NO314504B1 - Benzimidazolforbindelser, farmasöytiske sammensetninger som inneholder forbindelsene og deres anvendelser - Google Patents

Benzimidazolforbindelser, farmasöytiske sammensetninger som inneholder forbindelsene og deres anvendelser Download PDF

Info

Publication number: NO314504B1
Authority: NO; Norway
Prior art keywords: mixture; mmol; phenyl; furanyl; benzimidazole
Prior art date: 1995-04-21

Application number

NO19974844A

Other languages

English (en)

Norwegian (no)

Other versions

NO974844D0 (no

NO974844L (no

Inventor

Lene Teuber

Frank Waetjen

Yoshimasa Fukuda

Osamu Ushiroda

Toshiro Sasaki

Original Assignee

Neurosearch As

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.)

1995-04-21

Filing date

1997-10-20

Publication date

2003-03-31

1997-10-20 Application filed by Neurosearch As filed Critical Neurosearch As

1997-10-20 Publication of NO974844D0 publication Critical patent/NO974844D0/no

1997-12-16 Publication of NO974844L publication Critical patent/NO974844L/no

2003-03-31 Publication of NO314504B1 publication Critical patent/NO314504B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 67
239000008194 pharmaceutical composition Substances 0.000 title description 8
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
239000000203 mixture Substances 0.000 claims description 174
150000003839 salts Chemical class 0.000 claims description 16
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
201000010099 disease Diseases 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
208000019901 Anxiety disease Diseases 0.000 claims description 5
206010010904 Convulsion Diseases 0.000 claims description 5
208000026139 Memory disease Diseases 0.000 claims description 5
230000036506 anxiety Effects 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
208000019116 sleep disease Diseases 0.000 claims description 5
ISFAJKOCZDEYIF-UHFFFAOYSA-N 2-[3-[5-(furan-3-yl)benzimidazol-1-yl]phenyl]-1,3-thiazole Chemical compound C1=CSC(C=2C=C(C=CC=2)N2C3=CC=C(C=C3N=C2)C2=COC=C2)=N1 ISFAJKOCZDEYIF-UHFFFAOYSA-N 0.000 claims description 4
UBYXGDFRIQIHEN-UHFFFAOYSA-N 5-(furan-3-yl)-1-(6-imidazol-1-ylpyrimidin-4-yl)benzimidazole Chemical compound C1=NC=CN1C1=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=NC=N1 UBYXGDFRIQIHEN-UHFFFAOYSA-N 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
LYRZIEWJELNQDG-UHFFFAOYSA-N 5-(furan-3-yl)-1-(3-pyrazol-1-ylphenyl)benzimidazole Chemical compound C1=CC=NN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 LYRZIEWJELNQDG-UHFFFAOYSA-N 0.000 claims description 3
230000036461 convulsion Effects 0.000 claims description 3
206010015037 epilepsy Diseases 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
FCBOUJYKAGWYQM-DEOSSOPVSA-N 6-[[(2s)-1-hydroxy-3-phenylpropan-2-yl]amino]-n-(2-phenoxyethyl)-2-(3,4,5-trimethoxyphenyl)pyridine-3-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2C(=CC=C(N[C@H](CO)CC=3C=CC=CC=3)N=2)C(=O)NCCOC=2C=CC=CC=2)=C1 FCBOUJYKAGWYQM-DEOSSOPVSA-N 0.000 claims description 2
PFGVNLZDWRZPJW-OPAMFIHVSA-N otamixaban Chemical compound C([C@@H](C(=O)OC)[C@@H](C)NC(=O)C=1C=CC(=CC=1)C=1C=C[N+]([O-])=CC=1)C1=CC=CC(C(N)=N)=C1 PFGVNLZDWRZPJW-OPAMFIHVSA-N 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
YCGQPIRMLGEWMW-UHFFFAOYSA-N 1-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,8-naphthyridin-3-yl]-3-[4-[(dimethylamino)methyl]-2,6-di(propan-2-yl)phenyl]urea;hydrochloride Chemical compound Cl.CC(C)C=1C=C(CN(C)C)C=C(C(C)C)C=1NC(=O)NC=1C(=O)N(CCCC)C2=NC=CC=C2C=1C1=CC=CC(OC)=C1 YCGQPIRMLGEWMW-UHFFFAOYSA-N 0.000 claims 1
JENUMEXEVAAAJX-SNVBAGLBSA-N 2-(3,5-dimethyl-1,2,4-triazol-1-yl)-1-[(2r)-2-methyl-4-[2-(trifluoromethyl)-4-[2-(trifluoromethyl)pyrimidin-5-yl]-1,3-thiazol-5-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1C)N(C2=C(N=C(S2)C(F)(F)F)C=2C=NC(=NC=2)C(F)(F)F)CCN1C(=O)CN1N=C(C)N=C1C JENUMEXEVAAAJX-SNVBAGLBSA-N 0.000 claims 1
GOAKYBVMJUXOFY-LBPRGKRZSA-N 3-amino-4-[(3S)-3-(2-ethoxyethoxymethyl)piperidin-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound CCOCCOC[C@@H](CCC1)CN1C1=C(C(N)=C(C(N)=O)S2)C2=NC=C1 GOAKYBVMJUXOFY-LBPRGKRZSA-N 0.000 claims 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims 1
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
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229910000027 potassium carbonate Inorganic materials 0.000 description 14
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239000000706 filtrate Substances 0.000 description 13
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238000004440 column chromatography Methods 0.000 description 12
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238000000034 method Methods 0.000 description 12
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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
239000002904 solvent Substances 0.000 description 12
229960003692 gamma aminobutyric acid Drugs 0.000 description 11
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
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239000007787 solid Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
239000000556 agonist Substances 0.000 description 9
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HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 7
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229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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XRBSVBDYAUOOPW-UHFFFAOYSA-N 4-(3-nitrophenyl)pyrimidine Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=CN=CC=2)=C1 XRBSVBDYAUOOPW-UHFFFAOYSA-N 0.000 description 5
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239000000825 pharmaceutical preparation Substances 0.000 description 1
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
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229910052700 potassium Inorganic materials 0.000 description 1
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235000011118 potassium hydroxide Nutrition 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000000216 proconvulsive effect Effects 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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239000012266 salt solution Substances 0.000 description 1
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239000000932 sedative agent Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
239000012085 test solution Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
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Classifications

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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- A—HUMAN NECESSITIES
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- 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
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
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- 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
- 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
- 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
- C07D401/02—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
- C07D401/10—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 carbon chain containing aromatic 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
- C07D403/02—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
- C07D403/10—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 aromatic rings
- 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
- C07D405/10—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 carbon chain containing aromatic rings
- 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
- C07D405/14—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 three or more hetero rings
- 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
- C07D409/10—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 aromatic 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
- C07D413/14—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
- 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
- C07D417/10—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 carbon chain containing aromatic rings
- 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
- C07D417/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings

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Chemical Kinetics & Catalysis (AREA)
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Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Anesthesiology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
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NO19974844A 1995-04-21 1997-10-20 Benzimidazolforbindelser, farmasöytiske sammensetninger som inneholder forbindelsene og deres anvendelser NO314504B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DK46095		1995-04-21
PCT/EP1996/001606 WO1996033194A1 (en)	1995-04-21	1996-04-17	Benzimidazole compounds and their use as modulators of the gaba a receptor complex

Publications (3)

Publication Number	Publication Date
NO974844D0 NO974844D0 (no)	1997-10-20
NO974844L NO974844L (no)	1997-12-16
NO314504B1 true NO314504B1 (no)	2003-03-31

Family

ID=8093808

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NO19974844A NO314504B1 (no)	1995-04-21	1997-10-20	Benzimidazolforbindelser, farmasöytiske sammensetninger som inneholder forbindelsene og deres anvendelser

Country Status (22)

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US (2)	US5922724A (is)
EP (3)	EP0821684B1 (is)
JP (2)	JP3342874B2 (is)
KR (2)	KR100297445B1 (is)
CN (2)	CN1072669C (is)
AT (2)	ATE210132T1 (is)
AU (2)	AU695957B2 (is)
BR (1)	BR9608048A (is)
CA (2)	CA2218493C (is)
CZ (1)	CZ287545B6 (is)
DE (2)	DE69617665T2 (is)
EE (1)	EE04310B1 (is)
HU (1)	HUP9801692A3 (is)
IS (1)	IS1959B (is)
NO (1)	NO314504B1 (is)
NZ (1)	NZ307521A (is)
PL (1)	PL183853B1 (is)
RU (1)	RU2135493C1 (is)
SK (1)	SK282425B6 (is)
TR (1)	TR199701218T2 (is)
UA (1)	UA54393C2 (is)
WO (2)	WO1996033194A1 (is)

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1996
- 1996-04-17 RU RU97119173A patent/RU2135493C1/ru not_active IP Right Cessation
- 1996-04-17 UA UA97115591A patent/UA54393C2/uk unknown
- 1996-04-17 AT AT96914932T patent/ATE210132T1/de not_active IP Right Cessation
- 1996-04-17 EP EP96914932A patent/EP0821684B1/en not_active Expired - Lifetime
- 1996-04-17 CZ CZ19973292A patent/CZ287545B6/cs not_active IP Right Cessation
- 1996-04-17 HU HU9801692A patent/HUP9801692A3/hu unknown
- 1996-04-17 PL PL96322892A patent/PL183853B1/pl not_active IP Right Cessation
- 1996-04-17 EP EP01112476A patent/EP1164134A1/en not_active Withdrawn
- 1996-04-17 JP JP53146496A patent/JP3342874B2/ja not_active Expired - Fee Related
- 1996-04-17 EE EE9700283A patent/EE04310B1/xx not_active IP Right Cessation
- 1996-04-17 CN CN96193419A patent/CN1072669C/zh not_active Expired - Fee Related
- 1996-04-17 BR BR9608048-5A patent/BR9608048A/pt not_active IP Right Cessation
- 1996-04-17 TR TR97/01218T patent/TR199701218T2/xx unknown
- 1996-04-17 US US08/945,023 patent/US5922724A/en not_active Expired - Lifetime
- 1996-04-17 NZ NZ307521A patent/NZ307521A/en unknown
- 1996-04-17 SK SK1399-97A patent/SK282425B6/sk unknown
- 1996-04-17 WO PCT/EP1996/001606 patent/WO1996033194A1/en not_active Ceased
- 1996-04-17 CA CA002218493A patent/CA2218493C/en not_active Expired - Fee Related
- 1996-04-17 DE DE69617665T patent/DE69617665T2/de not_active Expired - Lifetime
- 1996-04-17 AU AU56891/96A patent/AU695957B2/en not_active Ceased
- 1996-04-17 KR KR1019970707465A patent/KR100297445B1/ko not_active Expired - Fee Related
- 1996-04-19 DE DE69636670T patent/DE69636670T2/de not_active Expired - Lifetime
- 1996-04-19 WO PCT/EP1996/001654 patent/WO1996033192A1/en not_active Ceased
- 1996-04-19 US US08/930,216 patent/US5902813A/en not_active Expired - Lifetime
- 1996-04-19 CA CA002217601A patent/CA2217601C/en not_active Expired - Fee Related
- 1996-04-19 EP EP96912025A patent/EP0821683B1/en not_active Expired - Lifetime
- 1996-04-19 JP JP8531487A patent/JP3040485B2/ja not_active Expired - Fee Related
- 1996-04-19 CN CN96193420A patent/CN1182426A/zh active Pending
- 1996-04-19 KR KR1019970707464A patent/KR19990007941A/ko not_active Abandoned
- 1996-04-19 AU AU55014/96A patent/AU5501496A/en not_active Abandoned
- 1996-04-19 AT AT96912025T patent/ATE344257T1/de not_active IP Right Cessation
1997
- 1997-10-13 IS IS4588A patent/IS1959B/is unknown
- 1997-10-20 NO NO19974844A patent/NO314504B1/no unknown

Also Published As

Publication number	Publication date
HUP9801692A2 (hu)	1999-03-29
WO1996033192A1 (en)	1996-10-24
AU695957B2 (en)	1998-08-27
KR19990007942A (ko)	1999-01-25
CA2218493A1 (en)	1996-10-24
EP0821684A1 (en)	1998-02-04
CA2217601C (en)	2002-04-16
DE69617665D1 (de)	2002-01-17
PL183853B1 (pl)	2002-07-31
ATE344257T1 (de)	2006-11-15
DE69617665T2 (de)	2002-05-08
EE9700283A (et)	1998-06-15
TR199701218T2 (xx)	1998-08-21
WO1996033194A1 (en)	1996-10-24
RU2135493C1 (ru)	1999-08-27
CN1182426A (zh)	1998-05-20
NZ307521A (en)	1999-04-29
BR9608048A (pt)	1999-11-30
SK139997A3 (en)	1998-05-06
SK282425B6 (sk)	2002-01-07
IS1959B (is)	2004-11-15
CN1182427A (zh)	1998-05-20
HUP9801692A3 (en)	2001-11-28
CN1072669C (zh)	2001-10-10
AU5501496A (en)	1996-11-07
JPH11501320A (ja)	1999-02-02
CA2217601A1 (en)	1996-10-24
IS4588A (is)	1997-10-13
CA2218493C (en)	2005-02-22
EP0821683B1 (en)	2006-11-02
EP0821684B1 (en)	2001-12-05
AU5689196A (en)	1996-11-07
EP0821683A1 (en)	1998-02-04
KR100297445B1 (ko)	2001-10-25
NO974844D0 (no)	1997-10-20
ATE210132T1 (de)	2001-12-15
DE69636670T2 (de)	2007-02-08
CZ287545B6 (en)	2000-12-13
UA54393C2 (uk)	2003-03-17
CZ329297A3 (cs)	1998-03-18
JPH11501321A (ja)	1999-02-02
JP3342874B2 (ja)	2002-11-11
KR19990007941A (ko)	1999-01-25
US5922724A (en)	1999-07-13
DE69636670D1 (de)	2006-12-14
US5902813A (en)	1999-05-11
JP3040485B2 (ja)	2000-05-15
EE04310B1 (et)	2004-06-15
EP1164134A1 (en)	2001-12-19
NO974844L (no)	1997-12-16
PL322892A1 (en)	1998-03-02
HK1015674A1 (en)	1999-10-22

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JP2006522070A (ja)	2006-09-28	ベンズイミダゾール誘導体及びこれをｇａｂａａ受容体複合体をモジュレートするために使用する方法
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