HRP970394A2 - 4-hydroxy-piperidine derivatives - Google Patents

4-hydroxy-piperidine derivatives

Info

Publication number: HRP970394A2
Authority: HR; Croatia
Prior art keywords: hydroxy; benzyl; piperidin; compound; formula
Prior art date: 1996-07-19

Application number

HR97105366.5A

Other languages

English (en)

Croatian (hr)

Inventor

Rene Wyler

Original Assignee

Rene Wyler

Priority date (The priority date 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 date listed.)

1996-07-19

Filing date

1997-07-18

Publication date

1998-06-30

1997-07-18 Application filed by Rene Wyler filed Critical Rene Wyler

1998-06-30 Publication of HRP970394A2 publication Critical patent/HRP970394A2/hr

Links

HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 159
238000000034 method Methods 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 21
-1 hydroxy, amino Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
229910052740 iodine Inorganic materials 0.000 claims description 11
230000004770 neurodegeneration Effects 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims description 4
230000001154 acute effect Effects 0.000 claims description 4
230000001580 bacterial effect Effects 0.000 claims description 4
230000001684 chronic effect Effects 0.000 claims description 4
238000006264 debenzylation reaction Methods 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 4
VKMFDKYCIKEDMR-UHFFFAOYSA-N 1-[2-(4-hydroxyphenoxy)ethyl]-4-[(4-methylphenyl)methyl]-4-piperidinol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CCOC=2C=CC(O)=CC=2)CC1 VKMFDKYCIKEDMR-UHFFFAOYSA-N 0.000 claims description 3
QFAHXDADYUKETG-UHFFFAOYSA-N 2-(4-benzyl-4-hydroxypiperidin-1-yl)-n-(4-hydroxyphenyl)acetamide Chemical compound C1=CC(O)=CC=C1NC(=O)CN1CCC(O)(CC=2C=CC=CC=2)CC1 QFAHXDADYUKETG-UHFFFAOYSA-N 0.000 claims description 3
ANJWDFMPIFWMMV-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-1-[2-(4-hydroxyphenoxy)ethyl]piperidin-4-ol Chemical compound C1=CC(O)=CC=C1OCCN1CCC(O)(CC=2C=CC(F)=CC=2)CC1 ANJWDFMPIFWMMV-UHFFFAOYSA-N 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000035143 Bacterial infection Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
208000018737 Parkinson disease Diseases 0.000 claims description 3
208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
208000036142 Viral infection Diseases 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
208000022362 bacterial infectious disease Diseases 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
ZXOSRMWZINAXPW-UHFFFAOYSA-N n-[4-[2-[4-[(4-chlorophenyl)methyl]-4-hydroxypiperidin-1-yl]ethoxy]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1OCCN1CCC(O)(CC=2C=CC(Cl)=CC=2)CC1 ZXOSRMWZINAXPW-UHFFFAOYSA-N 0.000 claims description 3
BXUVBOLVQZCWIB-UHFFFAOYSA-N n-[4-[2-[4-hydroxy-4-[(4-methylphenyl)methyl]piperidin-1-yl]ethoxy]phenyl]methanesulfonamide Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CCOC=2C=CC(NS(C)(=O)=O)=CC=2)CC1 BXUVBOLVQZCWIB-UHFFFAOYSA-N 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
230000009385 viral infection Effects 0.000 claims description 3
JQXMOAFMNSZWEV-UHFFFAOYSA-N 1-[1-(4-hydroxyphenoxy)propan-2-yl]-4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1CC(O)(CC=2C=CC(C)=CC=2)CCN1C(C)COC1=CC=C(O)C=C1 JQXMOAFMNSZWEV-UHFFFAOYSA-N 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
238000003776 cleavage reaction Methods 0.000 claims description 2
150000002440 hydroxy compounds Chemical class 0.000 claims description 2
ANIIFBDXMQFPNH-UHFFFAOYSA-N n-[4-[2-[4-[(4-fluorophenyl)methyl]-4-hydroxypiperidin-1-yl]ethoxy]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1OCCN1CCC(O)(CC=2C=CC(F)=CC=2)CC1 ANIIFBDXMQFPNH-UHFFFAOYSA-N 0.000 claims description 2
RJQWWDXAWXCBCG-UHFFFAOYSA-N n-[4-[3-[4-[(4-fluorophenyl)methyl]-4-hydroxypiperidin-1-yl]propoxy]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1OCCCN1CCC(O)(CC=2C=CC(F)=CC=2)CC1 RJQWWDXAWXCBCG-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
230000007017 scission Effects 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
208000034189 Sclerosis Diseases 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 91
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 43
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 33
229910052938 sodium sulfate Inorganic materials 0.000 description 33
235000011152 sodium sulphate Nutrition 0.000 description 33
239000007787 solid Substances 0.000 description 32
239000012074 organic phase Substances 0.000 description 31
239000002904 solvent Substances 0.000 description 31
239000000741 silica gel Substances 0.000 description 30
229910002027 silica gel Inorganic materials 0.000 description 30
239000007832 Na2SO4 Substances 0.000 description 22
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
239000008346 aqueous phase Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000872 buffer Substances 0.000 description 15
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 14
238000001914 filtration Methods 0.000 description 14
238000007429 general method Methods 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
KJZBZOFESQSBCV-UHFFFAOYSA-N 4-benzylpiperidin-4-ol Chemical compound C=1C=CC=CC=1CC1(O)CCNCC1 KJZBZOFESQSBCV-UHFFFAOYSA-N 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
DGNFSJPAWJLVOH-UHFFFAOYSA-N 4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCNCC1 DGNFSJPAWJLVOH-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
210000000287 oocyte Anatomy 0.000 description 10
235000011181 potassium carbonates Nutrition 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 description 9
239000006260 foam Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
239000000556 agonist Substances 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
238000002844 melting Methods 0.000 description 7
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239000000126 substance Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
210000004556 brain Anatomy 0.000 description 6
RGIBXDHONMXTLI-UHFFFAOYSA-N chavicol Chemical compound OC1=CC=C(CC=C)C=C1 RGIBXDHONMXTLI-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
229940080818 propionamide Drugs 0.000 description 5
DFTIORCOZJOMGW-UHFFFAOYSA-N 4-(oxiran-2-ylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CC1OC1 DFTIORCOZJOMGW-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
SINSEJCKWXCUHO-UHFFFAOYSA-N 4-benzyl-1-(3-chloro-2-hydroxypropyl)piperidin-4-ol Chemical compound C1CN(CC(CCl)O)CCC1(O)CC1=CC=CC=C1 SINSEJCKWXCUHO-UHFFFAOYSA-N 0.000 description 4
102100029458 Glutamate receptor ionotropic, NMDA 2A Human genes 0.000 description 4
102100022630 Glutamate receptor ionotropic, NMDA 2B Human genes 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
238000009472 formulation Methods 0.000 description 4
VEXYZZJHZITYOM-UHFFFAOYSA-N n-(2-chloroethyl)-4-phenylmethoxybenzamide Chemical compound C1=CC(C(=O)NCCCl)=CC=C1OCC1=CC=CC=C1 VEXYZZJHZITYOM-UHFFFAOYSA-N 0.000 description 4
UPEQSEASYVYZEG-UHFFFAOYSA-N n-(3-chloropropyl)-4-phenylmethoxybenzamide Chemical compound C1=CC(C(=O)NCCCCl)=CC=C1OCC1=CC=CC=C1 UPEQSEASYVYZEG-UHFFFAOYSA-N 0.000 description 4
OQVGTWRPQINIPX-UHFFFAOYSA-N n-[2-[4-hydroxy-4-[(4-methylphenyl)methyl]piperidin-1-yl]ethyl]-4-phenylmethoxybenzamide Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CCNC(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CC1 OQVGTWRPQINIPX-UHFFFAOYSA-N 0.000 description 4
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BYDXZYUGDXYSJY-INIZCTEOSA-N (2r)-2-[(4-phenylmethoxyphenoxy)methyl]oxirane Chemical compound C([C@@H]1OC1)OC(C=C1)=CC=C1OCC1=CC=CC=C1 BYDXZYUGDXYSJY-INIZCTEOSA-N 0.000 description 3
QRBYCXUKWBWNQZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CCO)CC1 QRBYCXUKWBWNQZ-UHFFFAOYSA-N 0.000 description 3
DENKNRHTMNAEIS-UHFFFAOYSA-N 1-[3-(4-aminophenoxy)-2-hydroxypropyl]-4-benzylpiperidin-4-ol;hydrochloride Chemical compound Cl.C1=CC(N)=CC=C1OCC(O)CN1CCC(O)(CC=2C=CC=CC=2)CC1 DENKNRHTMNAEIS-UHFFFAOYSA-N 0.000 description 3
XNOZKVAOXOLUBS-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]piperidin-4-ol Chemical compound C=1C=C(F)C=CC=1CC1(O)CCNCC1 XNOZKVAOXOLUBS-UHFFFAOYSA-N 0.000 description 3
WQBYBTVKYHPNMO-RUZDIDTESA-N 4-benzyl-1-[(2r)-2-hydroxy-3-(4-phenylmethoxyphenoxy)propyl]piperidin-4-ol Chemical compound C([C@H](O)CN1CCC(O)(CC=2C=CC=CC=2)CC1)OC(C=C1)=CC=C1OCC1=CC=CC=C1 WQBYBTVKYHPNMO-RUZDIDTESA-N 0.000 description 3
WQBYBTVKYHPNMO-VWLOTQADSA-N 4-benzyl-1-[(2s)-2-hydroxy-3-(4-phenylmethoxyphenoxy)propyl]piperidin-4-ol Chemical compound C([C@@H](O)CN1CCC(O)(CC=2C=CC=CC=2)CC1)OC(C=C1)=CC=C1OCC1=CC=CC=C1 WQBYBTVKYHPNMO-VWLOTQADSA-N 0.000 description 3
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AQSCHALQLXXKKC-UHFFFAOYSA-N 4-phenylmethoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1=CC=CC=C1 AQSCHALQLXXKKC-UHFFFAOYSA-N 0.000 description 3
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PZFAFQSPTDMCQF-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-phenylmethoxybenzamide Chemical compound C1=CC(C(=O)NCCO)=CC=C1OCC1=CC=CC=C1 PZFAFQSPTDMCQF-UHFFFAOYSA-N 0.000 description 3
COHVKDCCHGYUHO-UHFFFAOYSA-N n-[2-(4-benzyl-4-hydroxypiperidin-1-yl)ethyl]-4-hydroxybenzamide Chemical compound C1=CC(O)=CC=C1C(=O)NCCN1CCC(O)(CC=2C=CC=CC=2)CC1 COHVKDCCHGYUHO-UHFFFAOYSA-N 0.000 description 3
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IDHSGBFGKYMOLF-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-1-[2-(4-phenylmethoxyphenoxy)ethyl]piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCC1(O)CC1=CC=C(F)C=C1 IDHSGBFGKYMOLF-UHFFFAOYSA-N 0.000 description 2
VUTQHUOIXZEINV-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]-1-[2-(4-phenylmethoxyphenoxy)ethyl]piperidin-4-ol Chemical compound C1=CC(OC)=CC=C1CC1(O)CCN(CCOC=2C=CC(OCC=3C=CC=CC=3)=CC=2)CC1 VUTQHUOIXZEINV-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61P25/00—Drugs for disorders of the nervous system
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links

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General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Neurosurgery (AREA)
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Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
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Medicinal Chemistry (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
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Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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HR97105366.5A 1996-07-19 1997-07-18 4-hydroxy-piperidine derivatives HRP970394A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP96111660		1996-07-19
EP97105366		1997-04-01

Publications (1)

Publication Number	Publication Date
HRP970394A2 true HRP970394A2 (en)	1998-06-30

Family

ID=26142078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR97105366.5A HRP970394A2 (en)	1996-07-19	1997-07-18	4-hydroxy-piperidine derivatives

Country Status (33)

Country	Link
US (1)	US5889026A (sh)
EP (1)	EP0824098B1 (sh)
JP (1)	JP3179050B2 (sh)
KR (1)	KR100235804B1 (sh)
CN (1)	CN1120154C (sh)
AR (2)	AR007897A1 (sh)
AT (1)	ATE207899T1 (sh)
AU (1)	AU719352B2 (sh)
BR (1)	BR9704031A (sh)
CA (1)	CA2210044C (sh)
CO (1)	CO4900064A1 (sh)
CZ (1)	CZ290898B6 (sh)
DE (1)	DE69707782T2 (sh)
DK (1)	DK0824098T3 (sh)
ES (1)	ES2164967T3 (sh)
HR (1)	HRP970394A2 (sh)
HU (1)	HUP9701194A3 (sh)
ID (1)	ID19632A (sh)
IL (1)	IL121299A (sh)
MA (1)	MA24274A1 (sh)
MX (1)	MX9705387A (sh)
NO (1)	NO308657B1 (sh)
NZ (1)	NZ328330A (sh)
PE (1)	PE86398A1 (sh)
PL (1)	PL321201A1 (sh)
PT (1)	PT824098E (sh)
RU (1)	RU2178412C2 (sh)
SG (1)	SG60085A1 (sh)
TR (1)	TR199700659A2 (sh)
TW (1)	TW498067B (sh)
UY (1)	UY24625A1 (sh)
YU (1)	YU30197A (sh)
ZA (1)	ZA976224B (sh)

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PL204628B1 (pl) *	1998-06-02	2010-01-29	Osi Pharmaceuticals	Pochodna pirolo[2,3d]pirymidyny, jej zastosowanie i sposoby wytwarzania tej pochodnej i preparaty farmaceutyczne
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EP1131290B1 (en)	1998-11-20	2008-02-20	F. Hoffmann-La Roche Ag	Piperidine ccr-3 receptor antagonists
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AU2002250256B2 (en) *	2001-03-08	2008-04-03	Emory University	pH-dependent NMDA receptor antagonists
KR100890676B1 (ko) *	2001-07-24	2009-03-26	리히데 게데온 베기에스제티 기아르 알티	신규한 카르복시산 아미드 화합물
CA2468673C (en) *	2001-11-30	2011-01-25	Osi Pharmaceuticals, Inc.	Compounds specific to adenosine a1 and a3 receptors and uses thereof
DE60235500D1 (de) *	2001-12-20	2010-04-08	Osi Pharm Inc	Selektive pyrimidin-a2b-antagonistenverbindungen, ihre synthese und verwendung
US6951884B2 (en) *	2002-06-12	2005-10-04	Hoffmann-La Roche Inc.	Fluorobenzamides and uses thereof
EP1666464A4 (en) *	2003-09-25	2008-12-10	Shionogi & Co	PIPERIDINE DERIVATIVE HAVING ANTAGONIST ACTIVITY OF THE NDMA RECEPTOR
EP1680127B1 (en) *	2003-10-23	2008-10-15	F. Hoffmann-La Roche Ag	Benzazepine derivatives as mao-b inhibitors
HUP0401522A2 (en) *	2004-07-29	2006-04-28	Richter Gedeon Vegyeszet	New 4-benzylidene-piperidine derivatives, pharmaceutical compositions containing the same and process for their preparation
US7485637B2 (en) *	2005-01-04	2009-02-03	Hoffmann-La Roche Inc.	Benzoyl-tetrahydropiperidine derivatives
KR20100045983A (ko) *	2007-06-29	2010-05-04	에모리 유니버시티	신경보호를 위한 ｎｍｄａ 수용체 길항물질
US7869022B2 (en)	2007-07-18	2011-01-11	Asml Netherlands B.V.	Inspection method and apparatus lithographic apparatus, lithographic processing cell, device manufacturing method and distance measuring system
WO2009137843A2 (en) *	2008-05-09	2009-11-12	Emory University	Nmda receptor antagonists for the treatment of neuropsychiatric disorders
US7874106B2 (en) *	2009-02-13	2011-01-25	Ykk Corporation Of America	Sill flashing and end dam assembly
ES2814178T3 (es) *	2009-10-19	2021-03-26	Amicus Therapeutics Inc	Nuevas composiciones para prevenir y/o tratar trastornos degenerativos del sistema nervioso central
CN102647905B (zh) *	2009-10-19	2015-09-09	阿米库斯治疗学公司	用于预防和/或治疗溶酶体贮积失调的新颖组合物
WO2016100823A1 (en)	2014-12-19	2016-06-23	The Broad Institute, Inc.	Dopamine d2 receptor ligands
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MX24433A (es) *	1990-02-06	1993-05-01	Pfizer	Derivados de 3-piperidino-1-cromanol y sus analogos y procedimiento para su preparacion
FR2672286B1 (fr) *	1991-01-31	1994-11-18	Synthelabo	Derives de 1-(4-chlorophenyl)-2-[4-(phenylmethyl)piperidin-1-yl]ethanol, leur preparation et leur application en therapeutique.
FR2681319B1 (fr) *	1991-09-12	1995-02-17	Synthelabo	Derives de 1-(phenoxyalkyl)piperidine, leur preparation et leur application en therapeutique.
TW281670B (sh) *	1993-09-02	1996-07-21	Hoffmann La Roche
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ZA9610736B (en) *	1995-12-22	1997-06-27	Warner Lambert Co	2-Substituted piperidine analogs and their use as subtypeselective nmda receptor antagonists
ZA9610745B (en) *	1995-12-22	1997-06-24	Warner Lambert Co	4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists

1997
- 1997-06-24 TW TW086108797A patent/TW498067B/zh active
- 1997-07-10 PT PT97111742T patent/PT824098E/pt unknown
- 1997-07-10 EP EP97111742A patent/EP0824098B1/en not_active Expired - Lifetime
- 1997-07-10 ES ES97111742T patent/ES2164967T3/es not_active Expired - Lifetime
- 1997-07-10 DE DE69707782T patent/DE69707782T2/de not_active Expired - Lifetime
- 1997-07-10 DK DK97111742T patent/DK0824098T3/da active
- 1997-07-10 AT AT97111742T patent/ATE207899T1/de active
- 1997-07-11 SG SG1997002449A patent/SG60085A1/en unknown
- 1997-07-11 YU YU30197A patent/YU30197A/sh unknown
- 1997-07-14 NZ NZ328330A patent/NZ328330A/en unknown
- 1997-07-14 ZA ZA9706224A patent/ZA976224B/xx unknown
- 1997-07-14 HU HU9701194A patent/HUP9701194A3/hu unknown
- 1997-07-14 IL IL12129997A patent/IL121299A/en not_active IP Right Cessation
- 1997-07-14 CA CA002210044A patent/CA2210044C/en not_active Expired - Fee Related
- 1997-07-14 US US08/891,781 patent/US5889026A/en not_active Expired - Lifetime
- 1997-07-14 PE PE1997000623A patent/PE86398A1/es not_active Application Discontinuation
- 1997-07-16 MX MX9705387A patent/MX9705387A/es unknown
- 1997-07-16 UY UY24625A patent/UY24625A1/es unknown
- 1997-07-16 ID IDP972464A patent/ID19632A/id unknown
- 1997-07-16 AR ARP970103182A patent/AR007897A1/es active IP Right Grant
- 1997-07-16 AR ARP970103183A patent/AR007898A1/es unknown
- 1997-07-17 CO CO97040541A patent/CO4900064A1/es unknown
- 1997-07-17 JP JP19217397A patent/JP3179050B2/ja not_active Expired - Fee Related
- 1997-07-17 MA MA24723A patent/MA24274A1/fr unknown
- 1997-07-17 CZ CZ19972274A patent/CZ290898B6/cs not_active IP Right Cessation
- 1997-07-18 HR HR97105366.5A patent/HRP970394A2/hr not_active Application Discontinuation
- 1997-07-18 TR TR97/00659A patent/TR199700659A2/xx unknown
- 1997-07-18 AU AU28756/97A patent/AU719352B2/en not_active Ceased
- 1997-07-18 RU RU97113374/04A patent/RU2178412C2/ru not_active IP Right Cessation
- 1997-07-18 CN CN97114707A patent/CN1120154C/zh not_active Expired - Fee Related
- 1997-07-18 NO NO973337A patent/NO308657B1/no unknown
- 1997-07-18 PL PL97321201A patent/PL321201A1/xx unknown
- 1997-07-21 BR BR9704031A patent/BR9704031A/pt not_active IP Right Cessation
- 1997-07-22 KR KR1019970034233A patent/KR100235804B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
YU30197A (sh)	1999-12-27
IL121299A (en)	2001-12-23
AU719352B2 (en)	2000-05-04
NO308657B1 (no)	2000-10-09
CO4900064A1 (es)	2000-03-27
CA2210044C (en)	2006-02-14
CN1120154C (zh)	2003-09-03
ZA976224B (en)	1998-01-19
KR100235804B1 (ko)	1999-12-15
PT824098E (pt)	2002-04-29
RU2178412C2 (ru)	2002-01-20
ID19632A (id)	1998-07-23
BR9704031A (pt)	1998-12-29
US5889026A (en)	1999-03-30
PE86398A1 (es)	1998-12-10
CZ290898B6 (cs)	2002-11-13
HUP9701194A2 (hu)	1999-05-28
UY24625A1 (es)	2000-12-29
IL121299A0 (en)	1998-01-04
CZ227497A3 (cs)	1998-02-18
MA24274A1 (fr)	1998-04-01
TR199700659A2 (xx)	1998-02-21
MX9705387A (es)	1998-01-31
PL321201A1 (en)	1998-02-02
AU2875697A (en)	1998-01-29
HK1009124A1 (en)	1999-05-28
DE69707782T2 (de)	2002-06-20
DK0824098T3 (da)	2002-02-18
HU9701194D0 (en)	1997-09-29
EP0824098B1 (en)	2001-10-31
NO973337D0 (no)	1997-07-18
KR980009244A (ko)	1998-04-30
AR007898A1 (es)	1999-11-24
AR007897A1 (es)	1999-11-24
CN1171396A (zh)	1998-01-28
SG60085A1 (en)	1999-02-22
TW498067B (en)	2002-08-11
NZ328330A (en)	1998-05-27
DE69707782D1 (de)	2001-12-06
ATE207899T1 (de)	2001-11-15
ES2164967T3 (es)	2002-03-01
JPH1067742A (ja)	1998-03-10
HUP9701194A3 (en)	1999-06-28
CA2210044A1 (en)	1998-01-19
NO973337L (no)	1998-01-20
JP3179050B2 (ja)	2001-06-25
EP0824098A1 (en)	1998-02-18

Publication	Publication Date	Title
HRP970394A2 (en)	1998-06-30	4-hydroxy-piperidine derivatives
MXPA97005387A (en)	1998-01-01	Derivatives of the 4-hidroxi-piperid
US5674881A (en)	1997-10-07	Quaternary ammonium salts of aromatic amine compounds, their preparation and pharmaceutical compositions in which they are present
EP0650476B1 (en)	2002-06-26	Peripheral vasodilating agent containing n-acylated 4-amino piperidine derivatives as active ingredients
JP3140294B2 (ja)	2001-03-05	アリール置換複素環式化合物
JP6250403B2 (ja)	2017-12-20	ヒストン脱アセチル化酵素阻害剤
NO178572B (no)	1996-01-15	Nye N-alkylenpiperidinoforbindelser og deres enantiomere og farmasöytiske blandinger inneholdende dem
SK3032001A3 (en)	2002-04-04	4,4-biarylpiperidine derivatives with opioid receptor activity
SK82498A3 (en)	1999-02-11	4-substituted piperidine analogs and their use as subtype selective nmda receptor antagonists
JP2001525406A (ja)	2001-12-11	新規な化合物
US8252935B2 (en)	2012-08-28	Piperidinyl and piperazinyl modulators of γ-secretase
CN101268046A (zh)	2008-09-17	作为毒蕈碱性受体拮抗剂的碳酰胺衍生物
EP0846683A1 (en)	1998-06-10	4-Hydroxy-piperidine derivatives
RU2184112C2 (ru)	2002-06-27	Производные пиперидина и фармацевтический препарат на их основе
JP2003501415A (ja)	2003-01-14	エタンスルホニル−ピペリジン誘導体
WO2009034432A2 (en)	2009-03-19	Novel compounds active as muscarinic receptor antagonists
EA002424B1 (ru)	2002-04-25	Соединения четвертичного аммония как антагонисты тахикинина
US6060485A (en)	2000-05-09	Arylacetic amide derivative or salt thereof, and pharmaceutical comprising it
HK1009124B (en)	2002-09-06	4-hydroxy-piperidine derivatives
US4518713A (en)	1985-05-21	Analgesic substituted-1-aminoalkylamino-4-aryloxypiperidines
HK1003708B (en)	2002-09-27	Peripheral vasodilating agent containing n-acylated 4-amino piperidine derivatives as active ingredients

Legal Events

Date	Code	Title
1998-06-30	A1OB	Publication of a patent application
1998-12-15	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2011-02-28	ODBC	Application rejected