HRP20140821T1 - Priprema kristalnih hemihidratnih oblika dihidropirazolopirimidinona - Google Patents
Priprema kristalnih hemihidratnih oblika dihidropirazolopirimidinona Download PDFInfo
- Publication number
- HRP20140821T1 HRP20140821T1 HRP20140821AT HRP20140821T HRP20140821T1 HR P20140821 T1 HRP20140821 T1 HR P20140821T1 HR P20140821A T HRP20140821A T HR P20140821AT HR P20140821 T HRP20140821 T HR P20140821T HR P20140821 T1 HRP20140821 T1 HR P20140821T1
- Authority
- HR
- Croatia
- Prior art keywords
- cancer
- crystalline
- crystalline hemihydrate
- hemihydrate according
- indicated
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 201000011510 cancer Diseases 0.000 claims 7
- BKWJAKQVGHWELA-UHFFFAOYSA-N 1-[6-(2-hydroxypropan-2-yl)-2-pyridinyl]-6-[4-(4-methyl-1-piperazinyl)anilino]-2-prop-2-enyl-3-pyrazolo[3,4-d]pyrimidinone Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=C)N(C=3N=C(C=CC=3)C(C)(C)O)C2=N1 BKWJAKQVGHWELA-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- 238000005384 cross polarization magic-angle spinning Methods 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 208000000649 small cell carcinoma Diseases 0.000 claims 2
- 238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 claims 2
- 206010000830 Acute leukaemia Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010004593 Bile duct cancer Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000006332 Choriocarcinoma Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
- 208000032271 Malignant tumor of penis Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010034259 Pelvic kidney Diseases 0.000 claims 1
- 208000002471 Penile Neoplasms Diseases 0.000 claims 1
- 206010034299 Penile cancer Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000023915 Ureteral Neoplasms Diseases 0.000 claims 1
- 206010046392 Ureteric cancer Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000026900 bile duct neoplasm Diseases 0.000 claims 1
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 230000001605 fetal effect Effects 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 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
-
- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Claims (15)
1. Kristalni 2-alil-1-[6-(1-hidroksi-1-metiletil)piridin-2-il]-6-{[4-(4-metilpiperazin-1-il)fenil]amino}-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on hemihidrat.
2. Kristalni 2-alil-1-[6-(1-hidroksi-1-metiletil)piridin-2-il]-6-{[4-(4-metilpiperazin-1-il)fenil]amino}-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on hemihidrat prema zahtjevu 1 koji je naznačen obrascem rendgenske difrakcije praška, dobivenim uporabom zračenjem bakrom Kα, koji odgovara d-razmacima od 13.81, 11.16 i 3.34 angstrema.
3. Kristalni hemihidrat prema zahtjevu 2 koji je dalje naznačen d-razmacima od 6.92, 6.74 i 6.53 angstrema.
4. Kristalni hemihidrat prema zahtjevu 3 koji je dalje naznačen d-razmacima od 18.17 i 4.30 angstrema.
5. Kristalni hemihidrat prema zahtjevu 2 koji je naznačen ugljik-13 CPMAS spektrom nuklearne magnetske rezonance krutog stanja sa signalima na 28.6, 55.8 i 132.3 p.p.m.
6. Kristalni hemihidrat prema zahtjevu 5 koji je dalje naznačen signalima na 123.2, 118.2 i 72.3 p.p.m.
7. Kristalni 2-alil-1-[6-(1-hidroksi-1-metiletil)piridin-2-il]-6-{[4-(4-metilpiperazin-1-il)fenil]amino}-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on hemihidrat prema zahtjevu 1 koji je naznačen obrascem rendgenske difrakcije praška, dobivenim uporabom zračenjem bakrom Kα, koji odgovara d-razmacima od 10.66, 5.30 i 4.18 angstrema.
8. Kristalni hemihidrat prema zahtjevu 7 koji je dalje naznačen d-razmacima od 9.11, 8.80 i 3.54 angstrema.
9. Kristalni hemihidrat prema zahtjevu 8 koji je dalje naznačen d-razmacima od 18.22, 3.09 i 3.02 angstrema.
10. Kristalni hemihidrat prema zahtjevu 7 koji je naznačen ugljik-13 CPMAS spektrom nuklearne magnetske rezonance krutog stanja sa signalima na 116.6, 52.4, 55.0 i 31.7 p.p.m.
11. Kristalni hemihidrat prema zahtjevu 10 koji je dalje naznačen signalima na 145.0, 154.8, 160.1 i 169.4 p.p.m.
12. Farmaceutska smjesa koja sadrži kristalni hemihidrat prema bilo kojem prethodnom zahtjevu i farmaceutski prihvatljiv nosač.
13. Kristalni hemihidrat prema bilo kojem od zahtjeva 1 do 11 za uporabu u liječenju raka.
14. Kristalni hemihidrat za uporabu prema zahtjevu 13 gdje se radi o raku izabranom iz skupine koja obuhvaća rak mozga, cervikocerebralni rak, rak jednjaka, rak štitnjače, rak malih stanica, rak ne-malih stanica, rak dojke, rak pluća, rak želuca, rak žučnog mjehura/žučovoda, rak jetre, rak gušterače, rak kolona, rak rektuma, rak jajnika, koriokarcinom, rak tijela maternice, uterocervikalni rak, zdjelični rak bubrega/mokraćovoda, rak mjehura, rak prostate, rak penisa, rak testisa, rak fetusa, Wilmsov rak, rak kože, maligni melanom, neuroblastom, osteosarkom, Ewingov tumor, sarkom mekog tkiva, akutna leukemija, kronična limfatička leukemija, kronična mijeloična leukemija i Hodgkinov limfom.
15. Kristalni hemihidrat prema bilo kojem od zahtjeva 1 do 11 za uporabu u liječenju.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24242809P | 2009-09-15 | 2009-09-15 | |
| US32304510P | 2010-04-12 | 2010-04-12 | |
| PCT/US2010/047622 WO2011034743A1 (en) | 2009-09-15 | 2010-09-02 | Preparation of crystalline forms of dihydropyrazolopyrimidinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20140821T1 true HRP20140821T1 (hr) | 2014-10-10 |
Family
ID=43758964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20140821AT HRP20140821T1 (hr) | 2009-09-15 | 2014-09-01 | Priprema kristalnih hemihidratnih oblika dihidropirazolopirimidinona |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8703779B2 (hr) |
| EP (1) | EP2477628B1 (hr) |
| DK (1) | DK2477628T3 (hr) |
| ES (1) | ES2524161T3 (hr) |
| HR (1) | HRP20140821T1 (hr) |
| PL (1) | PL2477628T3 (hr) |
| PT (1) | PT2477628E (hr) |
| SI (1) | SI2477628T1 (hr) |
| WO (1) | WO2011034743A1 (hr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2755482B1 (en) | 2011-09-15 | 2016-06-01 | Merck Sharp & Dohme Corp. | Combination of mk-1775 and mk-8776 for treating cancer |
| ES2651347T3 (es) * | 2012-11-28 | 2018-01-25 | Merck Sharp & Dohme Corp. | Composiciones y métodos para el tratamiento del cáncer |
| CN110198943B (zh) | 2017-01-23 | 2021-04-16 | 石家庄智康弘仁新药开发有限公司 | 作为Wee1抑制剂的1,2-二氢-3H-吡唑[3,4-d]嘧啶-3-酮衍生物 |
| WO2019037678A1 (zh) * | 2017-08-24 | 2019-02-28 | 上海迪诺医药科技有限公司 | 吡唑并[3,4-d]嘧啶-3-酮衍生物、其药物组合物及应用 |
| CA3078945A1 (en) | 2017-10-09 | 2019-04-18 | Nuvation Bo Inc. | Heterocyclic compounds and uses thereof |
| US11299493B2 (en) | 2017-10-09 | 2022-04-12 | Nuvation Bio Inc. | Heterocyclic compounds and uses thereof |
| CA3080842A1 (en) | 2017-11-01 | 2019-05-09 | Shijiazhuang Sagacity New Drug Development Co., Ltd. | Macrocyclic compound serving as weel inhibitor and applications thereof |
| WO2020083404A1 (zh) | 2018-10-26 | 2020-04-30 | 南京明德新药研发有限公司 | 作为Wee1抑制剂的嘧啶并吡唑酮类衍生物及其应用 |
| BR112021019703A2 (pt) | 2019-04-09 | 2021-12-14 | Nuvation Bio Inc | Compostos heterocíclicos e usos dos mesmos |
| JP2022530812A (ja) | 2019-04-30 | 2022-07-01 | シージャーヂュアン・サガシティー・ニュー・ドラッグ・デヴェロップメント・カンパニー・リミテッド | Ｗｅｅ１阻害剤化合物の結晶形及びその応用 |
| KR20220088896A (ko) | 2019-10-25 | 2022-06-28 | 아스트라제네카 아베 | 암을 치료하는 방법 |
| MX2022007625A (es) * | 2019-12-20 | 2022-08-16 | Recurium Ip Holdings Llc | Combinaciones. |
| US20230042653A1 (en) * | 2019-12-20 | 2023-02-09 | Recurium Ip Holdings, Llc | Combinations |
| WO2021254389A1 (zh) | 2020-06-17 | 2021-12-23 | 微境生物医药科技(上海)有限公司 | 作为Wee-1抑制剂的吡唑并[3，4-d]嘧啶-3-酮衍生物 |
| AU2022265032A1 (en) | 2021-04-30 | 2023-11-16 | Wigen Biomedicine Technology (shanghai) Co., Ltd. | Fused ring compound as wee-1 inhibitor, and preparation method therefor and use thereof |
| CN113735863A (zh) * | 2021-09-29 | 2021-12-03 | 武汉九州钰民医药科技有限公司 | Wee1抑制剂adavosertib的制备工艺 |
| CN113880844B (zh) * | 2021-09-29 | 2023-02-14 | 武汉九州钰民医药科技有限公司 | Wee1蛋白激酶抑制剂adavosertib的化学合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003224341A1 (en) | 2002-04-26 | 2003-11-10 | Warner-Lambert Company Llc | Inhibitors of checkpoint kinases (wee1 and chk1) |
| PE20080695A1 (es) | 2006-04-27 | 2008-06-28 | Banyu Pharma Co Ltd | Derivados de dihidropirazolopirimidinona como inhibidores de quinasa weel |
| EP2155752B1 (en) * | 2007-04-25 | 2018-09-19 | Merck Sharp & Dohme Corp. | Polymorph of dihydropyrazolopyrimidinone derivative as weel kinase.inhibitor |
-
2010
- 2010-09-02 SI SI201030764T patent/SI2477628T1/sl unknown
- 2010-09-02 US US13/496,014 patent/US8703779B2/en active Active
- 2010-09-02 WO PCT/US2010/047622 patent/WO2011034743A1/en active Application Filing
- 2010-09-02 PL PL10817669T patent/PL2477628T3/pl unknown
- 2010-09-02 DK DK10817669.4T patent/DK2477628T3/en active
- 2010-09-02 PT PT108176694T patent/PT2477628E/pt unknown
- 2010-09-02 ES ES10817669.4T patent/ES2524161T3/es active Active
- 2010-09-02 EP EP10817669.4A patent/EP2477628B1/en active Active
-
2014
- 2014-03-06 US US14/199,653 patent/US9388186B2/en active Active
- 2014-09-01 HR HRP20140821AT patent/HRP20140821T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20120172370A1 (en) | 2012-07-05 |
| EP2477628B1 (en) | 2014-08-20 |
| US8703779B2 (en) | 2014-04-22 |
| US20140187562A1 (en) | 2014-07-03 |
| PL2477628T3 (pl) | 2015-02-27 |
| SI2477628T1 (sl) | 2014-11-28 |
| EP2477628A1 (en) | 2012-07-25 |
| DK2477628T3 (en) | 2014-11-24 |
| WO2011034743A1 (en) | 2011-03-24 |
| US9388186B2 (en) | 2016-07-12 |
| PT2477628E (pt) | 2014-11-25 |
| EP2477628A4 (en) | 2013-04-17 |
| ES2524161T3 (es) | 2014-12-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20140821T1 (hr) | Priprema kristalnih hemihidratnih oblika dihidropirazolopirimidinona | |
| HRP20191944T1 (hr) | Soli i polimorfi od 8-fluoro-2-{4-[(metilamino)metil]fenil}-1,3,4,5-tetrahidro-6h-azepino[5,4,3-cd]indol-6-ona | |
| DOP2011000367A (es) | DERIVADOS DE SULFONAMIDA SUSTITUIDA CON 1H-PIRROLO[2,3,b]PIRIDIN-5-ILOXI COMO AGENTES INDUCTORES DE APOPTOSIS PARA EL TRATAMIENTO DE CANCER Y ENFERMEDADES INMUNES Y AUTOINMUNES | |
| Singh et al. | Iron doped β-Tricalcium phosphate: Synthesis, characterization, hyperthermia effect, biocompatibility and mechanical evaluation | |
| AR074575A1 (es) | Compuesto de benzoimidazol-pirimidin-aminopiridina, forma cristalina iii relacionada, formulacion farmaceutica que lo comprende y su uso para preparar un medicamento util para tratar un cancer | |
| RU2018102078A (ru) | Комбинированная терапия противоопухолевым алкалоидом | |
| MX2012007429A (es) | Compuestos y metodos para la modulacion de quinasa e indicaciones de la misma. | |
| NZ599090A (en) | Benzoxepin pi3k inhibitor compounds and methods of use | |
| PL2483278T3 (pl) | Związki benzoksazepinowe stanowiące inhibitor pi3k i ich zastosowanie w leczeniu nowotworu | |
| GEP201706678B (en) | Method of treating cancer and bone cancer | |
| JP2016516702A5 (hr) | ||
| RU2013128934A (ru) | Наночастицы, несущие химиотерапевтическое противораковое лекарственное средство | |
| Muthurajan et al. | Evaluation of a quercetin–gadolinium complex as an efficient positive contrast enhancer for magnetic resonance imaging | |
| Patel et al. | Three new tetranuclear phenoxy-bridged metal (II) complexes: Synthesis, structural variation, cryomagnetic properties, DFT study and antiprolifirative properties | |
| RU2014101626A (ru) | Полиморфы 2-амид 1-({4-метил-5-[2-(2, 2, 2-трифтор-1, 1-диметил-этил)-пиридин-4-ил]тиазол-2-ил}амида) (s)-пирролидин-1, 2-дикарбоновой кислоты | |
| JP2007519609A5 (hr) | ||
| JP2011516426A5 (hr) | ||
| EA201101604A1 (ru) | [1,2,4]триазоло[4,3-b]пиридазины в качестве лигандов андрогенового рецептора | |
| NZ598652A (en) | Cancer cell apoptosis | |
| JP2016504325A5 (hr) | ||
| Hong et al. | A triphenylphosphine coordinated cinnamaldehyde-derived copper (I) Fenton-like agent with mitochondrial aggregation damage for chemodynamic therapy | |
| RU2019123279A (ru) | Этан-сульфонатная соль производного хинолина | |
| Caballero et al. | New copper (II), nickel (II) and zinc (II) complexes with 1, 2, 4-triazolo [1, 5-a] pyrimidines and the chelating ligand 1, 3-propanediamine: An unexpected coordination behavior for the 7-amine-derivative | |
| WO2012009663A3 (en) | New compounds for treating cancer and other diseases | |
| Hong et al. | A mixed-valence biotinylated Cu (I/II) complex for tumor-targeted chemodynamic therapy accompanied by GSH depletion |