SK212001A3 - Thiobenzimidazole derivatives - Google Patents
Thiobenzimidazole derivatives Download PDFInfo
- Publication number
- SK212001A3 SK212001A3 SK21-2001A SK212001A SK212001A3 SK 212001 A3 SK212001 A3 SK 212001A3 SK 212001 A SK212001 A SK 212001A SK 212001 A3 SK212001 A3 SK 212001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- cooh
- substituted
- carbon atoms
- unsubstituted
- Prior art date
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- KSAPYRIVHFAQGR-UHFFFAOYSA-N 1-sulfanylbenzimidazole Chemical class C1=CC=C2N(S)C=NC2=C1 KSAPYRIVHFAQGR-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 101000909983 Homo sapiens Chymase Proteins 0.000 claims abstract description 13
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- 230000003449 preventive effect Effects 0.000 claims abstract description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 922
- 125000004432 carbon atom Chemical group C* 0.000 claims description 112
- -1 phenoxy, phenoxy Chemical group 0.000 claims description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 239000001301 oxygen Substances 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910005965 SO 2 Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 150000003536 tetrazoles Chemical class 0.000 claims description 10
- 125000004951 trihalomethoxy group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 210000000988 bone and bone Anatomy 0.000 claims description 5
- 230000004097 bone metabolism Effects 0.000 claims description 5
- 230000008414 cartilage metabolism Effects 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 208000030159 metabolic disease Diseases 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 150000003931 anilides Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical compound O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 claims description 3
- IGAVZWMNOPFOCW-UHFFFAOYSA-N 2h-1,2,4-thiadiazol-5-one Chemical compound O=C1NC=NS1 IGAVZWMNOPFOCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000000241 respiratory effect Effects 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000002554 disease preventive effect Effects 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 149
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
- 239000000460 chlorine Substances 0.000 description 71
- 239000000203 mixture Substances 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 45
- 239000000243 solution Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 15
- 150000001556 benzimidazoles Chemical class 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 238000010189 synthetic method Methods 0.000 description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 11
- 229960003881 letrozole Drugs 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000003889 eye drop Substances 0.000 description 9
- 229940012356 eye drops Drugs 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000005711 Benzoic acid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 108090000227 Chymases Proteins 0.000 description 6
- 102000003858 Chymases Human genes 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- PHRABVHYUHIYGY-UHFFFAOYSA-N 1-methylnaphthalene Chemical group C1=CC=C2C([CH2])=CC=CC2=C1 PHRABVHYUHIYGY-UHFFFAOYSA-N 0.000 description 4
- CKUXMYYDAQIJRQ-UHFFFAOYSA-N 5,6-dimethyl-1,3-dihydrobenzimidazole-2-thione Chemical compound C1=C(C)C(C)=CC2=C1NC(=S)N2 CKUXMYYDAQIJRQ-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- QKASDIPENBEWBU-UHFFFAOYSA-N methyl 2-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CBr QKASDIPENBEWBU-UHFFFAOYSA-N 0.000 description 4
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- MMPXKUSIQTTZCJ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C=CN=C1 MMPXKUSIQTTZCJ-UHFFFAOYSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
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- 238000004440 column chromatography Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- FLDMWRZKOSGMIS-UHFFFAOYSA-N methyl 2-[(5,6-dimethyl-1h-benzimidazol-2-yl)sulfanylmethyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1CSC1=NC2=CC(C)=C(C)C=C2N1 FLDMWRZKOSGMIS-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P11/06—Antiasthmatics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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- Life Sciences & Earth Sciences (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20025098 | 1998-07-15 | ||
| PCT/JP1999/003799 WO2000003997A1 (fr) | 1998-07-15 | 1999-07-14 | Derives de thiobenzimidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK212001A3 true SK212001A3 (en) | 2001-11-06 |
Family
ID=16421274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK21-2001A SK212001A3 (en) | 1998-07-15 | 1999-07-14 | Thiobenzimidazole derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7268145B2 (hu) |
| EP (1) | EP1097926A4 (hu) |
| JP (1) | JP3923255B2 (hu) |
| KR (1) | KR100903531B1 (hu) |
| CN (1) | CN1187337C (hu) |
| AU (1) | AU758789B2 (hu) |
| BG (1) | BG65514B1 (hu) |
| BR (1) | BR9912098A (hu) |
| CA (1) | CA2336909C (hu) |
| EE (1) | EE04904B1 (hu) |
| HR (1) | HRP20010030A2 (hu) |
| HU (1) | HUP0103256A3 (hu) |
| ID (1) | ID26899A (hu) |
| IL (1) | IL140862A (hu) |
| IS (1) | IS5807A (hu) |
| NO (1) | NO318957B1 (hu) |
| NZ (1) | NZ509207A (hu) |
| PL (1) | PL203730B1 (hu) |
| RU (1) | RU2237663C2 (hu) |
| SK (1) | SK212001A3 (hu) |
| TR (1) | TR200100047T2 (hu) |
| WO (1) | WO2000003997A1 (hu) |
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| US20040010004A1 (en) | 2000-01-17 | 2004-01-15 | Naoki Tsuchiya | Benzimidazole derivatives |
| JP2007119478A (ja) * | 1998-07-15 | 2007-05-17 | Teijin Ltd | チオベンズイミダゾール誘導体 |
| DE60130865T2 (de) * | 2000-01-17 | 2008-07-17 | Teijin Pharma Ltd. | Benzimidazol-derivate als menschliche chymase - inhibitoren |
| AU783839B2 (en) * | 2000-01-17 | 2005-12-15 | Teijin Limited | Human chymase inhibitors |
| US7618977B2 (en) | 2000-02-22 | 2009-11-17 | Asubio Pharma Co., Ltd. | Method of treating dermatitis comprising administering a chymase inhibitor |
| ATE376830T1 (de) * | 2001-02-22 | 2007-11-15 | Teijin Pharma Ltd | Benzo(b(thiophenderivate und verfahren zu deren herstellung |
| JP4759500B2 (ja) * | 2001-02-22 | 2011-08-31 | 帝人株式会社 | ベンゾ［ｂ］チオフェン誘導体、およびその製造方法 |
| AU2003281039A1 (en) * | 2002-07-10 | 2004-02-02 | Sumitomo Pharmaceuticals Co., Ltd. | Imidazole derivative |
| CL2004001034A1 (es) * | 2003-05-14 | 2005-03-28 | Teijin Pharma Ltd | Formas cristalinas de acido 4-(1-((,etilbenzotiofen-3-il)me til)benzimidazol-2-iltio)butanoico; procedimiento de preparacion de las formas cristalinas; composicion farmaceutica; y su uso para el tratamiento de enfermedades inflamatorias, alergicas, r |
| US20070032466A1 (en) * | 2003-08-22 | 2007-02-08 | Teijin Pharma Limited | Drug containing chymase inhibitor as the active ingredient |
| RU2409569C2 (ru) * | 2004-08-26 | 2011-01-20 | Актелион Фармасьютиклз Лтд | Производные 2-сульфанилбензимидазол-1-илуксусной кислоты в качестве антагонистов crth2 |
| EP1826207A4 (en) * | 2004-11-12 | 2009-05-20 | Teijin Pharma Ltd | ACID SALT OF A BENZIMIDAZOLE DERIVATIVE AND CRYSTAL THEREOF |
| UA95788C2 (en) * | 2005-12-15 | 2011-09-12 | Ф. Хоффманн-Ля Рош Аг | Fused pyrrole derivatives |
| JP4339371B2 (ja) * | 2007-03-22 | 2009-10-07 | 株式会社ソニー・コンピュータエンタテインメント | 情報処理装置および情報処理方法 |
| TW200916098A (en) * | 2007-06-14 | 2009-04-16 | Teijin Pharma Ltd | Agent for lowering uric acid level |
| WO2009133964A1 (ja) * | 2008-04-28 | 2009-11-05 | 国立大学法人九州大学 | 酸化ストレス抑制剤 |
| WO2010036613A1 (en) | 2008-09-26 | 2010-04-01 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| MX2011004258A (es) | 2008-10-22 | 2011-06-01 | Merck Sharp & Dohme | Derivados de bencimidazol ciclicos novedosos utiles como agentes anti-diabeticos. |
| AU2009309007A1 (en) | 2008-10-29 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CA2741672A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| CN105001219A (zh) | 2011-02-25 | 2015-10-28 | 默沙东公司 | 用作抗糖尿病药剂的新的环状氮杂苯并咪唑衍生物 |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| RU2015106909A (ru) | 2012-08-02 | 2016-09-27 | Мерк Шарп И Доум Корп. | Антидиабетические трициклические соединения |
| US9527839B2 (en) | 2012-08-22 | 2016-12-27 | Merck Sharp & Dohme Corp. | Benzimidazole tetrahydropyran derivatives |
| US9382243B2 (en) | 2012-08-22 | 2016-07-05 | Merck Sharp & Dohme Corp. | Azabenzimidazole tetrahydropyran derivatives |
| WO2014031517A1 (en) | 2012-08-22 | 2014-02-27 | Merck Sharp & Dohme Corp. | Novel azabenzimidazole tetrahydrofuran derivatives |
| KR20150045436A (ko) | 2012-08-22 | 2015-04-28 | 머크 샤프 앤드 돔 코포레이션 | 신규 아자벤즈이미다졸 헥사히드로푸로[3,2-b]푸란 유도체 |
| ES2755087T3 (es) | 2012-08-22 | 2020-04-21 | Merck Sharp & Dohme | Derivados de benzimidazol hexahidrofuro[3,2-b]furano útiles como activadores de proteína cinasa activada por AMP |
| US9540364B2 (en) | 2012-08-22 | 2017-01-10 | Merck Sharp & Dohme Corp. | Benzimidazole tetrahydrofuran derivatives |
| KR101435496B1 (ko) * | 2012-10-22 | 2014-08-28 | 한국과학기술연구원 | 미토콘드리아 기능 조절제로서의 벤즈이미다졸 유도체 |
| US9650375B2 (en) | 2013-03-14 | 2017-05-16 | Merck Sharp & Dohme Corp. | Indole derivatives useful as anti-diabetic agents |
| JP6064062B2 (ja) | 2013-03-15 | 2017-01-18 | ファイザー・インク | Ａｍｐｋを活性化させるインダゾール化合物 |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| EP3068768B1 (en) | 2013-11-15 | 2019-07-31 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2015089809A1 (en) | 2013-12-19 | 2015-06-25 | Merck Sharp & Dohme Corp. | Antidiabetic substituted heteroaryl compounds |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
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-
1999
- 1999-07-14 TR TR2001/00047T patent/TR200100047T2/xx unknown
- 1999-07-14 CN CNB998108162A patent/CN1187337C/zh not_active Expired - Fee Related
- 1999-07-14 SK SK21-2001A patent/SK212001A3/sk unknown
- 1999-07-14 HU HU0103256A patent/HUP0103256A3/hu unknown
- 1999-07-14 EP EP99929832A patent/EP1097926A4/en not_active Withdrawn
- 1999-07-14 PL PL345540A patent/PL203730B1/pl not_active IP Right Cessation
- 1999-07-14 JP JP2000560104A patent/JP3923255B2/ja not_active Expired - Fee Related
- 1999-07-14 ID IDW20010090A patent/ID26899A/id unknown
- 1999-07-14 CA CA002336909A patent/CA2336909C/en not_active Expired - Fee Related
- 1999-07-14 AU AU46519/99A patent/AU758789B2/en not_active Ceased
- 1999-07-14 WO PCT/JP1999/003799 patent/WO2000003997A1/ja active IP Right Grant
- 1999-07-14 NZ NZ509207A patent/NZ509207A/xx not_active IP Right Cessation
- 1999-07-14 KR KR1020017000503A patent/KR100903531B1/ko not_active IP Right Cessation
- 1999-07-14 BR BR9912098-4A patent/BR9912098A/pt not_active Application Discontinuation
- 1999-07-14 IL IL14086299A patent/IL140862A/xx not_active IP Right Cessation
- 1999-07-14 EE EEP200100022A patent/EE04904B1/xx not_active IP Right Cessation
- 1999-07-14 RU RU2001104339A patent/RU2237663C2/ru not_active IP Right Cessation
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2001
- 2001-01-12 HR HR20010030A patent/HRP20010030A2/hr not_active Application Discontinuation
- 2001-01-12 NO NO20010193A patent/NO318957B1/no not_active IP Right Cessation
- 2001-01-12 IS IS5807A patent/IS5807A/is unknown
- 2001-01-15 BG BG105149A patent/BG65514B1/bg unknown
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2004
- 2004-10-14 US US10/963,710 patent/US7268145B2/en not_active Expired - Fee Related
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2007
- 2007-05-09 US US11/797,975 patent/US20070275995A1/en not_active Abandoned
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