur dioxide Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
208000002271 trichotillomania Diseases 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/06—Antimigraine agents
- 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
- A61P25/22—Anxiolytics
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- 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
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Addiction (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Hospice & Palliative Care (AREA)
Dermatology (AREA)
Child & Adolescent Psychology (AREA)
Reproductive Health (AREA)
Hematology (AREA)
Obesity (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

OA9900263A 1997-05-29 1999-11-29 Novel process OA11223A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9711095.1A GB9711095D0 (en)	1997-05-29	1997-05-29	Novel process
GBGB9714875.3A GB9714875D0 (en)	1997-07-15	1997-07-15	Novel process

Publications (1)

Publication Number	Publication Date
OA11223A true OA11223A (en)	2003-06-17

Family

ID=26311618

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900263A OA11223A (en)	1997-05-29	1999-11-29	Novel process

Country Status (22)

Country	Link
US (3)	US6489347B1 (de)
EP (1)	EP0986389B1 (de)
JP (1)	JP2002514222A (de)
CN (1)	CN1268889A (de)
AP (1)	AP9901698A0 (de)
AT (1)	ATE279393T1 (de)
AU (1)	AU7708998A (de)
BG (1)	BG104034A (de)
BR (1)	BR9809687A (de)
CA (1)	CA2291251A1 (de)
DE (1)	DE69827000D1 (de)
EA (1)	EA199901098A1 (de)
HU (1)	HUP0003958A3 (de)
ID (1)	ID24383A (de)
IL (1)	IL133140A0 (de)
NO (1)	NO995796L (de)
NZ (1)	NZ501285A (de)
OA (1)	OA11223A (de)
PL (1)	PL337513A1 (de)
SK (1)	SK159899A3 (de)
TR (1)	TR199902929T2 (de)
WO (1)	WO1998053824A1 (de)

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US6438585B2 (en) *	1998-05-29	2002-08-20	Research In Motion Limited	System and method for redirecting message attachments between a host system and a mobile data communication device
AU6360999A (en) *	1998-11-02	2000-05-22	Synthon B.V.	Process for producing 4-arylpiperidine-3-carbinols and related compounds
US20010053862A1 (en) *	1998-12-22	2001-12-20	Bruce Ronsen	Process for preparing arylpiperidine carbinol intermediates and derivatives
GB9828767D0 (en) *	1998-12-29	1999-02-17	Smithkline Beecham Plc	Novel process
IT1313702B1 (it) *	1999-08-02	2002-09-09	Chemi Spa	Processo per la preparazione di derivati 3-sostituiti di 4-fenil-piperidine.
GB0003232D0 (en) *	2000-02-11	2000-04-05	Smithkline Beecham Plc	Novel composition
US6833458B2 (en) *	2000-06-05	2004-12-21	Development Center For Biotechnology	Practical syntheses of chiral trans-3, 4-disubstituted piperidines and the intermediates
EP1347960B1 (de) *	2001-01-04	2004-11-17	Ferrer Internacional, S.A.	Verfahren zur herstellung von (+)-trans-4-p-fluorophenyl-3-hydroxymethyl-1-methylpiperidin
NZ532432A (en)	2001-10-22	2005-02-25	Synthon Bv	N-formyl paroxetine compounds and their use in a synthetic route for obtaining paroxetine
US20080033050A1 (en)	2006-08-04	2008-02-07	Richards Patricia Allison Tewe	Method of treating thermoregulatory disfunction with paroxetine
US9138430B2 (en) *	2007-12-27	2015-09-22	Mylan Specialty L.P.	Formulation and method for the release of paroxetine in the large intestine
CN112645951A (zh) *	2020-12-23	2021-04-13	上海博栋化学科技有限公司	由长春布宁合成的磺酸锍盐类光产酸剂及其合成方法
CN119100972A (zh) *	2023-06-09	2024-12-10	浙江大学	一种帕罗西汀中间体的制备方法

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GB1422263A (en)	1973-01-30	1976-01-21	Ferrosan As	4-phenyl-piperidine compounds
US4593036A (en)	1984-02-07	1986-06-03	A/S Ferrosan	(-)-Trans-4-(4-fluorophenyl)-3-[(4-methoxyphenoxy)methyl]-1-methylpiperidine useful as 5-HT potentiator
US4585777A (en)	1984-02-07	1986-04-29	A/S Ferrosan	(-)-Trans-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)methylpiperidine for potentiating 5-HT
EP0190496A3 (de) *	1984-12-13	1987-05-27	Beecham Group Plc	Piperidinderivate mit gastro-intestinaler Wirkung
EP0223334B1 (de) *	1985-08-10	1991-07-10	Beecham Group Plc	Verfahren zur Herstellung von Arylpiperidincarbinol
GB8520154D0 (en)	1985-08-10	1985-09-18	Beecham Group Plc	Chemical process
GB8714707D0 (en)	1987-06-23	1987-07-29	Beecham Group Plc	Chemical process
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AU6360999A (en)	1998-11-02	2000-05-22	Synthon B.V.	Process for producing 4-arylpiperidine-3-carbinols and related compounds
US6051812A (en) *	1998-11-16	2000-04-18	Walker; Lawrence	Snow and ice melting blanket device

1998
- 1998-05-29 EP EP98925055A patent/EP0986389B1/de not_active Expired - Lifetime
- 1998-05-29 BR BR9809687-7A patent/BR9809687A/pt not_active Application Discontinuation
- 1998-05-29 ID IDW991488A patent/ID24383A/id unknown
- 1998-05-29 IL IL13314098A patent/IL133140A0/xx unknown
- 1998-05-29 WO PCT/US1998/011057 patent/WO1998053824A1/en not_active Ceased
- 1998-05-29 HU HU0003958A patent/HUP0003958A3/hu unknown
- 1998-05-29 TR TR1999/02929T patent/TR199902929T2/xx unknown
- 1998-05-29 AU AU77089/98A patent/AU7708998A/en not_active Abandoned
- 1998-05-29 DE DE1998627000 patent/DE69827000D1/de not_active Expired - Lifetime
- 1998-05-29 CN CN98805522A patent/CN1268889A/zh active Pending
- 1998-05-29 PL PL98337513A patent/PL337513A1/xx unknown
- 1998-05-29 EA EA199901098A patent/EA199901098A1/ru unknown
- 1998-05-29 AP APAP/P/1999/001698A patent/AP9901698A0/en unknown
- 1998-05-29 JP JP50100199A patent/JP2002514222A/ja not_active Ceased
- 1998-05-29 CA CA002291251A patent/CA2291251A1/en not_active Abandoned
- 1998-05-29 NZ NZ501285A patent/NZ501285A/en unknown
- 1998-05-29 AT AT98925055T patent/ATE279393T1/de not_active IP Right Cessation
- 1998-05-29 US US09/087,632 patent/US6489347B1/en not_active Expired - Fee Related
- 1998-05-29 SK SK1598-99A patent/SK159899A3/sk unknown
1999
- 1999-11-26 NO NO995796A patent/NO995796L/no not_active Application Discontinuation
- 1999-11-29 OA OA9900263A patent/OA11223A/en unknown
- 1999-12-17 BG BG104034A patent/BG104034A/xx unknown
2002
- 2002-05-03 US US10/138,553 patent/US6716985B2/en not_active Expired - Fee Related
2004
- 2004-01-14 US US10/757,147 patent/US20040147754A1/en not_active Abandoned

Also Published As

Publication number	Publication date
IL133140A0 (en)	2001-03-19
AP9901698A0 (en)	1999-12-31
PL337513A1 (en)	2000-08-28
NO995796D0 (no)	1999-11-26
US20020133011A1 (en)	2002-09-19
NZ501285A (en)	2001-10-26
WO1998053824A1 (en)	1998-12-03
EA199901098A1 (ru)	2000-08-28
ATE279393T1 (de)	2004-10-15
HUP0003958A2 (hu)	2001-05-28
TR199902929T2 (xx)	2000-06-21
EP0986389A1 (de)	2000-03-22
EP0986389A4 (de)	2001-09-12
HUP0003958A3 (en)	2001-06-28
DE69827000D1 (de)	2004-11-18
CA2291251A1 (en)	1998-12-03
ID24383A (id)	2000-07-13
SK159899A3 (en)	2000-06-12
US20040147754A1 (en)	2004-07-29
AU7708998A (en)	1998-12-30
CN1268889A (zh)	2000-10-04
NO995796L (no)	1999-11-26
BG104034A (en)	2000-11-30
JP2002514222A (ja)	2002-05-14
US6716985B2 (en)	2004-04-06
US6489347B1 (en)	2002-12-03
BR9809687A (pt)	2000-07-11
EP0986389B1 (de)	2004-10-13

Publication	Publication Date	Title
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OA11223A (en)	2003-06-17	Novel process
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KR20070064370A (ko)	2007-06-20	4-(3-설폰일페닐)-피페리딘의 합성 공정
EP1074550B1 (de)	2003-01-29	Verfahren zur Herstellung von 3-substituierten 4-Phenyl-Piperidin Derivaten
WO2001029031A1 (en)	2001-04-26	Process for the preparation of paroxetine
WO2001029032A1 (en)	2001-04-26	Process for the preparation of paroxetine
NO174669B (no)	1994-03-07	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzotiopyranylaminer
EP1347960A1 (de)	2003-10-01	Verfahren zur herstellung von (+)-trans-4-p-fluorophenyl-3-hydroxymethyl-1-methylpiperidin
EP1124802A1 (de)	2001-08-22	Verfahren zur herstellung von 4-arylpiperidin-3-carbinolen und verwandte verbindungen
AU1563002A (en)	2002-03-28	Novel process
KR20010013102A (ko)	2001-02-26	신규한 방법
US20010053862A1 (en)	2001-12-20	Process for preparing arylpiperidine carbinol intermediates and derivatives
US4302590A (en)	1981-11-24	Intermediates for the preparation of 4-aryloxy-3-phenylpiperidines
JPH07103098B2 (ja)	1995-11-08	１‐置換（ｓ）‐および（ｒ）‐２‐アミノメチルピロリジン類の有効な立体保存的合成およびその中間体
US4424357A (en)	1984-01-03	Process for preparing 4-aryloxy-3-phenylpiperidines
CZ421999A3 (cs)	2000-05-17	Nový způsob
JP2000515534A (ja)	2000-11-21	３，３―二置換ピペリジンの製造方法
EP1140832A1 (de)	2001-10-10	Verfahren zur herstellung von arylpiperidincarbinol-zwischenprodukten und derivaten
AU2001226773A1 (en)	2002-07-16	Process for preparing (plus or minus) trans-4-p-fluorophenyl-3-hydroxymethyl-1-methylpiperidine