JP2008519805A - イミダゾ［１，２−ａ］ピリジン化合物、それに関連する組成物、使用及び方法 - Google Patents
イミダゾ［１，２−ａ］ピリジン化合物、それに関連する組成物、使用及び方法 Download PDFInfo
- Publication number
- JP2008519805A JP2008519805A JP2007540634A JP2007540634A JP2008519805A JP 2008519805 A JP2008519805 A JP 2008519805A JP 2007540634 A JP2007540634 A JP 2007540634A JP 2007540634 A JP2007540634 A JP 2007540634A JP 2008519805 A JP2008519805 A JP 2008519805A
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- JP
- Japan
- Prior art keywords
- methyl
- imidazo
- alkyl
- tolyl
- pyridin
- 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.)
- Pending
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- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 32
- 239000000203 mixture Substances 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- -1 monosubstituted naphthyl Chemical group 0.000 claims description 52
- 241000124008 Mammalia Species 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 206010022437 insomnia Diseases 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 206010039897 Sedation Diseases 0.000 claims description 11
- 230000007958 sleep Effects 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 230000036506 anxiety Effects 0.000 claims description 9
- 206010021118 Hypotonia Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 230000036640 muscle relaxation Effects 0.000 claims description 8
- 206010015037 epilepsy Diseases 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 206010002091 Anaesthesia Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- OMHFQABYXCKFDZ-UHFFFAOYSA-N [6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methanamine Chemical compound C1=CC(C)=CC=C1C1=C(CN)N2C=C(C)C=CC2=N1 OMHFQABYXCKFDZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000037005 anaesthesia Effects 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 208000019116 sleep disease Diseases 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- CESOHFKDGWQUPY-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-3-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NCC1=C(C=2C=CC(C)=CC=2)N=C2N1C=C(C)C=C2 CESOHFKDGWQUPY-UHFFFAOYSA-N 0.000 claims description 4
- UQVSSKZWNDYAIO-UHFFFAOYSA-N 4-(dimethylamino)-n-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N(C)CC1=C(C=2C=CC(C)=CC=2)N=C2N1C=C(C)C=C2 UQVSSKZWNDYAIO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- JWMKFHLKLVRHOT-UHFFFAOYSA-N phenyl n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]carbamate Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)OC=2C=CC=CC=2)N2C=C(C)C=CC2=N1 JWMKFHLKLVRHOT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- OTQIEJPVRTUEER-UHFFFAOYSA-N (4-methoxyphenyl) n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]carbamate Chemical compound C1=CC(OC)=CC=C1OC(=O)NCC1=C(C=2C=CC(C)=CC=2)N=C2N1C=C(C)C=C2 OTQIEJPVRTUEER-UHFFFAOYSA-N 0.000 claims description 3
- XXLCITZOTDRKBS-UHFFFAOYSA-N (4-methylphenyl) n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]carbamate Chemical compound C1=CC(C)=CC=C1OC(=O)NCC1=C(C=2C=CC(C)=CC=2)N=C2N1C=C(C)C=C2 XXLCITZOTDRKBS-UHFFFAOYSA-N 0.000 claims description 3
- WGJVDNCXMYRHBP-UHFFFAOYSA-N 1-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-3-propan-2-ylurea Chemical compound N1=C2C=CC(C)=CN2C(CNC(=O)NC(C)C)=C1C1=CC=C(C)C=C1 WGJVDNCXMYRHBP-UHFFFAOYSA-N 0.000 claims description 3
- NOUAWZHYQHTDEJ-UHFFFAOYSA-N 1-cyclohexyl-3-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]urea Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)NC2CCCCC2)N2C=C(C)C=CC2=N1 NOUAWZHYQHTDEJ-UHFFFAOYSA-N 0.000 claims description 3
- ZWRYJYABHHUFPU-UHFFFAOYSA-N 1-cyclopentyl-3-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]urea Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)NC2CCCC2)N2C=C(C)C=CC2=N1 ZWRYJYABHHUFPU-UHFFFAOYSA-N 0.000 claims description 3
- DWSPBIIPFKKTAQ-UHFFFAOYSA-N 1-ethyl-3-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]urea Chemical compound N1=C2C=CC(C)=CN2C(CNC(=O)NCC)=C1C1=CC=C(C)C=C1 DWSPBIIPFKKTAQ-UHFFFAOYSA-N 0.000 claims description 3
- BWLPSJCXJOBBAO-UHFFFAOYSA-N 1-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]imidazole-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2N(C=CN=2)C)N2C=C(C)C=CC2=N1 BWLPSJCXJOBBAO-UHFFFAOYSA-N 0.000 claims description 3
- FKTNIUYWLOMCAO-UHFFFAOYSA-N 2,5-dimethyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NCC=2N3C=C(C)C=CC3=NC=2C=2C=CC(C)=CC=2)=C1C FKTNIUYWLOMCAO-UHFFFAOYSA-N 0.000 claims description 3
- PUVUXUVTNYRZDQ-UHFFFAOYSA-N 3,5-difluoro-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]pyridine-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2C(=CC(F)=CN=2)F)N2C=C(C)C=CC2=N1 PUVUXUVTNYRZDQ-UHFFFAOYSA-N 0.000 claims description 3
- CPWODVBXRXLLRO-UHFFFAOYSA-N 3,5-dimethyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C(=O)NCC1=C(C=2C=CC(C)=CC=2)N=C2N1C=C(C)C=C2 CPWODVBXRXLLRO-UHFFFAOYSA-N 0.000 claims description 3
- RDGHSFLKJOYRPN-UHFFFAOYSA-N 5-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]pyrazine-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2N=CC(C)=NC=2)N2C=C(C)C=CC2=N1 RDGHSFLKJOYRPN-UHFFFAOYSA-N 0.000 claims description 3
- XISYQKZHJGFKHV-UHFFFAOYSA-N 6-methoxy-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazole-2-carboxamide Chemical compound S1C2=CC(OC)=CC=C2N=C1C(=O)NCC(N1C=C(C)C=CC1=N1)=C1C1=CC=C(C)C=C1 XISYQKZHJGFKHV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- LDIKCXZKVGDJNF-UHFFFAOYSA-N benzyl n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]carbamate Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)OCC=2C=CC=CC=2)N2C=C(C)C=CC2=N1 LDIKCXZKVGDJNF-UHFFFAOYSA-N 0.000 claims description 3
- DAJCGNDSCWPLDH-UHFFFAOYSA-N ethyl n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]carbamate Chemical compound N1=C2C=CC(C)=CN2C(CNC(=O)OCC)=C1C1=CC=C(C)C=C1 DAJCGNDSCWPLDH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- RNFARXKWDQJNLG-UHFFFAOYSA-N methyl n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]carbamate Chemical compound N1=C2C=CC(C)=CN2C(CNC(=O)OC)=C1C1=CC=C(C)C=C1 RNFARXKWDQJNLG-UHFFFAOYSA-N 0.000 claims description 3
- DWDVCWCLBVSPLX-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-thiazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2N=CSC=2)N2C=C(C)C=CC2=N1 DWDVCWCLBVSPLX-UHFFFAOYSA-N 0.000 claims description 3
- AWRLGWNAYODVRB-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-2-thiophen-2-ylacetamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)CC=2SC=CC=2)N2C=C(C)C=CC2=N1 AWRLGWNAYODVRB-UHFFFAOYSA-N 0.000 claims description 3
- HCRNXOBUKNXIHO-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-5-nitrofuran-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2OC(=CC=2)[N+]([O-])=O)N2C=C(C)C=CC2=N1 HCRNXOBUKNXIHO-UHFFFAOYSA-N 0.000 claims description 3
- PTWSRSSUDHMUHJ-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-6-oxo-4,5-dihydro-1h-pyridazine-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2CCC(=O)NN=2)N2C=C(C)C=CC2=N1 PTWSRSSUDHMUHJ-UHFFFAOYSA-N 0.000 claims description 3
- YGGVBKKFXOLFRC-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]cyclobutanecarboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C2CCC2)N2C=C(C)C=CC2=N1 YGGVBKKFXOLFRC-UHFFFAOYSA-N 0.000 claims description 3
- QMHMFZOKGJUXMK-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]cyclopropanecarboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C2CC2)N2C=C(C)C=CC2=N1 QMHMFZOKGJUXMK-UHFFFAOYSA-N 0.000 claims description 3
- OLQGTBXDUWNKNJ-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]furan-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2OC=CC=2)N2C=C(C)C=CC2=N1 OLQGTBXDUWNKNJ-UHFFFAOYSA-N 0.000 claims description 3
- BRISNIQLIFKHEV-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]pyridine-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2N=CC=CC=2)N2C=C(C)C=CC2=N1 BRISNIQLIFKHEV-UHFFFAOYSA-N 0.000 claims description 3
- YKBOXUAMTQGXGC-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]thiadiazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2N=NSC=2)N2C=C(C)C=CC2=N1 YKBOXUAMTQGXGC-UHFFFAOYSA-N 0.000 claims description 3
- SEMIQJYZQISRDK-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2SC=CC=2)N2C=C(C)C=CC2=N1 SEMIQJYZQISRDK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001326 naphthylalkyl group Chemical group 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- GYPIEUFQDFPIIT-UHFFFAOYSA-N prop-2-ynyl n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]carbamate Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)OCC#C)N2C=C(C)C=CC2=N1 GYPIEUFQDFPIIT-UHFFFAOYSA-N 0.000 claims description 3
- IMDAQKCLUXUBAO-UHFFFAOYSA-N 2-chloro-n-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]pyridine-4-carboxamide Chemical compound C=1C=NC(Cl)=CC=1C(=O)N(C)CC(N1C=C(C)C=CC1=N1)=C1C1=CC=C(C)C=C1 IMDAQKCLUXUBAO-UHFFFAOYSA-N 0.000 claims description 2
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical group OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 208000022925 sleep disturbance Diseases 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 3
- 230000006806 disease prevention Effects 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 48
- 102000005962 receptors Human genes 0.000 description 39
- 108020003175 receptors Proteins 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 235000011054 acetic acid Nutrition 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 230000000147 hypnotic effect Effects 0.000 description 8
- 230000006698 induction Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- 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
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| EP04105698 | 2004-11-11 | ||
| PCT/EP2005/055753 WO2006051063A1 (en) | 2004-11-11 | 2005-11-04 | Imidazo[1,2-a]pyridine compounds, compositions, uses and methods related thereto |
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| JP2008519805A true JP2008519805A (ja) | 2008-06-12 |
| JP2008519805A5 JP2008519805A5 (https=) | 2008-12-18 |
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| EP (1) | EP1814880B1 (https=) |
| JP (1) | JP2008519805A (https=) |
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| PE (1) | PE20060967A1 (https=) |
| PL (1) | PL1814880T3 (https=) |
| PT (1) | PT1814880E (https=) |
| RU (1) | RU2007121864A (https=) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012510983A (ja) * | 2008-12-04 | 2012-05-17 | プロキシマジェン エルティーディー | イミダゾピリジン化合物 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2477604A1 (en) | 2002-03-13 | 2003-09-25 | Signum Biosciences, Inc. | Modulation of protein methylation and phosphoprotein phosphate |
| WO2006084033A1 (en) | 2005-02-03 | 2006-08-10 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| EP1845098A1 (en) * | 2006-03-29 | 2007-10-17 | Ferrer Internacional, S.A. | Imidazo[1,2-b]pyridazines, their processes of preparation and their use as GABA receptor ligands |
| AU2007267183B2 (en) * | 2006-05-31 | 2011-10-20 | F. Hoffmann-La Roche Ag | Aryl-4-ethynyl-isoxazole derivatives |
| CN101528226B (zh) * | 2006-08-24 | 2012-01-11 | 澳大利亚核科学技术组织 | 靶向外周苯二氮卓受体的氟化配体 |
| JP5607025B2 (ja) | 2008-04-21 | 2014-10-15 | シグナム バイオサイエンシーズ， インコーポレイテッド | 化合物、組成物およびそれらを作製する方法 |
| CA2724842A1 (en) * | 2008-05-19 | 2009-11-26 | Sunovion Pharmaceuticals Inc. | Imidazo[1,2-a]pyridine compounds |
| US10478438B2 (en) | 2008-10-16 | 2019-11-19 | David Reed Helton | Treatment of organophosphate exposure with ocinaplon |
| EP2496578A4 (en) | 2009-11-05 | 2013-08-21 | Univ Notre Dame Du Lac | IMIDAZO [1,2-A] PYRIDINE COMPOUNDS, THEIR SYNTHESIS AND METHODS OF USE THEREOF |
| TW201225957A (en) | 2010-09-17 | 2012-07-01 | Taisho Pharmaceutical Co Ltd | Glycine transporter inhibitor |
| KR20180053386A (ko) | 2015-09-17 | 2018-05-21 | 마빈 제이. 밀러 | 마이코박테리아 감염에 대해 유용한 벤질 아민-함유 헤테로사이클릭 화합물 및 조성물 |
| WO2017087885A1 (en) | 2015-11-19 | 2017-05-26 | Dana-Farber Cancer Institute, Inc. | Methods of identifying compounds that interfere with erg-driven misguidance of baf complexes in tmprss2-erg driven prostate cancers |
| CN106906486B (zh) * | 2017-02-22 | 2018-12-11 | 华南理工大学 | 3-溴-2-苯基-咪唑并[1,2-α]吡啶类衍生物的电化学合成方法 |
| WO2019152437A1 (en) | 2018-01-30 | 2019-08-08 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| WO2020081588A1 (en) | 2018-10-17 | 2020-04-23 | Dana-Farber Cancer Institute, Inc. | Swi/snf family chromatin remodeling complexes and uses thereof |
| US12384776B2 (en) | 2019-01-29 | 2025-08-12 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| WO2020160100A1 (en) | 2019-01-29 | 2020-08-06 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| US20230121497A1 (en) * | 2020-01-29 | 2023-04-20 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| CA3167275A1 (en) | 2020-01-29 | 2021-08-05 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| US12383555B2 (en) | 2020-05-20 | 2025-08-12 | Foghorn Therapeutics Inc. | Methods of treating cancers |
| JP2024509268A (ja) | 2021-03-09 | 2024-02-29 | フォグホーン セラピューティクス インコーポレイテッド | 結晶形、それらを含有する組成物、及びそれらの使用方法 |
| CN118515663A (zh) * | 2023-04-24 | 2024-08-20 | 上海赛默罗生物科技有限公司 | 咪唑并吡啶或咪唑并吡嗪类化合物、其制备方法、药物组合物和用途 |
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| JPS6147485A (ja) * | 1984-08-07 | 1986-03-07 | シンセラボ | ３‐アシルアミノメチルイミダゾ［１，２‐ａ］ピリジン誘導体 |
| JPS62169784A (ja) * | 1986-01-22 | 1987-07-25 | シンセラボ | ３−（アシルアミノメチル）イミダゾ〔１，２−ａ〕ピリジン誘導体、その製造法およびその医薬への応用 |
| US4767755A (en) * | 1986-02-05 | 1988-08-30 | Synthelabo | 3-(acylaminomethyl)imidazo[1,2-a]pyridine derivatives and pharmaceutical compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE62687T1 (de) * | 1986-01-22 | 1991-05-15 | Synthelabo | Acylaminomethylimidazo(1,2-a>pyrimidinderivate, ihre herstellung und therapeutische verwendung. |
| US20040204443A1 (en) * | 2003-01-27 | 2004-10-14 | Arthur Zaks | Method for inducing pain relief using imidazo[1,2-a]pyridine derivatives |
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2005
- 2005-11-04 DK DK05808135T patent/DK1814880T3/da active
- 2005-11-04 US US11/667,494 patent/US20080200473A1/en not_active Abandoned
- 2005-11-04 KR KR1020077010318A patent/KR20070084026A/ko not_active Ceased
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- 2005-11-04 ES ES05808135T patent/ES2321858T3/es not_active Expired - Lifetime
- 2005-11-04 MX MX2007005611A patent/MX2007005611A/es active IP Right Grant
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- 2005-11-04 AU AU2005303811A patent/AU2005303811A1/en not_active Abandoned
- 2005-11-04 BR BRPI0517796-0A patent/BRPI0517796A/pt not_active IP Right Cessation
- 2005-11-04 PT PT05808135T patent/PT1814880E/pt unknown
- 2005-11-04 WO PCT/EP2005/055753 patent/WO2006051063A1/en not_active Ceased
- 2005-11-04 EP EP05808135A patent/EP1814880B1/en not_active Expired - Lifetime
- 2005-11-04 JP JP2007540634A patent/JP2008519805A/ja active Pending
- 2005-11-04 CN CN2005800386913A patent/CN101065377B/zh not_active Expired - Fee Related
- 2005-11-04 CA CA002585315A patent/CA2585315A1/en not_active Abandoned
- 2005-11-04 PL PL05808135T patent/PL1814880T3/pl unknown
- 2005-11-04 RU RU2007121864/04A patent/RU2007121864A/ru not_active Application Discontinuation
- 2005-11-07 PE PE2005001302A patent/PE20060967A1/es not_active Application Discontinuation
- 2005-11-08 PA PA20058652101A patent/PA8652101A1/es unknown
- 2005-11-08 TW TW094139042A patent/TWI357412B/zh not_active IP Right Cessation
- 2005-11-09 AR ARP050104693A patent/AR051626A1/es not_active Application Discontinuation
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2007
- 2007-05-03 IL IL182963A patent/IL182963A0/en unknown
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| JPS6147485A (ja) * | 1984-08-07 | 1986-03-07 | シンセラボ | ３‐アシルアミノメチルイミダゾ［１，２‐ａ］ピリジン誘導体 |
| JPS62169784A (ja) * | 1986-01-22 | 1987-07-25 | シンセラボ | ３−（アシルアミノメチル）イミダゾ〔１，２−ａ〕ピリジン誘導体、その製造法およびその医薬への応用 |
| US4767755A (en) * | 1986-02-05 | 1988-08-30 | Synthelabo | 3-(acylaminomethyl)imidazo[1,2-a]pyridine derivatives and pharmaceutical compositions |
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| JPN5007019833; ＡＬＭＩＲＡＮＴＥ Ｌ: ＢＯＬＬＥＴＴＩＮＯ ＣＨＩＭＩＣＯ ＦＡＲＭＡＣＥＵＴＩＣＯ Ｖ１１０ Ｎ６, 1971, Ｐ３２２-３２９, ＳＯＣＩＥＴＡ ＥＤＩＴＯＲＩＡＬＥ ＦＡＲＭＡＣＥＵＴＩＣＡ * |
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| JPN6011059566; Ｂａｒｌｉｎ，Ｇ．Ｂ: Ｊｏｕｒｎａｌ ｏｆ Ｈｅｔｅｒｏｃｙｃｌｉｃ Ｃｈｅｍｉｓｔｒｙ Ｖｏｌ．３５, 1998, ｐｐ １２０５-１２１７ * |
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| JPN6011059569; Ｂａｒｌｉｎ．Ｇ．Ｂ．ｅｔ ａｌ: Ａｕｓｔｒａｌｉａｎ Ｊｏｕｒｎａｌ ｏｆ Ｃｈｅｍｉｓｔｒｙ Ｖｏｌ．４９, 1996, ｐｐ ４５１-４６１ * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012510983A (ja) * | 2008-12-04 | 2012-05-17 | プロキシマジェン エルティーディー | イミダゾピリジン化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1814880A1 (en) | 2007-08-08 |
| AR051626A1 (es) | 2007-01-24 |
| CN101065377B (zh) | 2011-07-27 |
| PA8652101A1 (es) | 2006-10-13 |
| UY29204A1 (es) | 2006-01-31 |
| PE20060967A1 (es) | 2006-09-20 |
| CA2585315A1 (en) | 2006-05-18 |
| MX2007005611A (es) | 2007-07-11 |
| EP1814880B1 (en) | 2009-01-28 |
| DE602005012598D1 (de) | 2009-03-19 |
| TW200624432A (en) | 2006-07-16 |
| PL1814880T3 (pl) | 2009-07-31 |
| ATE421962T1 (de) | 2009-02-15 |
| IL182963A0 (en) | 2007-08-19 |
| WO2006051063A1 (en) | 2006-05-18 |
| RU2007121864A (ru) | 2008-12-20 |
| BRPI0517796A (pt) | 2008-10-28 |
| PT1814880E (pt) | 2009-04-23 |
| TWI357412B (en) | 2012-02-01 |
| AU2005303811A1 (en) | 2006-05-18 |
| CN101065377A (zh) | 2007-10-31 |
| ES2321858T3 (es) | 2009-06-12 |
| US20080200473A1 (en) | 2008-08-21 |
| KR20070084026A (ko) | 2007-08-24 |
| DK1814880T3 (da) | 2009-05-18 |
| NO20072831L (no) | 2007-08-01 |
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