CN102724880B - 1-磷酸鞘氨醇受体调节剂及手性合成方法 - Google Patents
1-磷酸鞘氨醇受体调节剂及手性合成方法 Download PDFInfo
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- CN102724880B CN102724880B CN201080061143.3A CN201080061143A CN102724880B CN 102724880 B CN102724880 B CN 102724880B CN 201080061143 A CN201080061143 A CN 201080061143A CN 102724880 B CN102724880 B CN 102724880B
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- oxadiazol
- dihydro
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- 0 CC(C)Oc(c(*)c1)ccc1-c1nc(-c2c(CCCC3(*)*)c3ccc2)n[o]1 Chemical compound CC(C)Oc(c(*)c1)ccc1-c1nc(-c2c(CCCC3(*)*)c3ccc2)n[o]1 0.000 description 6
- LBHMMDUJKBJVQI-CYBMUJFWSA-N CC(C)(C)OC(N[C@H]1c2cccc(C#N)c2CC1)=O Chemical compound CC(C)(C)OC(N[C@H]1c2cccc(C#N)c2CC1)=O LBHMMDUJKBJVQI-CYBMUJFWSA-N 0.000 description 1
- QUJGMSDMKNCRRD-GFCCVEGCSA-N CC(C)(C)OC(N[C@H]1c2cccc(C(NO)=N)c2CC1)=O Chemical compound CC(C)(C)OC(N[C@H]1c2cccc(C(NO)=N)c2CC1)=O QUJGMSDMKNCRRD-GFCCVEGCSA-N 0.000 description 1
- OFQQYMHVEKNRBX-UHFFFAOYSA-N CC(C)(C)OC([n](cc1)c(cc2)c1cc2C(NO)=N)=O Chemical compound CC(C)(C)OC([n](cc1)c(cc2)c1cc2C(NO)=N)=O OFQQYMHVEKNRBX-UHFFFAOYSA-N 0.000 description 1
- WWKQXFAASLNEAC-DWGCHZBISA-N CC(C)OC(C)N(C)/C(/c1c(CCC[C@H]2N)c2ccc1)=N\O Chemical compound CC(C)OC(C)N(C)/C(/c1c(CCC[C@H]2N)c2ccc1)=N\O WWKQXFAASLNEAC-DWGCHZBISA-N 0.000 description 1
- HLHBUOGWMULDNM-UHFFFAOYSA-N CC(C)OC(C)NC Chemical compound CC(C)OC(C)NC HLHBUOGWMULDNM-UHFFFAOYSA-N 0.000 description 1
- ASXBRLPHELROKO-UHFFFAOYSA-N CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2c(CCCC3NC(N4CCCC4)=O)c3ccc2)n[o]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2c(CCCC3NC(N4CCCC4)=O)c3ccc2)n[o]1 ASXBRLPHELROKO-UHFFFAOYSA-N 0.000 description 1
- ZHHIQQKRFPVUAR-UHFFFAOYSA-N CC(C)Oc(ccc(-c1nc(-c(cc2)cc(cc3)c2[n]3C(OC(C)(C)C)=O)n[o]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1nc(-c(cc2)cc(cc3)c2[n]3C(OC(C)(C)C)=O)n[o]1)c1)c1C#N ZHHIQQKRFPVUAR-UHFFFAOYSA-N 0.000 description 1
- JBXGCJNDGPPSPT-LJQANCHMSA-N CC(C)Oc(ccc(-c1ncc(-c2c(CC[C@H]3N)c3ccc2)[o]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ncc(-c2c(CC[C@H]3N)c3ccc2)[o]1)c1)c1C#N JBXGCJNDGPPSPT-LJQANCHMSA-N 0.000 description 1
- YFDIKYHWUCCQCE-JOCHJYFZSA-N CC(C)Oc(ccc(-c1ncc(-c2c(CC[C@H]3NC(OC(C)(C)C)=O)c3ccc2)[o]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ncc(-c2c(CC[C@H]3NC(OC(C)(C)C)=O)c3ccc2)[o]1)c1)c1C#N YFDIKYHWUCCQCE-JOCHJYFZSA-N 0.000 description 1
- VWQUHTDSOMXBLA-VHEBOWPBSA-N CC([C@@H](C)N)/C=C\C(C)O Chemical compound CC([C@@H](C)N)/C=C\C(C)O VWQUHTDSOMXBLA-VHEBOWPBSA-N 0.000 description 1
- JPQAZAZNTRHOKX-DHZHZOJOSA-N CC/C(/NC(OC(C)(C)C)=O)=C\C(C)C(C)NO Chemical compound CC/C(/NC(OC(C)(C)C)=O)=C\C(C)C(C)NO JPQAZAZNTRHOKX-DHZHZOJOSA-N 0.000 description 1
- MCUXIXONBYPUII-PXRXIAQOSA-N CC/C(/[C@H](C)N(C)O)=C\C=C\O Chemical compound CC/C(/[C@H](C)N(C)O)=C\C=C\O MCUXIXONBYPUII-PXRXIAQOSA-N 0.000 description 1
- SXFQAFFSEZRQCJ-UHFFFAOYSA-N N#Cc1ccc2[o]ccc2c1 Chemical compound N#Cc1ccc2[o]ccc2c1 SXFQAFFSEZRQCJ-UHFFFAOYSA-N 0.000 description 1
- GSFCKZZACCGNJS-LLVKDONJSA-N N#Cc1cccc2c1CCC[C@H]2O Chemical compound N#Cc1cccc2c1CCC[C@H]2O GSFCKZZACCGNJS-LLVKDONJSA-N 0.000 description 1
- CKHFPPZDRHWRJI-SNVBAGLBSA-N N=C(c1cccc2c1CCC[C@H]2O)NO Chemical compound N=C(c1cccc2c1CCC[C@H]2O)NO CKHFPPZDRHWRJI-SNVBAGLBSA-N 0.000 description 1
- JEPCLNGRAIMPQV-UHFFFAOYSA-N Nc(c(O)ccc1)c1O Chemical compound Nc(c(O)ccc1)c1O JEPCLNGRAIMPQV-UHFFFAOYSA-N 0.000 description 1
- RPHKINMPYFJSCF-UHFFFAOYSA-N Nc1cc(N)cc(N)c1 Chemical compound Nc1cc(N)cc(N)c1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 1
- UVVYFYLSZIMKMC-UHFFFAOYSA-N O=C1c2cccc(Br)c2CC1 Chemical compound O=C1c2cccc(Br)c2CC1 UVVYFYLSZIMKMC-UHFFFAOYSA-N 0.000 description 1
- RNXQQZNOSYBFTN-UHFFFAOYSA-N OC(CC1)c2c1c(Br)ccc2 Chemical compound OC(CC1)c2c1c(Br)ccc2 RNXQQZNOSYBFTN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- 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
-
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
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- A61P37/02—Immunomodulators
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
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- 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
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Transplantation (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26128209P | 2009-11-13 | 2009-11-13 | |
| US61/261,282 | 2009-11-13 | ||
| US26247409P | 2009-11-18 | 2009-11-18 | |
| US61/262,474 | 2009-11-18 | ||
| PCT/US2010/056757 WO2011060389A1 (en) | 2009-11-13 | 2010-11-15 | Sphingosine 1 phosphate receptor modulators and methods of chiral synthesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102724880A CN102724880A (zh) | 2012-10-10 |
| CN102724880B true CN102724880B (zh) | 2016-09-14 |
Family
ID=43992104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080061143.3A Active CN102724880B (zh) | 2009-11-13 | 2010-11-15 | 1-磷酸鞘氨醇受体调节剂及手性合成方法 |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US8357706B2 (OSRAM) |
| EP (1) | EP2498611B1 (OSRAM) |
| JP (1) | JP5988379B2 (OSRAM) |
| KR (1) | KR101781233B1 (OSRAM) |
| CN (1) | CN102724880B (OSRAM) |
| AU (1) | AU2010320041B2 (OSRAM) |
| BR (1) | BR112012011430A8 (OSRAM) |
| CA (1) | CA2780433C (OSRAM) |
| CY (1) | CY1120427T1 (OSRAM) |
| DK (1) | DK2498611T3 (OSRAM) |
| EA (1) | EA023183B1 (OSRAM) |
| ES (1) | ES2665461T3 (OSRAM) |
| HR (1) | HRP20180527T1 (OSRAM) |
| HU (1) | HUE036391T2 (OSRAM) |
| IL (1) | IL219690B (OSRAM) |
| LT (1) | LT2498611T (OSRAM) |
| MX (1) | MX2012005562A (OSRAM) |
| MY (1) | MY160907A (OSRAM) |
| NZ (1) | NZ599913A (OSRAM) |
| PH (1) | PH12012500938A1 (OSRAM) |
| PL (1) | PL2498611T3 (OSRAM) |
| PT (1) | PT2498611T (OSRAM) |
| RS (1) | RS57070B1 (OSRAM) |
| SI (1) | SI2498611T1 (OSRAM) |
| WO (1) | WO2011060389A1 (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2498611T (pt) | 2009-11-13 | 2018-04-13 | Celgene Int Ii Sarl | Moduladores de recetor de esfingosina 1 fosfato e métodos de síntese quiral |
| CA2780772C (en) | 2009-11-13 | 2018-01-16 | Receptos, Inc. | Selective sphingosine 1 phosphate receptor modulators and methods of chiral synthesis |
| ES2758841T3 (es) | 2011-05-13 | 2020-05-06 | Celgene Int Ii Sarl | Moduladores heterocíclicos selectivos del receptor de la esfingosina-1-fosfato |
| CN103251950B (zh) * | 2012-02-16 | 2018-10-02 | 中国人民解放军军事科学院军事医学研究院辐射医学研究所 | S1p受体调节剂防治肠型放射病及放射性肠炎的用途 |
| CA2885155C (en) * | 2012-11-16 | 2021-02-16 | F. Hoffmann-La Roche Ag | Process for the preparation of 2-trifluoromethyl isonicotinic acid and esters |
| US9540362B2 (en) | 2013-02-20 | 2017-01-10 | Lg Life Sciences Ltd. | Sphingosine-1-phosphate receptor agonists, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent |
| EP3062792A1 (en) * | 2013-11-01 | 2016-09-07 | Celgene International II Sarl | Selective sphingosine 1 phosphate receptor modulators and combination therapy therewith |
| DK3373931T3 (da) | 2015-11-13 | 2022-11-28 | Oppilan Pharma Ltd | Heterocykliske forbindelser til behandling af sygdom |
| US10280159B2 (en) | 2015-12-22 | 2019-05-07 | AbbVie Deutschland GmbH & Co. KG | Fused (hetero)cyclic compounds as S1P modulators |
| AU2017257151A1 (en) * | 2016-04-29 | 2018-11-15 | Board Of Regents, The University Of Texas System | Sigma receptor binders |
| JP6883882B2 (ja) * | 2016-07-22 | 2021-06-09 | シージャーズォアン サガシティ ニュー ドラッグ デベロップメント カンパニー リミテッド | Ｓ１ｐ１アゴニスト及びその応用 |
| CN106749213B (zh) * | 2016-11-25 | 2019-07-02 | 济南大学 | 一种具有1,2,4-恶二唑结构的吲哚衍生物及制备方法和在制备抗菌药物中的应用 |
| CN108727291A (zh) * | 2017-04-21 | 2018-11-02 | 宁波爱诺医药科技有限公司 | 奥扎莫德及其中间体的制备方法 |
| CN108727292A (zh) * | 2017-04-21 | 2018-11-02 | 宁波爱诺医药科技有限公司 | 一种奥扎莫德及其中间体的制备方法 |
| AR116479A1 (es) | 2018-09-25 | 2021-05-12 | Quim Sintetica S A | Intermediarios para la síntesis de ozanimod y procedimiento para la preparación del mencionado agonista del receptor de esfingosina-1-fosfato y de dichos intermediarios |
| CN110256288A (zh) * | 2019-05-13 | 2019-09-20 | 苏州山青竹生物医药有限公司 | 一种制备(s)-1-氨基-2,3-二氢-1h-茚-4-甲腈的方法 |
| CN112062785B (zh) * | 2019-06-11 | 2023-06-27 | 广东东阳光药业有限公司 | 奥扎莫德及其中间体的制备方法 |
| TW202135804A (zh) * | 2020-01-06 | 2021-10-01 | 美商艾尼納製藥公司 | 治療與s1p1受體相關之病況的方法 |
| CN118662488A (zh) | 2020-02-06 | 2024-09-20 | 田边三菱制药株式会社 | 肌痛性脑脊髓炎/慢性疲劳症候群治疗剂 |
| EP4116295A4 (en) * | 2020-03-04 | 2023-08-02 | Helioeast Pharmaceutical Co., Ltd. | TRICYCLIC COMPOUNDS AND THEIR USE |
| WO2024246174A1 (en) | 2023-05-31 | 2024-12-05 | Química Sintética, S.A. | Amorphous and crystalline form of ozanimod hydrochloride |
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| GB2290790A (en) * | 1994-06-30 | 1996-01-10 | Merck & Co Inc | Asymmetric synthesis of 6-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes |
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