AP236A - "3-substituted piperdine derivatives, pharmaceutical compositions containing them and their use in therapy". - Google Patents
"3-substituted piperdine derivatives, pharmaceutical compositions containing them and their use in therapy". Download PDFInfo
- Publication number
- AP236A AP236A APAP/P/1991/000314A AP9100314A AP236A AP 236 A AP236 A AP 236A AP 9100314 A AP9100314 A AP 9100314A AP 236 A AP236 A AP 236A
- Authority
- AP
- ARIPO
- Prior art keywords
- compound
- pentylpiperidine
- phenyl
- compounds
- pharmaceutically acceptable
- Prior art date
Links
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims description 7
- 239000008194 pharmaceutical composition Chemical class 0.000 title claims description 5
- 238000002560 therapeutic procedure Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 143
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000011575 calcium Substances 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000009825 accumulation Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 210000004958 brain cell Anatomy 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
- WWFYUVKNMOFGSR-UHFFFAOYSA-N 1-pentyl-3-[(3-phenylphenoxy)methyl]piperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=CC(C=2C=CC=CC=2)=C1 WWFYUVKNMOFGSR-UHFFFAOYSA-N 0.000 claims 1
- PUZHRYBYNXAUEU-UHFFFAOYSA-N 1-pentyl-3-[(4-phenylmethoxyphenoxy)methyl]piperidine Chemical compound C1N(CCCCC)CCCC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 PUZHRYBYNXAUEU-UHFFFAOYSA-N 0.000 claims 1
- IPXAFMGFFGVCIN-UHFFFAOYSA-N 3,4-dichloro-n-[(1-pentylpiperidin-3-yl)methyl]aniline Chemical compound C1N(CCCCC)CCCC1CNC1=CC=C(Cl)C(Cl)=C1 IPXAFMGFFGVCIN-UHFFFAOYSA-N 0.000 claims 1
- WDOHUEFGFMHWDK-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yloxymethyl)-1-pentylpiperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=C(OCO2)C2=C1 WDOHUEFGFMHWDK-UHFFFAOYSA-N 0.000 claims 1
- USDSIEIKHQQHER-UHFFFAOYSA-N 3-[(2-benzylphenoxy)methyl]-1-pentylpiperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=CC=C1CC1=CC=CC=C1 USDSIEIKHQQHER-UHFFFAOYSA-N 0.000 claims 1
- QNGGMIAQIBEWLH-UHFFFAOYSA-N 3-[(4-benzylphenoxy)methyl]-1-pentylpiperidine Chemical compound C1N(CCCCC)CCCC1COC(C=C1)=CC=C1CC1=CC=CC=C1 QNGGMIAQIBEWLH-UHFFFAOYSA-N 0.000 claims 1
- ZBFJCZSXXOVMTG-UHFFFAOYSA-N 3-[(4-fluorophenoxy)methyl]-1-pentylpiperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=C(F)C=C1 ZBFJCZSXXOVMTG-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 229940125758 compound 15 Drugs 0.000 claims 1
- -1 3-substituted piperidine Chemical class 0.000 abstract description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 48
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 229940093499 ethyl acetate Drugs 0.000 description 31
- 235000019439 ethyl acetate Nutrition 0.000 description 31
- 239000007787 solid Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 23
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- LCDAPADGOWKBDM-UHFFFAOYSA-N (1-pentylpiperidin-3-yl)methanol Chemical compound CCCCCN1CCCC(CO)C1 LCDAPADGOWKBDM-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- 235000006408 oxalic acid Nutrition 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 3
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BJTTYMDZZCMDST-UHFFFAOYSA-N (1-propylpiperidin-3-yl)methanol Chemical compound CCCN1CCCC(CO)C1 BJTTYMDZZCMDST-UHFFFAOYSA-N 0.000 description 2
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 2
- QMKAORSYTLYVMI-UHFFFAOYSA-N 1-pentyl-3-[(4-phenylmethoxyphenoxy)methyl]piperidine;hydrochloride Chemical compound Cl.C1N(CCCCC)CCCC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 QMKAORSYTLYVMI-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- UDWLEOUINOCAJB-UHFFFAOYSA-N 3-[(2-benzylphenoxy)methyl]-1-pentylpiperidine;oxalic acid Chemical compound OC(=O)C(O)=O.C1N(CCCCC)CCCC1COC1=CC=CC=C1CC1=CC=CC=C1 UDWLEOUINOCAJB-UHFFFAOYSA-N 0.000 description 2
- FBESMXHISZHMKP-UHFFFAOYSA-N 3-[(4-benzylphenoxy)methyl]-1-pentylpiperidine;hydrochloride Chemical compound Cl.C1N(CCCCC)CCCC1COC(C=C1)=CC=C1CC1=CC=CC=C1 FBESMXHISZHMKP-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- 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
- C07D211/26—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 nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909017225A GB9017225D0 (en) | 1990-08-06 | 1990-08-06 | Compounds |
| GB909021852A GB9021852D0 (en) | 1990-10-08 | 1990-10-08 | Compounds |
| GB919107780A GB9107780D0 (en) | 1991-04-12 | 1991-04-12 | Compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9100314A0 AP9100314A0 (en) | 1991-10-31 |
| AP236A true AP236A (en) | 1993-02-24 |
Family
ID=27265217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1991/000314A AP236A (en) | 1990-08-06 | 1991-08-06 | "3-substituted piperdine derivatives, pharmaceutical compositions containing them and their use in therapy". |
Country Status (14)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5290789A (en) * | 1992-11-20 | 1994-03-01 | Sterling Wintrop Inc. | Penta and tetrasubstituted piperidines and compositions and method of treating psychosis |
| GB9226111D0 (en) * | 1992-12-15 | 1993-02-10 | Smithkline Beecham Plc | Madicaments |
| GB9314973D0 (en) * | 1993-07-20 | 1993-09-01 | Smithkline Beecham Plc | Medicaments |
| GB9319534D0 (en) * | 1993-09-22 | 1993-11-10 | Boots Co Plc | Therapeutic agents |
| WO1995024390A1 (en) * | 1994-03-11 | 1995-09-14 | Smithkline Beecham Plc | Novel phenyl(-alkyl/alkoxy)-1-aminoalkyl-substituted piperidines and pyrrolidines as calcium channel antagonists |
| US5770575A (en) * | 1994-03-16 | 1998-06-23 | Ortho Pharmaceutical Corporation | Nipecotic acid derivatives as antithrombotic compounds |
| GB9411052D0 (en) * | 1994-06-02 | 1994-07-20 | Smithkline Beecham Plc | Medicaments |
| GB9411045D0 (en) * | 1994-06-02 | 1994-07-20 | Smithkline Beecham Plc | Compounds and use |
| US5843983A (en) * | 1996-02-15 | 1998-12-01 | Sankyo Company, Limited | Diphenylethane compounds containing a saturated heterocyclic group, their preparation, and their therapeutic use |
| US6110937A (en) * | 1997-04-03 | 2000-08-29 | Syntex Usa, Inc. | Phenoxymethyl piperidine derivatives for the treatment of neuropathic pain |
| CA2232147A1 (en) * | 1997-04-03 | 1998-10-03 | F. Hoffmann-La Roche Ag | Phenoxymethyl piperidine derivatives |
| US6251919B1 (en) | 1998-02-27 | 2001-06-26 | Warner-Lambert | Heterocyclic substituted aniline calcium channel blockers |
| US6166052A (en) * | 1998-03-11 | 2000-12-26 | Warner-Lambert Company | Heteroaryl alkyl alpha substituted peptidylamine calcium channel blockers |
| WO2000009491A1 (en) * | 1998-08-12 | 2000-02-24 | Smithkline Beecham Corporation | Calcilytic compounds |
| WO2004002483A1 (en) * | 2002-06-27 | 2004-01-08 | Actelion Pharmaceuticals Ltd | Substituted 3- and 4- aminomethylpiperidines for use as beta-secretase in the treatment of alzheimer’s disease |
| HK1260897A1 (zh) | 2015-08-21 | 2019-12-27 | Portola Pharmaceuticals, Inc. | 使用四氢异喹啉小分子来结合并调节pcsk9的蛋白活性的组合物和方法 |
| US10568882B2 (en) | 2015-08-21 | 2020-02-25 | Srx Cardio, Llc | Phenylpiperazine proprotein convertase subtilisin/kexin type 9 (PCSK9) modulators and their use |
| WO2017034994A1 (en) | 2015-08-21 | 2017-03-02 | Portola Pharmaceuticals, Inc. | Composition and methods of use of novel phenylalanine small organic compounds to directly modulate pcsk9 protein activity |
| WO2017147328A1 (en) | 2016-02-23 | 2017-08-31 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0360685A1 (fr) * | 1988-09-23 | 1990-03-28 | Lipha, Lyonnaise Industrielle Pharmaceutique | "[(diarylméthoxy) alcoyl] - 1 pyrrolidines et piperidines, procédés de préparation et médicaments les contenant" |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2310762A1 (fr) * | 1975-05-16 | 1976-12-10 | Roussel Uclaf | Nouveaux derives n-substitues de la phenyl piperidine et leurs sels, procede de preparation et application a titre de medicaments |
| DE2950135A1 (de) * | 1979-12-13 | 1981-06-19 | Merck Patent Gmbh, 6100 Darmstadt | Basischer aether, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| FR2510112A1 (fr) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | Nouveaux derives du 2-oxo-pyrid-3-yl ou piperidin-3-yl indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
| ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
| CA1260474A (en) * | 1984-12-03 | 1989-09-26 | Raymond A. Stokbroekx | Benzoxazol- and benzothiazolamine derivatives |
| NZ219646A (en) * | 1986-03-27 | 1990-10-26 | Merck Sharp & Dohme | Oxadiazole derivatives of azacyclics for treating cns disorders |
| IL83275A (en) * | 1986-09-08 | 1994-02-27 | Novo Nordisk As | Substituted 1, 2, 4- oxadiazolyl piperidine compounds, their preparation and pharmaceutical compositions containing them |
| EP0307141B1 (en) * | 1987-09-10 | 1993-01-13 | MERCK SHARP & DOHME LTD. | Oxazoles and thiazoles for the treatment of senile dementia |
| DE3834860A1 (de) * | 1988-10-13 | 1990-04-19 | Basf Ag | Heterocyclisch substituierte alkoxycumarine, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
-
1991
- 1991-08-02 MX MX9100517A patent/MX9100517A/es unknown
- 1991-08-02 IE IE276091A patent/IE912760A1/en unknown
- 1991-08-04 IL IL99074A patent/IL99074A0/xx unknown
- 1991-08-05 NZ NZ239267A patent/NZ239267A/en unknown
- 1991-08-05 JP JP3513951A patent/JPH06500092A/ja active Pending
- 1991-08-05 CA CA002088490A patent/CA2088490A1/en not_active Abandoned
- 1991-08-05 TW TW080106122A patent/TW239860B/zh active
- 1991-08-05 MA MA22530A patent/MA22251A1/fr unknown
- 1991-08-05 EP EP91914530A patent/EP0542844A1/en not_active Withdrawn
- 1991-08-05 WO PCT/GB1991/001339 patent/WO1992002501A1/en not_active Application Discontinuation
- 1991-08-05 PT PT98575A patent/PT98575A/pt not_active Application Discontinuation
- 1991-08-05 CN CN91105944A patent/CN1062349A/zh active Pending
- 1991-08-05 AU AU83243/91A patent/AU649468B2/en not_active Ceased
- 1991-08-06 AP APAP/P/1991/000314A patent/AP236A/en active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0360685A1 (fr) * | 1988-09-23 | 1990-03-28 | Lipha, Lyonnaise Industrielle Pharmaceutique | "[(diarylméthoxy) alcoyl] - 1 pyrrolidines et piperidines, procédés de préparation et médicaments les contenant" |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ239267A (en) | 1994-05-26 |
| CN1062349A (zh) | 1992-07-01 |
| PT98575A (pt) | 1992-06-30 |
| AU649468B2 (en) | 1994-05-26 |
| JPH06500092A (ja) | 1994-01-06 |
| MX9100517A (es) | 1992-04-01 |
| IL99074A0 (en) | 1992-07-15 |
| TW239860B (enrdf_load_stackoverflow) | 1995-02-01 |
| IE912760A1 (en) | 1992-02-12 |
| AU8324391A (en) | 1992-03-02 |
| CA2088490A1 (en) | 1992-02-07 |
| MA22251A1 (fr) | 1992-04-01 |
| WO1992002501A1 (en) | 1992-02-20 |
| EP0542844A1 (en) | 1993-05-26 |
| AP9100314A0 (en) | 1991-10-31 |
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