AU2005303811A1 - Imidazo(1,2-a)pyridine compounds, compositions, uses and methods related thereto - Google Patents
Imidazo(1,2-a)pyridine compounds, compositions, uses and methods related thereto Download PDFInfo
- Publication number
- AU2005303811A1 AU2005303811A1 AU2005303811A AU2005303811A AU2005303811A1 AU 2005303811 A1 AU2005303811 A1 AU 2005303811A1 AU 2005303811 A AU2005303811 A AU 2005303811A AU 2005303811 A AU2005303811 A AU 2005303811A AU 2005303811 A1 AU2005303811 A1 AU 2005303811A1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- imidazo
- tolyl
- ylmethyl
- substituted
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 32
- 239000000203 mixture Substances 0.000 title claims description 17
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 84
- -1 monosubstituted naphthyl Chemical group 0.000 claims description 43
- 150000001408 amides Chemical class 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 241000124008 Mammalia Species 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 102000005962 receptors Human genes 0.000 claims description 24
- 108020003175 receptors Proteins 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 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
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 102000027484 GABAA receptors Human genes 0.000 claims description 13
- 108091008681 GABAA receptors Proteins 0.000 claims description 13
- 239000004202 carbamide Substances 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 206010022437 insomnia Diseases 0.000 claims description 13
- 230000007958 sleep Effects 0.000 claims description 11
- 206010039897 Sedation Diseases 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 230000036506 anxiety Effects 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 206010021118 Hypotonia Diseases 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 230000036640 muscle relaxation Effects 0.000 claims description 8
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 8
- 125000006528 (C2-C6) alkyl group Chemical group 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
- 230000037005 anaesthesia Effects 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=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
- 206010015037 epilepsy Diseases 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
- 230000001939 inductive effect Effects 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000842 isoxazolyl 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
- 239000002253 acid Substances 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- WLDPWZQYAVZTTP-UHFFFAOYSA-N 1-methyl-imidazole-2-carboxylic acid Chemical compound CN1C=CN=C1C(O)=O WLDPWZQYAVZTTP-UHFFFAOYSA-N 0.000 claims description 4
- LHGRUGVXZLHYKE-UHFFFAOYSA-N 2,5-dimethyl-1,3-oxazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=C(C)O1 LHGRUGVXZLHYKE-UHFFFAOYSA-N 0.000 claims description 4
- QKLXAJQKMIWFRC-UHFFFAOYSA-N 3,5-difluoropyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C(F)C=C1F QKLXAJQKMIWFRC-UHFFFAOYSA-N 0.000 claims description 4
- IODMEDPPCXSFLD-UHFFFAOYSA-N 5-nitrofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)O1 IODMEDPPCXSFLD-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
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 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
- IJEUISLJVBUNRE-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C(O)=O IJEUISLJVBUNRE-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- RBYJWCRKFLGNDB-UHFFFAOYSA-N 5-methylpyrazine-2-carboxylic acid Chemical compound CC1=CN=C(C(O)=O)C=N1 RBYJWCRKFLGNDB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001326 naphthylalkyl group Chemical group 0.000 claims description 3
- HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 3
- NIHHYKUHSZFXTC-UHFFFAOYSA-N (4-methoxyphenyl) carbamate Chemical compound COC1=CC=C(OC(N)=O)C=C1 NIHHYKUHSZFXTC-UHFFFAOYSA-N 0.000 claims description 2
- CAOOVUTXOZVQON-UHFFFAOYSA-N (4-methylphenyl) carbamate Chemical compound CC1=CC=C(OC(N)=O)C=C1 CAOOVUTXOZVQON-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- KBRSJPHSCOAFDR-UHFFFAOYSA-N 3-chloro-6-methyl-5,5-dioxo-11h-benzo[c][2,1]benzothiazepin-11-ol Chemical compound O=S1(=O)N(C)C2=CC=CC=C2C(O)C2=CC=C(Cl)C=C21 KBRSJPHSCOAFDR-UHFFFAOYSA-N 0.000 claims description 2
- VUADWGRLHPTYPI-UHFFFAOYSA-N 6-oxo-4,5-dihydro-1h-pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=NNC(=O)CC1 VUADWGRLHPTYPI-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- KLVOLCWZIUJXJB-UHFFFAOYSA-N n-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-thiazole-4-carboxamide Chemical compound C=1SC=NC=1C(=O)N(C)CC(N1C=C(C)C=CC1=N1)=C1C1=CC=C(C)C=C1 KLVOLCWZIUJXJB-UHFFFAOYSA-N 0.000 claims description 2
- MZIYTZLXEWAXOF-UHFFFAOYSA-N n-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)N(C)CC(N1C=C(C)C=CC1=N1)=C1C1=CC=C(C)C=C1 MZIYTZLXEWAXOF-UHFFFAOYSA-N 0.000 claims description 2
- YSOFNHDSQMGJHU-UHFFFAOYSA-N n-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)N(C)CC(N1C=C(C)C=CC1=N1)=C1C1=CC=C(C)C=C1 YSOFNHDSQMGJHU-UHFFFAOYSA-N 0.000 claims description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- QVCOXWYMPCBIMH-UHFFFAOYSA-N prop-2-ynyl carbamate Chemical compound NC(=O)OCC#C QVCOXWYMPCBIMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 3
- 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
- 125000006727 (C1-C6) alkenyl group Chemical group 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 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
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 150000001263 acyl chlorides Chemical class 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
- 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 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 100
- 238000005481 NMR spectroscopy Methods 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 230000006698 induction Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 7
- 229960001475 zolpidem Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 229940049706 benzodiazepine Drugs 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 5
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 5
- 229960003529 diazepam Drugs 0.000 description 5
- 230000000147 hypnotic effect Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- LMZXAZWYORVELV-UHFFFAOYSA-N [6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1=CC(C)=CC=C1C1=C(CO)N2C=C(C)C=CC2=N1 LMZXAZWYORVELV-UHFFFAOYSA-N 0.000 description 4
- 150000003927 aminopyridines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 150000001557 benzodiazepines Chemical class 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- OFBIFZUFASYYRE-UHFFFAOYSA-N flumazenil Chemical compound C1N(C)C(=O)C2=CC(F)=CC=C2N2C=NC(C(=O)OCC)=C21 OFBIFZUFASYYRE-UHFFFAOYSA-N 0.000 description 4
- 229960004381 flumazenil Drugs 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000036280 sedation Effects 0.000 description 4
- 210000000278 spinal cord Anatomy 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 4
- 229960004010 zaleplon Drugs 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- JNDSPVJWQQFRSY-UHFFFAOYSA-N 4-(dimethylamino)-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)NCC1=C(C=2C=CC(C)=CC=2)N=C2N1C=C(C)C=C2 JNDSPVJWQQFRSY-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003326 hypnotic agent Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 230000009870 specific binding Effects 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 description 2
- PXRXGHUTKHXUGF-UHFFFAOYSA-N 1,5-dimethylpyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1C PXRXGHUTKHXUGF-UHFFFAOYSA-N 0.000 description 2
- WZTRQGJMMHMFGH-UHFFFAOYSA-N 1-methyl-imidazole-4-carboxylic acid Chemical compound CN1C=NC(C(O)=O)=C1 WZTRQGJMMHMFGH-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- IFLKEBSJTZGCJG-UHFFFAOYSA-N 3-methylthiophene-2-carboxylic acid Chemical compound CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 description 2
- VNJUNWUOAKEIKG-UHFFFAOYSA-N 5-nitrothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC([N+]([O-])=O)=C1 VNJUNWUOAKEIKG-UHFFFAOYSA-N 0.000 description 2
- JDKMYJZEGZZJOH-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazole-2-carboxylic acid Chemical compound COC1=CC=C2N=C(C(O)=O)SC2=C1 JDKMYJZEGZZJOH-UHFFFAOYSA-N 0.000 description 2
- AWEWSJJCANQFRB-UHFFFAOYSA-N 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(C)=CC=C1C1=CN(C=C(C)C=C2)C2=N1 AWEWSJJCANQFRB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010019133 Hangover Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CBIAWPMZSFFRGN-UHFFFAOYSA-N Indiplon Chemical compound CC(=O)N(C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C(=O)C=2SC=CC=2)=C1 CBIAWPMZSFFRGN-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
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 208000004793 anterograde amnesia Diseases 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 210000001638 cerebellum Anatomy 0.000 description 2
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229950003867 indiplon Drugs 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 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 description 2
- UGXNWVADASEYCP-UHFFFAOYSA-N n-ethyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(=O)N(CC)CC(N1C=C(C)C=CC1=N1)=C1C1=CC=C(C)C=C1 UGXNWVADASEYCP-UHFFFAOYSA-N 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- OQJFBUOFGHPMSR-UHFFFAOYSA-N ocinaplon Chemical compound C=1C=CC=NC=1C(=O)C(=C1N=CC=2)C=NN1C=2C1=CC=NC=C1 OQJFBUOFGHPMSR-UHFFFAOYSA-N 0.000 description 2
- 229950010328 ocinaplon Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 2
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 2
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 2
- 230000004799 sedative–hypnotic effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 description 1
- JTEBLTWGSAXWEE-UHFFFAOYSA-N 1,2,5-trimethylpyrrole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C)N1C JTEBLTWGSAXWEE-UHFFFAOYSA-N 0.000 description 1
- WUIJCMJIYQWIMF-UHFFFAOYSA-N 1,3-benzothiazole;hydroiodide Chemical compound [I-].C1=CC=C2SC=[NH+]C2=C1 WUIJCMJIYQWIMF-UHFFFAOYSA-N 0.000 description 1
- NDJXNNQYGYBVNQ-UHFFFAOYSA-N 1,5-dimethylpyrrole-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)N1C NDJXNNQYGYBVNQ-UHFFFAOYSA-N 0.000 description 1
- DRBLTQNCQJXSNU-UHFFFAOYSA-N 1-benzothiophene-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CSC2=C1 DRBLTQNCQJXSNU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- VOOZJPFNBFNPEK-UHFFFAOYSA-N 1-cyclopropyl-2,5-dimethylpyrrole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C)N1C1CC1 VOOZJPFNBFNPEK-UHFFFAOYSA-N 0.000 description 1
- QAMPBVPSOZEYTC-UHFFFAOYSA-N 1-methyl-6-oxo-4,5-dihydropyridazine-3-carboxylic acid Chemical compound CN1N=C(C(O)=O)CCC1=O QAMPBVPSOZEYTC-UHFFFAOYSA-N 0.000 description 1
- HVRCLXXJIQTXHC-UHFFFAOYSA-N 1-methylindole-3-carboxylic acid Chemical compound C1=CC=C2N(C)C=C(C(O)=O)C2=C1 HVRCLXXJIQTXHC-UHFFFAOYSA-N 0.000 description 1
- ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- PHYDLUSJJFZNFG-UHFFFAOYSA-N 2,1-benzoxazole-3-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)ON=C21 PHYDLUSJJFZNFG-UHFFFAOYSA-N 0.000 description 1
- ORDWBPTZFQDAQW-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]pyridine-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2C(=C(F)N=C(F)C=2F)F)N2C=C(C)C=CC2=N1 ORDWBPTZFQDAQW-UHFFFAOYSA-N 0.000 description 1
- KRVGXFREOJHJAX-UHFFFAOYSA-N 2-bromo-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)CBr)C=C1 KRVGXFREOJHJAX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ZHDRDZMTEOIWSX-UHFFFAOYSA-N 2-methyl-1,3-thiazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=CS1 ZHDRDZMTEOIWSX-UHFFFAOYSA-N 0.000 description 1
- IVSGNISQFORLHJ-UHFFFAOYSA-N 2-propyl-4-(trifluoromethyl)benzamide Chemical compound CCCC1=CC(C(F)(F)F)=CC=C1C(N)=O IVSGNISQFORLHJ-UHFFFAOYSA-N 0.000 description 1
- ZHTPRJUAGVRILQ-UHFFFAOYSA-N 3-(furan-2-yl)-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]prop-2-enamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=CC=2OC=CC=2)N2C=C(C)C=CC2=N1 ZHTPRJUAGVRILQ-UHFFFAOYSA-N 0.000 description 1
- NUAZYMKFAJODKI-UHFFFAOYSA-N 3-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]furan-2-carboxamide Chemical compound C1=COC(C(=O)NCC=2N3C=C(C)C=CC3=NC=2C=2C=CC(C)=CC=2)=C1C NUAZYMKFAJODKI-UHFFFAOYSA-N 0.000 description 1
- ZFEHQZVNKOESSZ-UHFFFAOYSA-N 4,5-dichloro-1,2-thiazole-3-carboxylic acid Chemical compound OC(=O)C1=NSC(Cl)=C1Cl ZFEHQZVNKOESSZ-UHFFFAOYSA-N 0.000 description 1
- JYMNQRQQBJIMCV-UHFFFAOYSA-N 4-(dimethylamino)benzonitrile Chemical compound CN(C)C1=CC=C(C#N)C=C1 JYMNQRQQBJIMCV-UHFFFAOYSA-N 0.000 description 1
- FDJOPYZBXQGHFL-UHFFFAOYSA-N 4-methoxy-n-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N(C)CC1=C(C=2C=CC(C)=CC=2)N=C2N1C=C(C)C=C2 FDJOPYZBXQGHFL-UHFFFAOYSA-N 0.000 description 1
- KEYPLCJVNVJJQK-UHFFFAOYSA-N 4-methoxythiophene-3-carboxylic acid Chemical compound COC1=CSC=C1C(O)=O KEYPLCJVNVJJQK-UHFFFAOYSA-N 0.000 description 1
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 description 1
- CEOFOUVVEMMYDW-UHFFFAOYSA-N 5-chloro-4-methoxythiophene-3-carboxylic acid Chemical compound COC1=C(Cl)SC=C1C(O)=O CEOFOUVVEMMYDW-UHFFFAOYSA-N 0.000 description 1
- ILLPXKQRQUSURG-UHFFFAOYSA-N 5-methoxythiophene-2-carboxylic acid Chemical compound COC1=CC=C(C(O)=O)S1 ILLPXKQRQUSURG-UHFFFAOYSA-N 0.000 description 1
- BNMPIJWVMVNSRD-UHFFFAOYSA-N 5-methyl-1,2-oxazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NO1 BNMPIJWVMVNSRD-UHFFFAOYSA-N 0.000 description 1
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- XIQQAIQZABTSNZ-UHFFFAOYSA-N 6-methoxy-2-oxochromene-3-carboxylic acid Chemical compound O1C(=O)C(C(O)=O)=CC2=CC(OC)=CC=C21 XIQQAIQZABTSNZ-UHFFFAOYSA-N 0.000 description 1
- FSVUKYUIBWKSMS-UHFFFAOYSA-N 6-methyl-2-(4-methylphenyl)-1h-imidazo[1,2-a]pyridin-4-ium;bromide Chemical compound [Br-].C1=CC(C)=CC=C1C1=C[N+]2=CC(C)=CC=C2N1 FSVUKYUIBWKSMS-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229940121985 Non-benzodiazepine hypnotic Drugs 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 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 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 231100000749 chronicity Toxicity 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 230000002397 epileptogenic effect Effects 0.000 description 1
- 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 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
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000000524 functional group Chemical class 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 235000011187 glycerol Nutrition 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
- 150000005232 imidazopyridines Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- COHYTHOBJLSHDF-BUHFOSPRSA-N indigo dye Chemical compound N\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-BUHFOSPRSA-N 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000004179 indigotine Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000000670 ligand binding assay Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 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 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- SGNYVKYUZORPLM-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2C=CC(=CC=2)C(F)(F)F)N2C=C(C)C=CC2=N1 SGNYVKYUZORPLM-UHFFFAOYSA-N 0.000 description 1
- ANDBFIALSWZWAW-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]-n-propyl-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(=O)N(CCC)CC(N1C=C(C)C=CC1=N1)=C1C1=CC=C(C)C=C1 ANDBFIALSWZWAW-UHFFFAOYSA-N 0.000 description 1
- KCVRMQHMHKXMHJ-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]pyridine-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2C=NC=CC=2)N2C=C(C)C=CC2=N1 KCVRMQHMHKXMHJ-UHFFFAOYSA-N 0.000 description 1
- IYBAWVQKEFAASR-UHFFFAOYSA-N n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]pyridine-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(CNC(=O)C=2C=CN=CC=2)N2C=C(C)C=CC2=N1 IYBAWVQKEFAASR-UHFFFAOYSA-N 0.000 description 1
- KZXCLYFCLOKFBZ-UHFFFAOYSA-N n-methyl-n-[[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl]pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)N(C)CC(N1C=C(C)C=CC1=N1)=C1C1=CC=C(C)C=C1 KZXCLYFCLOKFBZ-UHFFFAOYSA-N 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229940098462 oral drops Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000011422 pharmacological therapy Methods 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 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 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- GNJXXMQEARZTCP-UHFFFAOYSA-N propan-2-yl 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(C)C)=C1C1=CC=C(C)C=C1 GNJXXMQEARZTCP-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 230000036385 rapid eye movement (rem) sleep Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000007428 synaptic transmission, GABAergic Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 208000016254 weariness Diseases 0.000 description 1
- 229960000820 zopiclone Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- 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
- A61K31/435—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
- A61P25/08—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
- A61P25/20—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
- A61P25/28—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04105698.7 | 2004-11-11 | ||
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005303811A1 true AU2005303811A1 (en) | 2006-05-18 |
Family
ID=34929843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005303811A Abandoned AU2005303811A1 (en) | 2004-11-11 | 2005-11-04 | Imidazo(1,2-a)pyridine compounds, compositions, uses and methods related thereto |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20080200473A1 (https=) |
| EP (1) | EP1814880B1 (https=) |
| JP (1) | JP2008519805A (https=) |
| KR (1) | KR20070084026A (https=) |
| CN (1) | CN101065377B (https=) |
| AR (1) | AR051626A1 (https=) |
| AT (1) | ATE421962T1 (https=) |
| AU (1) | AU2005303811A1 (https=) |
| BR (1) | BRPI0517796A (https=) |
| CA (1) | CA2585315A1 (https=) |
| DE (1) | DE602005012598D1 (https=) |
| DK (1) | DK1814880T3 (https=) |
| ES (1) | ES2321858T3 (https=) |
| IL (1) | IL182963A0 (https=) |
| MX (1) | MX2007005611A (https=) |
| NO (1) | NO20072831L (https=) |
| PA (1) | PA8652101A1 (https=) |
| PE (1) | PE20060967A1 (https=) |
| PL (1) | PL1814880T3 (https=) |
| PT (1) | PT1814880E (https=) |
| RU (1) | RU2007121864A (https=) |
| TW (1) | TWI357412B (https=) |
| UY (1) | UY29204A1 (https=) |
| WO (1) | WO2006051063A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1483283A4 (en) | 2002-03-13 | 2007-04-11 | Signum Biosciences Inc | MODULATION OF PROTEIN METHYLATION AND PHOSPHOPROTEIN PHOSPHATE |
| CA2601777A1 (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 |
| MX2008014796A (es) * | 2006-05-31 | 2008-12-02 | Hoffmann La Roche | Derivados de aril-4-etinil-isoxazol. |
| AU2007288124B2 (en) * | 2006-08-24 | 2013-04-04 | Australian Nuclear Science & Technology Organisation | Fluorinated ligands for targeting peripheral benzodiazepine receptors |
| AU2009239430B2 (en) | 2008-04-21 | 2015-01-22 | Signum Biosciences, Inc. | Compounds, compositions and methods for making the same |
| CA2724842A1 (en) | 2008-05-19 | 2009-11-26 | Sunovion Pharmaceuticals Inc. | Imidazo[1,2-a]pyridine compounds |
| WO2010045615A2 (en) | 2008-10-16 | 2010-04-22 | Cenomed Biosciences, Llc | Treatment of organophosphate exposure with ocinaplon |
| EP2376490B1 (en) * | 2008-12-04 | 2013-01-23 | Proximagen Limited | Imidazopyridine compounds |
| 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 |
| WO2012036278A1 (ja) * | 2010-09-17 | 2012-03-22 | 大正製薬株式会社 | グリシントランスポーター阻害物質 |
| CN108348510B (zh) | 2015-09-17 | 2022-01-04 | 圣母大学 | 针对分枝杆菌感染有用的含有苄胺的杂环化合物以及组合物 |
| 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 |
| US11497752B2 (en) | 2018-01-30 | 2022-11-15 | 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 |
| US12509453B2 (en) | 2019-01-29 | 2025-12-30 | Foghorn Therapeutics Inc. | BRM/BRG1 inhibitors and uses thereof |
| US12384776B2 (en) | 2019-01-29 | 2025-08-12 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| AU2021213811A1 (en) | 2020-01-29 | 2022-07-28 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| WO2021155264A1 (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 |
| US12606553B2 (en) | 2021-03-09 | 2026-04-21 | Foghorn Therapeutics Inc. | Crystalline forms, compositions containing same, and methods of their use |
| KR20260004434A (ko) * | 2023-04-24 | 2026-01-08 | 상하이 에스아이엠알 바이오테크놀로지 컴퍼니 리미티드 | 이미다조피리딘 또는 이미다조피라진 화합물, 이의 제조 방법, 약학 조성물 및 용도 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2568880B1 (fr) * | 1984-08-07 | 1986-12-12 | Synthelabo | Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
| FR2593818B1 (fr) * | 1986-02-05 | 1988-04-29 | Synthelabo | Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridine, leur preparation et leur application en therapeutique |
| ES2032455T3 (es) * | 1986-01-22 | 1993-02-16 | Synthelabo | Procedimiento para preparar derivados de 3-acilaminometil-imidazo (-1,2-a)piridinas. |
| FR2593181B1 (fr) * | 1986-01-22 | 1988-04-01 | Synthelabo | Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
| US20040204443A1 (en) * | 2003-01-27 | 2004-10-14 | Arthur Zaks | Method for inducing pain relief using imidazo[1,2-a]pyridine derivatives |
-
2005
- 2005-11-04 RU RU2007121864/04A patent/RU2007121864A/ru not_active Application Discontinuation
- 2005-11-04 AU AU2005303811A patent/AU2005303811A1/en not_active Abandoned
- 2005-11-04 DK DK05808135T patent/DK1814880T3/da active
- 2005-11-04 AT AT05808135T patent/ATE421962T1/de active
- 2005-11-04 ES ES05808135T patent/ES2321858T3/es not_active Expired - Lifetime
- 2005-11-04 KR KR1020077010318A patent/KR20070084026A/ko not_active Ceased
- 2005-11-04 PT PT05808135T patent/PT1814880E/pt unknown
- 2005-11-04 EP EP05808135A patent/EP1814880B1/en not_active Expired - Lifetime
- 2005-11-04 PL PL05808135T patent/PL1814880T3/pl unknown
- 2005-11-04 DE DE602005012598T patent/DE602005012598D1/de not_active Expired - Lifetime
- 2005-11-04 JP JP2007540634A patent/JP2008519805A/ja active Pending
- 2005-11-04 MX MX2007005611A patent/MX2007005611A/es active IP Right Grant
- 2005-11-04 US US11/667,494 patent/US20080200473A1/en not_active Abandoned
- 2005-11-04 WO PCT/EP2005/055753 patent/WO2006051063A1/en not_active Ceased
- 2005-11-04 BR BRPI0517796-0A patent/BRPI0517796A/pt not_active IP Right Cessation
- 2005-11-04 CN CN2005800386913A patent/CN101065377B/zh not_active Expired - Fee Related
- 2005-11-04 CA CA002585315A patent/CA2585315A1/en not_active Abandoned
- 2005-11-07 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
- 2005-11-10 UY UY29204A patent/UY29204A1/es not_active Application Discontinuation
-
2007
- 2007-05-03 IL IL182963A patent/IL182963A0/en unknown
- 2007-06-04 NO NO20072831A patent/NO20072831L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI357412B (en) | 2012-02-01 |
| UY29204A1 (es) | 2006-01-31 |
| PA8652101A1 (es) | 2006-10-13 |
| NO20072831L (no) | 2007-08-01 |
| CN101065377B (zh) | 2011-07-27 |
| US20080200473A1 (en) | 2008-08-21 |
| TW200624432A (en) | 2006-07-16 |
| RU2007121864A (ru) | 2008-12-20 |
| ATE421962T1 (de) | 2009-02-15 |
| JP2008519805A (ja) | 2008-06-12 |
| EP1814880A1 (en) | 2007-08-08 |
| CA2585315A1 (en) | 2006-05-18 |
| DK1814880T3 (da) | 2009-05-18 |
| PL1814880T3 (pl) | 2009-07-31 |
| CN101065377A (zh) | 2007-10-31 |
| EP1814880B1 (en) | 2009-01-28 |
| AR051626A1 (es) | 2007-01-24 |
| ES2321858T3 (es) | 2009-06-12 |
| IL182963A0 (en) | 2007-08-19 |
| WO2006051063A1 (en) | 2006-05-18 |
| PT1814880E (pt) | 2009-04-23 |
| PE20060967A1 (es) | 2006-09-20 |
| DE602005012598D1 (de) | 2009-03-19 |
| KR20070084026A (ko) | 2007-08-24 |
| BRPI0517796A (pt) | 2008-10-28 |
| MX2007005611A (es) | 2007-07-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2005303811A1 (en) | Imidazo(1,2-a)pyridine compounds, compositions, uses and methods related thereto | |
| RU2486188C2 (ru) | СОЕДИНЕНИЯ ИМИДАЗО-[1,2-b]-ПИРИДАЗИНА (ВАРИАНТЫ), СПОСОБ ПОЛУЧЕНИЯ СОЕДИНЕНИЙ ИМИДАЗО-[1,2-b]-ПИРИДАЗИНА (ВАРИАНТЫ), ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И ЛЕКАРСТВЕННОЕ СРЕДСТВО ДЛЯ ЛЕЧЕНИЯ И/ИЛИ ПРЕДУПРЕЖДЕНИЯ ЗАБОЛЕВАНИЙ, СВЯЗАННЫХ С ИНГИБИРОВАНИЕМ ГАМКА РЕЦЕПТОРОВ | |
| US7741332B2 (en) | Fused ring heterocycles as potassium channel modulators | |
| EP1732933B1 (en) | Compounds for treating dyslipidemia | |
| CN1812972B (zh) | 天冬氨酸特异性半胱氨酸蛋白酶抑制剂及其用途 | |
| US20040058930A1 (en) | Thiophene-based tricyclic compounds and pharmaceutical compositions comprising same | |
| SK4322003A3 (en) | Aza- and polyaza-naphthalenyl carboxamides useful as HIV integrase inhibitors | |
| WO2005042537A1 (en) | Phenyl-aniline substituted bicyclic compounds useful as kinase inhibitors | |
| KR20110031318A (ko) | Ｉａ 심부전 및 암 치료에 유용한 단백질 키나제 ｄ 억제제로서의 2,4'-비피리디닐 화합물 | |
| DE102006012251A1 (de) | Substituierte 4-Amino-chinazolin-Derivate und ihre Verwendung zur Herstellung von Arzneimitteln | |
| US8754101B2 (en) | N-cyclobutyl-imidazopyridine-methylamine as TRPV1 antagonists | |
| KR20080080212A (ko) | 바닐로이드 수용체 １ (ｖｒｌ) 억제제로서의 신규벤즈이미다졸 유도체 | |
| CN108697697A (zh) | 治疗及/或预防纤维性疾病的胺基萘醌化合物 | |
| JP2010500330A (ja) | Ｇａｂａａ受容体に対して親和性を有する１ｈ−キノリン−４−オン化合物、方法、使用及び組成物 | |
| EP1886996A1 (en) | 1H-Quinolin-4-one compounds, with affinity for the GABA receptor, processes, uses and compositions | |
| AU2006334364B2 (en) | Imidazo (1,2-a)pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof | |
| US20070043064A1 (en) | 7-Substituted 3-nitro-pyrazo[1,5-a] pyrimidines | |
| WO2006084835A1 (en) | N-(3-(imidazo [1,5-a]pyrimidin-4-yl)phenyl]-sulfonamides and n-[3-(imidazo[1,5-a]pyrimidin-4-yl)-phenyl]-carboxamides and their use as gabaa receptor modulators | |
| HK1123792B (en) | Imidazo (1,2-a)pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |