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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| KR102320547B1 (ko) * | 2015-06-29 | 2021-11-01 | 반더빌트유니버시티 | 수술 동안의 시트룰린의 정맥내 투여 |
| US10745382B2 (en) * | 2015-10-15 | 2020-08-18 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| EA201990221A1 (ru) | 2016-07-08 | 2019-06-28 | Бристол-Маерс Сквибб Компани | 1,3-дигидроксифенильные производные, применимые в качестве иммуномодуляторов |
| JP2019530732A (ja) | 2016-08-03 | 2019-10-24 | アライジング・インターナショナル・インコーポレイテッドＡｒｉｓｉｎｇ Ｉｎｔｅｒｎａｔｉｏｎａｌ， Ｉｎｃ． | 免疫モジュレータとして有用な対称または半対称化合物 |
-
2017
- 2017-08-29 US US15/689,115 patent/US10144706B2/en active Active
- 2017-08-30 CA CA3035697A patent/CA3035697A1/en not_active Abandoned
- 2017-08-30 ES ES17764981T patent/ES2919298T3/es active Active
- 2017-08-30 BR BR112019004100A patent/BR112019004100A2/pt not_active Application Discontinuation
- 2017-08-30 WO PCT/US2017/049252 patent/WO2018044963A1/en not_active Ceased
- 2017-08-30 MA MA046091A patent/MA46091A/fr unknown
- 2017-08-30 AR ARP170102407A patent/AR109471A1/es unknown
- 2017-08-30 EP EP17764981.1A patent/EP3507284B1/en active Active
- 2017-08-30 SG SG11201901700UA patent/SG11201901700UA/en unknown
- 2017-08-30 AU AU2017319323A patent/AU2017319323A1/en not_active Abandoned
- 2017-08-30 EA EA201990495A patent/EA201990495A1/ru unknown
- 2017-08-30 MX MX2019002356A patent/MX2019002356A/es unknown
- 2017-08-30 TW TW106129492A patent/TW201815764A/zh unknown
- 2017-08-30 KR KR1020197008795A patent/KR102497068B1/ko active Active
- 2017-08-30 JP JP2019511947A patent/JP7155110B2/ja active Active
- 2017-08-30 CN CN201780067319.8A patent/CN109863146B/zh active Active
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