TW201014836A - Compounds for the treatment of hepatitis C - Google Patents
Compounds for the treatment of hepatitis C Download PDFInfo
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- TW201014836A TW201014836A TW098130829A TW98130829A TW201014836A TW 201014836 A TW201014836 A TW 201014836A TW 098130829 A TW098130829 A TW 098130829A TW 98130829 A TW98130829 A TW 98130829A TW 201014836 A TW201014836 A TW 201014836A
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- Prior art keywords
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- alkyl
- solvent
- phenyl
- minutes
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 128
- 238000011282 treatment Methods 0.000 title claims description 10
- 208000005176 Hepatitis C Diseases 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 276
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 197
- -1 oxycarbonylcarbonylamino Chemical group 0.000 claims description 158
- 229910052739 hydrogen Inorganic materials 0.000 claims description 112
- 125000001424 substituent group Chemical group 0.000 claims description 104
- 239000001257 hydrogen Substances 0.000 claims description 83
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 77
- 125000003545 alkoxy group Chemical group 0.000 claims description 72
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
- 150000001412 amines Chemical class 0.000 claims description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 46
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 40
- 125000004076 pyridyl group Chemical group 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000003277 amino group Chemical group 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 24
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 24
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 23
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 21
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 14
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000001425 triazolyl group Chemical group 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 10
- 125000002757 morpholinyl group Chemical class 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 8
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000005059 halophenyl group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 150000002923 oximes Chemical class 0.000 claims description 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
- 125000001725 pyrenyl group Chemical group 0.000 claims description 7
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 239000004098 Tetracycline Substances 0.000 claims description 5
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 229960002180 tetracycline Drugs 0.000 claims description 5
- 229930101283 tetracycline Natural products 0.000 claims description 5
- 235000019364 tetracycline Nutrition 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- 125000005265 dialkylamine group Chemical group 0.000 claims description 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 4
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 3
- 125000005095 alkynylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical group N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 206010039424 Salivary hypersecretion Diseases 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 208000026451 salivation Diseases 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- CZVXEAWVGZTLON-UHFFFAOYSA-N 1,1-dibenzylhydrazine Chemical group C=1C=CC=CC=1CN(N)CC1=CC=CC=C1 CZVXEAWVGZTLON-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- UKZJZMLGGSGZMI-UHFFFAOYSA-N 2,3,4,7,8,9-hexahydro-1h-purine Chemical compound N1CNC=C2NCNC21 UKZJZMLGGSGZMI-UHFFFAOYSA-N 0.000 claims 1
- 206010062717 Increased upper airway secretion Diseases 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- LOMMDWBTANPFEJ-UHFFFAOYSA-N acridin-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=NC2=C1 LOMMDWBTANPFEJ-UHFFFAOYSA-N 0.000 claims 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 1
- 229910052786 argon Inorganic materials 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000037429 base substitution Effects 0.000 claims 1
- XTOKBQLTBGASEX-UHFFFAOYSA-N benzene-1,4-diol;hydrazine Chemical compound NN.OC1=CC=C(O)C=C1 XTOKBQLTBGASEX-UHFFFAOYSA-N 0.000 claims 1
- MDLHEADEPQXWHI-UHFFFAOYSA-N benzene;furan Chemical compound C=1C=COC=1.C1=CC=CC=C1 MDLHEADEPQXWHI-UHFFFAOYSA-N 0.000 claims 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical class [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
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- DXVWRJRZCMCNEU-UHFFFAOYSA-N dimercaptoamine Chemical compound SNS DXVWRJRZCMCNEU-UHFFFAOYSA-N 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- DTGSFFWQUULHIF-UHFFFAOYSA-N imino-dimethyl-oxo-$l^{6}-sulfane Chemical compound CS(C)(=N)=O DTGSFFWQUULHIF-UHFFFAOYSA-N 0.000 claims 1
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- 150000002576 ketones Chemical class 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
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- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims 1
- 208000026435 phlegm Diseases 0.000 claims 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- 230000000276 sedentary effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 123
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- 239000002904 solvent Substances 0.000 description 688
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000002435 tendon Anatomy 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
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- 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
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- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Furan Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Peptides Or Proteins (AREA)
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| US8354410B2 (en) * | 2010-03-11 | 2013-01-15 | Bristol-Meyers Squibb Company | Compounds for the treatment of hepatitis C |
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| US8445497B2 (en) * | 2010-06-30 | 2013-05-21 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| MX341732B (es) | 2010-07-29 | 2016-08-30 | Oryzon Genomics S A * | Inhibidores de la demetilasa lsd1 basados en arilciclopropilamina y sus usos médicos. |
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| EP2616461A4 (en) | 2010-08-26 | 2014-03-26 | Rfs Pharma Llc | POTENTIVE AND SELECTIVE INHIBITORS OF HEPATITIS C VIRUS |
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| BR112013009789A2 (pt) | 2010-10-26 | 2016-07-19 | Presidio Pharmaceuticals Inc | inibidores do vírus da hepatite c |
| WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| US8507683B2 (en) * | 2010-12-09 | 2013-08-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| CA2822357A1 (en) * | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| EP3981395A1 (en) | 2011-02-08 | 2022-04-13 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| WO2013033901A1 (en) * | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases |
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| US9303020B2 (en) | 2012-02-08 | 2016-04-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US9096580B2 (en) | 2012-03-27 | 2015-08-04 | Bristol-Myers Squibb Company | Benzofuran derivatives for the treatment of hepatitis C |
| WO2013163466A1 (en) * | 2012-04-25 | 2013-10-31 | Presidio Pharmaceuticals, Inc. | Inhibitors of hepatitis c virus |
| US9169214B2 (en) | 2012-12-21 | 2015-10-27 | The Board Of Trustees Of The Leland Stanford Junior University | Compounds and compositions that bind and stabilize transthyretin and their use for inhibiting transthyretin amyloidosis and protein-protein interactions |
| EP2943496B1 (en) * | 2013-01-10 | 2017-09-06 | Bristol-Myers Squibb Company | Macrocyclic benzofuran and azabenzofuran compounds for the treatment of hepatitis c |
| WO2014121416A1 (en) | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| US8962651B2 (en) | 2013-03-13 | 2015-02-24 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US9738653B2 (en) | 2013-03-14 | 2017-08-22 | Bristol-Myers Squibb Company | Fused furans for the treatment of hepatitis C |
| WO2014205593A1 (en) * | 2013-06-24 | 2014-12-31 | Merck Sharp & Dohme Corp. | Substituted benzofuran compounds and methods of use thereof for treatment of viral diseases |
| EP3080106B1 (en) | 2013-12-13 | 2018-01-31 | Bristol-Myers Squibb Company | A novel compound for the treatment of hepatitis c |
| EP3119769A1 (en) * | 2014-03-21 | 2017-01-25 | Bristol-Myers Squibb Pharma Company | Cyanoamino (aza)benzofuran compounds for the treatment of hepatitis c |
| EA201691777A1 (ru) * | 2014-03-21 | 2016-12-30 | Бристол-Маерс Сквибб Компани | Содержащие цианогруппу соединения азабензофурана для лечения гепатита с |
| JP6543342B2 (ja) | 2014-08-14 | 2019-07-10 | アルハマドシャー,マモウン,エム. | 血清半減期を延長するための、調節可能リンカーを介した薬学的活性剤とトランスサイレチンリガンドのコンジュゲーション |
| WO2016133963A1 (en) * | 2015-02-19 | 2016-08-25 | Bristol-Myers Squibb Company | Benzofurans substituted with secondary benzamide as hcv inhibitors |
| WO2016133972A1 (en) * | 2015-02-19 | 2016-08-25 | Bristol-Myers Squibb Company | Substituted benzofuran compounds for the treatment of hepatitis c |
| WO2016133961A1 (en) * | 2015-02-19 | 2016-08-25 | Bristol-Myers Squibb Company | Benzofurans substituted with bicyclic secondary benzamide as hcv inhibitors |
| WO2016133970A1 (en) * | 2015-02-19 | 2016-08-25 | Bristol-Myers Squibb Company | Benzofurans substituted with primary benzamide as hcv inhibitors |
| WO2016137832A1 (en) * | 2015-02-23 | 2016-09-01 | Bristol-Myers Squibb Company | Novel compounds for the treatment of hepatitis c |
| US11161837B2 (en) | 2016-03-21 | 2021-11-02 | Bristol-Myers Squibb Company | Benzofuran derivatives for the treatment of hepatitis C |
| NZ755597A (en) | 2017-02-17 | 2023-06-30 | Eidos Therapeutics Inc | Processes for preparing ag-10, its intermediates, and salts thereof |
| KR102512548B1 (ko) | 2017-12-22 | 2023-03-22 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 함질소 화합물 |
| SG11202009073WA (en) | 2018-03-23 | 2020-10-29 | Eidos Therapeutics Inc | Methods of treating ttr amyloidosis using ag10 |
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| JPS57123181A (en) | 1981-01-23 | 1982-07-31 | Mitsubishi Paper Mills Ltd | Preparation of pyrazolo (1,5-a) pyridine derivative |
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
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| GB0707000D0 (en) | 2007-04-12 | 2007-05-30 | Istituto Di Ricerche D Biolog | Antiviral agents |
| CN101910145A (zh) | 2008-02-14 | 2010-12-08 | 弗·哈夫曼-拉罗切有限公司 | 抗病毒的杂环化合物 |
| WO2009137493A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 2-substituted benzofuran compounds to treat infection with hepatitis c virus |
| WO2009137500A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 6-substituted benzofuran compounds to treat infection with hepatitis c virus |
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2009
- 2009-09-04 US US12/554,193 patent/US8048887B2/en active Active
- 2009-09-08 NZ NZ591172A patent/NZ591172A/xx not_active IP Right Cessation
- 2009-09-08 CN CN200980144912.3A patent/CN102209717B/zh not_active Expired - Fee Related
- 2009-09-08 JP JP2011526931A patent/JP5685191B2/ja not_active Expired - Fee Related
- 2009-09-08 WO PCT/US2009/056166 patent/WO2010030592A1/en not_active Ceased
- 2009-09-08 BR BRPI0918174A patent/BRPI0918174A2/pt not_active IP Right Cessation
- 2009-09-08 EA EA201100390A patent/EA019185B1/ru not_active IP Right Cessation
- 2009-09-08 MX MX2011002410A patent/MX2011002410A/es active IP Right Grant
- 2009-09-08 KR KR1020117008085A patent/KR20110059875A/ko not_active Ceased
- 2009-09-08 PE PE2011000445A patent/PE20110806A1/es active IP Right Grant
- 2009-09-08 CA CA2736988A patent/CA2736988A1/en not_active Abandoned
- 2009-09-08 AU AU2009291966A patent/AU2009291966B2/en not_active Ceased
- 2009-09-08 EP EP09792299.1A patent/EP2326633B1/en not_active Not-in-force
- 2009-09-11 TW TW098130829A patent/TW201014836A/zh unknown
- 2009-09-11 AR ARP090103514A patent/AR073740A1/es not_active Application Discontinuation
- 2009-09-11 TW TW100113021A patent/TW201124403A/zh unknown
-
2011
- 2011-03-01 ZA ZA2011/01739A patent/ZA201101739B/en unknown
- 2011-03-01 IL IL211509A patent/IL211509A0/en unknown
- 2011-03-11 CL CL2011000527A patent/CL2011000527A1/es unknown
- 2011-04-05 CO CO11041979A patent/CO6382110A2/es not_active Application Discontinuation
- 2011-05-25 CL CL2011001224A patent/CL2011001224A1/es unknown
- 2011-08-03 ZA ZA2011/05720A patent/ZA201105720B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2326633A1 (en) | 2011-06-01 |
| CL2011000527A1 (es) | 2011-08-12 |
| TW201124403A (en) | 2011-07-16 |
| EA201100390A1 (ru) | 2011-10-31 |
| MX2011002410A (es) | 2011-04-05 |
| EP2326633B1 (en) | 2015-12-16 |
| CN102209717B (zh) | 2015-02-18 |
| CA2736988A1 (en) | 2010-03-18 |
| AU2009291966B2 (en) | 2014-08-28 |
| EA019185B1 (ru) | 2014-01-30 |
| NZ591172A (en) | 2012-12-21 |
| IL211509A0 (en) | 2011-07-31 |
| CN102209717A (zh) | 2011-10-05 |
| US20100093694A1 (en) | 2010-04-15 |
| ZA201101739B (en) | 2012-08-29 |
| AU2009291966A1 (en) | 2010-03-18 |
| BRPI0918174A2 (pt) | 2019-10-01 |
| ZA201105720B (en) | 2012-08-29 |
| CL2011001224A1 (es) | 2011-09-16 |
| PE20110806A1 (es) | 2011-10-31 |
| JP5685191B2 (ja) | 2015-03-18 |
| JP2012502101A (ja) | 2012-01-26 |
| US8048887B2 (en) | 2011-11-01 |
| WO2010030592A1 (en) | 2010-03-18 |
| KR20110059875A (ko) | 2011-06-07 |
| CO6382110A2 (es) | 2012-02-15 |
| AR073740A1 (es) | 2010-12-01 |
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