ES2345726T3 - Bencimidazoles sustituidos con cromano y su uso como inhibidores de la bomba acida. - Google Patents
Bencimidazoles sustituidos con cromano y su uso como inhibidores de la bomba acida. Download PDFInfo
- Publication number
- ES2345726T3 ES2345726T3 ES06831708T ES06831708T ES2345726T3 ES 2345726 T3 ES2345726 T3 ES 2345726T3 ES 06831708 T ES06831708 T ES 06831708T ES 06831708 T ES06831708 T ES 06831708T ES 2345726 T3 ES2345726 T3 ES 2345726T3
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- Spain
- Prior art keywords
- group
- reaction
- compound
- alkyl
- hydroxy
- Prior art date
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- 239000002253 acid Substances 0.000 title description 92
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical group C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title description 4
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 253
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 83
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 43
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 36
- 125000001424 substituent group Chemical group 0.000 claims abstract description 35
- 150000001408 amides Chemical class 0.000 claims abstract description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
- 125000005843 halogen group Chemical group 0.000 claims abstract description 20
- 239000000651 prodrug Substances 0.000 claims abstract description 16
- 229940002612 prodrug Drugs 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
- 125000003277 amino group Chemical group 0.000 claims abstract description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 238000001727 in vivo Methods 0.000 claims abstract description 6
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- 230000002496 gastric effect Effects 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- FAPVGICIAUIMRB-UHFFFAOYSA-N 7-[(5-fluoro-3,4-dihydro-2h-chromen-4-yl)oxy]-n,n,2-trimethyl-3h-benzimidazole-5-carboxamide Chemical compound C1COC2=CC=CC(F)=C2C1OC1=C(N=C(C)N2)C2=CC(C(=O)N(C)C)=C1 FAPVGICIAUIMRB-UHFFFAOYSA-N 0.000 claims description 11
- HCEFDOZABLDEGR-UHFFFAOYSA-N [7-[(5,7-difluoro-3,4-dihydro-2h-chromen-4-yl)oxy]-2-methyl-3h-benzimidazol-5-yl]-pyrrolidin-1-ylmethanone Chemical compound C1=C2NC(C)=NC2=C(OC2C3=C(F)C=C(F)C=C3OCC2)C=C1C(=O)N1CCCC1 HCEFDOZABLDEGR-UHFFFAOYSA-N 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 10
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 9
- 125000002393 azetidinyl group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 201000006549 dyspepsia Diseases 0.000 claims description 5
- CLIQCDHNPDMGSL-UHFFFAOYSA-N 7-[(5,7-difluoro-3,4-dihydro-2h-chromen-4-yl)oxy]-n,n,2-trimethyl-3h-benzimidazole-5-carboxamide Chemical compound C1COC2=CC(F)=CC(F)=C2C1OC1=C(N=C(C)N2)C2=CC(C(=O)N(C)C)=C1 CLIQCDHNPDMGSL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229940121353 acid pump inhibitor Drugs 0.000 claims description 3
- 208000010643 digestive system disease Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 3
- 208000019505 Deglutition disease Diseases 0.000 claims description 2
- 208000007882 Gastritis Diseases 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 206010019375 Helicobacter infections Diseases 0.000 claims description 2
- 208000005206 Laryngopharyngeal Reflux Diseases 0.000 claims description 2
- 206010028813 Nausea Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 206010030216 Oesophagitis Diseases 0.000 claims description 2
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 2
- 206010067869 Reflux laryngitis Diseases 0.000 claims description 2
- 206010039424 Salivary hypersecretion Diseases 0.000 claims description 2
- 208000008630 Sialorrhea Diseases 0.000 claims description 2
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 2
- 208000025865 Ulcer Diseases 0.000 claims description 2
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000000718 duodenal ulcer Diseases 0.000 claims description 2
- 208000006881 esophagitis Diseases 0.000 claims description 2
- 201000005917 gastric ulcer Diseases 0.000 claims description 2
- 201000000052 gastrinoma Diseases 0.000 claims description 2
- 208000029493 gastroesophageal disease Diseases 0.000 claims description 2
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 2
- 230000008693 nausea Effects 0.000 claims description 2
- 208000011906 peptic ulcer disease Diseases 0.000 claims description 2
- 231100000397 ulcer Toxicity 0.000 claims description 2
- 208000009935 visceral pain Diseases 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- 125000006823 (C1-C6) acyl group Chemical group 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 362
- 239000002904 solvent Substances 0.000 description 164
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- -1 2-thiazolyl Chemical group 0.000 description 108
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
- 239000000203 mixture Substances 0.000 description 93
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 85
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 238000000034 method Methods 0.000 description 67
- 239000003153 chemical reaction reagent Substances 0.000 description 64
- 239000002585 base Chemical class 0.000 description 59
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000007858 starting material Substances 0.000 description 57
- 239000000243 solution Substances 0.000 description 55
- 239000007787 solid Substances 0.000 description 53
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 44
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 35
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- 125000006239 protecting group Chemical group 0.000 description 30
- 238000012360 testing method Methods 0.000 description 29
- 210000004027 cell Anatomy 0.000 description 28
- 239000003795 chemical substances by application Substances 0.000 description 28
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 25
- 239000003054 catalyst Substances 0.000 description 25
- 229910052763 palladium Inorganic materials 0.000 description 25
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 24
- 150000002170 ethers Chemical class 0.000 description 24
- 238000009472 formulation Methods 0.000 description 24
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 22
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 22
- 150000007513 acids Chemical class 0.000 description 21
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- 239000003814 drug Substances 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 229910052783 alkali metal Inorganic materials 0.000 description 19
- 239000012046 mixed solvent Substances 0.000 description 19
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- 150000002825 nitriles Chemical class 0.000 description 18
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
- 229940079593 drug Drugs 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 230000003287 optical effect Effects 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 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 16
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 16
- 206010067482 No adverse event Diseases 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 235000011054 acetic acid Nutrition 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 16
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 16
- 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 16
- 150000001298 alcohols Chemical class 0.000 description 15
- 239000005557 antagonist Substances 0.000 description 15
- 229960004592 isopropanol Drugs 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 150000003462 sulfoxides Chemical class 0.000 description 15
- 239000003826 tablet Substances 0.000 description 15
- 239000000872 buffer Substances 0.000 description 14
- 230000005764 inhibitory process Effects 0.000 description 14
- 238000001228 spectrum Methods 0.000 description 14
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 13
- 238000010511 deprotection reaction Methods 0.000 description 13
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- 239000003638 chemical reducing agent Substances 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 12
- 238000010828 elution Methods 0.000 description 11
- 230000002140 halogenating effect Effects 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 11
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 10
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 10
- 230000009858 acid secretion Effects 0.000 description 10
- 230000002411 adverse Effects 0.000 description 10
- 150000008282 halocarbons Chemical class 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 238000011534 incubation Methods 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- 238000001990 intravenous administration Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 10
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 9
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 9
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
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| WO2009000413A1 (en) * | 2007-06-26 | 2008-12-31 | Sanofi-Aventis | A regioselective copper catalyzed synthesis of benzimidazoles and azabenzimidazoles |
| JP5802898B2 (ja) * | 2009-07-09 | 2015-11-04 | ラクオリア創薬株式会社 | 消化管運動異常が関与する疾患を治療するためのアシッドポンプ拮抗剤 |
| KR101472686B1 (ko) | 2013-07-09 | 2014-12-16 | 씨제이헬스케어 주식회사 | 벤즈이미다졸 유도체의 제조방법 |
| KR102084185B1 (ko) | 2013-08-29 | 2020-03-04 | 주식회사 대웅제약 | 테트라히드로사이클로펜타피롤 유도체 및 이의 제조방법 |
| KR102129842B1 (ko) * | 2013-10-02 | 2020-07-06 | 주식회사 대웅제약 | 술포닐인돌 유도체 및 이의 제조방법 |
| RU2693484C1 (ru) | 2013-11-22 | 2019-07-03 | СиЭль БАЙОСАЕНСИЗ ЭлЭлСи | Антагонисты гастрина для лечения и профилактики остеопороза |
| CN105440016B (zh) * | 2014-08-11 | 2018-08-31 | 江苏柯菲平医药股份有限公司 | 吲哚、氮杂吲哚类衍生物、其制备方法及其在医药上的应用 |
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| KR101613245B1 (ko) | 2015-04-27 | 2016-04-18 | 주식회사 대웅제약 | 신규의 4-메톡시 피롤 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 |
| SI3305291T1 (sl) * | 2015-06-08 | 2021-08-31 | Hk Inno.N Corporation | Uporabe benzimidazolnega derivata za nočno izločanje kisline |
| KR101769204B1 (ko) * | 2015-08-04 | 2017-08-17 | 씨제이헬스케어 주식회사 | 크로마놀 유도체의 신규한 제조방법 |
| KR101777971B1 (ko) | 2016-07-05 | 2017-09-12 | 제일약품주식회사 | 이미다조[1,2-a]피리딘 유도체, 이의 제조방법 및 이의 용도 |
| KR101829685B1 (ko) * | 2016-07-28 | 2018-02-19 | 씨제이헬스케어 주식회사 | 안정성 및 용해도가 개선된 주사용 조성물 |
| KR101829705B1 (ko) * | 2016-09-21 | 2018-02-19 | 씨제이헬스케어 주식회사 | 안정성이 향상된 주사용 조성물 |
| KR101829706B1 (ko) * | 2016-09-21 | 2018-02-19 | 씨제이헬스케어 주식회사 | 벤즈이미다졸 유도체의 산부가염 |
| US11142591B2 (en) * | 2016-12-20 | 2021-10-12 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| KR101960357B1 (ko) | 2016-12-26 | 2019-03-20 | 씨제이헬스케어 주식회사 | 벤즈이미다졸 유도체를 포함하는 신규한 제제 |
| KR102233456B1 (ko) * | 2017-05-31 | 2021-03-29 | 주식회사 대웅제약 | 4-메톡시피롤 유도체의 중간체 제조 방법 |
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| TWI676477B (zh) * | 2017-12-05 | 2019-11-11 | 南韓商Ｃｊ醫藥健康股份有限公司 | 苯并咪唑衍生物用於夜間酸突破的用途 |
| JOP20190198A1 (ar) * | 2018-08-28 | 2020-02-28 | Hk Inno N Corp | تركيبة صيدلانية تشتمل على عامل مضاد للصفيحات ومثبط إفراز حمض معدي |
| JOP20190201A1 (ar) * | 2018-08-29 | 2020-02-29 | Hk Inno N Corp | تركيبة لاستئصال الملوية البوابية |
| CN109320485B (zh) * | 2018-12-02 | 2021-06-18 | 江苏慧聚药业有限公司 | 合成特戈拉赞手性醇的方法 |
| JP2022520276A (ja) | 2019-02-18 | 2022-03-29 | エイチケー イノ．エヌ コーポレーション | ベンズイミダゾール誘導体化合物を含む医薬組成物 |
| CN112851646B (zh) * | 2019-11-12 | 2023-06-13 | 中国医学科学院药物研究所 | 特戈拉赞的制备方法 |
| UY39094A (es) * | 2020-02-27 | 2021-07-30 | Hk Inno N Corp | Composición farmacéutica que comprende compuesto derivado de bencimidazol |
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| CN116507318A (zh) * | 2020-10-23 | 2023-07-28 | 怡诺安有限公司 | 包含苯并咪唑衍生物化合物的口服崩解片剂及其制备方法 |
| CN112358450A (zh) * | 2020-11-19 | 2021-02-12 | 南京艾康生物科技有限公司 | 一种4-(苄氧基)-2-甲基-1H-苯并[d]咪唑-6-羧酸的合成方法 |
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| CN113527272B (zh) * | 2021-08-06 | 2023-07-21 | 西安淳甄新材料有限公司 | 一种特戈拉赞的合成方法 |
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| WO2024045255A1 (zh) * | 2022-08-30 | 2024-03-07 | 上海皓元医药股份有限公司 | 一种特戈拉赞晶型b及其制备方法 |
| 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 |
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| CN116253685B (zh) * | 2022-12-30 | 2024-12-10 | 成都安满生物医药科技有限公司 | 一种特戈拉赞中间体的制备方法 |
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| KR20250164238A (ko) * | 2023-04-07 | 2025-11-24 | 제이더블유중외제약 주식회사 | 벤즈이미다졸 유도체의 염 |
| CN116621821A (zh) * | 2023-05-29 | 2023-08-22 | 宙晟智维生命科学(上海)有限公司 | 一种无定形的苯并咪唑基化合物及固体分散体 |
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| CN116715660A (zh) * | 2023-06-14 | 2023-09-08 | 上海柏狮生物科技有限公司 | 一种特格拉赞的无定型物及其制备方法 |
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| CN117903097A (zh) * | 2024-01-04 | 2024-04-19 | 浙江永太科技股份有限公司 | 一种特戈拉赞关键中间体母液料的回收方法 |
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- 2006-12-06 ES ES06831708T patent/ES2345726T3/es active Active
- 2006-12-06 CN CN2006800479255A patent/CN101341149B/zh active Active
- 2006-12-06 BR BR122020004679-1A patent/BR122020004679B1/pt not_active IP Right Cessation
- 2006-12-06 JP JP2008546663A patent/JP4481344B2/ja active Active
- 2006-12-06 WO PCT/IB2006/003605 patent/WO2007072146A1/en not_active Ceased
- 2006-12-13 NL NL2000371A patent/NL2000371C2/nl not_active IP Right Cessation
- 2006-12-18 GT GT200600514A patent/GT200600514A/es unknown
- 2006-12-18 PE PE2006001625A patent/PE20071182A1/es not_active Application Discontinuation
- 2006-12-18 TW TW095147456A patent/TW200732326A/zh unknown
- 2006-12-18 DO DO2006000285A patent/DOP2006000285A/es unknown
- 2006-12-19 US US11/612,583 patent/US7723321B2/en active Active
- 2006-12-19 UY UY30043A patent/UY30043A1/es not_active Application Discontinuation
- 2006-12-19 AR ARP060105611A patent/AR058120A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR101088247B1 (ko) | 2011-11-30 |
| WO2007072146A1 (en) | 2007-06-28 |
| CN101341149B (zh) | 2011-06-08 |
| US20070142448A1 (en) | 2007-06-21 |
| US7723321B2 (en) | 2010-05-25 |
| BRPI0620081B1 (pt) | 2020-10-20 |
| DOP2006000285A (es) | 2007-07-31 |
| UY30043A1 (es) | 2007-07-31 |
| NL2000371C2 (nl) | 2007-09-06 |
| TW200732326A (en) | 2007-09-01 |
| PE20071182A1 (es) | 2008-02-07 |
| BRPI0620081B8 (pt) | 2021-05-25 |
| JP4481344B2 (ja) | 2010-06-16 |
| NL2000371A1 (nl) | 2007-06-20 |
| AR058120A1 (es) | 2008-01-23 |
| BRPI0620081A2 (pt) | 2011-11-01 |
| CN101341149A (zh) | 2009-01-07 |
| CA2631880A1 (en) | 2007-06-28 |
| DE602006014996D1 (de) | 2010-07-29 |
| CA2631880C (en) | 2011-03-29 |
| CN102321077A (zh) | 2012-01-18 |
| ATE471319T1 (de) | 2010-07-15 |
| JP2009520017A (ja) | 2009-05-21 |
| EP1963311B1 (en) | 2010-06-16 |
| EP1963311A1 (en) | 2008-09-03 |
| HK1125368A1 (en) | 2009-08-07 |
| BR122020004679B1 (pt) | 2021-09-21 |
| GT200600514A (es) | 2007-07-17 |
| KR20080080195A (ko) | 2008-09-02 |
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