OA11378A - Method of synthesis of pyrrole amides. - Google Patents

Method of synthesis of pyrrole amides. Download PDF

Info

Publication number: OA11378A
Authority: OA; OAPI
Prior art keywords: oxo; phenyl; tetrahydro; methyl; acid
Prior art date: 1997-11-13

Application number

OA1200000136A

Other languages

English (en)

Inventor

Douglas John Meldrum Allen

David Jon Am Ende

Pamela Jane Clifford

Alyson Kay Conrad

Shane Allen Eisenbeis

Teresa Woodall Makowski

George Joseph Quallich

John Anthony Ragan

Gregory Randall Young

Original Assignee

Pfizer Prod Inc

Priority date (The priority date 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 date listed.)

1997-11-13

Filing date

2000-05-12

Publication date

2004-01-27

2000-05-12 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2004-01-27 Publication of OA11378A publication Critical patent/OA11378A/en

Links

238000000034 method Methods 0.000 title claims abstract description 51
-1 pyrrole amides Chemical class 0.000 title claims description 18
238000003786 synthesis reaction Methods 0.000 title description 5
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 4
230000015572 biosynthetic process Effects 0.000 title description 4
238000006243 chemical reaction Methods 0.000 claims abstract description 26
239000002253 acid Substances 0.000 claims abstract description 19
150000001875 compounds Chemical class 0.000 claims description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
YWUVOJJHVFLNJA-UHFFFAOYSA-N 2-fluoro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(F)=C1 YWUVOJJHVFLNJA-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
239000012442 inert solvent Substances 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
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
229920001774 Perfluoroether Polymers 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 5
BENJFDPHDCGUAQ-UHFFFAOYSA-N 1-benzofuran-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=COC2=C1 BENJFDPHDCGUAQ-UHFFFAOYSA-N 0.000 claims 1
241000490229 Eucephalus Species 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
239000007787 solid Substances 0.000 description 16
229960003692 gamma aminobutyric acid Drugs 0.000 description 13
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical class N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 9
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 9
238000001816 cooling Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
210000004556 brain Anatomy 0.000 description 5
DBOVMTXPZWVYAQ-UHFFFAOYSA-N cycloheptane-1,3-dione Chemical compound O=C1CCCCC(=O)C1 DBOVMTXPZWVYAQ-UHFFFAOYSA-N 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
239000000284 extract Substances 0.000 description 4
230000003993 interaction Effects 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
235000011149 sulphuric acid Nutrition 0.000 description 4
XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 3
UIBDRXZQWRSOKA-UHFFFAOYSA-N 2-(5-aminopyridin-2-yl)oxyethanol Chemical compound NC1=CC=C(OCCO)N=C1 UIBDRXZQWRSOKA-UHFFFAOYSA-N 0.000 description 3
IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 3
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 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
150000008065 acid anhydrides Chemical class 0.000 description 3
230000036506 anxiety Effects 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
235000019439 ethyl acetate Nutrition 0.000 description 3
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
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 description 3
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 description 3
230000001242 postsynaptic effect Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000004044 response Effects 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
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
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical class NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-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
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 2
NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 2
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-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
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 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
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
239000012043 crude product Substances 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
230000002708 enhancing effect Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
230000005764 inhibitory process Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 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
230000007958 sleep Effects 0.000 description 2
239000002002 slurry Substances 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
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 2
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 description 2
239000011701 zinc Substances 0.000 description 2
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
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 1
DBGSRZSKGVSXRK-UHFFFAOYSA-N 1-[2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]acetyl]-3,6-dihydro-2H-pyridine-4-carboxylic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CCC(=CC1)C(=O)O DBGSRZSKGVSXRK-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 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
OZMCIZDEFIDDJW-UHFFFAOYSA-N 3,3-dichlorocyclobutan-1-one Chemical compound ClC1(CC(C1)=O)Cl OZMCIZDEFIDDJW-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
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 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
NQFGFSBJMVZWAE-UHFFFAOYSA-N 4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxylic acid Chemical compound C1CCCC(=O)C2=C1NC=C2C(=O)O NQFGFSBJMVZWAE-UHFFFAOYSA-N 0.000 description 1
AAMWMZBIMBWXPQ-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-cyclohepta[b]furan-3-carboxylic acid Chemical compound C1CCCCC2=C1OC=C2C(=O)O AAMWMZBIMBWXPQ-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
FMZCWRYXPHDICO-UHFFFAOYSA-N 6,7-dimethoxy-n-(3-methoxyphenyl)quinazolin-4-amine Chemical compound COC1=CC=CC(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 FMZCWRYXPHDICO-UHFFFAOYSA-N 0.000 description 1
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 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
229920006063 Lamide® Polymers 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
230000036626 alertness Effects 0.000 description 1
230000004075 alteration Effects 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
229940005530 anxiolytics Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000006399 behavior Effects 0.000 description 1
238000009227 behaviour therapy Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
230000019771 cognition Effects 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
238000007865 diluting Methods 0.000 description 1
BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229960004979 fampridine Drugs 0.000 description 1
239000012467 final product Substances 0.000 description 1
229960003528 flurazepam Drugs 0.000 description 1
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
239000011521 glass Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
230000002102 hyperpolarization Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
210000005171 mammalian brain Anatomy 0.000 description 1
238000004949 mass spectrometry Methods 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
OVIGGAOMLUKHDD-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 OVIGGAOMLUKHDD-UHFFFAOYSA-N 0.000 description 1
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 1
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 description 1
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 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
210000001640 nerve ending Anatomy 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating 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
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000004799 sedative–hypnotic effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000000273 spinal nerve root Anatomy 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 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
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
LPXIOYIHXNPBCQ-UHFFFAOYSA-N tert-butyl n-benzyl-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=CC=C1 LPXIOYIHXNPBCQ-UHFFFAOYSA-N 0.000 description 1
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
229960003386 triazolam Drugs 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
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 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)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole 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)

OA1200000136A 1997-11-13 2000-05-12 Method of synthesis of pyrrole amides. OA11378A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US6542297P	1997-11-13	1997-11-13
US7426698P	1998-02-10	1998-02-10

Publications (1)

Publication Number	Publication Date
OA11378A true OA11378A (en)	2004-01-27

Family

ID=26745584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000136A OA11378A (en)	1997-11-13	2000-05-12	Method of synthesis of pyrrole amides.

Country Status (35)

Country	Link
US (1)	US6262272B1 (id)
EP (1)	EP1030838B1 (id)
JP (1)	JP3497469B2 (id)
KR (1)	KR100386722B1 (id)
CN (2)	CN1508129A (id)
AT (1)	ATE231492T1 (id)
AU (1)	AU745788B2 (id)
BG (1)	BG64530B1 (id)
BR (1)	BR9814161A (id)
CA (1)	CA2310095A1 (id)
CZ (1)	CZ20001769A3 (id)
DE (1)	DE69810959T2 (id)
DK (1)	DK1030838T3 (id)
DZ (1)	DZ2651A1 (id)
EA (1)	EA002243B1 (id)
ES (1)	ES2186232T3 (id)
HR (1)	HRP20000298A2 (id)
HU (1)	HUP0100235A3 (id)
ID (1)	ID24135A (id)
IL (1)	IL135710A0 (id)
IS (1)	IS5469A (id)
MA (1)	MA24697A1 (id)
NO (1)	NO20002214L (id)
NZ (1)	NZ503916A (id)
OA (1)	OA11378A (id)
PA (1)	PA8462901A1 (id)
PL (1)	PL340554A1 (id)
PT (1)	PT1030838E (id)
SK (1)	SK6872000A3 (id)
TN (1)	TNSN98204A1 (id)
TR (1)	TR200001343T2 (id)
TW (1)	TW509675B (id)
UY (1)	UY25249A1 (id)
WO (1)	WO1999025684A1 (id)
YU (1)	YU27300A (id)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HUP0202534A3 (en) *	1999-08-31	2002-12-28	Neurogen Corp Branford	Fused pyrrolecarboxamides: gaba brain receptor ligands and pharmaceutical compositions containing them
WO2002020492A1 (en) *	2000-09-06	2002-03-14	Neurogen Corporation	Aryl substituted tetrahydroindazoles and their use as ligands for the gaba-a receptor
BR0115874A (pt) *	2000-12-04	2003-10-28	Pfizer Prod Inc	Sìntese de pirrole-amidas
AU2003212979A1 (en)	2002-02-07	2003-09-02	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
EP3097095A1 (en) *	2014-01-24	2016-11-30	AbbVie Inc.	Furo-3-carboxamide derivatives and methods of use

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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
WO1997034870A1 (en)	1996-03-22	1997-09-25	Neurogen Corporation	Certain fused pyrrolecarboxamides as gaba brain receptor ligands

1998
- 1998-10-21 CN CNA031594727A patent/CN1508129A/zh active Pending
- 1998-10-21 EA EA200000413A patent/EA002243B1/ru not_active IP Right Cessation
- 1998-10-21 WO PCT/IB1998/001672 patent/WO1999025684A1/en not_active Ceased
- 1998-10-21 EP EP98946678A patent/EP1030838B1/en not_active Expired - Lifetime
- 1998-10-21 US US09/403,985 patent/US6262272B1/en not_active Expired - Fee Related
- 1998-10-21 DK DK98946678T patent/DK1030838T3/da active
- 1998-10-21 KR KR10-2000-7005185A patent/KR100386722B1/ko not_active Expired - Fee Related
- 1998-10-21 CA CA002310095A patent/CA2310095A1/en not_active Abandoned
- 1998-10-21 AT AT98946678T patent/ATE231492T1/de not_active IP Right Cessation
- 1998-10-21 ES ES98946678T patent/ES2186232T3/es not_active Expired - Lifetime
- 1998-10-21 JP JP2000521068A patent/JP3497469B2/ja not_active Expired - Fee Related
- 1998-10-21 CZ CZ20001769A patent/CZ20001769A3/cs unknown
- 1998-10-21 TR TR2000/01343T patent/TR200001343T2/xx unknown
- 1998-10-21 ID IDW20000893A patent/ID24135A/id unknown
- 1998-10-21 PT PT98946678T patent/PT1030838E/pt unknown
- 1998-10-21 HR HR20000298A patent/HRP20000298A2/hr not_active Application Discontinuation
- 1998-10-21 CN CN98811119A patent/CN1280566A/zh active Pending
- 1998-10-21 AU AU93639/98A patent/AU745788B2/en not_active Ceased
- 1998-10-21 SK SK687-2000A patent/SK6872000A3/sk unknown
- 1998-10-21 NZ NZ503916A patent/NZ503916A/xx unknown
- 1998-10-21 HU HU0100235A patent/HUP0100235A3/hu unknown
- 1998-10-21 IL IL13571098A patent/IL135710A0/xx unknown
- 1998-10-21 YU YU27300A patent/YU27300A/sh unknown
- 1998-10-21 DE DE69810959T patent/DE69810959T2/de not_active Expired - Fee Related
- 1998-10-21 PL PL98340554A patent/PL340554A1/xx not_active Application Discontinuation
- 1998-10-21 BR BR9814161-9A patent/BR9814161A/pt not_active Application Discontinuation
- 1998-11-10 PA PA19988462901A patent/PA8462901A1/es unknown
- 1998-11-10 TW TW087118708A patent/TW509675B/zh not_active IP Right Cessation
- 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 OA OA1200000136A patent/OA11378A/en unknown

Also Published As

Publication number	Publication date
CA2310095A1 (en)	1999-05-27
WO1999025684A1 (en)	1999-05-27
CN1508129A (zh)	2004-06-30
AU745788B2 (en)	2002-03-28
CN1280566A (zh)	2001-01-17
NZ503916A (en)	2002-08-28
DZ2651A1 (fr)	2003-03-15
EA200000413A1 (ru)	2000-12-25
HRP20000298A2 (en)	2001-02-28
EP1030838B1 (en)	2003-01-22
IL135710A0 (en)	2001-05-20
JP2001523660A (ja)	2001-11-27
EA002243B1 (ru)	2002-02-28
YU27300A (sh)	2002-10-18
ID24135A (id)	2000-07-06
ES2186232T3 (es)	2003-05-01
BR9814161A (pt)	2000-09-26
PL340554A1 (en)	2001-02-12
TNSN98204A1 (fr)	2005-03-15
US6262272B1 (en)	2001-07-17
BG64530B1 (bg)	2005-06-30
DE69810959T2 (de)	2003-06-05
TW509675B (en)	2002-11-11
DK1030838T3 (da)	2003-02-24
NO20002214D0 (no)	2000-04-28
KR20010032063A (ko)	2001-04-16
UY25249A1 (es)	1999-07-19
PA8462901A1 (es)	2000-05-24
TR200001343T2 (tr)	2001-02-21
JP3497469B2 (ja)	2004-02-16
IS5469A (is)	2000-04-26
CZ20001769A3 (cs)	2001-09-12
HUP0100235A3 (en)	2002-04-29
EP1030838A1 (en)	2000-08-30
MA24697A1 (fr)	1999-07-01
DE69810959D1 (de)	2003-02-27
NO20002214L (no)	2000-05-12
PT1030838E (pt)	2003-03-31
BG104413A (en)	2001-02-28
ATE231492T1 (de)	2003-02-15
SK6872000A3 (en)	2002-02-05
KR100386722B1 (ko)	2003-06-09
HUP0100235A2 (hu)	2001-12-28
AU9363998A (en)	1999-06-07

Publication	Publication Date	Title
CA2243317C (en)	2007-09-25	Novel fused pyrrolecarboxamides; a new class of gaba brain receptor ligands
US5750702A (en)	1998-05-12	Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain receptor ligands
EP0725775B1 (en)	1998-07-22	Certain fused pyrrolecarboxanilides; a new class of gaba brain receptor ligands
US6096887A (en)	2000-08-01	Certain fused pyrrolecarboxamides; a new class of GABA brain receptor ligands
WO1997034870A1 (en)	1997-09-25	Certain fused pyrrolecarboxamides as gaba brain receptor ligands
US6211365B1 (en)	2001-04-03	Fused pyrrolecarboxamides; a new class of GABA brain receptor ligands
KR100632188B1 (ko)	2007-04-25	신규한피페라진및피페리딘화합물
EP1030838B1 (en)	2003-01-22	Method of synthesis of pyrrole amides
Khan et al.	2011	Sequential three-component reactions: synthesis, regioselectivity and application of functionalized dihydropyridines (DHPs) for the creation of fused naphthyridines
Li et al.	2017	Regioselective 1, 2-addition of allenamides with N-haloimides: synthesis of 2-halo allylic aminal derivatives
WO2021246781A1 (en)	2021-12-09	Pyridine derivatives as immunomodulators
AP948A (en)	2001-03-15	Method of synthesis of pyrrole amides.
MXPA00004662A (en)	2002-06-05	Method of synthesis of pyrrole amides
HK1032963A (en)	2001-08-10	Method of synthesis of pyrrole amides
FR2758326A1 (fr)	1998-07-17	Derives de pyridone, leur prepaparation et leur utilisation comme intermediaires de synthese
US5272170A (en)	1993-12-21	Tetralones with pharmacological activity
AU729634B2 (en)	2001-02-08	Certain fused pyrrolecarboxanilides: A new class of GABA brain receptor ligands
JP2004515491A (ja)	2004-05-27	縮合ピロールカルボキサミド類の合成