SK11672003A3 - Imidazopyrimidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Imidazopyrimidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK11672003A3
Authority: SK; Slovakia
Prior art keywords: fluoro; imidazo; pyrimidin; phenyl; carbonitrile
Prior art date: 2001-03-21

Application number

SK1167-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Mark Stuart Chambers

Simon Charles Goodacre

David James Hallett

Andrew Jennings

Philip Jones

Richard Thomas Lewis

Kevin William Moore

Leslie Joseph Street

Helen Jane Szekeres

Original Assignee

Merck Sharp & Dohme Limited

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.)

2001-03-21

Filing date

2002-03-19

Publication date

2004-05-04

2001-03-21 Priority claimed from GB0107134A external-priority patent/GB0107134D0/en

2001-11-21 Priority claimed from GB0127938A external-priority patent/GB0127938D0/en

2002-03-19 Application filed by Merck Sharp & Dohme Limited filed Critical Merck Sharp & Dohme Limited

2004-05-04 Publication of SK11672003A3 publication Critical patent/SK11672003A3/sk

Links

150000005237 imidazopyrimidines Chemical class 0.000 title claims description 17
239000003446 ligand Substances 0.000 title abstract description 11
102000005915 GABA Receptors Human genes 0.000 title 1
108010005551 GABA Receptors Proteins 0.000 title 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 74
125000000217 alkyl group Chemical group 0.000 claims abstract description 41
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 17
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 16
125000005843 halogen group Chemical group 0.000 claims abstract description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
230000002265 prevention Effects 0.000 claims abstract description 3
230000002411 adverse Effects 0.000 claims abstract 2
-1 4-Fluoro-3- (pyridin-3-yl) phenyl Chemical group 0.000 claims description 218
150000001875 compounds Chemical class 0.000 claims description 151
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 54
229910052739 hydrogen Inorganic materials 0.000 claims description 43
238000000034 method Methods 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 33
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
239000003054 catalyst Substances 0.000 claims description 15
229910052723 transition metal Inorganic materials 0.000 claims description 15
150000003624 transition metals Chemical class 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 6
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
IGOYEQZQMOKVHA-UHFFFAOYSA-N 2-[3-(2-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1F)=CC=CC=1C1=CC=CN=C1 IGOYEQZQMOKVHA-UHFFFAOYSA-N 0.000 claims description 5
BKIXSCDBYYIHQI-UHFFFAOYSA-N 2-[3-(4-fluoro-3-pyridin-4-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=NC=C1 BKIXSCDBYYIHQI-UHFFFAOYSA-N 0.000 claims description 5
BJYFIXNUQKPNCK-UHFFFAOYSA-N 3-(2,4-difluoro-3-pyridin-3-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C(F)=C1C1=CC=CN=C1 BJYFIXNUQKPNCK-UHFFFAOYSA-N 0.000 claims description 5
OMYZTYAICBLVAX-UHFFFAOYSA-N 3-(2-fluoro-3-pyridin-3-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=CC=C1C1=CC=CN=C1 OMYZTYAICBLVAX-UHFFFAOYSA-N 0.000 claims description 5
IQLZXVPYLRIUKG-UHFFFAOYSA-N 3-(4-fluoro-3-pyridin-2-ylphenyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC=NC3=NC=2)C=C1C1=CC=CC=N1 IQLZXVPYLRIUKG-UHFFFAOYSA-N 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 4
CFJBAJFHHSRCFQ-UHFFFAOYSA-N 2-[3-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]propane-1,2-diol Chemical compound C=1N=C2N=C(C(O)(CO)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=C1 CFJBAJFHHSRCFQ-UHFFFAOYSA-N 0.000 claims description 4
QYZNDUWFJOQGKB-UHFFFAOYSA-N 3-(2,4-difluoro-3-pyridin-4-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C(F)=C1C1=CC=NC=C1 QYZNDUWFJOQGKB-UHFFFAOYSA-N 0.000 claims description 4
SJOGDTSVCJDKRA-UHFFFAOYSA-N 3-(2-fluoro-3-pyridin-4-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=CC=C1C1=CC=NC=C1 SJOGDTSVCJDKRA-UHFFFAOYSA-N 0.000 claims description 4
VWTKQROFEZYHOH-UHFFFAOYSA-N 3-(4-fluoro-3-pyridin-2-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=CC=N1 VWTKQROFEZYHOH-UHFFFAOYSA-N 0.000 claims description 4
RAKFIPTULFPLAH-UHFFFAOYSA-N 3-(4-fluoro-3-pyridin-4-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=NC=C1 RAKFIPTULFPLAH-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
SDMSHEWPIYMZHW-UHFFFAOYSA-N 2-[2-fluoro-5-(7-pyridin-2-ylimidazo[1,2-a]pyrimidin-3-yl)phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C=2N=CC=CC=2)C=C1C1=CC=CC=C1C#N SDMSHEWPIYMZHW-UHFFFAOYSA-N 0.000 claims description 3
KDYOOVVMOGCFJJ-UHFFFAOYSA-N 2-[2-fluoro-5-[7-(2-fluoropropan-2-yl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound C=1N=C2N=C(C(C)(F)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=CC=C1C#N KDYOOVVMOGCFJJ-UHFFFAOYSA-N 0.000 claims description 3
QOVPIMPTICLHBJ-UHFFFAOYSA-N 2-[2-fluoro-5-[7-(triazol-1-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(CN4N=NC=C4)=NC3=NC=2)C=C1C1=CC=CC=C1C#N QOVPIMPTICLHBJ-UHFFFAOYSA-N 0.000 claims description 3
PBZZYPCPLXLAEX-UHFFFAOYSA-N 2-[2-fluoro-5-[7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]pyridine-3-carbonitrile Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=NC=CC=C1C#N PBZZYPCPLXLAEX-UHFFFAOYSA-N 0.000 claims description 3
SQABEUAMBJZDKI-UHFFFAOYSA-N 2-[3-(2-fluoro-3-pyridin-2-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1F)=CC=CC=1C1=CC=CC=N1 SQABEUAMBJZDKI-UHFFFAOYSA-N 0.000 claims description 3
ZJZYYCDLPZVBBJ-UHFFFAOYSA-N 2-[3-(4-fluoro-3-pyridazin-4-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=NN=C1 ZJZYYCDLPZVBBJ-UHFFFAOYSA-N 0.000 claims description 3
GFQMHVYMEKXHDT-UHFFFAOYSA-N 2-[3-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=C1 GFQMHVYMEKXHDT-UHFFFAOYSA-N 0.000 claims description 3
UVTIJQDSGQQUDX-UHFFFAOYSA-N 2-[3-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=NC=C(F)C=C1F UVTIJQDSGQQUDX-UHFFFAOYSA-N 0.000 claims description 3
ILFZZMYJRPZIPF-UHFFFAOYSA-N 2-[3-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=NC=CC=C1F ILFZZMYJRPZIPF-UHFFFAOYSA-N 0.000 claims description 3
IHDXFSAXAJRBOG-UHFFFAOYSA-N 2-[3-[4-fluoro-3-(5-fluoropyridin-2-yl)phenyl]imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=C(F)C=N1 IHDXFSAXAJRBOG-UHFFFAOYSA-N 0.000 claims description 3
YROULHXQJOCGCZ-UHFFFAOYSA-N 3-(2,4-difluoro-3-pyridin-2-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C(F)=C1C1=CC=CC=N1 YROULHXQJOCGCZ-UHFFFAOYSA-N 0.000 claims description 3
GXPAVMUVLDMPHC-UHFFFAOYSA-N 3-(4-fluoro-3-pyridazin-3-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=CN=N1 GXPAVMUVLDMPHC-UHFFFAOYSA-N 0.000 claims description 3
KNJSZFVFMIRFKF-UHFFFAOYSA-N 3-(4-fluoro-3-pyridin-3-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=CN=C1 KNJSZFVFMIRFKF-UHFFFAOYSA-N 0.000 claims description 3
XXVPCILZLAUFQI-UHFFFAOYSA-N 3-[2-fluoro-5-[7-(2-hydroxypropan-2-yl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]thiophene-2-carbonitrile Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C=1C=CSC=1C#N XXVPCILZLAUFQI-UHFFFAOYSA-N 0.000 claims description 3
ZHJZFEOIZZMCQB-UHFFFAOYSA-N 3-[2-fluoro-5-[7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]thiophene-2-carbonitrile Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C=1C=CSC=1C#N ZHJZFEOIZZMCQB-UHFFFAOYSA-N 0.000 claims description 3
YYUUQHSRIYPINT-UHFFFAOYSA-N 3-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC(F)=CN=C1C1=CC(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)=CC=C1F YYUUQHSRIYPINT-UHFFFAOYSA-N 0.000 claims description 3
AJWPZYMLAILYCO-UHFFFAOYSA-N 3-fluoro-2-[2-fluoro-5-[7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=C(F)C=CC=C1C#N AJWPZYMLAILYCO-UHFFFAOYSA-N 0.000 claims description 3
SYHJILPZUNKNHQ-UHFFFAOYSA-N 3-phenylbenzonitrile Chemical compound N#CC1=CC=CC(C=2C=CC=CC=2)=C1 SYHJILPZUNKNHQ-UHFFFAOYSA-N 0.000 claims description 3
IQKMZIHHJYCEKH-UHFFFAOYSA-N 4-[2-fluoro-5-[7-(2-hydroxypropan-2-yl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]pyridine-3-carbonitrile Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=NC=C1C#N IQKMZIHHJYCEKH-UHFFFAOYSA-N 0.000 claims description 3
XADIBLCMJSVYED-UHFFFAOYSA-N 4-[2-fluoro-5-[7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=C(C#N)C=C1 XADIBLCMJSVYED-UHFFFAOYSA-N 0.000 claims description 3
HJMFOCIFKIXNDK-UHFFFAOYSA-N 4-[2-fluoro-5-[7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]pyridine-3-carbonitrile Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=NC=C1C#N HJMFOCIFKIXNDK-UHFFFAOYSA-N 0.000 claims description 3
XXRKXVKJMSIZSM-UHFFFAOYSA-N 5-fluoro-2-[2-fluoro-5-[7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound N#CC1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)=CC=C1F XXRKXVKJMSIZSM-UHFFFAOYSA-N 0.000 claims description 3
NTZXPPSXVFCSOV-UHFFFAOYSA-N 7-(1,1-difluoroethyl)-3-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C=1N=C2N=C(C(F)(F)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=C1 NTZXPPSXVFCSOV-UHFFFAOYSA-N 0.000 claims description 3
GXGASOWVXWORBL-UHFFFAOYSA-N 7-(1,1-difluoroethyl)-3-(4-fluoro-3-pyridin-4-ylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C=1N=C2N=C(C(F)(F)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=NC=C1 GXGASOWVXWORBL-UHFFFAOYSA-N 0.000 claims description 3
125000005620 boronic acid group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
GXKGSEUULCEOTM-UHFFFAOYSA-N 2-[2-fluoro-3-[7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound FC1=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=CC=C1C1=CC=CC=C1C#N GXKGSEUULCEOTM-UHFFFAOYSA-N 0.000 claims description 2
SJZFHXXUTRMLFS-UHFFFAOYSA-N 2-[2-fluoro-5-(7-methylimidazo[1,2-a]pyrimidin-3-yl)phenyl]benzonitrile Chemical compound C=1N=C2N=C(C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=CC=C1C#N SJZFHXXUTRMLFS-UHFFFAOYSA-N 0.000 claims description 2
IMZKVYQYGGYNJK-UHFFFAOYSA-N 2-[2-fluoro-5-[7-(1,2,4-triazol-1-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(CN4N=CN=C4)=NC3=NC=2)C=C1C1=CC=CC=C1C#N IMZKVYQYGGYNJK-UHFFFAOYSA-N 0.000 claims description 2
KXISMKHPUSDPHX-UHFFFAOYSA-N 2-[2-fluoro-5-[7-(furan-3-yl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C2=COC=C2)C=C1C1=CC=CC=C1C#N KXISMKHPUSDPHX-UHFFFAOYSA-N 0.000 claims description 2
AKTMUWYDBRLMSY-UHFFFAOYSA-N 2-[2-fluoro-5-[7-(methoxymethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound C=1N=C2N=C(COC)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=CC=C1C#N AKTMUWYDBRLMSY-UHFFFAOYSA-N 0.000 claims description 2
NFYCVEMTEKXQBS-UHFFFAOYSA-N 2-[2-fluoro-5-[7-(triazol-2-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(CN4N=CC=N4)=NC3=NC=2)C=C1C1=CC=CC=C1C#N NFYCVEMTEKXQBS-UHFFFAOYSA-N 0.000 claims description 2
NVETZYIXXYETLA-UHFFFAOYSA-N 2-[2-fluoro-5-[7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=CC=C1C#N NVETZYIXXYETLA-UHFFFAOYSA-N 0.000 claims description 2
GWRIYCPCUOKPDE-UHFFFAOYSA-N 2-[3-(4-fluoro-3-pyrazin-2-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CN=CC=N1 GWRIYCPCUOKPDE-UHFFFAOYSA-N 0.000 claims description 2
CLRRRVBJVVEKRM-UHFFFAOYSA-N 2-[3-(4-fluoro-3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=CN2C=1C(C=1)=CC=C(F)C=1N1C=CC=N1 CLRRRVBJVVEKRM-UHFFFAOYSA-N 0.000 claims description 2
AYOJRPAXELLZLC-UHFFFAOYSA-N 2-[3-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-a]pyrimidin-7-yl]-2-methylpropanenitrile Chemical compound C=1N=C2N=C(C(C)(C#N)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=C1 AYOJRPAXELLZLC-UHFFFAOYSA-N 0.000 claims description 2
KMUKKBKUYITLNJ-UHFFFAOYSA-N 2-[5-(7-chloroimidazo[1,2-a]pyrimidin-3-yl)-2-fluorophenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3C=CC(Cl)=NC3=NC=2)C=C1C1=CC=CC=C1C#N KMUKKBKUYITLNJ-UHFFFAOYSA-N 0.000 claims description 2
BBEARXVYMAENJI-UHFFFAOYSA-N 2-[5-[7-(1,1-difluoroethyl)imidazo[1,2-a]pyrimidin-3-yl]-2-fluorophenyl]benzonitrile Chemical compound C=1N=C2N=C(C(F)(F)C)C=CN2C=1C(C=1)=CC=C(F)C=1C1=CC=CC=C1C#N BBEARXVYMAENJI-UHFFFAOYSA-N 0.000 claims description 2
JTFSFMVIELGGNP-UHFFFAOYSA-N 3-(2,4-difluoro-3-pyridin-3-ylphenyl)-7-(2-fluoropropan-2-yl)imidazo[1,2-a]pyrimidine Chemical compound C=1N=C2N=C(C(C)(F)C)C=CN2C=1C(C=1F)=CC=C(F)C=1C1=CC=CN=C1 JTFSFMVIELGGNP-UHFFFAOYSA-N 0.000 claims description 2
RJUGUDWQJXIJSH-UHFFFAOYSA-N 3-(2-fluoro-5-pyridin-3-ylphenyl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C=2N3C=CC(=NC3=NC=2)C(F)(F)F)C(F)=CC=C1C1=CC=CN=C1 RJUGUDWQJXIJSH-UHFFFAOYSA-N 0.000 claims description 2
WVXSTLAKWOUBRR-UHFFFAOYSA-N 3-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC=C(C=2N3C=CC=NC3=NC=2)C=C1C1=CC=CN=C1 WVXSTLAKWOUBRR-UHFFFAOYSA-N 0.000 claims description 2
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Classifications

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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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SK1167-2003A 2001-03-21 2002-03-19 Imidazopyrimidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie SK11672003A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB0107134A GB0107134D0 (en)	2001-03-21	2001-03-21	Therapeutic agents
GB0127938A GB0127938D0 (en)	2001-11-21	2001-11-21	Therapeutic agents
PCT/GB2002/001351 WO2002074772A1 (en)	2001-03-21	2002-03-19	Imidazo-pyrimidine derivatives as ligands for gaba receptors

Publications (1)

Publication Number	Publication Date
SK11672003A3 true SK11672003A3 (sk)	2004-05-04

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1167-2003A SK11672003A3 (sk)	2001-03-21	2002-03-19	Imidazopyrimidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (24)

Country	Link
EP (1)	EP1381606B1 (cs)
JP (1)	JP4409174B2 (cs)
KR (1)	KR20030083001A (cs)
CN (1)	CN1294133C (cs)
AT (1)	ATE299882T1 (cs)
AU (1)	AU2002241138B2 (cs)
BG (1)	BG108166A (cs)
BR (1)	BR0207994A (cs)
CA (1)	CA2461426C (cs)
CZ (1)	CZ20032539A3 (cs)
DE (1)	DE60205101T2 (cs)
EA (1)	EA006234B1 (cs)
EE (1)	EE200300455A (cs)
ES (1)	ES2244752T3 (cs)
HU (1)	HUP0303630A3 (cs)
IL (1)	IL157641A0 (cs)
MX (1)	MXPA03008572A (cs)
NO (1)	NO20034170L (cs)
NZ (1)	NZ527901A (cs)
PE (1)	PE20020970A1 (cs)
PL (1)	PL363804A1 (cs)
SK (1)	SK11672003A3 (cs)
TW (1)	TWI248936B (cs)
WO (2)	WO2002074773A1 (cs)

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GB0117277D0 (en)	2001-07-16	2001-09-05	Merck Sharp & Dohme	Therapeutic agents
GB0128499D0 (en) *	2001-11-28	2002-01-23	Merck Sharp & Dohme	Therapeutic agents
GB0226462D0 (en) *	2002-11-13	2002-12-18	Merck Sharp & Dohme	Therapeutic agents
BRPI0412908A (pt) *	2003-07-25	2006-09-26	Neurogen Corp	composto ou um sal deste farmaceuticamente aceitável, composição farmacêutica, métodos para o tratamento de ansiedade, depressão, um distúrbio do sono, distúrbio de déficit de atenção ou demência de alzheimer, para potenciar um efeito terapêutico de um agente do cns, para melhorar a memória de curta duração em um paciente, para alterar a atividade de transdução de sinal de receptor gabaa, e para determinar a presença ou ausência de receptor gabaa em uma amostra, preparação farmacêutica acondicionada, e, uso de um composto ou sal
HRP20150642T1 (hr)	2006-12-22	2015-08-14	Astex Therapeutics Limited	BICIKLIÄŚKE HETEROCIKLIÄŚKE TVARI KAO INHIBITORI FGFR-a
US8513276B2 (en)	2006-12-22	2013-08-20	Astex Therapeutics Limited	Imidazo[1,2-a]pyridine compounds for use in treating cancer
GB0720038D0 (en)	2007-10-12	2007-11-21	Astex Therapeutics Ltd	New compounds
GB0720041D0 (en)	2007-10-12	2007-11-21	Astex Therapeutics Ltd	New Compounds
GB0810902D0 (en)	2008-06-13	2008-07-23	Astex Therapeutics Ltd	New compounds
GB0906470D0 (en)	2009-04-15	2009-05-20	Astex Therapeutics Ltd	New compounds
GB0906472D0 (en)	2009-04-15	2009-05-20	Astex Therapeutics Ltd	New compounds
WO2011047320A2 (en)	2009-10-16	2011-04-21	Rib-X Pharmaceuticals, Inc.	Antimicrobial compounds and methods of making and using the same
US9216979B2 (en)	2009-10-16	2015-12-22	Melinta Therapeutics, Inc.	Antimicrobial compounds and methods of making and using the same
TW201726630A (zh) *	2009-10-16	2017-08-01	梅林塔療法公司	抗微生物性化合物及其製造與使用方法
US20150374705A1 (en)	2012-02-14	2015-12-31	Shanghai Institues for Biological Sciences	Substances for treatment or relief of pain
CN102898315B (zh) *	2012-11-05	2015-01-28	上海毕得医药科技有限公司	3-乙炔基-4-氟苯胺的制备方法
EP3038623A4 (en)	2013-09-09	2017-04-19	Melinta Therapeutics, Inc.	Antimicrobial compounds and methods of making and using the same
KR20160070066A (ko)	2013-09-09	2016-06-17	멜린타 테라퓨틱스, 인크.	항균 화합물, 및 이의 제조 방법 및 이용 방법
CA2979342A1 (en)	2015-03-11	2016-09-15	Melinta Therapeutics, Inc.	Antimicrobial compounds and methods of making and using the same
EP3386983A1 (en) *	2015-12-10	2018-10-17	Pfizer Limited	4-(biphen-3-yl)-1h-pyrazolo[3,4-c]pyridazine derivatives of formula (i) as gaba receptor modulators for use in the treatment of epilepsy and pain
WO2017129801A1 (en)	2016-01-27	2017-08-03	Universität Zürich	Use of gabaa receptor modulators for treatment of itch
WO2017193016A1 (en)	2016-05-06	2017-11-09	Melinta Therapeutics, Inc.	Antimicrobials and methods of making and using same
BR112020021104A2 (pt) *	2018-04-18	2021-02-23	Neurocycle Therapeutics, Inc	compostos moduladores alostéricos positivos gabaa, métodos de produção e usos dos mesmos

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US5185446A (en) *	1990-09-04	1993-02-09	Neurogen Corporation	Certain cycloalkyl imidazopyrimidines; a new class of gaba brainreceptor ligands
BR9608056A (pt) *	1995-04-21	1999-11-30	Neurosearch As	Compostos de benzimidazol, composições farmacêuticas contendo os compostos e sua utilização.
PA8535601A1 (es) *	2000-12-21	2002-11-28	Pfizer	Derivados benzimidazol y piridilimidazol como ligandos para gabaa

2002
- 2002-03-12 TW TW091104588A patent/TWI248936B/zh active
- 2002-03-19 DE DE60205101T patent/DE60205101T2/de not_active Expired - Lifetime
- 2002-03-19 HU HU0303630A patent/HUP0303630A3/hu unknown
- 2002-03-19 PE PE2002000211A patent/PE20020970A1/es not_active Application Discontinuation
- 2002-03-19 EE EEP200300455A patent/EE200300455A/xx unknown
- 2002-03-19 PL PL02363804A patent/PL363804A1/xx not_active Application Discontinuation
- 2002-03-19 MX MXPA03008572A patent/MXPA03008572A/es unknown
- 2002-03-19 ES ES02706976T patent/ES2244752T3/es not_active Expired - Lifetime
- 2002-03-19 AT AT02706976T patent/ATE299882T1/de not_active IP Right Cessation
- 2002-03-19 IL IL15764102A patent/IL157641A0/xx unknown
- 2002-03-19 KR KR10-2003-7012252A patent/KR20030083001A/ko not_active Withdrawn
- 2002-03-19 CN CNB028070577A patent/CN1294133C/zh not_active Expired - Fee Related
- 2002-03-19 SK SK1167-2003A patent/SK11672003A3/sk not_active Application Discontinuation
- 2002-03-19 CA CA2461426A patent/CA2461426C/en not_active Expired - Fee Related
- 2002-03-19 EP EP02706976A patent/EP1381606B1/en not_active Expired - Lifetime
- 2002-03-19 CZ CZ20032539A patent/CZ20032539A3/cs unknown
- 2002-03-19 WO PCT/GB2002/001352 patent/WO2002074773A1/en not_active Ceased
- 2002-03-19 WO PCT/GB2002/001351 patent/WO2002074772A1/en not_active Ceased
- 2002-03-19 JP JP2002573781A patent/JP4409174B2/ja not_active Expired - Fee Related
- 2002-03-19 BR BR0207994-1A patent/BR0207994A/pt not_active IP Right Cessation
- 2002-03-19 AU AU2002241138A patent/AU2002241138B2/en not_active Ceased
- 2002-03-19 NZ NZ527901A patent/NZ527901A/en unknown
- 2002-03-19 EA EA200301037A patent/EA006234B1/ru not_active IP Right Cessation
2003
- 2003-09-09 BG BG108166A patent/BG108166A/xx unknown
- 2003-09-19 NO NO20034170A patent/NO20034170L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1294133C (zh)	2007-01-10
CA2461426C (en)	2010-08-03
NO20034170D0 (no)	2003-09-19
EA006234B1 (ru)	2005-10-27
BG108166A (en)	2004-09-30
IL157641A0 (en)	2004-03-28
JP2004523584A (ja)	2004-08-05
BR0207994A (pt)	2004-03-02
HUP0303630A3 (en)	2005-06-28
TWI248936B (en)	2006-02-11
NO20034170L (no)	2003-11-19
DE60205101D1 (de)	2005-08-25
EP1381606B1 (en)	2005-07-20
JP4409174B2 (ja)	2010-02-03
EP1381606A1 (en)	2004-01-21
MXPA03008572A (es)	2003-12-08
ATE299882T1 (de)	2005-08-15
EA200301037A1 (ru)	2004-04-29
CZ20032539A3 (en)	2004-03-17
CA2461426A1 (en)	2002-09-26
AU2002241138B2 (en)	2007-09-20
DE60205101T2 (de)	2006-05-24
HUP0303630A2 (hu)	2004-03-01
WO2002074772A1 (en)	2002-09-26
CN1498218A (zh)	2004-05-19
PE20020970A1 (es)	2002-11-01
NZ527901A (en)	2005-09-30
PL363804A1 (en)	2004-11-29
ES2244752T3 (es)	2005-12-16
KR20030083001A (ko)	2003-10-23
WO2002074773A1 (en)	2002-09-26
EE200300455A (et)	2003-12-15

Legal Events

Date	Code	Title	Description
2010-12-07	FC9A	Refused patent application

Publication	Publication Date	Title
SK11672003A3 (sk)	2004-05-04	Imidazopyrimidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie
US7005431B2 (en)	2006-02-28	Imidazo-triazine derivatives as ligands for gaba receptors
EP1383768B1 (en)	2006-09-06	Imidazo-pyrimidine derivatives as ligands for gaba receptors
EP1511747B1 (en)	2006-04-12	Imidazo-pyridine derivatives as ligands for gaba receptors
US6936608B2 (en)	2005-08-30	Imidazo-triazine derivatives as ligands for GABA receptors
EP1451161B1 (en)	2007-04-18	Imidazopyridines, pyrimidines and triazines for enhancing cognition as gaba-a alpha 5 receptor subtype ligands
AU2002317957B2 (en)	2007-10-25	Imidazo-triazine derivatives as ligands for GABA receptors
US6642229B2 (en)	2003-11-04	3-Phenyl-imidazo-pyrimidine derivatives as ligands for GABA receptors
US6900215B2 (en)	2005-05-31	Imidazo-pyrimidine derivatives as ligands for gaba receptors
AU2002241139A1 (en)	2003-03-27	Imidazo-pyrimidine derivatives as ligands for GABA receptors
US7226926B2 (en)	2007-06-05	8-fluoroimidazo 1,2-a pyridine derivatives as ligands for GABA receptors
AU2002241138A1 (en)	2003-03-27	Imidazo-pyrimidine derivatives as ligands for GABA receptors
US7381725B2 (en)	2008-06-03	Pyridazine derivatives as ligands for GABA receptors