CA1088940A - 4-(7-bromo-5-methoxy-2-benzofuranyl)-1,2,3,6- tetrahydropyridine and -piperidine compounds - Google Patents
4-(7-bromo-5-methoxy-2-benzofuranyl)-1,2,3,6- tetrahydropyridine and -piperidine compoundsInfo
- Publication number
- CA1088940A CA1088940A CA266,466A CA266466A CA1088940A CA 1088940 A CA1088940 A CA 1088940A CA 266466 A CA266466 A CA 266466A CA 1088940 A CA1088940 A CA 1088940A
- Authority
- CA
- Canada
- Prior art keywords
- general formula
- bromo
- methoxy
- methyl
- acid
- 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
- YFHIBXPICOOGCO-UHFFFAOYSA-N 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1,2,3,6-tetrahydropyridine Chemical compound BrC1=CC(=CC=2C=C(OC21)C=2CCNCC2)OC YFHIBXPICOOGCO-UHFFFAOYSA-N 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 48
- -1 piperidine com-pounds Chemical class 0.000 claims description 25
- 150000003254 radicals Chemical class 0.000 claims description 12
- 150000007524 organic acids Chemical class 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- MAKLWNAYDCEBJB-UHFFFAOYSA-N 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-methyl-3,6-dihydro-2h-pyridine Chemical compound C=1C2=CC(OC)=CC(Br)=C2OC=1C1=CCN(C)CC1 MAKLWNAYDCEBJB-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- WZXHSWVDAYOFPE-UHFFFAOYSA-N brofaromine Chemical compound C=1C2=CC(OC)=CC(Br)=C2OC=1C1CCNCC1 WZXHSWVDAYOFPE-UHFFFAOYSA-N 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- CSOKKONGNIEHFO-UHFFFAOYSA-N 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-methylpiperidine Chemical compound C=1C2=CC(OC)=CC(Br)=C2OC=1C1CCN(C)CC1 CSOKKONGNIEHFO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 7
- 102000010909 Monoamine Oxidase Human genes 0.000 abstract description 3
- 108010062431 Monoamine oxidase Proteins 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 150000003053 piperidines Chemical class 0.000 abstract 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 abstract description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 abstract description 2
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- 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 abstract description 2
- 229960003147 reserpine Drugs 0.000 abstract 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 abstract description 2
- 235000013350 formula milk Nutrition 0.000 description 54
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000001828 Gelatine Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 229920000159 gelatin Polymers 0.000 description 7
- 235000019322 gelatine Nutrition 0.000 description 7
- 239000000829 suppository Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000008298 dragée Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
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- 239000000454 talc Substances 0.000 description 5
- 235000012222 talc Nutrition 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- 241000700159 Rattus Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
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- 235000019253 formic acid Nutrition 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- PUYKEOGYPYITCW-UHFFFAOYSA-N 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)piperidine;hydron;chloride Chemical compound Cl.C=1C2=CC(OC)=CC(Br)=C2OC=1C1CCNCC1 PUYKEOGYPYITCW-UHFFFAOYSA-N 0.000 description 3
- WKUCLUMAURVHBQ-UHFFFAOYSA-N 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)pyridine Chemical compound C=1C2=CC(OC)=CC(Br)=C2OC=1C1=CC=NC=C1 WKUCLUMAURVHBQ-UHFFFAOYSA-N 0.000 description 3
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- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
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- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 150000007530 organic bases Chemical group 0.000 description 1
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- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
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- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
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- 239000010948 rhodium Substances 0.000 description 1
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- YPSUCTSXOROPBS-UHFFFAOYSA-N s-methyl chloromethanethioate Chemical compound CSC(Cl)=O YPSUCTSXOROPBS-UHFFFAOYSA-N 0.000 description 1
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
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- 235000013874 shellac Nutrition 0.000 description 1
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
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- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
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- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1530175A CH609054A5 (en) | 1975-11-26 | 1975-11-26 | Process for the preparation of a novel piperidine derivative |
| CH15301/75 | 1975-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088940A true CA1088940A (en) | 1980-11-04 |
Family
ID=4407989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA266,466A Expired CA1088940A (en) | 1975-11-26 | 1976-11-24 | 4-(7-bromo-5-methoxy-2-benzofuranyl)-1,2,3,6- tetrahydropyridine and -piperidine compounds |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5265277A (is") |
| AR (1) | AR214985A1 (is") |
| AT (1) | AT352728B (is") |
| AU (1) | AU507722B2 (is") |
| BE (1) | BE848720R (is") |
| CA (1) | CA1088940A (is") |
| CH (1) | CH609054A5 (is") |
| CS (2) | CS205050B2 (is") |
| CY (1) | CY1179A (is") |
| DD (1) | DD129328A6 (is") |
| DE (1) | DE2653147A1 (is") |
| DK (1) | DK142987C (is") |
| ES (1) | ES453582A2 (is") |
| FR (1) | FR2332754A2 (is") |
| GB (1) | GB1565055A (is") |
| HK (1) | HK16783A (is") |
| IE (1) | IE44084B1 (is") |
| MY (1) | MY8400093A (is") |
| NL (1) | NL7613050A (is") |
| NZ (1) | NZ182716A (is") |
| SE (1) | SE426826B (is") |
| SU (3) | SU679136A3 (is") |
| ZA (1) | ZA777068B (is") |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006524A1 (de) | 1978-06-22 | 1980-01-09 | Ciba-Geigy Ag | Neue Tetrahydropyridin- und Piperidinderivate und deren Säureadditionssalze, Verfahren zu deren Herstellung und solche enthaltende pharmazeutische Zusammensetzungen |
| US5455254A (en) * | 1991-02-15 | 1995-10-03 | Mondadori; Cesare | Substituted benzofuranylpiperidine as a nootropic agent |
| RU2095339C1 (ru) * | 1991-10-17 | 1997-11-10 | Циба-Гейги АГ | Производные гидрохинона в свободном виде или в виде соли, способы их получения, производные пиперидина и способы их получения |
| US5693807A (en) * | 1992-10-14 | 1997-12-02 | Ciba-Geigy Corporation | Substituted hydroquinone derivatives |
| ES2132284T3 (es) * | 1993-08-05 | 1999-08-16 | Hoechst Marion Roussel Inc | Derivados de carbamato de 2-(piperidin-4-il, piridin-4-il y tetrahidropiridin-4-il)-benzofurano-7, su preparacion y su uso como inhibidores de acetilcolinesterasa. |
| CN101810606A (zh) * | 2010-03-12 | 2010-08-25 | 南方医科大学 | 2-(6-羟基-2′,3′-二甲氧基苯基)-6-羟基-7-甲氧基苯骈呋喃在制备单胺氧化酶抑制剂中的应用 |
| US8796306B2 (en) | 2010-06-23 | 2014-08-05 | Sumitomo Chemical Company, Limited | Noxious arthropod controlling composition and heterocyclic compound |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH592656A5 (is") * | 1973-03-02 | 1977-10-31 | Ciba Geigy Ag | |
| IE39264B1 (en) * | 1973-05-25 | 1978-08-30 | Ciba Geigy Ag | New pharmaceutical preparations |
-
1975
- 1975-11-26 CH CH1530175A patent/CH609054A5/xx not_active IP Right Cessation
-
1976
- 1976-11-22 AR AR265561A patent/AR214985A1/es active
- 1976-11-23 CY CY1179A patent/CY1179A/xx unknown
- 1976-11-23 GB GB48763/76A patent/GB1565055A/en not_active Expired
- 1976-11-23 NL NL7613050A patent/NL7613050A/xx not_active Application Discontinuation
- 1976-11-23 DE DE19762653147 patent/DE2653147A1/de active Granted
- 1976-11-24 CA CA266,466A patent/CA1088940A/en not_active Expired
- 1976-11-24 DD DD7600195944A patent/DD129328A6/xx unknown
- 1976-11-24 ES ES453582A patent/ES453582A2/es not_active Expired
- 1976-11-24 FR FR7635373A patent/FR2332754A2/fr active Granted
- 1976-11-25 SU SU762422953A patent/SU679136A3/ru active
- 1976-11-25 BE BE172674A patent/BE848720R/xx not_active IP Right Cessation
- 1976-11-25 DK DK532176A patent/DK142987C/da active
- 1976-11-25 IE IE2588/76A patent/IE44084B1/en unknown
- 1976-11-25 ZA ZA00777068A patent/ZA777068B/xx unknown
- 1976-11-25 SE SE7613193A patent/SE426826B/xx not_active IP Right Cessation
- 1976-11-25 AT AT874476A patent/AT352728B/de not_active IP Right Cessation
- 1976-11-25 CS CS767637A patent/CS205050B2/cs unknown
- 1976-11-25 NZ NZ182716A patent/NZ182716A/xx unknown
- 1976-11-25 AU AU19995/76A patent/AU507722B2/en not_active Expired
- 1976-11-25 CS CS767637A patent/CS205049B2/cs unknown
- 1976-11-26 JP JP51141389A patent/JPS5265277A/ja active Granted
-
1978
- 1978-04-17 SU SU782602552A patent/SU680648A3/ru active
- 1978-04-17 SU SU782602551A patent/SU682132A3/ru active
-
1983
- 1983-05-19 HK HK167/83A patent/HK16783A/xx unknown
-
1984
- 1984-12-30 MY MY93/84A patent/MY8400093A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2332754B2 (is") | 1978-12-22 |
| JPS5265277A (en) | 1977-05-30 |
| NZ182716A (en) | 1979-06-19 |
| NL7613050A (nl) | 1977-05-31 |
| DE2653147C2 (is") | 1991-09-19 |
| IE44084L (en) | 1977-05-26 |
| CS205049B2 (en) | 1981-04-30 |
| ES453582A2 (es) | 1978-01-01 |
| SU682132A3 (ru) | 1979-08-25 |
| CS205050B2 (en) | 1981-04-30 |
| DK142987C (da) | 1981-09-21 |
| DD129328A6 (de) | 1978-01-11 |
| BE848720R (fr) | 1977-05-25 |
| ATA874476A (de) | 1979-03-15 |
| IE44084B1 (en) | 1981-08-12 |
| AR214985A1 (es) | 1979-08-31 |
| AT352728B (de) | 1979-10-10 |
| AU1999576A (en) | 1978-06-01 |
| DK532176A (da) | 1977-05-27 |
| DK142987B (da) | 1981-03-09 |
| MY8400093A (en) | 1984-12-31 |
| HK16783A (en) | 1983-05-27 |
| JPS6156234B2 (is") | 1986-12-01 |
| SU680648A3 (ru) | 1979-08-15 |
| DE2653147A1 (de) | 1977-06-08 |
| GB1565055A (en) | 1980-04-16 |
| CY1179A (en) | 1983-06-10 |
| FR2332754A2 (fr) | 1977-06-24 |
| SE7613193L (sv) | 1977-05-27 |
| SE426826B (sv) | 1983-02-14 |
| CH609054A5 (en) | 1979-02-15 |
| ZA777068B (en) | 1978-07-26 |
| AU507722B2 (en) | 1980-02-28 |
| SU679136A3 (ru) | 1979-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |