ZA200308726B - Imidazo [1,2-A] pyridine derivatives for the prophylaxis and treatment of herpes viral infections. - Google Patents
Imidazo [1,2-A] pyridine derivatives for the prophylaxis and treatment of herpes viral infections. Download PDFInfo
- Publication number
- ZA200308726B ZA200308726B ZA200308726A ZA200308726A ZA200308726B ZA 200308726 B ZA200308726 B ZA 200308726B ZA 200308726 A ZA200308726 A ZA 200308726A ZA 200308726 A ZA200308726 A ZA 200308726A ZA 200308726 B ZA200308726 B ZA 200308726B
- Authority
- ZA
- South Africa
- Prior art keywords
- imidazo
- het
- cyclopentylamino
- pyridin
- pyrimidinyl
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 19
- 206010019972 Herpes viral infections Diseases 0.000 title claims description 18
- 238000011321 prophylaxis Methods 0.000 title claims description 17
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 80
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- -1 methoxyphenyl Chemical group 0.000 claims description 12
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 8
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
- 241000701022 Cytomegalovirus Species 0.000 claims description 6
- 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 5
- 241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 5
- 241000701041 Human betaherpesvirus 7 Species 0.000 claims description 5
- 241000701027 Human herpesvirus 6 Species 0.000 claims description 5
- HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 claims description 4
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 229960004150 aciclovir Drugs 0.000 claims description 3
- 229940093257 valacyclovir Drugs 0.000 claims description 3
- 241001502974 Human gammaherpesvirus 8 Species 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- GRFOHUBBUMAJMM-UHFFFAOYSA-N 3-(2-aminoquinolin-3-yl)-n-cyclohexyl-n-methylpropanamide Chemical compound C=1C2=CC=CC=C2N=C(N)C=1CCC(=O)N(C)C1CCCCC1 GRFOHUBBUMAJMM-UHFFFAOYSA-N 0.000 claims 2
- LKQXJYDAALZCAF-UHFFFAOYSA-N imidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CN2C=CN=C12 LKQXJYDAALZCAF-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 2
- GVJZSWGXJJEWND-UHFFFAOYSA-N 2-(3-aminophenyl)-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CC(C2=C(N3C=CC=C(NC4CCCC4)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 GVJZSWGXJJEWND-UHFFFAOYSA-N 0.000 claims 1
- FLJWRLOENAETFF-UHFFFAOYSA-N 2-(trifluoromethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CN2C=C(C(F)(F)F)N=C12 FLJWRLOENAETFF-UHFFFAOYSA-N 0.000 claims 1
- UQKWYOKJTAQZEW-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-ol Chemical compound N1=C2C(O)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 UQKWYOKJTAQZEW-UHFFFAOYSA-N 0.000 claims 1
- WJDLDBKLZHQTFK-UHFFFAOYSA-N 4-[8-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 WJDLDBKLZHQTFK-UHFFFAOYSA-N 0.000 claims 1
- FTCYXGSDEVJSSB-UHFFFAOYSA-N 4-[8-chloro-2-(3-nitrophenyl)imidazo[1,2-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound [O-][N+](=O)C1=CC=CC(C2=C(N3C=CC=C(Cl)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 FTCYXGSDEVJSSB-UHFFFAOYSA-N 0.000 claims 1
- ULQMUCVMULQROI-UHFFFAOYSA-N 4-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(Cl)C2=N1 ULQMUCVMULQROI-UHFFFAOYSA-N 0.000 claims 1
- AFYKGCFGZVJIQB-UHFFFAOYSA-N 4-cyclopentylpyrimidin-2-amine Chemical compound NC1=NC=CC(C2CCCC2)=N1 AFYKGCFGZVJIQB-UHFFFAOYSA-N 0.000 claims 1
- PXKQLJBZGIJPDM-UHFFFAOYSA-N 6-bromo-n-butyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C2C(NCCCC)=CC(Br)=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 PXKQLJBZGIJPDM-UHFFFAOYSA-N 0.000 claims 1
- FQNLYAUKXFCGMX-UHFFFAOYSA-N 8-chloro-2-(4-fluorophenyl)-3-(2-fluoropyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C(F)N=CC=2)N2C=CC=C(Cl)C2=N1 FQNLYAUKXFCGMX-UHFFFAOYSA-N 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- ZTIGLNXZTZDSSR-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(3-methoxyphenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound COC1=CC=CC(C2=C(N3C=CC=C(NC4CCCC4)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 ZTIGLNXZTZDSSR-UHFFFAOYSA-N 0.000 claims 1
- KDCXXXLSBHIBQK-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 KDCXXXLSBHIBQK-UHFFFAOYSA-N 0.000 claims 1
- UTSMIQYHCSZTSP-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methylphenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(C)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 UTSMIQYHCSZTSP-UHFFFAOYSA-N 0.000 claims 1
- ZVFBUFIJHUDYHP-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[4-(cyclopropylmethoxy)phenyl]imidazo[1,2-a]pyridin-8-amine Chemical compound C1CC1COC(C=C1)=CC=C1C(=C(N1C=CC=2)C=3N=C(NC4CCCC4)N=CC=3)N=C1C=2NC1CCCC1 ZVFBUFIJHUDYHP-UHFFFAOYSA-N 0.000 claims 1
- HXLGDAAWRUWBGI-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-8-pyrrolidin-1-ylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(N3CCCC3)C2=N1 HXLGDAAWRUWBGI-UHFFFAOYSA-N 0.000 claims 1
- LFAOAOFMOZLDCM-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=CC2=N1 LFAOAOFMOZLDCM-UHFFFAOYSA-N 0.000 claims 1
- CEYKJBAJFUSKPH-UHFFFAOYSA-N n-cyclopentyl-4-[6,8-dibromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=C(Br)C=C(Br)C2=N1 CEYKJBAJFUSKPH-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 description 14
- 208000015181 infectious disease Diseases 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 241000700605 Viruses Species 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 208000007514 Herpes zoster Diseases 0.000 description 5
- 201000006747 infectious mononucleosis Diseases 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 241001529453 unidentified herpesvirus Species 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical group 0.000 description 3
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 201000006082 Chickenpox Diseases 0.000 description 2
- 206010015108 Epstein-Barr virus infection Diseases 0.000 description 2
- 241000700721 Hepatitis B virus Species 0.000 description 2
- 208000001688 Herpes Genitalis Diseases 0.000 description 2
- 208000009889 Herpes Simplex Diseases 0.000 description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- 206010061598 Immunodeficiency Diseases 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 208000030289 Lymphoproliferative disease Diseases 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 206010038910 Retinitis Diseases 0.000 description 2
- 241000700584 Simplexvirus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 206010046980 Varicella Diseases 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 230000007012 clinical effect Effects 0.000 description 2
- 231100000676 disease causative agent Toxicity 0.000 description 2
- 201000004946 genital herpes Diseases 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 229940124589 immunosuppressive drug Drugs 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000306 recurrent effect Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000011691 Burkitt lymphomas Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 206010062343 Congenital infection Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010011831 Cytomegalovirus infection Diseases 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 208000001860 Eye Infections Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 208000005794 Hairy Leukoplakia Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000004898 Herpes Labialis Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 206010024971 Lower respiratory tract infections Diseases 0.000 description 1
- 208000036626 Mental retardation Diseases 0.000 description 1
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 206010067152 Oral herpes Diseases 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010035742 Pneumonitis Diseases 0.000 description 1
- 206010037898 Rash vesicular Diseases 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 208000033779 X-linked lymphoproliferative disease Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 206010016165 failure to thrive Diseases 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
- 206010019847 hepatosplenomegaly Diseases 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 210000002418 meninge Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000004141 microcephaly Diseases 0.000 description 1
- 125000001620 monocyclic carbocycle group Chemical group 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 201000011216 nasopharynx carcinoma Diseases 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000005485 negative regulation of interleukin-1 production Effects 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 210000003061 neural cell Anatomy 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 206010030979 oral hairy leukoplakia Diseases 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 231100000046 skin rash Toxicity 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 208000008732 thymoma Diseases 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 230000006433 tumor necrosis factor production Effects 0.000 description 1
- 229940108442 valtrex Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229940107931 zovirax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30000901P | 2001-06-21 | 2001-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308726B true ZA200308726B (en) | 2005-02-10 |
Family
ID=23157269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308726A ZA200308726B (en) | 2001-06-21 | 2003-11-10 | Imidazo [1,2-A] pyridine derivatives for the prophylaxis and treatment of herpes viral infections. |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7186714B2 (enExample) |
| EP (1) | EP1401836B1 (enExample) |
| JP (1) | JP2005500315A (enExample) |
| KR (1) | KR20040018281A (enExample) |
| CN (1) | CN1518550A (enExample) |
| AT (1) | ATE337316T1 (enExample) |
| BR (1) | BR0210464A (enExample) |
| CA (1) | CA2451008A1 (enExample) |
| CO (1) | CO5540312A2 (enExample) |
| CZ (1) | CZ20033518A3 (enExample) |
| DE (1) | DE60214179T2 (enExample) |
| ES (1) | ES2271273T3 (enExample) |
| HU (1) | HUP0400266A2 (enExample) |
| IL (1) | IL158667A0 (enExample) |
| MX (1) | MXPA03011906A (enExample) |
| NO (1) | NO20035583D0 (enExample) |
| PL (1) | PL366827A1 (enExample) |
| WO (1) | WO2003000689A1 (enExample) |
| ZA (1) | ZA200308726B (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6977574B1 (en) * | 1997-02-14 | 2005-12-20 | Denso Corporation | Stick-type ignition coil having improved structure against crack or dielectric discharge |
| PL366827A1 (en) * | 2001-06-21 | 2005-02-07 | Smithkline Beecham Corporation | Imidazo[1,2-a]pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| AU2003217712A1 (en) | 2002-03-07 | 2003-09-22 | Smithkline Beecham Corporation | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them |
| CA2577947A1 (en) * | 2004-08-31 | 2006-03-09 | Banyu Pharmaceutical Co., Ltd. | Novel substituted imidazole derivative |
| ES2376491T3 (es) | 2006-05-19 | 2012-03-14 | Nihon Medi-Physics Co., Ltd. | Compuesto que tiene afinidad por amiloide. |
| EP2098523A4 (en) * | 2006-11-17 | 2011-09-21 | Nihon Mediphysics Co Ltd | NOVEL COMPOUNDS WITH AFFINITY FOR THE AMYLOID SUBSTANCE |
| CA2670436A1 (en) | 2006-11-30 | 2008-06-05 | Nihon Medi-Physics Co., Ltd. | Novel compound having affinity for amyloid |
| KR101485445B1 (ko) | 2007-02-13 | 2015-01-22 | 니혼 메디피직스 가부시키가이샤 | 방사성 화상진단제의 제조 방법 |
| EP1964840A1 (en) | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]pyridines and their use as pharmaceuticals |
| EP2213672A4 (en) * | 2007-10-24 | 2012-05-02 | Nihon Mediphysics Co Ltd | NEW CONNECTION WITH AFFINITY TO AMYLOID |
| CN101909658A (zh) * | 2007-10-30 | 2010-12-08 | 日本医事物理股份有限公司 | 对淀粉样蛋白具有亲和性的新化合物的应用及制备方法 |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| WO2010009139A2 (en) | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Imidazolyl pyrimidine inhibitor compounds |
| EP2303841A1 (en) | 2008-07-14 | 2011-04-06 | Gilead Sciences, Inc. | Oxindolyl inhibitor compounds |
| WO2010009155A2 (en) | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Fused heterocyclyc inhibitor compounds |
| MX2011001090A (es) | 2008-07-28 | 2011-03-15 | Gilead Sciences Inc | Compuestos de inhibidor de desacetilasa de histona de cicloalquilideno y heterocicloalquilideno. |
| US20100204265A1 (en) * | 2009-02-09 | 2010-08-12 | Genelabs Technologies, Inc. | Certain Nitrogen Containing Bicyclic Chemical Entities for Treating Viral Infections |
| AU2010259042A1 (en) | 2009-06-08 | 2011-12-15 | Gilead Sciences, Inc. | Cycloalkylcarbamate benzamide aniline HDAC inhibitor compounds |
| EP2440519A1 (en) | 2009-06-08 | 2012-04-18 | Gilead Sciences, Inc. | Alkanoylamino benzamide aniline hdac inihibitor compounds |
| WO2011041713A2 (en) * | 2009-10-02 | 2011-04-07 | Glaxosmithkline Llc | Piperazinyl antiviral agents |
| EP2493889B1 (en) | 2009-10-30 | 2017-09-06 | Janssen Pharmaceutica, N.V. | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| MX344600B (es) | 2011-06-27 | 2016-12-20 | Janssen Pharmaceutica Nv | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxalina. |
| HK1206250A1 (en) | 2012-06-26 | 2016-01-08 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| CN104411314B (zh) | 2012-07-09 | 2017-10-20 | 詹森药业有限公司 | 磷酸二酯酶10的抑制剂 |
| ES2625744T3 (es) * | 2013-06-04 | 2017-07-20 | Bayer Pharma Aktiengesellschaft | Imidazo[1,2-a]piridinas sustituidas con 3-arilo y su uso |
| WO2015103137A1 (en) | 2013-12-30 | 2015-07-09 | Array Biopharma Inc. | Serine/threonine kinase inhibitors |
| CA2939793A1 (en) | 2014-02-19 | 2015-08-27 | Bayer Pharma Aktiengesellschaft | 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines |
| US11071745B2 (en) * | 2014-07-07 | 2021-07-27 | Elian Llc | Viral prophylaxis treatment methods and pre-exposure prophylaxis kits |
| EP3227287B1 (de) | 2014-12-02 | 2019-08-07 | Bayer Pharma Aktiengesellschaft | Heteroaryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung |
| WO2018141002A2 (en) * | 2017-02-01 | 2018-08-09 | University Of South Australia | DERIVATIVES OF N-CYCLOALKYL/HETEROCYCLOALKYL-4-(IMIDAZO [1,2-a]PYRIDINE)PYRIMIDIN-2-AMINE AS THERAPEUTIC AGENTS |
| CN110483506B (zh) * | 2019-08-02 | 2022-04-19 | 桂林理工大学 | 以DMF为甲酰化试剂构建2-(2-噻吩基)咪唑[1,2-a]吡啶-3-醛的新方法 |
| CN110483504B (zh) * | 2019-08-02 | 2022-04-26 | 桂林理工大学 | 以DMF为甲酰化试剂构建2-(2-萘基)咪唑[1,2-a]吡啶-3-醛的新方法 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0151962A3 (en) | 1984-01-25 | 1985-10-02 | Beecham Group Plc | Pyrazolopyridine derivatives |
| GB8404584D0 (en) | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
| GB8404586D0 (en) | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
| US4719218A (en) | 1985-12-12 | 1988-01-12 | Smithkline Beckman Corporation | Pyrrolo[1,2-a]imidazole and pyrrolo[1,2-a]pyridine derivatives and their use as 5-lipoxygenase pathway inhibitor |
| US5145858A (en) | 1985-12-12 | 1992-09-08 | Smithkline Beecham Corp. | Pyrrolo [1,2-a] imidazole and imidazo [1,2a] pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors |
| US5002941A (en) | 1985-12-12 | 1991-03-26 | Smithkline Beecham Corporation | Pyrrolo(1,2-a)imidazole and imidazo(1,2-a)pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors |
| US4794114A (en) | 1986-08-19 | 1988-12-27 | Smithkline Beckman Corporation | Inhibition of interleukin-1 production by monocytes and/or macrophages |
| US4925849A (en) | 1987-06-15 | 1990-05-15 | Fujisawa Pharmaceutical Company, Ltd. | Pharmaceutically useful pyrazolopyridines |
| US5155114A (en) | 1989-01-23 | 1992-10-13 | Fujisawa Pharmaceutical Company, Ltd. | Method of treatment using pyrazolopyridine compound |
| GB8901423D0 (en) | 1989-01-23 | 1989-03-15 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| AU6355190A (en) | 1989-06-13 | 1991-01-17 | Smithkline Beecham Corporation | Inhibition of interleukin-1 and tumor necrosis factor production by monocytes and/or macrophages |
| AU5921890A (en) | 1989-06-13 | 1991-01-08 | Smithkline Beecham Corporation | Monokine activity interference |
| AU622330B2 (en) | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
| KR930700104A (ko) * | 1990-06-12 | 1993-03-13 | 원본미기재 | 5-리프옥시게나제 및 사이클로옥시게나제 경로 개재된 질병의 억제 |
| GB9015764D0 (en) | 1990-07-18 | 1990-09-05 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| GB9026926D0 (en) | 1990-12-12 | 1991-01-30 | Smith Kline French Lab | Novel process |
| AU9137591A (en) | 1990-12-13 | 1992-07-08 | Smithkline Beecham Corporation | Novel csaids |
| WO1992010498A1 (en) | 1990-12-13 | 1992-06-25 | Smithkline Beecham Corporation | Novel csaids |
| EP0497258B1 (en) | 1991-01-29 | 2002-01-02 | Fujisawa Pharmaceutical Co., Ltd. | Use of adenosine antagonists in the prevention and treatment of pancreatitis and ulcer |
| GB9107513D0 (en) | 1991-04-10 | 1991-05-29 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| US5300478A (en) | 1993-01-28 | 1994-04-05 | Zeneca Limited | Substituted fused pyrazolo compounds |
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5521213A (en) | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
| CN1088062C (zh) | 1994-11-23 | 2002-07-24 | 纽罗根公司 | 某些4－氨基甲基－2－取代的咪唑衍生物2－氨基甲基－4－取代的咪唑衍生物新的一族多巴胺受体亚型特异性配体 |
| US5552422A (en) | 1995-01-11 | 1996-09-03 | Merck Frosst Canada, Inc. | Aryl substituted 5,5 fused aromatic nitrogen compounds as anti-inflammatory agents |
| KR19980703559A (ko) | 1995-04-04 | 1998-11-05 | 그레이엄브레레톤 | 이미다조［1,2-ａ］피리딘 유도체 |
| WO1996034866A1 (en) | 1995-05-01 | 1996-11-07 | Fujisawa Pharmaceutical Co., Ltd. | Imidazo 1,2-a pyridine and imidazo 1,2-a pyridezine derivatives and their use as bone resorption inhibitors |
| US5700816A (en) | 1995-06-12 | 1997-12-23 | Isakson; Peter C. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor |
| CA2224517A1 (en) | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor |
| US6342510B1 (en) | 1995-06-12 | 2002-01-29 | G. D. Searle & Co. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitors and a leukotriene B4 receptor antagonist |
| FR2757166B1 (fr) | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2757059B1 (fr) * | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Nouvelle application therapeutique des derives du pyrrole |
| AU7966198A (en) | 1997-06-13 | 1998-12-30 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
| ATE281458T1 (de) | 1997-09-05 | 2004-11-15 | Glaxo Group Ltd | Pharmazeutische zusammensetzung, enthaltend 2,3- diaryl-pyrazolo(1,5-b)pyridazin derivate |
| CA2331878A1 (en) | 1998-05-14 | 1999-11-18 | G.D. Searle & Co. | 1,5-diaryl substituted pyrazoles as p38 kinase inhibitors |
| US6245789B1 (en) | 1998-05-19 | 2001-06-12 | The Procter & Gamble Company | HIV and viral treatment |
| FR2779724B1 (fr) | 1998-06-10 | 2001-04-20 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US7223772B1 (en) | 1998-11-03 | 2007-05-29 | Smithkline Beecham Corporation | Pyrazolopyridine derivatives as selective cox-2 inhibitors |
| EP1157025B1 (en) | 1999-02-27 | 2004-03-10 | Glaxo Group Limited | Pyrazolopyridines |
| JP4032566B2 (ja) | 1999-06-21 | 2008-01-16 | 東レ株式会社 | 発光素子 |
| BR0011997A (pt) | 1999-06-28 | 2002-03-05 | Janssen Pharmaceutica Nv | Inibidores da replicação do vìrus sincicial respiratório |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| CA2311483A1 (en) | 2000-06-12 | 2001-12-12 | Gregory N Beatch | IMIDAZO [1,2-A] PYRIDINIC ETHERS AND USES THEREOF |
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| AUPQ969800A0 (en) | 2000-08-28 | 2000-09-21 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| ATE301653T1 (de) | 2000-12-15 | 2005-08-15 | Glaxo Group Ltd | Pyrazolopyridine |
| AU2002239348A1 (en) | 2000-12-15 | 2002-06-24 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| PL366827A1 (en) * | 2001-06-21 | 2005-02-07 | Smithkline Beecham Corporation | Imidazo[1,2-a]pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| WO2003000682A1 (en) | 2001-06-25 | 2003-01-03 | Merck & Co., Inc. | (pyrimidyl)(phenyl)substituted fused heteroaryl p38 inhibiting and pkg kinase inhibiting compounds |
| ATE326466T1 (de) * | 2001-10-05 | 2006-06-15 | Smithkline Beecham Corp | Imidazopyridinderivate zur verwendung bei der behandlung von herpes-vireninfektion |
| US6711762B2 (en) | 2002-01-30 | 2004-03-30 | Ktk Services, Inc. | Method of using a truck cab bridge bed |
-
2002
- 2002-06-10 PL PL02366827A patent/PL366827A1/xx not_active Application Discontinuation
- 2002-06-10 CA CA002451008A patent/CA2451008A1/en not_active Abandoned
- 2002-06-10 CN CNA028124499A patent/CN1518550A/zh active Pending
- 2002-06-10 EP EP02739833A patent/EP1401836B1/en not_active Expired - Lifetime
- 2002-06-10 BR BR0210464-4A patent/BR0210464A/pt not_active Application Discontinuation
- 2002-06-10 HU HU0400266A patent/HUP0400266A2/hu unknown
- 2002-06-10 ES ES02739833T patent/ES2271273T3/es not_active Expired - Lifetime
- 2002-06-10 AT AT02739833T patent/ATE337316T1/de not_active IP Right Cessation
- 2002-06-10 US US10/479,526 patent/US7186714B2/en not_active Expired - Fee Related
- 2002-06-10 DE DE60214179T patent/DE60214179T2/de not_active Expired - Fee Related
- 2002-06-10 WO PCT/US2002/018520 patent/WO2003000689A1/en not_active Ceased
- 2002-06-10 IL IL15866702A patent/IL158667A0/xx unknown
- 2002-06-10 JP JP2003507092A patent/JP2005500315A/ja active Pending
- 2002-06-10 KR KR10-2003-7016716A patent/KR20040018281A/ko not_active Withdrawn
- 2002-06-10 MX MXPA03011906A patent/MXPA03011906A/es unknown
- 2002-06-10 CZ CZ20033518A patent/CZ20033518A3/cs unknown
-
2003
- 2003-11-10 ZA ZA200308726A patent/ZA200308726B/en unknown
- 2003-12-15 NO NO20035583A patent/NO20035583D0/no not_active Application Discontinuation
- 2003-12-16 CO CO03109957A patent/CO5540312A2/es not_active Application Discontinuation
-
2006
- 2006-03-29 US US11/391,867 patent/US20060167252A1/en not_active Abandoned
-
2007
- 2007-01-25 US US11/627,078 patent/US20070135451A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE337316T1 (de) | 2006-09-15 |
| MXPA03011906A (es) | 2004-03-26 |
| NO20035583D0 (no) | 2003-12-15 |
| CA2451008A1 (en) | 2003-01-03 |
| JP2005500315A (ja) | 2005-01-06 |
| CZ20033518A3 (en) | 2004-05-12 |
| CO5540312A2 (es) | 2005-07-29 |
| HUP0400266A2 (hu) | 2004-08-30 |
| US20050228004A1 (en) | 2005-10-13 |
| BR0210464A (pt) | 2004-07-20 |
| DE60214179T2 (de) | 2007-01-04 |
| US7186714B2 (en) | 2007-03-06 |
| US20060167252A1 (en) | 2006-07-27 |
| US20070135451A1 (en) | 2007-06-14 |
| EP1401836B1 (en) | 2006-08-23 |
| CN1518550A (zh) | 2004-08-04 |
| KR20040018281A (ko) | 2004-03-02 |
| WO2003000689A1 (en) | 2003-01-03 |
| IL158667A0 (en) | 2004-05-12 |
| DE60214179D1 (de) | 2006-10-05 |
| ES2271273T3 (es) | 2007-04-16 |
| PL366827A1 (en) | 2005-02-07 |
| EP1401836A1 (en) | 2004-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200308726B (en) | Imidazo [1,2-A] pyridine derivatives for the prophylaxis and treatment of herpes viral infections. | |
| US7153863B2 (en) | Therapeutic compounds based on pyrazolopyridline derivatives | |
| EP1504004B1 (en) | Substituted pyrazolopyrimidines | |
| EP2220091B1 (en) | Reverse transcriptase inhibitors | |
| CA2972014C (en) | Fused pyrimidine compounds for the treatment of hiv | |
| KR101727264B1 (ko) | 이미다조〔2,1-ｂ〕〔1,3,4〕티아디아졸 유도체 | |
| EP1377573B1 (en) | Pyrazolopyridine derivatives | |
| CA3005921A1 (en) | Substituted-(pyrrolo[2,3-b]pyridin-3-yl)-pyrimidin derivatives and use thereof as inhibitors of influenza virus replication | |
| AU2006261607A1 (en) | Pyrido(3,2-d)pyrimidines and pharmaceutical compositions useful for treating hepatitis C. | |
| EP1372643A1 (en) | Pyrazolopyridines, process for their preparation and use as therapeutic compounds | |
| EP1485385A1 (en) | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them | |
| CN119894888A (zh) | 用于治疗hsv的环尿素噻唑基化合物 | |
| AU2010335628B2 (en) | Pyrrolopyridinyl-pyrimidin-2-ylamine derivatives | |
| JP2015522034A (ja) | シアノグアニジン類および抗ウィルス剤としてのそれらの使用 | |
| EP1453830B1 (en) | Pyrazolo-pyridine derivatives as antiherpes agents | |
| US20110201665A1 (en) | Compositions, Methods, and Kits for Treating Influenza Viral Infections | |
| EP0746559A1 (en) | Pyrrolo(2,3-d)pyrimidine derivatives as antivirals | |
| US6964968B2 (en) | Method for the treatment or prevention of viral infection using nucleoside analogues | |
| WO1995001355A1 (en) | 9-deazahypoxanthines as pnp inhibitors | |
| WO2024049803A1 (en) | Bicyclic heterocycle compounds for treatment of herpes viruses | |
| EP0671918B1 (en) | Compositions containing acyclovir-like compounds and 2'-vinyl substituted nucleoside analogs for the treatment of viral infections | |
| EP0394346A1 (en) | Pyrimidine and purine 1,2-butadiene-4-ols as anti-retroviral agents | |
| WO2025227145A1 (en) | Benzamide compounds for treatment of herpes viruses | |
| US20250171413A1 (en) | Antiviral indolinyl compounds and uses thereof | |
| TW202241428A (zh) | Ｓａｒｓ－ｃｏｖ－２所引起之病毒感染的方法及治療 |