ES2360222T3 - Agentes policíclicos para el tratamiento de infecciones respiratorias por virus sincicial. - Google Patents
Agentes policíclicos para el tratamiento de infecciones respiratorias por virus sincicial. Download PDFInfo
- Publication number
- ES2360222T3 ES2360222T3 ES04802131T ES04802131T ES2360222T3 ES 2360222 T3 ES2360222 T3 ES 2360222T3 ES 04802131 T ES04802131 T ES 04802131T ES 04802131 T ES04802131 T ES 04802131T ES 2360222 T3 ES2360222 T3 ES 2360222T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- tetrahydro
- inden
- chlorophenyl
- triazacyclopenta
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000011282 treatment Methods 0.000 title claims abstract description 35
- 241000700605 Viruses Species 0.000 title claims abstract description 18
- 206010057190 Respiratory tract infections Diseases 0.000 title description 2
- 230000001351 cycling effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 210
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 142
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 84
- 150000003839 salts Chemical class 0.000 claims abstract description 58
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 31
- 125000004429 atom Chemical group 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 208000015181 infectious disease Diseases 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 241000711904 Pneumoviridae Species 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims description 123
- -1 C2- alkenyl groups 6 Chemical group 0.000 claims description 113
- 125000000623 heterocyclic group Chemical group 0.000 claims description 105
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 98
- 125000005843 halogen group Chemical group 0.000 claims description 55
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 52
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 47
- 125000003342 alkenyl group Chemical group 0.000 claims description 45
- 125000000304 alkynyl group Chemical group 0.000 claims description 45
- 241000725643 Respiratory syncytial virus Species 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 18
- 125000002541 furyl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 150000001204 N-oxides Chemical group 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 10
- 235000001014 amino acid Nutrition 0.000 claims description 10
- 229940024606 amino acid Drugs 0.000 claims description 10
- 150000001413 amino acids Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 9
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 9
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003838 furazanyl group Chemical group 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 5
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 5
- QWCKQJZIFLGMSD-UHFFFAOYSA-N 2-Aminobutanoic acid Natural products CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 claims description 5
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 5
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 claims description 5
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004471 Glycine Substances 0.000 claims description 5
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 5
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 5
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 claims description 5
- 241000711902 Pneumovirus Species 0.000 claims description 5
- 235000004279 alanine Nutrition 0.000 claims description 5
- 235000009582 asparagine Nutrition 0.000 claims description 5
- 229960001230 asparagine Drugs 0.000 claims description 5
- 235000003704 aspartic acid Nutrition 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 5
- 235000013922 glutamic acid Nutrition 0.000 claims description 5
- 239000004220 glutamic acid Substances 0.000 claims description 5
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 5
- 235000004554 glutamine Nutrition 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 4
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 238000007499 fusion processing Methods 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 claims description 3
- 241000282414 Homo sapiens Species 0.000 claims description 3
- 241000351643 Metapneumovirus Species 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 2
- VHUHJRFNZCOLES-UHFFFAOYSA-N 1-(1-benzofuran-2-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CC2=CC=CC=C2O1 VHUHJRFNZCOLES-UHFFFAOYSA-N 0.000 claims 1
- KSZFMJSXQCZHKJ-UHFFFAOYSA-N 1-(1-benzothiophene-2-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CC2=CC=CC=C2S1 KSZFMJSXQCZHKJ-UHFFFAOYSA-N 0.000 claims 1
- ROINWXQEKNGUBF-UHFFFAOYSA-N 1-(1-benzothiophene-3-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CSC2=CC=CC=C12 ROINWXQEKNGUBF-UHFFFAOYSA-N 0.000 claims 1
- RPFYBBYJSUVOKV-UHFFFAOYSA-N 1-(2,1-benzoxazole-3-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=C2C=CC=CC2=NO1 RPFYBBYJSUVOKV-UHFFFAOYSA-N 0.000 claims 1
- DSUCWLRJLKMJMA-UHFFFAOYSA-N 1-(3-bromothiophene-2-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=C(Br)C=CS1 DSUCWLRJLKMJMA-UHFFFAOYSA-N 0.000 claims 1
- SUUXEFDXGNFRNX-UHFFFAOYSA-N 1-(3-chloro-4-methylsulfonylthiophene-2-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound CS(=O)(=O)C1=CSC(C(=O)N2C3(C4=CN=CC=C4C(=O)N3CC2)C=2C=CC(Cl)=CC=2)=C1Cl SUUXEFDXGNFRNX-UHFFFAOYSA-N 0.000 claims 1
- NHBKIBNBSIWPJT-UHFFFAOYSA-N 1-(3-chloro-4-methylthiophene-2-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound CC1=CSC(C(=O)N2C3(C4=CN=CC=C4C(=O)N3CC2)C=2C=CC(Cl)=CC=2)=C1Cl NHBKIBNBSIWPJT-UHFFFAOYSA-N 0.000 claims 1
- JJPSYQJJXRJNJP-UHFFFAOYSA-N 1-(4-fluorobenzoyl)-9b-(4-methoxyphenyl)-2,3-dihydroimidazo[4,5]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(OC)=CC=C1C1(C2=CC=NC=C2C2=O)N2CCN1C(=O)C1=CC=C(F)C=C1 JJPSYQJJXRJNJP-UHFFFAOYSA-N 0.000 claims 1
- YMBGZMVIOKLNGJ-UHFFFAOYSA-N 1-(4-fluorobenzoyl)-9b-(4-methylphenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(C)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CC=C(F)C=C1 YMBGZMVIOKLNGJ-UHFFFAOYSA-N 0.000 claims 1
- INGNFBUVSOGHTB-UHFFFAOYSA-N 1-(4-fluorobenzoyl)-9b-(4-methylphenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-b]pyridazin-5-one Chemical compound C1=CC(C)=CC=C1C1(C2=CN=NC=C2C2=O)N2CCN1C(=O)C1=CC=C(F)C=C1 INGNFBUVSOGHTB-UHFFFAOYSA-N 0.000 claims 1
- LPCSEEYLDGTVBU-UHFFFAOYSA-N 1-(4-fluorobenzoyl)-9b-[4-(trifluoromethyl)phenyl]-2,3-dihydroimidazo[4,5]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(F)=CC=C1C(=O)N1C2(C=3C=CC(=CC=3)C(F)(F)F)C3=CC=NC=C3C(=O)N2CC1 LPCSEEYLDGTVBU-UHFFFAOYSA-N 0.000 claims 1
- WUPSLOPKAYMRIJ-UHFFFAOYSA-N 1-(5-bromo-4-methoxythiophene-3-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound COC1=C(Br)SC=C1C(=O)N1C2(C=3C=CC(Cl)=CC=3)C3=CN=CC=C3C(=O)N2CC1 WUPSLOPKAYMRIJ-UHFFFAOYSA-N 0.000 claims 1
- KKHXFRVASGHBNR-UHFFFAOYSA-N 1-(5-bromopyridine-3-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CN=CC(Br)=C1 KKHXFRVASGHBNR-UHFFFAOYSA-N 0.000 claims 1
- JQTKABJJRAEVNF-UHFFFAOYSA-N 1-(5-bromothiophene-2-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CC=C(Br)S1 JQTKABJJRAEVNF-UHFFFAOYSA-N 0.000 claims 1
- SKMPYELIJKSZGI-UHFFFAOYSA-N 1-(5-chloro-2-methylsulfanylpyrimidine-4-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound CSC1=NC=C(Cl)C(C(=O)N2C3(C4=CN=CC=C4C(=O)N3CC2)C=2C=CC(Cl)=CC=2)=N1 SKMPYELIJKSZGI-UHFFFAOYSA-N 0.000 claims 1
- SRFZFZOKKWPWSO-UHFFFAOYSA-N 1-(5-chloro-4-methoxythiophene-3-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound COC1=C(Cl)SC=C1C(=O)N1C2(C=3C=CC(Cl)=CC=3)C3=CN=CC=C3C(=O)N2CC1 SRFZFZOKKWPWSO-UHFFFAOYSA-N 0.000 claims 1
- WVQBBWDSEWDNKP-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylpyrazole-3-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C=1C=CC=CC=1N1N=C(C(C)(C)C)C=C1C(=O)N1CCN2C(=O)C3=CC=NC=C3C12C1=CC=C(Cl)C=C1 WVQBBWDSEWDNKP-UHFFFAOYSA-N 0.000 claims 1
- LOABQANRNDCVAY-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)acetyl]-9b-(4-methylphenyl)-2,3-dihydroimidazo[4,5]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(OC)=CC=C1CC(=O)N1C2(C=3C=CC(C)=CC=3)C3=CC=NC=C3C(=O)N2CC1 LOABQANRNDCVAY-UHFFFAOYSA-N 0.000 claims 1
- QDLIRWCTPXWMLZ-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)acetyl]-9b-[4-(trifluoromethyl)phenyl]-2,3-dihydroimidazo[4,5]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(OC)=CC=C1CC(=O)N1C2(C=3C=CC(=CC=3)C(F)(F)F)C3=CC=NC=C3C(=O)N2CC1 QDLIRWCTPXWMLZ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P31/14—Antivirals for RNA viruses
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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|---|---|---|---|
| AU2003907196A AU2003907196A0 (en) | 2003-12-24 | Polycyclic agents for the treatment of respiratory syncytial virus infections | |
| AU2003907196 | 2003-12-24 |
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| ES2360222T3 true ES2360222T3 (es) | 2011-06-02 |
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| EP (2) | EP1697377B1 (enExample) |
| JP (2) | JP5384793B2 (enExample) |
| KR (1) | KR20060127909A (enExample) |
| CN (2) | CN101723949B (enExample) |
| AT (1) | ATE496920T1 (enExample) |
| BR (1) | BRPI0418127A (enExample) |
| CA (1) | CA2551178C (enExample) |
| DE (1) | DE602004031258D1 (enExample) |
| ES (1) | ES2360222T3 (enExample) |
| IL (1) | IL176155A0 (enExample) |
| NO (1) | NO20062758L (enExample) |
| NZ (1) | NZ551468A (enExample) |
| RU (1) | RU2422444C2 (enExample) |
| WO (1) | WO2005061513A1 (enExample) |
| ZA (1) | ZA200604528B (enExample) |
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| JP5384793B2 (ja) | 2003-12-24 | 2014-01-08 | バイオウタ サイエンティフィック マネジメント プロプライエタリー リミテッド | 呼吸器合胞体ウイルス感染の処置のための多環式薬剤 |
| AR058554A1 (es) * | 2005-12-20 | 2008-02-13 | Novartis Ag | Compuestos heterociclicos nitrogenados de 6 miembros sustituidos, metodos para su preparacion, composiciones farmaceuticas que los contienen y su uso en el tratamiento de enfermedades mediadas por mglur5. |
| JP2010501567A (ja) | 2006-08-24 | 2010-01-21 | ノバルティス アクチエンゲゼルシャフト | 代謝系、心血管系および他の障害の処置のためのステアロイル−ＣｏＡ不飽和化酵素（ＳＣＤ）阻害剤としての２−（ピラジン−２−イル）−チアゾールおよび２−（１Ｈ−ピラゾール−３−イル）チアゾール誘導体ならびに関連化合物 |
| BRPI0718509A2 (pt) | 2006-09-22 | 2015-09-29 | Novartis Ag | compostos orgânicos heterocíclicos |
| TWI423972B (zh) * | 2006-09-28 | 2014-01-21 | Biota Scient Management | 治療呼吸系融合細胞病毒感染之多環劑 |
| CA2672776A1 (en) | 2006-12-20 | 2008-06-26 | Novartis Ag | 2-substituted 5-membered heterocycles as scd inhibitors |
| TWI508968B (zh) * | 2010-02-08 | 2015-11-21 | Biota Scient Management | 用於治療呼吸道融合性病毒感染的化合物 |
| JP5878171B2 (ja) * | 2010-06-24 | 2016-03-08 | ギリアード サイエンシーズ， インコーポレイテッド | 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン |
| AU2015200638B2 (en) * | 2010-06-24 | 2016-11-10 | Gilead Sciences, Inc. | Pyrazolo [1, 5 -a] pyrimidines as antiviral agents |
| US8796303B2 (en) | 2010-11-26 | 2014-08-05 | Biota Scientific Management Pty Ltd. | Imidazo[2,1-G][1,7]naphthyridines for treating respiratory syncytial virus infections |
| US8871756B2 (en) * | 2011-08-11 | 2014-10-28 | Hoffmann-La Roche Inc. | Compounds for the treatment and prophylaxis of Respiratory Syncytial Virus disease |
| CN103748098B (zh) * | 2011-10-11 | 2016-06-29 | 弗·哈夫曼-拉罗切有限公司 | 用于治疗或预防呼吸道合胞病毒疾病的化合物 |
| MX342153B (es) * | 2011-10-11 | 2016-09-15 | Hoffmann La Roche | Compuestos para el tratamiento y profilaxis de enfermedad por el virus sincitial respiratorio. |
| GB201119538D0 (en) * | 2011-11-10 | 2011-12-21 | Viral Ltd | Pharmaceutical compounds |
| EP2794611B1 (en) | 2011-12-22 | 2017-10-11 | Gilead Sciences, Inc. | Pyrazolo[1,5-a]pyrimidines as antiviral agents |
| HRP20191754T1 (hr) | 2012-04-17 | 2020-01-24 | Gilead Sciences, Inc. | Spojevi i postupci za antivirusno liječenje |
| CN104311559A (zh) * | 2014-09-12 | 2015-01-28 | 中山大学 | 一类光学纯手性环状n,n-缩醛的合成方法 |
| WO2016057931A1 (en) | 2014-10-10 | 2016-04-14 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| WO2016133888A1 (en) * | 2015-02-16 | 2016-08-25 | Biota Pharmaceuticals, Inc. | Compounds for treating respiratory syncytial virus infections |
| JO3637B1 (ar) | 2015-04-28 | 2020-08-27 | Janssen Sciences Ireland Uc | مركبات بيرازولو- وترايازولو- بيريميدين مضادة للفيروسات rsv |
| JP6749343B2 (ja) | 2015-05-20 | 2020-09-02 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 脊髄性筋萎縮症を処置するための化合物 |
| CN108290882B (zh) | 2015-07-16 | 2021-07-06 | 豪夫迈·罗氏有限公司 | 用于治疗呼吸道合胞病毒感染的4-喹唑啉胺衍生物的晶形 |
| KR102162062B1 (ko) | 2015-11-12 | 2020-10-07 | 에프. 호프만-라 로슈 아게 | 척수성 근위축증의 치료용 조성물 |
| EP3386978B1 (en) | 2015-12-10 | 2021-01-27 | H. Hoffnabb-La Roche Ag | Bridged piperidine derivatives |
| CN113750101A (zh) | 2015-12-10 | 2021-12-07 | Ptc医疗公司 | 用于治疗亨廷顿病的方法 |
| WO2017196970A1 (en) * | 2016-05-10 | 2017-11-16 | Georgia State University Research Foundation, Inc. | Heterocyclic derivatives for the thratment of rsv |
| US11407753B2 (en) | 2017-06-05 | 2022-08-09 | Ptc Therapeutics, Inc. | Compounds for treating Huntington's disease |
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| EP3645121B8 (en) | 2017-06-28 | 2025-06-18 | PTC Therapeutics, Inc. | Methods for treating huntington's disease |
| CA3067591A1 (en) | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | Methods for treating huntington's disease |
| TW201932470A (zh) | 2017-11-29 | 2019-08-16 | 愛爾蘭商健生科學愛爾蘭無限公司 | 具有抗ｒｓｖ活性之吡唑并嘧啶 |
| EA202091835A1 (ru) | 2018-01-31 | 2020-10-20 | Янссен Сайенсиз Айрлэнд Анлимитед Компани | Замещенные циклоалкилом пиразолопиримидины, обладающие активностью против rsv |
| US11760701B2 (en) | 2018-02-27 | 2023-09-19 | The Research Foundation For The State University Of New Yrok | Difluoromethoxylation and trifluoromethoxylation compositions and methods for synthesizing same |
| KR20210005559A (ko) | 2018-03-27 | 2021-01-14 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료 화합물 |
| KR20210005569A (ko) | 2018-04-23 | 2021-01-14 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | Rsv에 대한 활성을 갖는 헤테로방향족 화합물 |
| WO2019233941A1 (en) | 2018-06-05 | 2019-12-12 | F. Hoffmann-La Roche Ag | Tetrahydro-1 h-pyrazino[2,1 -ajisoindolylquinoline compounds for the treatment of autoimmune disease |
| US11685746B2 (en) | 2018-06-27 | 2023-06-27 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating Huntington's disease |
| LT3814357T (lt) | 2018-06-27 | 2024-06-25 | Ptc Therapeutics, Inc. | Heterocikliniai ir heteroarilų junginiai, skirti hantingtono ligos gydymui |
| WO2020005877A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| CN108997354B (zh) * | 2018-08-08 | 2021-12-31 | 青岛大学附属医院 | 二氢嘧啶并异吲哚酮类化合物及其乳膏剂和在治疗高尿酸血症中的用途 |
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-
2004
- 2004-12-24 JP JP2006545846A patent/JP5384793B2/ja not_active Expired - Fee Related
- 2004-12-24 CN CN2009102585362A patent/CN101723949B/zh not_active Expired - Fee Related
- 2004-12-24 CN CN200480039049A patent/CN100582109C/zh not_active Expired - Fee Related
- 2004-12-24 BR BRPI0418127-1A patent/BRPI0418127A/pt not_active IP Right Cessation
- 2004-12-24 CA CA2551178A patent/CA2551178C/en not_active Expired - Fee Related
- 2004-12-24 EP EP04802131A patent/EP1697377B1/en not_active Expired - Lifetime
- 2004-12-24 US US10/585,230 patent/US8598193B2/en not_active Expired - Fee Related
- 2004-12-24 EP EP10177705A patent/EP2287167A1/en not_active Withdrawn
- 2004-12-24 AT AT04802131T patent/ATE496920T1/de not_active IP Right Cessation
- 2004-12-24 DE DE602004031258T patent/DE602004031258D1/de not_active Expired - Lifetime
- 2004-12-24 WO PCT/AU2004/001830 patent/WO2005061513A1/en not_active Ceased
- 2004-12-24 NZ NZ551468A patent/NZ551468A/en not_active IP Right Cessation
- 2004-12-24 RU RU2006126663/04A patent/RU2422444C2/ru not_active IP Right Cessation
- 2004-12-24 ES ES04802131T patent/ES2360222T3/es not_active Expired - Lifetime
- 2004-12-24 KR KR1020067014876A patent/KR20060127909A/ko not_active Ceased
-
2006
- 2006-06-02 ZA ZA200604528A patent/ZA200604528B/en unknown
- 2006-06-06 IL IL176155A patent/IL176155A0/en unknown
- 2006-06-13 NO NO20062758A patent/NO20062758L/no not_active Application Discontinuation
-
2012
- 2012-09-18 JP JP2012204388A patent/JP5536842B2/ja not_active Expired - Fee Related
-
2013
- 2013-10-24 US US14/062,780 patent/US20140051689A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN101723949A (zh) | 2010-06-09 |
| CA2551178C (en) | 2012-11-06 |
| JP2007516983A (ja) | 2007-06-28 |
| NO20062758L (no) | 2006-07-17 |
| KR20060127909A (ko) | 2006-12-13 |
| US20070287700A1 (en) | 2007-12-13 |
| RU2006126663A (ru) | 2008-01-27 |
| CN1898247A (zh) | 2007-01-17 |
| IL176155A0 (en) | 2006-10-05 |
| JP5384793B2 (ja) | 2014-01-08 |
| HK1088607A1 (en) | 2006-11-10 |
| ATE496920T1 (de) | 2011-02-15 |
| BRPI0418127A (pt) | 2007-04-27 |
| ZA200604528B (en) | 2007-06-27 |
| US20140051689A1 (en) | 2014-02-20 |
| US8598193B2 (en) | 2013-12-03 |
| JP5536842B2 (ja) | 2014-07-02 |
| JP2012246318A (ja) | 2012-12-13 |
| CA2551178A1 (en) | 2005-07-07 |
| NZ551468A (en) | 2010-05-28 |
| EP1697377B1 (en) | 2011-01-26 |
| CN101723949B (zh) | 2013-10-23 |
| CN100582109C (zh) | 2010-01-20 |
| EP1697377A4 (en) | 2008-03-19 |
| RU2422444C2 (ru) | 2011-06-27 |
| WO2005061513A1 (en) | 2005-07-07 |
| EP2287167A1 (en) | 2011-02-23 |
| DE602004031258D1 (de) | 2011-03-10 |
| EP1697377A1 (en) | 2006-09-06 |
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