CA1173039A - 4-benzyloxypiperidine compounds - Google Patents
4-benzyloxypiperidine compoundsInfo
- Publication number
- CA1173039A CA1173039A CA000388595A CA388595A CA1173039A CA 1173039 A CA1173039 A CA 1173039A CA 000388595 A CA000388595 A CA 000388595A CA 388595 A CA388595 A CA 388595A CA 1173039 A CA1173039 A CA 1173039A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- general formula
- hydrogen atom
- alkyl
- radicals
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- ILJHWVWEYBJDDM-UHFFFAOYSA-N 4-phenylmethoxypiperidine Chemical class C=1C=CC=CC=1COC1CCNCC1 ILJHWVWEYBJDDM-UHFFFAOYSA-N 0.000 title 1
- -1 alkoxycarbonyl radical Chemical class 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 150000003053 piperidines Chemical class 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 claims abstract description 6
- QIWNOVRXWQPVIY-UHFFFAOYSA-N propylbenzene Chemical compound [CH2]CCC1=CC=CC=C1 QIWNOVRXWQPVIY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000001430 anti-depressive effect Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 206010015995 Eyelid ptosis Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 206010028347 Muscle twitching Diseases 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 201000003004 ptosis Diseases 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- VEXLZSWFSWYAON-UHFFFAOYSA-N (4-chlorophenyl)-(4-hydroxypiperidin-1-yl)methanone Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(Cl)C=C1 VEXLZSWFSWYAON-UHFFFAOYSA-N 0.000 description 2
- GKGCPWOZAGTHMX-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-(4-nitrophenyl)methanone Chemical compound C1CC(O)CCN1C(=O)C1=CC=C([N+]([O-])=O)C=C1 GKGCPWOZAGTHMX-UHFFFAOYSA-N 0.000 description 2
- DZQJPPKZMLZEDA-UHFFFAOYSA-N (4-nitrophenyl)-[4-[(3,4,5-trimethoxyphenyl)methoxy]piperidin-1-yl]methanone Chemical compound COC1=C(OC)C(OC)=CC(COC2CCN(CC2)C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 DZQJPPKZMLZEDA-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- IWYDHOAUDWTVEP-ZETCQYMHSA-M (S)-mandelate Chemical compound [O-]C(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-M 0.000 description 1
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 1
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 1
- AFQWTJFPNZJKGL-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-4-[(3,4,5-trimethoxyphenyl)methoxy]piperidine Chemical compound COC1=C(OC)C(OC)=CC(COC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=C1 AFQWTJFPNZJKGL-UHFFFAOYSA-N 0.000 description 1
- UWOVDQAMRNZVIM-UHFFFAOYSA-N 4-[(3,4,5-trimethoxyphenyl)methoxy]piperidine Chemical compound COC1=C(OC)C(OC)=CC(COC2CCNCC2)=C1 UWOVDQAMRNZVIM-UHFFFAOYSA-N 0.000 description 1
- OVUJZMQPHDVQLL-UHFFFAOYSA-N 4-[(4-chlorophenyl)methoxy]-1-methylpiperidine Chemical compound C1CN(C)CCC1OCC1=CC=C(Cl)C=C1 OVUJZMQPHDVQLL-UHFFFAOYSA-N 0.000 description 1
- HKWRVHLLZSIWAR-UHFFFAOYSA-N 4-[(4-fluorophenyl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1COC1CCNCC1 HKWRVHLLZSIWAR-UHFFFAOYSA-N 0.000 description 1
- TYZNPXDFDHBMNU-UHFFFAOYSA-N 4-phenylmethoxypiperidine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1COC1CCNCC1 TYZNPXDFDHBMNU-UHFFFAOYSA-N 0.000 description 1
- IEMIRQHGRFKGTC-UHFFFAOYSA-N C(C(O)C1=CC=CC=C1)(=O)O.COC=1C=C(COC2CCNCC2)C=C(C1OC)OC Chemical compound C(C(O)C1=CC=CC=C1)(=O)O.COC=1C=C(COC2CCNCC2)C=C(C1OC)OC IEMIRQHGRFKGTC-UHFFFAOYSA-N 0.000 description 1
- XVRAODOSQLKMIW-UHFFFAOYSA-N C(C(O)C1=CC=CC=C1)(=O)O.FC1=CC=C(COC2CCNCC2)C=C1 Chemical compound C(C(O)C1=CC=CC=C1)(=O)O.FC1=CC=C(COC2CCNCC2)C=C1 XVRAODOSQLKMIW-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229960002888 oxitriptan Drugs 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK469381A DK157853C (da) | 1981-10-23 | 1981-10-23 | Analogifremgangsmaade til fremstilling af 4-benzyloxypiperidinderivater |
| FI813330A FI77850C (fi) | 1981-10-23 | 1981-10-23 | Foerfarande foer framstaellning av 4-bensyloxi- eller 4-naftylmetoxipiperidinderivat, vilka har antidepressiv verkan. |
| ES506500A ES506500A0 (es) | 1981-10-23 | 1981-10-23 | Procedimiento de preparacion de derivados de piperidina |
| IE2500/81A IE51707B1 (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives,their preparation and pharmaceutical compositions containing them |
| ZA817373A ZA817373B (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives,their preparation and pharmaceutical compositions containing them |
| NZ198748A NZ198748A (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives and pharmaceutical compositions |
| NO813577A NO153890C (no) | 1981-10-23 | 1981-10-23 | Analogifremgangsmaate for fremstilling av terapeutisk aktive piperidinderivater. |
| AU76769/81A AU545739B2 (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives |
| JP56170536A JPS5872565A (ja) | 1981-10-23 | 1981-10-23 | ピペリジン誘導体およびその製造方法 |
| CA000388595A CA1173039A (en) | 1981-10-23 | 1981-10-23 | 4-benzyloxypiperidine compounds |
| GR66337A GR75364B (enrdf_load_stackoverflow) | 1981-10-23 | 1981-10-23 | |
| PT73875A PT73875B (fr) | 1981-10-23 | 1981-10-23 | Procede de preparation de derives de piperidine applicables en therapeutique |
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK469381A DK157853C (da) | 1981-10-23 | 1981-10-23 | Analogifremgangsmaade til fremstilling af 4-benzyloxypiperidinderivater |
| FI813330A FI77850C (fi) | 1981-10-23 | 1981-10-23 | Foerfarande foer framstaellning av 4-bensyloxi- eller 4-naftylmetoxipiperidinderivat, vilka har antidepressiv verkan. |
| ES506500A ES506500A0 (es) | 1981-10-23 | 1981-10-23 | Procedimiento de preparacion de derivados de piperidina |
| IE2500/81A IE51707B1 (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives,their preparation and pharmaceutical compositions containing them |
| ZA817373A ZA817373B (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives,their preparation and pharmaceutical compositions containing them |
| NZ198748A NZ198748A (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives and pharmaceutical compositions |
| NO813577A NO153890C (no) | 1981-10-23 | 1981-10-23 | Analogifremgangsmaate for fremstilling av terapeutisk aktive piperidinderivater. |
| AU76769/81A AU545739B2 (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives |
| JP56170536A JPS5872565A (ja) | 1981-10-23 | 1981-10-23 | ピペリジン誘導体およびその製造方法 |
| CA000388595A CA1173039A (en) | 1981-10-23 | 1981-10-23 | 4-benzyloxypiperidine compounds |
| GR66337A GR75364B (enrdf_load_stackoverflow) | 1981-10-23 | 1981-10-23 | |
| PT73875A PT73875B (fr) | 1981-10-23 | 1981-10-23 | Procede de preparation de derives de piperidine applicables en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1173039A true CA1173039A (en) | 1984-08-21 |
Family
ID=27582840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000388595A Expired CA1173039A (en) | 1981-10-23 | 1981-10-23 | 4-benzyloxypiperidine compounds |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02148948U (enrdf_load_stackoverflow) * | 1989-05-17 | 1990-12-18 | ||
| US5169855A (en) * | 1990-03-28 | 1992-12-08 | Du Pont Merck Pharmaceutical Company | Piperidine ether derivatives as psychotropic drugs or plant fungicides |
| JPH0535676U (ja) * | 1991-06-06 | 1993-05-14 | 株式会社カネマス | 乾燥海草の水戻し用パツク |
-
1981
- 1981-10-23 GR GR66337A patent/GR75364B/el unknown
- 1981-10-23 CA CA000388595A patent/CA1173039A/en not_active Expired
- 1981-10-23 FI FI813330A patent/FI77850C/fi not_active IP Right Cessation
- 1981-10-23 AU AU76769/81A patent/AU545739B2/en not_active Ceased
- 1981-10-23 IE IE2500/81A patent/IE51707B1/en not_active IP Right Cessation
- 1981-10-23 ZA ZA817373A patent/ZA817373B/xx unknown
- 1981-10-23 ES ES506500A patent/ES506500A0/es active Granted
- 1981-10-23 DK DK469381A patent/DK157853C/da not_active IP Right Cessation
- 1981-10-23 PT PT73875A patent/PT73875B/pt unknown
- 1981-10-23 NO NO813577A patent/NO153890C/no unknown
- 1981-10-23 JP JP56170536A patent/JPS5872565A/ja active Granted
- 1981-10-23 NZ NZ198748A patent/NZ198748A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI77850B (fi) | 1989-01-31 |
| GR75364B (enrdf_load_stackoverflow) | 1984-07-13 |
| DK469381A (da) | 1983-04-24 |
| AU7676981A (en) | 1983-04-28 |
| NO153890B (no) | 1986-03-03 |
| FI77850C (fi) | 1989-05-10 |
| ZA817373B (en) | 1983-03-30 |
| JPS5872565A (ja) | 1983-04-30 |
| NO153890C (no) | 1986-06-11 |
| PT73875B (fr) | 1983-01-25 |
| ES8206476A1 (es) | 1982-08-16 |
| PT73875A (fr) | 1981-11-01 |
| DK157853C (da) | 1990-08-06 |
| ES506500A0 (es) | 1982-08-16 |
| JPS6135177B2 (enrdf_load_stackoverflow) | 1986-08-12 |
| AU545739B2 (en) | 1985-08-01 |
| FI813330L (fi) | 1983-04-24 |
| IE51707B1 (en) | 1987-02-18 |
| NZ198748A (en) | 1984-08-24 |
| IE812500L (en) | 1983-04-21 |
| DK157853B (da) | 1990-02-26 |
| NO813577L (no) | 1983-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |