CA1123440A - 4-(naphthalenyloxy)piperidine derivatives - Google Patents
4-(naphthalenyloxy)piperidine derivativesInfo
- Publication number
- CA1123440A CA1123440A CA355,369A CA355369A CA1123440A CA 1123440 A CA1123440 A CA 1123440A CA 355369 A CA355369 A CA 355369A CA 1123440 A CA1123440 A CA 1123440A
- Authority
- CA
- Canada
- Prior art keywords
- naphthalenyloxy
- formula
- compound
- pharmaceutically acceptable
- acid addition
- 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
- KXEJLUAGLBQHLO-UHFFFAOYSA-N 4-naphthalen-1-yloxypiperidine Chemical class C1CNCCC1OC1=CC=CC2=CC=CC=C12 KXEJLUAGLBQHLO-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000002253 acid Substances 0.000 claims abstract description 42
- -1 hydroxy-methylene Chemical group 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 24
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 230000003287 optical effect Effects 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- CBPIGRLQUAFSQT-UHFFFAOYSA-N 4-naphthalen-2-yloxypiperidine Chemical compound C1CNCCC1OC1=CC=C(C=CC=C2)C2=C1 CBPIGRLQUAFSQT-UHFFFAOYSA-N 0.000 claims description 4
- 230000001603 reducing effect Effects 0.000 claims description 4
- LRRRHEFNMOJHPU-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-naphthalen-2-yloxypiperidin-1-yl)butan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC(OC=2C=C3C=CC=CC3=CC=2)CC1 LRRRHEFNMOJHPU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 230000003197 catalytic effect Effects 0.000 claims 4
- NVNYXWLTQIYZSB-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-naphthalen-1-yloxypiperidin-1-yl)butan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC(OC=2C3=CC=CC=C3C=CC=2)CC1 NVNYXWLTQIYZSB-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 8
- 239000000543 intermediate Substances 0.000 abstract description 6
- 239000000164 antipsychotic agent Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 235000013350 formula milk Nutrition 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- BAGQBTMEEISJLK-UHFFFAOYSA-N 2-fluoronaphthalene Chemical compound C1=CC=CC2=CC(F)=CC=C21 BAGQBTMEEISJLK-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000000701 neuroleptic effect Effects 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 230000002936 tranquilizing effect Effects 0.000 description 6
- HXAOUYGZEOZTJO-UHFFFAOYSA-N 4-chloro-1-(4-fluorophenyl)butan-1-one Chemical compound FC1=CC=C(C(=O)CCCCl)C=C1 HXAOUYGZEOZTJO-UHFFFAOYSA-N 0.000 description 5
- GHEFQKHLHFXSBR-UHFFFAOYSA-N 4-chloro-1-phenylbutan-1-one Chemical compound ClCCCC(=O)C1=CC=CC=C1 GHEFQKHLHFXSBR-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- HLWJLHJPFFHUSK-UHFFFAOYSA-N 1-benzyl-4-naphthalen-2-yloxypiperidine Chemical compound C1CC(OC=2C=C3C=CC=CC3=CC=2)CCN1CC1=CC=CC=C1 HLWJLHJPFFHUSK-UHFFFAOYSA-N 0.000 description 4
- IEBXAXSUZLVHRG-UHFFFAOYSA-N 1-ethyl-4-(5-fluoronaphthalen-1-yl)oxypiperidine Chemical compound C1CN(CC)CCC1OC1=CC=CC2=C(F)C=CC=C12 IEBXAXSUZLVHRG-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000000561 anti-psychotic effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229960003390 magnesium sulfate Drugs 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000003176 neuroleptic agent Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- BPPZXJZYCOETDA-UHFFFAOYSA-N 1-benzylpiperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC=C1 BPPZXJZYCOETDA-UHFFFAOYSA-N 0.000 description 3
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 3
- IITBJHGKSHRLDI-UHFFFAOYSA-N 4-(1-methylnaphthalen-2-yl)oxypiperidine Chemical compound C1=CC2=CC=CC=C2C(C)=C1OC1CCNCC1 IITBJHGKSHRLDI-UHFFFAOYSA-N 0.000 description 3
- UYMOYFJXGJDVJR-UHFFFAOYSA-N 4-(5-fluoronaphthalen-1-yl)oxypiperidine Chemical compound C1=CC=C2C(F)=CC=CC2=C1OC1CCNCC1 UYMOYFJXGJDVJR-UHFFFAOYSA-N 0.000 description 3
- XWYPFKZFRFZKOC-UHFFFAOYSA-N 4-naphthalen-2-yloxypiperidine;hydrochloride Chemical compound Cl.C1CNCCC1OC1=CC=C(C=CC=C2)C2=C1 XWYPFKZFRFZKOC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
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- 239000002775 capsule Substances 0.000 description 3
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- 238000006900 dealkylation reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 125000005936 piperidyl group Chemical group 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
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- 239000007892 solid unit dosage form Substances 0.000 description 3
- 239000003204 tranquilizing agent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- NDOPWUJDBOTUFB-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-naphthalen-2-yloxypiperidin-1-yl)butan-1-one;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C(=O)CCCN1CCC(OC=2C=C3C=CC=CC3=CC=2)CC1 NDOPWUJDBOTUFB-UHFFFAOYSA-N 0.000 description 2
- AKVIVTDXCVUADP-UHFFFAOYSA-N 1-benzyl-4-(5-methoxynaphthalen-1-yl)oxypiperidine;hydrochloride Chemical compound Cl.C1=CC=C2C(OC)=CC=CC2=C1OC(CC1)CCN1CC1=CC=CC=C1 AKVIVTDXCVUADP-UHFFFAOYSA-N 0.000 description 2
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- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 2
- VITFGQNUQBMNKK-UHFFFAOYSA-N 4-(1-methylnaphthalen-2-yl)oxypiperidine;hydrochloride Chemical compound Cl.C1=CC2=CC=CC=C2C(C)=C1OC1CCNCC1 VITFGQNUQBMNKK-UHFFFAOYSA-N 0.000 description 2
- ASYNNGLXRXCQFN-UHFFFAOYSA-N 4-(5-methoxynaphthalen-1-yl)oxypiperidine Chemical compound C1=CC=C2C(OC)=CC=CC2=C1OC1CCNCC1 ASYNNGLXRXCQFN-UHFFFAOYSA-N 0.000 description 2
- DEGKNZKEOABVNO-UHFFFAOYSA-N 4-(5-methoxynaphthalen-1-yl)oxypiperidine;hydrochloride Chemical compound Cl.C1=CC=C2C(OC)=CC=CC2=C1OC1CCNCC1 DEGKNZKEOABVNO-UHFFFAOYSA-N 0.000 description 2
- YOCXGQCVPIYXNV-UHFFFAOYSA-N 4-[4-(trifluoromethyl)naphthalen-2-yl]oxypiperidine Chemical compound C=1C2=CC=CC=C2C(C(F)(F)F)=CC=1OC1CCNCC1 YOCXGQCVPIYXNV-UHFFFAOYSA-N 0.000 description 2
- SJUAXBUXKXMOKG-UHFFFAOYSA-N 4-naphthalen-1-yloxypiperidine;hydrochloride Chemical compound Cl.C1CNCCC1OC1=CC=CC2=CC=CC=C12 SJUAXBUXKXMOKG-UHFFFAOYSA-N 0.000 description 2
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- QEUWOEGDLXKUNJ-UHFFFAOYSA-N naphthalene;hydrofluoride Chemical compound F.C1=CC=CC2=CC=CC=C21 QEUWOEGDLXKUNJ-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
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- 239000002026 chloroform extract Substances 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical class *C#N 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical class C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 229960000632 dexamfetamine Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- JBZVNNUFGSXPBW-UHFFFAOYSA-N ethenyl 4-(5-methoxynaphthalen-1-yl)oxypiperidine-1-carboxylate Chemical compound C1=CC=C2C(OC)=CC=CC2=C1OC1CCN(C(=O)OC=C)CC1 JBZVNNUFGSXPBW-UHFFFAOYSA-N 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000000505 pernicious effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- YDRLUQURTTVLIK-UHFFFAOYSA-N propanal;hydrochloride Chemical compound Cl.CCC=O YDRLUQURTTVLIK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000037047 psychomotor activity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000008096 xylene Substances 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (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)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6430579A | 1979-08-06 | 1979-08-06 | |
| US64,305 | 1979-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1123440A true CA1123440A (en) | 1982-05-11 |
Family
ID=22055014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA355,369A Expired CA1123440A (en) | 1979-08-06 | 1980-07-03 | 4-(naphthalenyloxy)piperidine derivatives |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5626875A (ja) |
| AU (1) | AU534398B2 (ja) |
| BE (1) | BE884581A (ja) |
| CA (1) | CA1123440A (ja) |
| CH (1) | CH644364A5 (ja) |
| DE (1) | DE3028064A1 (ja) |
| DK (1) | DK150477C (ja) |
| ES (1) | ES493591A0 (ja) |
| FR (1) | FR2463129A1 (ja) |
| GB (1) | GB2056447B (ja) |
| IE (1) | IE49998B1 (ja) |
| IL (1) | IL60593A (ja) |
| IT (1) | IT1146966B (ja) |
| NL (1) | NL8004147A (ja) |
| NO (1) | NO153726C (ja) |
| NZ (1) | NZ194248A (ja) |
| SE (1) | SE448728B (ja) |
| ZA (1) | ZA804112B (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508445A1 (fr) * | 1981-06-29 | 1982-12-31 | Sori Soc Rech Ind | Nouveaux derives de benzoyl-phenyl-piperidine, leur procede de preparation et leur application, notamment en therapeutique |
| EP0077427B1 (fr) * | 1981-10-15 | 1985-05-22 | Synthelabo | Dérivés de pipéridine, leur procédé de préparation et leur application en thérapeutique |
| GB8321157D0 (en) * | 1983-08-05 | 1983-09-07 | Fordonal Sa | Piperidine derivatives |
| JP2751346B2 (ja) * | 1989-03-15 | 1998-05-18 | ミノルタ株式会社 | プリンタ |
| WO2010055006A1 (en) * | 2008-11-17 | 2010-05-20 | F. Hoffmann-La Roche Ag | Naphthylacetic acids used as crth2 antagonists or partial agonists |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB895309A (en) * | 1959-11-18 | 1962-05-02 | Res Lab Dr C Janssen Nv | Pyrrolidine and piperidine derivatives |
| BE637978A (ja) * | 1963-02-15 | |||
| US3743645A (en) * | 1970-10-19 | 1973-07-03 | Robins Co Inc A H | 1-substituted-4-phenoxypiperidines |
| ZA717147B (en) * | 1970-11-27 | 1972-07-26 | Richardson Merrell Inc | 4-(4-(alpha-hydroxybenzyl)piperidino)-4'-fluorobutyrophenone derivatives |
| US3806526A (en) * | 1972-01-28 | 1974-04-23 | Richardson Merrell Inc | 1-aroylalkyl-4-diphenylmethyl piperidines |
| SE7409245L (ja) * | 1973-07-19 | 1975-01-20 | Robins Co Inc A H | |
| DE2718405A1 (de) * | 1977-04-26 | 1978-11-02 | Boehringer Sohn Ingelheim | Neue n- eckige klammer auf 1-(3-benzoylpropyl)-4-piperidyl eckige klammer zu -sulfonsaeureamide und verfahren zu deren herstellung |
| US4134982A (en) * | 1977-09-26 | 1979-01-16 | Warner-Lambert Company | Antipsychotic 1-[4,4-Bis(4-fluorophenyl) butyl]-4-phenoxy-1,2,3,6-tetrahydropyridines |
-
1980
- 1980-07-01 IE IE1382/80A patent/IE49998B1/en not_active IP Right Cessation
- 1980-07-03 CA CA355,369A patent/CA1123440A/en not_active Expired
- 1980-07-04 NZ NZ194248A patent/NZ194248A/en unknown
- 1980-07-08 ZA ZA00804112A patent/ZA804112B/xx unknown
- 1980-07-14 AU AU60394/80A patent/AU534398B2/en not_active Ceased
- 1980-07-15 IL IL60593A patent/IL60593A/xx unknown
- 1980-07-18 NL NL8004147A patent/NL8004147A/nl not_active Application Discontinuation
- 1980-07-22 ES ES493591A patent/ES493591A0/es active Granted
- 1980-07-24 DE DE19803028064 patent/DE3028064A1/de active Granted
- 1980-07-31 BE BE0/201611A patent/BE884581A/fr not_active IP Right Cessation
- 1980-07-31 SE SE8005493A patent/SE448728B/sv not_active IP Right Cessation
- 1980-07-31 IT IT49394/80A patent/IT1146966B/it active
- 1980-08-01 GB GB8025192A patent/GB2056447B/en not_active Expired
- 1980-08-01 JP JP10521180A patent/JPS5626875A/ja active Granted
- 1980-08-04 CH CH590380A patent/CH644364A5/de not_active IP Right Cessation
- 1980-08-05 DK DK337280A patent/DK150477C/da active
- 1980-08-05 NO NO802346A patent/NO153726C/no unknown
- 1980-08-05 FR FR8017290A patent/FR2463129A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2463129A1 (fr) | 1981-02-20 |
| NO153726B (no) | 1986-02-03 |
| IT8049394A0 (it) | 1980-07-31 |
| AU534398B2 (en) | 1984-01-26 |
| IE49998B1 (en) | 1986-01-22 |
| FR2463129B1 (ja) | 1983-04-22 |
| IL60593A (en) | 1984-03-30 |
| ES8105981A1 (es) | 1981-07-01 |
| DE3028064A1 (de) | 1981-02-26 |
| BE884581A (fr) | 1980-11-17 |
| ES493591A0 (es) | 1981-07-01 |
| SE8005493L (sv) | 1981-02-07 |
| IT1146966B (it) | 1986-11-19 |
| ZA804112B (en) | 1981-07-29 |
| NL8004147A (nl) | 1981-02-10 |
| JPS5626875A (en) | 1981-03-16 |
| JPS6341390B2 (ja) | 1988-08-17 |
| DK337280A (da) | 1981-02-07 |
| CH644364A5 (de) | 1984-07-31 |
| IE801382L (en) | 1981-02-06 |
| NZ194248A (en) | 1984-07-06 |
| NO153726C (no) | 1986-05-14 |
| IL60593A0 (en) | 1980-09-16 |
| GB2056447A (en) | 1981-03-18 |
| SE448728B (sv) | 1987-03-16 |
| DE3028064C2 (ja) | 1989-11-09 |
| NO802346L (no) | 1981-02-09 |
| GB2056447B (en) | 1983-07-06 |
| DK150477C (da) | 1987-10-12 |
| DK150477B (da) | 1987-03-09 |
| AU6039480A (en) | 1981-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19990511 |