AU2014273983A1

AU2014273983A1 - Cyclodextrin-based polymers for the therapeutic delivery

Cyclodextrin-based polymers for the therapeutic delivery Download PDF

Info

Publication number: AU2014273983A1
Authority: AU; Australia
Prior art keywords: cdp; conjugate; jak inhibitor; jak; moiety
Prior art date: 2013-05-31
Legal status : Abandoned

Application number

AU2014273983A

Other languages

English (en)

Inventor

Roderic O. Cole

Derek Gregory Van Der Poll

Current Assignee

Dare Bioscience Inc

Original Assignee

Cerulean Pharma Inc

Priority date

2013-05-31

Filing date

2014-05-30

Publication date

2015-12-17

2014-05-30 Application filed by Cerulean Pharma Inc filed Critical Cerulean Pharma Inc

2015-12-17 Publication of AU2014273983A1 publication Critical patent/AU2014273983A1/en

Status Abandoned legal-status Critical Current

Links

HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims description 80
229920000642 polymer Polymers 0.000 title claims description 76
229920000858 Cyclodextrin Polymers 0.000 title claims description 44
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238000000034 method Methods 0.000 claims abstract description 120
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UJLAWZDWDVHWOW-YPMHNXCESA-N tofacitinib Chemical compound C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1N(C)C1=NC=NC2=C1C=CN2 UJLAWZDWDVHWOW-YPMHNXCESA-N 0.000 claims description 95
229950000971 baricitinib Drugs 0.000 claims description 94
HFNKQEVNSGCOJV-OAHLLOKOSA-N ruxolitinib Chemical group C1([C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCCC1 HFNKQEVNSGCOJV-OAHLLOKOSA-N 0.000 claims description 80
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XUZMWHLSFXCVMG-UHFFFAOYSA-N baricitinib Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 XUZMWHLSFXCVMG-UHFFFAOYSA-N 0.000 claims description 51
229950001845 lestaurtinib Drugs 0.000 claims description 51
RIJLVEAXPNLDTC-UHFFFAOYSA-N n-[5-[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(=NN12)N=C1C=CC=C2C(C=C1)=CC=C1CN1CCS(=O)(=O)CC1 RIJLVEAXPNLDTC-UHFFFAOYSA-N 0.000 claims description 50
-1 poly(ethyleneimine) Polymers 0.000 claims description 41
PDOQBOJDRPLBQU-QMMMGPOBSA-N 5-chloro-2-n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-4-n-(5-methyl-1h-pyrazol-3-yl)pyrimidine-2,4-diamine Chemical compound N([C@@H](C)C=1N=CC(F)=CN=1)C(N=1)=NC=C(Cl)C=1NC=1C=C(C)NN=1 PDOQBOJDRPLBQU-QMMMGPOBSA-N 0.000 claims description 36
RFZKSQIFOZZIAQ-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)phenyl]-8-(4-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=CC(NC2=NN3C=CC=C(C3=N2)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 RFZKSQIFOZZIAQ-UHFFFAOYSA-N 0.000 claims description 36
UIARLYUEJFELEN-LROUJFHJSA-N LSM-1231 Chemical compound C12=C3N4C5=CC=CC=C5C3=C3C(=O)NCC3=C2C2=CC=CC=C2N1[C@]1(C)[C@](CO)(O)C[C@H]4O1 UIARLYUEJFELEN-LROUJFHJSA-N 0.000 claims description 32
MPYACSQFXVMWNO-UHFFFAOYSA-N n-[5-[4-(3,3-dimethylazetidine-1-carbonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide Chemical compound C1C(C)(C)CN1C(=O)C1=CC=C(C=2N3N=C(NC(=O)C4CC4)N=C3C=CC=2)C=C1 MPYACSQFXVMWNO-UHFFFAOYSA-N 0.000 claims description 32
JOOXLOJCABQBSG-UHFFFAOYSA-N N-tert-butyl-3-[[5-methyl-2-[4-[2-(1-pyrrolidinyl)ethoxy]anilino]-4-pyrimidinyl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 JOOXLOJCABQBSG-UHFFFAOYSA-N 0.000 claims description 31
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ASUGUQWIHMTFJL-QGZVFWFLSA-N (2r)-2-methyl-2-[[2-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]-n-(2,2,2-trifluoroethyl)butanamide Chemical compound FC(F)(F)CNC(=O)[C@@](C)(CC)NC1=CC=NC(C=2C3=CC=CN=C3NC=2)=N1 ASUGUQWIHMTFJL-QGZVFWFLSA-N 0.000 claims description 29
JCINBYQJBYJGDM-UHFFFAOYSA-N bms-911543 Chemical compound CCN1C(C(=O)N(C2CC2)C2CC2)=CC(C=2N(C)C=NC=22)=C1N=C2NC=1C=C(C)N(C)N=1 JCINBYQJBYJGDM-UHFFFAOYSA-N 0.000 claims description 29
DCRWIATZWHLIPN-UHFFFAOYSA-N (4-fluorophenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(O)C=2C=CC(F)=CC=2)=N1 DCRWIATZWHLIPN-UHFFFAOYSA-N 0.000 claims description 28
IBPVXAOOVUAOKJ-UHFFFAOYSA-N 4-[[2,6-difluoro-4-[3-(1-piperidin-4-ylpyrazol-4-yl)quinoxalin-5-yl]phenyl]methyl]morpholine Chemical compound FC1=CC(C=2C3=NC(=CN=C3C=CC=2)C2=CN(N=C2)C2CCNCC2)=CC(F)=C1CN1CCOCC1 IBPVXAOOVUAOKJ-UHFFFAOYSA-N 0.000 claims description 28
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