HRP20000298A2 - Method of synthesis of pyrrole amides - Google Patents
Method of synthesis of pyrrole amides Download PDFInfo
- Publication number
- HRP20000298A2 HRP20000298A2 HR20000298A HRP20000298A HRP20000298A2 HR P20000298 A2 HRP20000298 A2 HR P20000298A2 HR 20000298 A HR20000298 A HR 20000298A HR P20000298 A HRP20000298 A HR P20000298A HR P20000298 A2 HRP20000298 A2 HR P20000298A2
- Authority
- HR
- Croatia
- Prior art keywords
- oxo
- tetrahydro
- phenyl
- carboxylic acid
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 51
- -1 pyrrole amides Chemical class 0.000 title claims description 17
- 238000003786 synthesis reaction Methods 0.000 title description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 3
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 51
- 230000008569 process Effects 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- YWUVOJJHVFLNJA-UHFFFAOYSA-N 2-fluoro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(F)=C1 YWUVOJJHVFLNJA-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 7
- PXIYUIZGOHSVAZ-UHFFFAOYSA-N 4-oxo-5,6,7,8-tetrahydrocyclohepta[b]furan-3-carboxylic acid Chemical compound C1CCCC(=O)C2=C1OC=C2C(=O)O PXIYUIZGOHSVAZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- QOBQEJNQDPECSX-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydrocyclohepta[b]furan-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=COC2=C1C(=O)CCCC2 QOBQEJNQDPECSX-UHFFFAOYSA-N 0.000 claims description 4
- PIGOARSPVCMJLE-UHFFFAOYSA-N n-(4-fluorophenyl)-6-methyl-4-oxo-6,7-dihydro-5h-1-benzofuran-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2OC=C1C(=O)NC1=CC=C(F)C=C1 PIGOARSPVCMJLE-UHFFFAOYSA-N 0.000 claims description 4
- KJGYWEJKSSJUSP-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydrocyclohepta[b]furan-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=COC2=C1C(=O)CCCC2 KJGYWEJKSSJUSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- JUMUBLTUERLNEA-UHFFFAOYSA-N tert-butyl n-methyl-n-[[4-[(4-oxo-1,5,6,7-tetrahydroindole-3-carbonyl)amino]phenyl]methyl]carbamate Chemical group C1=CC(CN(C)C(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 JUMUBLTUERLNEA-UHFFFAOYSA-N 0.000 claims description 4
- CCMONXZKHDLRCG-UHFFFAOYSA-N tert-butyl n-methyl-n-[[4-[(4-oxo-6,7-dihydro-5h-1-benzofuran-3-carbonyl)amino]phenyl]methyl]carbamate Chemical compound C1=CC(CN(C)C(=O)OC(C)(C)C)=CC=C1NC(=O)C1=COC2=C1C(=O)CCC2 CCMONXZKHDLRCG-UHFFFAOYSA-N 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- XTEUAERJBDGJFG-UHFFFAOYSA-N 6-methyl-4-oxo-n-pyridin-3-yl-6,7-dihydro-5h-1-benzofuran-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2OC=C1C(=O)NC1=CC=CN=C1 XTEUAERJBDGJFG-UHFFFAOYSA-N 0.000 claims description 3
- VICWUUFRUVSNPZ-UHFFFAOYSA-N 6-methyl-4-oxo-n-pyridin-4-yl-6,7-dihydro-5h-1-benzofuran-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2OC=C1C(=O)NC1=CC=NC=C1 VICWUUFRUVSNPZ-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical group CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- FNMUCXOGLHZEOY-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-4-oxo-5,6,7,8-tetrahydrocyclohepta[b]furan-3-carboxamide Chemical compound C1CCCC(=O)C2=C1OC=C2C(=O)NC1=CC=C(OCO2)C2=C1 FNMUCXOGLHZEOY-UHFFFAOYSA-N 0.000 claims description 3
- SLCCSZXAZOXSBS-UHFFFAOYSA-N n-(4-ethoxyphenyl)-4-oxo-5,6-dihydrocyclopenta[b]furan-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=COC2=C1C(=O)CC2 SLCCSZXAZOXSBS-UHFFFAOYSA-N 0.000 claims description 3
- XJRXYKLAEPFXGF-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)pyridin-3-yl]-6-methyl-4-oxo-6,7-dihydro-5h-1-benzofuran-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2OC=C1C(=O)NC1=CC=C(OCCO)N=C1 XJRXYKLAEPFXGF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 229920001774 Perfluoroether Polymers 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 102000027484 GABAA receptors Human genes 0.000 abstract description 4
- 108091008681 GABAA receptors Proteins 0.000 abstract description 4
- NHNHWBFFDARHFO-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetamide Chemical class NC(=O)CC1=CC=CN1 NHNHWBFFDARHFO-UHFFFAOYSA-N 0.000 abstract 1
- RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- 239000000243 solution Substances 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 15
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229940049706 benzodiazepine Drugs 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 150000001557 benzodiazepines Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LTSBKYGKJDMJNJ-UHFFFAOYSA-N 6-methyl-4-oxo-6,7-dihydro-5h-1-benzofuran-3-carboxylic acid Chemical compound O=C1CC(C)CC2=C1C(C(O)=O)=CO2 LTSBKYGKJDMJNJ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- DBOVMTXPZWVYAQ-UHFFFAOYSA-N cycloheptane-1,3-dione Chemical compound O=C1CCCCC(=O)C1 DBOVMTXPZWVYAQ-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 3
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical class NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 description 3
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 3
- OZMCIZDEFIDDJW-UHFFFAOYSA-N 3,3-dichlorocyclobutan-1-one Chemical compound ClC1(CC(C1)=O)Cl OZMCIZDEFIDDJW-UHFFFAOYSA-N 0.000 description 3
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 3
- QQPMDRGNNFKVEL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzofuran-3-carboxylic acid Chemical compound C1CCCC2=C1OC=C2C(=O)O QQPMDRGNNFKVEL-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 229960003529 diazepam Drugs 0.000 description 3
- 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 3
- 230000000694 effects Effects 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000001242 postsynaptic effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- ZXZZEBPOSRKQAU-UHFFFAOYSA-N tert-butyl n-[(4-aminophenyl)methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=C(N)C=C1 ZXZZEBPOSRKQAU-UHFFFAOYSA-N 0.000 description 3
- QKSNGDCSRYEOCH-UHFFFAOYSA-N tert-butyl n-methyl-n-[(4-nitrophenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=C([N+]([O-])=O)C=C1 QKSNGDCSRYEOCH-UHFFFAOYSA-N 0.000 description 3
- WGVPUAKFQLQUKW-UHFFFAOYSA-N 1-(2-fluoro-4-iodophenyl)-2,5-dimethylpyrrole Chemical compound CC1=CC=C(C)N1C1=CC=C(I)C=C1F WGVPUAKFQLQUKW-UHFFFAOYSA-N 0.000 description 2
- IJLHORUAMUWLHR-UHFFFAOYSA-N 1-(2-fluoro-4-methoxyphenyl)-2,5-dimethylpyrrole Chemical compound FC1=CC(OC)=CC=C1N1C(C)=CC=C1C IJLHORUAMUWLHR-UHFFFAOYSA-N 0.000 description 2
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 2
- MIOVLJHOMINVHH-UHFFFAOYSA-N 4-oxo-5,6-dihydrocyclopenta[b]furan-3-carboxylic acid Chemical compound C1CC(=O)C2=C1OC=C2C(=O)O MIOVLJHOMINVHH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 2
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 description 2
- 210000005171 mammalian brain Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YRWDLPYCYUHYAW-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-6,6-dimethyl-4-oxo-5,7-dihydro-1-benzofuran-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=COC2=C1C(=O)CC(C)(C)C2 YRWDLPYCYUHYAW-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- UIBDRXZQWRSOKA-UHFFFAOYSA-N 2-(5-aminopyridin-2-yl)oxyethanol Chemical compound NC1=CC=C(OCCO)N=C1 UIBDRXZQWRSOKA-UHFFFAOYSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- CUMTUBVTKOYYOU-UHFFFAOYSA-N 2-fluoro-4-iodoaniline Chemical compound NC1=CC=C(I)C=C1F CUMTUBVTKOYYOU-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- IOPXFUALWUTZQK-UHFFFAOYSA-N 4-oxo-1,5,6,7-tetrahydroindole-3-carboxylic acid Chemical compound C1CCC(=O)C2=C1NC=C2C(=O)O IOPXFUALWUTZQK-UHFFFAOYSA-N 0.000 description 1
- DMIIMPQQPXUKOO-UHFFFAOYSA-N 5-methylcyclohexane-1,3-dione Chemical compound CC1CC(=O)CC(=O)C1 DMIIMPQQPXUKOO-UHFFFAOYSA-N 0.000 description 1
- IAKDSPOTXLPECE-UHFFFAOYSA-N 6,6-dichloro-5-trimethylsilyloxybicyclo[3.2.0]heptan-7-one Chemical compound C1CCC2C(=O)C(Cl)(Cl)C21O[Si](C)(C)C IAKDSPOTXLPECE-UHFFFAOYSA-N 0.000 description 1
- KOXFZRZSHOMWOM-UHFFFAOYSA-N 6,6-dimethyl-4-oxo-5,7-dihydro-1-benzofuran-3-carboxylic acid Chemical compound O=C1CC(C)(C)CC2=C1C(C(O)=O)=CO2 KOXFZRZSHOMWOM-UHFFFAOYSA-N 0.000 description 1
- DZMHAFCHNMQQCU-UHFFFAOYSA-N 6-methyl-4-oxo-n-pyridin-3-yl-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2NC=C1C(=O)NC1=CC=CN=C1 DZMHAFCHNMQQCU-UHFFFAOYSA-N 0.000 description 1
- DNZMQVVRWFULNH-UHFFFAOYSA-N 6-methyl-4-oxo-n-pyridin-4-yl-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2NC=C1C(=O)NC1=CC=NC=C1 DNZMQVVRWFULNH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 230000009508 GABAergic inhibition Effects 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
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- 239000012230 colorless oil Substances 0.000 description 1
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- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- UBMYYGXGMPGCBO-UHFFFAOYSA-N cyclopenten-1-yloxy(trimethyl)silane Chemical compound C[Si](C)(C)OC1=CCCC1 UBMYYGXGMPGCBO-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
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- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
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- SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 description 1
- 229960003528 flurazepam Drugs 0.000 description 1
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- 238000000338 in vitro Methods 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- JLKRJHPQNYVSGM-UHFFFAOYSA-N methyl-(4-nitro-benzyl)-amine Chemical compound CNCC1=CC=C([N+]([O-])=O)C=C1 JLKRJHPQNYVSGM-UHFFFAOYSA-N 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- XCKULDMPCDTBJK-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C1CCCC(=O)C2=C1NC=C2C(=O)NC1=CC=C(OCO2)C2=C1 XCKULDMPCDTBJK-UHFFFAOYSA-N 0.000 description 1
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- MYRXFTOTOOZDPW-UHFFFAOYSA-N n-(4-ethoxyphenyl)-4-oxo-5,6-dihydro-1h-cyclopenta[b]pyrrole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CC2 MYRXFTOTOOZDPW-UHFFFAOYSA-N 0.000 description 1
- BBUGZFUOHBBWKT-UHFFFAOYSA-N n-(4-fluorophenyl)-6-methyl-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2NC=C1C(=O)NC1=CC=C(F)C=C1 BBUGZFUOHBBWKT-UHFFFAOYSA-N 0.000 description 1
- QWZRQJOPLWQECM-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 QWZRQJOPLWQECM-UHFFFAOYSA-N 0.000 description 1
- XFJIYNUISLDNLP-UHFFFAOYSA-N n-[4-(methylaminomethyl)phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(CNC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 XFJIYNUISLDNLP-UHFFFAOYSA-N 0.000 description 1
- ZVHQSPKABFGHTC-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)pyridin-3-yl]-6-methyl-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2NC=C1C(=O)NC1=CC=C(OCCO)N=C1 ZVHQSPKABFGHTC-UHFFFAOYSA-N 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
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- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
- 229960003386 triazolam Drugs 0.000 description 1
- 238000005406 washing 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Tea And Coffee (AREA)
- Fats And Perfumes (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6542297P | 1997-11-13 | 1997-11-13 | |
| US7426698P | 1998-02-10 | 1998-02-10 | |
| PCT/IB1998/001672 WO1999025684A1 (en) | 1997-11-13 | 1998-10-21 | Method of synthesis of pyrrole amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20000298A2 true HRP20000298A2 (en) | 2001-02-28 |
Family
ID=26745584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20000298A HRP20000298A2 (en) | 1997-11-13 | 2000-05-12 | Method of synthesis of pyrrole amides |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6262272B1 (de) |
| EP (1) | EP1030838B1 (de) |
| JP (1) | JP3497469B2 (de) |
| KR (1) | KR100386722B1 (de) |
| CN (2) | CN1280566A (de) |
| AT (1) | ATE231492T1 (de) |
| AU (1) | AU745788B2 (de) |
| BG (1) | BG64530B1 (de) |
| BR (1) | BR9814161A (de) |
| CA (1) | CA2310095A1 (de) |
| CZ (1) | CZ20001769A3 (de) |
| DE (1) | DE69810959T2 (de) |
| DK (1) | DK1030838T3 (de) |
| DZ (1) | DZ2651A1 (de) |
| EA (1) | EA002243B1 (de) |
| ES (1) | ES2186232T3 (de) |
| HR (1) | HRP20000298A2 (de) |
| HU (1) | HUP0100235A3 (de) |
| ID (1) | ID24135A (de) |
| IL (1) | IL135710A0 (de) |
| IS (1) | IS5469A (de) |
| MA (1) | MA24697A1 (de) |
| NO (1) | NO20002214L (de) |
| NZ (1) | NZ503916A (de) |
| OA (1) | OA11378A (de) |
| PA (1) | PA8462901A1 (de) |
| PL (1) | PL340554A1 (de) |
| PT (1) | PT1030838E (de) |
| SK (1) | SK6872000A3 (de) |
| TN (1) | TNSN98204A1 (de) |
| TR (1) | TR200001343T2 (de) |
| TW (1) | TW509675B (de) |
| UY (1) | UY25249A1 (de) |
| WO (1) | WO1999025684A1 (de) |
| YU (1) | YU27300A (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA12015A (en) | 1999-08-31 | 2006-04-19 | Neurogen Corp | Fused pyrrolecarboxamides: gaba brain receptor ligands. |
| EP1315703A1 (de) * | 2000-09-06 | 2003-06-04 | Neurogen Corporation | Aryl-substituierte tetrahydroindazole-derivate und ihre verwendung als liganden für gaba-a receptoren |
| CA2430841A1 (en) * | 2000-12-04 | 2002-06-13 | Pfizer Products Inc. | Synthesis of fused pyrrolecarboxamides |
| WO2003066634A1 (en) | 2002-02-07 | 2003-08-14 | Neurogen Corporation | Substituted fused pyrazolecarboxylic acid arylamides and related compounds |
| US20080153629A1 (en) * | 2004-05-07 | 2008-06-26 | Sullivan Michael J | Thick Outer Cover Layer Golf Ball |
| CN102786458B (zh) * | 2012-06-04 | 2014-02-12 | 天津渤海职业技术学院 | 吡咯甲酰胺衍生物、其制备方法和用途 |
| MX2016009621A (es) * | 2014-01-24 | 2016-11-17 | Abbvie Inc | Derivados de fur0-3-carboxamida y metodos de uso. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750702A (en) | 1993-10-27 | 1998-05-12 | Neurogen Corporation | Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain receptor ligands |
| US5484944A (en) | 1993-10-27 | 1996-01-16 | Neurogen Corporation | Certain fused pyrrolecarboxanilides and their use as GABA brain receptor ligands |
| US5804686A (en) | 1996-01-19 | 1998-09-08 | Neurogen Corporation | fused pyrrolecarboxamides; a new class of GABA brain receptor ligands |
| EP0888300A1 (de) | 1996-03-22 | 1999-01-07 | Neurogen Corporation | Kondensierte pyrrolcarboxamide als gaba-gehirn-rezeptor-liganden |
-
1998
- 1998-10-21 ID IDW20000893A patent/ID24135A/id unknown
- 1998-10-21 IL IL13571098A patent/IL135710A0/xx unknown
- 1998-10-21 AU AU93639/98A patent/AU745788B2/en not_active Ceased
- 1998-10-21 JP JP2000521068A patent/JP3497469B2/ja not_active Expired - Fee Related
- 1998-10-21 BR BR9814161-9A patent/BR9814161A/pt not_active Application Discontinuation
- 1998-10-21 NZ NZ503916A patent/NZ503916A/xx unknown
- 1998-10-21 TR TR2000/01343T patent/TR200001343T2/xx unknown
- 1998-10-21 CN CN98811119A patent/CN1280566A/zh active Pending
- 1998-10-21 EA EA200000413A patent/EA002243B1/ru not_active IP Right Cessation
- 1998-10-21 CA CA002310095A patent/CA2310095A1/en not_active Abandoned
- 1998-10-21 EP EP98946678A patent/EP1030838B1/de not_active Expired - Lifetime
- 1998-10-21 HU HU0100235A patent/HUP0100235A3/hu unknown
- 1998-10-21 PL PL98340554A patent/PL340554A1/xx not_active Application Discontinuation
- 1998-10-21 CZ CZ20001769A patent/CZ20001769A3/cs unknown
- 1998-10-21 CN CNA031594727A patent/CN1508129A/zh active Pending
- 1998-10-21 PT PT98946678T patent/PT1030838E/pt unknown
- 1998-10-21 ES ES98946678T patent/ES2186232T3/es not_active Expired - Lifetime
- 1998-10-21 DE DE69810959T patent/DE69810959T2/de not_active Expired - Fee Related
- 1998-10-21 SK SK687-2000A patent/SK6872000A3/sk unknown
- 1998-10-21 US US09/403,985 patent/US6262272B1/en not_active Expired - Fee Related
- 1998-10-21 WO PCT/IB1998/001672 patent/WO1999025684A1/en not_active Application Discontinuation
- 1998-10-21 YU YU27300A patent/YU27300A/sh unknown
- 1998-10-21 AT AT98946678T patent/ATE231492T1/de not_active IP Right Cessation
- 1998-10-21 DK DK98946678T patent/DK1030838T3/da active
- 1998-10-21 KR KR10-2000-7005185A patent/KR100386722B1/ko not_active IP Right Cessation
- 1998-11-10 TW TW087118708A patent/TW509675B/zh not_active IP Right Cessation
- 1998-11-10 PA PA19988462901A patent/PA8462901A1/es unknown
- 1998-11-11 DZ DZ980261A patent/DZ2651A1/xx active
- 1998-11-11 MA MA25342A patent/MA24697A1/fr unknown
- 1998-11-11 TN TNTNSN98204A patent/TNSN98204A1/fr unknown
- 1998-11-13 UY UY25249A patent/UY25249A1/es not_active IP Right Cessation
-
2000
- 2000-04-26 IS IS5469A patent/IS5469A/is unknown
- 2000-04-28 NO NO20002214A patent/NO20002214L/no unknown
- 2000-05-09 BG BG104413A patent/BG64530B1/bg unknown
- 2000-05-12 HR HR20000298A patent/HRP20000298A2/hr not_active Application Discontinuation
- 2000-05-12 OA OA1200000136A patent/OA11378A/en unknown
Also Published As
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| EP0725775B1 (de) | Kondensierte pyrrolcarboxanilide; eine neue klasse von gaba-gehirn-rezeptor-liganden | |
| US5804686A (en) | fused pyrrolecarboxamides; a new class of GABA brain receptor ligands | |
| US5750702A (en) | Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain receptor ligands | |
| US6096887A (en) | Certain fused pyrrolecarboxamides; a new class of GABA brain receptor ligands | |
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