CA3080900C - Pharmaceutical composition for preventing or treating acute myeloid leukemia or metastatic breast cancer - Google Patents
Pharmaceutical composition for preventing or treating acute myeloid leukemia or metastatic breast cancer Download PDFInfo
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- CA3080900C CA3080900C CA3080900A CA3080900A CA3080900C CA 3080900 C CA3080900 C CA 3080900C CA 3080900 A CA3080900 A CA 3080900A CA 3080900 A CA3080900 A CA 3080900A CA 3080900 C CA3080900 C CA 3080900C
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- Prior art keywords
- compound
- imino
- ethoxy
- flt3
- dihydrochloride
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- 208000031261 Acute myeloid leukaemia Diseases 0.000 title claims abstract description 32
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 title claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 24
- 206010055113 Breast cancer metastatic Diseases 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 claims abstract description 5
- 101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 150000004702 methyl esters Chemical group 0.000 claims description 2
- JEAXKSLIAZCKEF-YRZTTZRYSA-N CN1CCN(CCO/N=C(\C2=CC=CC=C2N2)/C\2=C(\C2=CC(C(OC)=O)=CC=C2N2)/C2=O)CC1 Chemical compound CN1CCN(CCO/N=C(\C2=CC=CC=C2N2)/C\2=C(\C2=CC(C(OC)=O)=CC=C2N2)/C2=O)CC1 JEAXKSLIAZCKEF-YRZTTZRYSA-N 0.000 claims 1
- CRDNMYFJWFXOCH-YPKPFQOOSA-N (3z)-3-(3-oxo-1h-indol-2-ylidene)-1h-indol-2-one Chemical class N/1C2=CC=CC=C2C(=O)C\1=C1/C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-YPKPFQOOSA-N 0.000 abstract description 25
- 230000000694 effects Effects 0.000 abstract description 18
- 239000004480 active ingredient Substances 0.000 abstract description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 94
- 239000000047 product Substances 0.000 description 73
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 45
- 238000005160 1H NMR spectroscopy Methods 0.000 description 41
- -1 piperazinyl-quinazoline compound Chemical class 0.000 description 35
- 210000004027 cell Anatomy 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000126 substance Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
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- 150000002367 halogens Chemical group 0.000 description 12
- 230000003389 potentiating effect Effects 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
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- 229940126639 Compound 33 Drugs 0.000 description 9
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
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- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 8
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229940126086 compound 21 Drugs 0.000 description 8
- 238000000034 method Methods 0.000 description 8
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- HBDSHCUSXQATPO-BGBJRWHRSA-N indirubin-3'-monoxime Chemical class O=C/1NC2=CC=CC=C2C\1=C\1/C(=N/O)/C2=CC=CC=C2N/1 HBDSHCUSXQATPO-BGBJRWHRSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
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- 125000005999 2-bromoethyl group Chemical group 0.000 description 5
- CRDNMYFJWFXOCH-BUHFOSPRSA-N Couroupitine B Natural products N\1C2=CC=CC=C2C(=O)C/1=C1/C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-BUHFOSPRSA-N 0.000 description 5
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- CRDNMYFJWFXOCH-UHFFFAOYSA-N isoindigotin Natural products N1C2=CC=CC=C2C(=O)C1=C1C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 4
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- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D403/14—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 three or more hetero rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2017-0144142 | 2017-10-31 | ||
| KR20170144142 | 2017-10-31 | ||
| PCT/KR2018/013051 WO2019088677A1 (ko) | 2017-10-31 | 2018-10-30 | 급성 골수성 백혈병 또는 전이성 유방암의 예방 또는 치료용 약제학적 조성물 |
Publications (2)
| Publication Number | Publication Date |
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| CA3080900A1 CA3080900A1 (en) | 2019-05-09 |
| CA3080900C true CA3080900C (en) | 2022-10-25 |
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|---|---|---|---|
| CA3080900A Active CA3080900C (en) | 2017-10-31 | 2018-10-30 | Pharmaceutical composition for preventing or treating acute myeloid leukemia or metastatic breast cancer |
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| Country | Link |
|---|---|
| US (1) | US11370779B2 (enExample) |
| EP (1) | EP3705474A4 (enExample) |
| JP (1) | JP7005779B2 (enExample) |
| KR (1) | KR102247795B1 (enExample) |
| CN (1) | CN111542513A (enExample) |
| AU (1) | AU2018358582B2 (enExample) |
| BR (1) | BR112020008499A2 (enExample) |
| CA (1) | CA3080900C (enExample) |
| MX (1) | MX2020004374A (enExample) |
| PH (1) | PH12020550491A1 (enExample) |
| RU (1) | RU2763346C2 (enExample) |
| WO (1) | WO2019088677A1 (enExample) |
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| WO2020216661A1 (en) | 2019-04-26 | 2020-10-29 | Unilever Plc | Hair conditioning composition |
| CN110305056A (zh) * | 2019-05-22 | 2019-10-08 | 西北大学 | 靛玉红新衍生物及其药用用途 |
| EP4010337A4 (en) * | 2019-11-04 | 2023-08-23 | CK Regeon Inc. | COMPOSITIONS AND METHODS FOR SUPPRESSING AND/OR TREATING NEURODEGENERATIVE DISEASES AND/OR ASSOCIATED CLINICAL CONDITION |
| WO2021112626A1 (ko) * | 2019-12-06 | 2021-06-10 | 주식회사 펠레메드 | 신규한 인디루빈 유도체 및 이의 용도 |
| KR102443617B1 (ko) * | 2019-12-06 | 2022-09-16 | 광주과학기술원 | 근감소증 또는 근위축증의 예방 또는 치료용 약제학적 조성물 |
| KR20210106155A (ko) | 2020-02-20 | 2021-08-30 | 한국과학기술원 | Ash1l 히스톤 메틸화 효소 활성을 억제하는 페닐카르보노히드라조노일 디시아나이드 유도체 화합물을 포함하는 백혈병의 예방 또는 치료용 조성물 |
| KR102325607B1 (ko) | 2020-02-20 | 2021-11-12 | 한국과학기술원 | Ash1l 히스톤 메틸화 효소 활성을 억제하는 벤조퓨란-피라졸 유도체 화합물을 포함하는 백혈병의 예방 또는 치료용 조성물 |
| KR102278176B1 (ko) | 2020-02-20 | 2021-07-16 | 한국과학기술원 | Ash1l 히스톤 메틸화 효소 활성을 억제하는 벤조디옥솔 유도체 화합물을 포함하는 백혈병의 예방 또는 치료용 조성물 |
| US20220079934A1 (en) * | 2020-09-17 | 2022-03-17 | Arog Pharmaceuticals, Inc. | Crenolanib for treating pain |
| KR102744517B1 (ko) * | 2022-02-14 | 2024-12-19 | 주식회사 펠레메드 | 신규한 헤테로비시클릭 잔기를 갖는 인디루빈 유도체 및 이의 용도 |
| WO2024181799A1 (ko) * | 2023-02-28 | 2024-09-06 | 주식회사 씨케이리제온 | 신규한 인돌린 유도체 및 이의 용도 |
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| IL145743A0 (en) * | 1999-04-12 | 2002-07-25 | Gerhard Eisenbrand | Indigoid bisindole derivatives |
| FR2850652B1 (fr) * | 2003-01-31 | 2008-05-30 | Aventis Pharma Sa | Nouveaux derives d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| KR100588803B1 (ko) | 2004-01-27 | 2006-06-12 | 학교법인조선대학교 | 암세포주에 항암활성을 지닌 인디루빈 유도체 |
| US8552053B2 (en) * | 2005-12-23 | 2013-10-08 | Centre National De La Recherche Scientifique | 7-substituted indirubin-3′oximes and their applications |
| ATE529402T1 (de) | 2008-08-01 | 2011-11-15 | Centre Nat Rech Scient | 3',6-substituierte indirubine und ihre biologischen anwendungen |
| KR101180030B1 (ko) | 2010-02-05 | 2012-09-05 | 광주과학기술원 | 사이클린-의존적 키나제 저해제로서 항암 활성을 지닌 인디루빈-3'-옥심 유도체 |
| EP2518139A1 (en) * | 2011-04-27 | 2012-10-31 | Universitätsklinikum Jena | Use of indirubin derivatives for producing pluripotent stem cells |
| US10435367B2 (en) * | 2013-03-14 | 2019-10-08 | City Of Hope | Indirubin derivatives, and uses thereof |
| EP2827869A4 (en) | 2012-03-23 | 2015-09-23 | Dennis Brown | COMPOSITIONS AND METHODS FOR IMPROVING THE THERAPEUTIC BENEFIT OF INDIRUBIN AND ANALOGUE THEREOF, WITH MEISOINDIGO |
| EP2970310B1 (en) * | 2013-03-14 | 2020-11-11 | City of Hope | 5-bromo-indirubins |
| US20150259288A1 (en) | 2014-03-14 | 2015-09-17 | City Of Hope | 5-bromo-indirubins |
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| RU2763346C2 (ru) | 2021-12-28 |
| KR20190049584A (ko) | 2019-05-09 |
| BR112020008499A2 (pt) | 2020-10-20 |
| CA3080900A1 (en) | 2019-05-09 |
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| US11370779B2 (en) | 2022-06-28 |
| EP3705474A4 (en) | 2021-06-09 |
| MX2020004374A (es) | 2020-11-11 |
| KR102247795B9 (ko) | 2023-04-12 |
| CN111542513A (zh) | 2020-08-14 |
| PH12020550491A1 (en) | 2021-01-11 |
| WO2019088677A1 (ko) | 2019-05-09 |
| AU2018358582A1 (en) | 2020-05-07 |
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