HRP970394A2 - 4-hydroxy-piperidine derivatives - Google Patents
4-hydroxy-piperidine derivativesInfo
- Publication number
- HRP970394A2 HRP970394A2 HR97105366.5A HRP970394A HRP970394A2 HR P970394 A2 HRP970394 A2 HR P970394A2 HR P970394 A HRP970394 A HR P970394A HR P970394 A2 HRP970394 A2 HR P970394A2
- Authority
- HR
- Croatia
- Prior art keywords
- hydroxy
- benzyl
- piperidin
- compound
- formula
- Prior art date
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
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- 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
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- 239000000243 solution Substances 0.000 description 43
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- 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
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- 239000000741 silica gel Substances 0.000 description 30
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- 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
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- 238000002474 experimental method Methods 0.000 description 7
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- 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
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
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- 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
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- 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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- 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
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- 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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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
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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
- A61P25/14—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
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- 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
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
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR97105366.5A HRP970394A2 (en) | 1996-07-19 | 1997-07-18 | 4-hydroxy-piperidine derivatives |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US5889026A (es) |
| EP (1) | EP0824098B1 (es) |
| JP (1) | JP3179050B2 (es) |
| KR (1) | KR100235804B1 (es) |
| CN (1) | CN1120154C (es) |
| AR (2) | AR007898A1 (es) |
| AT (1) | ATE207899T1 (es) |
| AU (1) | AU719352B2 (es) |
| BR (1) | BR9704031A (es) |
| CA (1) | CA2210044C (es) |
| CO (1) | CO4900064A1 (es) |
| CZ (1) | CZ290898B6 (es) |
| DE (1) | DE69707782T2 (es) |
| DK (1) | DK0824098T3 (es) |
| ES (1) | ES2164967T3 (es) |
| HK (1) | HK1009124A1 (es) |
| HR (1) | HRP970394A2 (es) |
| HU (1) | HUP9701194A3 (es) |
| ID (1) | ID19632A (es) |
| IL (1) | IL121299A (es) |
| MA (1) | MA24274A1 (es) |
| MX (1) | MX9705387A (es) |
| NO (1) | NO308657B1 (es) |
| NZ (1) | NZ328330A (es) |
| PE (1) | PE86398A1 (es) |
| PL (1) | PL321201A1 (es) |
| PT (1) | PT824098E (es) |
| RU (1) | RU2178412C2 (es) |
| SG (1) | SG60085A1 (es) |
| TR (1) | TR199700659A2 (es) |
| TW (1) | TW498067B (es) |
| UY (1) | UY24625A1 (es) |
| YU (1) | YU30197A (es) |
| ZA (1) | ZA976224B (es) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
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| IL125658A0 (en) | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
| US6339087B1 (en) | 1997-08-18 | 2002-01-15 | Syntex (U.S.A.) Llc | Cyclic amine derivatives-CCR-3 receptor antagonists |
| MXPA00011889A (es) * | 1998-06-02 | 2003-04-25 | Osi Pharm Inc | Composiciones de pirrolo (2,3d) piridina y su uso. |
| CO5150201A1 (es) * | 1998-09-07 | 2002-04-29 | Hoffmann La Roche | Derivados de piperidina |
| BR9915735A (pt) | 1998-11-20 | 2001-09-04 | Hoffmann La Roche | Antagonistas receptores de ccr-3 de piperidina |
| TWI254043B (en) * | 1999-06-08 | 2006-05-01 | Hoffmann La Roche | Ethanesulfonyl-piperidine derivatives having good affinity to N-methyl-D-aspartate (NMDA) receptor |
| US6432985B2 (en) * | 2000-04-25 | 2002-08-13 | Hoffmann-La Roche Inc. | Neuroprotective substituted piperidine compounds with activity as NMDA NR2B subtype selective antagonists |
| PA8525601A1 (es) * | 2000-08-21 | 2002-04-25 | Hoffmann La Roche | Profarmacos de (3s,4s)-4-bencil-1-[2-(4-hidroxi-bencenosulfonil)-etil]-piperidin-3-ol |
| EP1674087A1 (en) | 2000-10-02 | 2006-06-28 | Pfizer Products Inc. | Prophylactic use of n-methyl-d-aspartate (NMDA) antagonists |
| US6680324B2 (en) * | 2000-12-01 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| US7375136B2 (en) * | 2001-03-08 | 2008-05-20 | Emory University | pH-dependent NMDA receptor antagonists |
| MXPA04000737A (es) * | 2001-07-24 | 2004-07-08 | Richter Gedeon Vegyeszet | Derivados de piperidina como antagonistas receptores de nmda. |
| EP1450811B1 (en) * | 2001-11-30 | 2009-10-21 | OSI Pharmaceuticals, Inc. | Compounds specific to adenosine A1 and A3 receptors and uses thereof |
| CN1620294A (zh) | 2001-12-20 | 2005-05-25 | Osi药物公司 | 嘧啶a2b选择性拮抗剂化合物,它们的合成及用途 |
| US6951884B2 (en) * | 2002-06-12 | 2005-10-04 | Hoffmann-La Roche Inc. | Fluorobenzamides and uses thereof |
| WO2005030720A1 (ja) * | 2003-09-25 | 2005-04-07 | Shionogi & Co., Ltd. | Ｎｍｄａ受容体拮抗作用を有するピペリジン誘導体 |
| CA2543287A1 (en) * | 2003-10-23 | 2005-05-06 | 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 |
| US8420680B2 (en) * | 2007-06-29 | 2013-04-16 | Emory University | NMDA receptor antagonists for neuroprotection |
| 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 |
| EP2296658A4 (en) * | 2008-05-09 | 2014-01-15 | Univ Emory | ANTAGONISTS OF NMDA RECEPTORS USEFUL FOR THE TREATMENT OF NEUROPSYCHIATRIC DISORDERS |
| US7874106B2 (en) * | 2009-02-13 | 2011-01-25 | Ykk Corporation Of America | Sill flashing and end dam assembly |
| BR112012009123A2 (pt) * | 2009-10-19 | 2017-09-19 | Amicus Therapeutics Inc | novas composições para a prevenção e/ou tratamento de distúrbios de depósito lisossômico |
| ES2617192T3 (es) * | 2009-10-19 | 2017-06-15 | Amicus Therapeutics, Inc. | Nuevas composiciones para prevenir y/o tratar trastornos degenerativos del sistema nervioso central |
| EP3233799B1 (en) | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| US10633336B2 (en) | 2014-12-19 | 2020-04-28 | The Broad Institute, Inc. | Dopamine D2 receptor ligands |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2099339C1 (ru) * | 1990-02-06 | 1997-12-20 | Пфайзер Инк. | Производные пиперидина |
| 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 (es) * | 1993-09-02 | 1996-07-21 | Hoffmann La Roche | |
| ATE183184T1 (de) * | 1994-01-31 | 1999-08-15 | Pfizer | Neuroprotektive chroman verbindungen |
| 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 DE DE69707782T patent/DE69707782T2/de not_active Expired - Lifetime
- 1997-07-10 ES ES97111742T patent/ES2164967T3/es not_active Expired - Lifetime
- 1997-07-10 PT PT97111742T patent/PT824098E/pt unknown
- 1997-07-10 AT AT97111742T patent/ATE207899T1/de active
- 1997-07-10 DK DK97111742T patent/DK0824098T3/da active
- 1997-07-10 EP EP97111742A patent/EP0824098B1/en not_active Expired - Lifetime
- 1997-07-11 SG SG1997002449A patent/SG60085A1/en unknown
- 1997-07-11 YU YU30197A patent/YU30197A/sh unknown
- 1997-07-14 US US08/891,781 patent/US5889026A/en not_active Expired - Lifetime
- 1997-07-14 IL IL12129997A patent/IL121299A/en not_active IP Right Cessation
- 1997-07-14 PE PE1997000623A patent/PE86398A1/es not_active Application Discontinuation
- 1997-07-14 ZA ZA9706224A patent/ZA976224B/xx unknown
- 1997-07-14 NZ NZ328330A patent/NZ328330A/en unknown
- 1997-07-14 CA CA002210044A patent/CA2210044C/en not_active Expired - Fee Related
- 1997-07-14 HU HU9701194A patent/HUP9701194A3/hu unknown
- 1997-07-16 MX MX9705387A patent/MX9705387A/es unknown
- 1997-07-16 AR ARP970103183A patent/AR007898A1/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
- 1997-07-17 CZ CZ19972274A patent/CZ290898B6/cs not_active IP Right Cessation
- 1997-07-17 JP JP19217397A patent/JP3179050B2/ja not_active Expired - Fee Related
- 1997-07-17 CO CO97040541A patent/CO4900064A1/es unknown
- 1997-07-17 MA MA24723A patent/MA24274A1/fr unknown
- 1997-07-18 RU RU97113374/04A patent/RU2178412C2/ru not_active IP Right Cessation
- 1997-07-18 HR HR97105366.5A patent/HRP970394A2/hr not_active Application Discontinuation
- 1997-07-18 NO NO973337A patent/NO308657B1/no unknown
- 1997-07-18 PL PL97321201A patent/PL321201A1/xx unknown
- 1997-07-18 AU AU28756/97A patent/AU719352B2/en not_active Ceased
- 1997-07-18 TR TR97/00659A patent/TR199700659A2/xx unknown
- 1997-07-18 CN CN97114707A patent/CN1120154C/zh not_active Expired - Fee Related
- 1997-07-21 BR BR9704031A patent/BR9704031A/pt not_active IP Right Cessation
- 1997-07-22 KR KR1019970034233A patent/KR100235804B1/ko not_active IP Right Cessation
-
1998
- 1998-08-13 HK HK98109919A patent/HK1009124A1/xx not_active IP Right Cessation
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