NO314183B1 - Benzimidazol-derivater, anvendelse derav og farmasöytiske preparater inneholdende dem - Google Patents

Benzimidazol-derivater, anvendelse derav og farmasöytiske preparater inneholdende dem Download PDF

Info

Publication number: NO314183B1
Authority: NO; Norway
Prior art keywords: benzoimidazol; ethyl; compound; methyl; carboxamide
Prior art date: 1997-04-07

Application number

NO19994858A

Other languages

English (en)

Norwegian (no)

Other versions

NO994858L (no

NO994858D0 (no

Inventor

Timothy J Church

Neil Scott Cutshall

Anthony R Gangloff

Thomas E Jenkins

Martin S Linsell

Joane Litvak

Kenneth D Rice

Jeffrey R Spencer

Vivian Rueywen Wang

Original Assignee

Axys Pharm Corp

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.)

1997-04-07

Filing date

1999-10-06

Publication date

2003-02-10

1999-10-06 Application filed by Axys Pharm Corp filed Critical Axys Pharm Corp

1999-10-06 Publication of NO994858D0 publication Critical patent/NO994858D0/no

1999-12-06 Publication of NO994858L publication Critical patent/NO994858L/no

2003-02-10 Publication of NO314183B1 publication Critical patent/NO314183B1/no

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 15
229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 343
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 190
239000000203 mixture Substances 0.000 claims description 117
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 70
-1 1H-benzoimidazol-2-yl Chemical group 0.000 claims description 64
238000002360 preparation method Methods 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 33
238000011282 treatment Methods 0.000 claims description 29
239000005711 Benzoic acid Substances 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
235000010233 benzoic acid Nutrition 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 20
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 14
208000027866 inflammatory disease Diseases 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
125000006413 ring segment Chemical group 0.000 claims description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
239000000443 aerosol Substances 0.000 claims description 10
230000001225 therapeutic effect Effects 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 6
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
125000002883 imidazolyl group Chemical group 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
230000009385 viral infection Effects 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
MTWFINXLTMNGCU-UHFFFAOYSA-N 2-[2-[[3-methyl-2-[1-(4,6,7-trifluoro-1h-benzimidazol-2-yl)ethyl]benzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound N=1C2=C(F)C=C(F)C(F)=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=CC=C1C(O)=O MTWFINXLTMNGCU-UHFFFAOYSA-N 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
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PCCUPAKWDDHPKB-UHFFFAOYSA-N 5-chloro-2-[2-[[2-[1-[6-(diaminomethylideneamino)-1h-benzimidazol-2-yl]ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound N=1C2=CC(NC(N)=N)=CC=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=C(Cl)C=C1C(O)=O PCCUPAKWDDHPKB-UHFFFAOYSA-N 0.000 claims description 3
239000000048 adrenergic agonist Substances 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
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XMLXFJVPVNLPCA-UHFFFAOYSA-N 2-[[6-(diaminomethylideneamino)-1h-benzimidazol-2-yl]methyl]-3-methyl-n-(2-naphthalen-1-ylethyl)benzimidazole-5-carboxamide Chemical compound C1=CC=C2C(CCNC(=O)C3=CC=C4N=C(CC=5NC6=CC=C(NC(N)=N)C=C6N=5)N(C4=C3)C)=CC=CC2=C1 XMLXFJVPVNLPCA-UHFFFAOYSA-N 0.000 claims description 2
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125000004935 benzoxazolinyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
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229960001022 fenoterol Drugs 0.000 claims description 2
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BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 claims 1
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AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
BPNURUIODCTQOZ-UHFFFAOYSA-N ethyl 2-(4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridin-2-yl)propanoate;dihydrochloride Chemical compound Cl.Cl.C1NCCC2=C1N=C(C(C)C(=O)OCC)N2 BPNURUIODCTQOZ-UHFFFAOYSA-N 0.000 description 1
NJBQDVWIEPRPHW-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-(1-benzoyl-5-hydroxybenzimidazol-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2N(C3=CC=C(O)C=C3N=2)C(=O)C=2C=CC=CC=2)N2C)C2=C1 NJBQDVWIEPRPHW-UHFFFAOYSA-N 0.000 description 1
DPKAPNWVYIPCBL-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-(1h-benzimidazol-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2NC3=CC=CC=C3N=2)N2C)C2=C1 DPKAPNWVYIPCBL-UHFFFAOYSA-N 0.000 description 1
TUMCXNPKHLWKKM-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-(4,6-difluoro-5-imidazol-1-yl-1h-benzimidazol-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2NC3=CC(F)=C(C(F)=C3N=2)N2C=NC=C2)N2C)C2=C1 TUMCXNPKHLWKKM-UHFFFAOYSA-N 0.000 description 1
NMMOWXVAPQPWRR-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-(5,6-difluoro-1h-benzimidazol-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2NC3=CC(F)=C(F)C=C3N=2)N2C)C2=C1 NMMOWXVAPQPWRR-UHFFFAOYSA-N 0.000 description 1
VGISPJJHNIMLCZ-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-(5-ethanimidoyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)ethyl]-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)N1CC(N=C(N2)C(C)C=3NC=4CCN(CC=4N=3)C(C)=N)=C2CC1 VGISPJJHNIMLCZ-UHFFFAOYSA-N 0.000 description 1
ORLHGXKYNPNQAX-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-(6-fluoro-1h-benzimidazol-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2NC3=CC=C(F)C=C3N=2)N2C)C2=C1 ORLHGXKYNPNQAX-UHFFFAOYSA-N 0.000 description 1
SZTSCKRNSNNEQJ-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-(6-fluoro-4-hydroxy-1h-benzimidazol-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2NC3=CC(F)=CC(O)=C3N=2)N2C)C2=C1 SZTSCKRNSNNEQJ-UHFFFAOYSA-N 0.000 description 1
DMAHWETWCUYJKG-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-(6-fluoro-5-hydroxy-1h-benzimidazol-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2NC3=CC(F)=C(O)C=C3N=2)N2C)C2=C1 DMAHWETWCUYJKG-UHFFFAOYSA-N 0.000 description 1
KYMUHTAIMUPAHM-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-[1-(2,2-dimethylpropanoyloxymethyl)-5-hydroxybenzimidazol-2-yl]ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2N(C3=CC=C(O)C=C3N=2)COC(=O)C(C)(C)C)N2C)C2=C1 KYMUHTAIMUPAHM-UHFFFAOYSA-N 0.000 description 1
QPTZSPXILNFVOX-UHFFFAOYSA-N ethyl 2-[2-[[2-[1-[1-(2-methoxyethyl)benzimidazol-2-yl]ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2N(C3=CC=CC=C3N=2)CCOC)N2C)C2=C1 QPTZSPXILNFVOX-UHFFFAOYSA-N 0.000 description 1
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NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
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QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
OQIABXWGOWFBKD-UHFFFAOYSA-N methyl 2-(2-aminoethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCN OQIABXWGOWFBKD-UHFFFAOYSA-N 0.000 description 1
FXNQOSYTBDAKCJ-UHFFFAOYSA-N methyl 2-[1-[6-[2-(2-ethoxycarbonylphenoxy)ethylcarbamoyl]-1-methylbenzimidazol-2-yl]ethyl]-5-hydroxybenzimidazole-1-carboxylate Chemical compound CCOC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2N(C3=CC=C(O)C=C3N=2)C(=O)OC)N2C)C2=C1 FXNQOSYTBDAKCJ-UHFFFAOYSA-N 0.000 description 1
UQTOPLGGIQTEKT-UHFFFAOYSA-N methyl 2-[2-[[2-[1-(6-fluoro-1h-benzimidazol-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(C)C=2NC3=CC=C(F)C=C3N=2)N2C)C2=C1 UQTOPLGGIQTEKT-UHFFFAOYSA-N 0.000 description 1
VRGKBILPPJTDFA-UHFFFAOYSA-N methyl 2-[2-[[2-[6-(diaminomethylideneamino)-1h-benzimidazole-2-carbonyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(C(=O)C=2NC3=CC=C(NC(N)=N)C=C3N=2)N2C)C2=C1 VRGKBILPPJTDFA-UHFFFAOYSA-N 0.000 description 1
WVKWFMJGYJWNCD-UHFFFAOYSA-N methyl 2-[2-[[2-[[6-(diaminomethylideneamino)-1h-benzimidazol-2-yl]methyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCNC(=O)C1=CC=C(N=C(CC=2NC3=CC=C(NC(N)=N)C=C3N=2)N2C)C2=C1 WVKWFMJGYJWNCD-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/06—Antiasthmatics
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- 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
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
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- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- 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
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- C07D401/14—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 three or more hetero rings
- 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
- C07D403/14—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 three or more hetero rings
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO19994858A 1997-04-07 1999-10-06 Benzimidazol-derivater, anvendelse derav og farmasöytiske preparater inneholdende dem NO314183B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US83367497A	1997-04-07	1997-04-07
PCT/US1997/021849 WO1998045275A1 (en)	1997-04-07	1997-12-01	Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity

Publications (3)

Publication Number	Publication Date
NO994858D0 NO994858D0 (no)	1999-10-06
NO994858L NO994858L (no)	1999-12-06
NO314183B1 true NO314183B1 (no)	2003-02-10

Family

ID=25264996

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19994858A NO314183B1 (no)	1997-04-07	1999-10-06	Benzimidazol-derivater, anvendelse derav og farmasöytiske preparater inneholdende dem

Country Status (16)

Country	Link
EP (1)	EP1019382A1 (lt)
JP (1)	JP2001519806A (lt)
KR (1)	KR20010006119A (lt)
CN (1)	CN1251579A (lt)
AU (1)	AU752064B2 (lt)
CA (1)	CA2285454A1 (lt)
EE (1)	EE04055B1 (lt)
HU (1)	HUP0001522A3 (lt)
LT (1)	LT4704B (lt)
LV (1)	LV12495B (lt)
NO (1)	NO314183B1 (lt)
NZ (1)	NZ500029A (lt)
PL (1)	PL336233A1 (lt)
SI (1)	SI20115A (lt)
SK (1)	SK136799A3 (lt)
WO (1)	WO1998045275A1 (lt)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6221914B1 (en)	1997-11-10	2001-04-24	Array Biopharma Inc.	Sulfonamide bridging compounds that inhibit tryptase activity
WO1999026932A1 (en) *	1997-11-26	1999-06-03	Axys Pharmaceuticals, Inc.	By amidino group substituted heterocyclic derivatives and their use as anticoagulants
AU1608399A (en) *	1997-11-26	1999-06-15	Axys Pharmaceuticals, Inc.	Substituted amidinoaryl derivatives and their use as anticoagulants
GT199900167A (es) *	1998-10-01	2001-03-21		Nuevos bis-benzimidazoles.
WO2000020400A1 (en) *	1998-10-05	2000-04-13	Axys Pharmaceuticals, Inc.	Novel compounds and compositions for treating hepatitis c infections
AU5314900A (en) *	1999-06-04	2000-12-28	Elan Pharma International Limited	Compositions and methods for inhibiting cell death
DE19953899A1 (de) *	1999-11-10	2001-05-17	Boehringer Ingelheim Pharma	Carboxamid-substituierte Benzimidazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
WO2001052883A1 (en) *	2000-01-20	2001-07-26	Amgen Inc.	Inhibitors of protease-activated receptor-2 (par-2) as novel asthma therapeutics
US6448281B1 (en) *	2000-07-06	2002-09-10	Boehringer Ingelheim (Canada) Ltd.	Viral polymerase inhibitors
DE10048715A1 (de) *	2000-09-30	2004-05-19	Grünenthal GmbH	Verwendung von Aminosäure zur Behandlung von Schmerz
JP4176477B2 (ja) *	2001-03-01	2008-11-05	塩野義製薬株式会社	Ｈｉｖインテグラーゼ阻害活性を有する含窒素芳香族複素環誘導体
GB0406282D0 (en) *	2004-03-19	2004-04-21	Arrow Therapeutics Ltd	Therapeutic compounds
KR101837759B1 (ko)	2010-02-18	2018-04-26	브이티브이 테라퓨틱스 엘엘씨	치환된 융합 이미다졸 유도체, 약학적 조성물, 및 그것의 사용 방법
US8759535B2 (en)	2010-02-18	2014-06-24	High Point Pharmaceuticals, Llc	Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof
DE102011111991A1 (de)	2011-08-30	2013-02-28	Lead Discovery Center Gmbh	Neue Cyclosporin-Derivate
CN104080772B (zh) *	2011-11-29	2016-10-05	佩罗斯菲尔股份有限公司	抗凝血逆转剂
WO2016089648A1 (en)	2014-12-01	2016-06-09	Vtv Therapeutics Llc	Bach 1 inhibitors in combination with nrf2 activators and pharmaceutical compositions thereof
WO2020233645A1 (zh) *	2019-05-21	2020-11-26	浙江海正药业股份有限公司	大环类衍生物、及其制备方法和用途

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3105837A (en) *	1961-10-20	1963-10-01	Upjohn Co	2, 2'-alkylenebisbenzimidazoles
US3210370A (en) *	1964-06-22	1965-10-05	Upjohn Co	Process for preparing 2, 2'-methylene-bisareneimiazoles
AU7661594A (en) *	1993-09-22	1995-04-10	Glaxo Wellcome House	Bis(amidinobenzimidazolyl)alkanes as antiviral agents
US6815461B1 (en) *	1994-01-20	2004-11-09	The University Of North Carolina At Chapel Hill	Method of inhibiting retroviral integrase
US5693515A (en) *	1995-04-28	1997-12-02	Arris Pharmaceutical Corporation	Metal complexed serine protease inhibitors

1997
- 1997-12-01 HU HU0001522A patent/HUP0001522A3/hu unknown
- 1997-12-01 EP EP97954520A patent/EP1019382A1/en not_active Withdrawn
- 1997-12-01 CN CN97182098A patent/CN1251579A/zh active Pending
- 1997-12-01 JP JP54273998A patent/JP2001519806A/ja active Pending
- 1997-12-01 WO PCT/US1997/021849 patent/WO1998045275A1/en not_active Ceased
- 1997-12-01 EE EEP199900477A patent/EE04055B1/xx not_active IP Right Cessation
- 1997-12-01 PL PL97336233A patent/PL336233A1/xx unknown
- 1997-12-01 SI SI9720094A patent/SI20115A/sl unknown
- 1997-12-01 CA CA002285454A patent/CA2285454A1/en not_active Abandoned
- 1997-12-01 KR KR1019997009197A patent/KR20010006119A/ko not_active Ceased
- 1997-12-01 AU AU58950/98A patent/AU752064B2/en not_active Ceased
- 1997-12-01 NZ NZ500029A patent/NZ500029A/en unknown
- 1997-12-01 SK SK1367-99A patent/SK136799A3/sk unknown
1999
- 1999-10-06 NO NO19994858A patent/NO314183B1/no unknown
- 1999-11-02 LV LVP-99-153A patent/LV12495B/en unknown
- 1999-11-05 LT LT99-131A patent/LT4704B/lt not_active IP Right Cessation

Also Published As

Publication number	Publication date
JP2001519806A (ja)	2001-10-23
KR20010006119A (ko)	2001-01-26
HUP0001522A3 (en)	2001-08-28
NZ500029A (en)	2001-02-23
NO994858L (no)	1999-12-06
NO994858D0 (no)	1999-10-06
CN1251579A (zh)	2000-04-26
CA2285454A1 (en)	1998-10-15
WO1998045275A1 (en)	1998-10-15
HUP0001522A2 (hu)	2001-05-28
EE9900477A (et)	2000-06-15
EE04055B1 (et)	2003-06-16
EP1019382A1 (en)	2000-07-19
LV12495B (en)	2001-01-20
LT4704B (lt)	2000-09-25
LT99131A (lt)	2000-04-25
AU752064B2 (en)	2002-09-05
AU5895098A (en)	1998-10-30
SK136799A3 (en)	2000-07-11
PL336233A1 (en)	2000-06-19
LV12495A (en)	2000-06-20
SI20115A (sl)	2000-06-30

Publication	Publication Date	Title
EP1028111B1 (en)	2004-05-12	Amide derivatives or salts thereof
NO314183B1 (no)	2003-02-10	Benzimidazol-derivater, anvendelse derav og farmasöytiske preparater inneholdende dem
US5314880A (en)	1994-05-24	Benzimidazole derivatives
DE69617788T2 (de)	2002-06-20	Aromatische Hydroxamsäure-Verbindungen, ihre Herstellung und Verwendung
DE69333138T2 (de)	2004-06-09	Angiotensin-II-Antagonisten
EP1142879B1 (en)	2007-10-10	Imidazole compounds and medicinal use thereof
US20030130278A1 (en)	2003-07-10	Alkynylated fused ring pyrimidine compounds
KR20050122210A (ko)	2005-12-28	히스톤 탈아세틸화 효소 억제제
HU223140B1 (hu)	2004-03-29	Bradikinin antagonista hatású kinolinszármazékok és hetero-anológjaik, eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények
HU211275A9 (en)	1995-11-28	New heterocyclic compounds
US5750699A (en)	1998-05-12	Method of preparing certain 3-halo-imidazopyridines
JP4092732B2 (ja)	2008-05-28	ブラジキニン作動薬としてのキノリンおよびベンズイミダゾール誘導体
US5741794A (en)	1998-04-21	Heterocyclic sulfonamide derivatives as antagonists of PAF and angiotensin II
US5276153A (en)	1994-01-04	Production of certain imidazopyridinyl-methyl-benzene sulfonamides
WO2003033478A1 (en)	2003-04-24	Alkynylated fused ring pyrimidine compounds as matrix metalloprotease-13 inhibitors
JPH11349572A (ja)	1999-12-21	新規アミド誘導体およびその塩
HUT74678A (en)	1997-01-28	Imidazo[1,2-a]pyrazine-4-one, preparation thereof and drugs containing same
US6562854B2 (en)	2003-05-13	Compositions comprising a substituted benzimidazole useful for treating immunomediated inflammatory disorders
JP2000502699A (ja)	2000-03-07	ピリド（２，３−ｂ）ピラジン誘導体
US6093714A (en)	2000-07-25	Tricyclic benzazepine compounds
JPWO1997000258A1 (ja)	1998-08-25	三環性ベンゾアゼピン化合物
US5446032A (en)	1995-08-29	Imidazo (4,5-C) pyridine derivatives as PAF antagonists
MXPA99009006A (en)	2000-08-01	Compounds and compositions for treating diseases associated with serine protease, particularly tryptase, activity
US5624948A (en)	1997-04-29	1-(2-benzimidazolyl)-1,5-diazacyclooctane compounds
US20030207876A1 (en)	2003-11-06	3-Azabicyclo[3.1.0]hexane derivatives useful in therapy