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- Withdrawn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
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 206010010904 Convulsion Diseases 0.000 claims description 5
- 208000007101 Muscle Cramp Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- ZKJDXSBGJFPJLC-CQSZACIVSA-N (1r)-1-[1-[3-(1,3-benzodioxol-4-yl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC2=C1OCO2 ZKJDXSBGJFPJLC-CQSZACIVSA-N 0.000 claims description 4
- TUYYWNHWWSDRIQ-CYBMUJFWSA-N (1r)-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-CYBMUJFWSA-N 0.000 claims description 4
- MZWSTKBMZXQVOO-CYBMUJFWSA-N (1r)-1-[1-[3-(2,6-dichlorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(Cl)C=CC=C1Cl MZWSTKBMZXQVOO-CYBMUJFWSA-N 0.000 claims description 4
- NPPYMOZIWZOUSL-CQSZACIVSA-N (1r)-1-[1-[3-(2-chloro-6-fluoro-3-methylphenyl)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(C)=C1Cl NPPYMOZIWZOUSL-CQSZACIVSA-N 0.000 claims description 4
- KWLIBQUJFONRSM-CQSZACIVSA-N (1r)-1-[1-[3-(2-chloro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(Cl)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 KWLIBQUJFONRSM-CQSZACIVSA-N 0.000 claims description 4
- 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
- DWWPQNSBCRBVNY-CYBMUJFWSA-N (1r)-1-[1-[3-(3,5-difluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(F)C=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 DWWPQNSBCRBVNY-CYBMUJFWSA-N 0.000 claims description 4
- 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
- ROUPFXQEQBKISE-CQSZACIVSA-N (1r)-1-[1-[3-(4-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC(F)=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 ROUPFXQEQBKISE-CQSZACIVSA-N 0.000 claims description 4
- 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
- VIROKERMYCAYND-CQSZACIVSA-N (1r)-1-[1-[3-(6-chloro-2-fluoro-3-methylphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(Cl)C=CC(C)=C1F VIROKERMYCAYND-CQSZACIVSA-N 0.000 claims description 4
- 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
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
- 208000005392 Spasm Diseases 0.000 claims description 4
- 206010008118 cerebral infarction Diseases 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UYLLMTPLYNFJAL-MRXNPFEDSA-N n-[(1r)-1-[1-[3-(2-acetylphenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C(C)=O UYLLMTPLYNFJAL-MRXNPFEDSA-N 0.000 claims description 4
- IWWSRBSXDQQAGW-MRXNPFEDSA-N n-[(1r)-1-[1-[3-(2-cyanophenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C#N IWWSRBSXDQQAGW-MRXNPFEDSA-N 0.000 claims description 4
- SUONAIKREXBHLR-MRXNPFEDSA-N n-[(1r)-1-[1-[3-(2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)NC(C)=O)=C1 SUONAIKREXBHLR-MRXNPFEDSA-N 0.000 claims description 4
- ZFDLVBOYJCBUAR-OAHLLOKOSA-N n-[(1r)-1-[1-[3-(5-chloro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound COC1=CC=C(Cl)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)NC(C)=O)=C1 ZFDLVBOYJCBUAR-OAHLLOKOSA-N 0.000 claims description 4
- DTELSNVHSFXARH-MRXNPFEDSA-N n-[(1r)-1-[1-[3-[2-(methanesulfonamido)phenyl]phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1NS(C)(=O)=O DTELSNVHSFXARH-MRXNPFEDSA-N 0.000 claims description 4
- AGKXNDOYPQMADM-UHFFFAOYSA-N n-[1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC(C(NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 AGKXNDOYPQMADM-UHFFFAOYSA-N 0.000 claims description 4
- YPKZSIPFSIDDLS-UHFFFAOYSA-N n-[1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethyl]formamide Chemical compound C1=NC2=CC(C(NC=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 YPKZSIPFSIDDLS-UHFFFAOYSA-N 0.000 claims description 4
- GSEOCHLBUIMIMP-UHFFFAOYSA-N n-[1-[1-[3-(5-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)NC(C)=O)=C1 GSEOCHLBUIMIMP-UHFFFAOYSA-N 0.000 claims description 4
- ODJHZYVXKFMQDT-UHFFFAOYSA-N n-[1-[1-[3-(5-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethyl]formamide Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)NC=O)=C1 ODJHZYVXKFMQDT-UHFFFAOYSA-N 0.000 claims description 4
- HPYLJPGWLWPGOI-OAHLLOKOSA-N n-[2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]phenyl]methanesulfonamide Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1NS(C)(=O)=O HPYLJPGWLWPGOI-OAHLLOKOSA-N 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- CJKRCJXOIXCMQV-OAHLLOKOSA-N (1r)-1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 CJKRCJXOIXCMQV-OAHLLOKOSA-N 0.000 claims description 3
- WPOMEYIQKVWZFV-OAHLLOKOSA-N (1r)-1-[1-[3-(2,4-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC(OC)=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 WPOMEYIQKVWZFV-OAHLLOKOSA-N 0.000 claims description 3
- DZOIOTNHUXUDGQ-OAHLLOKOSA-N (1r)-1-[1-[3-(2,6-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 DZOIOTNHUXUDGQ-OAHLLOKOSA-N 0.000 claims description 3
- FGERINFNQINSMH-CQSZACIVSA-N (1r)-1-[1-[3-(2-fluoro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(F)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 FGERINFNQINSMH-CQSZACIVSA-N 0.000 claims description 3
- VPHQMUURAIOPTJ-OAHLLOKOSA-N (1r)-1-[1-[3-(2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 VPHQMUURAIOPTJ-OAHLLOKOSA-N 0.000 claims description 3
- QDLHGPWPNGLLCA-CQSZACIVSA-N (1r)-1-[1-[3-(3-chloro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(Cl)C=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 QDLHGPWPNGLLCA-CQSZACIVSA-N 0.000 claims description 3
- OGQNTQKGAMZNDT-CQSZACIVSA-N (1r)-1-[1-[3-(5-chloro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=C(Cl)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 OGQNTQKGAMZNDT-CQSZACIVSA-N 0.000 claims description 3
- CJKRCJXOIXCMQV-HNNXBMFYSA-N (1s)-1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 CJKRCJXOIXCMQV-HNNXBMFYSA-N 0.000 claims description 3
- ZKJDXSBGJFPJLC-AWEZNQCLSA-N (1s)-1-[1-[3-(1,3-benzodioxol-4-yl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC2=C1OCO2 ZKJDXSBGJFPJLC-AWEZNQCLSA-N 0.000 claims description 3
- YOSFSEAGAQAXBO-HNNXBMFYSA-N (1s)-1-[1-[3-(2,3-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1OC YOSFSEAGAQAXBO-HNNXBMFYSA-N 0.000 claims description 3
- WPOMEYIQKVWZFV-HNNXBMFYSA-N (1s)-1-[1-[3-(2,4-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC(OC)=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 WPOMEYIQKVWZFV-HNNXBMFYSA-N 0.000 claims description 3
- MZWSTKBMZXQVOO-ZDUSSCGKSA-N (1s)-1-[1-[3-(2,6-dichlorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(Cl)C=CC=C1Cl MZWSTKBMZXQVOO-ZDUSSCGKSA-N 0.000 claims description 3
- GLCNXFUJTTUNSL-ZDUSSCGKSA-N (1s)-1-[1-[3-(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=C1F GLCNXFUJTTUNSL-ZDUSSCGKSA-N 0.000 claims description 3
- DZOIOTNHUXUDGQ-HNNXBMFYSA-N (1s)-1-[1-[3-(2,6-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 DZOIOTNHUXUDGQ-HNNXBMFYSA-N 0.000 claims description 3
- NPPYMOZIWZOUSL-AWEZNQCLSA-N (1s)-1-[1-[3-(2-chloro-6-fluoro-3-methylphenyl)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(C)=C1Cl NPPYMOZIWZOUSL-AWEZNQCLSA-N 0.000 claims description 3
- KWLIBQUJFONRSM-AWEZNQCLSA-N (1s)-1-[1-[3-(2-chloro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(Cl)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 KWLIBQUJFONRSM-AWEZNQCLSA-N 0.000 claims description 3
- FGERINFNQINSMH-AWEZNQCLSA-N (1s)-1-[1-[3-(2-fluoro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(F)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 FGERINFNQINSMH-AWEZNQCLSA-N 0.000 claims description 3
- VPHQMUURAIOPTJ-HNNXBMFYSA-N (1s)-1-[1-[3-(2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 VPHQMUURAIOPTJ-HNNXBMFYSA-N 0.000 claims description 3
- WXYBWPPRLHMCCR-SFHVURJKSA-N (1s)-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-SFHVURJKSA-N 0.000 claims description 3
- DWWPQNSBCRBVNY-ZDUSSCGKSA-N (1s)-1-[1-[3-(3,5-difluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(F)C=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 DWWPQNSBCRBVNY-ZDUSSCGKSA-N 0.000 claims description 3
- LQAWDGAFBLVCGO-AWEZNQCLSA-N (1s)-1-[1-[3-(3-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(F)C=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 LQAWDGAFBLVCGO-AWEZNQCLSA-N 0.000 claims description 3
- ROUPFXQEQBKISE-AWEZNQCLSA-N (1s)-1-[1-[3-(4-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC(F)=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 ROUPFXQEQBKISE-AWEZNQCLSA-N 0.000 claims description 3
- DOHDMDZZTAULIV-AWEZNQCLSA-N (1s)-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-AWEZNQCLSA-N 0.000 claims description 3
- VIROKERMYCAYND-AWEZNQCLSA-N (1s)-1-[1-[3-(6-chloro-2-fluoro-3-methylphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(Cl)C=CC(C)=C1F VIROKERMYCAYND-AWEZNQCLSA-N 0.000 claims description 3
- VOXSQTUIFNZBGV-IBGZPJMESA-N (1s)-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-IBGZPJMESA-N 0.000 claims description 3
- KXHCDIDNBFAURY-UHFFFAOYSA-N 1-[1-[3-(2-fluorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1F KXHCDIDNBFAURY-UHFFFAOYSA-N 0.000 claims description 3
- VPHQMUURAIOPTJ-UHFFFAOYSA-N 1-[1-[3-(2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)N)=C1 VPHQMUURAIOPTJ-UHFFFAOYSA-N 0.000 claims description 3
- XQLLHVNGGCGWOW-UHFFFAOYSA-N 1-[1-[3-(4-fluorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=C(F)C=C1 XQLLHVNGGCGWOW-UHFFFAOYSA-N 0.000 claims description 3
- DOHDMDZZTAULIV-UHFFFAOYSA-N 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(C)N)=C1 DOHDMDZZTAULIV-UHFFFAOYSA-N 0.000 claims description 3
- AUGQXCMJYAPTJI-UHFFFAOYSA-N 1-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1OC(F)(F)F AUGQXCMJYAPTJI-UHFFFAOYSA-N 0.000 claims description 3
- RFGVTOIEYHCKAL-HNNXBMFYSA-N 1-[2-[3-[5-[(1s)-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-HNNXBMFYSA-N 0.000 claims description 3
- YHDJWQUVASWUST-CQSZACIVSA-N 2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]-5-(trifluoromethyl)benzonitrile Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1C#N YHDJWQUVASWUST-CQSZACIVSA-N 0.000 claims description 3
- ZKAHUZIAOGHZPV-CQSZACIVSA-N 2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]-5-fluorobenzonitrile Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=C(F)C=C1C#N ZKAHUZIAOGHZPV-CQSZACIVSA-N 0.000 claims description 3
- VEIGGNXYRIZKRE-CQSZACIVSA-N 2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]-6-fluorobenzonitrile Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC(F)=C1C#N VEIGGNXYRIZKRE-CQSZACIVSA-N 0.000 claims description 3
- YHDJWQUVASWUST-AWEZNQCLSA-N 2-[3-[5-[(1s)-1-aminoethyl]benzimidazol-1-yl]phenyl]-5-(trifluoromethyl)benzonitrile Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1C#N YHDJWQUVASWUST-AWEZNQCLSA-N 0.000 claims description 3
- ZKAHUZIAOGHZPV-AWEZNQCLSA-N 2-[3-[5-[(1s)-1-aminoethyl]benzimidazol-1-yl]phenyl]-5-fluorobenzonitrile Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=C(F)C=C1C#N ZKAHUZIAOGHZPV-AWEZNQCLSA-N 0.000 claims description 3
- QRXIIUKOQPUXMZ-ZDUSSCGKSA-N 2-[3-[5-[(1s)-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-ZDUSSCGKSA-N 0.000 claims description 3
- VEIGGNXYRIZKRE-AWEZNQCLSA-N 2-[3-[5-[(1s)-1-aminoethyl]benzimidazol-1-yl]phenyl]-6-fluorobenzonitrile Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC(F)=C1C#N VEIGGNXYRIZKRE-AWEZNQCLSA-N 0.000 claims description 3
- BNSRXWGMIKNAGW-HNNXBMFYSA-N 2-[3-[5-[(1s)-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-HNNXBMFYSA-N 0.000 claims description 3
- OHHDGSBAERYHES-AWEZNQCLSA-N 3-[3-[5-[(1s)-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-AWEZNQCLSA-N 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 208000019022 Mood disease Diseases 0.000 claims description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
- 206010041247 Social fear Diseases 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- AGKXNDOYPQMADM-MRXNPFEDSA-N n-[(1r)-1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 AGKXNDOYPQMADM-MRXNPFEDSA-N 0.000 claims description 3
- FRMLZTKAEAXIRP-OAHLLOKOSA-N n-[(1r)-1-[1-[3-(2-cyano-4-fluorophenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=C(F)C=C1C#N FRMLZTKAEAXIRP-OAHLLOKOSA-N 0.000 claims description 3
- AWVYIUGTVFUVFQ-HNNXBMFYSA-N n-[(1s)-1-[1-[3-(1,3-benzodioxol-4-yl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC2=C1OCO2 AWVYIUGTVFUVFQ-HNNXBMFYSA-N 0.000 claims description 3
- UYLLMTPLYNFJAL-INIZCTEOSA-N n-[(1s)-1-[1-[3-(2-acetylphenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C(C)=O UYLLMTPLYNFJAL-INIZCTEOSA-N 0.000 claims description 3
- FRMLZTKAEAXIRP-HNNXBMFYSA-N n-[(1s)-1-[1-[3-(2-cyano-4-fluorophenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=C(F)C=C1C#N FRMLZTKAEAXIRP-HNNXBMFYSA-N 0.000 claims description 3
- IWWSRBSXDQQAGW-INIZCTEOSA-N n-[(1s)-1-[1-[3-(2-cyanophenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C#N IWWSRBSXDQQAGW-INIZCTEOSA-N 0.000 claims description 3
- SUONAIKREXBHLR-INIZCTEOSA-N n-[(1s)-1-[1-[3-(2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)NC(C)=O)=C1 SUONAIKREXBHLR-INIZCTEOSA-N 0.000 claims description 3
- DTELSNVHSFXARH-INIZCTEOSA-N n-[(1s)-1-[1-[3-[2-(methanesulfonamido)phenyl]phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1NS(C)(=O)=O DTELSNVHSFXARH-INIZCTEOSA-N 0.000 claims description 3
- GLCNXFUJTTUNSL-CYBMUJFWSA-N (1r)-1-[1-[3-(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=C1F GLCNXFUJTTUNSL-CYBMUJFWSA-N 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 2
- 208000028698 Cognitive impairment Diseases 0.000 claims description 2
- 208000030814 Eating disease Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
- 206010019196 Head injury Diseases 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010052904 Musculoskeletal stiffness Diseases 0.000 claims description 2
- 206010029333 Neurosis Diseases 0.000 claims description 2
- 206010033892 Paraplegia Diseases 0.000 claims description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 208000013200 Stress disease Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 208000009205 Tinnitus Diseases 0.000 claims description 2
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 2
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 2
- 230000003466 anti-cipated effect Effects 0.000 claims description 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 2
- 230000003111 delayed effect Effects 0.000 claims description 2
- 230000003001 depressive effect Effects 0.000 claims description 2
- 235000014632 disordered eating Nutrition 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 208000024714 major depressive disease Diseases 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 201000003152 motion sickness Diseases 0.000 claims description 2
- AGKXNDOYPQMADM-INIZCTEOSA-N n-[(1s)-1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 AGKXNDOYPQMADM-INIZCTEOSA-N 0.000 claims description 2
- ZFDLVBOYJCBUAR-HNNXBMFYSA-N n-[(1s)-1-[1-[3-(5-chloro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound COC1=CC=C(Cl)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)NC(C)=O)=C1 ZFDLVBOYJCBUAR-HNNXBMFYSA-N 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000021722 neuropathic pain Diseases 0.000 claims description 2
- 208000015238 neurotic disease Diseases 0.000 claims description 2
- 208000019899 phobic disease Diseases 0.000 claims description 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 2
- 230000033764 rhythmic process Effects 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 201000009032 substance abuse Diseases 0.000 claims description 2
- 231100000736 substance abuse Toxicity 0.000 claims description 2
- 201000006152 substance dependence Diseases 0.000 claims description 2
- 231100000886 tinnitus Toxicity 0.000 claims description 2
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 208000031649 Postoperative Nausea and Vomiting Diseases 0.000 claims 1
- 206010066962 Procedural nausea Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 230000004044 response Effects 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 abstract description 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 abstract description 3
- 230000036506 anxiety Effects 0.000 abstract description 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- 125000005843 halogen group Chemical group 0.000 description 24
- 125000001153 fluoro group Chemical group F* 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- 102000005962 receptors Human genes 0.000 description 14
- 108020003175 receptors Proteins 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000001309 chloro group Chemical group Cl* 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000002552 dosage form Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000872 buffer Substances 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000027455 binding Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- 230000002265 prevention Effects 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 229940049706 benzodiazepine Drugs 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000009870 specific binding Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007937 lozenge Substances 0.000 description 4
- SPRPMIPVZCVDHF-ZCFIWIBFSA-N n-[(1r)-1-(4-fluoro-3-nitrophenyl)ethyl]acetamide Chemical compound CC(=O)N[C@H](C)C1=CC=C(F)C([N+]([O-])=O)=C1 SPRPMIPVZCVDHF-ZCFIWIBFSA-N 0.000 description 4
- KFOAGMSRCKKDHT-LLVKDONJSA-N n-[(1r)-1-[1-(3-bromophenyl)benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@H](NC(C)=O)C)=CC=C2N1C1=CC=CC(Br)=C1 KFOAGMSRCKKDHT-LLVKDONJSA-N 0.000 description 4
- JJFMGYZAZNMBIH-SNVBAGLBSA-N n-[(1r)-1-[3-amino-4-(3-bromoanilino)phenyl]ethyl]acetamide Chemical compound NC1=CC([C@H](NC(C)=O)C)=CC=C1NC1=CC=CC(Br)=C1 JJFMGYZAZNMBIH-SNVBAGLBSA-N 0.000 description 4
- DSQGRBQPCFXCCY-SNVBAGLBSA-N n-[(1r)-1-[4-(3-bromoanilino)-3-nitrophenyl]ethyl]acetamide Chemical compound [O-][N+](=O)C1=CC([C@H](NC(C)=O)C)=CC=C1NC1=CC=CC(Br)=C1 DSQGRBQPCFXCCY-SNVBAGLBSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000002249 anxiolytic agent Substances 0.000 description 3
- 230000000949 anxiolytic effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 150000001557 benzodiazepines Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IDQNNPJLBVGCLN-SSDOTTSWSA-N n-[(1r)-1-(4-fluorophenyl)ethyl]acetamide Chemical compound CC(=O)N[C@H](C)C1=CC=C(F)C=C1 IDQNNPJLBVGCLN-SSDOTTSWSA-N 0.000 description 3
- 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 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- WUONKBADUPBURR-SNVBAGLBSA-N (1r)-1-[1-(3-bromophenyl)benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C1=CC=CC(Br)=C1 WUONKBADUPBURR-SNVBAGLBSA-N 0.000 description 2
- YOSFSEAGAQAXBO-OAHLLOKOSA-N (1r)-1-[1-[3-(2,3-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1OC YOSFSEAGAQAXBO-OAHLLOKOSA-N 0.000 description 2
- LQAWDGAFBLVCGO-CQSZACIVSA-N (1r)-1-[1-[3-(3-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(F)C=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 LQAWDGAFBLVCGO-CQSZACIVSA-N 0.000 description 2
- OJWJWXOLHNSREK-LBPRGKRZSA-N (1s)-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-LBPRGKRZSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 241000220479 Acacia Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229960002200 flunitrazepam Drugs 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 2
- 210000003928 nasal cavity Anatomy 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000003325 tomography Methods 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- QGCLEUGNYRXBMZ-ZCFIWIBFSA-N (1r)-1-(4-fluorophenyl)ethanamine Chemical compound C[C@@H](N)C1=CC=C(F)C=C1 QGCLEUGNYRXBMZ-ZCFIWIBFSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- DPRJPRMZJGWLHY-HNGSOEQISA-N (e,3r,5s)-7-[5-(4-fluorophenyl)-3-propan-2-yl-1-pyrazin-2-ylpyrazol-4-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)/C=C/C=1C(C(C)C)=NN(C=2N=CC=NC=2)C=1C1=CC=C(F)C=C1 DPRJPRMZJGWLHY-HNGSOEQISA-N 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- QEYQSYAGLRIYBE-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1,2-benzodiazepine Chemical class C1CCNNC2=CC=CC=C21 QEYQSYAGLRIYBE-UHFFFAOYSA-N 0.000 description 1
- RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 description 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- 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 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1c(*)c(S)c(*)c(*)c1* Chemical compound Cc1c(*)c(S)c(*)c(*)c1* 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 206010016275 Fear Diseases 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- HPKJGHVHQWJOOT-ZJOUEHCJSA-N N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide Chemical compound C1C(CCCC1)C[C@H](NC(=O)C=1NC2=CC=CC=C2C=1)C(=O)N[C@@H](C[C@H]1C(=O)NCC1)C=O HPKJGHVHQWJOOT-ZJOUEHCJSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- AEULIVPVIDOLIN-UHFFFAOYSA-N cep-11981 Chemical compound C1=C2C3=C4CNC(=O)C4=C4C5=CN(C)N=C5CCC4=C3N(CC(C)C)C2=CC=C1NC1=NC=CC=N1 AEULIVPVIDOLIN-UHFFFAOYSA-N 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 238000002591 computed tomography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229950005627 embonate Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002595 magnetic resonance imaging Methods 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- QYYDYYDGGZJJCS-UHFFFAOYSA-N n-(3-bromophenyl)formamide Chemical compound BrC1=CC=CC(NC=O)=C1 QYYDYYDGGZJJCS-UHFFFAOYSA-N 0.000 description 1
- AWVYIUGTVFUVFQ-OAHLLOKOSA-N n-[(1r)-1-[1-[3-(1,3-benzodioxol-4-yl)phenyl]benzimidazol-5-yl]ethyl]acetamide Chemical compound C1=NC2=CC([C@H](NC(C)=O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC2=C1OCO2 AWVYIUGTVFUVFQ-OAHLLOKOSA-N 0.000 description 1
- IDQNNPJLBVGCLN-ZETCQYMHSA-N n-[(1s)-1-(4-fluorophenyl)ethyl]acetamide Chemical compound CC(=O)N[C@@H](C)C1=CC=C(F)C=C1 IDQNNPJLBVGCLN-ZETCQYMHSA-N 0.000 description 1
- YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 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
- 125000005498 phthalate group Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000004291 polyenes Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
- 150000005671 trienes Chemical class 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Anesthesiology (AREA)
- Diabetes (AREA)
- Otolaryngology (AREA)
- Nutrition Science (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 |
|---|---|
| KR20080077620A true KR20080077620A (ko) | 2008-08-25 |
Family
ID=37873123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087013766A Withdrawn KR20080077620A (ko) | 2005-12-05 | 2006-12-04 | 벤즈이미다졸 및 ｇａｂａａ 수용체 복합체를 조절하기위한 이의 용도 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7923464B2 (enExample) |
| EP (1) | EP1996556B1 (enExample) |
| JP (1) | JP2009518292A (enExample) |
| KR (1) | KR20080077620A (enExample) |
| AT (1) | ATE449077T1 (enExample) |
| AU (1) | AU2006324046A1 (enExample) |
| CA (1) | CA2632395A1 (enExample) |
| DE (1) | DE602006010602D1 (enExample) |
| DK (1) | DK1996556T3 (enExample) |
| ES (1) | ES2335438T3 (enExample) |
| IL (1) | IL189974A0 (enExample) |
| NO (1) | NO20083045L (enExample) |
| PL (1) | PL1996556T3 (enExample) |
| WO (1) | WO2007065864A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2008345696A1 (en) * | 2007-12-21 | 2009-07-09 | Wyeth Llc | Benzimidazole compounds |
| CN102036952A (zh) * | 2008-04-16 | 2011-04-27 | 比奥里波克斯公司 | 用作药物的双芳基化合物 |
| US20110301192A1 (en) * | 2008-10-01 | 2011-12-08 | 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 |
| RS62761B1 (sr) * | 2012-08-21 | 2022-01-31 | Sage Therapeutics Inc | Alopregnanolon za lečenje refraktornog epileptičkog statusa |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK40192D0 (da) * | 1992-03-26 | 1992-03-26 | Neurosearch As | Imidazolforbindelser, deres fremstilling og anvendelse |
| CA2218493C (en) | 1995-04-21 | 2005-02-22 | Neurosearch A/S | Benzimidazole compounds and their use as modulators of the gabaa receptor complex |
| AU726447B2 (en) * | 1996-10-21 | 2000-11-09 | Neurosearch A/S | 1-phenyl-benzimidazole compounds and their use as BAGA-A receptor modulators |
| CN1275127A (zh) | 1997-10-10 | 2000-11-29 | 神经研究公司 | 苯并咪唑化合物、含该化合物的药物组合物及其应用 |
| BR0011823A (pt) * | 1999-06-22 | 2002-03-19 | Neurosearch As | Derivado de benzimidazol, composto, composição farmacêutica, uso de um derivado de benzimidazol, e, método para tratamento, prevenção ou alìvio de uma doença ou de um distúrbio ou de uma condição de um corpo animal vivo |
| AU2002221566A1 (en) | 2000-12-20 | 2002-07-01 | Neurosearch A/S | Novel benzimidazole derivatives for the treatment of gaba-alpha mediated disorders |
| MXPA05010449A (es) | 2003-04-03 | 2006-05-31 | Neurosearch As | Derivados del bencimidazol y su uso para modular el complejo del receptor de gabaa. |
| US7335777B2 (en) * | 2003-04-03 | 2008-02-26 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the GABAA receptor complex |
| BRPI0413746A (pt) * | 2003-08-21 | 2006-10-24 | Osi Pharm Inc | composto ou um seu n-óxido ou seu sal farmaceuticamente aceitável, composição, e, método de tratamento de distúrbio hiperproliferativo |
| EP1678144A1 (en) | 2003-10-23 | 2006-07-12 | Akzo Nobel N.V. | 1,5,7-TRISUBSTITUTED BENZIMIDAZOLE DERIVATIVES AND THEIR USE FOR MODULATING THE GABA-a RECEPTOR COMPLEX |
| CA2589770A1 (en) * | 2004-12-01 | 2006-06-08 | Osi Pharmaceuticals, Inc. | N-substituted benzimidazolyl c-kit inhibitors and combinatorial benzimidazole library |
| CA2604516A1 (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 |
-
2006
- 2006-12-04 US US12/085,769 patent/US7923464B2/en not_active Expired - Fee Related
- 2006-12-04 DE DE602006010602T patent/DE602006010602D1/de active Active
- 2006-12-04 EP EP06830303A patent/EP1996556B1/en not_active Not-in-force
- 2006-12-04 KR KR1020087013766A patent/KR20080077620A/ko not_active Withdrawn
- 2006-12-04 AT AT06830303T patent/ATE449077T1/de active
- 2006-12-04 CA CA002632395A patent/CA2632395A1/en not_active Abandoned
- 2006-12-04 ES ES06830303T patent/ES2335438T3/es active Active
- 2006-12-04 WO PCT/EP2006/069237 patent/WO2007065864A1/en not_active Ceased
- 2006-12-04 JP JP2008542778A patent/JP2009518292A/ja not_active Abandoned
- 2006-12-04 DK DK06830303.1T patent/DK1996556T3/da active
- 2006-12-04 AU AU2006324046A patent/AU2006324046A1/en not_active Abandoned
- 2006-12-04 PL PL06830303T patent/PL1996556T3/pl unknown
-
2008
- 2008-03-06 IL IL189974A patent/IL189974A0/en unknown
- 2008-07-04 NO NO20083045A patent/NO20083045L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20090048321A1 (en) | 2009-02-19 |
| DE602006010602D1 (de) | 2009-12-31 |
| ES2335438T3 (es) | 2010-03-26 |
| DK1996556T3 (da) | 2010-04-06 |
| JP2009518292A (ja) | 2009-05-07 |
| EP1996556A1 (en) | 2008-12-03 |
| ATE449077T1 (de) | 2009-12-15 |
| WO2007065864A1 (en) | 2007-06-14 |
| CA2632395A1 (en) | 2007-06-14 |
| US7923464B2 (en) | 2011-04-12 |
| NO20083045L (no) | 2008-09-04 |
| PL1996556T3 (pl) | 2010-05-31 |
| IL189974A0 (en) | 2008-08-07 |
| AU2006324046A1 (en) | 2007-06-14 |
| EP1996556B1 (en) | 2009-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20080111097A (ko) | 벤즈이미다졸 유도체 및 ｇａｂａａ 수용체 복합체를 조절하기 위한 이의 용도 | |
| US20060069135A1 (en) | Benzimidazole derivatives and their use for modulating the gaba-a receptor complex | |
| EP1996556B1 (en) | Benzimidazole derivatives and their use for modulating the gabaa receptor complex | |
| RS57071B1 (sr) | Jedinjenja fluorofenil pirazola | |
| US7939556B2 (en) | Imidazole derivatives and their use for modulating the GABAA receptor complex | |
| US7858649B2 (en) | Imidazole derivatives and their use for modulating the GABAA receptor complex | |
| US7335777B2 (en) | Benzimidazole derivatives and their use for modulating the GABAA receptor complex | |
| US7851490B2 (en) | Benzimidazole derivatives and their use for modulating the GABAA receptor complex | |
| CN102216290A (zh) | 苯并咪唑衍生物及其用于调节gabaa受体复合物的用途 | |
| US7776900B2 (en) | Benzimidazole derivatives and their use for modulating the GABAAreceptor complex | |
| EP1615896B1 (en) | Novel benzimidazole derivatives and pharmaceutical compositions comprising these compounds | |
| US20080312303A1 (en) | Imidazole Derivatives and Their Use for Modulating the Gabaa Receptor Complex | |
| US20090062304A1 (en) | Benzimidazole derivatives and their use for modulating the gaba-alpha receptor complex | |
| CN101291915A (zh) | 苯并咪唑衍生物及其用于调节gabaa受体复合物的用途 | |
| EP1874735A1 (en) | Benzimidazole derivatives and their use for modulating the gabaa receptor complex | |
| HK1116051A (en) | Benzimidazole derivatives and their use for modulating the gabaa receptor complex | |
| CN101141958A (zh) | 苯并咪唑衍生物及其用于调节gabaa受体复合物的用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20080605 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| 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 |