CA1077942A - 4-phenoxymethylpiperidine compounds - Google Patents
4-phenoxymethylpiperidine compoundsInfo
- Publication number
- CA1077942A CA1077942A CA264,608A CA264608A CA1077942A CA 1077942 A CA1077942 A CA 1077942A CA 264608 A CA264608 A CA 264608A CA 1077942 A CA1077942 A CA 1077942A
- Authority
- CA
- Canada
- Prior art keywords
- piperidine
- process according
- formula
- chemical equivalent
- benzoyl
- 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
- BREBKAKBNYXIOP-UHFFFAOYSA-N 4-(phenoxymethyl)piperidine Chemical class C1CNCCC1COC1=CC=CC=C1 BREBKAKBNYXIOP-UHFFFAOYSA-N 0.000 title claims description 7
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 150000007524 organic acids Chemical class 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 235000005985 organic acids Nutrition 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 64
- -1 N-substituted 4-phenoxymethyl-piperidine Chemical class 0.000 claims description 22
- 150000003053 piperidines Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 claims description 5
- VYBZUXRVMWVTEB-UHFFFAOYSA-N 4-(phenoxymethyl)pyridine Chemical compound C=1C=NC=CC=1COC1=CC=CC=C1 VYBZUXRVMWVTEB-UHFFFAOYSA-N 0.000 claims description 4
- SVJZXTDZALYYRB-UHFFFAOYSA-N 4-[(2-nitrophenoxy)methyl]piperidine Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1CCNCC1 SVJZXTDZALYYRB-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- CUALLDHALGTGAS-UHFFFAOYSA-N [4-(phenoxymethyl)piperidin-1-yl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)N(CC1)CCC1COC1=CC=CC=C1 CUALLDHALGTGAS-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- HEMZNKOBGSXYFU-UHFFFAOYSA-N 2-(phenoxymethyl)pyridine Chemical class C=1C=CC=NC=1COC1=CC=CC=C1 HEMZNKOBGSXYFU-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 23
- 230000003301 hydrolyzing effect Effects 0.000 claims 19
- FGIVWTSVLVUKOK-UHFFFAOYSA-N 4-[(2-bromophenoxy)methyl]piperidine Chemical compound BrC1=CC=CC=C1OCC1CCNCC1 FGIVWTSVLVUKOK-UHFFFAOYSA-N 0.000 claims 2
- MPNAGTVTENGADV-UHFFFAOYSA-N 4-[(2-butan-2-ylphenoxy)methyl]piperidine Chemical compound CCC(C)C1=CC=CC=C1OCC1CCNCC1 MPNAGTVTENGADV-UHFFFAOYSA-N 0.000 claims 2
- YEDQERJRGLCJKY-UHFFFAOYSA-N 4-[(2-chlorophenoxy)methyl]piperidine Chemical compound ClC1=CC=CC=C1OCC1CCNCC1 YEDQERJRGLCJKY-UHFFFAOYSA-N 0.000 claims 2
- SIWFDPQWVCNYFU-UHFFFAOYSA-N 4-[(2-ethylphenoxy)methyl]piperidine Chemical compound CCC1=CC=CC=C1OCC1CCNCC1 SIWFDPQWVCNYFU-UHFFFAOYSA-N 0.000 claims 2
- GTYCVCKSMFWBQA-UHFFFAOYSA-N 4-[(2-fluorophenoxy)methyl]piperidine Chemical compound FC1=CC=CC=C1OCC1CCNCC1 GTYCVCKSMFWBQA-UHFFFAOYSA-N 0.000 claims 2
- CCZZNPBXUZCPEZ-UHFFFAOYSA-N 4-[(2-methoxyphenoxy)methyl]piperidine Chemical compound COC1=CC=CC=C1OCC1CCNCC1 CCZZNPBXUZCPEZ-UHFFFAOYSA-N 0.000 claims 2
- PVLZQVJPOZTGMJ-UHFFFAOYSA-N 4-[(2-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC=C1OCC1CCNCC1 PVLZQVJPOZTGMJ-UHFFFAOYSA-N 0.000 claims 2
- PPHIYDGKKZEIPW-UHFFFAOYSA-N 4-[(2-propylphenoxy)methyl]piperidine Chemical compound CCCC1=CC=CC=C1OCC1CCNCC1 PPHIYDGKKZEIPW-UHFFFAOYSA-N 0.000 claims 2
- JRKWHWMRJYOIEA-UHFFFAOYSA-N 4-[(3-chlorophenoxy)methyl]piperidine Chemical compound ClC1=CC=CC(OCC2CCNCC2)=C1 JRKWHWMRJYOIEA-UHFFFAOYSA-N 0.000 claims 2
- BJWGYFBJEZCOEG-UHFFFAOYSA-N 4-[(3-methoxyphenoxy)methyl]piperidine Chemical compound COC1=CC=CC(OCC2CCNCC2)=C1 BJWGYFBJEZCOEG-UHFFFAOYSA-N 0.000 claims 2
- IGXCLKXDHNOUIB-UHFFFAOYSA-N 4-[(3-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC(OCC2CCNCC2)=C1 IGXCLKXDHNOUIB-UHFFFAOYSA-N 0.000 claims 2
- KWLNQJLKIFFYNF-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]piperidine Chemical compound C1=CC(Cl)=CC=C1OCC1CCNCC1 KWLNQJLKIFFYNF-UHFFFAOYSA-N 0.000 claims 2
- RERPCSOKGBHYNQ-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]piperidine Chemical compound C1=CC(F)=CC=C1OCC1CCNCC1 RERPCSOKGBHYNQ-UHFFFAOYSA-N 0.000 claims 2
- NPWGQYGFHRSCQA-UHFFFAOYSA-N 4-[(4-methoxyphenoxy)methyl]piperidine Chemical compound C1=CC(OC)=CC=C1OCC1CCNCC1 NPWGQYGFHRSCQA-UHFFFAOYSA-N 0.000 claims 2
- OIRBFUKKCSYAKX-UHFFFAOYSA-N 4-[(4-methylphenoxy)methyl]piperidine Chemical compound C1=CC(C)=CC=C1OCC1CCNCC1 OIRBFUKKCSYAKX-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- NCDLFYLLYQXPCS-UHFFFAOYSA-N 2-chloro-1-methylpiperidine Chemical compound CN1CCCCC1Cl NCDLFYLLYQXPCS-UHFFFAOYSA-N 0.000 claims 1
- XYROETVBSCXMHN-UHFFFAOYSA-N 4-[(2-butoxyphenoxy)methyl]piperidine Chemical compound CCCCOC1=CC=CC=C1OCC1CCNCC1 XYROETVBSCXMHN-UHFFFAOYSA-N 0.000 claims 1
- VUGZSFREUJIEKD-UHFFFAOYSA-N [4-[(2-bromophenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound BrC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 VUGZSFREUJIEKD-UHFFFAOYSA-N 0.000 claims 1
- SWWJXTIAMRSNNV-UHFFFAOYSA-N [4-[(2-butoxyphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound CCCCOC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 SWWJXTIAMRSNNV-UHFFFAOYSA-N 0.000 claims 1
- QBYCPKQCECYPPU-UHFFFAOYSA-N [4-[(2-chlorophenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound ClC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 QBYCPKQCECYPPU-UHFFFAOYSA-N 0.000 claims 1
- IAOBQPLNTFFTBW-UHFFFAOYSA-N [4-[(2-fluorophenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound FC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 IAOBQPLNTFFTBW-UHFFFAOYSA-N 0.000 claims 1
- MAUKUXPJECWUJB-UHFFFAOYSA-N [4-[(2-methoxyphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound COC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 MAUKUXPJECWUJB-UHFFFAOYSA-N 0.000 claims 1
- NFBDJOYWBOOPOE-UHFFFAOYSA-N [4-[(2-methylphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound CC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 NFBDJOYWBOOPOE-UHFFFAOYSA-N 0.000 claims 1
- OWHLJCWQOGDSAU-UHFFFAOYSA-N [4-[(3-chlorophenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound ClC1=CC=CC(OCC2CCN(CC2)C(=O)C=2C=CC=CC=2)=C1 OWHLJCWQOGDSAU-UHFFFAOYSA-N 0.000 claims 1
- CFZNOMYRGHNRFP-UHFFFAOYSA-N [4-[(3-methoxyphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound COC1=CC=CC(OCC2CCN(CC2)C(=O)C=2C=CC=CC=2)=C1 CFZNOMYRGHNRFP-UHFFFAOYSA-N 0.000 claims 1
- ZVHXZSKGXGHGFV-UHFFFAOYSA-N [4-[(3-methylphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound CC1=CC=CC(OCC2CCN(CC2)C(=O)C=2C=CC=CC=2)=C1 ZVHXZSKGXGHGFV-UHFFFAOYSA-N 0.000 claims 1
- ZLBWAYJUUJMTJC-UHFFFAOYSA-N [4-[(4-chlorophenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound C1=CC(Cl)=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 ZLBWAYJUUJMTJC-UHFFFAOYSA-N 0.000 claims 1
- GCTWOTYFZSCRIR-UHFFFAOYSA-N [4-[(4-fluorophenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound C1=CC(F)=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 GCTWOTYFZSCRIR-UHFFFAOYSA-N 0.000 claims 1
- JPVVUUOCLIJCDC-UHFFFAOYSA-N [4-[(4-methoxyphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound C1=CC(OC)=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 JPVVUUOCLIJCDC-UHFFFAOYSA-N 0.000 claims 1
- FXGPRZNHTZZKGI-UHFFFAOYSA-N [4-[(4-methylphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 FXGPRZNHTZZKGI-UHFFFAOYSA-N 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 238000007344 nucleophilic reaction Methods 0.000 claims 1
- PZOCACLFMYEZSG-UHFFFAOYSA-N phenyl-[4-[(2-propylphenoxy)methyl]piperidin-1-yl]methanone Chemical compound CCCC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 PZOCACLFMYEZSG-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 230000003266 anti-allergic effect Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XLHLVPVJPDGPBC-UHFFFAOYSA-N 4-(chloromethyl)piperidine;hydrochloride Chemical compound Cl.ClCC1CCNCC1 XLHLVPVJPDGPBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GUOZBMRFKXWUNK-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(phenoxymethyl)piperidine Chemical class C1CN(CCCCl)CCC1COC1=CC=CC=C1 GUOZBMRFKXWUNK-UHFFFAOYSA-N 0.000 description 1
- UTIGJVMEFKRSCS-UHFFFAOYSA-N 4-(chloromethyl)piperidine Chemical compound ClCC1CCNCC1 UTIGJVMEFKRSCS-UHFFFAOYSA-N 0.000 description 1
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
- XRWWXZPTHSCQPJ-UHFFFAOYSA-N 4-(phenoxymethyl)piperidine;hydrochloride Chemical compound [Cl-].C1C[NH2+]CCC1COC1=CC=CC=C1 XRWWXZPTHSCQPJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- NWOKXPKMKWWJAY-UHFFFAOYSA-N [4-(chloromethyl)piperidin-1-yl]-phenylmethanone Chemical compound C1CC(CCl)CCN1C(=O)C1=CC=CC=C1 NWOKXPKMKWWJAY-UHFFFAOYSA-N 0.000 description 1
- RLTIVBMLQJFUOB-UHFFFAOYSA-N [4-(hydroxymethyl)piperidin-1-yl]-phenylmethanone Chemical compound C1CC(CO)CCN1C(=O)C1=CC=CC=C1 RLTIVBMLQJFUOB-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- PFWWZGINJSDVGU-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1.C1CCNCC1 PFWWZGINJSDVGU-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 1
- NKBJHERHVXOEIR-UHFFFAOYSA-N pyridin-4-ylmethanol;hydrochloride Chemical compound Cl.OCC1=CC=NC=C1 NKBJHERHVXOEIR-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752549999 DE2549999A1 (de) | 1975-11-07 | 1975-11-07 | Piperidin-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077942A true CA1077942A (en) | 1980-05-20 |
Family
ID=5961166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,608A Expired CA1077942A (en) | 1975-11-07 | 1976-10-28 | 4-phenoxymethylpiperidine compounds |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4243807A (en, 2012) |
| JP (1) | JPS6055509B2 (en, 2012) |
| AT (1) | AT352726B (en, 2012) |
| BE (1) | BE847973A (en, 2012) |
| CA (1) | CA1077942A (en, 2012) |
| CH (3) | CH624102A5 (en, 2012) |
| DD (1) | DD126942A5 (en, 2012) |
| DE (1) | DE2549999A1 (en, 2012) |
| DK (1) | DK494876A (en, 2012) |
| FI (1) | FI763148A7 (en, 2012) |
| FR (1) | FR2330678A1 (en, 2012) |
| GB (1) | GB1502050A (en, 2012) |
| HU (1) | HU171237B (en, 2012) |
| IE (1) | IE43866B1 (en, 2012) |
| IT (1) | IT1063618B (en, 2012) |
| LU (1) | LU76141A1 (en, 2012) |
| NL (1) | NL7612286A (en, 2012) |
| SE (1) | SE7612234L (en, 2012) |
| SU (3) | SU633473A3 (en, 2012) |
| ZA (1) | ZA766381B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6100285A (en) | 1995-06-07 | 2000-08-08 | Emisphere Technologies, Inc. | Method of solubilizing itraconazole |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
| US4556664A (en) * | 1984-03-13 | 1985-12-03 | Gunnar A. K. Aberg | Method and composition for the treatment of cardiac arrhythmias |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| US5231184A (en) * | 1987-11-23 | 1993-07-27 | Janssen Pharmaceutica N.V. | Pridazinamine derivatives |
| US4822778A (en) * | 1988-01-19 | 1989-04-18 | Gunnar Aberg | Membrane stabilizing phenoxy-piperidine compounds and pharmaceutical compositions employing such compounds |
| US5109002A (en) * | 1989-09-08 | 1992-04-28 | Du Pont Merck Pharmaceutical Company | Antipsychotic 1-cycloalkylpiperidines |
| IL99537A (en) * | 1990-09-27 | 1995-11-27 | Merck & Co Inc | Fibrinogen receptor antagonists and pharmaceutical compositions containing them |
| US5264420A (en) * | 1990-09-27 | 1993-11-23 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
| FR2667317B1 (fr) * | 1990-10-02 | 1992-12-04 | Synthelabo | Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique. |
| US5321034A (en) * | 1991-05-07 | 1994-06-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| FI934894A0 (fi) * | 1991-05-07 | 1993-11-05 | Merck & Co Inc | Fibrinogenreceptorantagonister |
| US5416099A (en) * | 1991-10-29 | 1995-05-16 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5272158A (en) * | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5389631A (en) * | 1991-10-29 | 1995-02-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| JPH08502484A (ja) * | 1992-10-14 | 1996-03-19 | メルク エンド カンパニー インコーポレーテッド | フィブリノゲンリセプタ拮抗剤 |
| US5358956A (en) * | 1992-10-14 | 1994-10-25 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5648368A (en) * | 1992-12-01 | 1997-07-15 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5441952A (en) * | 1993-04-05 | 1995-08-15 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5334596A (en) * | 1993-05-11 | 1994-08-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5397791A (en) * | 1993-08-09 | 1995-03-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5821241A (en) * | 1994-02-22 | 1998-10-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5719144A (en) * | 1995-02-22 | 1998-02-17 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| DE69615063T2 (de) * | 1995-09-28 | 2002-04-25 | Kaken Pharmaceutical Co., Ltd. | Verfahren zur herstellung von 4-methylen piperidinen |
| US5789421A (en) * | 1995-10-26 | 1998-08-04 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5780480A (en) * | 1996-02-28 | 1998-07-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5889023A (en) * | 1996-05-10 | 1999-03-30 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5981584A (en) * | 1997-02-06 | 1999-11-09 | Merck & Co., Inc. | Fibrinogen receptor antagonist prodrugs |
| WO2010011811A2 (en) | 2008-07-24 | 2010-01-28 | Theravance, Inc. | 3-(phenoxyphenylmethyl)pyrrolidine compounds |
| SI2358674T1 (sl) | 2008-11-14 | 2013-04-30 | Theravance, Inc. | Postopek za pripravo 4-(2-(2-fluorofenoksimetil)fenil)piperidinskih spojin |
| US20100267743A1 (en) * | 2009-04-15 | 2010-10-21 | Stangeland Eric L | 3-(phenoxypyrrolidin-3-yl-methyl)heteroaryl, 3-(phenylpyrrolidin-3-ylmethoxy)heteroaryl, and 3-(heteroarylpyrrolidin-3-ylmethoxy)heteroaryl compounds |
| AU2010273645B2 (en) | 2009-07-13 | 2014-12-04 | Theravance Biopharma R&D Ip, Llc | 3-phenoxymethylpyrrolidine compounds |
| US8273786B2 (en) * | 2009-07-21 | 2012-09-25 | Theravance, Inc. | 3-phenoxymethylpyrrolidine compounds |
| EP2523945A1 (en) | 2010-01-11 | 2012-11-21 | Theravance, Inc. | 1 - (2 - phenoxymethylphenyl) piperazine compounds as serotonin and norepinephrine reuptake inhibitors |
| JP5769348B2 (ja) * | 2010-03-22 | 2015-08-26 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | １−（２−フェノキシメチルヘテロアリール）ピペリジン化合物および１−（２−フェノキシメチルヘテロアリール）ピペラジン化合物 |
| EP2627630B1 (en) | 2010-10-11 | 2014-12-31 | Theravance Biopharma R&D IP, LLC | Serotonin reuptake inhibitors |
| WO2012075239A1 (en) | 2010-12-03 | 2012-06-07 | Theravance, Inc. | Serotonin reuptake inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268951A (en) * | 1969-06-12 | 1972-03-29 | Pfizer Ltd | Phenoxy-amines |
| DE2245061A1 (de) * | 1972-09-14 | 1974-03-28 | Boehringer Mannheim Gmbh | Derivate des adenins |
| DE2401254A1 (de) * | 1974-01-11 | 1975-11-27 | Boehringer Mannheim Gmbh | Neue derivate von n hoch 6-substituierten adeninen |
| DE2550000A1 (de) * | 1975-11-07 | 1977-05-12 | Boehringer Mannheim Gmbh | Neue purin-derivate und verfahren zu ihrer herstellung |
-
1975
- 1975-11-07 DE DE19752549999 patent/DE2549999A1/de active Granted
-
1976
- 1976-10-25 ZA ZA766381A patent/ZA766381B/xx unknown
- 1976-10-28 CA CA264,608A patent/CA1077942A/en not_active Expired
- 1976-10-29 IE IE2394/76A patent/IE43866B1/en unknown
- 1976-11-01 HU HU76BO00001639A patent/HU171237B/hu not_active IP Right Cessation
- 1976-11-01 US US05/737,518 patent/US4243807A/en not_active Expired - Lifetime
- 1976-11-02 SU SU762415648A patent/SU633473A3/ru active
- 1976-11-02 DK DK494876A patent/DK494876A/da not_active Application Discontinuation
- 1976-11-03 FI FI763148A patent/FI763148A7/fi not_active Application Discontinuation
- 1976-11-03 CH CH1385576A patent/CH624102A5/de not_active IP Right Cessation
- 1976-11-03 SE SE7612234A patent/SE7612234L/xx not_active Application Discontinuation
- 1976-11-04 DD DD195610A patent/DD126942A5/xx unknown
- 1976-11-04 BE BE172068A patent/BE847973A/xx not_active IP Right Cessation
- 1976-11-04 GB GB45916/76A patent/GB1502050A/en not_active Expired
- 1976-11-05 LU LU76141A patent/LU76141A1/xx unknown
- 1976-11-05 NL NL7612286A patent/NL7612286A/xx not_active Application Discontinuation
- 1976-11-05 IT IT29083/76A patent/IT1063618B/it active
- 1976-11-05 JP JP51133139A patent/JPS6055509B2/ja not_active Expired
- 1976-11-05 FR FR7633389A patent/FR2330678A1/fr active Granted
- 1976-11-05 AT AT823776A patent/AT352726B/de not_active IP Right Cessation
-
1977
- 1977-10-21 SU SU772534004A patent/SU867298A3/ru active
- 1977-10-21 SU SU772534003A patent/SU662009A3/ru active
-
1980
- 1980-10-03 CH CH742380A patent/CH625788A5/de not_active IP Right Cessation
- 1980-10-03 CH CH742480A patent/CH627166A5/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6100285A (en) | 1995-06-07 | 2000-08-08 | Emisphere Technologies, Inc. | Method of solubilizing itraconazole |
Also Published As
| Publication number | Publication date |
|---|---|
| CH627166A5 (en, 2012) | 1981-12-31 |
| IE43866L (en) | 1977-05-07 |
| DE2549999A1 (de) | 1977-05-12 |
| DE2549999C2 (en, 2012) | 1989-01-26 |
| ZA766381B (en) | 1977-10-26 |
| LU76141A1 (en, 2012) | 1977-05-18 |
| FI763148A7 (en, 2012) | 1977-05-08 |
| BE847973A (fr) | 1977-05-04 |
| SU867298A3 (ru) | 1981-09-23 |
| DK494876A (da) | 1977-05-08 |
| US4243807A (en) | 1981-01-06 |
| ATA823776A (de) | 1979-03-15 |
| AT352726B (de) | 1979-10-10 |
| JPS6055509B2 (ja) | 1985-12-05 |
| JPS5259163A (en) | 1977-05-16 |
| FR2330678A1 (fr) | 1977-06-03 |
| IT1063618B (it) | 1985-02-11 |
| CH625788A5 (en, 2012) | 1981-10-15 |
| CH624102A5 (en, 2012) | 1981-07-15 |
| FR2330678B1 (en, 2012) | 1980-11-07 |
| SU633473A3 (ru) | 1978-11-15 |
| SE7612234L (sv) | 1977-05-07 |
| NL7612286A (nl) | 1977-05-10 |
| SU662009A3 (ru) | 1979-05-05 |
| HU171237B (hu) | 1977-12-28 |
| IE43866B1 (en) | 1981-06-17 |
| GB1502050A (en) | 1978-02-22 |
| DD126942A5 (en, 2012) | 1977-08-24 |
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| MKEX | Expiry |