AU2007275689A1 - AZA-peptide protease inhibitors - Google Patents
AZA-peptide protease inhibitors Download PDFInfo
- Publication number
- AU2007275689A1 AU2007275689A1 AU2007275689A AU2007275689A AU2007275689A1 AU 2007275689 A1 AU2007275689 A1 AU 2007275689A1 AU 2007275689 A AU2007275689 A AU 2007275689A AU 2007275689 A AU2007275689 A AU 2007275689A AU 2007275689 A1 AU2007275689 A1 AU 2007275689A1
- Authority
- AU
- Australia
- Prior art keywords
- substituted
- heterocyclyl
- tla
- aryl
- tlb
- 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.)
- Abandoned
Links
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title claims description 6
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 353
- 150000001875 compounds Chemical class 0.000 claims description 319
- 125000003118 aryl group Chemical group 0.000 claims description 281
- 125000002947 alkylene group Chemical group 0.000 claims description 237
- 125000000217 alkyl group Chemical group 0.000 claims description 223
- 239000000651 prodrug Substances 0.000 claims description 175
- 229940002612 prodrug Drugs 0.000 claims description 175
- -1 cyano, formyl Chemical group 0.000 claims description 123
- 229910052760 oxygen Inorganic materials 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- 125000001072 heteroaryl group Chemical group 0.000 claims description 81
- 239000003112 inhibitor Substances 0.000 claims description 81
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 78
- 229910052757 nitrogen Inorganic materials 0.000 claims description 76
- 229910052799 carbon Inorganic materials 0.000 claims description 60
- 229910052717 sulfur Inorganic materials 0.000 claims description 53
- 125000003107 substituted aryl group Chemical group 0.000 claims description 47
- 125000006239 protecting group Chemical group 0.000 claims description 43
- 125000001188 haloalkyl group Chemical group 0.000 claims description 39
- 125000000304 alkynyl group Chemical group 0.000 claims description 36
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 34
- 229910020008 S(O) Inorganic materials 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 30
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 30
- LXRNKYYBEZMYNM-ACIOBRDBSA-N (4r)-3-[(2s,3s)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylbutanoyl]-5,5-dimethyl-n-prop-2-enyl-1,3-thiazolidine-4-carboxamide Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)C(=O)N1[C@@H](C(C)(C)SC1)C(=O)NCC=C)CC1=CC=CC=C1 LXRNKYYBEZMYNM-ACIOBRDBSA-N 0.000 claims description 28
- 150000001721 carbon Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims description 21
- 229940079593 drug Drugs 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000002777 nucleoside Substances 0.000 claims description 20
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 18
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 13
- 125000004450 alkenylene group Chemical group 0.000 claims description 13
- 125000004419 alkynylene group Chemical group 0.000 claims description 13
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 12
- 108010010369 HIV Protease Proteins 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 10
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 10
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 10
- 229940099797 HIV integrase inhibitor Drugs 0.000 claims description 10
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims description 10
- 108010007843 NADH oxidase Proteins 0.000 claims description 10
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000003084 hiv integrase inhibitor Substances 0.000 claims description 10
- 239000002773 nucleotide Substances 0.000 claims description 10
- 125000003729 nucleotide group Chemical group 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 229940124784 gp41 inhibitor Drugs 0.000 claims description 8
- JHXLLEDIXXOJQD-WELGVCPWSA-N (2-decoxy-3-dodecylsulfanylpropyl) [(2r,3s,5r)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate Chemical compound C1[C@H](F)[C@@H](COP(O)(=O)OCC(CSCCCCCCCCCCCC)OCCCCCCCCCC)O[C@H]1N1C(=O)NC(=O)C(C)=C1 JHXLLEDIXXOJQD-WELGVCPWSA-N 0.000 claims description 7
- 208000031886 HIV Infections Diseases 0.000 claims description 7
- 239000004030 hiv protease inhibitor Substances 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 208000037357 HIV infectious disease Diseases 0.000 claims description 5
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 108091005804 Peptidases Proteins 0.000 claims description 3
- 239000004365 Protease Substances 0.000 claims description 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 102100034343 Integrase Human genes 0.000 claims 10
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 claims 10
- XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 claims 9
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims 9
- KYRSNWPSSXSNEP-ZRTHHSRSSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one Chemical compound NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 KYRSNWPSSXSNEP-ZRTHHSRSSA-N 0.000 claims 6
- KRZBCHWVBQOTNZ-PSEXTPKNSA-N 3,5-di-O-caffeoyl quinic acid Chemical compound O([C@@H]1C[C@](O)(C[C@H]([C@@H]1O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 KRZBCHWVBQOTNZ-PSEXTPKNSA-N 0.000 claims 6
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims 6
- HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical group Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 claims 6
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims 6
- RLAHNGKRJJEIJL-RFZPGFLSSA-N [(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CO[C@@H](CO)O1 RLAHNGKRJJEIJL-RFZPGFLSSA-N 0.000 claims 6
- 229950005846 amdoxovir Drugs 0.000 claims 6
- YDDGKXBLOXEEMN-IABMMNSOSA-N chicoric acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-IABMMNSOSA-N 0.000 claims 6
- 229960005107 darunavir Drugs 0.000 claims 6
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims 6
- 229960003804 efavirenz Drugs 0.000 claims 6
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims 6
- 229960000366 emtricitabine Drugs 0.000 claims 6
- 229960005386 ipilimumab Drugs 0.000 claims 6
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims 6
- SWUARLUWKZWEBQ-VQHVLOKHSA-N phenethyl caffeate Chemical compound C1=C(O)C(O)=CC=C1\C=C\C(=O)OCCC1=CC=CC=C1 SWUARLUWKZWEBQ-VQHVLOKHSA-N 0.000 claims 6
- 229960004742 raltegravir Drugs 0.000 claims 6
- CZFFBEXEKNGXKS-UHFFFAOYSA-N raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 claims 6
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 6
- GIXWDMTZECRIJT-UHFFFAOYSA-N aurintricarboxylic acid Chemical class C1=CC(=O)C(C(=O)O)=CC1=C(C=1C=C(C(O)=CC=1)C(O)=O)C1=CC=C(O)C(C(O)=O)=C1 GIXWDMTZECRIJT-UHFFFAOYSA-N 0.000 claims 5
- NIDRYBLTWYFCFV-FMTVUPSXSA-N (+)-calanolide A Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-FMTVUPSXSA-N 0.000 claims 3
- IXZYCIFRVZKVRJ-RKKDRKJOSA-N (2s)-n-[(2s,3r)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-[[2-[(3-fluorophenyl)methylamino]acetyl]amino]-3,3-dimethylbutanamide Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)[C@@H](NC(=O)CNCC=1C=C(F)C=CC=1)C(C)(C)C)C1=CC=CC=C1 IXZYCIFRVZKVRJ-RKKDRKJOSA-N 0.000 claims 3
- JLUPGSPHOGFEOB-WQLSENKSSA-N (2z)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)-n-[(4-fluorophenyl)methyl]-n-methoxyacetamide Chemical compound O\1C(C)(C)OC(=O)C/1=C/C(=O)N(OC)CC1=CC=C(F)C=C1 JLUPGSPHOGFEOB-WQLSENKSSA-N 0.000 claims 3
- CWVMWSZEMZOUPC-JUAXIXHSSA-N (3s,5s,8r,9s,10s,13s,14s,16r)-16-bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical group C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C([C@H](Br)C4)=O)[C@@H]4[C@@H]3CC[C@H]21 CWVMWSZEMZOUPC-JUAXIXHSSA-N 0.000 claims 3
- CNPVJJQCETWNEU-CYFREDJKSA-N (4,6-dimethyl-5-pyrimidinyl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]methanone Chemical compound N([C@@H](COC)C=1C=CC(=CC=1)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C CNPVJJQCETWNEU-CYFREDJKSA-N 0.000 claims 3
- QCNJQJJFXFJVCX-ZDUSSCGKSA-N (4s)-4-(2-cyclopropylethynyl)-5,6-difluoro-4-(trifluoromethyl)-1,3-dihydroquinazolin-2-one Chemical compound C([C@@]1(NC(=O)NC2=CC=C(C(=C21)F)F)C(F)(F)F)#CC1CC1 QCNJQJJFXFJVCX-ZDUSSCGKSA-N 0.000 claims 3
- JJWJSIAJLBEMEN-ZDUSSCGKSA-N (4s)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1,3-dihydroquinazolin-2-one Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)N1)C(F)(F)F)#CC1CC1 JJWJSIAJLBEMEN-ZDUSSCGKSA-N 0.000 claims 3
- UXDWYQAXEGVSPS-GFUIURDCSA-N (4s)-6-chloro-4-[(e)-2-cyclopropylethenyl]-4-(trifluoromethyl)-1,3-dihydroquinazolin-2-one Chemical compound C(/[C@]1(C2=CC(Cl)=CC=C2NC(=O)N1)C(F)(F)F)=C\C1CC1 UXDWYQAXEGVSPS-GFUIURDCSA-N 0.000 claims 3
- DBPMWRYLTBNCCE-UHFFFAOYSA-N 1-(4-benzoylpiperazin-1-yl)-2-(4,7-dimethoxy-1h-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione Chemical group C1=2C(OC)=CN=C(OC)C=2NC=C1C(=O)C(=O)N(CC1)CCN1C(=O)C1=CC=CC=C1 DBPMWRYLTBNCCE-UHFFFAOYSA-N 0.000 claims 3
- NKPHEWJJTGPRSL-OCCSQVGLSA-N 1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea Chemical compound CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O NKPHEWJJTGPRSL-OCCSQVGLSA-N 0.000 claims 3
- BEMBRAMZGVDPMH-UHFFFAOYSA-N 11-ethyl-5-methyl-8-[2-(1-oxidoquinolin-1-ium-4-yl)oxyethyl]dipyrido[2,3-d:2',3'-h][1,4]diazepin-6-one Chemical compound CN1C(=O)C2=CC(CCOC=3C4=CC=CC=C4[N+]([O-])=CC=3)=CN=C2N(CC)C2=NC=CC=C21 BEMBRAMZGVDPMH-UHFFFAOYSA-N 0.000 claims 3
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- A61P31/18—Antivirals for RNA viruses for HIV
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2013267072A AU2013267072A1 (en) | 2006-07-21 | 2013-12-06 | Aza-peptide protease inhibitors |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US83245906P | 2006-07-21 | 2006-07-21 | |
| US60/832,459 | 2006-07-21 | ||
| PCT/US2007/016397 WO2008011116A2 (en) | 2006-07-21 | 2007-07-19 | Aza-peptide protease inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| AU2013267072A Division AU2013267072A1 (en) | 2006-07-21 | 2013-12-06 | Aza-peptide protease inhibitors |
Publications (1)
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| AU2007275689A1 true AU2007275689A1 (en) | 2008-01-24 |
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| AU2007275689A Abandoned AU2007275689A1 (en) | 2006-07-21 | 2007-07-19 | AZA-peptide protease inhibitors |
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| US (1) | US7741345B2 (enExample) |
| EP (1) | EP2049547A2 (enExample) |
| JP (2) | JP5372751B2 (enExample) |
| AU (1) | AU2007275689A1 (enExample) |
| CA (1) | CA2657821A1 (enExample) |
| NZ (1) | NZ573888A (enExample) |
| WO (1) | WO2008011116A2 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20140031250A1 (en) | 2010-10-07 | 2014-01-30 | David Tsai Ting | Biomarkers of Cancer |
| EP2764002B1 (en) | 2012-10-03 | 2018-02-28 | Gilead Sciences, Inc. | Methods for preparing anti-viral nucleotide analogs |
| WO2015157623A1 (en) | 2014-04-11 | 2015-10-15 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Immune gene signatures in urothelial carcinoma (uc) |
| EP3142659B1 (en) * | 2014-05-16 | 2021-03-24 | Purdue Research Foundation | Hiv-1 protease inhibitors and uses thereof |
| EP3760208B1 (en) | 2014-06-25 | 2024-05-29 | The General Hospital Corporation | Targeting human satellite ii (hsatii) |
| CN104356054B (zh) * | 2014-09-30 | 2017-04-19 | 东北制药集团股份有限公司 | 一种制备阿扎那韦单体的方法 |
| US9724395B2 (en) | 2014-10-21 | 2017-08-08 | Sciclone Pharmaceuticals, Inc. | Treatment of cancer with immune stimulators |
| CN118286245A (zh) | 2014-12-26 | 2024-07-05 | 埃莫里大学 | N4-羟基胞苷和衍生物及与其相关的抗病毒用途 |
| US10034901B2 (en) | 2015-01-22 | 2018-07-31 | University Of Massachusetts | Cancer immunotherapy |
| CN108139375A (zh) | 2015-06-26 | 2018-06-08 | 贝斯以色列女执事医疗中心股份有限公司 | 靶向髓样衍生的抑制细胞中的四跨膜蛋白33(tspan33)的癌症疗法 |
| JP7178906B2 (ja) | 2016-05-19 | 2022-11-28 | ザ ジェネラル ホスピタル コーポレイション | ナチュラルキラー細胞および制御性Ｔ細胞の活性を強化するためのプラットフォームである、その受容体ＩＬ－２Ｒβに繋ぎ止められたインターロイキン－２ |
| EP3532638A4 (en) | 2016-10-31 | 2020-07-29 | University of Massachusetts | TARGETING MICROARN-101-3 P IN CARCINOTHERAPY |
| JOP20180009A1 (ar) | 2017-02-06 | 2019-01-30 | Gilead Sciences Inc | مركبات مثبط فيروس hiv |
| US11331331B2 (en) | 2017-12-07 | 2022-05-17 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| US11766455B2 (en) | 2017-12-14 | 2023-09-26 | Ezy Biotech Llc | Subject-specific tumor inhibiting cells and the use thereof |
| US11814623B2 (en) | 2018-01-30 | 2023-11-14 | University Of Massachusetts | Methods of treating a wound using epigenetic regulation |
| EP4317972A3 (en) | 2018-02-06 | 2024-03-13 | The General Hospital Corporation | Repeat rna as biomarkers of tumor immune response |
| TWI766172B (zh) * | 2018-07-30 | 2022-06-01 | 美商基利科學股份有限公司 | 抗hiv化合物 |
| EP3947640A4 (en) | 2019-04-02 | 2022-12-14 | The Brigham & Women's Hospital, Inc. | PROCEDURE FOR DETERMINING THE PROGRESSION OF PRIMARY MELANOMA |
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| US4816570A (en) * | 1982-11-30 | 1989-03-28 | The Board Of Regents Of The University Of Texas System | Biologically reversible phosphate and phosphonate protective groups |
| US4968788A (en) * | 1986-04-04 | 1990-11-06 | Board Of Regents, The University Of Texas System | Biologically reversible phosphate and phosphonate protective gruops |
| ES2118069T3 (es) * | 1990-09-14 | 1998-09-16 | Acad Of Science Czech Republic | Profarmacos de fosfonatos. |
| DK0521827T3 (da) * | 1991-07-03 | 1996-11-11 | Ciba Geigy Ag | Farmakologisk virksomme hydrazinderivater og fremgangsmåde til deres fremstilling |
| ES2093394T3 (es) * | 1992-12-23 | 1996-12-16 | Ciba Geigy Ag | Derivados de hidrazina antiretrovirales. |
| US5461067A (en) * | 1993-02-25 | 1995-10-24 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| WO1997046514A1 (en) * | 1996-05-31 | 1997-12-11 | Novartis Ag | Process for the preparation of hydrazine derivatives useful as intermediates for the preparation of peptide analogues |
| US20050239054A1 (en) | 2002-04-26 | 2005-10-27 | Arimilli Murty N | Method and compositions for identifying anti-HIV therapeutic compounds |
| US7339930B2 (en) | 2002-11-22 | 2008-03-04 | Sun Microsystems, Inc. | Method and apparatus for performing an address lookup using a multi-bit trie with backtracking |
| WO2005061487A1 (en) * | 2003-12-11 | 2005-07-07 | Abbott Laboratories | Hiv protease inhibiting compounds |
| EP1713470A1 (en) * | 2004-01-30 | 2006-10-25 | Pfizer, Inc. | Therapeutic combinations |
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2007
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- 2007-07-19 US US11/880,067 patent/US7741345B2/en active Active
- 2007-07-19 CA CA002657821A patent/CA2657821A1/en not_active Abandoned
- 2007-07-19 NZ NZ573888A patent/NZ573888A/en unknown
- 2007-07-19 EP EP07836151A patent/EP2049547A2/en not_active Withdrawn
- 2007-07-19 JP JP2009520841A patent/JP5372751B2/ja active Active
- 2007-07-19 AU AU2007275689A patent/AU2007275689A1/en not_active Abandoned
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2012
- 2012-11-21 JP JP2012255542A patent/JP2013056926A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NZ573888A (en) | 2012-02-24 |
| WO2008011116A3 (en) | 2008-04-24 |
| CA2657821A1 (en) | 2008-01-24 |
| EP2049547A2 (en) | 2009-04-22 |
| JP2009544612A (ja) | 2009-12-17 |
| US20090099096A1 (en) | 2009-04-16 |
| WO2008011116A2 (en) | 2008-01-24 |
| JP2013056926A (ja) | 2013-03-28 |
| JP5372751B2 (ja) | 2013-12-18 |
| US7741345B2 (en) | 2010-06-22 |
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Legal Events
| Date | Code | Title | Description |
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| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |