CA1142936A - 4-amino-1-(2-pyridyl)piperidine compounds - Google Patents
4-amino-1-(2-pyridyl)piperidine compoundsInfo
- Publication number
- CA1142936A CA1142936A CA000354142A CA354142A CA1142936A CA 1142936 A CA1142936 A CA 1142936A CA 000354142 A CA000354142 A CA 000354142A CA 354142 A CA354142 A CA 354142A CA 1142936 A CA1142936 A CA 1142936A
- Authority
- CA
- Canada
- Prior art keywords
- pyridyl
- piperidine
- amino
- group
- chloro
- 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
- CZINLSYKXBADTA-UHFFFAOYSA-N 1-pyridin-2-ylpiperidin-4-amine Chemical class C1CC(N)CCN1C1=CC=CC=N1 CZINLSYKXBADTA-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 10
- YLWUSMHZABTZGP-UHFFFAOYSA-N n-piperidin-4-ylacetamide Chemical compound CC(=O)NC1CCNCC1 YLWUSMHZABTZGP-UHFFFAOYSA-N 0.000 claims description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- WPVVMKYQOMJPIN-UHFFFAOYSA-N 1-(6-chloro-2-pyridinyl)-4-piperidinamine Chemical compound C1CC(N)CCN1C1=CC=CC(Cl)=N1 WPVVMKYQOMJPIN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 6
- QGIXHPDIJWYJAV-UHFFFAOYSA-N 1-(6-bromopyridin-2-yl)piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC(Br)=N1 QGIXHPDIJWYJAV-UHFFFAOYSA-N 0.000 claims description 5
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 claims description 5
- IMFINBLMVWTWQX-UHFFFAOYSA-N n-[1-(6-chloropyridin-2-yl)piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC=CC(Cl)=N1 IMFINBLMVWTWQX-UHFFFAOYSA-N 0.000 claims description 5
- BIJAWQUBRNHZGE-UHFFFAOYSA-N n-pyridin-4-ylacetamide Chemical compound CC(=O)NC1=CC=NC=C1 BIJAWQUBRNHZGE-UHFFFAOYSA-N 0.000 claims description 4
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 claims description 3
- 150000005749 2-halopyridines Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- MXKALRMOISVVET-UHFFFAOYSA-N n-[1-(6-bromopyridin-2-yl)piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC=CC(Br)=N1 MXKALRMOISVVET-UHFFFAOYSA-N 0.000 claims description 3
- SGLJQTKFRSTKLJ-UHFFFAOYSA-N 1-(6-bromopyridin-2-yl)piperidin-4-amine;hydrochloride Chemical compound Cl.C1CC(N)CCN1C1=CC=CC(Br)=N1 SGLJQTKFRSTKLJ-UHFFFAOYSA-N 0.000 claims 1
- FUMINTAAUJUVMP-UHFFFAOYSA-N 1-(6-chloropyridin-2-yl)piperidin-4-amine;hydron;chloride Chemical compound Cl.C1CC(N)CCN1C1=CC=CC(Cl)=N1 FUMINTAAUJUVMP-UHFFFAOYSA-N 0.000 claims 1
- 230000002891 anorexigenic effect Effects 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 239000002830 appetite depressant Substances 0.000 abstract description 14
- 230000009471 action Effects 0.000 abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 4
- 239000013067 intermediate product Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 235000011167 hydrochloric acid Nutrition 0.000 description 9
- 229960000443 hydrochloric acid Drugs 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000006742 locomotor activity Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229940076279 serotonin Drugs 0.000 description 7
- -1 succ-nates Chemical class 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 150000003053 piperidines Chemical class 0.000 description 6
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000002490 cerebral effect Effects 0.000 description 5
- 229960001582 fenfluramine Drugs 0.000 description 5
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical class NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 5
- 230000009291 secondary effect Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 235000012631 food intake Nutrition 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CJAWPFJGFFNXQI-UHFFFAOYSA-N 2-chloro-6-(1-piperazinyl)pyrazine Chemical compound ClC1=CN=CC(N2CCNCC2)=N1 CJAWPFJGFFNXQI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 101100014660 Rattus norvegicus Gimap8 gene Proteins 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960005141 piperazine Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- ARHQBUXDPYQGJV-UHFFFAOYSA-N 1-(6-phenylsulfanylpyridin-2-yl)piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC(SC=2C=CC=CC=2)=N1 ARHQBUXDPYQGJV-UHFFFAOYSA-N 0.000 description 1
- YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical class C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 1
- LEZZSPMYYQOQRD-UHFFFAOYSA-N 2,2,2-trifluoroethanolate Chemical compound [O-]CC(F)(F)F LEZZSPMYYQOQRD-UHFFFAOYSA-N 0.000 description 1
- MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 1
- XGABOYVUTVJYGR-UHFFFAOYSA-N 2-(6-phenoxypyridin-2-yl)piperidin-4-amine Chemical compound C1C(N)CCNC1C1=CC=CC(OC=2C=CC=CC=2)=N1 XGABOYVUTVJYGR-UHFFFAOYSA-N 0.000 description 1
- MZVSTDHRRYQFGI-UHFFFAOYSA-N 2-chloro-4-methylpyridine Chemical compound CC1=CC=NC(Cl)=C1 MZVSTDHRRYQFGI-UHFFFAOYSA-N 0.000 description 1
- GXZDYRYYNXYPMQ-UHFFFAOYSA-N 2-chloro-6-methylpyridine Chemical compound CC1=CC=CC(Cl)=N1 GXZDYRYYNXYPMQ-UHFFFAOYSA-N 0.000 description 1
- KVYNCXZSIHYSDF-UHFFFAOYSA-N 2-chloro-6-methylsulfanylpyridine Chemical compound CSC1=CC=CC(Cl)=N1 KVYNCXZSIHYSDF-UHFFFAOYSA-N 0.000 description 1
- FTBCXEHMCFPRRF-UHFFFAOYSA-N 2-chloro-6-phenoxypyridine Chemical compound ClC1=CC=CC(OC=2C=CC=CC=2)=N1 FTBCXEHMCFPRRF-UHFFFAOYSA-N 0.000 description 1
- JRPFESQQRLEKBN-UHFFFAOYSA-N 2-chloro-6-phenylsulfanylpyridine Chemical compound ClC1=CC=CC(SC=2C=CC=CC=2)=N1 JRPFESQQRLEKBN-UHFFFAOYSA-N 0.000 description 1
- HQUQTERWIXPUFP-UHFFFAOYSA-N 2-chloro-6-propan-2-ylsulfanylpyridine Chemical compound CC(C)SC1=CC=CC(Cl)=N1 HQUQTERWIXPUFP-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- 150000003928 4-aminopyridines Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000287680 Garcinia dulcis Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 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
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- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000006005 fluoroethoxy group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
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- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QBQQKHZEHKZMJF-NXUSYKNTSA-N mioe Chemical compound C=1([C@@H]2OC(=O)C[C@@H]3[C@@]2(C)CC[C@H]2C3=C[C@@H]3[C@@H](OC(=O)C(C)C)C(C)(C)[C@@H]([C@@]2(C)C3=O)CC(=O)OC)C=COC=1 QBQQKHZEHKZMJF-NXUSYKNTSA-N 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- CXEJLCGIRISACP-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)formamide Chemical compound C1CC(NC=O)CCN1CC1=CC=CC=C1 CXEJLCGIRISACP-UHFFFAOYSA-N 0.000 description 1
- PMTGTBYLXXKGLO-UHFFFAOYSA-N n-[1-(6-methylpyridin-2-yl)piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC=CC(C)=N1 PMTGTBYLXXKGLO-UHFFFAOYSA-N 0.000 description 1
- GRYSTXPEXZXOPG-UHFFFAOYSA-N n-[2-(6-phenoxypyridin-2-yl)piperidin-4-yl]acetamide Chemical compound C1C(NC(=O)C)CCNC1C1=CC=CC(OC=2C=CC=CC=2)=N1 GRYSTXPEXZXOPG-UHFFFAOYSA-N 0.000 description 1
- QQWXHHWNGQDRCX-UHFFFAOYSA-N n-piperidin-4-ylformamide Chemical compound O=CNC1CCNCC1 QQWXHHWNGQDRCX-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 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
- 239000006187 pill Substances 0.000 description 1
- 231100000316 potential neurotoxicity Toxicity 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical class CC(C)S KJRCEJOSASVSRA-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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 108010080511 serum sodium transport inhibitor Proteins 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Obesity (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Child & Adolescent Psychology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7915974A FR2459240A1 (fr) | 1979-06-21 | 1979-06-21 | Aminopiperidines anorexigenes, procede pour leur preparation, intermediaires dans ledit procede et medicaments qui les contiennent |
| FR79/15,974 | 1979-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1142936A true CA1142936A (en) | 1983-03-15 |
Family
ID=9226937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000354142A Expired CA1142936A (en) | 1979-06-21 | 1980-06-17 | 4-amino-1-(2-pyridyl)piperidine compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4409228A (enExample) |
| EP (2) | EP0021973B1 (enExample) |
| JP (1) | JPS5636481A (enExample) |
| AR (1) | AR229088A1 (enExample) |
| AT (1) | ATE4901T1 (enExample) |
| CA (1) | CA1142936A (enExample) |
| DE (1) | DE3061266D1 (enExample) |
| ES (1) | ES492484A0 (enExample) |
| FR (1) | FR2459240A1 (enExample) |
Families Citing this family (19)
| 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 |
| GB8710494D0 (en) * | 1987-05-02 | 1987-06-03 | Pfizer Ltd | Antiarrhythmic agents |
| FR2674435B1 (fr) * | 1991-03-27 | 1995-03-10 | Sanofi Elf | Utilisation de 4-amino-1-(2-pyridyl) piperidines pour la preparation d'agents psychotropes. |
| EP0506545B1 (fr) * | 1991-03-27 | 1998-12-30 | Sanofi | Utilisation de 4-amino-1-(2-pyridyl)pipéridines comme agonistes 5-HT3 pour le traitement et la prophylaxie des dysfonctionnements sérotoninergiques |
| FR2674752B1 (fr) * | 1991-09-03 | 1995-03-10 | Sanofi Elf | Utilisation de 4-amino-1-(2-pyridyl)piperidines pour la preparation de medicaments pour le traitement et la prophylaxie des etats decoulant d'un dysfonctionnement du systeme serotoninergique. |
| FR2681785B1 (fr) * | 1991-09-30 | 1995-05-24 | Sanofi Elf | Utilisation de 4-amino-1-(2-pyridyl)piperidines en tant qu'agents anticonvulsivants et antiepileptiques. |
| CN1052224C (zh) * | 1993-04-07 | 2000-05-10 | 大塚制药株式会社 | 哌啶衍生物、含有它的外周血管舒张剂及其应用 |
| US6632823B1 (en) * | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| KR100713572B1 (ko) * | 1999-05-21 | 2007-05-02 | 아보트 러보러터리즈 | 중추 신경계 제제로서 유용한 헤테로사이클릭 치환된 아미노아자사이클 및 이를 포함하는 약제학적 조성물 |
| BR0007229A (pt) | 1999-05-21 | 2002-09-10 | Abbott Lab | Aminoazaciclos heterocìclicos substituìdos úteis como agentes de sistema nervoso central |
| US6833370B1 (en) * | 1999-05-21 | 2004-12-21 | Abbott Laboratories | Heterocycle substituted aminoazacycles useful as central nervous system agents |
| AU782648B2 (en) * | 1999-11-23 | 2005-08-18 | Janssen Pharmaceutica N.V. | Use of 5HT3 agonists for relaxing the fundus |
| NZ520041A (en) * | 2000-01-20 | 2004-11-26 | Eisai Co Ltd | Novel piperidine compounds and drugs containing the same |
| TW200303201A (en) * | 2001-12-10 | 2003-09-01 | Bristol Myers Squibb Co | Synthesis of 4,5-dihydro-pyrazolo [3,4-c] pyrid-2-ones |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| PT2013211E (pt) | 2006-04-21 | 2012-06-21 | Novartis Ag | Derivados de purina para utilização como agonistas de receptores a2a de adenosina |
| CN102452978A (zh) * | 2010-11-01 | 2012-05-16 | 重庆康丁医药技术有限公司 | 2-氯-取代或未取代脂族烃氧基吡啶及其制备方法 |
| CN111050800B (zh) | 2017-06-28 | 2023-04-04 | 国立大学法人大阪大学 | 血清素3受体激动剂对疼痛的治疗 |
| TW202508584A (zh) | 2023-05-25 | 2025-03-01 | 日商丸石製藥股份有限公司 | 癌性疼痛預防或治療用組成物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE738495C (de) * | 1941-08-10 | 1943-08-18 | Kastel Tvornica Kemijsko Farma | Verfahren zur Darstellung von substituierten 4-Aminopiperidinen |
-
1979
- 1979-06-21 FR FR7915974A patent/FR2459240A1/fr active Granted
-
1980
- 1980-06-16 ES ES492484A patent/ES492484A0/es active Granted
- 1980-06-17 EP EP80400874A patent/EP0021973B1/fr not_active Expired
- 1980-06-17 DE DE8080400874T patent/DE3061266D1/de not_active Expired
- 1980-06-17 CA CA000354142A patent/CA1142936A/en not_active Expired
- 1980-06-17 AT AT81107653T patent/ATE4901T1/de not_active IP Right Cessation
- 1980-06-17 EP EP81107653A patent/EP0045980B1/fr not_active Expired
- 1980-06-18 AR AR281448A patent/AR229088A1/es active
- 1980-06-20 JP JP8300880A patent/JPS5636481A/ja active Pending
-
1981
- 1981-12-03 US US06/327,022 patent/US4409228A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3061266D1 (en) | 1983-01-13 |
| FR2459240B1 (enExample) | 1982-10-22 |
| JPS5636481A (en) | 1981-04-09 |
| ES8104274A1 (es) | 1981-04-16 |
| ATE4901T1 (de) | 1983-10-15 |
| EP0021973A3 (en) | 1981-04-29 |
| FR2459240A1 (fr) | 1981-01-09 |
| EP0045980B1 (fr) | 1983-10-05 |
| US4409228A (en) | 1983-10-11 |
| EP0045980A1 (fr) | 1982-02-17 |
| EP0021973A2 (fr) | 1981-01-07 |
| ES492484A0 (es) | 1981-04-16 |
| EP0021973B1 (fr) | 1982-12-08 |
| AR229088A1 (es) | 1983-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |