MX2015004465A - Indolinas. - Google Patents
Indolinas.Info
- Publication number
- MX2015004465A MX2015004465A MX2015004465A MX2015004465A MX2015004465A MX 2015004465 A MX2015004465 A MX 2015004465A MX 2015004465 A MX2015004465 A MX 2015004465A MX 2015004465 A MX2015004465 A MX 2015004465A MX 2015004465 A MX2015004465 A MX 2015004465A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- acceptable salt
- phenyl
- aryl
- Prior art date
Links
- 150000002476 indolines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- 150000003839 salts Chemical class 0.000 claims abstract description 92
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 24
- 201000011510 cancer Diseases 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 65
- -1 (S) -2-methylamino-propionylamino Chemical group 0.000 claims description 57
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- ODUZJBKKYBQIBX-UHFFFAOYSA-N 2,6-difluoroaniline Chemical compound NC1=C(F)C=CC=C1F ODUZJBKKYBQIBX-UHFFFAOYSA-N 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 8
- NNLWQJXKIXPTCK-UHFFFAOYSA-N (5-fluoro-2-methylphenyl)methanamine;hydrochloride Chemical compound Cl.CC1=CC=C(F)C=C1CN NNLWQJXKIXPTCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- WHZUDFCJBPJMBV-QVVOIHHZSA-N Cl.CN[C@@H](C)C(=O)N[C@H](C(=O)N1[C@@H](Cc2ccccc12)C(N)=O)c1ccccc1 Chemical compound Cl.CN[C@@H](C)C(=O)N[C@H](C(=O)N1[C@@H](Cc2ccccc12)C(N)=O)c1ccccc1 WHZUDFCJBPJMBV-QVVOIHHZSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- MIGUACSHWHEKTK-GKCIPKSASA-N CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](Cc2ccccc12)C(=O)Nc1c(F)cccc1F Chemical compound CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](Cc2ccccc12)C(=O)Nc1c(F)cccc1F MIGUACSHWHEKTK-GKCIPKSASA-N 0.000 claims description 3
- SJCSWALYIRCORO-CQDKDKBSSA-N CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](Cc2ccccc12)C(O)=O Chemical compound CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](Cc2ccccc12)C(O)=O SJCSWALYIRCORO-CQDKDKBSSA-N 0.000 claims description 3
- 125000004431 deuterium atom Chemical group 0.000 claims description 3
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical group CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 3
- HZGCTAZDCKDJIJ-HJFUZJNISA-N Cl.CN[C@@H](C)C(=O)N[C@H](C(=O)N1[C@@H](Cc2ccccc12)C(=O)Nc1ccccc1)c1ccccc1 Chemical compound Cl.CN[C@@H](C)C(=O)N[C@H](C(=O)N1[C@@H](Cc2ccccc12)C(=O)Nc1ccccc1)c1ccccc1 HZGCTAZDCKDJIJ-HJFUZJNISA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- BRAIPJPEKYOWOF-HSQYWUDLSA-N CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](Cc2ccccc12)C(=O)NCc1ccccc1 Chemical compound CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](Cc2ccccc12)C(=O)NCc1ccccc1 BRAIPJPEKYOWOF-HSQYWUDLSA-N 0.000 claims 1
- MQXBWRKEJIVKQK-RZDWPUGNSA-N CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](Cc2ccccc12)C(=O)Nc1ccccc1C(=O)c1ccccc1 Chemical compound CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](Cc2ccccc12)C(=O)Nc1ccccc1C(=O)c1ccccc1 MQXBWRKEJIVKQK-RZDWPUGNSA-N 0.000 claims 1
- ZESHOXYMIFEAJJ-CUEVJCNZSA-N Cl.CN[C@@H](C)C(=O)N[C@H](C(=O)N1[C@@H](Cc2ccccc12)C(=O)NCc1cc(F)ccc1C)c1ccccc1 Chemical compound Cl.CN[C@@H](C)C(=O)N[C@H](C(=O)N1[C@@H](Cc2ccccc12)C(=O)NCc1cc(F)ccc1C)c1ccccc1 ZESHOXYMIFEAJJ-CUEVJCNZSA-N 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 235000019439 ethyl acetate Nutrition 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 229910001868 water Inorganic materials 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- TUMCWFMHZOUPDA-UHFFFAOYSA-N 2-ethylsulfanyl-1,3-benzothiazol-6-amine Chemical compound C1=C(N)C=C2SC(SCC)=NC2=C1 TUMCWFMHZOUPDA-UHFFFAOYSA-N 0.000 description 12
- 101100111638 Arabidopsis thaliana BIR2 gene Proteins 0.000 description 12
- 108091007065 BIRCs Proteins 0.000 description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 102000050257 X-Linked Inhibitor of Apoptosis Human genes 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 102000011727 Caspases Human genes 0.000 description 11
- 108010076667 Caspases Proteins 0.000 description 11
- 108700031544 X-Linked Inhibitor of Apoptosis Proteins 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000013058 crude material Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- PAZHXBYGAZXOJW-KKXDTOCCSA-N CN[C@@H](C)C(=O)N[C@H](C(=O)N1[C@@H](Cc2ccccc12)C(O)=O)c1ccccc1 Chemical compound CN[C@@H](C)C(=O)N[C@H](C(=O)N1[C@@H](Cc2ccccc12)C(O)=O)c1ccccc1 PAZHXBYGAZXOJW-KKXDTOCCSA-N 0.000 description 8
- 241000713321 Intracisternal A-particles Species 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002671 adjuvant Substances 0.000 description 7
- 230000006907 apoptotic process Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 108090000765 processed proteins & peptides Proteins 0.000 description 7
- 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 102100033189 Diablo IAP-binding mitochondrial protein Human genes 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 230000001640 apoptogenic effect Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- KDOUBUZYGVSSLM-UHFFFAOYSA-N (5-fluoro-2-methylphenyl)methanamine Chemical compound CC1=CC=C(F)C=C1CN KDOUBUZYGVSSLM-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229960002685 biotin Drugs 0.000 description 4
- 239000011616 biotin Substances 0.000 description 4
- 235000015165 citric acid Nutrition 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000007821 HATU Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 125000006242 amine protecting group Chemical group 0.000 description 3
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- KISPUTPAKVZNBI-JTQLQIEISA-N ethyl (2s)-2,3-dihydro-1h-indole-2-carboxylate Chemical compound C1=CC=C2N[C@H](C(=O)OCC)CC2=C1 KISPUTPAKVZNBI-JTQLQIEISA-N 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- CHJNXKRZJYHZRQ-GJZGRUSLSA-N (2s)-1-[(2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]-2,3-dihydroindole-2-carboxylic acid Chemical compound C1=CC=C2N(C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)[C@H](C(O)=O)CC2=C1 CHJNXKRZJYHZRQ-GJZGRUSLSA-N 0.000 description 2
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000011272 standard treatment Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- ABZLKHKQJHEPAX-UHFFFAOYSA-N tetramethylrhodamine Chemical compound C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C([O-])=O ABZLKHKQJHEPAX-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 125000002114 valyl group Chemical group 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Epidemiology (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261712317P | 2012-10-11 | 2012-10-11 | |
| PCT/EP2013/070407 WO2014056755A1 (en) | 2012-10-11 | 2013-10-01 | Indolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2015004465A true MX2015004465A (es) | 2015-07-14 |
Family
ID=49293651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2015004465A MX2015004465A (es) | 2012-10-11 | 2013-10-01 | Indolinas. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9403768B2 (enExample) |
| EP (1) | EP2906535B1 (enExample) |
| JP (1) | JP6333825B2 (enExample) |
| KR (1) | KR20150065718A (enExample) |
| CN (1) | CN104736519B (enExample) |
| CA (1) | CA2884708A1 (enExample) |
| HK (1) | HK1211025A1 (enExample) |
| MX (1) | MX2015004465A (enExample) |
| RU (1) | RU2015113959A (enExample) |
| WO (1) | WO2014056755A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10383538B2 (en) | 2014-09-29 | 2019-08-20 | New York Institute Of Technology | Catheter for use in recording his electrogram alternans and application to various conditions |
| WO2016079527A1 (en) | 2014-11-19 | 2016-05-26 | Tetralogic Birinapant Uk Ltd | Combination therapy |
| WO2016097773A1 (en) | 2014-12-19 | 2016-06-23 | Children's Cancer Institute | Therapeutic iap antagonists for treating proliferative disorders |
| CN109152843A (zh) | 2016-05-20 | 2019-01-04 | 豪夫迈·罗氏有限公司 | Protac抗体缀合物及其使用方法 |
| US12636370B2 (en) | 2019-08-08 | 2026-05-26 | Institute For Cancer Research | Combination therapy for treatment of cancer |
| WO2023056069A1 (en) | 2021-09-30 | 2023-04-06 | Angiex, Inc. | Degrader-antibody conjugates and methods of using same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2733995B1 (fr) | 1995-05-09 | 1997-07-25 | Inst Nat Sante Rech Med | Inhibiteurs de l'inactivation de neuropeptides endogenes notamment la cholecystokinine, leurs procedes de preparation leur utilisation comme medicaments et procede de criblage de medicaments |
| CN1933847A (zh) * | 2004-01-16 | 2007-03-21 | 密歇根大学董事会 | Smac肽模拟物及其应用 |
| AP2007003894A0 (en) * | 2004-07-12 | 2007-02-28 | Bin Chao | Tetrapeptide analogs |
| BRPI0513310A (pt) * | 2004-07-12 | 2008-05-06 | Idun Pharmaceuticals Inc | análogos de tetrapeptìdeo |
| US8835393B2 (en) * | 2008-08-02 | 2014-09-16 | Genentech, Inc. | Inhibitors of IAP |
-
2013
- 2013-10-01 US US14/432,990 patent/US9403768B2/en not_active Expired - Fee Related
- 2013-10-01 JP JP2015536065A patent/JP6333825B2/ja not_active Expired - Fee Related
- 2013-10-01 CA CA2884708A patent/CA2884708A1/en not_active Abandoned
- 2013-10-01 EP EP13771145.3A patent/EP2906535B1/en not_active Not-in-force
- 2013-10-01 MX MX2015004465A patent/MX2015004465A/es unknown
- 2013-10-01 KR KR1020157009107A patent/KR20150065718A/ko not_active Withdrawn
- 2013-10-01 RU RU2015113959A patent/RU2015113959A/ru not_active Application Discontinuation
- 2013-10-01 WO PCT/EP2013/070407 patent/WO2014056755A1/en not_active Ceased
- 2013-10-01 HK HK15111756.4A patent/HK1211025A1/xx unknown
- 2013-10-01 CN CN201380052826.6A patent/CN104736519B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| RU2015113959A (ru) | 2016-12-10 |
| EP2906535B1 (en) | 2018-08-08 |
| HK1211025A1 (zh) | 2016-05-13 |
| US9403768B2 (en) | 2016-08-02 |
| JP2015534567A (ja) | 2015-12-03 |
| WO2014056755A1 (en) | 2014-04-17 |
| CA2884708A1 (en) | 2014-04-17 |
| US20150246882A1 (en) | 2015-09-03 |
| KR20150065718A (ko) | 2015-06-15 |
| JP6333825B2 (ja) | 2018-05-30 |
| CN104736519B (zh) | 2018-12-04 |
| CN104736519A (zh) | 2015-06-24 |
| EP2906535A1 (en) | 2015-08-19 |
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