CZ2016816A3 - Krystalické formy 2-[1-ethylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrilu s kyselinou fosforečnou a způsob jejich přípravy - Google Patents
Krystalické formy 2-[1-ethylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrilu s kyselinou fosforečnou a způsob jejich přípravy Download PDFInfo
- Publication number
- CZ2016816A3 CZ2016816A3 CZ2016-816A CZ2016816A CZ2016816A3 CZ 2016816 A3 CZ2016816 A3 CZ 2016816A3 CZ 2016816 A CZ2016816 A CZ 2016816A CZ 2016816 A3 CZ2016816 A3 CZ 2016816A3
- Authority
- CZ
- Czechia
- Prior art keywords
- baricitinib
- phosphate
- theta
- water
- ray powder
- Prior art date
Links
- XUZMWHLSFXCVMG-UHFFFAOYSA-N baricitinib Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 XUZMWHLSFXCVMG-UHFFFAOYSA-N 0.000 title claims abstract description 125
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 18
- 229950000971 baricitinib Drugs 0.000 claims abstract description 65
- 239000000203 mixture Substances 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
- 239000000843 powder Substances 0.000 claims description 39
- 230000005855 radiation Effects 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- FBPOWTFFUBBKBB-UHFFFAOYSA-N 2-[1-ethylsulfonyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile;phosphoric acid Chemical compound OP(O)(O)=O.C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 FBPOWTFFUBBKBB-UHFFFAOYSA-N 0.000 claims description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
- 239000011877 solvent mixture Substances 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- -1 baricitinib phosphoric acid salt Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 10
- FGDQGIKMWOAFIK-UHFFFAOYSA-N acetonitrile;phosphoric acid Chemical compound CC#N.OP(O)(O)=O FGDQGIKMWOAFIK-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 abstract 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 abstract 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 230000001747 exhibiting effect Effects 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910016523 CuKa Inorganic materials 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
- 206010013774 Dry eye Diseases 0.000 description 1
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 description 1
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 208000033679 diabetic kidney disease Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UMYZHWLYICNGRQ-UHFFFAOYSA-N ethanol;heptane Chemical compound CCO.CCCCCCC UMYZHWLYICNGRQ-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2016-816A CZ2016816A3 (cs) | 2016-12-21 | 2016-12-21 | Krystalické formy 2-[1-ethylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrilu s kyselinou fosforečnou a způsob jejich přípravy |
| PCT/CZ2017/000079 WO2018113801A1 (fr) | 2016-12-21 | 2017-12-21 | Formes cristallines de 2-[1-éthylsulfonyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azétidin-3-yl]acétonitrile avec de l'acide phosphorique et leur procédé de préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2016-816A CZ2016816A3 (cs) | 2016-12-21 | 2016-12-21 | Krystalické formy 2-[1-ethylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrilu s kyselinou fosforečnou a způsob jejich přípravy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ2016816A3 true CZ2016816A3 (cs) | 2018-07-04 |
Family
ID=61167842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ2016-816A CZ2016816A3 (cs) | 2016-12-21 | 2016-12-21 | Krystalické formy 2-[1-ethylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrilu s kyselinou fosforečnou a způsob jejich přípravy |
Country Status (2)
| Country | Link |
|---|---|
| CZ (1) | CZ2016816A3 (fr) |
| WO (1) | WO2018113801A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3725305A1 (fr) | 2019-04-17 | 2020-10-21 | Zentiva K.S. | Composition pharmaceutique contenant du bromhydrate de baricitinib |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111278828B (zh) * | 2018-01-09 | 2021-08-31 | 广东东阳光药业有限公司 | 巴瑞替尼磷酸盐的新晶型及其制备方法 |
| WO2020163431A1 (fr) | 2019-02-05 | 2020-08-13 | Teva Pharmaceuticals International Gmbh | Formes solides cristallines de baricitinib |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2010010012A (es) | 2008-03-11 | 2010-10-20 | Incyte Corp | Derivados de azetidina y ciclobutano como inhibidores de jak. |
| CL2009001884A1 (es) | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
| WO2015145286A1 (fr) | 2014-03-28 | 2015-10-01 | Sun Pharmaceutical Industries Limited | Forme amorphe de baricitinib |
| WO2015166434A1 (fr) | 2014-05-01 | 2015-11-05 | Sun Pharmaceutical Industries Limited | Forme cristalline de baricitinib |
| WO2016125080A2 (fr) | 2015-02-02 | 2016-08-11 | Sun Pharmaceutical Industries Limited | Procédé de synthèse de baricitinib et d'un intermédiaire de celui-ci |
| CN105294699B (zh) | 2015-12-04 | 2019-06-11 | 上海勋和医药科技有限公司 | 巴瑞替尼的制备方法 |
| CN105693731A (zh) | 2016-01-26 | 2016-06-22 | 上海宣创生物科技有限公司 | 巴瑞克替尼a晶型及其制备方法 |
| CN107573349A (zh) * | 2016-02-01 | 2018-01-12 | 上海宣创生物科技有限公司 | 巴瑞克替尼磷酸盐h晶型及其制备方法 |
| CN105541891B (zh) | 2016-02-04 | 2017-11-28 | 东南大学 | 巴瑞替尼的中间体及其制备方法及由该中间体制备巴瑞替尼的方法 |
-
2016
- 2016-12-21 CZ CZ2016-816A patent/CZ2016816A3/cs unknown
-
2017
- 2017-12-21 WO PCT/CZ2017/000079 patent/WO2018113801A1/fr not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3725305A1 (fr) | 2019-04-17 | 2020-10-21 | Zentiva K.S. | Composition pharmaceutique contenant du bromhydrate de baricitinib |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2018113801A1 (fr) | 2018-06-28 |
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