JP4129445B2

JP4129445B2 - ベンズイミダゾロンカルボン酸誘導体

ベンズイミダゾロンカルボン酸誘導体 Download PDF

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Publication number: JP4129445B2
Authority: JP; Japan
Prior art keywords: methyl; group; reaction; isopropyl; piperidin
Prior art date: 2004-06-15
Legal status : Expired - Fee Related

Application number

JP2004177488A

Other languages

English (en)

Japanese (ja)

Other versions

JP2006001845A5 (https=

JP2006001845A (ja

Inventor

力内田

大紀曽根

聡井口

幸司安藤

Original Assignee

ファイザー・インク

Priority date

2004-06-15

Filing date

2004-06-15

Publication date

2008-08-06

2004-06-15 Application filed by ファイザー・インク filed Critical ファイザー・インク

2004-06-15 Priority to JP2004177488A priority Critical patent/JP4129445B2/ja

2005-01-06 Priority to UAA200613251A priority patent/UA82297C2/uk

2005-06-01 Priority to EA200602122A priority patent/EA010891B9/ru

2005-06-01 Priority to MXPA06014486A priority patent/MXPA06014486A/es

2005-06-01 Priority to BRPI0512046-2A priority patent/BRPI0512046A/pt

2005-06-01 Priority to AP2006003847A priority patent/AP2418A/xx

2005-06-01 Priority to CN2005800197343A priority patent/CN1968946B/zh

2005-06-01 Priority to EP05750293A priority patent/EP1758891A2/en

2005-06-01 Priority to KR1020067026378A priority patent/KR100875558B1/ko

2005-06-01 Priority to EA200801608A priority patent/EA200801608A1/xx

2005-06-01 Priority to EA200801607A priority patent/EA200801607A1/xx

2005-06-01 Priority to HK07108217.3A priority patent/HK1104031B/xx

2005-06-01 Priority to CA2569654A priority patent/CA2569654C/en

2005-06-01 Priority to GEAP20059755A priority patent/GEP20094638B/en

2005-06-01 Priority to PCT/IB2005/001825 priority patent/WO2005123718A2/en

2005-06-01 Priority to NZ551341A priority patent/NZ551341A/en

2005-06-01 Priority to AU2005254800A priority patent/AU2005254800B2/en

2005-06-13 Priority to PE2005000671A priority patent/PE20060298A1/es

2005-06-14 Priority to TW094119692A priority patent/TWI298635B/zh

2005-06-14 Priority to US11/153,766 priority patent/US7737163B2/en

2005-06-14 Priority to UY28961A priority patent/UY28961A1/es

2005-06-14 Priority to ARP050102433A priority patent/AR049353A1/es

2005-06-14 Priority to US11/153,757 priority patent/US7595329B2/en

2005-06-14 Priority to NL1029250A priority patent/NL1029250C2/nl

2005-06-14 Priority to US11/153,775 priority patent/US7705020B2/en

2005-06-15 Priority to SV2005002145A priority patent/SV2008002145A/es

2005-06-15 Priority to PA20058636901A priority patent/PA8636901A1/es

2005-06-15 Priority to GT200500156A priority patent/GT200500156A/es

2006-01-05 Publication of JP2006001845A publication Critical patent/JP2006001845A/ja

2006-11-09 Priority to NO20065160A priority patent/NO20065160L/no

2006-11-20 Priority to CR8756A priority patent/CR8756A/es

2006-11-27 Priority to IL179612A priority patent/IL179612A/en

2006-11-30 Priority to ZA200610054A priority patent/ZA200610054B/en

2006-12-13 Priority to EC2006007079A priority patent/ECSP067079A/es

2006-12-14 Priority to TNP2006000414A priority patent/TNSN06414A1/fr

2006-12-15 Priority to MA29536A priority patent/MA28667B1/fr

2007-08-02 Publication of JP2006001845A5 publication Critical patent/JP2006001845A5/ja

2008-01-09 Priority to US11/971,265 priority patent/US20080108660A1/en

2008-08-06 Application granted granted Critical

2008-08-06 Publication of JP4129445B2 publication Critical patent/JP4129445B2/ja

2024-06-15 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims description 25
150000001875 compounds Chemical class 0.000 claims description 233
-1 5-oxo-1,2,4-oxadiazol-3-yl group Chemical group 0.000 claims description 112
239000003814 drug Substances 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 39
239000012453 solvate Substances 0.000 claims description 22
125000001424 substituent group Chemical group 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
PNURFGPXCDPKGS-UHFFFAOYSA-N 1-[[4-[[(2-oxo-3-propan-2-ylbenzimidazole-1-carbonyl)amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound O=C1N(C(C)C)C2=CC=CC=C2N1C(=O)NCC(CC1)CCN1CC1(C(O)=O)CCC1 PNURFGPXCDPKGS-UHFFFAOYSA-N 0.000 claims description 4
HTZFYUOWTBOSHI-UHFFFAOYSA-N 1-[[4-[[(2-oxo-3-propan-2-ylbenzimidazole-1-carbonyl)amino]methyl]piperidin-1-yl]methyl]cyclohexane-1-carboxylic acid Chemical compound O=C1N(C(C)C)C2=CC=CC=C2N1C(=O)NCC(CC1)CCN1CC1(C(O)=O)CCCCC1 HTZFYUOWTBOSHI-UHFFFAOYSA-N 0.000 claims description 4
125000005156 substituted alkylene group Chemical group 0.000 claims description 4
YRPFGWDYFLMBLW-UHFFFAOYSA-N 1-[[4-[[(2-oxo-3-propan-2-ylbenzimidazole-1-carbonyl)amino]methyl]piperidin-1-yl]methyl]cyclopentane-1-carboxylic acid Chemical compound O=C1N(C(C)C)C2=CC=CC=C2N1C(=O)NCC(CC1)CCN1CC1(C(O)=O)CCCC1 YRPFGWDYFLMBLW-UHFFFAOYSA-N 0.000 claims description 3
URUXDSRTGCEPQU-UHFFFAOYSA-N 1-[[4-hydroxy-4-[[(2-oxo-3-propan-2-ylbenzimidazole-1-carbonyl)amino]methyl]piperidin-1-yl]methyl]cyclohexane-1-carboxylic acid Chemical compound O=C1N(C(C)C)C2=CC=CC=C2N1C(=O)NCC(CC1)(O)CCN1CC1(C(O)=O)CCCCC1 URUXDSRTGCEPQU-UHFFFAOYSA-N 0.000 claims description 3
PCDRKSCASYEJSM-UHFFFAOYSA-N 4-[[4-[[(2-oxo-3-propan-2-ylbenzimidazole-1-carbonyl)amino]methyl]piperidin-1-yl]methyl]oxane-4-carboxylic acid Chemical compound O=C1N(C(C)C)C2=CC=CC=C2N1C(=O)NCC(CC1)CCN1CC1(C(O)=O)CCOCC1 PCDRKSCASYEJSM-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 description 265
238000006243 chemical reaction Methods 0.000 description 168
239000002904 solvent Substances 0.000 description 97
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
239000000243 solution Substances 0.000 description 61
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
238000000034 method Methods 0.000 description 57
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
239000000203 mixture Substances 0.000 description 49
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
239000003153 chemical reaction reagent Substances 0.000 description 45
238000005481 NMR spectroscopy Methods 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 38
229940079593 drug Drugs 0.000 description 37
238000005160 1H NMR spectroscopy Methods 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
239000002585 base Chemical class 0.000 description 24
125000006239 protecting group Chemical group 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
238000009472 formulation Methods 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000007858 starting material Substances 0.000 description 20
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 18
230000002829 reductive effect Effects 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
230000035484 reaction time Effects 0.000 description 17
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
210000004027 cell Anatomy 0.000 description 16
102000005962 receptors Human genes 0.000 description 15
108020003175 receptors Proteins 0.000 description 15
238000010898 silica gel chromatography Methods 0.000 description 15
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
238000003756 stirring Methods 0.000 description 13
239000003826 tablet Substances 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
QSLJOIOPNUQETJ-UHFFFAOYSA-N 2-benzyltetrazole Chemical compound N1=CN=NN1CC1=CC=CC=C1 QSLJOIOPNUQETJ-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
201000006549 dyspepsia Diseases 0.000 description 12
150000002170 ethers Chemical class 0.000 description 12
150000008282 halocarbons Chemical class 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
239000007787 solid Substances 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
238000001816 cooling Methods 0.000 description 11
239000000843 powder Substances 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
238000011282 treatment Methods 0.000 description 11
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
239000003638 chemical reducing agent Substances 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
230000008569 process Effects 0.000 description 10
239000000651 prodrug Substances 0.000 description 10
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 9
239000007995 HEPES buffer Substances 0.000 description 9
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230000027455 binding Effects 0.000 description 9
201000010099 disease Diseases 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
239000006188 syrup Substances 0.000 description 9
235000020357 syrup Nutrition 0.000 description 9
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 8
239000000872 buffer Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
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235000018102 proteins Nutrition 0.000 description 8
102000004169 proteins and genes Human genes 0.000 description 8
108090000623 proteins and genes Proteins 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
239000012230 colorless oil Substances 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
235000011167 hydrochloric acid Nutrition 0.000 description 7
239000003921 oil Substances 0.000 description 7
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
239000000725 suspension Substances 0.000 description 7
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
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239000000556 agonist Substances 0.000 description 6
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239000003795 chemical substances by application Substances 0.000 description 6
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238000010511 deprotection reaction Methods 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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239000012528 membrane Substances 0.000 description 6
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229960002994 dofetilide Drugs 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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238000007911 parenteral administration Methods 0.000 description 5
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208000019695 Migraine disease Diseases 0.000 description 4
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206010028813 Nausea Diseases 0.000 description 4
208000012902 Nervous system disease Diseases 0.000 description 4
208000025966 Neurological disease Diseases 0.000 description 4
206010030216 Oesophagitis Diseases 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
206010047700 Vomiting Diseases 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
230000036592 analgesia Effects 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
206010003119 arrhythmia Diseases 0.000 description 4
230000006793 arrhythmia Effects 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
208000015114 central nervous system disease Diseases 0.000 description 4
208000010877 cognitive disease Diseases 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 4
208000006881 esophagitis Diseases 0.000 description 4
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 4
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