CA2928286A1 - Forme solide de phosphate de ruxolitinib - Google Patents
Forme solide de phosphate de ruxolitinib Download PDFInfo
- Publication number
- CA2928286A1 CA2928286A1 CA2928286A CA2928286A CA2928286A1 CA 2928286 A1 CA2928286 A1 CA 2928286A1 CA 2928286 A CA2928286 A CA 2928286A CA 2928286 A CA2928286 A CA 2928286A CA 2928286 A1 CA2928286 A1 CA 2928286A1
- Authority
- CA
- Canada
- Prior art keywords
- ruxolitinib phosphate
- ruxolitinib
- apo
- phosphate
- polymorphic form
- 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
- JFMWPOCYMYGEDM-XFULWGLBSA-N ruxolitinib phosphate Chemical compound OP(O)(O)=O.C1([C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCCC1 JFMWPOCYMYGEDM-XFULWGLBSA-N 0.000 title claims abstract description 40
- 229960002539 ruxolitinib phosphate Drugs 0.000 title claims abstract description 37
- 239000007787 solid Substances 0.000 title abstract description 10
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 19
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 12
- 239000002144 L01XE18 - Ruxolitinib Substances 0.000 claims description 10
- 229960000215 ruxolitinib Drugs 0.000 claims description 10
- HFNKQEVNSGCOJV-OAHLLOKOSA-N ruxolitinib Chemical compound C1([C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCCC1 HFNKQEVNSGCOJV-OAHLLOKOSA-N 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 239000000203 mixture Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 201000010099 disease Diseases 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 102000015617 Janus Kinases Human genes 0.000 description 9
- 108010024121 Janus Kinases Proteins 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 150000003892 tartrate salts Chemical class 0.000 description 8
- 101000611023 Homo sapiens Tumor necrosis factor receptor superfamily member 6 Proteins 0.000 description 7
- 102100040403 Tumor necrosis factor receptor superfamily member 6 Human genes 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 238000002648 combination therapy Methods 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 208000017520 skin disease Diseases 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002062 proliferating effect Effects 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 206010028537 myelofibrosis Diseases 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical group C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000042838 JAK family Human genes 0.000 description 2
- 229940122245 Janus kinase inhibitor Drugs 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- -1 alkyl acetates Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- 229940124302 mTOR inhibitor Drugs 0.000 description 2
- 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 208000003476 primary myelofibrosis Diseases 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- STNAQNGWDXASLM-ZZXKWVIFSA-N (e)-3-cyclopentylprop-2-enal Chemical compound O=C\C=C\C1CCCC1 STNAQNGWDXASLM-ZZXKWVIFSA-N 0.000 description 1
- GNENVASJJIUNER-UHFFFAOYSA-N 2,4,6-tricyclohexyloxy-1,3,5,2,4,6-trioxatriborinane Chemical compound C1CCCCC1OB1OB(OC2CCCCC2)OB(OC2CCCCC2)O1 GNENVASJJIUNER-UHFFFAOYSA-N 0.000 description 1
- SCFUWKDVGXGFJC-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical class N1C2=NC=CC2=CN=C1C=1C=CNN=1 SCFUWKDVGXGFJC-UHFFFAOYSA-N 0.000 description 1
- SJXLTSDYZRWRQH-UHFFFAOYSA-N 3-pyrazol-1-ylpropanenitrile Chemical compound N#CCCN1C=CC=N1 SJXLTSDYZRWRQH-UHFFFAOYSA-N 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
- 206010013774 Dry eye Diseases 0.000 description 1
- 208000032027 Essential Thrombocythemia Diseases 0.000 description 1
- 208000014767 Myeloproliferative disease Diseases 0.000 description 1
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 206010041660 Splenomegaly Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000005966 aza-Michael addition reaction Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006362 organocatalysis Methods 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 208000037244 polycythemia vera Diseases 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003909 protein kinase inhibitor Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562153650P | 2015-04-28 | 2015-04-28 | |
| US62/153,650 | 2015-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2928286A1 true CA2928286A1 (fr) | 2016-10-28 |
Family
ID=57215559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2928286A Abandoned CA2928286A1 (fr) | 2015-04-28 | 2016-04-27 | Forme solide de phosphate de ruxolitinib |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2928286A1 (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023121574A1 (fr) * | 2021-12-23 | 2023-06-29 | Deva Holding Anonim Sirketi | Nouveau polymorphe d'hémifumarate de ruxolitinib et son procédé de préparation |
| US20230226064A1 (en) * | 2020-06-24 | 2023-07-20 | Novartis Ag | Oral liquid formulations of ruxolitinib |
| WO2023245053A1 (fr) * | 2022-06-14 | 2023-12-21 | Incyte Corporation | Formes solides d'un inhibiteur de jak et leur procédé de préparation |
| WO2024172778A1 (fr) * | 2023-02-16 | 2024-08-22 | Deva Holding | Nouveau polymorphe d'hémifumarate de ruxolitinib et procédé de préparation |
| US12071439B2 (en) | 2021-07-12 | 2024-08-27 | Incyte Corporation | Process and intermediates for preparing a JAK inhibitor |
| US12247034B1 (en) | 2024-04-19 | 2025-03-11 | Sun Pharmaceutical Industries, Inc. | Crystalline form of deuruxolitinib phosphate |
| US12428426B2 (en) | 2020-08-18 | 2025-09-30 | Incyte Corporation | Process and intermediates for preparing a JAK1 inhibitor |
| US12479851B2 (en) | 2020-08-18 | 2025-11-25 | Incyte Corporation | Process and intermediates for preparing a JAK inhibitor |
-
2016
- 2016-04-27 CA CA2928286A patent/CA2928286A1/fr not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20230226064A1 (en) * | 2020-06-24 | 2023-07-20 | Novartis Ag | Oral liquid formulations of ruxolitinib |
| US12428426B2 (en) | 2020-08-18 | 2025-09-30 | Incyte Corporation | Process and intermediates for preparing a JAK1 inhibitor |
| US12479851B2 (en) | 2020-08-18 | 2025-11-25 | Incyte Corporation | Process and intermediates for preparing a JAK inhibitor |
| US12071439B2 (en) | 2021-07-12 | 2024-08-27 | Incyte Corporation | Process and intermediates for preparing a JAK inhibitor |
| WO2023121574A1 (fr) * | 2021-12-23 | 2023-06-29 | Deva Holding Anonim Sirketi | Nouveau polymorphe d'hémifumarate de ruxolitinib et son procédé de préparation |
| WO2023245053A1 (fr) * | 2022-06-14 | 2023-12-21 | Incyte Corporation | Formes solides d'un inhibiteur de jak et leur procédé de préparation |
| WO2024172778A1 (fr) * | 2023-02-16 | 2024-08-22 | Deva Holding | Nouveau polymorphe d'hémifumarate de ruxolitinib et procédé de préparation |
| US12247034B1 (en) | 2024-04-19 | 2025-03-11 | Sun Pharmaceutical Industries, Inc. | Crystalline form of deuruxolitinib phosphate |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |
Effective date: 20190429 |