CN109563059A - 奥扎莫德的晶型及其制备方法 - Google Patents
奥扎莫德的晶型及其制备方法 Download PDFInfo
- Publication number
- CN109563059A CN109563059A CN201780045272.5A CN201780045272A CN109563059A CN 109563059 A CN109563059 A CN 109563059A CN 201780045272 A CN201780045272 A CN 201780045272A CN 109563059 A CN109563059 A CN 109563059A
- Authority
- CN
- China
- Prior art keywords
- crystal form
- zhamode
- preparation
- ray powder
- powder diffraction
- 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.)
- Pending
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 189
- 238000002360 preparation method Methods 0.000 title claims abstract description 36
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 11
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 64
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 42
- 239000007787 solid Substances 0.000 claims description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000012046 mixed solvent Substances 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 9
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 7
- 229940011051 isopropyl acetate Drugs 0.000 claims description 7
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 150000004292 cyclic ethers Chemical class 0.000 claims description 4
- 239000004210 ether based solvent Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000011287 therapeutic dose Methods 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 4
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 238000009509 drug development Methods 0.000 abstract description 2
- 238000009826 distribution Methods 0.000 description 20
- 239000002245 particle Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000008859 change Effects 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- 229910017488 Cu K Inorganic materials 0.000 description 3
- 229910017541 Cu-K Inorganic materials 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 210000000278 spinal cord Anatomy 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 102000006386 Myelin Proteins Human genes 0.000 description 2
- 108010083674 Myelin Proteins Proteins 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000857 drug effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- KKGQTZUTZRNORY-UHFFFAOYSA-N fingolimod Chemical compound CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 KKGQTZUTZRNORY-UHFFFAOYSA-N 0.000 description 2
- 229960000556 fingolimod Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 210000005012 myelin Anatomy 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical group CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- XRVDGNKRPOAQTN-FQEVSTJZSA-N 5-[3-[(1s)-1-(2-hydroxyethylamino)-2,3-dihydro-1h-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-propan-2-yloxybenzonitrile Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3CC[C@@H](C=3C=CC=2)NCCO)=NO1 XRVDGNKRPOAQTN-FQEVSTJZSA-N 0.000 description 1
- 206010061623 Adverse drug reaction Diseases 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- 208000016192 Demyelinating disease Diseases 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 210000003050 axon Anatomy 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 229940121657 clinical drug Drugs 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000007783 downstream signaling Effects 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 229950008141 ozanimod Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229940076155 protein modulator Drugs 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 231100000279 safety data Toxicity 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- 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
- A61K31/4245—Oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (23)
- PCT国内申请,权利要求书已公开。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2016106872065 | 2016-08-19 | ||
CN201610687206 | 2016-08-19 | ||
CN201610822328 | 2016-09-14 | ||
CN2016108223280 | 2016-09-14 | ||
PCT/CN2017/098125 WO2018033149A1 (zh) | 2016-08-19 | 2017-08-18 | 奥扎莫德的晶型及其制备方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN109563059A true CN109563059A (zh) | 2019-04-02 |
Family
ID=61196414
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201780045272.5A Pending CN109563059A (zh) | 2016-08-19 | 2017-08-18 | 奥扎莫德的晶型及其制备方法 |
Country Status (4)
Country | Link |
---|---|
US (2) | US11028060B2 (zh) |
EP (1) | EP3502100A1 (zh) |
CN (1) | CN109563059A (zh) |
WO (1) | WO2018033149A1 (zh) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11111223B2 (en) | 2016-06-14 | 2021-09-07 | Receptos Llc | Crystalline forms of ozanimod and ozanimod hydrochloride, and processes for preparation thereof |
WO2018033149A1 (zh) | 2016-08-19 | 2018-02-22 | 苏州科睿思制药有限公司 | 奥扎莫德的晶型及其制备方法 |
WO2018049632A1 (zh) * | 2016-09-14 | 2018-03-22 | 杭州领业医药科技有限公司 | 奥扎莫德的晶型、其制备方法及药物组合物 |
EP3630738B1 (en) * | 2017-05-22 | 2023-07-19 | Egis Gyógyszergyár Zrt. | Process for the production of ozanimod |
US11117876B2 (en) | 2017-08-31 | 2021-09-14 | Receptos Llc | Crystalline form of ozanimod hydrochloride, and processes for preparation thereof |
WO2019094409A1 (en) | 2017-11-07 | 2019-05-16 | Teva Pharmaceuticals International Gmbh | Salts and solid state forms of ozanimod |
MX2022000651A (es) | 2019-07-16 | 2022-03-11 | Synthon Bv | Proceso mejorado para preparar ozanimod. |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102762100A (zh) * | 2009-11-13 | 2012-10-31 | 瑞塞普托斯公司 | 选择性的1-磷酸鞘氨醇受体调节剂及手性合成方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101582910B1 (ko) * | 2008-05-14 | 2016-01-08 | 더 스크립스 리서치 인스티튜트 | 스핑고신 포스페이트 수용체의 신규한 모듈레이터 |
EA021672B1 (ru) | 2008-05-14 | 2015-08-31 | Дзе Скриппс Рисёч Инститьют | Модуляторы рецепторов сфингозин-1-фосфата и их применение |
US20170165236A1 (en) | 2013-11-01 | 2017-06-15 | Celgene International Ii Sàrl | Selective sphingosine 1 phosphate receptor modulators and combination therapy therewith |
US20180016244A1 (en) | 2015-04-06 | 2018-01-18 | Auspex Pharmaceuticals, Inc. | Deuterium-substituted oxadiazoles |
US11111223B2 (en) | 2016-06-14 | 2021-09-07 | Receptos Llc | Crystalline forms of ozanimod and ozanimod hydrochloride, and processes for preparation thereof |
WO2018033149A1 (zh) | 2016-08-19 | 2018-02-22 | 苏州科睿思制药有限公司 | 奥扎莫德的晶型及其制备方法 |
WO2018049632A1 (zh) * | 2016-09-14 | 2018-03-22 | 杭州领业医药科技有限公司 | 奥扎莫德的晶型、其制备方法及药物组合物 |
CN109640982A (zh) | 2016-09-14 | 2019-04-16 | 苏州科睿思制药有限公司 | 奥扎莫德盐酸盐的晶型及其制备方法 |
CN110612292A (zh) | 2017-04-07 | 2019-12-24 | 杭州领业医药科技有限公司 | 奥扎莫德加成盐晶型、制备方法及药物组合物和用途 |
US11117876B2 (en) | 2017-08-31 | 2021-09-14 | Receptos Llc | Crystalline form of ozanimod hydrochloride, and processes for preparation thereof |
CN107840830A (zh) | 2017-09-20 | 2018-03-27 | 广东东阳光药业有限公司 | 盐酸奥扎莫德无水晶型i |
-
2017
- 2017-08-18 WO PCT/CN2017/098125 patent/WO2018033149A1/zh unknown
- 2017-08-18 US US16/326,353 patent/US11028060B2/en active Active
- 2017-08-18 CN CN201780045272.5A patent/CN109563059A/zh active Pending
- 2017-08-18 EP EP17841121.1A patent/EP3502100A1/en not_active Withdrawn
-
2021
- 2021-06-04 US US17/339,080 patent/US11897848B2/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102762100A (zh) * | 2009-11-13 | 2012-10-31 | 瑞塞普托斯公司 | 选择性的1-磷酸鞘氨醇受体调节剂及手性合成方法 |
Also Published As
Publication number | Publication date |
---|---|
EP3502100A4 (en) | 2019-06-26 |
EP3502100A1 (en) | 2019-06-26 |
US20200216404A1 (en) | 2020-07-09 |
US20210292287A1 (en) | 2021-09-23 |
US11897848B2 (en) | 2024-02-13 |
US11028060B2 (en) | 2021-06-08 |
WO2018033149A1 (zh) | 2018-02-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109563059A (zh) | 奥扎莫德的晶型及其制备方法 | |
CN109640982A (zh) | 奥扎莫德盐酸盐的晶型及其制备方法 | |
CN109219597A (zh) | 奥扎莫德的晶型、其盐酸盐的晶型及其制备方法 | |
CN109195980B (zh) | 一种钠-葡萄糖协同转运蛋白抑制剂药物的新晶型及其制备方法和用途 | |
EP3858830B1 (en) | Crystal form of morpholino quinazoline compound, preparation method therefor and use thereof | |
CN104011047A (zh) | 选择性herb2抑制剂arry-380的多晶型物和含有它们的药物组合物 | |
CN108137516A (zh) | 奥扎莫德的晶型、其制备方法及药物组合物 | |
CN110156700A (zh) | 吉非替尼与水杨酸共晶体 | |
US9884856B2 (en) | Crystal form of Dabrafenib mesylate and preparation method thereof | |
CN109071531A (zh) | 用于治疗或预防jak相关疾病药物的盐酸盐晶型及其制备方法 | |
WO2023045360A1 (zh) | 大环类化合物的晶型及其制备方法和应用 | |
WO2023284804A1 (zh) | 一种石杉碱乙晶体及其制备和应用 | |
WO2019205812A1 (zh) | Acalabrutinib的新晶型及其制备方法和用途 | |
CN105992769B (zh) | 一种钠-葡萄糖协同转运蛋白2抑制剂的l-脯氨酸复合物、其一水合物及晶体 | |
WO2017107986A1 (zh) | 喹唑啉衍生物的晶体及其制备方法 | |
CN109476662A (zh) | 一种jak1选择性抑制剂的新晶型及其制备方法和用途 | |
WO2020192637A1 (zh) | 固体形式的brd4抑制剂化合物及其制备方法与应用 | |
CN110234639A (zh) | 替吡法尼的晶型及其制备方法及药物组合物 | |
CN105753732A (zh) | Ahu377的晶型及其制备方法与用途 | |
CN105753869B (zh) | 一种cdk抑制剂和mek抑制剂的共晶及其制备方法 | |
CN110036003A (zh) | Ap26113的新晶型及其制备方法 | |
CN105367492B (zh) | 他喹莫德的晶型及其制备方法、其药物组合物和用途 | |
WO2022067724A1 (zh) | 一种sglt-2抑制剂·肌氨酸共晶体及其制备方法和应用 | |
CN108299412A (zh) | 一种s1p1受体激动剂的加成盐及其晶型和药物组合物 | |
CN110386939B (zh) | Parp抑制剂的溶剂合物晶体及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20200929 Address after: California, USA Applicant after: Riseptos Co.,Ltd. Address before: 215123 Biological Park B4301, No. 218 Xing Hu Street, Suzhou Industrial Park, Jiangsu Applicant before: CRYSTAL PHARMACEUTICAL (SUZHOU) Co.,Ltd. |
|
TA01 | Transfer of patent application right | ||
CI02 | Correction of invention patent application |
Correction item: Applicant|Address Correct: RECEPTOS, Inc.|California, USA False: Riseptos Co.,Ltd.|California, USA Number: 43-02 Volume: 36 |
|
CI02 | Correction of invention patent application | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20190402 |
|
WD01 | Invention patent application deemed withdrawn after publication |