HRP20230563T1 - Nova sol bcl-2 inhibitora, srodni kristalni oblik, postupak za pripravu istih i farmaceutski pripravci koji ih sadrže - Google Patents
Nova sol bcl-2 inhibitora, srodni kristalni oblik, postupak za pripravu istih i farmaceutski pripravci koji ih sadrže Download PDFInfo
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- HRP20230563T1 HRP20230563T1 HRP20230563TT HRP20230563T HRP20230563T1 HR P20230563 T1 HRP20230563 T1 HR P20230563T1 HR P20230563T T HRP20230563T T HR P20230563TT HR P20230563 T HRP20230563 T HR P20230563T HR P20230563 T1 HRP20230563 T1 HR P20230563T1
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- Prior art keywords
- ppm
- compound
- hydrogen sulfate
- sulfate salt
- crystalline form
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- 238000000034 method Methods 0.000 title claims 6
- 239000012664 BCL-2-inhibitor Substances 0.000 title 1
- 229940123711 Bcl2 inhibitor Drugs 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 23
- 229940126062 Compound A Drugs 0.000 claims 19
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 235000011149 sulphuric acid Nutrition 0.000 claims 4
- VNNWQLOUMFCVJD-XIFFEERXSA-N 5-[5-chloro-2-[(3S)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(5-cyano-1,2-dimethylpyrrol-3-yl)-N-(4-hydroxyphenyl)-1,2-dimethylpyrrole-3-carboxamide Chemical compound Cc1c(cc(C#N)n1C)N(C(=O)c1cc(-c2cc(Cl)ccc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n(C)c1C)c1ccc(O)cc1 VNNWQLOUMFCVJD-XIFFEERXSA-N 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 3
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000028564 B-cell non-Hodgkin lymphoma 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
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia 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
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 238000001875 carbon-13 cross-polarisation magic angle spinning nuclear magnetic resonance spectrum Methods 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 208000003747 lymphoid leukemia Diseases 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (19)
1. Hidrogen sulfatna sol 5-(5-kloro-2-{[(3S)-3-(morfolin-4-ilmetil)-3,4-dihidroizokinolin-2(1H)-il]karbonil}fenil)-N- (5-cijano-1,2-dimetil-1H-pirol-3-il)-N-(4-hidroksifenil)-1,2-dimetil-1H-pirol-3-karboksamid (Spoj A, H2SO4).
2. Kristalni oblik I hidrogen sulfatne soli 5-(5-kloro-2-{[(3S)-3-(morfolin-4-ilmetil)-3,4-dihidroizokinolin-2(1H)-il]karbonil}fenil)-N-(5-cijano-1,2-dimetil-1H-pirol-3-il)-N-(4-hidroksifenil)-1,2-dimetil-1H-pirol-3-karboksamid (Spoj A, H2SO4) prema patentnom zahtjevu 1, pri čemu kristalni oblik ima difrakcijski dijagram rendgenskih zraka na prahu koji prikazuje sljedeće difrakcijske linije (Braggov kut 2 theta, izražen u stupnjevima ± 0.2°): 5,55; 6,62 i 7,39.
3. Kristalni oblik I hidrogen sulfatne soli 5-(5-kloro-2-{[(3S)-3-(morfolin-4-ilmetil)-3,4-dihidroizokinolin-2(1H)-il]karbonil} fenil)-N-(5-cijano-1,2-dimetil-1H-pirol-3-il)-N-(4-hidroksifenil)-1,2-dimetil-1H-pirol-3-karboksamid (Spoj A, H2SO4) prema patentnom zahtjevu 1, pri čemu kristalni oblik ima difrakcijski dijagram rendgenskih zraka na prahu koji prikazuje najmanje 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 ili sve sljedeće difrakcijske linije (Braggov kut 2 theta, izražen u stupnjevima ± 0.2°): 5,55; 5,62; 6,62; 7,39; 10,17; 11,49; 11,83; 16,01; 16,54; 17,04; 18,98; 19,18; 21,90; 22,28; 24,89.
4. Kristalni oblik I hidrogen sulfatne soli Spoja A prema patentnom zahtjevu 3, naznačen time što ima difrakcijski dijagram rendgenskih zraka na prahu koji ima sljedeće difrakcijske linije (Braggov kut 2 theta, izražen u stupnjevima ± 0.2°): 5,55; 5,62; 6,62; 7,39; 10,17; 11,49; 11,83; 16,01; 16,54; 17,04; 18,98; 19,18; 21,90; 22,28; 24,89.
5. Kristalni oblik I hidrogen sulfatne soli Spoja A prema patentnom zahtjevu 4, naznačen time što ima difrakcijski dijagram rendgenskih zraka na prahu izmjeren pomoću PANalytical X'Pert Pro MPD difraktometra s X'Celerator detektorom i izražen položajem linije (Braggov kut 2 theta, izražen u stupnjevima ± 0.2°) i interplanarne udaljenosti d (izražene u Å):
[image]
6. Kristalni oblik I hidrogen sulfatne soli Spoja A prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što ima 13C CP/MAS NMR spektar čvrstog stanja koji ima sljedeće maksimume (izraženo u ppm ± 0,2 ppm): 173,31 ppm, 155,32 ppm, 140,46 ppm, 139,19 ppm, 137,42 ppm, 134,68 ppm, 131,65 ppm, 131,14 ppm, 129,37 ppm, 126,32 ppm, 118,77 ppm, 117,36 ppm, 116,54 ppm, 113,61 ppm, 112,69 ppm, 110,74 ppm, 102,33 ppm , 101,45 ppm, 63,06 ppm, 57,19 ppm, 54,87 ppm, 52,06 ppm, 44,71 ppm, 43,94 ppm, 34,42 ppm, 32,89 ppm, 31,28 ppm, 30,66 ppm, 14,40 ppm , 13,34 ppm, 12,49 ppm i 10,50 ppm.
7. Farmaceutski pripravak koji kao aktivni sastojak sadrži hidrogen sulfatnu sol Spoja A prema patentnom zahtjevu 1 u kombinaciji s jednom ili više farmaceutski prihvatljivih pomoćnih tvari.
8. Farmaceutski pripravak koji kao aktivni sastojak sadrži kristalni oblik I hidrogen sulfatne soli spoja A prema bilo kojem od patentnih zahtjeva 2 do 6 u kombinaciji s jednom ili više farmaceutski prihvatljivih pomoćnih tvari.
9. Farmaceutski pripravak prema patentnom zahtjevu 7 ili 8 za upotrebu u liječenju raka, autoimunih bolesti i bolesti imunološkog sustava.
10. Farmaceutski pripravak za upotrebu u skladu s patentnim zahtjevom 9, pri čemu je rak odabran između raka mjehura, mozga, dojke i maternice, kroničnih limfoidnih leukemija, kolorektalnog raka, raka jednjaka i jetre, limfoblastičnih leukemija, akutne mijeloične leukemije, limfoma, na primjer ne-Hodgkinovog B-staničnog limfoma i difuznog velikog B-staničnog limfoma, melanoma, maligne hemopatije, na primjer mijelodisplastičnog sindroma, mijeloma, na primjer multiplog mijeloma, raka jajnika, raka pluća nemalih stanica, raka prostate, raka gušterače i raka pluća malih stanica.
11. Hidrogen sulfatna sol Spoja A prema patentnom zahtjevu 1, za upotrebu kao lijek.
12. Kristalni oblik I hidrogen sulfatne soli Spoja A prema bilo kojem od patentnih zahtjeva 2 do 6, za upotrebu kao lijek.
13. Postupak za pripravu kristalne forme I hidrogen sulfatne soli Spoja A prema bilo kojem od patentnih zahtjeva 2 do 6, pri čemu je hidrogen sulfatna sol Spoja A kristalizirana u polarnom mediju.
14. Postupak za pripravu kristalnog oblika I hidrogen sulfatne soli Spoja A prema patentnom zahtjevu 13, pri čemu se polarni medij sastoji od jednog ili više otapala odabranih između vode i alkohola.
15. Postupak za pripravu kristalnog oblika I hidrogen sulfatne soli Spoja A prema patentnom zahtjevu 14, pri čemu je alkohol etanol.
16. Postupak za pripravu kristalnog oblika I hidrogen sulfatne soli Spoja A prema patentnom zahtjevu 14, pri čemu je polarni medij smjesa etanola/vode.
17. Postupak za pripravu kristalnog oblika I hidrogen sulfatne soli Spoja A prema bilo kojem patentnom zahtjevu od 13 do 16, u kojem se postupku kristalizacija unosi pomoću vrlo male količine kristalnog oblika I hidrogen sulfatne soli Spoja A.
18. Bezvodni kristalni oblik hidrogen sulfatne soli 5-(5-kloro-2-{[(3S)-3-(morfolin-4-ilmetil)-3,4-dihidroizokinolin-2(1H)-il]karbonil} fenil)-N-(5-cijano-1,2-dimetil-1H-pirol-3-il)-N-(4-hidroksifenil)-1,2-dimetil 1H-pirol-3-karboksamid (Spoj A, H2SO4 ) prema patentnom zahtjevu 1, pri čemu kristalni oblik ima difrakcijski dijagram rendgenskih zraka na prahu koji prikazuje najmanje 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 ili sve od sljedećih difrakcijskih linija (Braggov kut 2 theta, izražen u stupnjevima ± 0,2°): 5,19; 5.64; 6.74; 7.14; 8.04; 8.33; 9.17; 9.40; 10.68; 11.03; 11.35; 12.18; 12.59; 13.64; 14.78; 15.09.
19. Bezvodni kristalni oblik hidrogen sulfatne soli spoja A prema patentnom zahtjevu 18, naznačen time što ima sljedeći difrakcijski dijagram rendgenskih zraka na prahu, mjeren pomoću PANalytical X'Pert Pro MPD difraktometra s X'Celerator detektorom i izražen položajem linije (Braggov kut 2 theta, izražen u stupnjevima ± 0,2°) i interplanarne udaljenosti d (izraženih u Å):
[image]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18306430 | 2018-10-31 | ||
| PCT/EP2019/079621 WO2020089281A1 (en) | 2018-10-31 | 2019-10-30 | Novel salt of a bcl-2 inhibitor, related crystalline form, method for preparing the same and pharmaceutical compositions containing the same |
| EP19800947.4A EP3873894B1 (en) | 2018-10-31 | 2019-10-30 | Novel salt of a bcl-2 inhibitor, related crystalline form, method for preparing the same and pharmaceutical compositions containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20230563T1 true HRP20230563T1 (hr) | 2023-08-18 |
Family
ID=64270773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20230563TT HRP20230563T1 (hr) | 2018-10-31 | 2019-10-30 | Nova sol bcl-2 inhibitora, srodni kristalni oblik, postupak za pripravu istih i farmaceutski pripravci koji ih sadrže |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US20210355108A1 (hr) |
| EP (1) | EP3873894B1 (hr) |
| JP (1) | JP2022506137A (hr) |
| KR (1) | KR20210092750A (hr) |
| CN (1) | CN112969693A (hr) |
| AR (1) | AR116921A1 (hr) |
| AU (1) | AU2019370926A1 (hr) |
| BR (1) | BR112021007194A2 (hr) |
| CA (1) | CA3117559C (hr) |
| CL (1) | CL2021000947A1 (hr) |
| CO (1) | CO2021005077A2 (hr) |
| CR (1) | CR20210211A (hr) |
| CY (1) | CY1126057T1 (hr) |
| DK (1) | DK3873894T3 (hr) |
| DO (1) | DOP2021000074A (hr) |
| EA (1) | EA202191143A1 (hr) |
| ES (1) | ES2943511T3 (hr) |
| FI (1) | FI3873894T3 (hr) |
| GE (1) | GEP20237494B (hr) |
| HR (1) | HRP20230563T1 (hr) |
| HU (1) | HUE062000T2 (hr) |
| IL (1) | IL282565A (hr) |
| JO (1) | JOP20210072A1 (hr) |
| LT (1) | LT3873894T (hr) |
| MA (1) | MA54063B1 (hr) |
| MX (1) | MX2021004934A (hr) |
| NI (1) | NI202100025A (hr) |
| PE (1) | PE20211503A1 (hr) |
| PH (1) | PH12021550790A1 (hr) |
| PL (1) | PL3873894T3 (hr) |
| PT (1) | PT3873894T (hr) |
| RS (1) | RS64236B1 (hr) |
| SG (1) | SG11202103594XA (hr) |
| SI (1) | SI3873894T1 (hr) |
| TW (1) | TWI791916B (hr) |
| WO (1) | WO2020089281A1 (hr) |
| ZA (1) | ZA202102783B (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL300145A (en) | 2020-07-31 | 2023-03-01 | Servier Lab | A combination of a BCL-2 inhibitor and a hypomethylating agent for the treatment of cancer, its uses and pharmaceutical preparations |
| WO2022090443A1 (en) | 2020-10-30 | 2022-05-05 | Les Laboratoires Servier | Administration and dose regimen for a combination of a bcl-2 inhibitor and a mcl1 inhibitor |
| CA3214107A1 (en) | 2021-03-24 | 2022-09-29 | Les Laboratoires Servier | New process for the synthesis of 5-{5-chloro-2-[(3s)-3- [(morpholin-4-yl)methyl]-3,4-dihydroisoquinoline-2(1h)- carbonyl]phenyl}-1,2-dimethyl-1h-pyrrole-3-carboxylic acid derivatives and its application for the production of pharmaceutical compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004057195A1 (de) * | 2004-11-26 | 2006-06-01 | Wilex Ag | Kristalline Modifikationen von N-Alpha-(2,4,6-Triisopropylphenylsulfonyl)-3-hydroxyamidino-(L)-phenylalanin-4-ethoxycarbonylpiperazid und/oder Salzen davon |
| KR100830002B1 (ko) * | 2005-01-06 | 2008-05-15 | 씨제이제일제당 (주) | 시부트라민의 무기산염 |
| TWI405756B (zh) * | 2005-12-21 | 2013-08-21 | Array Biopharma Inc | 新穎硫酸氫鹽 |
| CN101962387B (zh) * | 2010-09-13 | 2013-01-30 | 成都雅途生物技术有限公司 | 一种新结晶形态的氯吡格雷硫酸氢盐及其制备方法 |
| CN103664753B (zh) * | 2012-09-04 | 2017-04-26 | 上海迪赛诺化学制药有限公司 | 制备阿扎那韦硫酸氢盐a型结晶的方法 |
| FR3008975A1 (fr) * | 2013-07-23 | 2015-01-30 | Servier Lab | Nouveaux derives de pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2016165626A1 (en) * | 2015-04-15 | 2016-10-20 | Beigene, Ltd. | Maleate salts of a b-raf kinase inhibitor, crystalline forms, methods of preparation, and uses therefore |
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2019
- 2019-10-30 EA EA202191143A patent/EA202191143A1/ru unknown
- 2019-10-30 EP EP19800947.4A patent/EP3873894B1/en active Active
- 2019-10-30 US US17/286,936 patent/US20210355108A1/en active Pending
- 2019-10-30 CR CR20210211A patent/CR20210211A/es unknown
- 2019-10-30 PL PL19800947.4T patent/PL3873894T3/pl unknown
- 2019-10-30 RS RS20230347A patent/RS64236B1/sr unknown
- 2019-10-30 FI FIEP19800947.4T patent/FI3873894T3/fi active
- 2019-10-30 PE PE2021000597A patent/PE20211503A1/es unknown
- 2019-10-30 AU AU2019370926A patent/AU2019370926A1/en active Pending
- 2019-10-30 CA CA3117559A patent/CA3117559C/en active Active
- 2019-10-30 BR BR112021007194-6A patent/BR112021007194A2/pt unknown
- 2019-10-30 TW TW108139360A patent/TWI791916B/zh active
- 2019-10-30 SI SI201930557T patent/SI3873894T1/sl unknown
- 2019-10-30 HU HUE19800947A patent/HUE062000T2/hu unknown
- 2019-10-30 AR ARP190103143A patent/AR116921A1/es unknown
- 2019-10-30 KR KR1020217015833A patent/KR20210092750A/ko unknown
- 2019-10-30 WO PCT/EP2019/079621 patent/WO2020089281A1/en active Application Filing
- 2019-10-30 ES ES19800947T patent/ES2943511T3/es active Active
- 2019-10-30 JO JOP/2021/0072A patent/JOP20210072A1/ar unknown
- 2019-10-30 GE GEAP201915620A patent/GEP20237494B/en unknown
- 2019-10-30 PT PT198009474T patent/PT3873894T/pt unknown
- 2019-10-30 LT LTEPPCT/EP2019/079621T patent/LT3873894T/lt unknown
- 2019-10-30 CN CN201980071289.7A patent/CN112969693A/zh active Pending
- 2019-10-30 SG SG11202103594XA patent/SG11202103594XA/en unknown
- 2019-10-30 MX MX2021004934A patent/MX2021004934A/es unknown
- 2019-10-30 MA MA54063A patent/MA54063B1/fr unknown
- 2019-10-30 HR HRP20230563TT patent/HRP20230563T1/hr unknown
- 2019-10-30 DK DK19800947.4T patent/DK3873894T3/da active
- 2019-10-30 JP JP2021523309A patent/JP2022506137A/ja active Pending
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2021
- 2021-04-09 PH PH12021550790A patent/PH12021550790A1/en unknown
- 2021-04-09 NI NI202100025A patent/NI202100025A/es unknown
- 2021-04-16 CL CL2021000947A patent/CL2021000947A1/es unknown
- 2021-04-21 DO DO2021000074A patent/DOP2021000074A/es unknown
- 2021-04-21 CO CONC2021/0005077A patent/CO2021005077A2/es unknown
- 2021-04-22 IL IL282565A patent/IL282565A/en unknown
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2023
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