JP2008508353A - ヒスタミンｈ３受容体リガンドとしてのピペリジン誘導体 - Google Patents
ヒスタミンｈ３受容体リガンドとしてのピペリジン誘導体 Download PDFInfo
- Publication number
- JP2008508353A JP2008508353A JP2007524768A JP2007524768A JP2008508353A JP 2008508353 A JP2008508353 A JP 2008508353A JP 2007524768 A JP2007524768 A JP 2007524768A JP 2007524768 A JP2007524768 A JP 2007524768A JP 2008508353 A JP2008508353 A JP 2008508353A
- Authority
- JP
- Japan
- Prior art keywords
- benzo
- dihydro
- phenyl
- tetrahydro
- indol
- 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.)
- Abandoned
Links
- 102000004384 Histamine H3 receptors Human genes 0.000 title description 15
- 108090000981 Histamine H3 receptors Proteins 0.000 title description 15
- 239000003446 ligand Substances 0.000 title description 8
- 150000003053 piperidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 208000020401 Depressive disease Diseases 0.000 claims abstract description 3
- -1 methoxy, hydroxy Chemical group 0.000 claims description 208
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- ALOCUZOKRULSAA-UHFFFAOYSA-N 1-methylpiperidin-4-amine Chemical compound CN1CCC(N)CC1 ALOCUZOKRULSAA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 4
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229960001340 histamine Drugs 0.000 description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 238000003556 assay Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000012131 assay buffer Substances 0.000 description 6
- 125000006413 ring segment Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
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- 125000003636 chemical group Chemical group 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 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
- 238000002474 experimental method Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 239000002858 neurotransmitter agent Substances 0.000 description 3
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- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 2
- 125000004747 1,1-dimethylethoxycarbonyl group Chemical group CC(C)(OC(=O)*)C 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-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
- C07D401/14—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 three or more hetero rings
-
- 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
-
- 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0401971A SE0401971D0 (sv) | 2004-08-02 | 2004-08-02 | Piperidne derivatives |
| PCT/SE2005/001189 WO2006014136A1 (en) | 2004-08-02 | 2005-07-27 | Piperidine derivatives as histamine h3 receptor ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008508353A true JP2008508353A (ja) | 2008-03-21 |
| JP2008508353A5 JP2008508353A5 (cg-RX-API-DMAC7.html) | 2009-03-12 |
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| JP2007524768A Abandoned JP2008508353A (ja) | 2004-08-02 | 2005-07-27 | ヒスタミンｈ３受容体リガンドとしてのピペリジン誘導体 |
Country Status (14)
| Country | Link |
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| US (1) | US20080064706A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1781613A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2008508353A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20070043998A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1993325A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2005267932A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0514035A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2576112A1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL180548A0 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2007001226A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2007105970A (cg-RX-API-DMAC7.html) |
| SE (1) | SE0401971D0 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2006014136A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200700683B (cg-RX-API-DMAC7.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015522606A (ja) * | 2012-07-20 | 2015-08-06 | ノバルティス アーゲー | カルバメート／尿素誘導体 |
| JP2017507116A (ja) * | 2014-03-07 | 2017-03-16 | ヘルシン ヘルスケア ソシエテ アノニム | ｐ−置換非対称尿素及びその医薬的使用 |
| JP2017520530A (ja) * | 2014-05-19 | 2017-07-27 | メリアル インコーポレイテッド | 駆虫性化合物 |
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| EP1608319A4 (en) | 2003-04-03 | 2007-02-28 | Univ California | IMPROVED HEMMER FOR SOLUBLE EPOXY HYDROLASE |
| CA2559665A1 (en) | 2004-03-16 | 2005-09-29 | The Regents Of The University Of California | Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids |
| CN101084216B (zh) | 2004-10-20 | 2011-09-14 | 加利福尼亚大学董事会 | 可溶性环氧化物水解酶的改进抑制剂 |
| EP2937341B1 (en) | 2004-12-30 | 2017-07-05 | Janssen Pharmaceutica N.V. | 4-(benzyl)-piperazine-1-carboxylic acid phenylamide derivatives and related compounds as modulators of fatty acid amide hydrolase (faah) for the treatment of anxiety, pain and other conditions |
| EP1909797A4 (en) | 2005-08-02 | 2013-02-27 | Neurogen Corp | DIPIPERAZINYL KETONE AND RELATED ANALOG |
| AR059826A1 (es) | 2006-03-13 | 2008-04-30 | Univ California | Inhibidores de urea conformacionalmente restringidos de epoxido hidrolasa soluble |
| CA2692182A1 (en) * | 2007-06-22 | 2008-12-31 | F. Hoffmann-La Roche Ag | Urea and carbamate derivatives as non-nucleoside reverse transcriptase inhibitors |
| CA2705502C (en) | 2007-11-13 | 2016-01-26 | Taisho Pharmaceutical Co., Ltd. | Phenylpyrazole derivatives |
| US8461159B2 (en) | 2008-11-25 | 2013-06-11 | Jannsen Pharmaceutica BV | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| WO2010068452A1 (en) * | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| TW201039822A (en) | 2009-02-06 | 2010-11-16 | Taisho Pharmaceutical Co Ltd | Dihydroquinolinone derivatives |
| WO2011069063A2 (en) | 2009-12-04 | 2011-06-09 | Sunovion Pharmaceuticals, Inc. | Multicyclic compounds and methods of use thereof |
| WO2012054093A2 (en) | 2010-01-29 | 2012-04-26 | The Regents Of The University Of California | Acyl piperidine inhibitors of soluble epoxide hydrolase |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| SG186885A1 (en) | 2010-06-04 | 2013-02-28 | Albany Molecular Res Inc | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| WO2012113103A1 (en) | 2011-02-25 | 2012-08-30 | Helsinn Healthcare S.A. | Asymmetric ureas and medical uses thereof |
| TW201321353A (zh) | 2011-10-08 | 2013-06-01 | Novartis Ag | 胺基甲酸酯／尿素衍生物 |
| EP2789608A4 (en) | 2011-12-08 | 2015-07-01 | Taisho Pharmaceutical Co Ltd | PHENYLPYRROLDERIVAT |
| US20150045553A1 (en) | 2011-12-27 | 2015-02-12 | Taisho Pharmaceutical Co., Ltd | Phenyltriazole derivative |
| EP3383853B1 (en) * | 2015-12-01 | 2020-11-04 | Merck Sharp & Dohme Corp. | Homobispiperidinyl derivatives as liver x receptor (lxr) beta agonists for treating e.g. alzheimer's disease |
| WO2017162390A1 (en) | 2016-03-22 | 2017-09-28 | Helsinn Healthcare Sa | Benzenesulfonyl-asymmetric ureas and medical uses thereof |
| WO2017210545A1 (en) | 2016-06-02 | 2017-12-07 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| AU2017301767A1 (en) | 2016-07-29 | 2019-02-14 | Pgi Drug Discovery Llc | Compounds and compositions and uses thereof |
| HUE070203T2 (hu) | 2016-07-29 | 2025-05-28 | Sumitomo Pharma America Inc | Vegyületek és készítmények és alkalmazásaik |
| PL3571193T3 (pl) | 2017-01-23 | 2022-04-25 | Cadent Therapeutics, Inc. | Modulatory kanału potasowego |
| WO2018151861A1 (en) | 2017-02-16 | 2018-08-23 | Sunovion Pharamaceuticials Inc. | Methods of treating schizophrenia |
| AU2018312559B2 (en) | 2017-08-02 | 2022-06-02 | Pgi Drug Discovery Llc | Isochroman compounds and uses thereof |
| CA3091292A1 (en) | 2018-02-16 | 2019-08-22 | Sunovion Pharmaceuticals Inc. | Salts, crystal forms, and production methods thereof |
| AU2019255310B2 (en) | 2018-04-18 | 2022-11-24 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| CN120097995A (zh) | 2018-05-21 | 2025-06-06 | 星座制药公司 | 甲基修饰酶的调节剂、其组合物和用途 |
| BR112021007552A2 (pt) | 2018-10-22 | 2021-07-27 | Cadent Therapeutics, Inc. | formas cristalinas de moduladores de canal de potássio |
| CN111349609A (zh) * | 2018-12-21 | 2020-06-30 | 泰州医药城国科化物生物医药科技有限公司 | 一种无标记组胺受体h3的细胞筛选模型 |
| KR20210139376A (ko) | 2019-03-14 | 2021-11-22 | 선오비온 파마슈티컬스 인코포레이티드 | 이소크로마닐 화합물의 염, 및 이의 결정성 형태, 제조방법, 치료 용도 및 약제학적 조성물 |
| EP3969444A4 (en) * | 2019-05-13 | 2023-10-18 | The Regents of the University of California | COMPOSITIONS AND METHODS FOR THE TREATMENT OF NEUROLOGICAL DISEASES AND DISORDERS |
| ES2819309B2 (es) * | 2019-10-14 | 2021-11-17 | Fundacion Para La Investigacion Biomedica Del Hospital Univ De La Princesa | Compuestos agonistas nicotínicos y antioxidantes para el tratamiento de enfermedades neurodegenerativas |
| EP4135690A1 (en) | 2020-04-14 | 2023-02-22 | Sunovion Pharmaceuticals Inc. | (s)-(4,5-dihydro-7h-thieno[2,3-c]pyran-7-yl)-n-methylmethanamine for treating neurological and psychiatric disorders |
| CN113549006B (zh) * | 2020-04-26 | 2023-07-21 | 江苏恩华药业股份有限公司 | 一种酰胺衍生物及其应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0343307A1 (en) * | 1988-05-26 | 1989-11-29 | Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. | 4-Piperidinealkanamine derivatives |
| DE19614204A1 (de) * | 1996-04-10 | 1997-10-16 | Thomae Gmbh Dr K | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| EP1434765B1 (en) * | 2001-09-14 | 2009-12-02 | High Point Pharmaceuticals, LLC | Substituted piperidines with selective binding to histamine h3-receptor |
| US6673829B2 (en) * | 2001-09-14 | 2004-01-06 | Novo Nordisk A/S | Aminoazetidine,-pyrrolidine and -piperidine derivatives |
| US7064135B2 (en) * | 2001-10-12 | 2006-06-20 | Novo Nordisk Inc. | Substituted piperidines |
| JP2006512404A (ja) * | 2002-10-22 | 2006-04-13 | グラクソ グループ リミテッド | Ｈ３受容体リガンドとしてのアリールオキシアルキルアミン誘導体 |
| US7332508B2 (en) * | 2002-12-18 | 2008-02-19 | Novo Nordisk A/S | Substituted homopiperidine, piperidine or pyrrolidine derivatives |
| WO2005028438A1 (ja) * | 2003-09-22 | 2005-03-31 | Banyu Pharmaceutical Co., Ltd. | 新規ピペリジン誘導体 |
-
2004
- 2004-08-02 SE SE0401971A patent/SE0401971D0/xx unknown
-
2005
- 2005-07-27 WO PCT/SE2005/001189 patent/WO2006014136A1/en not_active Ceased
- 2005-07-27 CA CA002576112A patent/CA2576112A1/en not_active Abandoned
- 2005-07-27 EP EP05761797A patent/EP1781613A1/en not_active Withdrawn
- 2005-07-27 AU AU2005267932A patent/AU2005267932A1/en not_active Abandoned
- 2005-07-27 CN CNA2005800262732A patent/CN1993325A/zh active Pending
- 2005-07-27 MX MX2007001226A patent/MX2007001226A/es not_active Application Discontinuation
- 2005-07-27 RU RU2007105970/04A patent/RU2007105970A/ru not_active Application Discontinuation
- 2005-07-27 BR BRPI0514035-8A patent/BRPI0514035A/pt not_active Application Discontinuation
- 2005-07-27 JP JP2007524768A patent/JP2008508353A/ja not_active Abandoned
- 2005-07-27 KR KR1020077002643A patent/KR20070043998A/ko not_active Withdrawn
- 2005-07-27 US US11/572,967 patent/US20080064706A1/en not_active Abandoned
-
2007
- 2007-01-04 IL IL180548A patent/IL180548A0/en unknown
- 2007-01-24 ZA ZA200700683A patent/ZA200700683B/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015522606A (ja) * | 2012-07-20 | 2015-08-06 | ノバルティス アーゲー | カルバメート／尿素誘導体 |
| JP2017507116A (ja) * | 2014-03-07 | 2017-03-16 | ヘルシン ヘルスケア ソシエテ アノニム | ｐ−置換非対称尿素及びその医薬的使用 |
| JP2017520530A (ja) * | 2014-05-19 | 2017-07-27 | メリアル インコーポレイテッド | 駆虫性化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007001226A (es) | 2007-03-23 |
| SE0401971D0 (sv) | 2004-08-02 |
| EP1781613A1 (en) | 2007-05-09 |
| KR20070043998A (ko) | 2007-04-26 |
| US20080064706A1 (en) | 2008-03-13 |
| ZA200700683B (en) | 2008-08-27 |
| CN1993325A (zh) | 2007-07-04 |
| AU2005267932A1 (en) | 2006-02-09 |
| CA2576112A1 (en) | 2006-02-09 |
| BRPI0514035A (pt) | 2008-05-27 |
| IL180548A0 (en) | 2007-06-03 |
| RU2007105970A (ru) | 2008-09-10 |
| WO2006014136A1 (en) | 2006-02-09 |
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