CA2948765A1 - Intermediate (4-bromo-2-fluorophenyl)-1h-imidazoyl derivatives for use in a process to synthesize benzoxazepin compounds - Google Patents
Intermediate (4-bromo-2-fluorophenyl)-1h-imidazoyl derivatives for use in a process to synthesize benzoxazepin compounds Download PDFInfo
- Publication number
- CA2948765A1 CA2948765A1 CA2948765A CA2948765A CA2948765A1 CA 2948765 A1 CA2948765 A1 CA 2948765A1 CA 2948765 A CA2948765 A CA 2948765A CA 2948765 A CA2948765 A CA 2948765A CA 2948765 A1 CA2948765 A1 CA 2948765A1
- Authority
- CA
- Canada
- Prior art keywords
- bromo
- acid
- ethyl
- solution
- mixture
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title abstract description 30
- 230000008569 process Effects 0.000 title abstract description 7
- -1 (4-bromo-2-fluorophenyl)-1h-imidazoyl Chemical class 0.000 title description 16
- ZCXLTWVZYXBHJS-UHFFFAOYSA-N 1,2-benzoxazepine Chemical class O1N=CC=CC2=CC=CC=C12 ZCXLTWVZYXBHJS-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 39
- BEUQXVWXFDOSAQ-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propanamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(N=C2)C(C)(C)C(N)=O)C3=N1 BEUQXVWXFDOSAQ-UHFFFAOYSA-N 0.000 abstract description 19
- 239000000543 intermediate Substances 0.000 abstract description 18
- 229950001269 taselisib Drugs 0.000 abstract description 17
- 238000002360 preparation method Methods 0.000 abstract description 7
- 239000012828 PI3K inhibitor Substances 0.000 abstract description 3
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 57
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- 238000006243 chemical reaction Methods 0.000 description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 34
- 239000007787 solid Substances 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 150000003839 salts Chemical class 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- 239000003153 chemical reaction reagent Substances 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 11
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- 238000007363 ring formation reaction Methods 0.000 description 10
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- 229910052757 nitrogen Inorganic materials 0.000 description 9
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- GJSNAEGRKQLHPW-UHFFFAOYSA-N 4-bromo-2-fluorobenzenecarboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=C(Br)C=C1F GJSNAEGRKQLHPW-UHFFFAOYSA-N 0.000 description 8
- HGXWRDPQFZKOLZ-UHFFFAOYSA-N 4-bromo-2-fluorobenzonitrile Chemical compound FC1=CC(Br)=CC=C1C#N HGXWRDPQFZKOLZ-UHFFFAOYSA-N 0.000 description 8
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- ILULYDJFTJKQAP-UHFFFAOYSA-N hydron;propan-2-ylhydrazine;chloride Chemical compound [Cl-].CC(C)N[NH3+] ILULYDJFTJKQAP-UHFFFAOYSA-N 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 7
- KMZGTOZTSHNTTM-UHFFFAOYSA-N n'-(propan-2-ylamino)ethanimidamide Chemical compound CC(C)NN=C(C)N KMZGTOZTSHNTTM-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- SCOJKGRNQDKFRP-UHFFFAOYSA-N 2-chloro-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CCl SCOJKGRNQDKFRP-UHFFFAOYSA-N 0.000 description 6
- HEFBSANBSMBSSP-UHFFFAOYSA-N 8-bromo-2,3-dihydro-1,4-benzoxazepin-5-amine Chemical compound NC1=NCCOC2=CC(Br)=CC=C12 HEFBSANBSMBSSP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- 239000004698 Polyethylene Substances 0.000 description 6
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- 239000003054 catalyst Substances 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
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- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 5
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 5
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
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- 239000003085 diluting agent Substances 0.000 description 5
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- PUAKAEDMCXRDPR-UHFFFAOYSA-N tert-butyl n-(propan-2-ylamino)carbamate Chemical compound CC(C)NNC(=O)OC(C)(C)C PUAKAEDMCXRDPR-UHFFFAOYSA-N 0.000 description 5
- XCMYPTLLFDFJAE-UHFFFAOYSA-N tert-butyl n-(propan-2-ylideneamino)carbamate Chemical compound CC(C)=NNC(=O)OC(C)(C)C XCMYPTLLFDFJAE-UHFFFAOYSA-N 0.000 description 5
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- IRSCQONAQHCRLC-UHFFFAOYSA-N 9-bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxylic acid Chemical compound C1COC2=CC(Br)=CC=C2C2=NC(C(=O)O)=CN21 IRSCQONAQHCRLC-UHFFFAOYSA-N 0.000 description 4
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- 229910052744 lithium Inorganic materials 0.000 description 1
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 229930182817 methionine Natural products 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
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- 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 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
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- 238000000643 oven drying Methods 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical group O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003906 phosphoinositides Chemical class 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
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- 239000012041 precatalyst Substances 0.000 description 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000009490 roller compaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
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- 238000007493 shaping process Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
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- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
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- YUSGHWDYBGUPKI-UHFFFAOYSA-N tert-butyl n-amino-n-propan-2-ylcarbamate Chemical compound CC(C)N(N)C(=O)OC(C)(C)C YUSGHWDYBGUPKI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- 150000003852 triazoles Chemical class 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-N tributyl(methyl)azanium;hydrochloride Chemical compound Cl.CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring systems
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA3005118A CA3005118A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA3005103A CA3005103A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA3005112A CA3005112A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361779619P | 2013-03-13 | 2013-03-13 | |
| US61/779,619 | 2013-03-13 | ||
| CA2897618A CA2897618A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2897618A Division CA2897618A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3005118A Division CA3005118A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA3005103A Division CA3005103A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA3005112A Division CA3005112A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
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|---|---|
| CA2948765A1 true CA2948765A1 (en) | 2014-09-18 |
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|---|---|---|---|
| CA2948765A Abandoned CA2948765A1 (en) | 2013-03-13 | 2014-03-12 | Intermediate (4-bromo-2-fluorophenyl)-1h-imidazoyl derivatives for use in a process to synthesize benzoxazepin compounds |
| CA3005112A Abandoned CA3005112A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA2948763A Expired - Fee Related CA2948763C (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA2897618A Abandoned CA2897618A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA3005118A Abandoned CA3005118A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA3005103A Abandoned CA3005103A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3005112A Abandoned CA3005112A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA2948763A Expired - Fee Related CA2948763C (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA2897618A Abandoned CA2897618A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA3005118A Abandoned CA3005118A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
| CA3005103A Abandoned CA3005103A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9303043B2 (enExample) |
| EP (3) | EP3845540A1 (enExample) |
| JP (6) | JP6363120B2 (enExample) |
| KR (3) | KR20180070715A (enExample) |
| CN (2) | CN105377856B (enExample) |
| AR (1) | AR095365A1 (enExample) |
| AU (3) | AU2014230812B2 (enExample) |
| BR (1) | BR112015020716A2 (enExample) |
| CA (6) | CA2948765A1 (enExample) |
| IL (1) | IL240793A0 (enExample) |
| MX (1) | MX2015011438A (enExample) |
| NZ (1) | NZ711192A (enExample) |
| RU (2) | RU2018109979A (enExample) |
| SG (2) | SG10201706760YA (enExample) |
| WO (1) | WO2014140073A1 (enExample) |
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| RU2018119749A (ru) * | 2013-12-16 | 2018-11-09 | Ф. Хоффманн-Ля Рош Аг | Полиморфы 2-(4-(2-(1-изопропил-3-метил-1h-1,2,4-триазол-5-ил)-5,6-дигидробензо[f]имидазо[1,2-d][1,4]оксазепин-9-ил)-1h-пиразол-1-ил)-2-метилпропанамида, способы их получения и фармацевтические применения |
| SI3317284T1 (sl) | 2015-07-02 | 2020-02-28 | F. Hoffmann-La Roche Ag | Spojine benzoksazepin oksazolidinona in načini uporabe |
| CN107995911B (zh) | 2015-07-02 | 2020-08-04 | 豪夫迈·罗氏有限公司 | 苯并氧氮杂*噁唑烷酮化合物及其使用方法 |
| CN105906635A (zh) * | 2016-06-08 | 2016-08-31 | 上海大学 | 全氟烷基苯并氮杂*并喹喔啉衍生物及其合成方法 |
| US10981877B2 (en) * | 2016-07-29 | 2021-04-20 | Japan Tobacco Inc. | Production method for pyrazole-amide compound |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201815787A (zh) | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| PL3555107T3 (pl) | 2016-12-15 | 2021-07-05 | F. Hoffmann-La Roche Ag | Sposób wytwarzania (S)-2-((2-((S)-4-(difluorometylo)-2-oksooksazolidyn-3-ylo)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oksazepin-9-ylo)amino)propanamidu |
| CN108752237A (zh) * | 2018-07-05 | 2018-11-06 | 四川青木制药有限公司 | 一种对氨基苯甲脒盐酸盐的新制备方法 |
| CA3124330A1 (en) | 2018-12-21 | 2020-06-25 | Daiichi Sankyo Company, Limited | Combination of antibody-drug conjugate and kinase inhibitor |
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| US6274327B1 (en) | 1992-04-13 | 2001-08-14 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
| GB9208135D0 (en) | 1992-04-13 | 1992-05-27 | Ludwig Inst Cancer Res | Polypeptides having kinase activity,their preparation and use |
| US5846824A (en) | 1994-02-07 | 1998-12-08 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
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2017
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