KR20080077620A - 벤즈이미다졸 및 ｇａｂａａ 수용체 복합체를 조절하기위한 이의 용도 - Google Patents
벤즈이미다졸 및 ｇａｂａａ 수용체 복합체를 조절하기위한 이의 용도 Download PDFInfo
- Publication number
- KR20080077620A KR20080077620A KR1020087013766A KR20087013766A KR20080077620A KR 20080077620 A KR20080077620 A KR 20080077620A KR 1020087013766 A KR1020087013766 A KR 1020087013766A KR 20087013766 A KR20087013766 A KR 20087013766A KR 20080077620 A KR20080077620 A KR 20080077620A
- Authority
- KR
- South Korea
- Prior art keywords
- benzoimidazol
- biphenyl
- ethylamine
- ethyl
- methoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 17
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 11
- 230000033228 biological regulation Effects 0.000 claims abstract description 7
- -1 methylenedioxy, ethylenedioxy Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 150000001204 N-oxides Chemical class 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- 206010047700 Vomiting Diseases 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 230000008673 vomiting Effects 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 208000008811 Agoraphobia Diseases 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 208000019906 panic disease Diseases 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- CJKRCJXOIXCMQV-UHFFFAOYSA-N 1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 CJKRCJXOIXCMQV-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- WXYBWPPRLHMCCR-GOSISDBHSA-N (1r)-1-[1-[3-(2-piperazin-1-ylphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1N1CCNCC1 WXYBWPPRLHMCCR-GOSISDBHSA-N 0.000 claims description 4
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- OJWJWXOLHNSREK-GFCCVEGCSA-N (1r)-1-[1-[3-(3-chloro-2,6-difluorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(F)C=CC(Cl)=C1F OJWJWXOLHNSREK-GFCCVEGCSA-N 0.000 claims description 4
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- DOHDMDZZTAULIV-CQSZACIVSA-N (1r)-1-[1-[3-(5-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 DOHDMDZZTAULIV-CQSZACIVSA-N 0.000 claims description 4
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- VOXSQTUIFNZBGV-LJQANCHMSA-N (1r)-1-[1-[3-[2-(morpholin-4-ylmethyl)phenyl]phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1CN1CCOCC1 VOXSQTUIFNZBGV-LJQANCHMSA-N 0.000 claims description 4
- AUGQXCMJYAPTJI-CQSZACIVSA-N (1r)-1-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1OC(F)(F)F AUGQXCMJYAPTJI-CQSZACIVSA-N 0.000 claims description 4
- TUYYWNHWWSDRIQ-ZDUSSCGKSA-N (1s)-1-[1-[3-(2,3-difluoro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=C(F)C(F)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 TUYYWNHWWSDRIQ-ZDUSSCGKSA-N 0.000 claims description 4
- AUGQXCMJYAPTJI-AWEZNQCLSA-N (1s)-1-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1OC(F)(F)F AUGQXCMJYAPTJI-AWEZNQCLSA-N 0.000 claims description 4
- RFGVTOIEYHCKAL-OAHLLOKOSA-N 1-[2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]phenyl]ethanone Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C(C)=O RFGVTOIEYHCKAL-OAHLLOKOSA-N 0.000 claims description 4
- BNSRXWGMIKNAGW-UHFFFAOYSA-N 2-[3-[5-(1-aminoethyl)benzimidazol-1-yl]phenyl]benzonitrile Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C#N BNSRXWGMIKNAGW-UHFFFAOYSA-N 0.000 claims description 4
- QRXIIUKOQPUXMZ-CYBMUJFWSA-N 2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]-6-chlorophenol Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC(Cl)=C1O QRXIIUKOQPUXMZ-CYBMUJFWSA-N 0.000 claims description 4
- MBOOMVFLCVGQQA-CQSZACIVSA-N 2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]benzamide Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C(N)=O MBOOMVFLCVGQQA-CQSZACIVSA-N 0.000 claims description 4
- BNSRXWGMIKNAGW-OAHLLOKOSA-N 2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]benzonitrile Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C#N BNSRXWGMIKNAGW-OAHLLOKOSA-N 0.000 claims description 4
- MBOOMVFLCVGQQA-AWEZNQCLSA-N 2-[3-[5-[(1s)-1-aminoethyl]benzimidazol-1-yl]phenyl]benzamide Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C(N)=O MBOOMVFLCVGQQA-AWEZNQCLSA-N 0.000 claims description 4
- OHHDGSBAERYHES-CQSZACIVSA-N 3-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]-4-chlorobenzonitrile Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC(C#N)=CC=C1Cl OHHDGSBAERYHES-CQSZACIVSA-N 0.000 claims description 4
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
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Classifications
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- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Landscapes
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- Engineering & Computer Science (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200501719 | 2005-12-05 | ||
| DKPA200501719 | 2005-12-05 | ||
| US74253505P | 2005-12-06 | 2005-12-06 | |
| US60/742,535 | 2005-12-06 | ||
| DKPA200601326 | 2006-10-12 | ||
| DKPA200601326 | 2006-10-12 | ||
| US85129106P | 2006-10-13 | 2006-10-13 | |
| US60/851,291 | 2006-10-13 |
Publications (1)
| Publication Number | Publication Date |
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| KR20080077620A true KR20080077620A (ko) | 2008-08-25 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1020087013766A Withdrawn KR20080077620A (ko) | 2005-12-05 | 2006-12-04 | 벤즈이미다졸 및 ｇａｂａａ 수용체 복합체를 조절하기위한 이의 용도 |
Country Status (14)
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| US (1) | US7923464B2 (https=) |
| EP (1) | EP1996556B1 (https=) |
| JP (1) | JP2009518292A (https=) |
| KR (1) | KR20080077620A (https=) |
| AT (1) | ATE449077T1 (https=) |
| AU (1) | AU2006324046A1 (https=) |
| CA (1) | CA2632395A1 (https=) |
| DE (1) | DE602006010602D1 (https=) |
| DK (1) | DK1996556T3 (https=) |
| ES (1) | ES2335438T3 (https=) |
| IL (1) | IL189974A0 (https=) |
| NO (1) | NO20083045L (https=) |
| PL (1) | PL1996556T3 (https=) |
| WO (1) | WO2007065864A1 (https=) |
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| TWI391381B (zh) | 2006-03-24 | 2013-04-01 | Neurosearch As | 新穎的苯并咪唑衍生物、含有其之醫藥組成物、及其於製造藥物之用途 |
| JP2011507905A (ja) * | 2007-12-21 | 2011-03-10 | ワイス・エルエルシー | ベンズイミダゾール化合物 |
| WO2009127822A2 (en) * | 2008-04-16 | 2009-10-22 | Biolipox Ab | Bis-aryl compounds for use as medicaments |
| WO2010039668A2 (en) * | 2008-10-01 | 2010-04-08 | The Regents Of The University Of California | Inhibitors of cyclin kinase inhibitor p21 |
| WO2010055125A1 (en) * | 2008-11-14 | 2010-05-20 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| WO2010055127A1 (en) * | 2008-11-14 | 2010-05-20 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| CA2882708A1 (en) * | 2012-08-21 | 2014-02-27 | Sage Therapeutics, Inc. | Methods of treating epilepsy or status epilepticus |
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| DK40192D0 (da) * | 1992-03-26 | 1992-03-26 | Neurosearch As | Imidazolforbindelser, deres fremstilling og anvendelse |
| PL183853B1 (pl) | 1995-04-21 | 2002-07-31 | Neurosearch As | Nowa pochodna benzimidazolu i środek farmaceutyczny |
| WO1998017651A1 (en) * | 1996-10-21 | 1998-04-30 | Neurosearch A/S | 1-phenyl-benzimidazole compounds and their use as baga-a receptor modulators |
| NZ503435A (en) | 1997-10-10 | 2001-12-21 | Neurosearch As | Oxime substituted 1-(3-(heteroaryl)phenyl)-benzimidazole compounds having GABA activity |
| IL146403A0 (en) * | 1999-06-22 | 2002-07-25 | Neurosearch As | Novel benzimidazole derivatives and pharmaceutical compositions comprising these compounds |
| WO2002050057A1 (en) | 2000-12-20 | 2002-06-27 | Neurosearch A/S | Novel benzimidazole derivatives for the treatment of gaba-alpha mediated disorders |
| EP1613618A2 (en) | 2003-04-03 | 2006-01-11 | Neurosearch A/S | BENZIMIDAZOLE DERIVATIVES AND THEIR USE FOR MODULATING THE GABA- sb A /sb RECEPTOR COMPLEX |
| DE602004011914T2 (de) | 2003-04-03 | 2008-06-12 | Neurosearch A/S | Benzimidazole derivate und ihre anwendung als gaba a rezeptor komplex modulatoren |
| JP4769720B2 (ja) * | 2003-08-21 | 2011-09-07 | オーエスアイ・ファーマシューテイカルズ・エル・エル・シー | Ｎ−置換ベンズイミダゾリルｃ−Ｋｉｔ阻害剤 |
| JP2007509108A (ja) * | 2003-10-23 | 2007-04-12 | アクゾ ノベル ナムローゼ フェンノートシャップ | １，５，７−三置換ベンズイミダゾール誘導体及びｇａｂａａ受容体複合体を調節するためのその使用 |
| CA2589770A1 (en) * | 2004-12-01 | 2006-06-08 | Osi Pharmaceuticals, Inc. | N-substituted benzimidazolyl c-kit inhibitors and combinatorial benzimidazole library |
| AU2006233894A1 (en) | 2005-04-13 | 2006-10-19 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the GABAA receptor complex |
| EP1874758A1 (en) * | 2005-04-19 | 2008-01-09 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| TWI391381B (zh) | 2006-03-24 | 2013-04-01 | Neurosearch As | 新穎的苯并咪唑衍生物、含有其之醫藥組成物、及其於製造藥物之用途 |
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2006
- 2006-12-04 CA CA002632395A patent/CA2632395A1/en not_active Abandoned
- 2006-12-04 KR KR1020087013766A patent/KR20080077620A/ko not_active Withdrawn
- 2006-12-04 WO PCT/EP2006/069237 patent/WO2007065864A1/en not_active Ceased
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- 2006-12-04 AU AU2006324046A patent/AU2006324046A1/en not_active Abandoned
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- 2006-12-04 AT AT06830303T patent/ATE449077T1/de active
- 2006-12-04 US US12/085,769 patent/US7923464B2/en not_active Expired - Fee Related
- 2006-12-04 PL PL06830303T patent/PL1996556T3/pl unknown
- 2006-12-04 JP JP2008542778A patent/JP2009518292A/ja not_active Abandoned
- 2006-12-04 DK DK06830303.1T patent/DK1996556T3/da active
- 2006-12-04 EP EP06830303A patent/EP1996556B1/en not_active Not-in-force
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2008
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- 2008-07-04 NO NO20083045A patent/NO20083045L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE602006010602D1 (de) | 2009-12-31 |
| ES2335438T3 (es) | 2010-03-26 |
| US7923464B2 (en) | 2011-04-12 |
| EP1996556A1 (en) | 2008-12-03 |
| JP2009518292A (ja) | 2009-05-07 |
| NO20083045L (no) | 2008-09-04 |
| ATE449077T1 (de) | 2009-12-15 |
| CA2632395A1 (en) | 2007-06-14 |
| WO2007065864A1 (en) | 2007-06-14 |
| AU2006324046A1 (en) | 2007-06-14 |
| PL1996556T3 (pl) | 2010-05-31 |
| IL189974A0 (en) | 2008-08-07 |
| DK1996556T3 (da) | 2010-04-06 |
| EP1996556B1 (en) | 2009-11-18 |
| US20090048321A1 (en) | 2009-02-19 |
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| PA0105 | International application |
Patent event date: 20080605 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |