NO851393L - Fremgangsmaate for fremstilling av n-aryl-n-(4-piperidinyl)amider. - Google Patents
Fremgangsmaate for fremstilling av n-aryl-n-(4-piperidinyl)amider.Info
- Publication number
- NO851393L NO851393L NO851393A NO851393A NO851393L NO 851393 L NO851393 L NO 851393L NO 851393 A NO851393 A NO 851393A NO 851393 A NO851393 A NO 851393A NO 851393 L NO851393 L NO 851393L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- piperidine
- ethyl
- phenyl
- methyl
- Prior art date
Links
- -1 4-PIPERIDINYL Chemical class 0.000 title claims description 87
- 238000000034 method Methods 0.000 title claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 73
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000004345 1-phenyl-2-propyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- WNCUHOHNHPGUFT-UHFFFAOYSA-N methyl 4-[acetyl(phenylmethoxy)amino]-1-benzylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CCN1CC1=CC=CC=C1 WNCUHOHNHPGUFT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- XTNILNPGGQFYHM-UHFFFAOYSA-N n-[4-(methoxymethyl)-1-(2-phenylethyl)piperidin-4-yl]-n-phenylmethoxyacetamide Chemical compound C1CC(COC)(N(OCC=2C=CC=CC=2)C(C)=O)CCN1CCC1=CC=CC=C1 XTNILNPGGQFYHM-UHFFFAOYSA-N 0.000 claims description 3
- VUCWMAJEUOWLEY-UHFFFAOYSA-N 1-$l^{1}-azanylpiperidine Chemical compound [N]N1CCCCC1 VUCWMAJEUOWLEY-UHFFFAOYSA-N 0.000 claims description 2
- JNMIKARGIXMLBD-UHFFFAOYSA-N methyl 4-[acetyl(phenylmethoxy)amino]-1-(2-phenylethyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CCN1CCC1=CC=CC=C1 JNMIKARGIXMLBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- LZKVXBQOOPUNCP-UHFFFAOYSA-N 2-methoxy-n-[3-methyl-1-(2-thiophen-2-ylethyl)piperidin-4-yl]-n-phenylpropanamide Chemical compound C=1C=CC=CC=1N(C(=O)C(C)OC)C(C(C1)C)CCN1CCC1=CC=CS1 LZKVXBQOOPUNCP-UHFFFAOYSA-N 0.000 claims 1
- JFUZJQRRXWYJQC-UHFFFAOYSA-N 2-methoxy-n-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide Chemical compound C=1C=CC=CC=1N(C(=O)C(C)OC)C(CC1)CCN1CCC1=CC=CC=C1 JFUZJQRRXWYJQC-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical class [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- CSGOHWXLCIIVGS-UHFFFAOYSA-N methyl 4-[acetyl(phenylmethoxy)amino]-1-(2-methylpropyl)piperidine-4-carboxylate Chemical compound C=1C=CC=CC=1CON(C(C)=O)C1(C(=O)OC)CCN(CC(C)C)CC1 CSGOHWXLCIIVGS-UHFFFAOYSA-N 0.000 claims 1
- IOCJQHBGDLGVIG-UHFFFAOYSA-N methyl 4-[acetyl(phenylmethoxy)amino]-1-(2-phenylpropyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CCN1CC(C)C1=CC=CC=C1 IOCJQHBGDLGVIG-UHFFFAOYSA-N 0.000 claims 1
- CJKGYRCNNXVNLT-UHFFFAOYSA-N methyl 4-[acetyl(phenylmethoxy)amino]-1-(2-thiophen-3-ylethyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CCN1CCC=1C=CSC=1 CJKGYRCNNXVNLT-UHFFFAOYSA-N 0.000 claims 1
- JWTRLWBMHRDSRJ-UHFFFAOYSA-N n-(2-fluorophenyl)-2-methoxy-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide Chemical compound C=1C=CC=C(F)C=1N(C(=O)C(C)OC)C(CC1)CCN1CCC1=CC=CC=C1 JWTRLWBMHRDSRJ-UHFFFAOYSA-N 0.000 claims 1
- POYWHJHIFVHORY-UHFFFAOYSA-N n-(2-fluorophenyl)-n-[1-[2-(2-fluorophenyl)ethyl]piperidin-4-yl]-2-methoxyacetamide Chemical compound C=1C=CC=C(F)C=1N(C(=O)COC)C(CC1)CCN1CCC1=CC=CC=C1F POYWHJHIFVHORY-UHFFFAOYSA-N 0.000 claims 1
- IPWHTDIAEVBZDE-WZONZLPQSA-N n-[(2-fluorophenyl)methoxy]-n-[(3r,4r)-3-methyl-1-(2-phenylethyl)piperidin-4-yl]acetamide Chemical compound C([C@H]([C@@H](CC1)N(OCC=2C(=CC=CC=2)F)C(C)=O)C)N1CCC1=CC=CC=C1 IPWHTDIAEVBZDE-WZONZLPQSA-N 0.000 claims 1
- LJZIXEVAZDYXSC-IIBYNOLFSA-N n-[(2-fluorophenyl)methoxy]-n-[(3r,4r)-3-methyl-1-(2-thiophen-2-ylethyl)piperidin-4-yl]acetamide Chemical compound C([C@H]([C@@H](CC1)N(OCC=2C(=CC=CC=2)F)C(C)=O)C)N1CCC1=CC=CS1 LJZIXEVAZDYXSC-IIBYNOLFSA-N 0.000 claims 1
- WDHJJVZSTPITDP-UHFFFAOYSA-N n-[(2-fluorophenyl)methoxy]-n-[1-(2-phenylethyl)piperidin-4-yl]acetamide Chemical compound C1CN(CCC=2C=CC=CC=2)CCC1N(C(=O)C)OCC1=CC=CC=C1F WDHJJVZSTPITDP-UHFFFAOYSA-N 0.000 claims 1
- AZMMNTOPOHXWQL-UHFFFAOYSA-N n-[(2-fluorophenyl)methoxy]-n-[1-(2-thiophen-3-ylethyl)piperidin-4-yl]acetamide Chemical compound C1CN(CCC2=CSC=C2)CCC1N(C(=O)C)OCC1=CC=CC=C1F AZMMNTOPOHXWQL-UHFFFAOYSA-N 0.000 claims 1
- IPWHTDIAEVBZDE-UHFFFAOYSA-N n-[(2-fluorophenyl)methoxy]-n-[3-methyl-1-(2-phenylethyl)piperidin-4-yl]acetamide Chemical compound C1CC(N(OCC=2C(=CC=CC=2)F)C(C)=O)C(C)CN1CCC1=CC=CC=C1 IPWHTDIAEVBZDE-UHFFFAOYSA-N 0.000 claims 1
- LJZIXEVAZDYXSC-UHFFFAOYSA-N n-[(2-fluorophenyl)methoxy]-n-[3-methyl-1-(2-thiophen-2-ylethyl)piperidin-4-yl]acetamide Chemical compound C1CC(N(OCC=2C(=CC=CC=2)F)C(C)=O)C(C)CN1CCC1=CC=CS1 LJZIXEVAZDYXSC-UHFFFAOYSA-N 0.000 claims 1
- MTSLEOSWKHPKIB-UHFFFAOYSA-N n-[(2-methoxyphenyl)methoxy]-n-[1-(1-phenylpropan-2-yl)piperidin-4-yl]acetamide Chemical compound COC1=CC=CC=C1CON(C(C)=O)C1CCN(C(C)CC=2C=CC=CC=2)CC1 MTSLEOSWKHPKIB-UHFFFAOYSA-N 0.000 claims 1
- LDFUCCZKUCBPFE-UHFFFAOYSA-N n-[1-(2-phenylethyl)piperidin-4-yl]-n-phenylmethoxyacetamide Chemical compound C1CN(CCC=2C=CC=CC=2)CCC1N(C(=O)C)OCC1=CC=CC=C1 LDFUCCZKUCBPFE-UHFFFAOYSA-N 0.000 claims 1
- IEIXJVOVJCWOFX-UHFFFAOYSA-N n-[3-methyl-1-(2-thiophen-2-ylethyl)piperidin-4-yl]-n-phenylmethoxyacetamide Chemical compound C1CC(N(OCC=2C=CC=CC=2)C(C)=O)C(C)CN1CCC1=CC=CS1 IEIXJVOVJCWOFX-UHFFFAOYSA-N 0.000 claims 1
- XCHSQTRMMVTFLJ-UHFFFAOYSA-N n-[4-(methoxymethyl)-1-(2-thiophen-2-ylethyl)piperidin-4-yl]-n-phenylmethoxyacetamide Chemical compound C1CC(COC)(N(OCC=2C=CC=CC=2)C(C)=O)CCN1CCC1=CC=CS1 XCHSQTRMMVTFLJ-UHFFFAOYSA-N 0.000 claims 1
- WYIMDZQCRFIEOJ-UHFFFAOYSA-N n-phenylmethoxy-n-[1-(2-thiophen-2-ylethyl)piperidin-4-yl]acetamide Chemical compound C1CN(CCC=2SC=CC=2)CCC1N(C(=O)C)OCC1=CC=CC=C1 WYIMDZQCRFIEOJ-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 31
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 21
- 239000003921 oil Substances 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 238000009835 boiling Methods 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
- 230000000202 analgesic effect Effects 0.000 description 10
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003643 water by type Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 150000004820 halides Chemical group 0.000 description 4
- VEIWYFRREFUNRC-UHFFFAOYSA-N hydron;piperidine;chloride Chemical compound [Cl-].C1CC[NH2+]CC1 VEIWYFRREFUNRC-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- ZCMDXDQUYIWEKB-UHFFFAOYSA-N n-phenyl-1-(2-phenylethyl)piperidin-4-amine Chemical compound C1CC(NC=2C=CC=CC=2)CCN1CCC1=CC=CC=C1 ZCMDXDQUYIWEKB-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- CKOJGMKAXXTOLV-UHFFFAOYSA-N 1-(2-chloroethyl)-4-ethyltetrazol-5-one Chemical compound CCN1N=NN(CCCl)C1=O CKOJGMKAXXTOLV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000036592 analgesia Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- BTODNVYAPWWHEA-UHFFFAOYSA-N n-[4-(methoxymethyl)piperidin-4-yl]-n-phenylmethoxyacetamide Chemical compound C=1C=CC=CC=1CON(C(C)=O)C1(COC)CCNCC1 BTODNVYAPWWHEA-UHFFFAOYSA-N 0.000 description 3
- YDJXNYNKKXZBMP-UHFFFAOYSA-N n-phenethyl-4-piperidinone Chemical compound C1CC(=O)CCN1CCC1=CC=CC=C1 YDJXNYNKKXZBMP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000008227 sterile water for injection Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WTOYUGZUPNQZHG-UHFFFAOYSA-N (4-anilino-1-benzylpiperidin-4-yl)methanol Chemical compound C1CC(CO)(NC=2C=CC=CC=2)CCN1CC1=CC=CC=C1 WTOYUGZUPNQZHG-UHFFFAOYSA-N 0.000 description 2
- OVQAJYCAXPHYNV-UHFFFAOYSA-N 1-benzyl-3-methylpiperidin-4-one Chemical compound C1CC(=O)C(C)CN1CC1=CC=CC=C1 OVQAJYCAXPHYNV-UHFFFAOYSA-N 0.000 description 2
- QBUUEBUUMUYSIY-UHFFFAOYSA-N 1-benzyl-4-(methoxymethyl)-n-phenylpiperidin-4-amine Chemical compound C1CC(COC)(NC=2C=CC=CC=2)CCN1CC1=CC=CC=C1 QBUUEBUUMUYSIY-UHFFFAOYSA-N 0.000 description 2
- GEENPCOOEPEUOQ-UHFFFAOYSA-N 1-benzyl-n-(2-fluorophenyl)-3-methylpiperidin-4-amine Chemical compound C1CC(NC=2C(=CC=CC=2)F)C(C)CN1CC1=CC=CC=C1 GEENPCOOEPEUOQ-UHFFFAOYSA-N 0.000 description 2
- FSXGJIFBTBJMHV-UHFFFAOYSA-N 1-benzyl-n-phenylpiperidin-4-amine Chemical compound C=1C=CC=CC=1CN(CC1)CCC1NC1=CC=CC=C1 FSXGJIFBTBJMHV-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- NVYOCAOZCSNIHR-UHFFFAOYSA-N 2-bromopropylbenzene Chemical compound CC(Br)CC1=CC=CC=C1 NVYOCAOZCSNIHR-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- NBEMORIANHKPTH-UHFFFAOYSA-N 2-methoxypropanoyl chloride Chemical compound COC(C)C(Cl)=O NBEMORIANHKPTH-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- UZOLQIGQMINAAE-UHFFFAOYSA-N methyl 1-but-2-ynyl-4-[2-methoxy-n-(2-methoxypropanoyl)anilino]piperidine-4-carboxylate Chemical compound C1CN(CC#CC)CCC1(C(=O)OC)N(C(=O)C(C)OC)C1=CC=CC=C1OC UZOLQIGQMINAAE-UHFFFAOYSA-N 0.000 description 1
- MRIKKFLITRMYGL-UHFFFAOYSA-N methyl 4-(n-(2-methoxyacetyl)anilino)-1-(2-phenylpropyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1C[NH+](CC(C)C=2C=CC=CC=2)CCC1(C(=O)OC)N(C(=O)COC)C1=CC=CC=C1.C1C[NH+](CC(C)C=2C=CC=CC=2)CCC1(C(=O)OC)N(C(=O)COC)C1=CC=CC=C1 MRIKKFLITRMYGL-UHFFFAOYSA-N 0.000 description 1
- OVBRZJBVPADOBF-UHFFFAOYSA-N methyl 4-[acetyl(phenylmethoxy)amino]-1-(2-phenylethyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CCC1=CC=CC=C1.C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CCC1=CC=CC=C1 OVBRZJBVPADOBF-UHFFFAOYSA-N 0.000 description 1
- KKVFQGMIXOGGAD-UHFFFAOYSA-N methyl 4-[acetyl(phenylmethoxy)amino]-1-(2-phenylpropyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CC(C)C1=CC=CC=C1.C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CC(C)C1=CC=CC=C1 KKVFQGMIXOGGAD-UHFFFAOYSA-N 0.000 description 1
- MJDNGJARHUOYKY-UHFFFAOYSA-N methyl 4-[acetyl(phenylmethoxy)amino]-1-(2-thiophen-2-ylethyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CCC1=CC=CS1.C1CC(C(=O)OC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CCC1=CC=CS1 MJDNGJARHUOYKY-UHFFFAOYSA-N 0.000 description 1
- QNWOBFNBFQVILJ-UHFFFAOYSA-N methyl 4-[acetyl-[(2-fluorophenyl)methoxy]amino]-1-(2-methylpropyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=C(F)C=1CON(C(C)=O)C1(C(=O)OC)CC[NH+](CC(C)C)CC1.C=1C=CC=C(F)C=1CON(C(C)=O)C1(C(=O)OC)CC[NH+](CC(C)C)CC1 QNWOBFNBFQVILJ-UHFFFAOYSA-N 0.000 description 1
- FNHMGUUQSCQZDK-UHFFFAOYSA-N methyl 4-[acetyl-[(2-fluorophenyl)methoxy]amino]-1-(2-phenylpropyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC[NH+]1CC(C)C1=CC=CC=C1.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC[NH+]1CC(C)C1=CC=CC=C1 FNHMGUUQSCQZDK-UHFFFAOYSA-N 0.000 description 1
- FFYBQZGGHMINIC-UHFFFAOYSA-N methyl 4-[acetyl-[(2-fluorophenyl)methoxy]amino]-1-(2-thiophen-2-ylethyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC[NH+]1CCC1=CC=CS1.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC[NH+]1CCC1=CC=CS1 FFYBQZGGHMINIC-UHFFFAOYSA-N 0.000 description 1
- ZSMAWEKESURLJK-UHFFFAOYSA-N methyl 4-[acetyl-[(2-fluorophenyl)methoxy]amino]-1-(2-thiophen-3-ylethyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC[NH+]1CCC=1C=CSC=1.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC[NH+]1CCC=1C=CSC=1 ZSMAWEKESURLJK-UHFFFAOYSA-N 0.000 description 1
- CTKNIENODJCGOL-UHFFFAOYSA-N methyl 4-[acetyl-[(2-fluorophenyl)methoxy]amino]-1-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC[NH+]1CCC=1SC=NC=1C.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC[NH+]1CCC=1SC=NC=1C CTKNIENODJCGOL-UHFFFAOYSA-N 0.000 description 1
- LQRLVAKXPAOWNH-UHFFFAOYSA-N methyl 4-[acetyl-[(2-fluorophenyl)methoxy]amino]piperidine-4-carboxylate Chemical compound C=1C=CC=C(F)C=1CON(C(C)=O)C1(C(=O)OC)CCNCC1 LQRLVAKXPAOWNH-UHFFFAOYSA-N 0.000 description 1
- KDGMYQCABNWNPJ-UHFFFAOYSA-N methyl 4-[acetyl-[(2-methoxyphenyl)methoxy]amino]-1-(2-methylpropyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=C(OC)C=1CON(C(C)=O)C1(C(=O)OC)CC[NH+](CC(C)C)CC1.C=1C=CC=C(OC)C=1CON(C(C)=O)C1(C(=O)OC)CC[NH+](CC(C)C)CC1 KDGMYQCABNWNPJ-UHFFFAOYSA-N 0.000 description 1
- PIOZKZSAPKPGJB-UHFFFAOYSA-N methyl 4-[acetyl-[(2-methoxyphenyl)methoxy]amino]-1-(2-thiophen-2-ylethyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)OC)C(C)=O)CC[NH+]1CCC1=CC=CS1.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)OC)C(C)=O)CC[NH+]1CCC1=CC=CS1 PIOZKZSAPKPGJB-UHFFFAOYSA-N 0.000 description 1
- RYCOUQPYBPNDCE-UHFFFAOYSA-N methyl 4-[acetyl-[(2-methoxyphenyl)methoxy]amino]-1-(2-thiophen-3-ylethyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)OC)C(C)=O)CC[NH+]1CCC=1C=CSC=1.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)OC)C(C)=O)CC[NH+]1CCC=1C=CSC=1 RYCOUQPYBPNDCE-UHFFFAOYSA-N 0.000 description 1
- GTEFHLIOGDDNJX-UHFFFAOYSA-N methyl 4-[acetyl-[(2-methoxyphenyl)methoxy]amino]-1-(3-methylbutyl)piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=C(OC)C=1CON(C(C)=O)C1(C(=O)OC)CC[NH+](CCC(C)C)CC1.C=1C=CC=C(OC)C=1CON(C(C)=O)C1(C(=O)OC)CC[NH+](CCC(C)C)CC1 GTEFHLIOGDDNJX-UHFFFAOYSA-N 0.000 description 1
- KRNFQPDWWBGKJE-UHFFFAOYSA-N methyl 4-[acetyl-[(2-methoxyphenyl)methoxy]amino]-1-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]piperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)OC)C(C)=O)CC[NH+]1CCC=1SC=NC=1C.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)OC)C(C)=O)CC[NH+]1CCC=1SC=NC=1C KRNFQPDWWBGKJE-UHFFFAOYSA-N 0.000 description 1
- CJYUKANDRIVFEN-UHFFFAOYSA-N methyl 4-[acetyl-[(2-methoxyphenyl)methoxy]amino]-1-benzylpiperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)OC)C(C)=O)CC[NH+]1CC1=CC=CC=C1.C1CC(C(=O)OC)(N(OCC=2C(=CC=CC=2)OC)C(C)=O)CC[NH+]1CC1=CC=CC=C1 CJYUKANDRIVFEN-UHFFFAOYSA-N 0.000 description 1
- JRRMASLAPHEXRG-UHFFFAOYSA-N methyl 4-[acetyl-[(2-methoxyphenyl)methoxy]amino]-1-pentan-2-ylpiperidin-1-ium-4-carboxylate;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1C[NH+](C(C)CCC)CCC1(C(=O)OC)N(C(C)=O)OCC1=CC=CC=C1OC.C1C[NH+](C(C)CCC)CCC1(C(=O)OC)N(C(C)=O)OCC1=CC=CC=C1OC JRRMASLAPHEXRG-UHFFFAOYSA-N 0.000 description 1
- SNQYRKKJUPYGJR-UHFFFAOYSA-N methyl 4-[n-(2-methoxypropanoyl)anilino]-1-prop-2-enylpiperidine-4-carboxylate Chemical compound C1CN(CC=C)CCC1(C(=O)OC)N(C(=O)C(C)OC)C1=CC=CC=C1 SNQYRKKJUPYGJR-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- MUDXJSHQOITSED-UHFFFAOYSA-N n-(1-benzyl-3-methylpiperidin-4-yl)-n-(2-fluorophenyl)-2-methoxypropanamide Chemical compound C=1C=CC=C(F)C=1N(C(=O)C(C)OC)C(C(C1)C)CCN1CC1=CC=CC=C1 MUDXJSHQOITSED-UHFFFAOYSA-N 0.000 description 1
- NVQMVTKBWMDQIO-UHFFFAOYSA-N n-(1-benzyl-3-methylpiperidin-4-yl)-n-[(2-fluorophenyl)methoxy]acetamide Chemical compound C1CC(N(OCC=2C(=CC=CC=2)F)C(C)=O)C(C)CN1CC1=CC=CC=C1 NVQMVTKBWMDQIO-UHFFFAOYSA-N 0.000 description 1
- ZPXXWDJRFPVOJJ-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-2-methoxy-n-phenylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N(C(=O)COC)C(CC1)CCN1CC1=CC=CC=C1 ZPXXWDJRFPVOJJ-UHFFFAOYSA-N 0.000 description 1
- DAOMKKHRVOXTMR-UHFFFAOYSA-N n-(1-heptyl-3-methylpiperidin-4-yl)-2-methoxy-n-phenylpropanamide Chemical compound CC1CN(CCCCCCC)CCC1N(C(=O)C(C)OC)C1=CC=CC=C1 DAOMKKHRVOXTMR-UHFFFAOYSA-N 0.000 description 1
- GUDCPDJEQAWBSZ-UHFFFAOYSA-N n-(2-chlorophenyl)-1-(2-phenylethyl)piperidin-4-amine Chemical compound ClC1=CC=CC=C1NC1CCN(CCC=2C=CC=CC=2)CC1 GUDCPDJEQAWBSZ-UHFFFAOYSA-N 0.000 description 1
- JIKKIUARYBEXPE-UHFFFAOYSA-N n-(2-fluorophenyl)-2-methoxy-n-[3-methyl-1-(2-thiophen-2-ylethyl)piperidin-4-yl]propanamide Chemical compound C=1C=CC=C(F)C=1N(C(=O)C(C)OC)C(C(C1)C)CCN1CCC1=CC=CS1 JIKKIUARYBEXPE-UHFFFAOYSA-N 0.000 description 1
- YLRKWEMXZJMIAW-UHFFFAOYSA-N n-[(2-chlorophenyl)methoxy]-n-[1-(2-phenylethyl)piperidin-1-ium-4-yl]acetamide;chloride Chemical compound [Cl-].C1C[NH+](CCC=2C=CC=CC=2)CCC1N(C(=O)C)OCC1=CC=CC=C1Cl YLRKWEMXZJMIAW-UHFFFAOYSA-N 0.000 description 1
- UBWGPXBNBFFHAU-UHFFFAOYSA-N n-[(2-fluorophenyl)methoxy]-n-(3-methylpiperidin-1-yl)acetamide Chemical compound C1C(C)CCCN1N(C(C)=O)OCC1=CC=CC=C1F UBWGPXBNBFFHAU-UHFFFAOYSA-N 0.000 description 1
- AGPYYMDSRICKRL-UHFFFAOYSA-N n-[(2-fluorophenyl)methoxy]-n-[1-(2-phenylethyl)piperidin-1-ium-4-yl]acetamide;chloride Chemical compound [Cl-].C1C[NH+](CCC=2C=CC=CC=2)CCC1N(C(=O)C)OCC1=CC=CC=C1F AGPYYMDSRICKRL-UHFFFAOYSA-N 0.000 description 1
- GYSDTHCEPBUAQK-UHFFFAOYSA-N n-[(4-fluorophenyl)methoxy]-n-piperidin-4-ylacetamide Chemical compound C1CNCCC1N(C(=O)C)OCC1=CC=C(F)C=C1 GYSDTHCEPBUAQK-UHFFFAOYSA-N 0.000 description 1
- XNRJXMWRESUWAW-UHFFFAOYSA-N n-[1-(2-phenylethyl)piperidin-1-ium-4-yl]-n-phenylmethoxyacetamide;chloride Chemical compound [Cl-].C1C[NH+](CCC=2C=CC=CC=2)CCC1N(C(=O)C)OCC1=CC=CC=C1 XNRJXMWRESUWAW-UHFFFAOYSA-N 0.000 description 1
- QUJBTXQDLSJUSL-UHFFFAOYSA-N n-[1-[2-(4-benzyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-phenylmethoxyacetamide Chemical compound C1CC(N(OCC=2C=CC=CC=2)C(C)=O)C(C)CN1CCN(C1=O)N=NN1CC1=CC=CC=C1 QUJBTXQDLSJUSL-UHFFFAOYSA-N 0.000 description 1
- HAEHRYBKXXDPMM-UHFFFAOYSA-N n-[1-[2-(4-cyclopentyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-phenylmethoxyacetamide Chemical compound C1CC(N(OCC=2C=CC=CC=2)C(C)=O)C(C)CN1CCN(C1=O)N=NN1C1CCCC1 HAEHRYBKXXDPMM-UHFFFAOYSA-N 0.000 description 1
- JYJIBDWYCGBHLI-UHFFFAOYSA-N n-[1-[2-(4-ethyl-5h-tetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-[(2-fluorophenyl)methoxy]acetamide Chemical compound N1=NN(CC)CN1CCN1CC(C)C(N(OCC=2C(=CC=CC=2)F)C(C)=O)CC1 JYJIBDWYCGBHLI-UHFFFAOYSA-N 0.000 description 1
- YJAKVAFDJXVUDW-UHFFFAOYSA-N n-[3-methyl-1-(2-thiophen-2-ylethyl)piperidin-1-ium-4-yl]-n-phenylmethoxyacetamide;chloride Chemical compound [Cl-].C1CC(N(OCC=2C=CC=CC=2)C(C)=O)C(C)C[NH+]1CCC1=CC=CS1 YJAKVAFDJXVUDW-UHFFFAOYSA-N 0.000 description 1
- CESWVEKGXCPQOD-UHFFFAOYSA-N n-[4-(methoxymethyl)-1-(2-phenylethyl)piperidin-1-ium-4-yl]-n-phenylmethoxyacetamide;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(COC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CCC1=CC=CC=C1.C1CC(COC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CCC1=CC=CC=C1 CESWVEKGXCPQOD-UHFFFAOYSA-N 0.000 description 1
- GGYSMKWLVQXFKG-UHFFFAOYSA-N n-[4-(methoxymethyl)-1-(2-thiophen-2-ylethyl)piperidin-1-ium-4-yl]-n-phenylmethoxyacetamide;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(COC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CCC1=CC=CS1.C1CC(COC)(N(OCC=2C=CC=CC=2)C(C)=O)CC[NH+]1CCC1=CC=CS1 GGYSMKWLVQXFKG-UHFFFAOYSA-N 0.000 description 1
- LKRMTUUCKBQGFO-UHFFFAOYSA-N n-phenylpiperidin-4-amine Chemical class C1CNCCC1NC1=CC=CC=C1 LKRMTUUCKBQGFO-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LKSWHQFYFLFHSK-UHFFFAOYSA-N oxalic acid;piperidine Chemical compound C1CC[NH2+]CC1.C1CC[NH2+]CC1.[O-]C(=O)C([O-])=O LKSWHQFYFLFHSK-UHFFFAOYSA-N 0.000 description 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000004634 pharmacological analysis method Methods 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 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
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
-
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US59876984A | 1984-04-09 | 1984-04-09 | |
US06/707,433 US4584303A (en) | 1984-04-09 | 1985-03-01 | N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
NO851393L true NO851393L (no) | 1985-10-10 |
Family
ID=27083145
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO851393A NO851393L (no) | 1984-04-09 | 1985-04-03 | Fremgangsmaate for fremstilling av n-aryl-n-(4-piperidinyl)amider. |
Country Status (12)
Country | Link |
---|---|
US (1) | US4584303A (fr) |
EP (1) | EP0160422B1 (fr) |
AU (1) | AU575924B2 (fr) |
CA (1) | CA1281719C (fr) |
DE (1) | DE3585100D1 (fr) |
DK (1) | DK154085A (fr) |
ES (2) | ES8609251A1 (fr) |
FI (1) | FI851337L (fr) |
GR (1) | GR850848B (fr) |
IL (1) | IL74726A (fr) |
NO (1) | NO851393L (fr) |
NZ (1) | NZ211599A (fr) |
Families Citing this family (59)
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FR2608602A1 (fr) * | 1986-12-23 | 1988-06-24 | Cerm Cent Europ Rech Mauvernay | Nouvelles 3-piperidineamines ou 3-azepineamines substituees, leur preparation et leurs applications en therapeutique |
US4916142A (en) * | 1987-02-02 | 1990-04-10 | Boc, Inc. | N-heterocyclic-N-(4-piperidinyl)amides and pharmaceutical compositions and their use as analgesics |
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US4791112A (en) * | 1987-02-02 | 1988-12-13 | The Boc Group, Inc. | N-heterocyclic-N-(4-piperidyl)amides and pharmaceutical compositions and methods employing such compounds |
US4954506A (en) * | 1987-02-02 | 1990-09-04 | Boc, Inc. | N-heterocyclic-N-(4-piperidinyl)amides and pharmaceutical compositions and methods employing such compounds |
GB8708833D0 (en) * | 1987-04-13 | 1987-05-20 | Lilly S A E | Organic compounds |
US4849521A (en) * | 1987-11-02 | 1989-07-18 | Boc, Inc. | Stereoselective preparation of 3-substituted-4-piperidine compounds and derivatives |
USRE33495E (en) * | 1987-11-02 | 1990-12-18 | Boc, Inc. | Stereoselective preparation of 3-substituted-4-anilino-piperidine compounds and derivatives |
US5013742A (en) * | 1987-11-02 | 1991-05-07 | Boc, Inc. | 4-phenyl-4-N-(phenyl) amido piperidine derivatives and pharmaceutical compositions and method employing such compounds |
US4791121A (en) * | 1987-11-02 | 1988-12-13 | The Boc Group, Inc. | 4-phenyl-4-(N-(phenyl)amido) piperidine derivatives and pharmaceutical compositions and method employing such compounds |
US4921864A (en) * | 1987-11-02 | 1990-05-01 | Boc, Inc. | 4-Phenyl-4-(N-(phenyl)amido) piperidine derivatives and pharmaceutical compositions and method employing such compounds |
US4791120A (en) * | 1987-12-31 | 1988-12-13 | The Boc Group, Inc. | 4-heteropentacyclic-4-[N-(phenyl)amino] piperidine derivatives and pharmaceutical compositions and method employing such compounds |
EP0328830B1 (fr) * | 1987-12-31 | 1994-06-01 | Ohmeda Pharmaceutical Products Division Inc. | Dérivés de 4-N-(phényl)amido pipéridine-4-hétéropentacyclique |
US4831192A (en) * | 1987-12-31 | 1989-05-16 | Boc, Inc. | Methods of preparing 4-heteropentacyclic-4-(N-phenyl)amido) piperidine derivatives and intermediate compounds |
US4801615A (en) * | 1987-12-31 | 1989-01-31 | The Boc Group, Inc. | 4-heterohexacyclic-4-(N-(phenyl)amido) piperidine derivatives and pharmaceutical compositions and method employing such compounds |
US5019583A (en) * | 1989-02-15 | 1991-05-28 | Glaxo Inc. | N-phenyl-N-(4-piperidinyl)amides useful as analgesics |
US5145967A (en) * | 1989-04-20 | 1992-09-08 | Anaquest, Inc. | Method for preparing 4-alkoxyalkyl-4-phenylaminopiperdines and derivatives thereof |
KR900016129A (ko) * | 1989-04-20 | 1990-11-12 | 테리 아아르 커세트 | 4-알콕시알킬-4-아미노페닐피페리딘 및 그들의 유도체의 제조 방법 |
US5053411A (en) * | 1989-04-20 | 1991-10-01 | Anaquest, Inc. | N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds |
USRE34201E (en) * | 1989-04-20 | 1993-03-23 | Anaquest, Inc. | N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds |
US4994471A (en) * | 1989-05-12 | 1991-02-19 | Boc, Inc. | N-aryl-N-(1-substituted-3-alkoxy-4-piperidinyl)amides and pharmaceutical compositions and methods employing such compounds |
US4939161A (en) * | 1989-05-12 | 1990-07-03 | Boc, Inc. | Analgesic N-aryl-N-[1-substituted-3,5-dimethyl-4-piperidinyl]amides |
US5100903A (en) * | 1989-05-12 | 1992-03-31 | Anaquest, Inc. | N-aryl-n-(1-substituted-3-alkoxy-4-piperidinyl)amides and pharmaceutical compositions and methods employing such compounds |
IE903196A1 (en) * | 1989-09-05 | 1991-03-13 | Searle & Co | Substituted n-benzylpiperidine amides |
FR2662162B1 (fr) * | 1990-05-18 | 1995-01-20 | Adir | Nouveaux derives de l'amino piperidine, de l'amino pyrrolidine et de l'amino perhydroazepine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
US5114714A (en) * | 1990-11-29 | 1992-05-19 | Sepracor, Inc. | Methods of use and compositions of (r)-isoflurane and (r)-desflurane |
US5114715A (en) * | 1990-11-29 | 1992-05-19 | Sepracor Inc. | Methods of use and compositions of (s)-isoflurane and (s)-desflurane |
US5214148A (en) * | 1990-12-18 | 1993-05-25 | Glaxo Inc. | Analgesic N-phenyl-N-(3-OR1 -3-ME-4-piperidinyl)amides |
US5130321A (en) * | 1990-12-18 | 1992-07-14 | Glaxo Inc. | Analgesic n-phenyl-n-(3-or 1-3-me-4-piperidinyl)amides |
AU666040B2 (en) * | 1992-10-28 | 1996-01-25 | Bayer Aktiengesellschaft | Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives |
FR2705674B1 (fr) * | 1993-05-26 | 1996-01-05 | Smithkline Beecham Labo Pharma | Nouveaux composés et leur procédé de préparation et leur utilisation en tant que médicaments. |
WO1994027967A1 (fr) * | 1993-05-26 | 1994-12-08 | Smithkline Beecham Laboratoires Pharmaceutiques | Nouveaux composes |
GB9316863D0 (en) * | 1993-08-13 | 1993-09-29 | Glaxo Group Ltd | Chemical process |
KR19990037220A (ko) * | 1997-10-31 | 1999-05-25 | 타이도 나오카타 | 아릴아세트산 아미드 유도체 또는 그 염 및 이를 함유하는 의약 |
US6677332B1 (en) * | 1999-05-25 | 2004-01-13 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US7361666B2 (en) * | 1999-05-25 | 2008-04-22 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US6635661B2 (en) | 2000-05-25 | 2003-10-21 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US6693099B2 (en) * | 2000-10-17 | 2004-02-17 | The Procter & Gamble Company | Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance |
US6376514B1 (en) * | 2000-10-17 | 2002-04-23 | The Procter & Gamble Co. | Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof |
ES2319879T3 (es) * | 2001-10-09 | 2009-05-14 | Kyorin Pharmaceutical Co., Ltd. | 4-(2-furoil)aminopiperidinas novedosas, productos intermedios en la sintesis de las mismas, procedimiento para producir las mismas y uso medico de las mismas. |
EP1720874A4 (fr) * | 2004-02-24 | 2010-03-03 | Bioaxone Therapeutique Inc | Derives de piperidine substitues en position 4 |
JP2008519837A (ja) * | 2004-11-10 | 2008-06-12 | ベーリンガー インゲルハイム ケミカルズ インコーポレイテッド | フェンタニル中間体の生成方法 |
CN101511187B (zh) | 2005-09-23 | 2012-07-04 | 株式会社爱慕知科学 | 哌啶和哌嗪衍生物 |
WO2007061555A1 (fr) * | 2005-11-17 | 2007-05-31 | Mallinckrodt Inc. | Procede de synthetisation du remifentanil |
NZ570078A (en) | 2006-01-27 | 2011-10-28 | Ms Science Corp | Piperidine and piperazine derivatives |
WO2008066708A2 (fr) * | 2006-11-29 | 2008-06-05 | Mallinckrodt Inc. | Nouveau procédé de synthèse du remifentanil |
US20110046180A1 (en) * | 2007-12-19 | 2011-02-24 | Neurosearch A/S | N-aryl-n-piperidin-4-yl-propionamide derivatives and their use as opioid receptor ligands |
EP2234616A1 (fr) * | 2007-12-19 | 2010-10-06 | NeuroSearch A/S | Dérivés de n-aryl-n-pipéridin-4-yl-propionamide et leur utilisation en tant qu'inhibiteurs de la réabsorption des neurotransmetteurs monoamines |
US8946433B2 (en) | 2010-09-17 | 2015-02-03 | Mallinckrodt Llc | Process for the preparation of sufentanil base and related compounds |
CN102249986B (zh) * | 2011-02-28 | 2016-06-22 | 华东理工大学 | N-苯乙基-4-苯胺基哌啶的制备方法 |
US20130281702A1 (en) * | 2012-04-24 | 2013-10-24 | Jonathan P. Pease | Methods For Preparing Fentanyl And Fentanyl Intermediates |
CN105307667B (zh) | 2013-03-13 | 2019-04-19 | 哈佛大学的校长及成员们 | 钉合且缝合的多肽及其用途 |
US10857157B2 (en) | 2015-01-26 | 2020-12-08 | BioAxone BioSciences, Inc. | Treatment of cerebral cavernous malformations and cerebral aneurysms with rho kinase inhibitors |
US10106525B2 (en) | 2015-01-26 | 2018-10-23 | BioAxone BioSciences, Inc. | Rho kinase inhibitor BA-1049 (R) and active metabolites thereof |
US10149856B2 (en) | 2015-01-26 | 2018-12-11 | BioAxone BioSciences, Inc. | Treatment of cerebral cavernous malformations and cerebral aneurysms with rho kinase inhibitors |
EP3442960A1 (fr) * | 2016-04-12 | 2019-02-20 | Esteve Pharmaceuticals, S.A. | Dérivés d'arylamide ayant une activité multimodale contre la douleur |
WO2017178515A1 (fr) * | 2016-04-12 | 2017-10-19 | Laboratorios Del Dr. Esteve, S.A. | Dérivés de pipéridinylalkylamide ayant une activité multimodale contre la douleur |
US11198680B2 (en) | 2016-12-21 | 2021-12-14 | BioAxone BioSciences, Inc. | Rho kinase inhibitor BA-1049 (R) and active metabolites thereof |
US10537567B2 (en) | 2017-07-11 | 2020-01-21 | BioAxone BioSciences, Inc. | Kinase inhibitors for treatment of disease |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL135583C (fr) * | 1961-10-10 | |||
US3161637A (en) * | 1961-10-10 | 1964-12-15 | Res Lab Dr C Janssen N V | 1-(gamma-aroyl-propyl)-4-(nu-arylcarbonyl amino) piperidines and related compounds |
US3998834A (en) * | 1975-03-14 | 1976-12-21 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl)-n-phenylamides and -carbamates |
US4197303A (en) * | 1975-09-23 | 1980-04-08 | Janssen Pharmaceutica N.V. | N-Aryl-N-(1-L-4-piperidinyl)-arylacetamides |
US4196210A (en) * | 1975-09-23 | 1980-04-01 | Janssen Pharmaceutica N.V. | N-Aryl-N-(1-L-4-piperidinyl)-arylacetamides |
FR2361880A1 (fr) * | 1976-04-29 | 1978-03-17 | Science Union & Cie | Nouvelles 4-amino piperidines, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
CA1183847A (fr) * | 1981-10-01 | 1985-03-12 | Georges Van Daele | N-(3-hydroxy-4-piperidinyl)benzamide; derives |
WO2000025009A1 (fr) * | 1998-10-23 | 2000-05-04 | Hitachi, Ltd. | Equipement de generation d'energie de turbine a gaz et dispositif d'humidification d'air |
-
1985
- 1985-03-01 US US06/707,433 patent/US4584303A/en not_active Expired - Fee Related
- 1985-03-26 AU AU40393/85A patent/AU575924B2/en not_active Ceased
- 1985-03-26 IL IL74726A patent/IL74726A/xx unknown
- 1985-03-27 NZ NZ211599A patent/NZ211599A/xx unknown
- 1985-04-03 NO NO851393A patent/NO851393L/no unknown
- 1985-04-03 CA CA000478273A patent/CA1281719C/fr not_active Expired - Fee Related
- 1985-04-03 DK DK154085A patent/DK154085A/da not_active Application Discontinuation
- 1985-04-03 FI FI851337A patent/FI851337L/fi not_active Application Discontinuation
- 1985-04-04 EP EP85302401A patent/EP0160422B1/fr not_active Expired - Lifetime
- 1985-04-04 GR GR850848A patent/GR850848B/el unknown
- 1985-04-04 DE DE8585302401T patent/DE3585100D1/de not_active Expired - Lifetime
- 1985-04-08 ES ES542023A patent/ES8609251A1/es not_active Expired
-
1986
- 1986-02-27 ES ES552468A patent/ES8705387A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
EP0160422B1 (fr) | 1992-01-08 |
NZ211599A (en) | 1988-11-29 |
IL74726A (en) | 1989-08-15 |
AU575924B2 (en) | 1988-08-11 |
ES8609251A1 (es) | 1986-09-01 |
IL74726A0 (en) | 1985-06-30 |
EP0160422A1 (fr) | 1985-11-06 |
DE3585100D1 (de) | 1992-02-20 |
ES542023A0 (es) | 1986-09-01 |
GR850848B (fr) | 1985-07-05 |
US4584303A (en) | 1986-04-22 |
ES8705387A1 (es) | 1987-05-01 |
FI851337A0 (fi) | 1985-04-03 |
ES552468A0 (es) | 1987-05-01 |
DK154085D0 (da) | 1985-04-03 |
CA1281719C (fr) | 1991-03-19 |
AU4039385A (en) | 1986-01-16 |
FI851337L (fi) | 1985-10-10 |
DK154085A (da) | 1985-10-10 |
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