AU2002351816B8 - Pyridine Substituted Isoquinoline Derivatives - Google Patents
Pyridine Substituted Isoquinoline Derivatives Download PDFInfo
- Publication number
- AU2002351816B8 AU2002351816B8 AU2002351816A AU2002351816A AU2002351816B8 AU 2002351816 B8 AU2002351816 B8 AU 2002351816B8 AU 2002351816 A AU2002351816 A AU 2002351816A AU 2002351816 A AU2002351816 A AU 2002351816A AU 2002351816 B8 AU2002351816 B8 AU 2002351816B8
- Authority
- AU
- Australia
- Prior art keywords
- lower alkyl
- hydrogen
- compound
- pyridin
- formula
- 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.)
- Ceased
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 2
- 150000002537 isoquinolines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 175
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- AWSWSDJGJTXACL-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-5-methylpyridin-4-amine Chemical compound C1=C(N)C(C)=CN=C1N1CC2=CC=CC=C2CC1 AWSWSDJGJTXACL-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- AKEQXIQPNAIIMS-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=NC(C)=CC(N2CC3=CC=CC=C3CC2)=C1 AKEQXIQPNAIIMS-UHFFFAOYSA-N 0.000 claims description 3
- UPWCCXZYHXYHRR-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-6-ethylpyridin-4-amine Chemical compound CCC1=CC(N)=CC(N2CC3=CC=CC=C3CC2)=N1 UPWCCXZYHXYHRR-UHFFFAOYSA-N 0.000 claims description 3
- CLOBRFOJYSYUJF-UHFFFAOYSA-N 2-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)-5-methylpyridin-4-yl]amino]ethanol Chemical compound C1=C(NCCO)C(C)=CN=C1N1CC2=CC=CC=C2CC1 CLOBRFOJYSYUJF-UHFFFAOYSA-N 0.000 claims description 3
- CIOBWNSCGKJAQU-UHFFFAOYSA-N 2-pyridin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC=CC=C2CN1C1=CC=NC=C1 CIOBWNSCGKJAQU-UHFFFAOYSA-N 0.000 claims description 3
- KZFAWZANSXHSCN-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)-6-methylpyridin-2-amine Chemical compound NC1=NC(C)=CC(N2CC3=CC=CC=C3CC2)=C1 KZFAWZANSXHSCN-UHFFFAOYSA-N 0.000 claims description 3
- SNEWDBZYBSANKX-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)pyridin-2-amine Chemical compound C1=NC(N)=CC(N2CC3=CC=CC=C3CC2)=C1 SNEWDBZYBSANKX-UHFFFAOYSA-N 0.000 claims description 3
- BCHRZZNYEZLETK-UHFFFAOYSA-N [4-amino-6-(3,4-dihydro-1h-isoquinolin-2-yl)pyridin-2-yl]methanol Chemical compound NC1=CC(CO)=NC(N2CC3=CC=CC=C3CC2)=C1 BCHRZZNYEZLETK-UHFFFAOYSA-N 0.000 claims description 3
- RLTYKBNDXIAOJH-UHFFFAOYSA-N 2-(4-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyridin-4-amine Chemical compound C1C2=CC=CC=C2C(C)CN1C1=CC(N)=CC=N1 RLTYKBNDXIAOJH-UHFFFAOYSA-N 0.000 claims description 2
- KVVJFPPUFLMQDI-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)pyridin-3-amine Chemical compound NC1=CN=CC=C1N1CC2=CC=CC=C2CC1 KVVJFPPUFLMQDI-UHFFFAOYSA-N 0.000 claims 6
- NSYAHPROSUNCTM-UHFFFAOYSA-N 2-(5-methylpyridin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound N1=CC(C)=CC=C1N1CC2=CC=CC=C2CC1 NSYAHPROSUNCTM-UHFFFAOYSA-N 0.000 claims 5
- 241000080590 Niso Species 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- YAFQFNOUYXZVPZ-UHFFFAOYSA-N liproxstatin-1 Chemical compound ClC1=CC=CC(CNC=2C3(CCNCC3)NC3=CC=CC=C3N=2)=C1 YAFQFNOUYXZVPZ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 70
- AZKCYSCBPAJCPT-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)pyridin-4-amine Chemical compound NC1=CC=NC(N2CC3=CC=CC=C3CC2)=C1 AZKCYSCBPAJCPT-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 32
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- 238000007429 general method Methods 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 239000012458 free base Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 22
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 21
- 239000002178 crystalline material Substances 0.000 description 19
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 229910004298 SiO 2 Inorganic materials 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- -1 for example Chemical group 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 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 7
- 238000001816 cooling Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000012256 powdered iron Substances 0.000 description 6
- PWRLUVIRGGDEJK-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-n-ethylpyridin-4-amine Chemical compound CCNC1=CC=NC(N2CC3=CC=CC=C3CC2)=C1 PWRLUVIRGGDEJK-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 238000000605 extraction Methods 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- FTLLNKOZZWBNGQ-UHFFFAOYSA-N (4-amino-6-bromopyridin-2-yl)methanol Chemical compound NC1=CC(Br)=NC(CO)=C1 FTLLNKOZZWBNGQ-UHFFFAOYSA-N 0.000 description 4
- YSDYZWDWFNMKFW-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-6-methylpyridin-4-amine Chemical compound CC1=CC(N)=CC(N2CC3=CC=CC=C3CC2)=N1 YSDYZWDWFNMKFW-UHFFFAOYSA-N 0.000 description 4
- BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 4
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- 230000004770 neurodegeneration Effects 0.000 description 4
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- 239000008188 pellet Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
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- 230000009870 specific binding Effects 0.000 description 4
- NLCMEPOEDTUKDY-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC(N2CC3=CC=CC=C3CC2)=C1 NLCMEPOEDTUKDY-UHFFFAOYSA-N 0.000 description 3
- OBNFILXMXHDTDL-UHFFFAOYSA-N 2-(3-nitropyridin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound [O-][N+](=O)C1=CC=CN=C1N1CC2=CC=CC=C2CC1 OBNFILXMXHDTDL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- XICXWCILIDFKQV-UHFFFAOYSA-N 2-bromo-4-nitro-1-oxido-5,6,7,8-tetrahydroquinolin-1-ium Chemical compound C1CCCC2=C1[N+]([O-])=C(Br)C=C2[N+](=O)[O-] XICXWCILIDFKQV-UHFFFAOYSA-N 0.000 description 3
- RYMSPPQBKBRUQJ-UHFFFAOYSA-N 2-bromo-6-ethyl-1-oxidopyridin-1-ium Chemical compound CCC1=CC=CC(Br)=[N+]1[O-] RYMSPPQBKBRUQJ-UHFFFAOYSA-N 0.000 description 3
- GNTGEMWEXKBWBX-UHFFFAOYSA-N 2-bromopyridin-4-amine Chemical compound NC1=CC=NC(Br)=C1 GNTGEMWEXKBWBX-UHFFFAOYSA-N 0.000 description 3
- YQBRMUXRAFVSPK-UHFFFAOYSA-N 6-bromo-4-nitropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC(Br)=N1 YQBRMUXRAFVSPK-UHFFFAOYSA-N 0.000 description 3
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- 239000012043 crude product Substances 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- SYCPILSKZWDGPU-UHFFFAOYSA-N ethyl 2-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)-6-methylpyridin-4-yl]amino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC(C)=NC(N2CC3=CC=CC=C3CC2)=C1 SYCPILSKZWDGPU-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- MNXKPYGCTXTCRR-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-yl)pyridin-4-yl]benzamide Chemical compound C=1C=NC(N2CC3=CC=CC=C3CC2)=CC=1NC(=O)C1=CC=CC=C1 MNXKPYGCTXTCRR-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- BHXPHZOOSSXCHR-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-n-methylpyridin-4-amine Chemical compound CNC1=CC=NC(N2CC3=CC=CC=C3CC2)=C1 BHXPHZOOSSXCHR-UHFFFAOYSA-N 0.000 description 2
- MLZJNABNOIALND-UHFFFAOYSA-N 2-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)-6-methylpyridin-4-yl]amino]ethanol Chemical compound CC1=CC(NCCO)=CC(N2CC3=CC=CC=C3CC2)=N1 MLZJNABNOIALND-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/24—Antidepressants
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01126467 | 2001-11-09 | ||
| EP01126467.8 | 2001-11-09 | ||
| PCT/EP2002/012240 WO2003040128A1 (en) | 2001-11-09 | 2002-11-02 | Pyridine derivatives as nmda receptor ligands |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2002351816A1 AU2002351816A1 (en) | 2003-07-24 |
| AU2002351816B2 AU2002351816B2 (en) | 2008-03-06 |
| AU2002351816B8 true AU2002351816B8 (en) | 2008-04-03 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002351816A Ceased AU2002351816B8 (en) | 2001-11-09 | 2002-11-02 | Pyridine Substituted Isoquinoline Derivatives |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6831087B2 (enExample) |
| EP (1) | EP1448547B1 (enExample) |
| JP (1) | JP4188837B2 (enExample) |
| KR (1) | KR100589995B1 (enExample) |
| CN (1) | CN100516061C (enExample) |
| AR (1) | AR037221A1 (enExample) |
| AT (1) | ATE293619T1 (enExample) |
| AU (1) | AU2002351816B8 (enExample) |
| BR (1) | BR0213977A (enExample) |
| CA (1) | CA2467973C (enExample) |
| DE (1) | DE60203820T2 (enExample) |
| ES (1) | ES2240829T3 (enExample) |
| MX (1) | MXPA04004308A (enExample) |
| PL (1) | PL369544A1 (enExample) |
| RU (1) | RU2303037C2 (enExample) |
| WO (1) | WO2003040128A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007008816A (ja) * | 2003-10-15 | 2007-01-18 | Ube Ind Ltd | 新規イソキノリン誘導体 |
| US20050089559A1 (en) * | 2003-10-23 | 2005-04-28 | Istvan Szelenyi | Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains |
| RU2320654C1 (ru) * | 2006-05-24 | 2008-03-27 | Государственное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия Федерального агентства по здравоохранению и социальному развитию" (ГОУ ВПО ПГФА Росздрава) | 2,2-ДИМЕТИЛ-4-(4,6-ДИМЕТИЛ-2-ПИРИДОН-3-ИЛ)-1,2-ДИГИДРО-БЕНЗО[f]ИЗОХИНОЛИНА ГИДРОХЛОРИД, ПРОЯВЛЯЮЩИЙ ПРЯМОЕ АНТИКОАГУЛЯНТНОЕ ДЕЙСТВИЕ |
| US8722929B2 (en) * | 2006-10-10 | 2014-05-13 | Valeant Pharmaceuticals International | N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators |
| US8367684B2 (en) * | 2007-06-13 | 2013-02-05 | Valeant Pharmaceuticals International | Derivatives of 4-(N-azacycloalkyl) anilides as potassium channel modulators |
| US8563566B2 (en) * | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
| US7786146B2 (en) * | 2007-08-13 | 2010-08-31 | Valeant Pharmaceuticals International | Derivatives of 5-amino-4,6-disubstituted indole and 5-amino-4,6-disubstituted indoline as potassium channel modulators |
| EP2065381A1 (de) | 2007-10-18 | 2009-06-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | CGRP Antagonisten |
| NZ585347A (en) | 2007-10-18 | 2011-09-30 | Boehringer Ingelheim Int | Cgrp antagonists |
| EP2062889A1 (de) * | 2007-11-22 | 2009-05-27 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verbindungen |
| CA2705405A1 (en) | 2007-11-22 | 2009-05-28 | Boehringer Ingelheim International Gmbh | New compounds |
| CA2705599A1 (en) * | 2007-11-22 | 2009-05-28 | Boehringer Ingelheim International Gmbh | New compounds |
| EA014100B1 (ru) * | 2008-02-21 | 2010-08-30 | Общество С Ограниченной Ответственностью "Валексфарм" | Производные 2,4-диаминопиридина, фармацевтическая композиция, лекарственное средство на их основе для лечения или предупреждения заболеваний и нарушений, вызванных гиперактивацией nmda-рецепторов и/или в качестве стимуляторов когнитивных функций и способ лечения |
| RU2438672C1 (ru) * | 2010-04-30 | 2012-01-10 | Общество с ограниченной ответственностью "Клевер Фарм" | Агент, проявляющий свойства активатора когнитивных функций (варианты) |
| WO2025124571A1 (zh) * | 2023-12-14 | 2025-06-19 | 斯莱普泰(上海)生物医药科技有限公司 | Nmda受体拮抗剂及其用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997023458A1 (en) * | 1995-12-22 | 1997-07-03 | Warner-Lambert Company | Subtype-selective nmda receptor ligands and the use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE524440T1 (de) * | 1998-05-25 | 2011-09-15 | Abbott Gmbh & Co Kg | Heterocyclische substituierte amide, deren herstellung und anwendung |
| DK1088818T3 (da) | 1999-10-01 | 2005-03-14 | Hoffmann La Roche | Quinolin-4-yl-derivater |
| US6440995B1 (en) * | 1999-10-01 | 2002-08-27 | Hoffman-La Roche Inc. | Quinolin-4-yl derivatives |
| US6339093B1 (en) * | 1999-10-08 | 2002-01-15 | Hoffmann-La Roche Inc. | Isoquinoline derivatives |
-
2002
- 2002-10-29 US US10/282,365 patent/US6831087B2/en not_active Expired - Fee Related
- 2002-11-02 ES ES02787541T patent/ES2240829T3/es not_active Expired - Lifetime
- 2002-11-02 WO PCT/EP2002/012240 patent/WO2003040128A1/en not_active Ceased
- 2002-11-02 PL PL02369544A patent/PL369544A1/xx unknown
- 2002-11-02 KR KR1020047007031A patent/KR100589995B1/ko not_active Expired - Fee Related
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- 2002-11-02 BR BR0213977-4A patent/BR0213977A/pt not_active IP Right Cessation
- 2002-11-02 AU AU2002351816A patent/AU2002351816B8/en not_active Ceased
- 2002-11-02 JP JP2003542174A patent/JP4188837B2/ja not_active Expired - Fee Related
- 2002-11-02 MX MXPA04004308A patent/MXPA04004308A/es active IP Right Grant
- 2002-11-02 RU RU2004117595/04A patent/RU2303037C2/ru not_active IP Right Cessation
- 2002-11-02 CN CNB028222512A patent/CN100516061C/zh not_active Expired - Fee Related
- 2002-11-02 AT AT02787541T patent/ATE293619T1/de not_active IP Right Cessation
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- 2002-11-02 DE DE60203820T patent/DE60203820T2/de not_active Expired - Lifetime
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997023458A1 (en) * | 1995-12-22 | 1997-07-03 | Warner-Lambert Company | Subtype-selective nmda receptor ligands and the use thereof |
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| Chatani et al J. Am. Chem. Soc. 2001 123(44), 10935-10941 * |
| Chatani et al. J. Am. Chem. Soc. 2000 122(51), 12882-12883 * |
| Saxena et al Indian Journal of Chemistry, section B: Organic Chemistry including Medicinal Chemistry 1980 19B(10), 873-8 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60203820D1 (de) | 2005-05-25 |
| ES2240829T3 (es) | 2005-10-16 |
| JP4188837B2 (ja) | 2008-12-03 |
| KR20050042252A (ko) | 2005-05-06 |
| CN100516061C (zh) | 2009-07-22 |
| EP1448547B1 (en) | 2005-04-20 |
| US6831087B2 (en) | 2004-12-14 |
| CA2467973C (en) | 2009-09-01 |
| RU2303037C2 (ru) | 2007-07-20 |
| MXPA04004308A (es) | 2004-08-11 |
| US20030119870A1 (en) | 2003-06-26 |
| RU2004117595A (ru) | 2006-01-10 |
| BR0213977A (pt) | 2004-08-31 |
| AU2002351816B2 (en) | 2008-03-06 |
| KR100589995B1 (ko) | 2006-06-19 |
| ATE293619T1 (de) | 2005-05-15 |
| CN1585762A (zh) | 2005-02-23 |
| AR037221A1 (es) | 2004-10-27 |
| JP2005513004A (ja) | 2005-05-12 |
| EP1448547A1 (en) | 2004-08-25 |
| PL369544A1 (en) | 2005-05-02 |
| DE60203820T2 (de) | 2006-02-23 |
| WO2003040128A1 (en) | 2003-05-15 |
| CA2467973A1 (en) | 2003-05-15 |
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