DE19812331A1 - Piperidinderivate - Google Patents
PiperidinderivateInfo
- Publication number
- DE19812331A1 DE19812331A1 DE19812331A DE19812331A DE19812331A1 DE 19812331 A1 DE19812331 A1 DE 19812331A1 DE 19812331 A DE19812331 A DE 19812331A DE 19812331 A DE19812331 A DE 19812331A DE 19812331 A1 DE19812331 A1 DE 19812331A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- compound
- fluorobenzyl
- piperidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000003053 piperidines Chemical class 0.000 title claims abstract description 4
- 230000004770 neurodegeneration Effects 0.000 title claims description 8
- 208000015122 neurodegenerative disease Diseases 0.000 title claims description 8
- 229940123511 Excitatory amino acid receptor antagonist Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 14
- 206010008118 cerebral infarction Diseases 0.000 claims description 14
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 201000006474 Brain Ischemia Diseases 0.000 claims description 7
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 230000007574 infarction Effects 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- GRCRMRUZDNKSBD-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]prop-1-enyl]-3h-1,3-benzothiazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CC=CC=2C=C3SC(=O)NC3=CC=2)CC1 GRCRMRUZDNKSBD-UHFFFAOYSA-N 0.000 claims description 3
- YNWAFHDAQQTVIT-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3OC(=O)NC3=CC=2)CC1 YNWAFHDAQQTVIT-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- KSTICMFAFQGYSN-UHFFFAOYSA-N 5-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]prop-1-enyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CC=CC=2C=C3NC(=O)NC3=CC=2)CC1 KSTICMFAFQGYSN-UHFFFAOYSA-N 0.000 claims description 2
- CQYRNVNODQPZDL-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]prop-1-enyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CC=CC=2C=C3OC(=O)NC3=CC=2)CC1 CQYRNVNODQPZDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003194 amino acid receptor blocking agent Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 230000002461 excitatory amino acid Effects 0.000 claims 1
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- 125000001475 halogen functional group Chemical group 0.000 abstract 1
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- 239000004480 active ingredient Substances 0.000 description 17
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- -1 methylsulfonyloxy Chemical group 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 6
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- UYNVMODNBIQBMV-UHFFFAOYSA-N 4-[1-hydroxy-2-[4-(phenylmethyl)-1-piperidinyl]propyl]phenol Chemical compound C1CC(CC=2C=CC=CC=2)CCN1C(C)C(O)C1=CC=C(O)C=C1 UYNVMODNBIQBMV-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 229960003998 ifenprodil Drugs 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GGUSQTSTQSHJAH-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)piperidin-1-yl]ethanol Chemical compound C=1C=C(Cl)C=CC=1C(O)CN(CC1)CCC1CC1=CC=C(F)C=C1 GGUSQTSTQSHJAH-UHFFFAOYSA-N 0.000 description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 229950005455 eliprodil Drugs 0.000 description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
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- 241001026509 Kata Species 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
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- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
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- 239000002585 base Substances 0.000 description 2
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 239000008101 lactose Substances 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 1
- OJKWWANXBGLGQN-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]piperidine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1CC1CCNCC1 OJKWWANXBGLGQN-UHFFFAOYSA-N 0.000 description 1
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
-
- 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
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19812331A DE19812331A1 (de) | 1998-03-20 | 1998-03-20 | Piperidinderivate |
| HU0101220A HUP0101220A3 (en) | 1998-03-20 | 1999-03-11 | Nmda receptor antagonist 1-(3-heteroaryl propyl- or-prop-2-enyl)-4-benzylpiperidines, pharmaceutical compositions containing them and process for their preparation |
| CN99804190A CN1123571C (zh) | 1998-03-20 | 1999-03-11 | 用作nmda受体拮抗剂的1－(3－杂芳基丙基－或－丙－2－烯基)－4－苄基哌啶 |
| RU2000126475/04A RU2217429C2 (ru) | 1998-03-20 | 1999-03-11 | 1-(3-гетероарилпропил или проп-2-енил)-4-бензилпиперидины, способ их получения и фармацевтическая композиция на их основе |
| AT99915568T ATE416173T1 (de) | 1998-03-20 | 1999-03-11 | 1-(3 -heteroarylpropyl- oder -prop -2-enyl) -4- benzylpiperidine als nmda-rezeptor-antagonisten |
| EP99915568A EP1068202B1 (de) | 1998-03-20 | 1999-03-11 | 1-(3 -heteroarylpropyl- oder -prop -2-enyl) -4-benzylpiperidine als nmda-rezeptor-antagonisten |
| PCT/EP1999/001573 WO1999048891A1 (de) | 1998-03-20 | 1999-03-11 | 1-(3 -heteroarylpropyl- oder -prop -2-enyl) -4-benzylpiperidine als nmda-rezeptor-antagonisten |
| PL99342732A PL342732A1 (en) | 1998-03-20 | 1999-03-11 | 1-(heteroarylpropyl- or -prop-2-enyl)-4 benzylpiperidine as antagopnists nmda receptor |
| DE59914921T DE59914921D1 (de) | 1998-03-20 | 1999-03-11 | 1-(3 -heteroarylpropyl- oder -prop -2-enyl) -4-benzylpiperidine als nmda-rezeptor-antagonisten |
| ES99915568T ES2316184T3 (es) | 1998-03-20 | 1999-03-11 | 1-(3-heteroarilpropil- o -prop-2-enil)-4-bencilpiperidinas como antagonistas del receptor nmda. |
| BR9908902-5A BR9908902A (pt) | 1998-03-20 | 1999-03-11 | Derivados de piperidina |
| IDW20002091A ID26125A (id) | 1998-03-20 | 1999-03-11 | Derivat-derivat piperidin |
| AU34105/99A AU747900B2 (en) | 1998-03-20 | 1999-03-11 | 1-(3-heteroarylpropyl- or -prop-2-enyl)-4-benzylpiperidines used as NMDA receptor antagonists |
| PT99915568T PT1068202E (pt) | 1998-03-20 | 1999-03-11 | 1-(3-heteroarilpropil- ou propa-2-enil)-4- benzilpiperidinas como antagonistas do receptor nmda |
| SK1369-2000A SK13692000A3 (sk) | 1998-03-20 | 1999-03-11 | Derivát 1-(3-heteroarylpropyl- alebo -prop-2-enyl)-4-benzylpiperidínu ako antagonistu nmda receptora, spôsob jeho prípravy a farmaceutický prostriedok, ktorý ho obsahuje |
| KR1020007010387A KR20010042047A (ko) | 1998-03-20 | 1999-03-11 | Ｎｍｄａ 수용체 길항제로 사용되는1-(3-헤테로아릴프로필-또는-프로프-2-에닐)-4-벤질피페리딘류 |
| DK99915568T DK1068202T3 (da) | 1998-03-20 | 1999-03-11 | 1-(-heteroarylpropyl- eller -prop-2-enyl)-4benzylpipderidiner som NMDA-receptor-antagonister |
| CA002324339A CA2324339C (en) | 1998-03-20 | 1999-03-11 | Piperidine derivatives |
| JP2000537874A JP4451565B2 (ja) | 1998-03-20 | 1999-03-11 | ピペリジン誘導体 |
| US09/646,185 US6548516B1 (en) | 1998-03-20 | 1999-03-11 | 1-(3-heteroarylpropyl- or -prop-2-enyl)-4-benzylpiperidines used as NMDA receptor antagonists |
| ZA9902191A ZA992191B (en) | 1998-03-20 | 1999-03-18 | Piperidine derivatives. |
| ARP990101208A AR014747A1 (es) | 1998-03-20 | 1999-03-19 | Derivados de piperidina, un procedimiento para prepararlos, el empleo de los mismos para preparar un medicamento, una composicion farmaceutica que loscontiene y un procedimiento para obtener esta composicion farmaceutica |
| NO20004668A NO20004668D0 (no) | 1998-03-20 | 2000-09-19 | 1-(3-heteroarylpropyl- eller -prop-2-enyl)-4- benzylpiperidiner anvendt som NMDA-reseptorantagonister |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19812331A DE19812331A1 (de) | 1998-03-20 | 1998-03-20 | Piperidinderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19812331A1 true DE19812331A1 (de) | 1999-09-23 |
Family
ID=7861717
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19812331A Withdrawn DE19812331A1 (de) | 1998-03-20 | 1998-03-20 | Piperidinderivate |
| DE59914921T Expired - Lifetime DE59914921D1 (de) | 1998-03-20 | 1999-03-11 | 1-(3 -heteroarylpropyl- oder -prop -2-enyl) -4-benzylpiperidine als nmda-rezeptor-antagonisten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59914921T Expired - Lifetime DE59914921D1 (de) | 1998-03-20 | 1999-03-11 | 1-(3 -heteroarylpropyl- oder -prop -2-enyl) -4-benzylpiperidine als nmda-rezeptor-antagonisten |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6548516B1 (enExample) |
| EP (1) | EP1068202B1 (enExample) |
| JP (1) | JP4451565B2 (enExample) |
| KR (1) | KR20010042047A (enExample) |
| CN (1) | CN1123571C (enExample) |
| AR (1) | AR014747A1 (enExample) |
| AT (1) | ATE416173T1 (enExample) |
| AU (1) | AU747900B2 (enExample) |
| BR (1) | BR9908902A (enExample) |
| CA (1) | CA2324339C (enExample) |
| DE (2) | DE19812331A1 (enExample) |
| DK (1) | DK1068202T3 (enExample) |
| ES (1) | ES2316184T3 (enExample) |
| HU (1) | HUP0101220A3 (enExample) |
| ID (1) | ID26125A (enExample) |
| NO (1) | NO20004668D0 (enExample) |
| PL (1) | PL342732A1 (enExample) |
| PT (1) | PT1068202E (enExample) |
| RU (1) | RU2217429C2 (enExample) |
| SK (1) | SK13692000A3 (enExample) |
| WO (1) | WO1999048891A1 (enExample) |
| ZA (1) | ZA992191B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10248067A1 (de) * | 2002-10-07 | 2004-04-15 | Proteosys Ag | Heteroarylpropyl-Piperazine und Heteroarylpropyl-Piperidine |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DZ3361A1 (fr) | 2000-05-31 | 2001-12-06 | Warner Lambert Co | Cyclohéxylamines bicycliques et leur utilisation comme antagonistes des récepteurs de nmda |
| DE60112574T2 (de) | 2000-06-06 | 2006-06-08 | Warner-Lambert Co. Llc | Bicyclische cyclohexylamine und ihre verwendung als nmda-rezeptor antagonisten |
| EP1345935A2 (en) | 2000-12-21 | 2003-09-24 | Warner-Lambert Company LLC | Piperidine derivatives as subtype selective n-methyl-d-aspartate antagonists |
| MXPA02002749A (es) | 2001-03-27 | 2002-10-28 | Warner Lambert Co | Derivados de ciclohexilamina como antagonistas del subtipo selectivo del n-metil-d-aspartato. |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| WO2008055945A1 (en) | 2006-11-09 | 2008-05-15 | Probiodrug Ag | 3-hydr0xy-1,5-dihydr0-pyrr0l-2-one derivatives as inhibitors of glutaminyl cyclase for the treatment of ulcer, cancer and other diseases |
| EP2091948B1 (en) | 2006-11-30 | 2012-04-18 | Probiodrug AG | Novel inhibitors of glutaminyl cyclase |
| CN101668525A (zh) | 2007-03-01 | 2010-03-10 | 前体生物药物股份公司 | 谷氨酰胺酰环化酶抑制剂的新用途 |
| US9656991B2 (en) | 2007-04-18 | 2017-05-23 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| ES2548913T3 (es) | 2009-09-11 | 2015-10-21 | Probiodrug Ag | Derivados heterocíclicos como inhibidores de glutaminil ciclasa |
| KR20120107993A (ko) | 2009-12-15 | 2012-10-04 | 뉴롭, 인코포레이티드 | 신경계 장애의 치료를 위한 화합물 |
| WO2011107530A2 (en) | 2010-03-03 | 2011-09-09 | Probiodrug Ag | Novel inhibitors |
| CA2789440C (en) | 2010-03-10 | 2020-03-24 | Probiodrug Ag | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
| JP5945532B2 (ja) | 2010-04-21 | 2016-07-05 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体 |
| CN102133198B (zh) * | 2011-03-09 | 2012-02-08 | 北京四环科宝制药有限公司 | 一种酒石酸艾芬地尔冻干粉针剂及其制备方法 |
| US8530670B2 (en) | 2011-03-16 | 2013-09-10 | Probiodrug Ag | Inhibitors |
| CN103965188A (zh) * | 2013-01-29 | 2014-08-06 | 中山大学 | 含硒多奈哌齐类似物 |
| US10604484B2 (en) * | 2015-04-29 | 2020-03-31 | Janssen Pharmaceutica Nv | Indolone compounds and their use as AMPA receptor modulators |
| ES2865330T3 (es) | 2015-04-29 | 2021-10-15 | Janssen Pharmaceutica Nv | Azabenzimidazoles y su uso como moduladores del receptor AMPA |
| EP3461819B1 (en) | 2017-09-29 | 2020-05-27 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH17194A (en) | 1980-03-06 | 1984-06-19 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives,and pharmaceutical composition containing the same |
| JP3084729B2 (ja) * | 1990-06-15 | 2000-09-04 | 横河電機株式会社 | デジタルオシロスコープ |
| TW281670B (enExample) | 1993-09-02 | 1996-07-21 | Hoffmann La Roche | |
| FR2717810B1 (fr) * | 1994-03-22 | 1996-04-26 | Adir | Nouvelles aminoalkyl benzoxazolinones et benzothiazolinones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| AU3138595A (en) * | 1994-07-20 | 1996-02-16 | Acea Pharmaceuticals, Inc. | Haloperidol analogs and the use thereof |
| ATE174915T1 (de) | 1994-10-31 | 1999-01-15 | Merck Patent Gmbh | Benzylpiperidinderivate mit hoher affinität zu bindungsstellen von aminosäure-rezeptoren |
| ZA9610745B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| DE19643790A1 (de) | 1996-10-30 | 1998-05-07 | Merck Patent Gmbh | Benzoxazol-Derivat |
-
1998
- 1998-03-20 DE DE19812331A patent/DE19812331A1/de not_active Withdrawn
-
1999
- 1999-03-11 DE DE59914921T patent/DE59914921D1/de not_active Expired - Lifetime
- 1999-03-11 JP JP2000537874A patent/JP4451565B2/ja not_active Expired - Fee Related
- 1999-03-11 ES ES99915568T patent/ES2316184T3/es not_active Expired - Lifetime
- 1999-03-11 BR BR9908902-5A patent/BR9908902A/pt not_active IP Right Cessation
- 1999-03-11 SK SK1369-2000A patent/SK13692000A3/sk unknown
- 1999-03-11 AT AT99915568T patent/ATE416173T1/de not_active IP Right Cessation
- 1999-03-11 RU RU2000126475/04A patent/RU2217429C2/ru not_active IP Right Cessation
- 1999-03-11 AU AU34105/99A patent/AU747900B2/en not_active Ceased
- 1999-03-11 PL PL99342732A patent/PL342732A1/xx not_active Application Discontinuation
- 1999-03-11 CA CA002324339A patent/CA2324339C/en not_active Expired - Fee Related
- 1999-03-11 ID IDW20002091A patent/ID26125A/id unknown
- 1999-03-11 HU HU0101220A patent/HUP0101220A3/hu unknown
- 1999-03-11 EP EP99915568A patent/EP1068202B1/de not_active Expired - Lifetime
- 1999-03-11 US US09/646,185 patent/US6548516B1/en not_active Expired - Fee Related
- 1999-03-11 DK DK99915568T patent/DK1068202T3/da active
- 1999-03-11 CN CN99804190A patent/CN1123571C/zh not_active Expired - Fee Related
- 1999-03-11 PT PT99915568T patent/PT1068202E/pt unknown
- 1999-03-11 WO PCT/EP1999/001573 patent/WO1999048891A1/de not_active Ceased
- 1999-03-11 KR KR1020007010387A patent/KR20010042047A/ko not_active Withdrawn
- 1999-03-18 ZA ZA9902191A patent/ZA992191B/xx unknown
- 1999-03-19 AR ARP990101208A patent/AR014747A1/es not_active Application Discontinuation
-
2000
- 2000-09-19 NO NO20004668A patent/NO20004668D0/no not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10248067A1 (de) * | 2002-10-07 | 2004-04-15 | Proteosys Ag | Heteroarylpropyl-Piperazine und Heteroarylpropyl-Piperidine |
Also Published As
| Publication number | Publication date |
|---|---|
| ID26125A (id) | 2000-11-23 |
| DE59914921D1 (de) | 2009-01-15 |
| BR9908902A (pt) | 2000-11-28 |
| NO20004668L (no) | 2000-09-19 |
| RU2217429C2 (ru) | 2003-11-27 |
| HUP0101220A2 (hu) | 2002-05-29 |
| KR20010042047A (ko) | 2001-05-25 |
| PL342732A1 (en) | 2001-07-02 |
| PT1068202E (pt) | 2009-03-06 |
| AR014747A1 (es) | 2001-03-28 |
| NO20004668D0 (no) | 2000-09-19 |
| DK1068202T3 (da) | 2009-03-16 |
| JP4451565B2 (ja) | 2010-04-14 |
| JP2002507613A (ja) | 2002-03-12 |
| ES2316184T3 (es) | 2009-04-01 |
| WO1999048891A1 (de) | 1999-09-30 |
| CN1123571C (zh) | 2003-10-08 |
| EP1068202A1 (de) | 2001-01-17 |
| HUP0101220A3 (en) | 2003-08-28 |
| ZA992191B (en) | 1999-09-29 |
| CA2324339A1 (en) | 1999-09-30 |
| CN1293673A (zh) | 2001-05-02 |
| AU747900B2 (en) | 2002-05-30 |
| SK13692000A3 (sk) | 2001-02-12 |
| AU3410599A (en) | 1999-10-18 |
| EP1068202B1 (de) | 2008-12-03 |
| US6548516B1 (en) | 2003-04-15 |
| ATE416173T1 (de) | 2008-12-15 |
| CA2324339C (en) | 2010-01-12 |
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Legal Events
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| 8139 | Disposal/non-payment of the annual fee |