JP2007532665A5 - - Google Patents
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- Publication number
- JP2007532665A5 JP2007532665A5 JP2007508496A JP2007508496A JP2007532665A5 JP 2007532665 A5 JP2007532665 A5 JP 2007532665A5 JP 2007508496 A JP2007508496 A JP 2007508496A JP 2007508496 A JP2007508496 A JP 2007508496A JP 2007532665 A5 JP2007532665 A5 JP 2007532665A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- formula
- hiv integrase
- compound
- integrase inhibitor
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 262
- 229940099797 HIV integrase inhibitor Drugs 0.000 claims 165
- 239000003084 hiv integrase inhibitor Substances 0.000 claims 165
- 125000000623 heterocyclic group Chemical group 0.000 claims 34
- 125000003107 substituted aryl group Chemical group 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 239000000651 prodrug Substances 0.000 claims 28
- 229940002612 prodrug Drugs 0.000 claims 28
- 125000001072 heteroaryl group Chemical group 0.000 claims 26
- 229910052799 carbon Inorganic materials 0.000 claims 23
- 125000000547 substituted alkyl group Chemical group 0.000 claims 22
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 19
- -1 polyethyleneoxy Polymers 0.000 claims 19
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 19
- 125000003342 alkenyl group Chemical group 0.000 claims 18
- 125000000304 alkynyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 17
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 15
- 125000006239 protecting group Chemical group 0.000 claims 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 13
- 229910019142 PO4 Inorganic materials 0.000 claims 12
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 150000003951 lactams Chemical class 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 12
- 239000010452 phosphate Substances 0.000 claims 12
- 229940124530 sulfonamide Drugs 0.000 claims 12
- 150000003456 sulfonamides Chemical class 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims 10
- 150000001408 amides Chemical class 0.000 claims 9
- 230000000694 effects Effects 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 9
- 150000002596 lactones Chemical class 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 8
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 125000004419 alkynylene group Chemical group 0.000 claims 8
- 125000005361 aryl sulfoxide group Chemical group 0.000 claims 8
- 125000005110 aryl thio group Chemical group 0.000 claims 8
- 150000001721 carbon Chemical group 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 150000002825 nitriles Chemical class 0.000 claims 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 6
- 125000004450 alkenylene group Chemical group 0.000 claims 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000005208 trialkylammonium group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 150000001540 azides Chemical class 0.000 claims 5
- 238000006467 substitution reaction Methods 0.000 claims 5
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 4
- 150000001350 alkyl halides Chemical class 0.000 claims 4
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 150000007942 carboxylates Chemical class 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 230000003834 intracellular effect Effects 0.000 claims 4
- 210000000265 leukocyte Anatomy 0.000 claims 4
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 150000003457 sulfones Chemical class 0.000 claims 4
- 150000003462 sulfoxides Chemical class 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 108010002459 HIV Integrase Proteins 0.000 claims 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical group O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 claims 3
- 239000002207 metabolite Substances 0.000 claims 3
- 208000030507 AIDS Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 2
- 150000001356 alkyl thiols Chemical class 0.000 claims 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- GZGZMAJKCUAIRS-UHFFFAOYSA-N piperazin-1-yl sulfamate Chemical compound NS(=O)(=O)ON1CCNCC1 GZGZMAJKCUAIRS-UHFFFAOYSA-N 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- HFHDGHOGHWXXDT-ZSOIEALJSA-N (z)-1-[5-[(4-fluorophenyl)methyl]furan-2-yl]-3-hydroxy-3-(1h-1,2,4-triazol-5-yl)prop-2-en-1-one Chemical compound N=1C=NNC=1C(/O)=C/C(=O)C(O1)=CC=C1CC1=CC=C(F)C=C1 HFHDGHOGHWXXDT-ZSOIEALJSA-N 0.000 claims 1
- QGCIARGIIYMTGU-PTNGSMBKSA-N (z)-4-(3-benzylphenyl)-4-hydroxy-2-oxobut-3-enoic acid Chemical compound OC(=O)C(=O)\C=C(/O)C1=CC=CC(CC=2C=CC=CC=2)=C1 QGCIARGIIYMTGU-PTNGSMBKSA-N 0.000 claims 1
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims 1
- 101710101148 Probable 6-oxopurine nucleoside phosphorylase Proteins 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- 102000030764 Purine-nucleoside phosphorylase Human genes 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000006323 alkenyl amino group Chemical group 0.000 claims 1
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000006319 alkynyl amino group Chemical group 0.000 claims 1
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical class O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000004030 hiv protease inhibitor Substances 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000002519 immonomodulatory effect Effects 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000013160 medical therapy Methods 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims 1
- 239000002777 nucleoside Substances 0.000 claims 1
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 1
- 239000002773 nucleotide Substances 0.000 claims 1
- 125000003729 nucleotide group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 230000008685 targeting Effects 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims 1
- 0 C[C@](CCC1(C(C)(C)O)OC1)[C@@]1[C@]([C@]([C@@](C2=C3CCC(C(C)(C)[C@]4*)[C@]2(C)C[C@]4O*)O)O)(C(C)=O)C3=CC1 Chemical compound C[C@](CCC1(C(C)(C)O)OC1)[C@@]1[C@]([C@]([C@@](C2=C3CCC(C(C)(C)[C@]4*)[C@]2(C)C[C@]4O*)O)O)(C(C)=O)C3=CC1 0.000 description 26
- CDRSBPYJKRZQAY-UHFFFAOYSA-N COC(N1CCOCC1)=O Chemical compound COC(N1CCOCC1)=O CDRSBPYJKRZQAY-UHFFFAOYSA-N 0.000 description 1
- BVCPOBBMOIJWQM-UHFFFAOYSA-N COS(N1CCOCC1)(=O)=O Chemical compound COS(N1CCOCC1)(=O)=O BVCPOBBMOIJWQM-UHFFFAOYSA-N 0.000 description 1
- WXSIWFBRRFAVJQ-UHFFFAOYSA-N O=C(CC1CC1)N1CCOCC1 Chemical compound O=C(CC1CC1)N1CCOCC1 WXSIWFBRRFAVJQ-UHFFFAOYSA-N 0.000 description 1
- PVBOVFLECGDSBT-UHFFFAOYSA-N O=C(c(cccc1)c1S)NNC(c1ccccc1SSc(cc(cc1)I)c1C(NNC(c(cccc1)c1S)=O)=O)=O Chemical compound O=C(c(cccc1)c1S)NNC(c1ccccc1SSc(cc(cc1)I)c1C(NNC(c(cccc1)c1S)=O)=O)=O PVBOVFLECGDSBT-UHFFFAOYSA-N 0.000 description 1
- UXDSBDGMFUNUCO-UHFFFAOYSA-N O=C(c(cccc1)c1S)NNC(c1ccccc1SSc(cccc1)c1C(NNC(c(c([AlH2])ccc1)c1S)=O)=O)=O Chemical compound O=C(c(cccc1)c1S)NNC(c1ccccc1SSc(cccc1)c1C(NNC(c(c([AlH2])ccc1)c1S)=O)=O)=O UXDSBDGMFUNUCO-UHFFFAOYSA-N 0.000 description 1
- ATIQTVUVGCQYEV-UHFFFAOYSA-N O=C(c(cccc1)c1SSc(cccc1)c1C(NNC(c(ccc(I)c1)c1SSc1c2cccc1)=O)=O)NNC2=O Chemical compound O=C(c(cccc1)c1SSc(cccc1)c1C(NNC(c(ccc(I)c1)c1SSc1c2cccc1)=O)=O)NNC2=O ATIQTVUVGCQYEV-UHFFFAOYSA-N 0.000 description 1
- QHZMUUXGGURBEN-UHFFFAOYSA-M OC(C1OC(c(cc2O)cc(O[AlH2])c2O)=O)C(O)OC1OC1=C(c(cc2)cc(O)c2O)Oc2cc(O)cc(O)c2C1=O Chemical compound OC(C1OC(c(cc2O)cc(O[AlH2])c2O)=O)C(O)OC1OC1=C(c(cc2)cc(O)c2O)Oc2cc(O)cc(O)c2C1=O QHZMUUXGGURBEN-UHFFFAOYSA-M 0.000 description 1
- BHSGUMGKESMLOG-UHFFFAOYSA-N OC(c(cc1O)cc(O)c1O)OC(C1O)C(OC(C(c2c(cc3O)O)=O)=C(C(CC4O)=CC=C4O)Oc2c3[AlH2])OC1O Chemical compound OC(c(cc1O)cc(O)c1O)OC(C1O)C(OC(C(c2c(cc3O)O)=O)=C(C(CC4O)=CC=C4O)Oc2c3[AlH2])OC1O BHSGUMGKESMLOG-UHFFFAOYSA-N 0.000 description 1
- ARMGDESJBVCPBB-UHFFFAOYSA-N OC(c(cc1O)cc(O)c1O)OC(C1O)C(OC2=C(c(cc3)cc(O)c3O)Oc3cc(O)cc(O)c3C2=O)OC1O Chemical compound OC(c(cc1O)cc(O)c1O)OC(C1O)C(OC2=C(c(cc3)cc(O)c3O)Oc3cc(O)cc(O)c3C2=O)OC1O ARMGDESJBVCPBB-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56267804P | 2004-04-14 | 2004-04-14 | |
| PCT/US2005/012520 WO2005117904A2 (en) | 2004-04-14 | 2005-04-11 | Phosphonate analogs of hiv integrase inhibitor compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007532665A JP2007532665A (ja) | 2007-11-15 |
| JP2007532665A5 true JP2007532665A5 (https=) | 2008-06-19 |
Family
ID=35276373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007508496A Pending JP2007532665A (ja) | 2004-04-14 | 2005-04-11 | Ｈｉｖインテグラーゼ阻害剤化合物のホスホネート類似物 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20080076738A1 (https=) |
| EP (1) | EP1742642B1 (https=) |
| JP (1) | JP2007532665A (https=) |
| AT (1) | ATE411030T1 (https=) |
| AU (1) | AU2005249363A1 (https=) |
| CA (1) | CA2562713A1 (https=) |
| DE (1) | DE602005010413D1 (https=) |
| DK (1) | DK1742642T3 (https=) |
| ES (1) | ES2315922T3 (https=) |
| PL (1) | PL1742642T3 (https=) |
| PT (1) | PT1742642E (https=) |
| SI (1) | SI1742642T1 (https=) |
| WO (1) | WO2005117904A2 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040157804A1 (en) * | 2002-10-16 | 2004-08-12 | Gilead Sciences, Inc. | Pre-organized tricyclic integrase inhibitor compounds |
| TW200716632A (en) * | 2005-05-16 | 2007-05-01 | Gilead Sciences Inc | Integrase inhibitor compounds |
| US8013159B2 (en) | 2005-05-19 | 2011-09-06 | Merck Canada Inc. | Quinoline derivatives as EP4 antagonists |
| CA2616314A1 (en) * | 2005-07-27 | 2007-02-01 | Gilead Sciences, Inc. | Antiviral phosphonate conjugates for inhibition of hiv |
| WO2007096896A1 (en) * | 2006-02-20 | 2007-08-30 | Alembic Limited | An improved process for the preparation of biphosphonic derivatives |
| NZ572367A (en) * | 2006-05-16 | 2011-09-30 | Gilead Sciences Inc | Fused cyclic compounds as integrase inhibitors |
| WO2009026206A1 (en) * | 2007-08-21 | 2009-02-26 | University Of Toledo | Method for synthesizing xanthohumol |
| US20090291921A1 (en) * | 2007-11-20 | 2009-11-26 | Gilead Sciences, Inc. | Integrase inhibitors |
| WO2010011815A1 (en) * | 2008-07-25 | 2010-01-28 | Smithkline Beecham Corporation | Chemical compounds |
| EP2320909B8 (en) | 2008-07-25 | 2016-03-30 | VIIV Healthcare Company | Chemical compounds |
| SI2320908T1 (sl) * | 2008-07-25 | 2014-05-30 | Viiv Healthcare Company | Predzdravila dolutegravirja |
| CA2744019C (en) | 2008-12-11 | 2017-03-14 | Shionogi & Co., Ltd. | Synthesis of carbamoylpyridone hiv integrase inhibitors and intermediates |
| TWI518084B (zh) | 2009-03-26 | 2016-01-21 | 鹽野義製藥股份有限公司 | 哌喃酮與吡啶酮衍生物之製造方法 |
| PE20121524A1 (es) * | 2010-01-27 | 2012-12-03 | Viiv Healthcare Co | Combinaciones de compuestos que comprenden inhibidores de la integrasa de vih y otros agentes terapeuticos |
| TWI582097B (zh) | 2010-03-23 | 2017-05-11 | Ｖｉｉｖ醫療保健公司 | 製備胺甲醯吡啶酮衍生物及中間體之方法 |
| US20120142701A1 (en) * | 2010-05-28 | 2012-06-07 | The University Of Hong Kong | Compounds and methods for the treatment of proliferative diseases |
| GB2497476B (en) * | 2010-09-06 | 2018-01-10 | Guangzhou Inst Biomed & Health | Amide Compounds |
| EP2691393B1 (en) | 2011-03-31 | 2016-09-14 | Pfizer Inc | Novel bicyclic pyridinones |
| KR101365849B1 (ko) * | 2012-03-28 | 2014-02-24 | 경동제약 주식회사 | 솔리페나신 또는 그의 염의 제조방법 및 이에 사용되는 신규 중간체 |
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| EP0481214B1 (en) * | 1990-09-14 | 1998-06-24 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Prodrugs of phosphonates |
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-
2005
- 2005-04-11 EP EP05804767A patent/EP1742642B1/en not_active Expired - Lifetime
- 2005-04-11 AU AU2005249363A patent/AU2005249363A1/en not_active Abandoned
- 2005-04-11 CA CA002562713A patent/CA2562713A1/en not_active Abandoned
- 2005-04-11 ES ES05804767T patent/ES2315922T3/es not_active Expired - Lifetime
- 2005-04-11 AT AT05804767T patent/ATE411030T1/de not_active IP Right Cessation
- 2005-04-11 PL PL05804767T patent/PL1742642T3/pl unknown
- 2005-04-11 DK DK05804767T patent/DK1742642T3/da active
- 2005-04-11 SI SI200530545T patent/SI1742642T1/sl unknown
- 2005-04-11 WO PCT/US2005/012520 patent/WO2005117904A2/en not_active Ceased
- 2005-04-11 PT PT05804767T patent/PT1742642E/pt unknown
- 2005-04-11 DE DE602005010413T patent/DE602005010413D1/de not_active Expired - Fee Related
- 2005-04-11 US US11/578,649 patent/US20080076738A1/en not_active Abandoned
- 2005-04-11 JP JP2007508496A patent/JP2007532665A/ja active Pending
- 2005-04-14 US US11/106,363 patent/US20060116356A1/en not_active Abandoned
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