JP2016506935A - イミダゾピリジン化合物及びその使用 - Google Patents
イミダゾピリジン化合物及びその使用 Download PDFInfo
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- JP2016506935A JP2016506935A JP2015555508A JP2015555508A JP2016506935A JP 2016506935 A JP2016506935 A JP 2016506935A JP 2015555508 A JP2015555508 A JP 2015555508A JP 2015555508 A JP2015555508 A JP 2015555508A JP 2016506935 A JP2016506935 A JP 2016506935A
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- Prior art keywords
- compound
- methyl
- salt
- animal
- salt according
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- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 193
- 150000003839 salts Chemical class 0.000 claims abstract description 128
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000003814 drug Substances 0.000 claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 241001465754 Metazoa Species 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 208000035475 disorder Diseases 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 24
- 230000000694 effects Effects 0.000 claims description 21
- 102100040460 P2X purinoceptor 3 Human genes 0.000 claims description 20
- 101710189970 P2X purinoceptor 3 Proteins 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 15
- 208000002193 Pain Diseases 0.000 claims description 13
- 102100040479 P2X purinoceptor 2 Human genes 0.000 claims description 12
- 101710189968 P2X purinoceptor 2 Proteins 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 230000036407 pain Effects 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 208000028394 ureteral disease Diseases 0.000 claims description 6
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 3
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 208000020629 overactive bladder Diseases 0.000 claims description 3
- -1 for example Chemical class 0.000 abstract description 58
- 150000005232 imidazopyridines Chemical class 0.000 abstract description 7
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- 239000000543 intermediate Substances 0.000 abstract description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
- 239000000203 mixture Substances 0.000 description 142
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
- 235000019439 ethyl acetate Nutrition 0.000 description 62
- 230000002829 reductive effect Effects 0.000 description 57
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
- 238000002360 preparation method Methods 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
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- 238000005481 NMR spectroscopy Methods 0.000 description 37
- 239000007787 solid Substances 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
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- 239000000706 filtrate Substances 0.000 description 17
- 238000007792 addition Methods 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000002207 metabolite Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 239000005909 Kieselgur Substances 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229960005419 nitrogen Drugs 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- 238000013459 approach Methods 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 208000004454 Hyperalgesia Diseases 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 206010065390 Inflammatory pain Diseases 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 210000002683 foot Anatomy 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 5
- 0 CCc1c(-c2c(*)cc(C(N(*)*)=O)c(*)c2)nc2[n]1cc(*)c(*)c2 Chemical compound CCc1c(-c2c(*)cc(C(N(*)*)=O)c(*)c2)nc2[n]1cc(*)c(*)c2 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000002648 combination therapy Methods 0.000 description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 5
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000004808 supercritical fluid chromatography Methods 0.000 description 5
- JBOKXNRQCWCOJH-VIFPVBQESA-N tert-butyl (2s)-2-ethynylmorpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCO[C@@H](C#C)C1 JBOKXNRQCWCOJH-VIFPVBQESA-N 0.000 description 5
- OUEOPPRNCAYIRR-UHFFFAOYSA-N 1-diazonio-1-dimethoxyphosphoryloxyprop-1-en-2-olate Chemical compound COP(=O)(OC)OC([N+]#N)=C(C)[O-] OUEOPPRNCAYIRR-UHFFFAOYSA-N 0.000 description 4
- MZHDMPFPVYDUQZ-UHFFFAOYSA-N 3,5-difluoro-4-formyl-n-methylbenzamide Chemical compound CNC(=O)C1=CC(F)=C(C=O)C(F)=C1 MZHDMPFPVYDUQZ-UHFFFAOYSA-N 0.000 description 4
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
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- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 4
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- 125000002346 iodo group Chemical group I* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- KZCMSWUXFXYAIJ-UHFFFAOYSA-N methyl 3,5-difluoro-4-formylbenzoate Chemical compound COC(=O)C1=CC(F)=C(C=O)C(F)=C1 KZCMSWUXFXYAIJ-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- SZJCFXLXJXPMHQ-UHFFFAOYSA-N n,3-dimethyl-4-(7-methylimidazo[1,2-a]pyridin-2-yl)benzamide Chemical compound CC1=CC(C(=O)NC)=CC=C1C1=CN(C=CC(C)=C2)C2=N1 SZJCFXLXJXPMHQ-UHFFFAOYSA-N 0.000 description 4
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 4
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Abstract
Description
R1は、シアノ、ハロゲン、メチル、及びエチルからなる群から選択される。
R2は、水素、ハロゲン、メチル、及びエチルからなる群から選択される。
R3は、ハロゲン、メチル、及びエチルからなる群から選択される。
R4は、水素、ハロゲン、メチル、エチル、及びメトキシからなる群から選択される。
R5及びR6は独立して、水素、C1〜C6−アルキル、及びヒドロキシ−C1〜C6−アルキルからなる群から選択される。あるいは、R5及びR6は、これらの両方に結合する窒素と一緒に、5員または6員のヘテロシクロアルキルを形成する。ヘテロシクロアルキルは、ハロゲン、ヒドロキシル、及びC1〜C4−アルキルからなる群から独立して選択される1つ以上の置換基で任意に置換される。
R7及びR8は独立して、水素及びC1〜C4−アルキルからなる群から選択される。
R9は、C1〜C6−アルキル、C3〜C6−シクロアルキル、C1〜C6−アルキル
−C3〜C6−シクロアルキル、ハロ−C1〜C6−アルキル、C1〜C6−アルコキシ、ハロ−C1〜C6−アルコキシ、及びC1〜C6−アルコキシ−C1〜C6−アルキルからなる群から選択される。
Xは、結合、CH2、及びOから選択される。
例示の実施形態の説明
(i)例えば、アゴメラチン、アミトリプチリン、アモキサピン、ブプロピオン、シタロプラム、クロミプラミン、デシプラミン、ドキセピン、デュロキセチン、エラザソナン、エスシタロプラム、フルボキサミン、フルオキセチン、ゲピロン、イミプラミン、イプサピロン、マプロチリン、ミルタゼプリン、ノルトリプチリン、ネファゾドン、パロキセチン、フェネルジン、プロトリプチリン、ラメルテオン、レボキセチン、ロバルゾタン、セレジリン、セルトラリン、シブトラミン、チオニソキセチン、トラニルシプロマイン、トラゾドン、トリミプラミン、ベンラファキシン及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解される、抗鬱剤。
(ii)例えば、クエチアピン及びその薬学的に活性な異性体(複数可)ならびに代謝物(複数);及びアミスルプリド、アリピプラゾール、アセナピン、ベンゾイソオキシジル、ビフェプルノックス、カルバマゼピン、クロザピン、クロルプロマジンデベンザピン、ジベンザピン、ジバルプロエクス、ドロペリドール、デュロキセチン、エスゾピクロン、フルフェナジン、ハロペリドール、イロペリドン、ラモトリジン、リチウム、ロキサピン、メソリダジン、モリンドン、オランザピン、パリペリドン、ペルラピン、ペルフェナジン、フェノチアジン、フェニルブチルピペリジン、ピモジド、プロクロルペラジン、リスペリドン、セルチンドール、スルピリド、スプロクロン、スリクロン、チオリダジン、チオチキセン、トリフルオペラジン、トリメトジン、バルプロエート、パルプロン酸塩、ゾピクロン、ゾテピン、ジプラシドン、及びこれらの等価物のうちの1つ以上を含むことが理解される、抗精神病剤。
(iii)例えば、アルネスピロン、アザピロン類、ベンゾジアゼピン類、アジナゾアオラムなどのバルビツール酸塩類、アルプラゾラム、バレゼパム、ベンタゼパム、ブロマゼパム、ブロチゾラム、ブスピロン、クロナゼパム、クロラゼプ酸塩、クロルジアゼポキシド、シプラゼパム、ジアゼパム、ジフェニルヒドラミン、エスタゾラム、フェノバム、フルニトラゼパム、フルラゼパム、フォサゼパム、ロラゼパム、ロルメタゼパム、メプロバメート、ミダゾラム、ニトラゼパム、オキサゼパム、プラゼパム、クアゼパム、レクラゼパム、スリクロン、トラカゾレート、トレピパム、テマゼパム、トリアゾラム、ウルダゼパム、ゾラゼパム、及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むよう企図される不安緩解剤。
(iv)カルバマゼピン、オキサカルバゼピン、バルプロ酸塩、ラマトロジン、ガバペンチン、トピラメート、フェニトイン、エトスクシミド、及びびこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解される、抗痙攣薬。
(v)例えば、デネペジル、ガランタミン、メマンチン、リバスチグミン、タクリン及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)を含むことが理解されるアルツハイマー病治療薬。
(vi)例えば、レボドーパ、カルビドーパ、アマンタジン、プラミペキソール、ロピニロール、ペルゴリド、カベルゴリン、アポモルフィン、ブロモクリプチン、MAOB阻害薬(例えば、セレギン及びラサギリン)、COMT阻害薬(例えば、エンタカポン及びトルカポン)、アルファ−2−阻害薬、抗コリン薬(例えば、ベンズトロピン、ビペリデン、オルフェナドリン、プロシクリジン、及びトリヘキシフェニジル)、ドーパミン再取り込み阻害薬、NMDA拮抗薬、ニコチン作動薬、ドーパミン作動薬、及び神経型一酸化窒素合成酵素の阻害薬、及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解される、パーキンソン病の治療薬及び錐体外路症状の治療用の薬剤。
(vii)例えば、アブシキシマブ、アクチバーゼ、ジスフェントンナトリウム、シチコリン、クロベネチン、デスモテプラーゼ、レピノタン、トラキソプロジル、及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解される、脳卒中治療薬。
(viii)例えば、ダラフェナシン、ジシクロミン、ファルボキサート、イミプラミン、デシプラミン、オキシブチニン、プロピベリン、プロパンテジン、ロバルゾタン、ソリフェナシン、アルファゾシン、ドキサゾシン、テラゾシン、トルテロジン、及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解される、尿失禁治療薬。
(ix)例えば、アロバルビタール、アロニミド、アモバルビタール、ベンゾクタミン、ブタバルビタール、カプリド、クロラール、クロペリドン、クロレタート、デクスクラモール、エスタゾラム、エスゾピクリン、エトクロルビノール、エトミデート、フルラゼパム、グルテチミド、ハラゼパム、ヒドロキシジン、メクロクアロン、メラトニン、メフォバルビタール、メタクアロン、ミダフルル、ミダゾラム、ニソバメート、パゴクロン、ペントバルビタール、ペルラピン、フェノバルビトール、プロポフォール、クアゼパム、ラメルテオン、ロレタミド、スプロクロン、テパゼパム、トリアゾラム、トリクロホス、セコバルビトール、ザレプロン、ゾルピデム、ゾピクロン及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解される不眠症治療薬。
(x)例えば、カルバマゼピン、ジバルプロエクス、ガバペンチン、ラモトリジン、リチウム、オランザピン、クエチアピン、バルプロン酸塩、バルプロン酸、ベラパミル、及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解される、気分安定薬。
(xi)例えば、オルリスタット、シブトラミン、リモナバント、及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)などの肥満症を治療するための医薬品。
(xii)例えば、アンフェタミン、メタンフェタミン、デキストロアンフェタミン、アトモキセチン、メチルフェニデート、デクスメチルフェニデート、モダフィニル及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解されるADHDを治療するための薬剤。
(xiii)例えば、ニコチン代替療法(例えば、ガム、パッチ、及び経鼻噴霧剤);ニコチン受容体作動薬、部分的作動薬、及び拮抗薬(例えば、バレニクリン);アコムプロセート、ブプロピオン、クロニジン、ジスルフィラム、メタドン、ナロキソン、ナルトレキソン、及びこれらの等価物ならびに薬学的に活性な異性体(複数可)及び代謝物(複数可)のうちの1つ以上を含むことが理解される、物質乱用障害、依存症、及び禁断症状を治療するために使用される薬剤。
(i)例えば、シス−プラチン、オキサリプラチン、カルボプラチン、シクロフォスファミド、窒素マスタード、メルファラン、クロラムブシル、ブスルファン、テモゾラミド、及びニトロソウレアなどのアルキル化剤;ゲムシタビン及びアンチフォレート(例えば、フルオロピリミジン(同様に5−フルオロウラシル及びテガフール)、ラルチトキセド、メトトレキサート、シトシンアラビノシド、及びヒドロキシウレア)などの代謝拮抗薬;アントラサイクリン(例えば、アドリアマイシン、ブレオマイシン、ドキソルビシン、ダウノマイシン、エピルビシン、イダルビシン、ミトマイシン−C、ダクチノマイシン及びミトラマイシン)などの抗腫瘍抗体;ビンカアルカロイド(例えば、ビンクリスチン、ビンブラスチン、ビンデシン、及びビノレルビン)、タキソイド(例えば、タキソール及びタキソテレ)、及びポロキナーゼ阻害薬などの有糸分列阻害薬;及び、エピポドフィロトキシン(例えば、エトポシド及びテニポシド)、アムサクリン、トポテカン、及びカンプトテカンなどのトポイソメラーゼ阻害薬を含むことが理解される、抗増殖剤/抗悪性腫瘍剤。
(ii)例えば、タモキシフェン、フルベストラント、トレミフェン、ラロキシフェン、ドロロキシフェン、及びヨードキシフェンなどの抗エストロゲン薬;ビカルタミド、フルタミド、ニルタミド、及び酢酸シプロテロンなどの抗アンドロゲン薬;LHRH拮抗薬;ゴセレリン、ロイプロレリン、及びブセレリンなどのLHRH作動薬;酢酸メゲストロールなどの黄体ホルモン作用物質;アナストロゾール、レトロゾール、ボラゾール、及びエキセメスタンなどのアロマターゼ阻害薬;及びフィナステリドなどの5アルファ−レダクターゼ阻害薬を含むよう企図される、細胞分裂阻害剤。
(iii)例えば、4−(6−クロロ−2,3−メチレンジオキシアニリノ)−7−[2−(4−メチルピペラジン−1−イル)エトキシ]−5−テトラヒドロピラン−4−イルオキシキナゾリン(AZD0530国際特許出願公開第WO01/94341号)、N−(2−クロロ−6−メチルフェニル)−2−{6−[4−(2−ヒドロキシエチル)ピペラジン−1−イル]−2−メチルピリミジン−4−イルアミノ}チアゾール−5−カルボキサミド(ダサチニブ、BMS−354825、J.Med.Chem.,vol.47,pp.6658−6661(2004))、及びボスチニブ(SKI−606)などのc−Srcキナーゼファミリー阻害薬;マリマスタットなどのメタロプロテイナーゼ阻害薬;ウロキナーゼプラスミノーゲンアクチベータ受容体機能の阻害薬;及びヘパラナーゼに対する抗体を含むことが理解される、抗侵入剤。
(iv)例えば、増殖因子抗体;抗−erbB2抗体トラスツズマブ(Herceptin(商標))、抗−EGFR抗体パニツムマブ、抗−erbB1抗体セツキマブ(Erbitux、C225)、及びStern et al.,Critical reviews in oncology/haematology,vol.54,pp.11−29(2005)に開示された増殖因子もしくは増殖因子受容体抗体などの増殖因子受容体抗体;上皮増殖因子ファミリーの阻害薬(例えば、N−(3−クロロ−4−フルオロフェニル)−7−メトキシ−6−(3−モルフォリノプロポキシ)キナゾリン−4−アミン(ゲフィチニブ、ZD1839)のようなEGFRファミリーチロシンイナーゼ阻害薬)、N−(3−エチニルフェニル)−6,7−ビス(2−メトキシエトキシ)キナゾリン−4−アミン(エルロチニブ、OSI−774)、ならびに6−アクリルアミド−N−(3−クロロ−4−フルオロフェニル)−7−(3−モルフォリノプロポキシ)−キナゾリン−4−アミン(CI1033))及びerbB2チロシンキナーゼ阻害薬(例えば、ラパチニブ)などのチロシンキナーゼ阻害薬;肝細胞増殖因子ファミリーの阻害薬;インスリン増殖因子ファミリーの阻害薬;イマチニブ及びに路地に部(AMN107)などの血小板由来増殖因子ファミリーの阻害薬;Ras/Rafシグナル伝達阻害薬(例えば、ソラフェニブ(BAY43−9006)、チピファルニブ(R115777)、ならびにロナファルニブ(SCH66336)のようなファルネシルトランスフェラーゼ阻害薬)などのセリン/スレオニンキナーゼの阻害薬;MEK及び/またはAKTキナーゼを通しての細胞シグナル伝達の阻害薬;c−kit阻害薬;ablキナーゼ阻害薬、PI3キナーゼ阻害薬;Plt3キナーゼ阻害薬;CSF−1Rキナーゼ阻害薬;IGF受容体(インスリン様増殖因子)キナーゼ阻害薬);AZD1152、PH739358、VX−680、MLN8054、R763、MP235、MP529、VX−528及びAX39459などのオーロラキナーゼ阻害薬;及びCDK2ならびにCDK4阻害薬などのサイクリン依存性キナーゼ阻害薬を含むことが理解される、増殖因子機能の阻害薬。
(v)例えば、抗血管内皮細胞増殖因子抗体ベバシズマブ(Avastin(商標))及びVEGF受容体チロシンキナーゼ阻害薬(例えば、バンデタニブ(ZD6474)、バタラニブ(PTK787)、スニチニブ(SU11248)、アキチニブ(AG−013736)、パゾパニブ(GW786034)、ならびに4−(4−フルオロ−2−メチルインドール−5−イルオキシ)−6−メトキシ−7−(3−ピロリジン−1−イルプロポキシ)キナゾリン(AZD2171、国際特許出願公開第WO00/47212号の実施例240)などの血管内皮増殖因子の効果を阻害するもの;国際特許出願公開第WO97/22596号、同第WO97/30035号、同第WO97/32856号、及び同第98/13354号に開示される化合物;及びリノミド、インテグリンαvβ3機能の阻害薬、ならびにアンジオスタチンなどの他の機構によって作用する化合物を含むことが理解される、抗血管新生薬。
(vi)例えば、コンブレタスタチンA4及び国際特許出願公開第WO99/02166号、同第WO00/40529号、同第WO00/41669号、同第WO01/92224号、同第WO02/04434号ならびに同第WO02/08213号に開示される化合物を含むことが理解される、血管傷害剤。
(vii)例えば、ジボテンタン(ZD4054)及びアトラセンタンを含むことが理解される、エンドセリン受容体拮抗薬。
(viii)例えば、ISIS2503(抗−rasアンチセンス)などの上記で列挙した標的に向けられるものを含むことが理解される、アンチセンス療法。
(ix)例えば、異常p53、BRCA1、またはBRCA2などの異常遺伝子を置き換えるためのアプローチ;シトシンデアミナーゼ、チミジンキナーゼ、または細菌ニトロレダクターゼ酵素を使用するものなどのGDEPT(遺伝子指向性酵素プロドラッグ療法)アプローチ;及び多剤耐性遺伝子療法などの化学療法または放射線療法に対する患者の耐性を増加させるためのアプローチを含むことが理解される、遺伝子療法アプローチ。
(x)例えば、サイトカイン(例えば、インターロイキン2、インターロイキン4、または顆粒球マクロファージコロニー刺激因子)によるトランスフェクションなどの患者の腫瘍細胞の免疫原性を増加させるためのエクスビボならびにインビボアプローチ;T細胞アネルギーを減少させるためのアプローチ;サイトカインでトランスフェクトした樹状細胞などのトランスフェクトした免疫細胞を使用するアプローチ;サイトカインでトランスフェクトした腫瘍細胞系を使用するアプローチ;及び抗イディオタイプ抗体を使用するアプローチを含むことが理解される免疫療法アプローチ。
以下の例は、本発明の実施形態の単に例示であり、本開示の後段部分に多少なりとも限定するものではない。
以下の実施例1〜47は、本発明の多種多様な化合物及びこうした化合物を製造するための中間体の調製を示す。有機合成分野の当業者であれば、これらの実施例を単独で、または当該技術分野における一般的知識と組み合わせて読み取った後に、本方法を本発明で包含されるいかなる化合物を製造するために適合かつ適用され得ることが予想される。当該技術分野における一般的知識としては、例えば、
A)例えば、Protective Groups in Organic Synthesis,T.W.Green,P.G.M.Wuts,Wiley−Interscience,New York(1999)に記載されている、保護基及び好適な保護基の例を使用するための慣用的な手順。
B)種々の有機合成反応を説明する参考文献は、例えば、Advanced Organic Chemistry,March 4th ed,McGraw Hill(1992);及びOrganic Synthesis,Smith,McGraw Hill,(1994)などの有機化学の教本を含む、種々の有機合成反応を説明する参考文献。これらはまた、例えば、R.C. Larock,Comprehensive Organic Transformations,2nd ed.,Wiley−VCH:New York(1999);F.A.Carey;R.J.Sundberg,Advanced Organic Chemistry,2nd ed.,Plenum Press:New York(1984);L.S.Hegedus,Transition Metals in the Synthesis of Complex Organic Molecules,2nd ed.,University Science Books:Mill Valley,CA(1994);L.A.Paquette,Ed.,The Encyclopedia of Reagents for Organic Synthesis,John Wiley:New York(1994);A.R.Katritzky,O.Meth−Cohn,CW.Rees,Eds.,Comprehensive Organic Functional Group Transformations,Pergamon Press:Oxford,UK(1995);G.Wilkinson;F.G A.Stone;E.W.Abel,Eds.,Comprehensive Organometallic Chemistry,Pergamon Press:Oxford,UK(1982);B.M.Trost;I.Fleming,Comprehensive Organic Synthesis, Pergamon Press: Oxford,UK(1991);A.R.Katritzky,CW.Rees Eds.,Comprehensive Heterocyclic Chemistry,Pergamon Press:Oxford,UK(1984);A.R.Katritzky;CW.Rees,E.F.V.Scriven,Eds.,Comprehensive Heterocyclic Chemistry II,Pergamon Press:Oxford,UK(1996);C.Hansen;P.G.Sammes;J.B.Taylor,Eds.,Comprehensive Medicinal Chemistry:Pergamon Press:Oxford,UK(1990)を含む。加えて、合成方法論の定期的な見直し及び関連項目としては、Organic Reactions,John Wiley:New York;Organic Syntheses;John Wiley:New York;The Total Synthesis of Natural Products,John Wiley:New York;The Organic Chemistry of Drug Synthesis,John Wiley:New York;Annual Reports in Organic Synthesis,Academic Press:San Diego CA;及びMethoden der Organischen Chemie(Houben−Weyl),Thieme:Stuttgart,Germanyを含む。
C)例えば、Heterocyclic Chemistry,J.A.Joule,K.Mills,G.F.Smith,3rd ed.,Cheapman and Hall,p.189−225(1995);及びHeterocyclic Chemistry,T.L.Gilchrist,2nd ed.Longman Scientific and Technical,p.248−282(1992)を含む、ヘテロ環式化学を説明する参考文献。
D)CASオンラインまたはSciFinderのいずれかを用いて検索され得るChemical Abstract、及びSpotFireを用いて検索され得るHandbuch der Organischen Chemie(Beilstein)を含む合成変換のデータベース。
参考文献:Org.Synth.Coll.Vol.V,p179。
1H NMR(300MHz,CDCl3):δppm1.13−1.22(m,3H),1.46(s,9H),1.71−1.81(m,0.5H),1.86−1.96(m,0.5H),2.15−2.40(m,1H),2.88−2.98(m,0.5H),3.00−3.13(m,0.5H),3.48−3.58(m,0.5H),3.60−3.75(m,1.5H),3.85−4.05(m,1H)9.65及び9.73(2d,J=2.14及び1.51Hz,1H)。
実施例13.(2S,5R)−tert−ブチル2−エチニル−5−メチルモルフォリン−4−カルボキシレート
9[M−Boc+H]+。
LCMSm/z281.02[M+H]+(ESI)。
LCMSm/z280.10[M+H]+(ESI)。
本発明における化合物の拮抗薬特性を、RLE細胞(ラット肝臓内皮細胞、ATCC)中で発現される、hP2X3(ヒトプリン作動性P2X受容体サブタイプ3、クローンAについての受入番号AB016608及びクローンBについての受入番号NM_002559)の活性によって誘起される細胞内カルシウム増加の阻害薬として評価した。RLE/hP2X3細胞を、10%のウシ胎児血清(Wisent、090850)、2mMのL−グルタミン(Wisent、609−065―EL)、及び600μg/mLのGeneticin−G418(Wisent、61234)で補充したウィリアムの培地1X(Gibco、12551−032)中で、加湿したインキュベーター(5%CO2及び37℃)中で増殖させた。
本発明の化合物のうちの1つを、炎症性疼痛のインビボモデルにおいて評価した。実施例15の経口投与(0.3−1−3−10−20μmol/kg)は、炎症性疼痛のラットFCA 96時間の足モデルにおいて、熱的痛感過敏及び機械的痛感過敏の両方のエンドポイントの遊離血漿濃度依存性の好転をもたらした。実施例15の効力(EC50遊離血漿濃度)は、熱的痛感過敏及び機械的痛感過敏の好転において、それぞれ18nM及び87nMであった。結果を図1及び2に示す。
体重200〜225gの雄のスプラーグドーレイラット(Charles River,St−Constant,Qc.CAN)を、動物実験試験に使用した。動物は、食餌(14%Protein Rodent Maintenance Diet、Harlan,Teklad,Madison,WI,USA)及び水が自由に与えられて、制御された環境室(12時間の明/暗周期、20.5〜23.5℃、相対湿度40〜70%)において、ポリカーボネート製の通気されたケージ(フィルタートップ)中で群飼した。
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Claims (32)
- 式Iの化合物またはその塩であって、
前記式Iの化合物が、
R1が、シアノ、ハロゲン、メチル、及びエチルからなる群から選択され、
R2が、水素、ハロゲン、メチル、及びエチルからなる群から選択され、
R3が、ハロゲン、メチル、及びエチルからなる群から選択され、
R4が、水素、ハロゲン、メチル、エチル、及びメトキシからなる群から選択され、
R5及びR6については、
R5及びR6が、水素、C1〜C6−アルキル、及びヒドロキシ−C1〜C6−アルキルからなる群から独立して選択されるか、あるいは
R5及びR6が、これら両方が結合する窒素と一緒に、5員または6員のヘテロシクロアルキルを形成し、
前記ヘテロシクロアルキルが、ハロゲン、ヒドロキシル、及びC1−C4−アルキルからなる群から独立して選択される1つ以上の置換基で任意に置換され、
R7及びR8が、水素及びC1〜C4−アルキルからなる群から独立して選択され、
R9が、C1〜C6−アルキル、C3〜C6−シクロアルキル、C1〜C6−アルキル−C3〜C6−シクロアルキル、ハロ−C1〜C6−アルキル、C1〜C6−アルコキシ、ハロ−C1〜C6−アルコキシ、及びC1〜C6−アルコキシ−C1〜C6−アルキルからなる群から選択され、
Xが、結合、CH2、及びOから選択される、化合物またはその塩。 - R1が、メチルである、請求項1に記載の化合物または塩。
- R2が、水素である、請求項1〜2のいずれか一項に記載の化合物または塩。
- R3が、フルオロである、請求項1〜3のいずれか一項に記載の化合物または塩。
- R4が、フルオロである、請求項1〜4のいずれか一項に記載の化合物または塩。
- Xが、Oである、請求項1〜5のいずれか一項に記載の化合物または塩。
- R5が、水素である、請求項1〜7のいずれか一項に記載の化合物または塩。
- R6が、C1〜C6−アルキルである、請求項1〜8のいずれか一項に記載の化合物または塩。
- R6が、メチルである、請求項9に記載の化合物または塩。
- R7が、水素である、請求項1〜10のいずれか一項に記載の化合物または塩。
- R8が、水素である、請求項1〜11のいずれか一項に記載の化合物または塩。
- R9が、C1〜C6−アルコキシである、請求項1〜12のいずれか一項に記載の化合物または塩。
- R9が、メトキシである、請求項13に記載の化合物または塩。
- 薬学的組成物であって、
請求項1〜16のいずれか一項に記載の化合物または塩と、
担体、希釈剤、または賦形剤と、を含む薬学的組成物。 - キットであって、
請求項1〜16のいずれか一項に記載の化合物または塩と、
前記化合物または塩を動物患者に投与するための器具と、前記化合物または塩を動物患者に投与するための使用説明書と、担体、希釈剤、または賦形剤と、前記化合物または塩以外の薬学的に活性な成分と、を含むキット。 - 医薬品としての使用のための、請求項1〜16のいずれか一項に記載の化合物または塩。
- 動物においてP2X3活性に関連する病態を治療するための医薬品の製造における、請求項1〜16のいずれか一項に記載の化合物または塩の使用。
- 動物においてP2X2/3活性に関連する病態を治療するための医薬品の製造における、請求項1〜16のいずれか一項に記載の化合物または塩の使用。
- 動物において疼痛を治療するための医薬品の製造における、請求項1〜16のいずれか一項に記載の化合物または塩の使用。
- 動物において尿管障害を治療するための医薬品の製造における、請求項1〜16のいずれか一項に記載の化合物または塩の使用。
- 前記動物が、哺乳動物である、請求項20〜23のいずれか一項に記載の使用。
- 前記哺乳動物が、ヒトである、請求項24に記載の使用。
- P2X3活性に関連する障害の治療を、こうした治療を必要とする動物において行うための方法であって、前記動物に、治療上有効量の請求項1〜16のいずれか一項に記載の化合物または塩を投与することを含む、方法。
- P2X2/3活性に関連する障害の治療を、こうした治療を必要とする動物において行うための方法であって、前記動物に、治療上有効量の請求項1〜16のいずれか一項に記載の化合物または塩を投与することを含む、方法。
- 疼痛の治療を、こうした治療を必要とする動物において行うための方法であって、前記動物に、治療上有効量の請求項1〜16のいずれか一項に記載の化合物または塩を投与することを含む、方法。
- 尿管障害の治療を、こうした治療を必要とする動物において行うための方法であって、前記動物に、治療上有効量の請求項1〜16のいずれか一項に記載の化合物または塩を投与することを含む、方法。
- 前記尿管障害が、過活動性膀胱を含む、請求項29に記載の方法。
- 前記動物が、哺乳動物である、請求項26〜30のいずれか一項に記載の方法。
- 前記哺乳動物が、ヒトである、請求項31に記載の方法。
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JP2022515879A (ja) * | 2018-12-29 | 2022-02-22 | 武漢朗来科技発展有限公司 | 複素環式化合物、中間体、その製造方法及び応用 本願は、出願日が2018年12月29日の中国特許出願cn 201811642319、出願日が2019年05月24日の中国特許出願cn201910440214.3及び出願日が2019年10月24日の中国特許出願cn201911016158.7に基づいて優先権を主張する。また、上記中国特許出願の全文は本願に援用される。 |
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JP2020534355A (ja) * | 2017-09-18 | 2020-11-26 | べルス・ヘルス・コフ・インコーポレーテッド | 選択的p2x3修飾薬 |
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