JP2019531274A5 - - Google Patents
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- Publication number
- JP2019531274A5 JP2019531274A5 JP2019511947A JP2019511947A JP2019531274A5 JP 2019531274 A5 JP2019531274 A5 JP 2019531274A5 JP 2019511947 A JP2019511947 A JP 2019511947A JP 2019511947 A JP2019511947 A JP 2019511947A JP 2019531274 A5 JP2019531274 A5 JP 2019531274A5
- Authority
- JP
- Japan
- Prior art keywords
- bis
- oxy
- biphenyl
- dimethyl
- diyl
- 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.)
- Granted
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- -1 amino, carboxy Chemical group 0.000 claims 187
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 83
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 64
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 52
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 28
- 235000010290 biphenyl Nutrition 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 125000004076 pyridyl group Chemical group 0.000 claims 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 20
- 125000005843 halogen group Chemical group 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000003386 piperidinyl group Chemical group 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 11
- 229940124597 therapeutic agent Drugs 0.000 claims 11
- 239000004146 Propane-1,2-diol Substances 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 10
- 229960004063 propylene glycol Drugs 0.000 claims 10
- 235000013772 propylene glycol Nutrition 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims 8
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims 8
- DBXBTMSZEOQQDU-UHFFFAOYSA-N 3-hydroxyisobutyric acid Chemical compound OCC(C)C(O)=O DBXBTMSZEOQQDU-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 5
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims 4
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims 4
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 4
- 125000004450 alkenylene group Chemical group 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 3
- 235000019260 propionic acid Nutrition 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 3
- UXOQCYFKGDPUDV-PLXFJCCSSA-N (2S,4R)-4-hydroxy-1-[3-[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidine-2-carboxylic acid Chemical compound O[C@@H]1C[C@H](N(C1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)C(=O)O UXOQCYFKGDPUDV-PLXFJCCSSA-N 0.000 claims 2
- PKCXYIGMQIXBHG-YOQGVNIDSA-N (3R)-1-[3-[3-[3-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethyl]-2,3-dihydro-1,4-benzodioxin-6-yl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound O[C@H]1CN(CC1)CCC1OC2=C(OC1)C=CC(=C2)C=1C(=C(OCCCN2C[C@@H](CC2)O)C=CC=1)C PKCXYIGMQIXBHG-YOQGVNIDSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- SPJPZSUFBQISRE-UHFFFAOYSA-N 1-[3-[2-methyl-3-(2-methylphenyl)phenoxy]propyl]pyrrolidin-3-ol Chemical compound OC1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C=CC=C1)C)C SPJPZSUFBQISRE-UHFFFAOYSA-N 0.000 claims 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N 4-hydroxyproline Chemical compound OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000028993 immune response Effects 0.000 claims 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims 2
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- ZAMUNOUDPJRWIJ-QPPBQGQZSA-N (2S)-2-hydroxy-3-[3-[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenoxy]propylamino]propanoic acid Chemical compound O[C@H](C(=O)O)CNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C ZAMUNOUDPJRWIJ-QPPBQGQZSA-N 0.000 claims 1
- SHMLWSKIQITORU-VMPREFPWSA-N (2S)-3-[3-[3-[3-[3-[[(2S)-2,3-dihydroxypropyl]-(2-pyridin-3-ylethyl)amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propylamino]propane-1,2-diol Chemical compound O[C@@H](CN(CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNC[C@@H](CO)O)C)C)CCC=1C=NC=CC=1)CO SHMLWSKIQITORU-VMPREFPWSA-N 0.000 claims 1
- XUVCRLNALYWPFO-DFHRPNOPSA-N (2S)-3-hydroxy-2-[3-[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenoxy]propylamino]-2-methylpropanoic acid Chemical compound OC[C@](C(=O)O)(C)NCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C XUVCRLNALYWPFO-DFHRPNOPSA-N 0.000 claims 1
- IQYCVHPCIZMJIG-JUQKIHQQSA-N (2S,3S)-3-[3-[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenoxy]propylamino]-3-phenylpropane-1,2-diol Chemical compound O[C@H]1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN[C@H]([C@@H](CO)O)C1=CC=CC=C1)C)C IQYCVHPCIZMJIG-JUQKIHQQSA-N 0.000 claims 1
- SPJPZSUFBQISRE-GOSISDBHSA-N (3R)-1-[3-[2-methyl-3-(2-methylphenyl)phenoxy]propyl]pyrrolidin-3-ol Chemical compound O[C@H]1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C=CC=C1)C)C SPJPZSUFBQISRE-GOSISDBHSA-N 0.000 claims 1
- PJFDIUZZYNDMBT-RUZDIDTESA-N (3R)-1-[3-[2-methyl-3-[2-methyl-3-(3-piperidin-1-ylpropoxy)phenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=C(C(=CC=C1)OCCCN1CCCCC1)C PJFDIUZZYNDMBT-RUZDIDTESA-N 0.000 claims 1
- UTWZLLUIGZQEHS-XMMISQBUSA-N (3R)-1-[3-[2-methyl-3-[2-methyl-3-[(1-methylpiperidin-3-yl)methoxy]phenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=C(C(=CC=C1)OCC1CN(CCC1)C)C UTWZLLUIGZQEHS-XMMISQBUSA-N 0.000 claims 1
- AOTXMUNSPVUYKX-RUZDIDTESA-N (3R)-1-[3-[2-methyl-3-[2-methyl-3-[3-(2-pyrazol-1-ylethylamino)propoxy]phenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound N1(N=CC=C1)CCNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C AOTXMUNSPVUYKX-RUZDIDTESA-N 0.000 claims 1
- YFWBKLCOKIURAV-GDLZYMKVSA-N (3R)-1-[3-[2-methyl-3-[2-methyl-3-[3-[methyl(2-phenylethyl)amino]propoxy]phenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=C(C(=CC=C1)OCCCN(CCC1=CC=CC=C1)C)C YFWBKLCOKIURAV-GDLZYMKVSA-N 0.000 claims 1
- IUYQJMVGGQCYAW-HHHXNRCGSA-N (3R)-1-[3-[2-methyl-3-[2-methyl-3-[3-[methyl(pyridin-2-ylmethyl)amino]propoxy]phenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=C(C(=CC=C1)OCCCN(CC1=NC=CC=C1)C)C IUYQJMVGGQCYAW-HHHXNRCGSA-N 0.000 claims 1
- ZMDHASBCNOHLFM-HHHXNRCGSA-N (3R)-1-[3-[2-methyl-3-[2-methyl-3-[3-[methyl(pyridin-4-ylmethyl)amino]propoxy]phenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=C(C(=CC=C1)OCCCN(CC1=CC=NC=C1)C)C ZMDHASBCNOHLFM-HHHXNRCGSA-N 0.000 claims 1
- JCMVCJJPQVNXSQ-AREMUKBSSA-N (3R)-1-[3-[2-methyl-3-[2-methyl-3-[3-[methyl-[2-[2-(methylamino)ethoxy]ethyl]amino]propoxy]phenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=C(C(=CC=C1)OCCCN(CCOCCNC)C)C JCMVCJJPQVNXSQ-AREMUKBSSA-N 0.000 claims 1
- UDCOHOFRJVUEGM-AREMUKBSSA-N (3R)-1-[3-[2-methyl-3-[3-(3-phenylpropoxy)phenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=CC(=CC=C1)OCCCC1=CC=CC=C1 UDCOHOFRJVUEGM-AREMUKBSSA-N 0.000 claims 1
- YHEYJBXAADEELQ-FGZHOGPDSA-N (3R)-1-[3-[3-[2-chloro-3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]phenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound ClC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C YHEYJBXAADEELQ-FGZHOGPDSA-N 0.000 claims 1
- VSJTZCLPKHRPRH-AREMUKBSSA-N (3R)-1-[3-[3-[3-[3-(3-imidazol-1-ylpropylamino)propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound N1(C=NC=C1)CCCNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C VSJTZCLPKHRPRH-AREMUKBSSA-N 0.000 claims 1
- ZVPPJPUZOIVUTB-GDLZYMKVSA-N (3R)-1-[3-[3-[3-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound COC=1C=C2CCN(CC2=CC=1OC)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C ZVPPJPUZOIVUTB-GDLZYMKVSA-N 0.000 claims 1
- XNPYNCNECHZDJZ-QZWVJJBASA-N (3R)-1-[3-[3-[3-[3-[(2-hydroxy-1-pyridin-4-ylethyl)amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound OCC(C1=CC=NC=C1)NCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C XNPYNCNECHZDJZ-QZWVJJBASA-N 0.000 claims 1
- BNNLKLMGJWJKAC-QZWVJJBASA-N (3R)-1-[3-[3-[3-[3-[(2-hydroxy-2-pyridin-3-ylethyl)amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound OC(CNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)C=1C=NC=CC=1 BNNLKLMGJWJKAC-QZWVJJBASA-N 0.000 claims 1
- FNOQQPWACKVFEW-DNQXCXABSA-N (3R)-1-[3-[3-[3-[3-[(3R)-3-fluoropyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound F[C@H]1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C FNOQQPWACKVFEW-DNQXCXABSA-N 0.000 claims 1
- IYMILTTVAXIHRW-JWQCQUIFSA-N (3R)-1-[3-[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]piperidine-3-carboxylic acid Chemical compound O[C@H]1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CCC1)C(=O)O)C)C IYMILTTVAXIHRW-JWQCQUIFSA-N 0.000 claims 1
- HPXNLRDTKCJCDZ-DNQXCXABSA-N (3R)-1-[3-[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C HPXNLRDTKCJCDZ-DNQXCXABSA-N 0.000 claims 1
- IXHPUSSTLKYZHV-DNQXCXABSA-N (3R)-1-[3-[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-4-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=CC(=CC=C1C)OCCCN1C[C@@H](CC1)O IXHPUSSTLKYZHV-DNQXCXABSA-N 0.000 claims 1
- VTJJWWVIJXQBIQ-DNQXCXABSA-N (3R)-1-[3-[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]phenoxy]propyl]pyrrolidin-3-ol Chemical compound CC1=C(C=CC=C1OCCCN1C[C@@H](CC1)O)C1=CC(=CC=C1)OCCCN1C[C@@H](CC1)O VTJJWWVIJXQBIQ-DNQXCXABSA-N 0.000 claims 1
- IEZQRFAPDCUVGU-RUZDIDTESA-N (3R)-1-[3-[3-[3-[3-[2-(4-chloropyrazol-1-yl)ethylamino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound ClC=1C=NN(C=1)CCNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C IEZQRFAPDCUVGU-RUZDIDTESA-N 0.000 claims 1
- CYNGYKDELPIQQQ-OFSOJUDTSA-N (3R)-1-[3-[3-[3-[3-[[(1R)-2-hydroxy-1-phenylethyl]amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound OC[C@@H](C1=CC=CC=C1)NCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C CYNGYKDELPIQQQ-OFSOJUDTSA-N 0.000 claims 1
- CYNGYKDELPIQQQ-POURPWNDSA-N (3R)-1-[3-[3-[3-[3-[[(1S)-2-hydroxy-1-phenylethyl]amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound OC[C@H](C1=CC=CC=C1)NCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C CYNGYKDELPIQQQ-POURPWNDSA-N 0.000 claims 1
- CMCZELPZYAAQHT-OFSOJUDTSA-N (3R)-1-[3-[3-[3-[3-[[(2R)-2-hydroxy-2-phenylethyl]amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound O[C@@H](CNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)C1=CC=CC=C1 CMCZELPZYAAQHT-OFSOJUDTSA-N 0.000 claims 1
- IIPCFTKEDHLOME-FYBSXPHGSA-N (3R)-1-[3-[3-[3-[3-[[(2S)-2-(3-chloro-4-fluorophenyl)-2-hydroxyethyl]amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound ClC=1C=C(C=CC=1F)[C@@H](CNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)O IIPCFTKEDHLOME-FYBSXPHGSA-N 0.000 claims 1
- CMCZELPZYAAQHT-POURPWNDSA-N (3R)-1-[3-[3-[3-[3-[[(2S)-2-hydroxy-2-phenylethyl]amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound O[C@H](CNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)C1=CC=CC=C1 CMCZELPZYAAQHT-POURPWNDSA-N 0.000 claims 1
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- ADSFSZYYGNVUHL-GDLZYMKVSA-N (3R)-1-[3-[3-[3-[3-[benzyl(2-hydroxyethyl)amino]propoxy]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound C(C1=CC=CC=C1)N(CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)CCO ADSFSZYYGNVUHL-GDLZYMKVSA-N 0.000 claims 1
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Families Citing this family (101)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10745382B2 (en) | 2015-10-15 | 2020-08-18 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| WO2018005374A1 (en) | 2016-06-27 | 2018-01-04 | Chemocentryx, Inc. | Immunomodulator compounds |
| KR20210118240A (ko) | 2016-10-14 | 2021-09-29 | 프리시젼 바이오사이언시스 인코포레이티드 | B형 간염 바이러스 게놈 내의 인식 서열에 대해 특이적인 조작된 메가뉴클레아제 |
| JP7106572B2 (ja) | 2016-12-20 | 2022-07-26 | ブリストル－マイヤーズ スクイブ カンパニー | 免疫調節剤として有用な化合物 |
| WO2018124766A2 (ko) | 2016-12-28 | 2018-07-05 | 주식회사 녹십자랩셀 | 키메라 항원 수용체 및 이를 발현하는 자연 살해 세포 |
| US10654815B2 (en) * | 2016-12-29 | 2020-05-19 | Shenzhen Chipscreen Biosciences Co., Ltd. | Urea compound and preparation method and application thereof |
| EP3601258B1 (en) | 2017-03-27 | 2023-08-30 | Bristol-Myers Squibb Company | Substituted isoquionline derivatives as immunomudulators |
| JOP20180040A1 (ar) | 2017-04-20 | 2019-01-30 | Gilead Sciences Inc | مثبطات pd-1/pd-l1 |
| US11130740B2 (en) | 2017-04-25 | 2021-09-28 | Arbutus Biopharma Corporation | Substituted 2,3-dihydro-1H-indene analogs and methods using same |
| WO2019008156A1 (en) * | 2017-07-07 | 2019-01-10 | Rijksuniversiteit Groningen | INHIBITORS OF PROTEIN / PROTEIN INTERACTION PD-1 / PD-L1 |
| EP3658522B1 (en) | 2017-07-28 | 2021-12-22 | ChemoCentryx, Inc. | Immunomodulator compounds |
| ES2926540T3 (es) | 2017-08-08 | 2022-10-26 | Chemocentryx Inc | Inmunomoduladores macrocíclicos |
| US11649294B2 (en) | 2017-11-14 | 2023-05-16 | GC Cell Corporation | Anti-HER2 antibody or antigen-binding fragment thereof, and chimeric antigen receptor comprising same |
| WO2019098682A1 (ko) | 2017-11-14 | 2019-05-23 | 앱클론(주) | 항-her2 항체 또는 그의 항원 결합 단편, 및 이를 포함하는 키메라 항원 수용체 |
| EP3728282B1 (en) | 2017-12-20 | 2023-11-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 2'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| EP3728283B1 (en) | 2017-12-20 | 2023-11-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 3'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| US11414418B2 (en) | 2018-01-23 | 2022-08-16 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| TWI707849B (zh) | 2018-02-13 | 2020-10-21 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| JP7387616B2 (ja) | 2018-02-22 | 2023-11-28 | ケモセントリックス，インコーポレイティド | Ｐｄ－ｌ１アンタゴニストとしてのインダン－アミン |
| EP3759109B1 (en) | 2018-02-26 | 2023-08-30 | Gilead Sciences, Inc. | Substituted pyrrolizine compounds as hbv replication inhibitors |
| WO2019169123A1 (en) | 2018-03-01 | 2019-09-06 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| US12083118B2 (en) | 2018-03-29 | 2024-09-10 | Arbutus Biopharma Corporation | Substituted 1,1′-biphenyl compounds, analogues thereof, and methods using same |
| EP3774883A1 (en) | 2018-04-05 | 2021-02-17 | Gilead Sciences, Inc. | Antibodies and fragments thereof that bind hepatitis b virus protein x |
| TWI818007B (zh) | 2018-04-06 | 2023-10-11 | 捷克科學院有機化學與生物化學研究所 | 2'3'-環二核苷酸 |
| TW202005654A (zh) | 2018-04-06 | 2020-02-01 | 捷克科學院有機化學與生物化學研究所 | ２，２，─環二核苷酸 |
| TWI833744B (zh) | 2018-04-06 | 2024-03-01 | 捷克科學院有機化學與生物化學研究所 | 3'3'-環二核苷酸 |
| US11142750B2 (en) | 2018-04-12 | 2021-10-12 | Precision Biosciences, Inc. | Optimized engineered meganucleases having specificity for a recognition sequence in the Hepatitis B virus genome |
| CA3093130C (en) | 2018-04-19 | 2023-10-17 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| US20190359645A1 (en) | 2018-05-03 | 2019-11-28 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3'-cyclic dinucleotides comprising carbocyclic nucleotide |
| EP3810109B1 (en) | 2018-05-31 | 2024-08-07 | Peloton Therapeutics, Inc. | Compounds and compositions for inhibiting cd73 |
| TWI809427B (zh) | 2018-07-13 | 2023-07-21 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| CN112424185B (zh) * | 2018-07-13 | 2024-05-17 | 广州丹康医药生物有限公司 | 含苯环的化合物、其制备方法及应用 |
| TWI826492B (zh) | 2018-07-27 | 2023-12-21 | 加拿大商愛彼特生物製藥公司 | 經取代四氫環戊[c]吡咯、經取代二氫吡咯，其類似物及使用其之方法 |
| WO2020028097A1 (en) | 2018-08-01 | 2020-02-06 | Gilead Sciences, Inc. | Solid forms of (r)-11-(methoxymethyl)-12-(3-methoxypropoxy)-3,3-dimethyl-8-0x0-2,3,8,13b-tetrahydro-1h-pyrido[2,1-a]pyrrolo[1,2-c] phthalazine-7-c arboxylic acid |
| CN109305934A (zh) * | 2018-08-07 | 2019-02-05 | 成都海博锐药业有限公司 | 苯醚类衍生物及可药用盐、医药上的用途 |
| CN110872275A (zh) * | 2018-08-31 | 2020-03-10 | 深圳微芯生物科技股份有限公司 | 作为免疫调节剂的联苯化合物及其用途 |
| EP3870566A1 (en) | 2018-10-24 | 2021-09-01 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| ES2979163T3 (es) | 2018-10-31 | 2024-09-24 | Gilead Sciences Inc | Compuestos de 6-azabenzimidazol sustituidos como inhibidores de HPK1 |
| WO2020092528A1 (en) | 2018-10-31 | 2020-05-07 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds having hpk1 inhibitory activity |
| EP3875458A4 (en) | 2018-11-02 | 2022-08-24 | Shanghai Maxinovel Pharmaceuticals Co., Ltd. | DIPHENYLIKE COMPOUNDS, INTERMEDIATE PRODUCTS THEREOF, PREPARATION PROCESS THEREOF, PHARMACEUTICAL COMPOSITION THEREOF AND USES THEREOF |
| TW202415643A (zh) | 2018-12-12 | 2024-04-16 | 加拿大商愛彼特生物製藥公司 | 經取代之芳基甲基脲類及雜芳基甲基脲類、其類似物及其使用方法 |
| EP3908600A1 (en) * | 2019-01-11 | 2021-11-17 | Fundació Institut d'Investigació Biomèdica de Bellvitge (IDIBELL) | Fusion protein with immunosuppressive activity |
| US12318403B2 (en) | 2019-03-07 | 2025-06-03 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2′3′-cyclic dinucleotides and prodrugs thereof |
| WO2020178768A1 (en) | 2019-03-07 | 2020-09-10 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotide analogue comprising a cyclopentanyl modified nucleotide as sting modulator |
| CA3129011C (en) | 2019-03-07 | 2023-12-19 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotides and prodrugs thereof |
| JP2022526960A (ja) | 2019-03-28 | 2022-05-27 | ブリストル－マイヤーズ スクイブ カンパニー | 腫瘍を処置する方法 |
| EP3946625A1 (en) | 2019-03-28 | 2022-02-09 | Bristol-Myers Squibb Company | Methods of treating tumor |
| TW202212339A (zh) | 2019-04-17 | 2022-04-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TW202210480A (zh) | 2019-04-17 | 2022-03-16 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| CN114340633B (zh) | 2019-05-15 | 2025-12-30 | 凯莫森特里克斯股份有限公司 | 用于治疗pd-l1疾病的三芳基化合物 |
| WO2020237081A1 (en) * | 2019-05-21 | 2020-11-26 | Bristol-Myers Squibb Company | Immunomodulators |
| EP3972695A1 (en) | 2019-05-23 | 2022-03-30 | Gilead Sciences, Inc. | Substituted exo-methylene-oxindoles which are hpk1/map4k1 inhibitors |
| WO2020243563A1 (en) | 2019-05-30 | 2020-12-03 | Bristol-Myers Squibb Company | Multi-tumor gene signatures for suitability to immuno-oncology therapy |
| KR20220016157A (ko) | 2019-05-30 | 2022-02-08 | 브리스톨-마이어스 스큅 컴퍼니 | 세포 국재화 시그너쳐 및 조합 요법 |
| CN114127315A (zh) | 2019-05-30 | 2022-03-01 | 百时美施贵宝公司 | 鉴定适合于免疫肿瘤学(i-o)疗法的受试者的方法 |
| WO2020244518A1 (zh) * | 2019-06-04 | 2020-12-10 | 中国科学院上海药物研究所 | 一种具有苄氧基芳环结构的化合物，其制备方法和用途 |
| CA3139242A1 (en) | 2019-06-20 | 2020-12-24 | Viengkham Malathong | Compounds for treatment of pd-l1 diseases |
| CN114206338B (zh) | 2019-07-10 | 2025-12-12 | 凯莫森特里克斯股份有限公司 | 作为pd-l1抑制剂的二氢化茚类 |
| US20220257619A1 (en) | 2019-07-18 | 2022-08-18 | Gilead Sciences, Inc. | Long-acting formulations of tenofovir alafenamide |
| US20220296619A1 (en) | 2019-08-19 | 2022-09-22 | Gilead Sciences, Inc. | Pharmaceutical formulations of tenofovir alafenamide |
| CN111909108B (zh) * | 2019-09-02 | 2023-05-02 | 中国药科大学 | 联苯类化合物及其制备方法和医药用途 |
| US20220348653A1 (en) | 2019-09-22 | 2022-11-03 | Bristol-Myers Squibb Company | Quantitative Spatial Profiling for LAG-3 Antagonist Therapy |
| IL315295A (en) | 2019-09-30 | 2024-10-01 | Gilead Sciences Inc | Hbv vaccines and methods treating hbv |
| JP7642625B2 (ja) * | 2019-10-04 | 2025-03-10 | ブリストル－マイヤーズ スクイブ カンパニー | 免疫調節剤として有用な化合物 |
| US11713307B2 (en) | 2019-10-16 | 2023-08-01 | Chemocentryx, Inc. | Heteroaryl-biphenyl amides for the treatment of PD-L1 diseases |
| PH12022550877A1 (en) | 2019-10-16 | 2023-03-27 | Chemocentryx Inc | Heteroaryl-biphenyl amines for the treatment of pd-l1 diseases |
| CN115942973A (zh) | 2019-11-08 | 2023-04-07 | 百时美施贵宝公司 | 用于黑色素瘤的lag-3拮抗剂疗法 |
| CN116057068A (zh) | 2019-12-06 | 2023-05-02 | 精密生物科学公司 | 对乙型肝炎病毒基因组中的识别序列具有特异性的优化的工程化大范围核酸酶 |
| WO2021188959A1 (en) | 2020-03-20 | 2021-09-23 | Gilead Sciences, Inc. | Prodrugs of 4'-c-substituted-2-halo-2'-deoxyadenosine nucleosides and methods of making and using the same |
| KR20230041654A (ko) | 2020-05-05 | 2023-03-24 | 테온 테라퓨틱스, 인크. | 칸나비노이드 수용체 유형 2 (cb2) 조정제 및 그의 용도 |
| CA3193421A1 (en) | 2020-08-28 | 2022-03-03 | Bristol-Myers Squibb Company | Lag-3 antagonist therapy for hepatocellular carcinoma |
| US20230303700A1 (en) | 2020-08-31 | 2023-09-28 | Bristol-Myers Squibb Company | Cell localization signature and immunotherapy |
| TW202214568A (zh) | 2020-09-09 | 2022-04-16 | 大陸商廣州再極醫藥科技有限公司 | 芳香乙烯類化合物、其製備方法、中間體、藥物組合物及其應用 |
| US11833209B2 (en) | 2020-09-11 | 2023-12-05 | Nammi Therapeutics, Inc. | Formulated and/or co-formulated liposome compositions containing PD-1 antagonist prodrugs useful in the treatment of cancer and methods thereof |
| CA3196496A1 (en) | 2020-10-23 | 2022-04-28 | Laurence David TOMS | Lag-3 antagonist therapy for lung cancer |
| WO2022120179A1 (en) | 2020-12-03 | 2022-06-09 | Bristol-Myers Squibb Company | Multi-tumor gene signatures and uses thereof |
| AU2022246593A1 (en) | 2021-03-29 | 2023-10-12 | Juno Therapeutics, Inc. | Methods for dosing and treatment with a combination of a checkpoint inhibitor therapy and a car t cell therapy |
| CN113135895A (zh) * | 2021-04-30 | 2021-07-20 | 中国药科大学 | 一种新型联苯类衍生物及其制备方法与医药用途 |
| TW202348237A (zh) | 2021-05-13 | 2023-12-16 | 美商基利科學股份有限公司 | TLR8調節化合物及抗HBV siRNA療法之組合 |
| KR20240019283A (ko) | 2021-06-11 | 2024-02-14 | 길리애드 사이언시즈, 인코포레이티드 | Mcl-1 저해제와 항암제의 병용 |
| CA3222752A1 (en) | 2021-06-11 | 2022-12-15 | Gilead Sciences, Inc. | Combination mcl-1 inhibitors with anti-body drug conjugates |
| EP4359415A1 (en) | 2021-06-23 | 2024-05-01 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| CN117377671A (zh) | 2021-06-23 | 2024-01-09 | 吉利德科学公司 | 二酰基甘油激酶调节化合物 |
| CN117480155A (zh) | 2021-06-23 | 2024-01-30 | 吉利德科学公司 | 二酰基甘油激酶调节化合物 |
| EP4359413A1 (en) | 2021-06-23 | 2024-05-01 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| CN115677665B (zh) * | 2021-07-26 | 2024-04-19 | 中国药科大学 | 含联苯类衍生物及其医药用途 |
| WO2023034530A1 (en) | 2021-09-02 | 2023-03-09 | Teon Therapeutics, Inc. | Methods of improving growth and function of immune cells |
| CA3224890A1 (en) | 2021-10-29 | 2023-05-04 | Bristol-Myers Squibb Company | Lag-3 antagonist therapy for hematological cancer |
| WO2023081730A1 (en) | 2021-11-03 | 2023-05-11 | Teon Therapeutics, Inc. | 4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide derivatives as cannabinoid cb2 receptor modulators for the treatment of cancer |
| WO2023097211A1 (en) | 2021-11-24 | 2023-06-01 | The University Of Southern California | Methods for enhancing immune checkpoint inhibitor therapy |
| JP2025503962A (ja) | 2022-01-26 | 2025-02-06 | ブリストル－マイヤーズ スクイブ カンパニー | 肝細胞がんのための併用療法 |
| US20230326022A1 (en) | 2022-04-08 | 2023-10-12 | Bristol-Myers Squibb Company | Machine Learning Identification, Classification, and Quantification of Tertiary Lymphoid Structures |
| WO2024015372A1 (en) | 2022-07-14 | 2024-01-18 | Teon Therapeutics, Inc. | Adenosine receptor antagonists and uses thereof |
| KR20250123912A (ko) | 2022-12-21 | 2025-08-18 | 브리스톨-마이어스 스큅 컴퍼니 | 폐암에 대한 병용 요법 |
| KR20250150141A (ko) | 2023-02-23 | 2025-10-17 | 선샤인 레이크 파르마 컴퍼니 리미티드 | 피리도피리미딘 유도체 및 이의 용도 |
| WO2024196952A1 (en) | 2023-03-20 | 2024-09-26 | Bristol-Myers Squibb Company | Tumor subtype assessment for cancer therapy |
| WO2025240244A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies comprising bulevirtide and lonafarnib for use in the treatment of hepatitis d virus infection |
| WO2025240246A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025240242A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025240243A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with bulevirtide and an inhibitory nucleic acid targeting hepatitis b virus |
| WO2025245489A1 (en) | 2024-05-24 | 2025-11-27 | Bristol-Myers Squibb Company | Treatment of tumors in subjects having fgl-1 positive samples |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU75628A1 (cg-RX-API-DMAC7.html) | 1976-08-19 | 1978-04-13 | ||
| CH654286A5 (de) | 1981-11-04 | 1986-02-14 | Ciba Geigy Ag | Verfahren zur pd-katalysierten arylierung von olefinen mit arylhalogeniden. |
| US6410690B1 (en) | 1995-06-07 | 2002-06-25 | Medarex, Inc. | Therapeutic compounds comprised of anti-Fc receptor antibodies |
| US5811097A (en) | 1995-07-25 | 1998-09-22 | The Regents Of The University Of California | Blockade of T lymphocyte down-regulation associated with CTLA-4 signaling |
| US5977117A (en) | 1996-01-05 | 1999-11-02 | Texas Biotechnology Corporation | Substituted phenyl compounds and derivatives thereof that modulate the activity of endothelin |
| US5922845A (en) | 1996-07-11 | 1999-07-13 | Medarex, Inc. | Therapeutic multispecific compounds comprised of anti-Fcα receptor antibodies |
| JPWO2004007439A1 (ja) | 2002-07-10 | 2005-11-10 | 住友製薬株式会社 | ビアリール誘導体 |
| WO2004080377A2 (en) | 2003-03-11 | 2004-09-23 | Neurosearch A/S | Kcnq channel modulating compounds and their pharmaceutical use |
| JP2005179281A (ja) | 2003-12-19 | 2005-07-07 | Sumitomo Pharmaceut Co Ltd | ビフェニル化合物 |
| WO2005080367A1 (en) | 2004-02-12 | 2005-09-01 | Pharmagene Laboratories Limited | Ep2 receptor agonists |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| JP2009505973A (ja) | 2005-08-09 | 2009-02-12 | アステランド ユーケイ リミテッド | Ｅｐ２受容体アゴニスト |
| TW200815377A (en) | 2006-04-24 | 2008-04-01 | Astellas Pharma Inc | Oxadiazolidinedione compound |
| EP2139843B1 (en) | 2007-04-16 | 2013-12-25 | Amgen, Inc | Substituted biphenyl phenoxy-, thiophenyl- and aminophenylpropanoic acid gpr40 modulators |
| TW200932219A (en) | 2007-10-24 | 2009-08-01 | Astellas Pharma Inc | Oxadiazolidinedione compound |
| TWI444467B (zh) | 2010-05-27 | 2014-07-11 | Angus Chemical | 用於液體碳氫化合物及其他燃料與油之標記物化合物 |
| CN105705489B (zh) | 2013-09-04 | 2019-04-26 | 百时美施贵宝公司 | 用作免疫调节剂的化合物 |
| US9850225B2 (en) * | 2014-04-14 | 2017-12-26 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| AU2016286115B9 (en) * | 2015-06-29 | 2021-02-04 | Vanderbilt University | Intravenous administration of citrulline during surgery |
| US10745382B2 (en) | 2015-10-15 | 2020-08-18 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| JP7168551B2 (ja) | 2016-07-08 | 2022-11-09 | ブリストル－マイヤーズ スクイブ カンパニー | 免疫調節剤として有用な１，３－ジヒドロキシフェニル誘導体 |
| CA3030773A1 (en) * | 2016-08-03 | 2018-02-08 | Arising International, Inc. | Symmetric or semi-symmetric compounds useful as immunomodulators |
-
2017
- 2017-08-29 US US15/689,115 patent/US10144706B2/en active Active
- 2017-08-30 JP JP2019511947A patent/JP7155110B2/ja active Active
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- 2017-08-30 CA CA3035697A patent/CA3035697A1/en not_active Abandoned
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- 2017-08-30 CN CN201780067319.8A patent/CN109863146B/zh active Active
- 2017-08-30 ES ES17764981T patent/ES2919298T3/es active Active
- 2017-08-30 MX MX2019002356A patent/MX2019002356A/es unknown
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