AU2015259173B2 - Hsp70 modulators and methods for making and using the same - Google Patents
Hsp70 modulators and methods for making and using the same Download PDFInfo
- Publication number
- AU2015259173B2 AU2015259173B2 AU2015259173A AU2015259173A AU2015259173B2 AU 2015259173 B2 AU2015259173 B2 AU 2015259173B2 AU 2015259173 A AU2015259173 A AU 2015259173A AU 2015259173 A AU2015259173 A AU 2015259173A AU 2015259173 B2 AU2015259173 B2 AU 2015259173B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- ring
- alkyl
- mhz
- nmr
- 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.)
- Ceased
Links
- 0 CN1CC(*)C1 Chemical compound CN1CC(*)C1 0.000 description 14
- ZZZRXGKTICQJAP-UHFFFAOYSA-N C#CCN(CC1)CCN1c(nc1OCc2cccc(Cl)c2)ncc1Sc(cc1C(F)(F)F)ccc1C#N Chemical compound C#CCN(CC1)CCN1c(nc1OCc2cccc(Cl)c2)ncc1Sc(cc1C(F)(F)F)ccc1C#N ZZZRXGKTICQJAP-UHFFFAOYSA-N 0.000 description 1
- CUVQEZIRSILQRS-UHFFFAOYSA-N C#CCN(CC1)CCN1c(nc1OCc2cccc(Cl)c2)ncc1Sc1ccc(C(N)=O)c(C(F)(F)F)c1 Chemical compound C#CCN(CC1)CCN1c(nc1OCc2cccc(Cl)c2)ncc1Sc1ccc(C(N)=O)c(C(F)(F)F)c1 CUVQEZIRSILQRS-UHFFFAOYSA-N 0.000 description 1
- AJFZGQPNNLDIQM-LNKIKWGQSA-N C/C(/COc1nc(N2CCNCC2)ncc1Sc(cc1)cnc1N)=C\C=C Chemical compound C/C(/COc1nc(N2CCNCC2)ncc1Sc(cc1)cnc1N)=C\C=C AJFZGQPNNLDIQM-LNKIKWGQSA-N 0.000 description 1
- PTYHVJFDGLJOFU-UHFFFAOYSA-N CC(C)(C1)N(C)CCN1c(nc1OCc2cccc(C)c2)ncc1Sc(cc1)ccc1C#N Chemical compound CC(C)(C1)N(C)CCN1c(nc1OCc2cccc(C)c2)ncc1Sc(cc1)ccc1C#N PTYHVJFDGLJOFU-UHFFFAOYSA-N 0.000 description 1
- PDLCCNYKIIUWHA-UHFFFAOYSA-N CC(C)c(cc1)ccc1C(C)=O Chemical compound CC(C)c(cc1)ccc1C(C)=O PDLCCNYKIIUWHA-UHFFFAOYSA-N 0.000 description 1
- MLXDAOFCUKUYQP-UHFFFAOYSA-N CC(C)c1ccc(C(N)=O)c(F)c1 Chemical compound CC(C)c1ccc(C(N)=O)c(F)c1 MLXDAOFCUKUYQP-UHFFFAOYSA-N 0.000 description 1
- YVRXGIACHNLZCV-GOSISDBHSA-N CC(c(cc1)ccc1Sc1cnc(N(CC2)C[C@@H]2NC)nc1OCc1cc(N)ncc1)=O Chemical compound CC(c(cc1)ccc1Sc1cnc(N(CC2)C[C@@H]2NC)nc1OCc1cc(N)ncc1)=O YVRXGIACHNLZCV-GOSISDBHSA-N 0.000 description 1
- CDRHURWXGOLMEI-JXMROGBWSA-N CCOC(/C=C/c(cc1)ccc1C(OCC)=O)=O Chemical compound CCOC(/C=C/c(cc1)ccc1C(OCC)=O)=O CDRHURWXGOLMEI-JXMROGBWSA-N 0.000 description 1
- XFJORYJXGYFUCY-UHFFFAOYSA-N CCOC(C(Cc(cc1)ccc1C(OCC)=O)C=O)=O Chemical compound CCOC(C(Cc(cc1)ccc1C(OCC)=O)C=O)=O XFJORYJXGYFUCY-UHFFFAOYSA-N 0.000 description 1
- OYMFFRUCMOQDON-UHFFFAOYSA-N CCOC(CCc(cc1)ccc1C(OCC)=O)=O Chemical compound CCOC(CCc(cc1)ccc1C(OCC)=O)=O OYMFFRUCMOQDON-UHFFFAOYSA-N 0.000 description 1
- SWQFPRDHVYGYBA-UHFFFAOYSA-N CCOC(COc(cc1)ccc1C#N)=C Chemical compound CCOC(COc(cc1)ccc1C#N)=C SWQFPRDHVYGYBA-UHFFFAOYSA-N 0.000 description 1
- VGQWAZLAYNRZEE-UHFFFAOYSA-N CCc1cc(COc2nc(N3CCN(C)CC3)ncc2Sc(cc2C(F)(F)F)ccc2C#N)ccc1 Chemical compound CCc1cc(COc2nc(N3CCN(C)CC3)ncc2Sc(cc2C(F)(F)F)ccc2C#N)ccc1 VGQWAZLAYNRZEE-UHFFFAOYSA-N 0.000 description 1
- IZRMJQMKVULXCP-UHFFFAOYSA-N CN(C)C(CC1)CN1c(nc1O)ncc1Sc(cc1)cnc1N Chemical compound CN(C)C(CC1)CN1c(nc1O)ncc1Sc(cc1)cnc1N IZRMJQMKVULXCP-UHFFFAOYSA-N 0.000 description 1
- PEXJKRSJDMUVBX-UHFFFAOYSA-N CN(C)C(CC1)CN1c(nc1OCc2cc(Cl)ccc2)ncc1Sc(cc1)cnc1N Chemical compound CN(C)C(CC1)CN1c(nc1OCc2cc(Cl)ccc2)ncc1Sc(cc1)cnc1N PEXJKRSJDMUVBX-UHFFFAOYSA-N 0.000 description 1
- BTWSFOJQRYVLCR-UHFFFAOYSA-N CN(CC1)CCN1c(nc1)nc(OCc2cccc(C#N)c2)c1Sc(cc1)ccc1C#N Chemical compound CN(CC1)CCN1c(nc1)nc(OCc2cccc(C#N)c2)c1Sc(cc1)ccc1C#N BTWSFOJQRYVLCR-UHFFFAOYSA-N 0.000 description 1
- DSIBSFXNFQSBLJ-UHFFFAOYSA-N CN(CC1)CCN1c(nc1)nc(OCc2ccccc2)c1Oc(cc1)ccc1C#N Chemical compound CN(CC1)CCN1c(nc1)nc(OCc2ccccc2)c1Oc(cc1)ccc1C#N DSIBSFXNFQSBLJ-UHFFFAOYSA-N 0.000 description 1
- YVUVIRQUINTZNL-UHFFFAOYSA-N CN(CC1)CCN1c(nc1)nc(OCc2ccccc2)c1Oc(cc1)ccc1C(N)=O Chemical compound CN(CC1)CCN1c(nc1)nc(OCc2ccccc2)c1Oc(cc1)ccc1C(N)=O YVUVIRQUINTZNL-UHFFFAOYSA-N 0.000 description 1
- SSMTZPQOKGRABN-UHFFFAOYSA-N CN(CC1)CCN1c(nc1OCc2ccccc2)ncc1Sc(cc1)ccc1C(OC)=O Chemical compound CN(CC1)CCN1c(nc1OCc2ccccc2)ncc1Sc(cc1)ccc1C(OC)=O SSMTZPQOKGRABN-UHFFFAOYSA-N 0.000 description 1
- AKFQWZHTEPWQMD-UHFFFAOYSA-N CN(CC1)CCN1c(nc1OCc2ccccc2)ncc1Sc1c(N)nccc1 Chemical compound CN(CC1)CCN1c(nc1OCc2ccccc2)ncc1Sc1c(N)nccc1 AKFQWZHTEPWQMD-UHFFFAOYSA-N 0.000 description 1
- FXLWNYKQWJQEDG-UHFFFAOYSA-N CN(CC1)CCN1c1nc(OCc(cc2)ccc2C#N)c(Cc(cc2)ccc2C(N)=O)cn1 Chemical compound CN(CC1)CCN1c1nc(OCc(cc2)ccc2C#N)c(Cc(cc2)ccc2C(N)=O)cn1 FXLWNYKQWJQEDG-UHFFFAOYSA-N 0.000 description 1
- PSRSDJWVGVWFBW-UHFFFAOYSA-N CN(CC1)CCN1c1nc(OCc2ccccc2)c(Cc(cc2)ccc2C(N)=O)cn1 Chemical compound CN(CC1)CCN1c1nc(OCc2ccccc2)c(Cc(cc2)ccc2C(N)=O)cn1 PSRSDJWVGVWFBW-UHFFFAOYSA-N 0.000 description 1
- SXXIZVPDUPGXGG-UHFFFAOYSA-N CN(CCN(C1)c(nc2OCc3cccc(OC)c3)ncc2Sc(cc2)ccc2C(N)=O)C1=O Chemical compound CN(CCN(C1)c(nc2OCc3cccc(OC)c3)ncc2Sc(cc2)ccc2C(N)=O)C1=O SXXIZVPDUPGXGG-UHFFFAOYSA-N 0.000 description 1
- CDZMIJFSAZPYEZ-VOTSOKGWSA-N COC(/C=C/c(cc1)ccc1C#N)=O Chemical compound COC(/C=C/c(cc1)ccc1C#N)=O CDZMIJFSAZPYEZ-VOTSOKGWSA-N 0.000 description 1
- BDKBJHDTWPUYOW-UHFFFAOYSA-N COc(cc(COc1nc(Cl)ncc1Sc(cc1)cc(Cl)c1C#N)cc1)c1F Chemical compound COc(cc(COc1nc(Cl)ncc1Sc(cc1)cc(Cl)c1C#N)cc1)c1F BDKBJHDTWPUYOW-UHFFFAOYSA-N 0.000 description 1
- HFXFMDNCWDPHQG-UHFFFAOYSA-N COc1cc(COc2nc(N3CCN(CC4CC4)CC3)ncc2Sc(cc2)ccc2C#N)ccc1 Chemical compound COc1cc(COc2nc(N3CCN(CC4CC4)CC3)ncc2Sc(cc2)ccc2C#N)ccc1 HFXFMDNCWDPHQG-UHFFFAOYSA-N 0.000 description 1
- RXJYRABGWBCEHE-UHFFFAOYSA-N COc1cccc(COc(nc(N2CCN(Cc3ccc[o]3)CC2)nc2)c2Sc(cc2)ccc2C#N)c1 Chemical compound COc1cccc(COc(nc(N2CCN(Cc3ccc[o]3)CC2)nc2)c2Sc(cc2)ccc2C#N)c1 RXJYRABGWBCEHE-UHFFFAOYSA-N 0.000 description 1
- NANNLPAAJYQWGH-UHFFFAOYSA-N COc1cccc(COc2nc(N3CCN(CCCCC#C)CC3)ncc2Sc(cc2)ccc2C#N)c1 Chemical compound COc1cccc(COc2nc(N3CCN(CCCCC#C)CC3)ncc2Sc(cc2)ccc2C#N)c1 NANNLPAAJYQWGH-UHFFFAOYSA-N 0.000 description 1
- GVWAZHUWEBCHPP-UHFFFAOYSA-N CS(c1nc(OCc(cc2)ccc2C#N)c(Cc(cc2)ccc2C(N)=O)cn1)(=O)=O Chemical compound CS(c1nc(OCc(cc2)ccc2C#N)c(Cc(cc2)ccc2C(N)=O)cn1)(=O)=O GVWAZHUWEBCHPP-UHFFFAOYSA-N 0.000 description 1
- HZJSJLQIGHULCL-UHFFFAOYSA-N CSc1nc(OCc(cc2)ccc2C#N)c(Cc(cc2)ccc2C(N)=O)cn1 Chemical compound CSc1nc(OCc(cc2)ccc2C#N)c(Cc(cc2)ccc2C(N)=O)cn1 HZJSJLQIGHULCL-UHFFFAOYSA-N 0.000 description 1
- ODDTVVQPZZQIEE-ZWKOTPCHSA-N C[C@@H](C1)N(C)C[C@@H](C)N1c(nc1OCc2ccccc2)ncc1Sc(cc1)ccc1C(N)=O Chemical compound C[C@@H](C1)N(C)C[C@@H](C)N1c(nc1OCc2ccccc2)ncc1Sc(cc1)ccc1C(N)=O ODDTVVQPZZQIEE-ZWKOTPCHSA-N 0.000 description 1
- XIBBOOKVCXHOAY-KRWDZBQOSA-N C[C@@H](c(cc1)ccc1F)Oc(nc(N1CCN(C)CC1)nc1)c1Sc(cc1)ccc1C#N Chemical compound C[C@@H](c(cc1)ccc1F)Oc(nc(N1CCN(C)CC1)nc1)c1Sc(cc1)ccc1C#N XIBBOOKVCXHOAY-KRWDZBQOSA-N 0.000 description 1
- SGVKTXOXEGGKFR-GOSISDBHSA-N C[C@H](c(cc1)ccc1F)Oc(nc(N1CCN(C)CC1)nc1)c1Sc(cc1)ccc1C(C)=O Chemical compound C[C@H](c(cc1)ccc1F)Oc(nc(N1CCN(C)CC1)nc1)c1Sc(cc1)ccc1C(C)=O SGVKTXOXEGGKFR-GOSISDBHSA-N 0.000 description 1
- HHAOOPAUMXSHBT-UHFFFAOYSA-N Cc(c(F)c(COc1nc(N2CCN(C)CC2)ncc1Sc(cc1)cnc1N)cc1)c1F Chemical compound Cc(c(F)c(COc1nc(N2CCN(C)CC2)ncc1Sc(cc1)cnc1N)cc1)c1F HHAOOPAUMXSHBT-UHFFFAOYSA-N 0.000 description 1
- QRSLVUJNTJQHBA-UHFFFAOYSA-N Cc(cc(COc1nc(N2CCN(C)CC2)ncc1Sc(cc1)cnc1N)cc1)c1F Chemical compound Cc(cc(COc1nc(N2CCN(C)CC2)ncc1Sc(cc1)cnc1N)cc1)c1F QRSLVUJNTJQHBA-UHFFFAOYSA-N 0.000 description 1
- WVSCEBGQKRABBE-UHFFFAOYSA-N Cc(nc(N1CCN(C)CC1)nc1)c1I Chemical compound Cc(nc(N1CCN(C)CC1)nc1)c1I WVSCEBGQKRABBE-UHFFFAOYSA-N 0.000 description 1
- WFDLWULWLAJJAV-UHFFFAOYSA-N Cc1cc(COc2nc(N(CCN3C)CC3=O)ncc2Sc(cc2)ccc2C#N)ccc1 Chemical compound Cc1cc(COc2nc(N(CCN3C)CC3=O)ncc2Sc(cc2)ccc2C#N)ccc1 WFDLWULWLAJJAV-UHFFFAOYSA-N 0.000 description 1
- RESHKAHTSWIWOO-UHFFFAOYSA-N Cc1cc(COc2nc(N3CCN(C)CC3)ncc2Sc2ccc(N)nc2)cc(C(F)(F)F)c1 Chemical compound Cc1cc(COc2nc(N3CCN(C)CC3)ncc2Sc2ccc(N)nc2)cc(C(F)(F)F)c1 RESHKAHTSWIWOO-UHFFFAOYSA-N 0.000 description 1
- CPRZFVYISWTZLT-UHFFFAOYSA-N Cc1ccc(C(N)=O)c(C(F)(F)F)c1 Chemical compound Cc1ccc(C(N)=O)c(C(F)(F)F)c1 CPRZFVYISWTZLT-UHFFFAOYSA-N 0.000 description 1
- YJLVPLFYKJDHSM-UHFFFAOYSA-N Cc1ccc(C(N)=O)c(I)c1 Chemical compound Cc1ccc(C(N)=O)c(I)c1 YJLVPLFYKJDHSM-UHFFFAOYSA-N 0.000 description 1
- OKPRELYNHXXTAO-UHFFFAOYSA-N Cc1cccc(COc2nc(N(CC3)CC3N(C)C)ncc2Sc(cc2)cnc2N)c1 Chemical compound Cc1cccc(COc2nc(N(CC3)CC3N(C)C)ncc2Sc(cc2)cnc2N)c1 OKPRELYNHXXTAO-UHFFFAOYSA-N 0.000 description 1
- GAYKIMSNWVDJEF-HXUWFJFHSA-N Cc1cccc(COc2nc(N(CC3)C[C@@H]3N(C)C)ncc2Sc(cc2)ccc2C(N)=O)c1 Chemical compound Cc1cccc(COc2nc(N(CC3)C[C@@H]3N(C)C)ncc2Sc(cc2)ccc2C(N)=O)c1 GAYKIMSNWVDJEF-HXUWFJFHSA-N 0.000 description 1
- XIKKYMICMUQGNW-UHFFFAOYSA-N Cc1cccc(COc2nc(N3C(C4)CN(C)C4C3)ncc2Sc(cc2)ccc2C(N)=O)c1 Chemical compound Cc1cccc(COc2nc(N3C(C4)CN(C)C4C3)ncc2Sc(cc2)ccc2C(N)=O)c1 XIKKYMICMUQGNW-UHFFFAOYSA-N 0.000 description 1
- UBVAORPHTYRTIS-UHFFFAOYSA-N Cc1cccc(COc2nc(N3CCN(C)CC3)ncc2Oc(cc2)ccc2C(N)=O)c1 Chemical compound Cc1cccc(COc2nc(N3CCN(C)CC3)ncc2Oc(cc2)ccc2C(N)=O)c1 UBVAORPHTYRTIS-UHFFFAOYSA-N 0.000 description 1
- BDCSCRTWMCCXMZ-UHFFFAOYSA-N Cc1cccc(COc2nc(N3CCN(C)CC3)ncc2Sc(cc2)ccc2C#N)c1 Chemical compound Cc1cccc(COc2nc(N3CCN(C)CC3)ncc2Sc(cc2)ccc2C#N)c1 BDCSCRTWMCCXMZ-UHFFFAOYSA-N 0.000 description 1
- PHBXIXYFTNXSIP-UHFFFAOYSA-N Cc1nccc(COc2nc(N3CCN(C)CC3)ncc2Sc(cc2)ccc2C(N)=O)c1 Chemical compound Cc1nccc(COc2nc(N3CCN(C)CC3)ncc2Sc(cc2)ccc2C(N)=O)c1 PHBXIXYFTNXSIP-UHFFFAOYSA-N 0.000 description 1
- SXWACHMYOAKSGA-UHFFFAOYSA-N N#Cc(c(Cl)c1)ccc1Sc(cnc(O)n1)c1O Chemical compound N#Cc(c(Cl)c1)ccc1Sc(cnc(O)n1)c1O SXWACHMYOAKSGA-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N N#Cc(cc1)ccc1O Chemical compound N#Cc(cc1)ccc1O CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- HHAYQKIKZWUXSH-UHFFFAOYSA-N N#Cc(cc1)ccc1Oc(c(O)n1)cnc1S Chemical compound N#Cc(cc1)ccc1Oc(c(O)n1)cnc1S HHAYQKIKZWUXSH-UHFFFAOYSA-N 0.000 description 1
- ZHNRASVSIGGJMR-UHFFFAOYSA-N N#Cc(cc1)ccc1Sc1cnc(N2CCOCC2)nc1OCc1ccccc1 Chemical compound N#Cc(cc1)ccc1Sc1cnc(N2CCOCC2)nc1OCc1ccccc1 ZHNRASVSIGGJMR-UHFFFAOYSA-N 0.000 description 1
- IPRWIMRMQSUCIG-UHFFFAOYSA-N N#Cc(ccc(Sc(cnc(Cl)n1)c1Cl)c1)c1Cl Chemical compound N#Cc(ccc(Sc(cnc(Cl)n1)c1Cl)c1)c1Cl IPRWIMRMQSUCIG-UHFFFAOYSA-N 0.000 description 1
- WZWIQYMTQZCSKI-UHFFFAOYSA-N N#Cc1ccc(C=O)cc1 Chemical compound N#Cc1ccc(C=O)cc1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
- CEIVMXMPBABKGI-ZZXKWVIFSA-N NC(c1ccc(/C=C/C(O)=O)cc1)=O Chemical compound NC(c1ccc(/C=C/C(O)=O)cc1)=O CEIVMXMPBABKGI-ZZXKWVIFSA-N 0.000 description 1
- YKZDVMZFKHGNFO-UHFFFAOYSA-N O=Cc1cccc(Sc(cnc(N2CCNCC2)n2)c2OCc2ccccc2)c1 Chemical compound O=Cc1cccc(Sc(cnc(N2CCNCC2)n2)c2OCc2ccccc2)c1 YKZDVMZFKHGNFO-UHFFFAOYSA-N 0.000 description 1
- KSNXJLQDQOIRIP-UHFFFAOYSA-N Oc1nc(O)ncc1I Chemical compound Oc1nc(O)ncc1I KSNXJLQDQOIRIP-UHFFFAOYSA-N 0.000 description 1
- IIRVUYFJHBICFO-UHFFFAOYSA-N [O-][N+](c(cc1)ncc1Sc(cnc(N1CCCC1)n1)c1O)=O Chemical compound [O-][N+](c(cc1)ncc1Sc(cnc(N1CCCC1)n1)c1O)=O IIRVUYFJHBICFO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- 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
- C07D417/12—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461992838P | 2014-05-13 | 2014-05-13 | |
| US61/992,838 | 2014-05-13 | ||
| PCT/US2015/030641 WO2015175707A1 (en) | 2014-05-13 | 2015-05-13 | Hsp70 modulators and methods for making and using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2015259173A1 AU2015259173A1 (en) | 2016-12-08 |
| AU2015259173B2 true AU2015259173B2 (en) | 2019-09-05 |
Family
ID=53284541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2015259173A Ceased AU2015259173B2 (en) | 2014-05-13 | 2015-05-13 | Hsp70 modulators and methods for making and using the same |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US9878987B2 (OSRAM) |
| EP (1) | EP3143013B1 (OSRAM) |
| JP (1) | JP6607870B2 (OSRAM) |
| KR (1) | KR102461419B1 (OSRAM) |
| CN (1) | CN107074806B (OSRAM) |
| AU (1) | AU2015259173B2 (OSRAM) |
| BR (1) | BR112016026470A8 (OSRAM) |
| CA (1) | CA2948621A1 (OSRAM) |
| EA (1) | EA201692155A1 (OSRAM) |
| ES (1) | ES2774975T3 (OSRAM) |
| IL (1) | IL248792B (OSRAM) |
| MX (1) | MX375924B (OSRAM) |
| PH (1) | PH12016502244A1 (OSRAM) |
| SG (1) | SG11201609336PA (OSRAM) |
| TW (1) | TWI699204B (OSRAM) |
| WO (1) | WO2015175707A1 (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3205647B1 (en) | 2009-08-17 | 2020-05-13 | Memorial Sloan-Kettering Cancer Center | 2-(pyrimidin-5-yl)-thiopyrimidine derivatives as hsp70 and hsc70 modulators for the treatment of proliferative disorders |
| EP3143013B1 (en) * | 2014-05-13 | 2019-12-18 | Memorial Sloan Kettering Cancer Center | Hsp70 modulators and methods for making and using the same |
| AU2016336351A1 (en) | 2015-10-05 | 2018-05-10 | Memorial Sloan Kettering Cancer Center | Rational combination therapy for the treatment of cancer |
| CN112368272B (zh) * | 2018-03-21 | 2023-04-21 | 苏州浦合医药科技有限公司 | Shp2抑制剂及其用途 |
| AU2019327006B2 (en) | 2018-08-27 | 2024-02-15 | Sumitomo Pharma Co., Ltd. | Optically active azabicyclic derivative |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011022440A2 (en) * | 2009-08-17 | 2011-02-24 | Memorial Sloan-Kettering Cancer Center | Heat shock protein binding compounds, compositions, and methods for making and using same |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB951432A (en) | 1959-03-17 | 1964-03-04 | Wellcome Found | Pyrimidine derivatives and the manufacture thereof |
| GB990857A (en) | 1961-10-13 | 1965-05-05 | Wellcome Found | 1,3-diazaphenothiazines |
| US3248393A (en) | 1960-06-23 | 1966-04-26 | Burroughs Wellcome Co | 1, 3-diazaphenothiazines and method |
| CH605828A5 (OSRAM) | 1974-12-24 | 1978-10-13 | Hoffmann La Roche | |
| US4039543A (en) | 1974-12-24 | 1977-08-02 | Hoffmann-La Roche Inc. | Benzylpyrimidines |
| US4096264A (en) | 1975-12-09 | 1978-06-20 | Merck & Co., Inc. | Certain substituted imidazo [1,2-a] pyridines |
| DE3311703A1 (de) | 1983-03-30 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Harnstoffderivate |
| US4911920A (en) | 1986-07-30 | 1990-03-27 | Alcon Laboratories, Inc. | Sustained release, comfort formulation for glaucoma therapy |
| FR2588189B1 (fr) | 1985-10-03 | 1988-12-02 | Merck Sharp & Dohme | Composition pharmaceutique de type a transition de phase liquide-gel |
| JP2594486B2 (ja) | 1991-01-15 | 1997-03-26 | アルコン ラボラトリーズ インコーポレイテッド | 局所的眼薬組成物 |
| US5212162A (en) | 1991-03-27 | 1993-05-18 | Alcon Laboratories, Inc. | Use of combinations gelling polysaccharides and finely divided drug carrier substrates in topical ophthalmic compositions |
| PL313973A1 (en) | 1993-10-12 | 1996-08-05 | Du Pont Merck Pharma | 1 n-alkyl-n-arylopyrimidin amines and their derivatives |
| DE4423098A1 (de) | 1994-07-01 | 1996-01-04 | Hoechst Ag | Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien |
| US6309853B1 (en) | 1994-08-17 | 2001-10-30 | The Rockfeller University | Modulators of body weight, corresponding nucleic acids and proteins, and diagnostic and therapeutic uses thereof |
| JPH09236070A (ja) | 1996-02-29 | 1997-09-09 | Denso Corp | スタータ |
| US5707930A (en) | 1996-09-16 | 1998-01-13 | Zeneca Limited | 4-cycloalkyl-5-substituted pyrimidine compounds useful as crop protection agents |
| US6710048B2 (en) | 2000-09-20 | 2004-03-23 | Ortho-Mcneil Pharmaceutical, Inc. | Pyrazine derivatives as modulators of tyrosine kinases |
| BRPI0116237B8 (pt) | 2000-12-18 | 2021-05-25 | Actelion Pharmaceuticals Ltd | "composto de sulfamida, composição farmacêutica contendo o mesmo e seu uso como medicamento antagonista de receptor de endotelina". |
| US6423720B1 (en) | 2001-02-01 | 2002-07-23 | Duquesne University Of The Holy Ghost | Pyrimidine compounds and methods for making and using the same |
| US7501429B2 (en) | 2001-04-11 | 2009-03-10 | Queen's University At Kingston | Pyrimidine compounds as anti-ictogenic and/or anti-epileptogenic agents |
| ATE374753T1 (de) | 2001-12-21 | 2007-10-15 | Vernalis Cambridge Ltd | 3-(2,4)dihydroxyphenyl-4-phenylpyrazole und deren medizinische verwendung |
| RS51752B (sr) | 2002-07-29 | 2011-12-31 | Rigel Pharmaceuticals | Metode tretiranja i prevencije autoimunih oboljenja jedinjenjima 2,4-pirimidindiamina |
| WO2004081001A1 (ja) | 2003-02-13 | 2004-09-23 | Banyu Pharmaceutical Co., Ltd. | 新規2-ピリジンカルボキサミド誘導体 |
| WO2005021552A1 (en) | 2003-08-29 | 2005-03-10 | Vernalis (Cambridge) Ltd | Pyrimidothiophene compounds |
| US20050070712A1 (en) | 2003-09-26 | 2005-03-31 | Christi Kosogof | Pyrimidine derivatives as ghrelin receptor modulators |
| ES2391636T3 (es) | 2004-03-05 | 2012-11-28 | F. Hoffmann-La Roche Ag | Diaminopirimidinas como antagonistas de P2X3 y P2X2/3 |
| TW200608976A (en) | 2004-05-08 | 2006-03-16 | Neurogen Corp | 4,5-disubstituted-2-aryl pyrimidines |
| CN101155799A (zh) | 2005-03-16 | 2008-04-02 | 塔格根公司 | 嘧啶化合物和使用方法 |
| CA2620129C (en) * | 2005-09-01 | 2014-12-23 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| WO2007131034A1 (en) | 2006-05-03 | 2007-11-15 | The Regents Of The University Of Michigan | Pyrimidone derivatives which are modulators of heat shock protein (hsp) 70 |
| JP2008081492A (ja) | 2006-08-31 | 2008-04-10 | Banyu Pharmaceut Co Ltd | オーロラa選択的阻害作用を有する新規アミノピリジン誘導体 |
| US20080124407A1 (en) | 2006-10-10 | 2008-05-29 | University Of Washington | Inhibiting cyp3a4 induction |
| PT2091918E (pt) | 2006-12-08 | 2014-11-24 | Irm Llc | Compostos e composições como inibidores de proteína cinase |
| PT2114900T (pt) | 2007-01-31 | 2019-01-17 | Ym Biosciences Australia Pty | Compostos à base de tiopirimidina e as suas utilizações |
| TW200911240A (en) | 2007-06-11 | 2009-03-16 | Kyowa Hakko Kogyo Kk | Anti-tumor agent |
| US8754094B2 (en) | 2007-08-15 | 2014-06-17 | The Research Foundation Of State University Of New York | Methods for heat shock protein dependent cancer treatment |
| WO2009061345A2 (en) | 2007-11-07 | 2009-05-14 | Cornell Research Foundation, Inc. | Targeting cdk4 and cdk6 in cancer therapy |
| PE20091236A1 (es) | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| CN102573486A (zh) | 2009-06-08 | 2012-07-11 | 加利福尼亚资本权益有限责任公司 | 三嗪衍生物及其治疗应用 |
| WO2014078294A1 (en) * | 2012-11-13 | 2014-05-22 | Memorial Sloan-Kettering Cancer Center | Indole compounds and their use as antimicrobials |
| EP3143013B1 (en) | 2014-05-13 | 2019-12-18 | Memorial Sloan Kettering Cancer Center | Hsp70 modulators and methods for making and using the same |
| US10308660B2 (en) * | 2015-06-19 | 2019-06-04 | Novartis Ag | Compounds and compositions for inhibiting the activity of SHP2 |
| PL3349743T3 (pl) * | 2015-09-18 | 2022-08-08 | St. Jude Children's Research Hospital | Sposoby i kompozycje do hamowania oddziaływania dcn1-ubc12 |
-
2015
- 2015-05-13 EP EP15727138.8A patent/EP3143013B1/en active Active
- 2015-05-13 CN CN201580036973.3A patent/CN107074806B/zh not_active Expired - Fee Related
- 2015-05-13 SG SG11201609336PA patent/SG11201609336PA/en unknown
- 2015-05-13 BR BR112016026470A patent/BR112016026470A8/pt not_active Application Discontinuation
- 2015-05-13 US US15/310,142 patent/US9878987B2/en active Active
- 2015-05-13 MX MX2016014755A patent/MX375924B/es active IP Right Grant
- 2015-05-13 CA CA2948621A patent/CA2948621A1/en active Pending
- 2015-05-13 AU AU2015259173A patent/AU2015259173B2/en not_active Ceased
- 2015-05-13 ES ES15727138T patent/ES2774975T3/es active Active
- 2015-05-13 WO PCT/US2015/030641 patent/WO2015175707A1/en not_active Ceased
- 2015-05-13 KR KR1020167034791A patent/KR102461419B1/ko active Active
- 2015-05-13 TW TW104115328A patent/TWI699204B/zh not_active IP Right Cessation
- 2015-05-13 EA EA201692155A patent/EA201692155A1/ru unknown
- 2015-05-13 JP JP2016567656A patent/JP6607870B2/ja not_active Expired - Fee Related
-
2016
- 2016-11-07 IL IL248792A patent/IL248792B/en active IP Right Grant
- 2016-11-11 PH PH12016502244A patent/PH12016502244A1/en unknown
-
2017
- 2017-12-14 US US15/842,755 patent/US10160729B2/en active Active
-
2018
- 2018-11-02 US US16/179,155 patent/US10647683B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011022440A2 (en) * | 2009-08-17 | 2011-02-24 | Memorial Sloan-Kettering Cancer Center | Heat shock protein binding compounds, compositions, and methods for making and using same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015175707A1 (en) | 2015-11-19 |
| AU2015259173A1 (en) | 2016-12-08 |
| KR102461419B1 (ko) | 2022-11-02 |
| CN107074806B (zh) | 2021-04-23 |
| MX375924B (es) | 2025-03-07 |
| CA2948621A1 (en) | 2015-11-19 |
| EP3143013B1 (en) | 2019-12-18 |
| MX2016014755A (es) | 2017-03-27 |
| EA201692155A1 (ru) | 2017-04-28 |
| US20180170883A1 (en) | 2018-06-21 |
| ES2774975T3 (es) | 2020-07-23 |
| IL248792A0 (en) | 2017-01-31 |
| JP6607870B2 (ja) | 2019-11-20 |
| US9878987B2 (en) | 2018-01-30 |
| US20170233352A1 (en) | 2017-08-17 |
| US10647683B2 (en) | 2020-05-12 |
| PH12016502244A1 (en) | 2017-01-09 |
| TWI699204B (zh) | 2020-07-21 |
| US20190241526A1 (en) | 2019-08-08 |
| BR112016026470A2 (pt) | 2017-08-15 |
| JP2017515857A (ja) | 2017-06-15 |
| IL248792B (en) | 2020-01-30 |
| TW201601725A (zh) | 2016-01-16 |
| KR20170005095A (ko) | 2017-01-11 |
| SG11201609336PA (en) | 2016-12-29 |
| BR112016026470A8 (pt) | 2021-07-20 |
| CN107074806A (zh) | 2017-08-18 |
| US10160729B2 (en) | 2018-12-25 |
| EP3143013A1 (en) | 2017-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20230338373A1 (en) | Inhibitor of indoleamine-2,3-dioxygenase (ido) | |
| US10647683B2 (en) | Hsp70 modulators and methods for making and using the same | |
| US9365519B2 (en) | PRMT5 inhibitors and uses thereof | |
| EP2935247B1 (en) | Prmt5 inhibitors and uses thereof | |
| Lipeeva et al. | Synthesis of 1H-1, 2, 3-triazole linked aryl (arylamidomethyl)–dihydrofurocoumarin hybrids and analysis of their cytotoxicity | |
| KR20190115451A (ko) | 항-섬유성 화합물 | |
| EP2693879B1 (en) | Migrastatins and uses thereof | |
| WO2024220676A1 (en) | Mrna degraders and methods of use thereof | |
| HK1234393A1 (en) | Hsp70 modulators and methods for making and using the same | |
| HK1234393B (en) | Hsp70 modulators and methods for making and using the same | |
| KR101297652B1 (ko) | 항암활성을 지닌 카르보아졸계 화합물 | |
| Komirishetti et al. | Synthesis and biological evaluation of chalcone derivatives of oxazole-pyrimidines as anticancer agents | |
| WO2013062071A1 (ja) | ピペラジン誘導体及びその塩 | |
| HK1194617A (en) | Migrastatins and uses thereof | |
| HK1194617B (en) | Migrastatins and uses thereof | |
| NZ755866B2 (en) | Anti-fibrotic compounds | |
| WO2014085791A2 (en) | Compositions and uses thereof for treating multiple myeloma |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |