NO310354B1 - Fenoksymetylpiperidin-derivater, fremgangsmåte ved fremstilling og anvendelse av dem, samt medikamenter inneholdendedem - Google Patents

Fenoksymetylpiperidin-derivater, fremgangsmåte ved fremstilling og anvendelse av dem, samt medikamenter inneholdendedem Download PDF

Info

Publication number: NO310354B1
Authority: NO; Norway
Prior art keywords: formula; compound; hydrogen; dimethylphenoxymethyl; methylpiperidine
Prior art date: 1997-04-03

Application number

NO19981495A

Other languages

English (en)

Norwegian (no)

Other versions

NO981495D0 (no

NO981495L (no

Inventor

Lee Allen Flippin

Xiao-Fa Lin

David Garrett Loughhead

Robert James Weikert

Original Assignee

Hoffmann La Roche

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.)

1997-04-03

Filing date

1998-04-02

Publication date

2001-06-25

1998-04-02 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1998-04-02 Publication of NO981495D0 publication Critical patent/NO981495D0/no

1998-10-05 Publication of NO981495L publication Critical patent/NO981495L/no

2001-06-25 Publication of NO310354B1 publication Critical patent/NO310354B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 86
238000000034 method Methods 0.000 title claims description 41
239000003814 drug Substances 0.000 title claims description 12
230000008569 process Effects 0.000 title claims description 3
ZZKAAWZQFPDZDW-UHFFFAOYSA-N 1-(phenoxymethyl)piperidine Chemical class C1CCCCN1COC1=CC=CC=C1 ZZKAAWZQFPDZDW-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 185
-1 di-substituted phenyl Chemical group 0.000 claims description 100
229910052739 hydrogen Inorganic materials 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 60
238000006243 chemical reaction Methods 0.000 claims description 45
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
208000004296 neuralgia Diseases 0.000 claims description 19
208000021722 neuropathic pain Diseases 0.000 claims description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
239000003195 sodium channel blocking agent Substances 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 15
150000002431 hydrogen Chemical group 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 9
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
230000001225 therapeutic effect Effects 0.000 claims description 7
UBHFGBSNTIMLPW-LBPRGKRZSA-N (3s)-3-[(4-bromo-2,6-dimethylphenoxy)methyl]piperidine Chemical compound CC1=CC(Br)=CC(C)=C1OC[C@@H]1CNCCC1 UBHFGBSNTIMLPW-LBPRGKRZSA-N 0.000 claims description 6
150000001204 N-oxides Chemical class 0.000 claims description 6
239000000654 additive Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
YDYKRTYDLMQIDI-UHFFFAOYSA-N 3-[(4-bromo-2,6-dimethylphenoxy)methyl]-1-methylpiperidine Chemical compound C1N(C)CCCC1COC1=C(C)C=C(Br)C=C1C YDYKRTYDLMQIDI-UHFFFAOYSA-N 0.000 claims description 5
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238000004519 manufacturing process Methods 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
GEHBAXIFCZXOSO-AWEZNQCLSA-N (3s)-3-[(2,6-dimethylphenoxy)methyl]-1-methylpiperidine Chemical compound C1N(C)CCC[C@@H]1COC1=C(C)C=CC=C1C GEHBAXIFCZXOSO-AWEZNQCLSA-N 0.000 claims description 4
YDYKRTYDLMQIDI-ZDUSSCGKSA-N (3s)-3-[(4-bromo-2,6-dimethylphenoxy)methyl]-1-methylpiperidine Chemical compound C1N(C)CCC[C@@H]1COC1=C(C)C=C(Br)C=C1C YDYKRTYDLMQIDI-ZDUSSCGKSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
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125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
229940125794 sodium channel blocker Drugs 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
238000010511 deprotection reaction Methods 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
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 claims description 3
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GEHBAXIFCZXOSO-UHFFFAOYSA-N 3-[(2,6-dimethylphenoxy)methyl]-1-methylpiperidine Chemical compound C1N(C)CCCC1COC1=C(C)C=CC=C1C GEHBAXIFCZXOSO-UHFFFAOYSA-N 0.000 claims description 2
LDNYJNSOBACMBY-UHFFFAOYSA-N 3-[(4-bromo-2,6-dimethylphenoxy)methyl]-1-methyl-1-oxidopiperidin-1-ium Chemical compound CC1=CC(Br)=CC(C)=C1OCC1C[N+](C)([O-])CCC1 LDNYJNSOBACMBY-UHFFFAOYSA-N 0.000 claims description 2
UBHFGBSNTIMLPW-UHFFFAOYSA-N 3-[(4-bromo-2,6-dimethylphenoxy)methyl]piperidine Chemical compound CC1=CC(Br)=CC(C)=C1OCC1CNCCC1 UBHFGBSNTIMLPW-UHFFFAOYSA-N 0.000 claims description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
125000004965 chloroalkyl group Chemical group 0.000 claims 1
230000003647 oxidation Effects 0.000 claims 1
238000007254 oxidation reaction Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
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239000000243 solution Substances 0.000 description 38
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208000004454 Hyperalgesia Diseases 0.000 description 28
241000700159 Rattus Species 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
208000002193 Pain Diseases 0.000 description 21
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 21
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239000003960 organic solvent Substances 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
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239000007787 solid Substances 0.000 description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
206010053552 allodynia Diseases 0.000 description 14
239000010410 layer Substances 0.000 description 14
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
241001465754 Metazoa Species 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
230000001684 chronic effect Effects 0.000 description 12
239000012267 brine Substances 0.000 description 11
230000000694 effects Effects 0.000 description 11
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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102000018674 Sodium Channels Human genes 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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239000002244 precipitate Substances 0.000 description 8
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SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
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GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
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238000003745 diagnosis Methods 0.000 description 1
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
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YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical class CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 description 1
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239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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235000020824 obesity Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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239000006179 pH buffering agent Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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239000008177 pharmaceutical agent Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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239000013589 supplement Substances 0.000 description 1
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238000011477 surgical intervention Methods 0.000 description 1
230000001360 synchronised effect Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
VVKCNYOQHJEXRB-UHFFFAOYSA-N tert-butyl chloro carbonate Chemical compound CC(C)(C)OC(=O)OCl VVKCNYOQHJEXRB-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
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125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
230000018405 transmission of nerve impulse Effects 0.000 description 1
230000008733 trauma Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000007306 turnover Effects 0.000 description 1
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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
- 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
- A61P23/00—Anaesthetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Anesthesiology (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO19981495A 1997-04-03 1998-04-02 Fenoksymetylpiperidin-derivater, fremgangsmåte ved fremstilling og anvendelse av dem, samt medikamenter inneholdendedem NO310354B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US4268197P	1997-04-03	1997-04-03
US6975597P	1997-12-16	1997-12-16

Publications (3)

Publication Number	Publication Date
NO981495D0 NO981495D0 (no)	1998-04-02
NO981495L NO981495L (no)	1998-10-05
NO310354B1 true NO310354B1 (no)	2001-06-25

Family

ID=26719512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19981495A NO310354B1 (no)	1997-04-03	1998-04-02	Fenoksymetylpiperidin-derivater, fremgangsmåte ved fremstilling og anvendelse av dem, samt medikamenter inneholdendedem

Country Status (13)

Country	Link
EP (1)	EP0869119A1 (fr)
JP (1)	JP2938432B2 (fr)
KR (1)	KR100257958B1 (fr)
CN (1)	CN1194977A (fr)
AU (1)	AU743476B2 (fr)
CA (1)	CA2232147A1 (fr)
CZ (1)	CZ98898A3 (fr)
HU (1)	HUP9800707A3 (fr)
IL (1)	IL123860A0 (fr)
MA (1)	MA26480A1 (fr)
NO (1)	NO310354B1 (fr)
NZ (1)	NZ330017A (fr)
PL (1)	PL325687A1 (fr)

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GB9808015D0 (en) *	1998-04-15	1998-06-17	United Medical And Dental Scho	Protection of the nervous system from the effects of inflammatory disease
US6420354B1 (en)	1998-06-08	2002-07-16	Advanced Medicine, Inc.	Sodium channel drugs and uses
DE19907385A1 (de) *	1999-02-20	2000-08-24	Boehringer Ingelheim Pharma	Neue substituierte 3-Phenoxy- und 3-Phenylalkyloxy-2-phenyl-propylamine
EP1182193A4 (fr) *	1999-04-09	2002-09-11	Mochida Pharm Co Ltd	Remedes pour douleurs neurogenes
US6479498B1 (en)	1999-06-04	2002-11-12	Theravance, Inc.	Sodium channel drugs and uses
US6756400B2 (en)	2000-08-31	2004-06-29	Theravance, Inc.	Sodium channel modulators
US6646012B2 (en)	2001-01-16	2003-11-11	Theravance, Inc.	Sodium channel modulators
JPWO2004011430A1 (ja) *	2002-07-25	2005-11-24	アステラス製薬株式会社	ナトリウムチャネル阻害剤
GB0218827D0 (en) *	2002-08-13	2002-09-18	Syngenix Ltd	Anaesthetic compounds and conjugates thereof

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GB1203149A (en) *	1968-06-10	1970-08-26	Ici Ltd	Piperidine derivatives
IE912760A1 (en) *	1990-08-06	1992-02-12	Smith Kline French Lab	Compounds
FR2667317B1 (fr) *	1990-10-02	1992-12-04	Synthelabo	Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique.
GB9226111D0 (en) *	1992-12-15	1993-02-10	Smithkline Beecham Plc	Madicaments

1998
- 1998-03-16 CA CA002232147A patent/CA2232147A1/fr not_active Abandoned
- 1998-03-18 AU AU59379/98A patent/AU743476B2/en not_active Ceased
- 1998-03-23 NZ NZ330017A patent/NZ330017A/en unknown
- 1998-03-27 IL IL12386098A patent/IL123860A0/xx unknown
- 1998-03-30 HU HU9800707A patent/HUP9800707A3/hu unknown
- 1998-04-01 JP JP10088372A patent/JP2938432B2/ja not_active Expired - Fee Related
- 1998-04-01 MA MA25019A patent/MA26480A1/fr unknown
- 1998-04-01 CZ CZ98988A patent/CZ98898A3/cs unknown
- 1998-04-02 EP EP98106026A patent/EP0869119A1/fr not_active Withdrawn
- 1998-04-02 CN CN98106139A patent/CN1194977A/zh active Pending
- 1998-04-02 NO NO19981495A patent/NO310354B1/no not_active IP Right Cessation
- 1998-04-02 PL PL98325687A patent/PL325687A1/xx unknown
- 1998-04-03 KR KR1019980011748A patent/KR100257958B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR19980081053A (ko)	1998-11-25
HU9800707D0 (en)	1998-05-28
NZ330017A (en)	1999-04-29
HUP9800707A2 (hu)	1999-05-28
JPH10287649A (ja)	1998-10-27
NO981495D0 (no)	1998-04-02
CZ98898A3 (cs)	1998-10-14
IL123860A0 (en)	1998-10-30
KR100257958B1 (ko)	2000-07-01
HUP9800707A3 (en)	1999-06-28
CA2232147A1 (fr)	1998-10-03
MA26480A1 (fr)	2004-12-20
EP0869119A1 (fr)	1998-10-07
CN1194977A (zh)	1998-10-07
AU5937998A (en)	1998-10-08
AU743476B2 (en)	2002-01-24
PL325687A1 (en)	1998-10-12
JP2938432B2 (ja)	1999-08-23
NO981495L (no)	1998-10-05

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2003-12-08	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN OCTOBER 2003

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