JPS6135177B2 - - Google Patents
Info
- Publication number
- JPS6135177B2 JPS6135177B2 JP56170536A JP17053681A JPS6135177B2 JP S6135177 B2 JPS6135177 B2 JP S6135177B2 JP 56170536 A JP56170536 A JP 56170536A JP 17053681 A JP17053681 A JP 17053681A JP S6135177 B2 JPS6135177 B2 JP S6135177B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- mol
- alkyl
- hydrogen
- piperidine
- 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
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003053 piperidines Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- -1 methylenedioxy Chemical group 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 239000000047 product Substances 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 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-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
- 239000000284 extract Substances 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 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
- 238000002474 experimental method Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 206010015995 Eyelid ptosis Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 239000012141 concentrate Substances 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
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 201000003004 ptosis Diseases 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000725 suspension 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
- IWYDHOAUDWTVEP-ZETCQYMHSA-M (S)-mandelate Chemical compound [O-]C(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-M 0.000 description 2
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 2
- XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- WGIFUQXAAHCOJU-UHFFFAOYSA-N [4-[(4-fluorophenyl)methoxy]piperidin-1-yl]-(4-nitrophenyl)methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)N1CCC(OCC=2C=CC(F)=CC=2)CC1 WGIFUQXAAHCOJU-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical class [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000006239 protecting group Chemical group 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
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 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 1
- 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 1
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 1
- JAZXLDNKNWMUTJ-UHFFFAOYSA-N 1-benzyl-4-[(3,4,5-trimethoxyphenyl)methoxy]piperidine Chemical compound COC1=C(OC)C(OC)=CC(COC2CCN(CC=3C=CC=CC=3)CC2)=C1 JAZXLDNKNWMUTJ-UHFFFAOYSA-N 0.000 description 1
- BPPZXJZYCOETDA-UHFFFAOYSA-N 1-benzylpiperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC=C1 BPPZXJZYCOETDA-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-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
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000004130 Blepharoptosis Diseases 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
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012259 ether extract Substances 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960002888 oxitriptan Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000003826 tablet Substances 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 |
|---|---|---|---|
| CA000388595A CA1173039A (en) | 1981-10-23 | 1981-10-23 | 4-benzyloxypiperidine compounds |
| 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 |
| FI813330A FI77850C (fi) | 1981-10-23 | 1981-10-23 | Foerfarande foer framstaellning av 4-bensyloxi- eller 4-naftylmetoxipiperidinderivat, vilka har antidepressiv verkan. |
| AU76769/81A AU545739B2 (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives |
| DK469381A DK157853C (da) | 1981-10-23 | 1981-10-23 | Analogifremgangsmaade til fremstilling af 4-benzyloxypiperidinderivater |
| NZ198748A NZ198748A (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives and pharmaceutical compositions |
| ZA817373A ZA817373B (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives,their preparation and pharmaceutical compositions containing them |
| NO813577A NO153890C (no) | 1981-10-23 | 1981-10-23 | Analogifremgangsmaate for fremstilling av terapeutisk aktive piperidinderivater. |
| ES506500A ES506500A0 (es) | 1981-10-23 | 1981-10-23 | Procedimiento de preparacion de derivados de piperidina |
| PT73875A PT73875B (fr) | 1981-10-23 | 1981-10-23 | Procede de preparation de derives de piperidine applicables en therapeutique |
| IE2500/81A IE51707B1 (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives,their preparation and pharmaceutical compositions containing them |
| GR66337A GR75364B (enrdf_load_stackoverflow) | 1981-10-23 | 1981-10-23 |
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000388595A CA1173039A (en) | 1981-10-23 | 1981-10-23 | 4-benzyloxypiperidine compounds |
| 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 |
| FI813330A FI77850C (fi) | 1981-10-23 | 1981-10-23 | Foerfarande foer framstaellning av 4-bensyloxi- eller 4-naftylmetoxipiperidinderivat, vilka har antidepressiv verkan. |
| AU76769/81A AU545739B2 (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives |
| DK469381A DK157853C (da) | 1981-10-23 | 1981-10-23 | Analogifremgangsmaade til fremstilling af 4-benzyloxypiperidinderivater |
| NZ198748A NZ198748A (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives and pharmaceutical compositions |
| ZA817373A ZA817373B (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives,their preparation and pharmaceutical compositions containing them |
| NO813577A NO153890C (no) | 1981-10-23 | 1981-10-23 | Analogifremgangsmaate for fremstilling av terapeutisk aktive piperidinderivater. |
| ES506500A ES506500A0 (es) | 1981-10-23 | 1981-10-23 | Procedimiento de preparacion de derivados de piperidina |
| PT73875A PT73875B (fr) | 1981-10-23 | 1981-10-23 | Procede de preparation de derives de piperidine applicables en therapeutique |
| IE2500/81A IE51707B1 (en) | 1981-10-23 | 1981-10-23 | Piperidine derivatives,their preparation and pharmaceutical compositions containing them |
| GR66337A GR75364B (enrdf_load_stackoverflow) | 1981-10-23 | 1981-10-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5872565A JPS5872565A (ja) | 1983-04-30 |
| JPS6135177B2 true JPS6135177B2 (enrdf_load_stackoverflow) | 1986-08-12 |
Family
ID=27582840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56170536A Granted 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 |
Country Status (12)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02148948U (enrdf_load_stackoverflow) * | 1989-05-17 | 1990-12-18 | ||
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5169855A (en) * | 1990-03-28 | 1992-12-08 | Du Pont Merck Pharmaceutical Company | Piperidine ether derivatives as psychotropic drugs or plant fungicides |
-
1981
- 1981-10-23 NO NO813577A patent/NO153890C/no unknown
- 1981-10-23 FI FI813330A patent/FI77850C/fi not_active IP Right Cessation
- 1981-10-23 ES ES506500A patent/ES506500A0/es active Granted
- 1981-10-23 GR GR66337A patent/GR75364B/el unknown
- 1981-10-23 ZA ZA817373A patent/ZA817373B/xx unknown
- 1981-10-23 JP JP56170536A patent/JPS5872565A/ja active Granted
- 1981-10-23 NZ NZ198748A patent/NZ198748A/en unknown
- 1981-10-23 CA CA000388595A patent/CA1173039A/en not_active Expired
- 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 IE IE2500/81A patent/IE51707B1/en not_active IP Right Cessation
- 1981-10-23 AU AU76769/81A patent/AU545739B2/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02148948U (enrdf_load_stackoverflow) * | 1989-05-17 | 1990-12-18 | ||
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GR75364B (enrdf_load_stackoverflow) | 1984-07-13 |
| IE812500L (en) | 1983-04-21 |
| ZA817373B (en) | 1983-03-30 |
| FI77850C (fi) | 1989-05-10 |
| DK157853C (da) | 1990-08-06 |
| DK157853B (da) | 1990-02-26 |
| AU545739B2 (en) | 1985-08-01 |
| NO153890C (no) | 1986-06-11 |
| PT73875B (fr) | 1983-01-25 |
| NO153890B (no) | 1986-03-03 |
| DK469381A (da) | 1983-04-24 |
| IE51707B1 (en) | 1987-02-18 |
| NO813577L (no) | 1983-04-25 |
| FI77850B (fi) | 1989-01-31 |
| PT73875A (fr) | 1981-11-01 |
| ES8206476A1 (es) | 1982-08-16 |
| JPS5872565A (ja) | 1983-04-30 |
| CA1173039A (en) | 1984-08-21 |
| NZ198748A (en) | 1984-08-24 |
| FI813330L (fi) | 1983-04-24 |
| AU7676981A (en) | 1983-04-28 |
| ES506500A0 (es) | 1982-08-16 |
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