CA2601388A1 - Benzimidazoles tricycliques substitues par des groupements thioamide utilises dans le traitement de maladies gastro-intestinales - Google Patents

Benzimidazoles tricycliques substitues par des groupements thioamide utilises dans le traitement de maladies gastro-intestinales Download PDF

Info

Publication number: CA2601388A1
Authority: CA; Canada
Prior art keywords: alkyl; hydrogen; alkoxy; cycloalkyl; hydroxy
Prior art date: 2005-03-24
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

CA002601388A

Other languages

English (en)

Inventor

Maria Vittoria Chiesa

Peter Jan Zimmermann

Wilm Buhr

Christof Brehm

Andreas Palmer

Wolfgang-Alexander Simon

Wolfgang Kromer

Stefan Postius

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.)

2005-03-24

Filing date

2006-03-22

Publication date

2006-09-28

2006-03-22 Application filed by Individual filed Critical Individual

2006-09-28 Publication of CA2601388A1 publication Critical patent/CA2601388A1/fr

Status Abandoned legal-status Critical Current

Links

238000011282 treatment Methods 0.000 title claims description 12
208000018522 Gastrointestinal disease Diseases 0.000 title claims description 6
150000001556 benzimidazoles Chemical class 0.000 title description 6
-1 cyclic benzimidazoles Chemical class 0.000 claims abstract description 185
150000001875 compounds Chemical class 0.000 claims abstract description 126
125000001424 substituent group Chemical group 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 155
239000001257 hydrogen Substances 0.000 claims description 155
150000002431 hydrogen Chemical group 0.000 claims description 106
150000003839 salts Chemical class 0.000 claims description 44
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical group 0.000 claims description 33
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
229910052760 oxygen Inorganic materials 0.000 claims description 25
239000001301 oxygen Substances 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
239000003814 drug Substances 0.000 claims description 15
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
229910052786 argon Inorganic materials 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
AKJSCQMPNSTLED-KRWDZBQOSA-N (8s)-n,2,3-trimethyl-8-phenyl-7,8-dihydro-6h-pyrano[2,3-e]benzimidazole-5-carbothioamide Chemical compound C1([C@H]2OC=3C=4N=C(C)N(C)C=4C=C(C=3CC2)C(=S)NC)=CC=CC=C1 AKJSCQMPNSTLED-KRWDZBQOSA-N 0.000 claims description 2
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
BYOHQUNTHPAULF-UHFFFAOYSA-N n,n,2,3-tetramethyl-8-phenyl-7,8-dihydro-6h-pyrano[2,3-e]benzimidazole-5-carbothioamide Chemical compound C1CC=2C(C(=S)N(C)C)=CC=3N(C)C(C)=NC=3C=2OC1C1=CC=CC=C1 BYOHQUNTHPAULF-UHFFFAOYSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
RMVKLCVFEVVQTR-FERBBOLQSA-N CC1=NC2=C(N1C)C=C(C=1CCC(OC12)C1=CC=CC=C1)C(O)=S.CN(C(=S)C=1C=2CC[C@H](OC2C2=C(N(C(=N2)C)C)C1)C1=CC=CC=C1)C Chemical compound CC1=NC2=C(N1C)C=C(C=1CCC(OC12)C1=CC=CC=C1)C(O)=S.CN(C(=S)C=1C=2CC[C@H](OC2C2=C(N(C(=N2)C)C)C1)C1=CC=CC=C1)C RMVKLCVFEVVQTR-FERBBOLQSA-N 0.000 claims 1
BSVCNNXAJWYGER-UHFFFAOYSA-N CN(C)C(C(C(CC1)=C2OC1C1=CC=CC=C1)=CC1=C2N=C(C2CC2)N1C)=S.NC1CC1 Chemical compound CN(C)C(C(C(CC1)=C2OC1C1=CC=CC=C1)=CC1=C2N=C(C2CC2)N1C)=S.NC1CC1 BSVCNNXAJWYGER-UHFFFAOYSA-N 0.000 claims 1
FEAMWTXVTYKPBL-IBGZPJMESA-N azetidin-1-yl-[(8s)-2,3-dimethyl-8-phenyl-7,8-dihydro-6h-pyrano[2,3-e]benzimidazol-5-yl]methanethione Chemical compound C([C@H](OC1=C2N=C(N(C2=C2)C)C)C=3C=CC=CC=3)CC1=C2C(=S)N1CCC1 FEAMWTXVTYKPBL-IBGZPJMESA-N 0.000 claims 1
230000002496 gastric effect Effects 0.000 abstract description 9
230000000968 intestinal effect Effects 0.000 abstract description 5
230000002401 inhibitory effect Effects 0.000 abstract description 3
230000001681 protective effect Effects 0.000 abstract description 3
230000028327 secretion Effects 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 33
239000007787 solid Substances 0.000 description 26
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
239000000203 mixture Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
238000001816 cooling Methods 0.000 description 14
239000000725 suspension Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000012044 organic layer Substances 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 10
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
239000010410 layer Substances 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
238000000034 method Methods 0.000 description 9
WDYGPMAMBXJESZ-SFHVURJKSA-N (2s)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-SFHVURJKSA-N 0.000 description 8
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
JRTHAKOHBMETRC-UHFFFAOYSA-N [3-[4-bis(3,5-dimethylphenyl)phosphanyl-2,6-dimethoxypyridin-3-yl]-2,6-dimethoxypyridin-4-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound COC=1N=C(OC)C=C(P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)C=1C=1C(OC)=NC(OC)=CC=1P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 JRTHAKOHBMETRC-UHFFFAOYSA-N 0.000 description 7
229960004132 diethyl ether Drugs 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000000126 substance Substances 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
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201000010099 disease Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
229940126409 proton pump inhibitor Drugs 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
108010079943 Pentagastrin Proteins 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000012317 TBTU Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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 3
230000009858 acid secretion Effects 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
ALXRNCVIQSDJAO-KRCBVYEFSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCNC(=O)OCC(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ALXRNCVIQSDJAO-KRCBVYEFSA-N 0.000 description 3
229960000444 pentagastrin Drugs 0.000 description 3
229940126535 potassium competitive acid blocker Drugs 0.000 description 3
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
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KJIWUXWUMQXMOY-QHCPKHFHSA-N (8s)-n,n,2-trimethyl-8-phenyl-3-(2-trimethylsilylethoxymethyl)-7,8-dihydro-6h-pyrano[2,3-e]benzimidazole-5-carboxamide Chemical compound C1([C@H]2OC=3C=4N=C(C)N(COCC[Si](C)(C)C)C=4C=C(C=3CC2)C(=O)N(C)C)=CC=CC=C1 KJIWUXWUMQXMOY-QHCPKHFHSA-N 0.000 description 2
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 2
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PVYGAIPLAHJVJB-UHFFFAOYSA-N 7-hydroxy-n,2,3-trimethyl-6-(3-oxo-3-phenylpropyl)benzimidazole-5-carboxamide Chemical compound CNC(=O)C1=CC=2N(C)C(C)=NC=2C(O)=C1CCC(=O)C1=CC=CC=C1 PVYGAIPLAHJVJB-UHFFFAOYSA-N 0.000 description 2
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PVUIMNQVLPNOBC-UHFFFAOYSA-N 7-hydroxy-n,n,2-trimethyl-6-(3-oxo-3-phenylpropyl)-3-(2-trimethylsilylethoxymethyl)benzimidazole-5-carboxamide Chemical compound CN(C)C(=O)C1=CC=2N(COCC[Si](C)(C)C)C(C)=NC=2C(O)=C1CCC(=O)C1=CC=CC=C1 PVUIMNQVLPNOBC-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA002601388A 2005-03-24 2006-03-22 Benzimidazoles tricycliques substitues par des groupements thioamide utilises dans le traitement de maladies gastro-intestinales Abandoned CA2601388A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
EP05102407		2005-03-24
EP05102407.3		2005-03-24
EP05107518		2005-08-16
EP05107518.2		2005-08-16
PCT/EP2006/060936 WO2006100255A1 (fr)	2005-03-24	2006-03-22	Benzimidazoles tricycliques substitués par des groupements thioamide utilisés dans le traitement de maladies gastro-intestinales

Publications (1)

Publication Number	Publication Date
CA2601388A1 true CA2601388A1 (fr)	2006-09-28

Family

ID=36571028

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002601388A Abandoned CA2601388A1 (fr)	2005-03-24	2006-03-22	Benzimidazoles tricycliques substitues par des groupements thioamide utilises dans le traitement de maladies gastro-intestinales

Country Status (5)

Country	Link
EP (1)	EP1863820A1 (fr)
JP (1)	JP2008534476A (fr)
AU (1)	AU2006226352A1 (fr)
CA (1)	CA2601388A1 (fr)
WO (1)	WO2006100255A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8466166B2 (en)	2006-09-21	2013-06-18	Raqualia Pharma Inc.	Benzimidazole derivatives as selective acid pump inhibitors
WO2008074858A1 (fr) *	2006-12-21	2008-06-26	Nycomed Gmbh	Intermédiaires et procédé pour la production de benzimidazoles tricycliques substitués en position 5
WO2008114123A1 (fr) *	2007-03-21	2008-09-25	Raqualia Pharma Inc.	Dérivés de spiro benzimidazole comme inhibiteurs de pompe à acide
CN102470126A (zh)	2009-07-09	2012-05-23	拉夸里亚创药株式会社	用于治疗与异常肠胃运动有关的疾病的酸泵拮抗剂

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2004226180A1 (en) *	2003-04-04	2004-10-14	Altana Pharma Ag	Cyclic benzimidazoles

2006
- 2006-03-22 AU AU2006226352A patent/AU2006226352A1/en not_active Abandoned
- 2006-03-22 CA CA002601388A patent/CA2601388A1/fr not_active Abandoned
- 2006-03-22 JP JP2008502403A patent/JP2008534476A/ja active Pending
- 2006-03-22 WO PCT/EP2006/060936 patent/WO2006100255A1/fr not_active Ceased
- 2006-03-22 EP EP06725220A patent/EP1863820A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
WO2006100255A1 (fr)	2006-09-28
JP2008534476A (ja)	2008-08-28
AU2006226352A1 (en)	2006-09-28
EP1863820A1 (fr)	2007-12-12

Publication	Publication Date	Title
US20080113963A1 (en)	2008-05-15	Cyclic benzimidazoles
EP1419163A1 (fr)	2004-05-19	Imidazopyridines tricycliques
US20080113962A1 (en)	2008-05-15	Condensed Tricyclic Benzimidazoles For the Treatment of Gastrointestinal Disorders
AU2004213177A1 (en)	2004-09-02	6-substituted imidazopyrazines
CA2601388A1 (fr)	2006-09-28	Benzimidazoles tricycliques substitues par des groupements thioamide utilises dans le traitement de maladies gastro-intestinales
US20060194782A1 (en)	2006-08-31	Pharmacologically active imidazo[4,5-c] pyridines
US20080033006A1 (en)	2008-02-07	1,2,4-Triazolo&lsqb; 1,5-A&rsqb; Pyridines as Gastric Acid Secretion Inhibitors
EP1797089A1 (fr)	2007-06-20	Benzimidazoles tricycliques substitués
EP1718648B1 (fr)	2008-04-23	Imidazolpyridines tricycliques et intermediaires pour leur synthese
CA2452801A1 (fr)	2003-02-27	Imidazopyridines a substitution alkyle pour le traitement des troubles gastro-intestinaux
EP1718646A1 (fr)	2006-11-08	1,2,4-triazolo[4,3-a]pyridines destinees au traitement des pathologies du systeme gastrointestinal
US20070203114A1 (en)	2007-08-30	7,8,9,10-Tetrahydro-Imidazo [2,1-A] Isochinolines
EP1776361A1 (fr)	2007-04-25	1h-pyrroloý3,2-b¨pyridines 5-substituees
HK1088898B (en)	2009-05-22	Cyclic benzimidazoles
AU2002333289A1 (en)	2003-02-24	Tricyclic imidazopyridines

Legal Events

Date	Code	Title	Description
2010-03-22	FZDE	Dead