NO850444L - Fremgangsmaate for fremstilling av (-)-trans-4-(4-fluorfenyl)-3-(4-metoksyfenoksy)-metylperidin eller farmasoeytisk akseptable syreaddisjonssalter derav - Google Patents
Fremgangsmaate for fremstilling av (-)-trans-4-(4-fluorfenyl)-3-(4-metoksyfenoksy)-metylperidin eller farmasoeytisk akseptable syreaddisjonssalter deravInfo
- Publication number
- NO850444L NO850444L NO850444A NO850444A NO850444L NO 850444 L NO850444 L NO 850444L NO 850444 A NO850444 A NO 850444A NO 850444 A NO850444 A NO 850444A NO 850444 L NO850444 L NO 850444L
- Authority
- NO
- Norway
- Prior art keywords
- trans
- acid addition
- fluorophenyl
- compounds
- methylpiperidine
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- 239000002253 acid Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 26
- -1 4-FLUORPHENYL Chemical class 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 6
- 239000002585 base Substances 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 6
- MCEJDDOUERRBGG-RBUKOAKNSA-N (3S,4S)-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)-1-methylpiperidine Chemical compound FC1=CC=C(C=C1)[C@H]1[C@@H](CN(CC1)C)OC1=CC=C(C=C1)OC MCEJDDOUERRBGG-RBUKOAKNSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 71
- 150000001875 compounds Chemical class 0.000 abstract description 38
- 229940076279 serotonin Drugs 0.000 abstract description 13
- 230000003389 potentiating effect Effects 0.000 abstract description 9
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 230000001335 demethylating effect Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000013275 serotonin uptake Effects 0.000 description 9
- DENRAWQJOJWLNZ-KXBFYZLASA-N (3s,4r)-4-(4-fluorophenyl)-3-[(4-methoxyphenoxy)methyl]piperidine Chemical compound C1=CC(OC)=CC=C1OC[C@H]1[C@H](C=2C=CC(F)=CC=2)CCNC1 DENRAWQJOJWLNZ-KXBFYZLASA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000007920 subcutaneous administration Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 231100001274 therapeutic index Toxicity 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000004899 motility Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- WVVMCKRQHBAUPW-JXFKEZNVSA-N (3s,4r)-4-(4-fluorophenyl)-3-[(4-methoxyphenoxy)methyl]-1-methylpiperidine Chemical compound C1=CC(OC)=CC=C1OC[C@H]1[C@H](C=2C=CC(F)=CC=2)CCN(C)C1 WVVMCKRQHBAUPW-JXFKEZNVSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 208000013403 hyperactivity Diseases 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- CXRHUYYZISIIMT-WCQYABFASA-N [(3s,4s)-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-WCQYABFASA-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000012503 blood component Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- NTBIYBAYFBNTCD-UHFFFAOYSA-N dibenzoyl 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000035873 hypermotility Effects 0.000 description 2
- 230000008517 inhibition of serotonin uptake Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 2
- 210000001428 peripheral nervous system Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- VIXHMBLBLJSGIB-UHFFFAOYSA-N 1-fluoro-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(F)C=C1 VIXHMBLBLJSGIB-UHFFFAOYSA-N 0.000 description 1
- PTAPBGKYBVWNJY-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid;hydrate Chemical compound O.C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 PTAPBGKYBVWNJY-UHFFFAOYSA-N 0.000 description 1
- OFKWWALNMPEOSZ-UHFFFAOYSA-N 3-(hydrazinylmethyl)phenol Chemical compound NNCC1=CC=CC(O)=C1 OFKWWALNMPEOSZ-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000012371 Aseptic Filling Methods 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229940123736 Decarboxylase inhibitor Drugs 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 208000007623 Lordosis Diseases 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 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
- 230000036760 body temperature Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003954 decarboxylase inhibitor Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 230000004886 head movement Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000005303 weighing Methods 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
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/577,844 US4585777A (en) | 1984-02-07 | 1984-02-07 | (-)-Trans-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)methylpiperidine for potentiating 5-HT |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO850444L true NO850444L (no) | 1985-08-08 |
Family
ID=24310381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO850444A NO850444L (no) | 1984-02-07 | 1985-02-06 | Fremgangsmaate for fremstilling av (-)-trans-4-(4-fluorfenyl)-3-(4-metoksyfenoksy)-metylperidin eller farmasoeytisk akseptable syreaddisjonssalter derav |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4585777A (es) |
| EP (1) | EP0152273B1 (es) |
| JP (1) | JPS60181071A (es) |
| AT (1) | ATE46146T1 (es) |
| CA (1) | CA1246082A (es) |
| DE (1) | DE3572807D1 (es) |
| DK (1) | DK53285A (es) |
| ES (1) | ES8601131A1 (es) |
| FI (1) | FI850449L (es) |
| GR (1) | GR850309B (es) |
| IE (1) | IE850286L (es) |
| NO (1) | NO850444L (es) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3680184D1 (de) * | 1985-08-10 | 1991-08-14 | Beecham Group Plc | Verfahren zur herstellung von arylpiperidincarbinol. |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| GB8626936D0 (en) * | 1986-11-11 | 1986-12-10 | Ferrosan As | Treatment |
| HU221921B1 (hu) * | 1996-07-08 | 2003-02-28 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására |
| GB9623359D0 (en) * | 1996-11-09 | 1997-01-08 | Smithkline Beecham Plc | Novel process |
| GB9700690D0 (en) | 1997-01-15 | 1997-03-05 | Smithkline Beecham Plc | Novel process |
| IL133140A0 (en) * | 1997-05-29 | 2001-03-19 | Smithkline Beecham Corp | Novel process for the preparation of 4-aryl-piperidines |
| AU2002301956B2 (en) * | 1997-06-10 | 2006-02-09 | Synthon B.V. | 4-phenylpiperidine compounds |
| PT994872E (pt) * | 1997-06-10 | 2001-09-28 | Synthon Bv | Composto de 4-fenilpiperidina |
| CH689805A8 (fr) * | 1998-07-02 | 2000-02-29 | Smithkline Beecham Plc | Méthanesulfonate de paroxétine, procédé pour sa préparation et compositions pharmaceutiques le contenant. |
| GB9914583D0 (en) * | 1999-06-22 | 1999-08-25 | Smithkline Beecham Plc | Novel process |
| CZ20023694A3 (cs) | 2000-05-12 | 2003-05-14 | Synthon B. V. | Tosylátové soli 4-(p-fluorfenyl)-piperidin-3-methanolů |
| US20040087795A1 (en) * | 2000-07-17 | 2004-05-06 | Borrett Gary Thomas | Novel processes for the preparation of 4-phenylpiperidine derivatives |
| WO2002028834A1 (en) * | 2000-10-06 | 2002-04-11 | Smithkline Beecham P.L.C. | Process for the preparation of aryl-piperidine carbinols and intermediates thereof |
| US6777554B2 (en) | 2001-02-05 | 2004-08-17 | Teva Pharmaceutical Industries Ltd. | Preparation of N-methylparoxetine and related intermediate compounds |
| NL1017421C2 (nl) * | 2001-02-21 | 2002-01-15 | Synthon Bv | Werkwijze voor het vervaardigen van paroxetine. |
| AU2002318185A1 (en) | 2001-06-13 | 2002-12-23 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of paroxetine substantially free of alkoxy impurities |
| US20070142389A1 (en) * | 2005-12-20 | 2007-06-21 | Pfizer Inc. | Piperidine derivatives |
| EP2200997B9 (en) | 2007-09-13 | 2016-01-13 | Concert Pharmaceuticals Inc. | Synthesis of deuterated benzodioxoles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
-
1984
- 1984-02-07 US US06/577,844 patent/US4585777A/en not_active Expired - Lifetime
-
1985
- 1985-01-07 CA CA000471622A patent/CA1246082A/en not_active Expired
- 1985-02-04 FI FI850449A patent/FI850449L/fi not_active Application Discontinuation
- 1985-02-04 GR GR850309A patent/GR850309B/el unknown
- 1985-02-06 ES ES540172A patent/ES8601131A1/es not_active Expired
- 1985-02-06 DK DK53285A patent/DK53285A/da not_active Application Discontinuation
- 1985-02-06 DE DE8585300793T patent/DE3572807D1/de not_active Expired
- 1985-02-06 IE IE850286A patent/IE850286L/xx unknown
- 1985-02-06 AT AT85300793T patent/ATE46146T1/de not_active IP Right Cessation
- 1985-02-06 NO NO850444A patent/NO850444L/no unknown
- 1985-02-06 JP JP60020218A patent/JPS60181071A/ja active Granted
- 1985-02-06 EP EP85300793A patent/EP0152273B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK53285D0 (da) | 1985-02-06 |
| FI850449L (fi) | 1985-08-08 |
| IE850286L (en) | 1985-08-07 |
| ATE46146T1 (de) | 1989-09-15 |
| FI850449A0 (fi) | 1985-02-04 |
| ES540172A0 (es) | 1985-11-16 |
| CA1246082A (en) | 1988-12-06 |
| EP0152273B1 (en) | 1989-09-06 |
| JPS60181071A (ja) | 1985-09-14 |
| DE3572807D1 (en) | 1989-10-12 |
| GR850309B (es) | 1985-06-05 |
| JPS6135176B2 (es) | 1986-08-12 |
| EP0152273A2 (en) | 1985-08-21 |
| US4585777A (en) | 1986-04-29 |
| ES8601131A1 (es) | 1985-11-16 |
| EP0152273A3 (en) | 1986-12-30 |
| DK53285A (da) | 1985-08-08 |
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