CA2619518A1 - Isotopically substituted benzimidazole derivatives - Google Patents

Isotopically substituted benzimidazole derivatives Download PDF

Info

Publication number: CA2619518A1
Authority: CA; Canada
Prior art keywords: alkyl; alkoxy; hydrogen; hydroxy; cycloalkyl
Prior art date: 2005-08-22
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

Application number

CA002619518A

Other languages

English (en)

French (fr)

Inventor

Bernhard Kohl

Peter Jan Zimmermann

Karl Zech

Peter Zimmermann

Wilm Buhr

Andreas Palmer

Christof Brehm

Maria Vittoria Chiesa

Michael David

Oliver Von Richter

Wolfgang-Alexander Simon

Stefan Postius

Wolfgang Kromer

Hans Christof Holst

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda GmbH

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

2005-08-22

Filing date

2006-08-18

Publication date

2007-03-01

2006-08-18 Application filed by Individual filed Critical Individual

2007-03-01 Publication of CA2619518A1 publication Critical patent/CA2619518A1/en

Status Abandoned legal-status Critical Current

Links

229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 11
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 248
-1 fluoro-1-4C-alkyl Chemical group 0.000 claims description 193
229910052739 hydrogen Inorganic materials 0.000 claims description 192
239000001257 hydrogen Substances 0.000 claims description 191
150000002431 hydrogen Chemical group 0.000 claims description 172
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 82
229910052736 halogen Inorganic materials 0.000 claims description 77
150000002367 halogens Chemical group 0.000 claims description 77
150000003839 salts Chemical group 0.000 claims description 71
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 65
229910052805 deuterium Inorganic materials 0.000 claims description 57
150000001975 deuterium Chemical group 0.000 claims description 49
239000003814 drug Substances 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 27
125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 24
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 24
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
239000001301 oxygen Substances 0.000 claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
208000018522 Gastrointestinal disease Diseases 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 6
238000011321 prophylaxis Methods 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 4
BRPAYRDNHUJVRH-UHFFFAOYSA-N 7-[(2,6-dimethylphenyl)methylamino]-2,3-dimethylbenzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2N(C)C(C)=NC2=C1NCC1=C(C)C=CC=C1C BRPAYRDNHUJVRH-UHFFFAOYSA-N 0.000 claims description 3
ONYZLGIHUXLUPZ-UHFFFAOYSA-N CC1=C(CNC2=CC(=CC3=C2N=C(N3CC)C)C(=O)O)C(=CC=C1)C Chemical compound CC1=C(CNC2=CC(=CC3=C2N=C(N3CC)C)C(=O)O)C(=CC=C1)C ONYZLGIHUXLUPZ-UHFFFAOYSA-N 0.000 claims description 3
MTXXORNCDDPOJH-UHFFFAOYSA-N CC=1N(C2=C(N1)C(=CC(=C2)C(=O)O)NCC2=C(C=CC=C2)C)C Chemical compound CC=1N(C2=C(N1)C(=CC(=C2)C(=O)O)NCC2=C(C=CC=C2)C)C MTXXORNCDDPOJH-UHFFFAOYSA-N 0.000 claims description 3
YHEFSWGDKLAWDO-UHFFFAOYSA-N 7-[(2-ethyl-6-methylphenyl)methylamino]-2-(methoxymethyl)-3-methylbenzimidazole-5-carboxylic acid Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(O)=O)=CC2=C1N=C(COC)N2C YHEFSWGDKLAWDO-UHFFFAOYSA-N 0.000 claims description 2
ILQQFMVUWMEUGI-MVQVZBQJSA-N 7-[n-(dideuteriomethyl)-2,6-dimethylanilino]-n,n,2-trimethyl-3-(trideuteriomethyl)benzimidazole-5-carboxamide Chemical compound C=1C(C(=O)N(C)C)=CC=2N(C([2H])([2H])[2H])C(C)=NC=2C=1N(C([2H])[2H])C1=C(C)C=CC=C1C ILQQFMVUWMEUGI-MVQVZBQJSA-N 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
UXQAEVANCLXJQR-MNRNQTOZSA-N CC1=C(C(=CC=C1)C)N(C1=CC(=CC2=C1N=C(N2C)C)C(=O)O)C([2H])[2H].CC2=C(C(=CC=C2)C)N(C2=CC(=CC1=C2N=C(N1C)C)C(=O)OCC)C([2H])[2H] Chemical compound CC1=C(C(=CC=C1)C)N(C1=CC(=CC2=C1N=C(N2C)C)C(=O)O)C([2H])[2H].CC2=C(C(=CC=C2)C)N(C2=CC(=CC1=C2N=C(N1C)C)C(=O)OCC)C([2H])[2H] UXQAEVANCLXJQR-MNRNQTOZSA-N 0.000 claims 1
DLFQFALGJTWKHX-DRGWXPQLSA-N CC1=C(CNC2=CC(=CC3=C2N=C(N3)C)C(=O)O)C(=CC=C1)C.CN(C(=O)C1=CC3=C(N=C(N3C)C)C(=C1)N(C[2H])C1=C(C=CC=C1C)C)C Chemical compound CC1=C(CNC2=CC(=CC3=C2N=C(N3)C)C(=O)O)C(=CC=C1)C.CN(C(=O)C1=CC3=C(N=C(N3C)C)C(=C1)N(C[2H])C1=C(C=CC=C1C)C)C DLFQFALGJTWKHX-DRGWXPQLSA-N 0.000 claims 1
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210000004211 gastric acid Anatomy 0.000 abstract description 4
230000028327 secretion Effects 0.000 abstract description 3
235000013350 formula milk Nutrition 0.000 description 169
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 144
102100031265 Chromodomain-helicase-DNA-binding protein 2 Human genes 0.000 description 86
101000777079 Homo sapiens Chromodomain-helicase-DNA-binding protein 2 Proteins 0.000 description 86
101000880945 Homo sapiens Down syndrome cell adhesion molecule Proteins 0.000 description 86
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
238000006243 chemical reaction Methods 0.000 description 42
238000000034 method Methods 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
239000000203 mixture Substances 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 21
238000003786 synthesis reaction Methods 0.000 description 21
230000015572 biosynthetic process Effects 0.000 description 20
239000007787 solid Substances 0.000 description 19
125000001424 substituent group Chemical group 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
150000001556 benzimidazoles Chemical class 0.000 description 17
239000003153 chemical reaction reagent Substances 0.000 description 17
238000002425 crystallisation Methods 0.000 description 17
230000008025 crystallization Effects 0.000 description 17
229910052943 magnesium sulfate Inorganic materials 0.000 description 17
235000019341 magnesium sulphate Nutrition 0.000 description 17
238000000746 purification Methods 0.000 description 17
239000002253 acid Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
230000008569 process Effects 0.000 description 15
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
150000003254 radicals Chemical class 0.000 description 13
229940079593 drug Drugs 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
239000000725 suspension Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
230000009471 action Effects 0.000 description 11
238000004440 column chromatography Methods 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000004480 active ingredient Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
230000009467 reduction Effects 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
UVPBCQHSNIWHFU-UHFFFAOYSA-N 2-methyl-7-nitro-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(C)=NC2=C1[N+]([O-])=O UVPBCQHSNIWHFU-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
235000011054 acetic acid Nutrition 0.000 description 6
239000005557 antagonist Substances 0.000 description 6
238000001212 derivatisation Methods 0.000 description 6
230000002496 gastric effect Effects 0.000 description 6
FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 6
229940107698 malachite green Drugs 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
229940126409 proton pump inhibitor Drugs 0.000 description 6
230000001603 reducing effect Effects 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
239000012317 TBTU Substances 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 5
125000005002 aryl methyl group Chemical group 0.000 description 5
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms

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CA002619518A 2005-08-22 2006-08-18 Isotopically substituted benzimidazole derivatives Abandoned CA2619518A1 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
EP05107688.3		2005-08-22
EP05107688		2005-08-22
EP06101624		2006-02-14
EP06101624.2		2006-02-14
PCT/EP2006/065447 WO2007023135A1 (en)	2005-08-22	2006-08-18	Isotopically substituted benzimidazole derivatives

Publications (1)

Publication Number	Publication Date
CA2619518A1 true CA2619518A1 (en)	2007-03-01

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Family Applications (1)

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CA002619518A Abandoned CA2619518A1 (en)	2005-08-22	2006-08-18	Isotopically substituted benzimidazole derivatives

Country Status (5)

Country	Link
EP (1)	EP1926714A1 (ja)
JP (1)	JP2009504798A (ja)
AU (1)	AU2006283876A1 (ja)
CA (1)	CA2619518A1 (ja)
WO (1)	WO2007023135A1 (ja)

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JP2009511481A (ja)	2005-10-06	2009-03-19	オースペックス・ファーマシューティカルズ・インコーポレイテッド	増強された治療特性を持つ、胃Ｈ＋，Ｋ＋−ＡＴＰａｓｅの重水素化阻害剤
WO2007072142A2 (en) *	2005-12-19	2007-06-28	Pfizer Japan Inc.	Benzimidazole-5-carboxamide derivatives
WO2009094457A2 (en) *	2008-01-22	2009-07-30	Auspex Pharmaceuticals	Substituted benzhydrylethers
EP2452680B1 (en)	2009-07-09	2019-12-18	RaQualia Pharma Inc.	Acid pump antagonist for the treatment of diseases involved in abnormal gastrointestinal motility
ES2903523T3 (es)	2015-02-02	2022-04-04	Valo Health Inc	Acidos 3-aril-4-amido-biciclico [4.5.0]hidroxámicos como inhibidores de HDAC
WO2016126726A1 (en)	2015-02-02	2016-08-11	Forma Therapeutics, Inc.	Bicyclic [4,6,0] hydroxamic acids as hdac6 inhibitors
WO2017218950A1 (en)	2016-06-17	2017-12-21	Forma Therapeutics, Inc.	2-spiro-5- and 6-hydroxamic acid indanes as hdac inhibitors
KR20190057569A (ko) *	2017-11-20	2019-05-29	제일약품주식회사	7-아미노-1h-인돌-5-카르복사미드 유도체 및 이의 용도
CN113651663B (zh) *	2021-08-20	2024-03-29	浙大宁波理工学院	一种氘代芳香羰基类化合物的制备方法
WO2024087155A1 (zh) *	2022-10-28	2024-05-02	深圳市华先医药科技有限公司	一种合成4-羟基-n,n,2-三甲基苯并咪唑-6-甲酰胺的方法
WO2024087156A1 (zh) *	2022-10-28	2024-05-02	深圳市华先医药科技有限公司	4-羟基-n,n,2-三甲基苯并咪唑-6-甲酰胺的可放大生产方法

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US6334997B1 (en) *	1994-03-25	2002-01-01	Isotechnika, Inc.	Method of using deuterated calcium channel blockers
SE9602286D0 (sv) *	1996-06-10	1996-06-10	Astra Ab	New compounds
AR043063A1 (es) *	2002-12-13	2005-07-13	Altana Pharma Ag	Bencimidazoles 6-sustituidos y su uso como inhibidores de secreciones gastricas
AR049168A1 (es) *	2004-05-18	2006-07-05	Altana Pharma Ag	Derivados de benzimidazol

2006
- 2006-08-18 JP JP2008527450A patent/JP2009504798A/ja active Pending
- 2006-08-18 EP EP06792891A patent/EP1926714A1/en not_active Withdrawn
- 2006-08-18 AU AU2006283876A patent/AU2006283876A1/en not_active Abandoned
- 2006-08-18 CA CA002619518A patent/CA2619518A1/en not_active Abandoned
- 2006-08-18 WO PCT/EP2006/065447 patent/WO2007023135A1/en active Application Filing

Also Published As

Publication number	Publication date
WO2007023135A1 (en)	2007-03-01
JP2009504798A (ja)	2009-02-05
EP1926714A1 (en)	2008-06-04
AU2006283876A1 (en)	2007-03-01

Publication	Publication Date	Title
CA2619518A1 (en)	2007-03-01	Isotopically substituted benzimidazole derivatives
US20060194969A1 (en)	2006-08-31	4-Substituted benzimidazoles and their uses as inhibitors of gastric secretion
JP2008542217A (ja)	2008-11-27	炎症またはアレルギー状態の処置のための有機化合物
CZ296275B6 (cs)	2006-02-15	Pyrroloindoly, pyridoindoly a azepinoindoly jako agonisté 5-HT2C a jejich pouzití
KR20070087605A (ko)	2007-08-28	ＣＲＴｈ2 수용체 길항제 활성을 갖는 피롤 유도체
WO2007039464A1 (en)	2007-04-12	Isotopically substituted imidazopyridine derivatives for the treatment of gastrointestinal disorders
US20090093473A1 (en)	2009-04-09	Spiro-benzimidazoles as inhibitors of gastric acid secretion
WO2008151927A2 (en)	2008-12-18	6-n-substituted benz imidazole derivatives as acid pump antagonists
WO2008015196A1 (en)	2008-02-07	5-,7-bis-substituted imidazo[1,2-a]pyridines
WO2008071765A1 (en)	2008-06-19	Pharmaceutically active spiro-substituted benzimidazole derivatives
AU2005243434A1 (en)	2005-11-24	7-substituted benzimidazoles and their use as inhibitors of gastric acid secretion
EP1758900B1 (en)	2007-10-03	Substituted tricyclic benzimidazoles
WO2008017466A1 (en)	2008-02-14	Pharmaceutically active tetrahydroisoquinoline-substituted benzimidazole derivatives
WO2008084067A2 (en)	2008-07-17	Pharmaceutically active dihydrobenzofurane-substituted benzimidazole derivatives
CA2589448A1 (en)	2006-06-15	Substituted imidazo[4,5-b]pyridines as inhibitors of gastric acid secretion
WO2006134112A1 (en)	2006-12-21	Spiro-imidaznaphthyridine derivatives as gastric acid secretion inhibitors
NZ535685A (en)	2007-04-27	Preparation of 2-(7-chloro-1,8-napthyridine-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isindolinone, or pagoclone - a GABA receptor ligand
WO2008095912A2 (en)	2008-08-14	Enantiopure pharmacologically active tricyclic benzimidazoles
WO2008071766A2 (en)	2008-06-19	Spiro-indene substituted imidazonaphythyridine and pyranoimidazopyridine derivatives as inhibitors of gastric acid secretion
CA2563759A1 (en)	2005-11-03	6,7-dihydroxy-8-phenyl-3,6,7,8-tetrahydro-chromeno[7, 8-d]imidazole derivatives and their use as gastric acid secretion inhibitors

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