ES2462715T3 - Compuestos y métodos de uso - Google Patents
Compuestos y métodos de uso Download PDFInfo
- Publication number
- ES2462715T3 ES2462715T3 ES09837907.6T ES09837907T ES2462715T3 ES 2462715 T3 ES2462715 T3 ES 2462715T3 ES 09837907 T ES09837907 T ES 09837907T ES 2462715 T3 ES2462715 T3 ES 2462715T3
- Authority
- ES
- Spain
- Prior art keywords
- thiazol
- benzo
- ylcarbamoyl
- tetrahydroquinolin
- group
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 199
- 238000000034 method Methods 0.000 title claims description 97
- -1 - (CH2) 1-4-phenyl Chemical group 0.000 claims abstract description 253
- 125000001424 substituent group Chemical group 0.000 claims abstract description 58
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 48
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 47
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 47
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 47
- 150000002367 halogens Chemical class 0.000 claims abstract description 44
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 43
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 43
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract description 38
- 125000004474 heteroalkylene group Chemical group 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 37
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 36
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 36
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 35
- 125000004429 atom Chemical group 0.000 claims abstract description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 24
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 20
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims abstract description 20
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 17
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 12
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 12
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims abstract description 8
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims abstract description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 8
- 229910021481 rutherfordium Inorganic materials 0.000 claims abstract description 8
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000006585 (C6-C10) arylene group Chemical group 0.000 claims abstract description 6
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 63
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 49
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- 201000010099 disease Diseases 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 201000011510 cancer Diseases 0.000 claims description 31
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims description 29
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 206010033128 Ovarian cancer Diseases 0.000 claims description 12
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 10
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 10
- XBBJQSQPJIYQNM-UHFFFAOYSA-N 2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-5-phenoxy-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1N=C(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)SC=1OC1=CC=CC=C1 XBBJQSQPJIYQNM-UHFFFAOYSA-N 0.000 claims description 9
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 9
- SSVPVQYXJINXMD-UHFFFAOYSA-N 2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-2,3-dihydroindol-6-yl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCC3=CC=2)=N1 SSVPVQYXJINXMD-UHFFFAOYSA-N 0.000 claims description 8
- XNAZSUQOXPFRCI-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-[1-(1,3-thiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-1,3-thiazole-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C(O)=O)N=C(C=2C=C3N(C(=O)NC=4SC=CN=4)CCCC3=CC=2)S1 XNAZSUQOXPFRCI-UHFFFAOYSA-N 0.000 claims description 8
- KSTDEFWREQYWLG-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-[1-[(5-methyl-1,3-thiazol-2-yl)carbamoyl]-3,4-dihydro-2h-quinolin-7-yl]-1,3-thiazole-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C(O)=O)N=C(C=2C=C3N(C(=O)NC=4SC(C)=CN=4)CCCC3=CC=2)S1 KSTDEFWREQYWLG-UHFFFAOYSA-N 0.000 claims description 8
- 206010005003 Bladder cancer Diseases 0.000 claims description 8
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 8
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- 208000014829 head and neck neoplasm Diseases 0.000 claims description 8
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- 208000020816 lung neoplasm Diseases 0.000 claims description 8
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 8
- NFBBOKMAQZIDEG-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-[1-[(4-methyl-1,3-thiazol-2-yl)carbamoyl]-3,4-dihydro-2h-quinolin-7-yl]-1,3-thiazole-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C(O)=O)N=C(C=2C=C3N(C(=O)NC=4SC=C(C)N=4)CCCC3=CC=2)S1 NFBBOKMAQZIDEG-UHFFFAOYSA-N 0.000 claims description 7
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 7
- 230000001154 acute effect Effects 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- MPBQJXNTYAFDCG-UHFFFAOYSA-N 2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)=N1 MPBQJXNTYAFDCG-UHFFFAOYSA-N 0.000 claims description 6
- ACWUWQFNFCECSG-UHFFFAOYSA-N 2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-5-(3-phenoxypropyl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1N=C(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)SC=1CCCOC1=CC=CC=C1 ACWUWQFNFCECSG-UHFFFAOYSA-N 0.000 claims description 6
- ATYICJLSTAZWCH-UHFFFAOYSA-N 2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-5-(4-phenylphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1N=C(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)SC=1C(C=C1)=CC=C1C1=CC=CC=C1 ATYICJLSTAZWCH-UHFFFAOYSA-N 0.000 claims description 6
- KSDFWQKMVJWLGC-UHFFFAOYSA-N 2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-5-[3-(4-pyrazolo[3,4-d]pyrimidin-1-ylphenoxy)propyl]-1,3-thiazole-4-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)N3CCCC4=CC=C(C=C43)C3=NC(=C(S3)CCCOC=3C=CC(=CC=3)N3C4=NC=NC=C4C=N3)C(=O)O)=NC2=C1 KSDFWQKMVJWLGC-UHFFFAOYSA-N 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 6
- 208000025997 central nervous system neoplasm Diseases 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 210000003734 kidney Anatomy 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical group O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 5
- DTCSCHOGNLBRFF-NTCAYCPXSA-N 2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-5-[(e)-2-phenylethenyl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1N=C(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)SC=1\C=C\C1=CC=CC=C1 DTCSCHOGNLBRFF-NTCAYCPXSA-N 0.000 claims description 5
- OUFDDBHWDFQHAM-UHFFFAOYSA-N 2-[4-(1,3-benzothiazol-2-ylcarbamoyl)-2,3-dihydro-1,4-benzoxazin-6-yl]-5-phenyl-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1N=C(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCOC3=CC=2)SC=1C1=CC=CC=C1 OUFDDBHWDFQHAM-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 208000034578 Multiple myelomas Diseases 0.000 claims description 5
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 5
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
- 208000017733 acquired polycythemia vera Diseases 0.000 claims description 5
- 208000024207 chronic leukemia Diseases 0.000 claims description 5
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- 208000003747 lymphoid leukemia Diseases 0.000 claims description 5
- 201000001441 melanoma Diseases 0.000 claims description 5
- 229940081066 picolinic acid Drugs 0.000 claims description 5
- 208000037244 polycythemia vera Diseases 0.000 claims description 5
- 201000011549 stomach cancer Diseases 0.000 claims description 5
- HRNHYKJWRGNWJS-UHFFFAOYSA-N 6-[4-(1,3-benzothiazol-2-ylcarbamoyl)-1-methyl-2,3-dihydroquinoxalin-6-yl]pyridine-2-carboxylic acid Chemical compound C=1C=C2N(C)CCN(C(=O)NC=3SC4=CC=CC=C4N=3)C2=CC=1C1=CC=CC(C(O)=O)=N1 HRNHYKJWRGNWJS-UHFFFAOYSA-N 0.000 claims description 4
- 208000006468 Adrenal Cortex Neoplasms Diseases 0.000 claims description 4
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
- 206010005949 Bone cancer Diseases 0.000 claims description 4
- 208000018084 Bone neoplasm Diseases 0.000 claims description 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 4
- 206010006143 Brain stem glioma Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 4
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 4
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 4
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 4
- 208000017604 Hodgkin disease Diseases 0.000 claims description 4
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 4
- 206010061252 Intraocular melanoma Diseases 0.000 claims description 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
- 208000032271 Malignant tumor of penis Diseases 0.000 claims description 4
- 208000003445 Mouth Neoplasms Diseases 0.000 claims description 4
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
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- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
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- WWSKHLBGFIOZBT-UHFFFAOYSA-N 6-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-3-phenylpyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)=CC=C1C1=CC=CC=C1 WWSKHLBGFIOZBT-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
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- RSSPYPZTSOSDNQ-UHFFFAOYSA-N 2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-5-(3-fluoro-4-propan-2-yloxyphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound C1=C(F)C(OC(C)C)=CC=C1C1=C(C(O)=O)N=C(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)S1 RSSPYPZTSOSDNQ-UHFFFAOYSA-N 0.000 claims description 2
- FMPRRCSMVBVPKG-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-ylcarbamoyl)-2,3-dihydro-1,4-benzoxazin-6-yl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C=C3N(C(=O)NC=4OC5=CC=CC=C5N=4)CCOC3=CC=2)=N1 FMPRRCSMVBVPKG-UHFFFAOYSA-N 0.000 claims description 2
- BYMHFFYJCHILSC-UHFFFAOYSA-N 2-[4-(quinolin-2-ylcarbamoyl)-2,3-dihydro-1,4-benzoxazin-6-yl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C=C3N(C(=O)NC=4N=C5C=CC=CC5=CC=4)CCOC3=CC=2)=N1 BYMHFFYJCHILSC-UHFFFAOYSA-N 0.000 claims description 2
- AYINEXHHTDRALS-UHFFFAOYSA-N 3-[2-(3-aminophenoxy)ethoxy]-6-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]pyridine-2-carboxylic acid Chemical compound NC1=CC=CC(OCCOC=2C(=NC(=CC=2)C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)C(O)=O)=C1 AYINEXHHTDRALS-UHFFFAOYSA-N 0.000 claims description 2
- RCVLLTPEOVNERE-UHFFFAOYSA-N 3-[2-[4-(aminomethyl)phenoxy]ethoxy]-6-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]pyridine-2-carboxylic acid Chemical compound C1=CC(CN)=CC=C1OCCOC1=CC=C(C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)N=C1C(O)=O RCVLLTPEOVNERE-UHFFFAOYSA-N 0.000 claims description 2
- CGWQYFHTZRBUAD-UHFFFAOYSA-N 3-[3-[(3-aminophenoxy)methyl]phenyl]-6-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]pyridine-2-carboxylic acid Chemical compound NC1=CC=CC(OCC=2C=C(C=CC=2)C=2C(=NC(=CC=2)C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)C(O)=O)=C1 CGWQYFHTZRBUAD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- TZQOBUMCDIUNCD-UHFFFAOYSA-N 5-[3-(3-aminophenoxy)propyl]-2-[1-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-2h-quinolin-7-yl]-1,3-thiazole-4-carboxylic acid Chemical compound NC1=CC=CC(OCCCC2=C(N=C(S2)C=2C=C3N(C(=O)NC=4SC5=CC=CC=C5N=4)CCCC3=CC=2)C(O)=O)=C1 TZQOBUMCDIUNCD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
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- C—CHEMISTRY; METALLURGY
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| RU2550346C2 (ru) * | 2013-09-26 | 2015-05-10 | Общество с ограниченной ответственностью "Отечественные Фармацевтические Технологии" ООО"ФармТех" | Новые химические соединения (варианты) и их применение для лечения онкологических заболеваний |
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| WO2015116735A1 (en) | 2014-01-28 | 2015-08-06 | Mayo Foundation For Medical Education And Research | Methods and combinations for killing senescent cells and for treating senescence-associated diseases and disorders |
| EP3099380B1 (en) | 2014-01-28 | 2021-08-11 | Buck Institute for Research on Aging | Methods and compositions for killing senescent cells and for treating senescence-associated diseases and disorders |
| CN103804367B (zh) * | 2014-02-28 | 2016-09-14 | 天津药物研究院 | 苯并氮杂卓衍生物、其制备方法和用途 |
| EP3125884B1 (en) | 2014-04-04 | 2019-11-06 | The Regents of the University of Michigan | Small molecule inhibitors of mcl-1 and uses thereof |
| US11331328B2 (en) | 2014-05-05 | 2022-05-17 | Bioventures, Llc | Compositions and methods for inhibiting antiapoptotic Bcl-2 proteins as anti-aging agents |
| JP6560335B2 (ja) * | 2014-07-08 | 2019-08-14 | ダウ アグロサイエンシィズ エルエルシー | ３−ヒドロキシピコリン酸の製造方法 |
| AU2015292710A1 (en) | 2014-07-22 | 2017-02-16 | Bioventures, Llc. | Compositions and methods for selectively depleting senescent cells |
| EP3174890B1 (de) * | 2014-07-28 | 2019-03-13 | Merck Patent GmbH | Metallkomplexe |
| PL3200786T3 (pl) | 2014-10-03 | 2020-03-31 | Novartis Ag | Zastosowanie pochodnych pirydylowych o skondensowanym układzie bicyklicznym jako inhibitorów fgfr4 |
| AU2015360621A1 (en) * | 2014-12-09 | 2017-06-29 | Abbvie Inc. | Bcl-xL inhibitory compounds and antibody drug conjugates including the same |
| WO2016131100A1 (en) * | 2015-02-18 | 2016-08-25 | The Walter And Eliza Hall Institute Of Medical Research | Methods of treating infectious diseases |
| US10195213B2 (en) | 2015-03-13 | 2019-02-05 | Unity Biotechnology, Inc. | Chemical entities that kill senescent cells for use in treating age-related disease |
| US9802917B2 (en) | 2015-03-25 | 2017-10-31 | Novartis Ag | Particles of N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide |
| EP3407974A4 (en) | 2016-01-29 | 2019-08-28 | The Regents Of The University Of Michigan | Amlexanox Analogs |
| NZ757763A (en) | 2016-03-28 | 2025-07-25 | Presage Biosciences Inc | Pharmaceutical combinations for the treatment of cancer |
| EP3445452A4 (en) | 2016-04-21 | 2019-10-30 | BioVentures, LLC | COMPOUNDS FOR INDUCING THE DEGRADATION OF ANTIAPOPTOTIC PROTEINS OF THE BCL-2 FAMILY AND USES THEREOF |
| US10779980B2 (en) | 2016-04-27 | 2020-09-22 | Synerz Medical, Inc. | Intragastric device for treating obesity |
| CN108251377B (zh) * | 2018-01-16 | 2021-08-27 | 内蒙古大学 | 利用携带Xist Tale抑制性转录因子R6的R6-MEF制备饲养层细胞的方法 |
| ES3041854T3 (en) | 2018-01-22 | 2025-11-17 | Bioventures Llc | Bcl-2 proteins degraders for cancer treatment |
| US12084423B2 (en) | 2018-05-18 | 2024-09-10 | Bioventures, Llc | Piperlongumine analogues and uses thereof |
| EP3705109A1 (en) | 2019-03-05 | 2020-09-09 | Greenaltech, S.L. | Carotenoids in the treatment of senescence-related diseases |
| CN115413277B (zh) * | 2020-04-20 | 2023-08-01 | 深圳市塔吉瑞生物医药有限公司 | 吡嗪取代的烟酰胺的固体形式及其制备和用途 |
| WO2021233948A1 (en) | 2020-05-19 | 2021-11-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method to treat a pathogen lung infection |
| EP4175644A1 (en) | 2020-07-06 | 2023-05-10 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Combination of antineoplastic antibiotics and bcl-2 inhibitors for the treatment of npm-1-driven acute myeloid leukemia (aml) |
| US20240269304A1 (en) | 2020-11-24 | 2024-08-15 | Novartis Ag | Bcl-xl inhibitor antibody-drug conjugates and methods of use thereof |
| WO2022169780A1 (en) | 2021-02-02 | 2022-08-11 | Les Laboratoires Servier | Selective bcl-xl protac compounds and methods of use |
| WO2023172958A1 (en) * | 2022-03-08 | 2023-09-14 | Onkosxcel Therapeutics, Llc | Stable formulations of talabostat |
| TW202339721A (zh) * | 2022-03-31 | 2023-10-16 | 英屬開曼群島商百濟神州有限公司 | Bcl-xL抑制劑 |
| EP4525927A1 (en) | 2022-05-20 | 2025-03-26 | Novartis AG | Antibody-drug conjugates of antineoplastic compounds and methods of use thereof |
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| AU2023271885A1 (en) | 2022-05-20 | 2024-12-12 | Les Laboratoires Servier | Epha2 bcl-xl inhibitor antibody-drug conjugates and methods of use thereof |
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| WO2025111450A1 (en) | 2023-11-22 | 2025-05-30 | Les Laboratoires Servier | Anti-cd74 antibody-drug conjugates and methods of use thereof |
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| DE19929785A1 (de) * | 1999-06-29 | 2001-01-04 | Bayer Ag | Tetrahydrochinolinyl-6-methyldihydrothiadiazinon-Derivate und ihre Verwendung |
| SK12712002A3 (sk) | 2000-02-07 | 2003-02-04 | Abbott Gmbh & Co. Kg | Deriváty 2-benzotiazolylmočoviny a ich použitie ako inhibítorov proteínkináz |
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| WO2007026920A2 (en) * | 2005-09-02 | 2007-03-08 | Astellas Pharma Inc. | Amide derivatives as rock inhibitors |
| AU2007282535B9 (en) | 2006-08-08 | 2013-06-20 | Chugai Seiyaku Kabushiki Kaisha | Pyrimidine derivative as PI3K inhibitor and use thereof |
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| JP5683484B2 (ja) | 2015-03-11 |
| CA2747161C (en) | 2017-07-18 |
| US20140005190A1 (en) | 2014-01-02 |
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