JP2005528363A - 新規アダマンタン誘導体 - Google Patents
新規アダマンタン誘導体 Download PDFInfo
- Publication number
- JP2005528363A JP2005528363A JP2003578334A JP2003578334A JP2005528363A JP 2005528363 A JP2005528363 A JP 2005528363A JP 2003578334 A JP2003578334 A JP 2003578334A JP 2003578334 A JP2003578334 A JP 2003578334A JP 2005528363 A JP2005528363 A JP 2005528363A
- Authority
- JP
- Japan
- Prior art keywords
- amino
- adamantyl
- acetamide
- quinolin
- ethyl
- 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- Withdrawn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
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title description 2
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 168
- 238000000034 method Methods 0.000 claims abstract description 51
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- -1 phenoxy, benzodioxolyl Chemical group 0.000 claims description 376
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 233
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 99
- 229910052757 nitrogen Inorganic materials 0.000 claims description 82
- 125000001424 substituent group Chemical group 0.000 claims description 62
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 46
- KTWVNLHVTKIKRE-UHFFFAOYSA-N 2-(1-adamantyl)-n-(2-chloroquinolin-5-yl)acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(Cl)=CC=C21 KTWVNLHVTKIKRE-UHFFFAOYSA-N 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000004122 cyclic group Chemical group 0.000 claims description 29
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- XXXLAMSEUQFRFP-UHFFFAOYSA-N 2-(1-adamantyl)-n-(2-chloro-6-methylquinolin-5-yl)acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C=CC(Cl)=NC2=CC=C1C XXXLAMSEUQFRFP-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Chemical group 0.000 claims description 16
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000003386 piperidinyl group Chemical group 0.000 claims description 13
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 239000011593 sulfur Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- NBKPACNTJSTPHM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-(2-aminoethylamino)quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCN)=CC=C21 NBKPACNTJSTPHM-UHFFFAOYSA-N 0.000 claims description 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- JUBKNCKCWVABQL-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-[benzyl(2-hydroxyethyl)amino]ethoxy]quinolin-5-yl]acetamide Chemical compound C=1C=C2C(NC(=O)CC34CC5CC(CC(C5)C3)C4)=CC=CC2=NC=1OCCN(CCO)CC1=CC=CC=C1 JUBKNCKCWVABQL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 6
- BVFONFUUWORSPO-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 BVFONFUUWORSPO-UHFFFAOYSA-N 0.000 claims description 5
- PFYCQNRCQTTZPU-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[3-(pyridin-2-ylmethylamino)propylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC(C1=CC=2)=CC=CC1=NC=2NCCCNCC1=CC=CC=N1 PFYCQNRCQTTZPU-UHFFFAOYSA-N 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- PTCLYUFSTQHWEQ-UHFFFAOYSA-N 2-(1-adamantyl)-n-(6-methylquinolin-5-yl)acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C=CC=NC2=CC=C1C PTCLYUFSTQHWEQ-UHFFFAOYSA-N 0.000 claims description 4
- TYBABKZVIJDHPE-SYWMPMGTSA-N 2-(1-adamantyl)-n-[2-[(3r)-3-aminopyrrolidin-1-yl]-6-methylquinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(C)=CC=C2N=C1N1CC[C@@H](N)C1 TYBABKZVIJDHPE-SYWMPMGTSA-N 0.000 claims description 4
- TYBABKZVIJDHPE-BGWMMPTCSA-N 2-(1-adamantyl)-n-[2-[(3s)-3-aminopyrrolidin-1-yl]-6-methylquinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(C)=CC=C2N=C1N1CC[C@H](N)C1 TYBABKZVIJDHPE-BGWMMPTCSA-N 0.000 claims description 4
- GBDKFWNYRMVKTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(3-hydroxypropylamino)ethyl]-6-methylquinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C=CC(CCNCCCO)=NC2=CC=C1C GBDKFWNYRMVKTM-UHFFFAOYSA-N 0.000 claims description 4
- UFFYMWHKSLTBJU-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[3-(3-hydroxypropylamino)propyl]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(CCCNCCCO)=CC=C21 UFFYMWHKSLTBJU-UHFFFAOYSA-N 0.000 claims description 4
- LINZLQORNIIEFJ-ZCIMRUIVSA-N 2-(1-adamantyl)-n-[2-[3-[[(2r)-1-hydroxypropan-2-yl]amino]propyl]quinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(CCCN[C@@H](CO)C)=CC=C21 LINZLQORNIIEFJ-ZCIMRUIVSA-N 0.000 claims description 4
- UIPNEKXUHNHYTK-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[4-(2-hydroxyethylamino)piperidin-1-yl]-6-methylquinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(C)=CC=C2N=C1N1CCC(NCCO)CC1 UIPNEKXUHNHYTK-UHFFFAOYSA-N 0.000 claims description 4
- BBHSBBLOPRDLRE-UCADOFJPSA-N 2-(1-adamantyl)-n-[6-chloro-2-[(3r)-3,4-dihydroxybutyl]quinolin-5-yl]acetamide;hydrochloride Chemical compound Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(Cl)C=CC2=NC(CC[C@@H](O)CO)=CC=C21 BBHSBBLOPRDLRE-UCADOFJPSA-N 0.000 claims description 4
- AOZWTEBEDNDWNP-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-chloro-2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(Cl)C=CC2=NC(NCCNCCO)=CC=C21 AOZWTEBEDNDWNP-UHFFFAOYSA-N 0.000 claims description 4
- JPGQURIKAYHUIV-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-chloro-2-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]quinolin-5-yl]acetamide Chemical compound C1CN(CCO)CCN1CC1=CC=C(C(NC(=O)CC23CC4CC(CC(C4)C2)C3)=C(Cl)C=C2)C2=N1 JPGQURIKAYHUIV-UHFFFAOYSA-N 0.000 claims description 4
- KGXVQMGWQNAODV-RRKYIATISA-N 2-(1-adamantyl)-n-[6-methyl-2-[(3s)-3-(methylamino)pyrrolidin-1-yl]quinolin-5-yl]acetamide Chemical compound C1[C@@H](NC)CCN1C1=CC=C(C(NC(=O)CC23CC4CC(CC(C4)C2)C3)=C(C)C=C2)C2=N1 KGXVQMGWQNAODV-RRKYIATISA-N 0.000 claims description 4
- WNIYOTXEDARBCM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-methyl-2-[3-(methylamino)propylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(C)C=CC2=NC(NCCCNC)=CC=C21 WNIYOTXEDARBCM-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- NPBWESFRMQNWEU-UHFFFAOYSA-N n-(1-adamantylmethyl)-6-chloro-2-(piperazin-1-ylmethyl)quinoline-5-carboxamide Chemical compound C1=CC2=C(C(=O)NCC34CC5CC(CC(C5)C3)C4)C(Cl)=CC=C2N=C1CN1CCNCC1 NPBWESFRMQNWEU-UHFFFAOYSA-N 0.000 claims description 4
- XCMDISWXPTVYAX-UHFFFAOYSA-N n-(1-adamantylmethyl)-6-chloro-2-[3-(methylamino)propyl]quinoline-5-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=C(Cl)C=CC2=NC(CCCNC)=CC=C21 XCMDISWXPTVYAX-UHFFFAOYSA-N 0.000 claims description 4
- JCIBXRTYUXRIJK-UHFFFAOYSA-N n-(1-adamantylmethyl)-8-[3-(methylamino)propyl]quinoline-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1C(C2)CC(C3)CC2CC13CNC(=O)C1=C2C=CC=C(CCCNC)C2=NC=C1 JCIBXRTYUXRIJK-UHFFFAOYSA-N 0.000 claims description 4
- 230000000414 obstructive effect Effects 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 208000023504 respiratory system disease Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- QZXIYUSPLXLYHI-UHFFFAOYSA-N 2-(1-adamantyl)-n-(4-methylquinolin-5-yl)acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C(C)=CC=NC2=CC=C1 QZXIYUSPLXLYHI-UHFFFAOYSA-N 0.000 claims description 3
- NJQMIMWTOJAPTF-UHFFFAOYSA-N 2-(1-adamantyl)-n-(6-chloro-2-piperazin-1-ylquinolin-5-yl)acetamide Chemical compound C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(Cl)=CC=C2N=C1N1CCNCC1 NJQMIMWTOJAPTF-UHFFFAOYSA-N 0.000 claims description 3
- PXSBXWOZJZYINI-UHFFFAOYSA-N 2-(1-adamantyl)-n-(6-chloroquinolin-5-yl)acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C=CC=NC2=CC=C1Cl PXSBXWOZJZYINI-UHFFFAOYSA-N 0.000 claims description 3
- JYHRIELTTAQQGU-UHFFFAOYSA-N 2-(1-adamantyl)-n-(6-methyl-2-piperazin-1-ylquinolin-5-yl)acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(C)=CC=C2N=C1N1CCNCC1 JYHRIELTTAQQGU-UHFFFAOYSA-N 0.000 claims description 3
- OXPUJUQYTJKGOT-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-(2-hydroxyethylamino)quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCO)=CC=C21 OXPUJUQYTJKGOT-UHFFFAOYSA-N 0.000 claims description 3
- HQMHYDVWFMIEES-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-(3-aminopropylamino)quinolin-5-yl]acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCCN)=CC=C21 HQMHYDVWFMIEES-UHFFFAOYSA-N 0.000 claims description 3
- NUVXHPFJQVXNAT-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-(3-hydroxypropylamino)-6-methylquinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C=CC(NCCCO)=NC2=CC=C1C NUVXHPFJQVXNAT-UHFFFAOYSA-N 0.000 claims description 3
- RSAYOFQTMTVUIZ-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-(3-hydroxypropylamino)quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCCO)=CC=C21 RSAYOFQTMTVUIZ-UHFFFAOYSA-N 0.000 claims description 3
- RSVACYUBPNLTGQ-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-(4-aminopiperidin-1-yl)-6-methylquinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(C)=CC=C2N=C1N1CCC(N)CC1 RSVACYUBPNLTGQ-UHFFFAOYSA-N 0.000 claims description 3
- LXTJRVHYFNOBBA-MENVUMQLSA-N 2-(1-adamantyl)-n-[2-[(3s)-3-(ethylamino)pyrrolidin-1-yl]-6-methylquinolin-5-yl]acetamide Chemical compound C1[C@@H](NCC)CCN1C1=CC=C(C(NC(=O)CC23CC4CC(CC(C4)C2)C3)=C(C)C=C2)C2=N1 LXTJRVHYFNOBBA-MENVUMQLSA-N 0.000 claims description 3
- CZUUERWGNWMLKD-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethoxy]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(OCCNCCO)=CC=C21 CZUUERWGNWMLKD-UHFFFAOYSA-N 0.000 claims description 3
- VJQBZRYJGOSFAX-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)propylamino]-6-methylquinolin-5-yl]acetamide;hydrochloride Chemical compound Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(C)C=CC2=NC(NCC(C)NCCO)=CC=C21 VJQBZRYJGOSFAX-UHFFFAOYSA-N 0.000 claims description 3
- KGSCHINOXMIVEF-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-[bis(2-hydroxyethyl)amino]ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCN(CCO)CCO)=CC=C21 KGSCHINOXMIVEF-UHFFFAOYSA-N 0.000 claims description 3
- CQEKXTYQPVDQHS-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-6-methylquinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(C)=CC=C2N=C1N1CCN(CCO)CC1 CQEKXTYQPVDQHS-UHFFFAOYSA-N 0.000 claims description 3
- HIJJDGQVWGBNJJ-LJQCHSNASA-N 2-(1-adamantyl)-n-[2-[[(2r)-2-hydroxypropyl]amino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NC[C@H](O)C)=CC=C21 HIJJDGQVWGBNJJ-LJQCHSNASA-N 0.000 claims description 3
- UAXZEJUZXIDQOT-JNYXMARXSA-N 2-(1-adamantyl)-n-[2-[[(2s)-2,3-dihydroxypropyl]amino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NC[C@H](O)CO)=CC=C21 UAXZEJUZXIDQOT-JNYXMARXSA-N 0.000 claims description 3
- HIJJDGQVWGBNJJ-KSKOPSKJSA-N 2-(1-adamantyl)-n-[2-[[(2s)-2-hydroxypropyl]amino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NC[C@@H](O)C)=CC=C21 HIJJDGQVWGBNJJ-KSKOPSKJSA-N 0.000 claims description 3
- ZWRUQQRURZZSSF-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[bis(2-hydroxyethyl)amino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(N(CCO)CCO)=CC=C21 ZWRUQQRURZZSSF-UHFFFAOYSA-N 0.000 claims description 3
- HESTWRCAQUNSHI-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-chloro-2-(piperazin-1-ylmethyl)quinolin-5-yl]acetamide Chemical compound C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(Cl)=CC=C2N=C1CN1CCNCC1 HESTWRCAQUNSHI-UHFFFAOYSA-N 0.000 claims description 3
- SAZSEECRIWPFFL-NFRJURENSA-N 2-(1-adamantyl)-n-[6-chloro-2-[(3r)-3-hydroxy-4-(methylamino)butyl]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(Cl)C=CC2=NC(CC[C@@H](O)CNC)=CC=C21 SAZSEECRIWPFFL-NFRJURENSA-N 0.000 claims description 3
- JLSRHBJQRNMNSQ-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-chloro-2-[2-(methylamino)ethylamino]quinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(Cl)C=CC2=NC(NCCNC)=CC=C21 JLSRHBJQRNMNSQ-UHFFFAOYSA-N 0.000 claims description 3
- MFCGNMVVXIBTFW-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-chloro-2-[3-(2-hydroxyethylamino)propylamino]quinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(Cl)C=CC2=NC(NCCCNCCO)=CC=C21 MFCGNMVVXIBTFW-UHFFFAOYSA-N 0.000 claims description 3
- HFAXHQKJVNSNAI-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-chloro-2-[3-(3-hydroxypropylamino)propyl]quinolin-5-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(Cl)C=CC2=NC(CCCNCCCO)=CC=C21 HFAXHQKJVNSNAI-UHFFFAOYSA-N 0.000 claims description 3
- DRBZCWLRGVNLIG-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-chloro-2-[[2-(2-hydroxyethylamino)ethylamino]methyl]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(Cl)C=CC2=NC(CNCCNCCO)=CC=C21 DRBZCWLRGVNLIG-UHFFFAOYSA-N 0.000 claims description 3
- VWNCUUKPDHPDKV-UHFFFAOYSA-N 2-(1-adamantyl)-n-[6-chloro-2-[[2-(methylamino)ethylamino]methyl]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C(Cl)C=CC2=NC(CNCCNC)=CC=C21 VWNCUUKPDHPDKV-UHFFFAOYSA-N 0.000 claims description 3
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- 206010039083 rhinitis Diseases 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- QWQQJKYSTUZVDK-UHFFFAOYSA-N tert-butyl n-(2-aminopropyl)-n-methylcarbamate Chemical compound CC(N)CN(C)C(=O)OC(C)(C)C QWQQJKYSTUZVDK-UHFFFAOYSA-N 0.000 description 1
- VAPZHUNBWITAGJ-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)-n-[2-[(2-methylpropan-2-yl)oxycarbonyl-(5-nitroquinolin-8-yl)amino]ethyl]carbamate Chemical compound C1=CN=C2C(N(C(=O)OC(C)(C)C)CCN(CCO)C(=O)OC(C)(C)C)=CC=C([N+]([O-])=O)C2=C1 VAPZHUNBWITAGJ-UHFFFAOYSA-N 0.000 description 1
- PNQYAMWGTGWJDW-UHFFFAOYSA-N tert-butyl n-(3-aminopropyl)-n-methylcarbamate Chemical compound NCCCN(C)C(=O)OC(C)(C)C PNQYAMWGTGWJDW-UHFFFAOYSA-N 0.000 description 1
- PCFOVOGBWUYJBW-UHFFFAOYSA-N tert-butyl n-(3-hydroxypropyl)-n-prop-2-ynylcarbamate Chemical compound CC(C)(C)OC(=O)N(CC#C)CCCO PCFOVOGBWUYJBW-UHFFFAOYSA-N 0.000 description 1
- DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 1
- KRFZSBDZKCTDTP-UHFFFAOYSA-N tert-butyl n-[1-[5-[[2-(1-adamantyl)acetyl]amino]-6-methylquinolin-2-yl]piperidin-4-yl]carbamate Chemical compound C1=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C(C)=CC=C2N=C1N1CCC(NC(=O)OC(C)(C)C)CC1 KRFZSBDZKCTDTP-UHFFFAOYSA-N 0.000 description 1
- WOVNSTICAFZVLK-UHFFFAOYSA-N tert-butyl n-[3-[5-[[2-(1-adamantyl)acetyl]amino]quinolin-2-yl]propyl]-n-(3-hydroxypropyl)carbamate Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(CCCN(CCCO)C(=O)OC(C)(C)C)=CC=C21 WOVNSTICAFZVLK-UHFFFAOYSA-N 0.000 description 1
- CDWFUHGLHLITRC-GEAKPONUSA-N tert-butyl n-[3-[5-[[2-(1-adamantyl)acetyl]amino]quinolin-2-yl]propyl]-n-[(2r)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]carbamate Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(CCCN([C@@H](CO[Si](C)(C)C(C)(C)C)C)C(=O)OC(C)(C)C)=CC=C21 CDWFUHGLHLITRC-GEAKPONUSA-N 0.000 description 1
- GMUSPUCUSDKCOJ-UHFFFAOYSA-N tert-butyl n-[5-[[2-(1-adamantyl)acetyl]amino]quinolin-8-yl]-n-[2-[2-hydroxyethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]carbamate Chemical compound C12=CC=CN=C2C(N(C(=O)OC(C)(C)C)CCN(CCO)C(=O)OC(C)(C)C)=CC=C1NC(=O)CC1(C2)CC(C3)CC2CC3C1 GMUSPUCUSDKCOJ-UHFFFAOYSA-N 0.000 description 1
- QUFBSMRRKUFHOO-UHFFFAOYSA-N tert-butyl n-ethyl-n-prop-2-enylcarbamate Chemical compound C=CCN(CC)C(=O)OC(C)(C)C QUFBSMRRKUFHOO-UHFFFAOYSA-N 0.000 description 1
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
- YQSZKHAAIWDZHX-PFEQFJNWSA-N tert-butyl-[(2r)-2-[tert-butyl(dimethyl)silyl]oxybut-3-enoxy]-dimethylsilane;tert-butyl-chloro-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)Cl.CC(C)(C)[Si](C)(C)OC[C@@H](C=C)O[Si](C)(C)C(C)(C)C YQSZKHAAIWDZHX-PFEQFJNWSA-N 0.000 description 1
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- WIOADUFWOUUQCV-UHFFFAOYSA-N triphenylphosphanium dichloride Chemical compound [Cl-].[Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 WIOADUFWOUUQCV-UHFFFAOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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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
- 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
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- Health & Medical Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0200920A SE0200920D0 (sv) | 2002-03-25 | 2002-03-25 | Novel compounds |
| PCT/SE2003/000481 WO2003080579A1 (en) | 2002-03-25 | 2003-03-24 | Novel adamantane derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005528363A true JP2005528363A (ja) | 2005-09-22 |
| JP2005528363A5 JP2005528363A5 (https=) | 2006-05-18 |
Family
ID=20287392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003578334A Withdrawn JP2005528363A (ja) | 2002-03-25 | 2003-03-24 | 新規アダマンタン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20050090524A1 (https=) |
| EP (1) | EP1490341A1 (https=) |
| JP (1) | JP2005528363A (https=) |
| AR (1) | AR039124A1 (https=) |
| AU (1) | AU2003216013A1 (https=) |
| SE (1) | SE0200920D0 (https=) |
| TW (1) | TW200306800A (https=) |
| WO (1) | WO2003080579A1 (https=) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007501782A (ja) * | 2003-08-08 | 2007-02-01 | アストラゼネカ・アクチエボラーグ | P2x7受容体アンタゴニストとしての2−アダマンチル誘導体 |
| JP2009530304A (ja) * | 2006-03-16 | 2009-08-27 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロへテロアリール化合物およびその使用 |
| JP2009530302A (ja) * | 2006-03-16 | 2009-08-27 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロへテロアリール化合物およびその使用 |
| JP2009541206A (ja) * | 2006-03-16 | 2009-11-26 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロへテロアリール化合物およびその使用 |
| JP2010511653A (ja) * | 2006-12-07 | 2010-04-15 | エフ.ホフマン−ラ ロシュ アーゲー | 5−ht(5a)受容体アンタゴニストとしての2−アミノキノリン |
| JP2011513352A (ja) * | 2008-03-07 | 2011-04-28 | エフ.ホフマン−ラ ロシュ アーゲー | 5−ht(5a)受容体アンタゴニストとしての2−アミノキノリン誘導体 |
| JP2011514898A (ja) * | 2008-03-07 | 2011-05-12 | エフ.ホフマン−ラ ロシュ アーゲー | 2−アミノキノリン誘導体 |
| JP2017520538A (ja) * | 2014-06-05 | 2017-07-27 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 新規キノリン誘導体及び神経変性疾患におけるそれらの使用 |
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| TWI258462B (en) | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
| GB0013737D0 (en) | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
| SE0103836D0 (sv) | 2001-11-16 | 2001-11-16 | Astrazeneca Ab | Novel compounds |
| SE0200920D0 (sv) * | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
| SE0300480D0 (sv) * | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
| EP1644042A1 (en) * | 2003-05-29 | 2006-04-12 | AstraZeneca AB | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
| WO2004105797A1 (en) * | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
| TW200507829A (en) * | 2003-05-29 | 2005-03-01 | Astrazeneca Ab | New combination |
| GB0312609D0 (en) * | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| SE0302488D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | New combination |
| SA05260265A (ar) * | 2004-08-30 | 2005-12-03 | استرازينيكا ايه بي | مركبات جديدة |
| EP2287301A3 (en) * | 2004-08-31 | 2011-11-02 | Sylentis S.A.U. | Methods and compositions to inhibit P2X7 receptor expression |
| SE0402925D0 (sv) * | 2004-11-30 | 2004-11-30 | Astrazeneca Ab | Novel Compounds |
| US7297700B2 (en) * | 2005-03-24 | 2007-11-20 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
| GB0506133D0 (en) * | 2005-03-24 | 2005-05-04 | Sterix Ltd | Compound |
| WO2006110516A1 (en) * | 2005-04-11 | 2006-10-19 | Abbott Laboratories | Acylhydrazide p2x7 antagonists and uses thereof |
| WO2006136791A1 (en) * | 2005-06-21 | 2006-12-28 | Astrazeneca Ab | Polymorphisms and haplotypes in p2x7 gene and their use in determining susceptibility for atherosclerosis-mediated diseases |
| WO2007028022A2 (en) * | 2005-09-01 | 2007-03-08 | Renovis, Inc. | Novel compounds as p2x7 modulators and uses thereof |
| JP2009541205A (ja) * | 2006-03-16 | 2009-11-26 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロへテロアリール化合物およびその使用 |
| EA201300152A1 (ru) | 2006-11-27 | 2013-07-30 | Х. Лундбекк А/С | Гетероариламидные производные |
| BRPI0809106A2 (pt) | 2007-03-22 | 2014-08-26 | Astrazeneca Ab | Derivados de quinolina para o tratamento de doenças inflamatórias |
| BRPI0809567A2 (pt) | 2007-04-10 | 2014-09-23 | Lundbeck & Co As H | Composto, composição farmacêutica, método para modular a atividade de um receptor de p2x7, para tratar uma condição responsiva à modulação do receptor de p2x7 em um paciente, para inibir a morte de células do gânglio retinal em um paciente, e para determinar a presença ou ausência do receptor de p2x7 em uma amostra, preparação farmacêutica acondiciaonada, e, uso de um composto |
| US8106073B2 (en) | 2007-11-30 | 2012-01-31 | Astrazeneca Ab | Quinoline derivatives 057 |
| CN102046240B (zh) | 2008-03-25 | 2014-06-25 | 阿费克蒂斯药品公司 | 新的p2x7r拮抗剂及其应用 |
| WO2010118921A1 (en) | 2009-04-14 | 2010-10-21 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| EP2569281A1 (en) | 2010-05-14 | 2013-03-20 | Affectis Pharmaceuticals AG | Novel methods for the preparation of p2x7r antagonists |
| CN102464631B (zh) * | 2010-11-08 | 2016-08-10 | 中国科学院上海药物研究所 | 哌嗪取代的1,3-二取代脲类化合物及哌嗪取代的酰胺类化合物及其制备方法和用途 |
| WO2012110190A1 (en) | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163456A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| CN103687860B (zh) | 2011-07-22 | 2016-06-08 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的杂环酰胺衍生物 |
| EA024204B1 (ru) | 2012-01-20 | 2016-08-31 | Актелион Фармасьютиклз Лтд. | Производные гетероциклических амидов в качестве антагонистов p2xрецептора |
| AR093921A1 (es) | 2012-12-12 | 2015-06-24 | Actelion Pharmaceuticals Ltd | Derivados de indol carboxamida como antagonistas del receptor p2x7 |
| KR102232744B1 (ko) | 2012-12-18 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | P2x7 수용체 길항제로서의 인돌 카르복사미드 유도체 |
| KR102222220B1 (ko) | 2013-01-22 | 2021-03-03 | 이도르시아 파마슈티컬스 리미티드 | P2x7 수용체 길항제로서의 헤테로시클릭 아미드 유도체 |
| ES2616883T3 (es) | 2013-01-22 | 2017-06-14 | Actelion Pharmaceuticals Ltd. | Derivados amida heterocíclicos como antagonistas del receptor P2X7 |
| KR102035463B1 (ko) * | 2018-02-14 | 2019-11-26 | 연세대학교 산학협력단 | 암 줄기세포의 치료용 약학 조성물 |
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| PL181782B1 (pl) * | 1993-08-10 | 2001-09-28 | Black James Foundation | Nowe zwiazki i sposób wytwarzania nowych zwiazków PL |
| EP0952832B1 (en) * | 1996-05-20 | 2008-08-27 | Darwin Discovery Limited | Quinoline carboxamides as tnf inhibitors and as pde-iv inhibitors |
| SE9704545D0 (sv) * | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| SE9704544D0 (sv) * | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| CN1147483C (zh) * | 1999-04-09 | 2004-04-28 | 阿斯特拉曾尼卡有限公司 | 金刚烷衍生物 |
| SE9904505D0 (sv) * | 1999-12-09 | 1999-12-09 | Astra Pharma Prod | Novel compounds |
| TWI258462B (en) * | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
| GB0013737D0 (en) * | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
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| WO2003042190A1 (en) * | 2001-11-12 | 2003-05-22 | Pfizer Products Inc. | N-alkyl-adamantyl derivatives as p2x7-receptor antagonists |
| SE0103836D0 (sv) * | 2001-11-16 | 2001-11-16 | Astrazeneca Ab | Novel compounds |
| US6908939B2 (en) * | 2001-12-21 | 2005-06-21 | Galderma Research & Development S.N.C. | Biaromatic ligand activators of PPARγ receptors |
| SE0200920D0 (sv) * | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
| SE0300445D0 (sv) * | 2003-02-18 | 2003-02-18 | Astrazeneca Ab | New combination |
| SE0300480D0 (sv) * | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
| WO2004105797A1 (en) * | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
| TW200507829A (en) * | 2003-05-29 | 2005-03-01 | Astrazeneca Ab | New combination |
| EP1644042A1 (en) * | 2003-05-29 | 2006-04-12 | AstraZeneca AB | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
| SE0302192D0 (sv) * | 2003-08-08 | 2003-08-08 | Astrazeneca Ab | Novel compounds |
| SE0302488D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | New combination |
-
2002
- 2002-03-25 SE SE0200920A patent/SE0200920D0/xx unknown
-
2003
- 2003-03-13 TW TW092105477A patent/TW200306800A/zh unknown
- 2003-03-24 EP EP03745060A patent/EP1490341A1/en not_active Withdrawn
- 2003-03-24 US US10/505,789 patent/US20050090524A1/en not_active Abandoned
- 2003-03-24 JP JP2003578334A patent/JP2005528363A/ja not_active Withdrawn
- 2003-03-24 AU AU2003216013A patent/AU2003216013A1/en not_active Abandoned
- 2003-03-24 WO PCT/SE2003/000481 patent/WO2003080579A1/en not_active Ceased
- 2003-03-25 AR ARP030101025A patent/AR039124A1/es not_active Application Discontinuation
-
2008
- 2008-02-29 US US12/040,462 patent/US20090018133A1/en not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007501782A (ja) * | 2003-08-08 | 2007-02-01 | アストラゼネカ・アクチエボラーグ | P2x7受容体アンタゴニストとしての2−アダマンチル誘導体 |
| JP2009530304A (ja) * | 2006-03-16 | 2009-08-27 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロへテロアリール化合物およびその使用 |
| JP2009530302A (ja) * | 2006-03-16 | 2009-08-27 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロへテロアリール化合物およびその使用 |
| JP2009541206A (ja) * | 2006-03-16 | 2009-11-26 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロへテロアリール化合物およびその使用 |
| JP2010511653A (ja) * | 2006-12-07 | 2010-04-15 | エフ.ホフマン−ラ ロシュ アーゲー | 5−ht(5a)受容体アンタゴニストとしての2−アミノキノリン |
| JP2011513352A (ja) * | 2008-03-07 | 2011-04-28 | エフ.ホフマン−ラ ロシュ アーゲー | 5−ht(5a)受容体アンタゴニストとしての2−アミノキノリン誘導体 |
| JP2011514898A (ja) * | 2008-03-07 | 2011-05-12 | エフ.ホフマン−ラ ロシュ アーゲー | 2−アミノキノリン誘導体 |
| JP2017520538A (ja) * | 2014-06-05 | 2017-07-27 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 新規キノリン誘導体及び神経変性疾患におけるそれらの使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1490341A1 (en) | 2004-12-29 |
| SE0200920D0 (sv) | 2002-03-25 |
| AR039124A1 (es) | 2005-02-09 |
| AU2003216013A1 (en) | 2003-10-08 |
| WO2003080579A1 (en) | 2003-10-02 |
| US20090018133A1 (en) | 2009-01-15 |
| TW200306800A (en) | 2003-12-01 |
| US20050090524A1 (en) | 2005-04-28 |
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