RU2019131478A - Соединения формул (I) и (I'), фармацевтическая композиция, лекарственное средство, способ получения соединения - Google Patents
Соединения формул (I) и (I'), фармацевтическая композиция, лекарственное средство, способ получения соединения Download PDFInfo
- Publication number
- RU2019131478A RU2019131478A RU2019131478A RU2019131478A RU2019131478A RU 2019131478 A RU2019131478 A RU 2019131478A RU 2019131478 A RU2019131478 A RU 2019131478A RU 2019131478 A RU2019131478 A RU 2019131478A RU 2019131478 A RU2019131478 A RU 2019131478A
- Authority
- RU
- Russia
- Prior art keywords
- iia
- pharmaceutically acceptable
- formula
- compound
- iiia
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 23
- 229940126601 medicinal product Drugs 0.000 title claims 2
- 238000000034 method Methods 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- -1 nitro, carboxy Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000006950 reactive oxygen species formation Effects 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- IWBBKLMHAILHAR-UHFFFAOYSA-N chembl402341 Chemical compound C1=CC(O)=CC=C1C1=CC(=S)SS1 IWBBKLMHAILHAR-UHFFFAOYSA-N 0.000 claims 2
- 210000003470 mitochondria Anatomy 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000003642 reactive oxygen metabolite Substances 0.000 claims 2
- FZNSULGQTRGDDF-UHFFFAOYSA-N 4-(4-hydroxyphenyl)dithiole-3-thione Chemical compound C1=CC(O)=CC=C1C1=CSSC1=S FZNSULGQTRGDDF-UHFFFAOYSA-N 0.000 claims 1
- GEOXNKHTZAUVBM-UHFFFAOYSA-N 4-(5-hydroxyiminodithiol-3-yl)phenol Chemical compound OC1=CC=C(C=C1)C1=CC(SS1)=NO GEOXNKHTZAUVBM-UHFFFAOYSA-N 0.000 claims 1
- KDJVJTMHWXZZJJ-UHFFFAOYSA-N 5-(1-benzofuran-5-yl)dithiole-3-thione Chemical compound O1C=CC2=C1C=CC(=C2)C1=CC(SS1)=S KDJVJTMHWXZZJJ-UHFFFAOYSA-N 0.000 claims 1
- HLFFXEFJKQLPTQ-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-1,2,4-dithiazole-3-thione Chemical compound OC1=CC=C(C=C1)C1=NC(SS1)=S HLFFXEFJKQLPTQ-UHFFFAOYSA-N 0.000 claims 1
- XXDYQIINMXOSSO-UHFFFAOYSA-N 5-(4-hydroxyphenyl)dithiol-3-one Chemical compound C1=CC(O)=CC=C1C1=CC(=O)SS1 XXDYQIINMXOSSO-UHFFFAOYSA-N 0.000 claims 1
- MYTUEHUXUXSJCN-UHFFFAOYSA-N 5-(5-sulfanylidenedithiol-3-yl)-3H-1,3-benzoxazol-2-one Chemical compound OC=1OC2=C(N=1)C=C(C=C2)C1=CC(SS1)=S MYTUEHUXUXSJCN-UHFFFAOYSA-N 0.000 claims 1
- CMAFOEYOQDEIOR-UHFFFAOYSA-N 6-(5-sulfanylidenedithiol-3-yl)-3H-1,3-benzothiazol-2-one Chemical compound OC1=NC2=CC=C(C=C2S1)C1=CC(=S)SS1 CMAFOEYOQDEIOR-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010048610 Cardiotoxicity Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 201000006306 Cor pulmonale Diseases 0.000 claims 1
- 206010014523 Embolism and thrombosis Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 208000029578 Muscle disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 208000027089 Parkinsonian disease Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical group CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 231100000259 cardiotoxicity Toxicity 0.000 claims 1
- 230000007681 cardiovascular toxicity Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 208000037906 ischaemic injury Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- TZVDSZGVPRAWHE-UHFFFAOYSA-N methyl 5-(5-sulfanylidenedithiol-3-yl)indole-1-carboxylate Chemical compound S=C1SSC(=C1)C=1C=C2C=CN(C2=CC=1)C(=O)OC TZVDSZGVPRAWHE-UHFFFAOYSA-N 0.000 claims 1
- 230000002438 mitochondrial effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000018329 progeroid syndrome Diseases 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
-
- 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
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic 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
- A61K31/41—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
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762467874P | 2017-03-07 | 2017-03-07 | |
| US62/467,874 | 2017-03-07 | ||
| EP1715969.9 | 2017-03-07 | ||
| EP17159691 | 2017-03-07 | ||
| PCT/EP2018/055651 WO2018162581A1 (en) | 2017-03-07 | 2018-03-07 | Desmethylanethole trithione derivatives for the treatment of diseases linked to mitochondrial reactive oxygen species (ros) production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2019131478A true RU2019131478A (ru) | 2021-04-07 |
| RU2019131478A3 RU2019131478A3 (enExample) | 2021-07-09 |
Family
ID=61628329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2019131478A RU2019131478A (ru) | 2017-03-07 | 2018-03-07 | Соединения формул (I) и (I'), фармацевтическая композиция, лекарственное средство, способ получения соединения |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US11484529B2 (enExample) |
| EP (1) | EP3592348A1 (enExample) |
| JP (1) | JP2020511450A (enExample) |
| KR (1) | KR20190129900A (enExample) |
| CN (1) | CN110662535A (enExample) |
| AU (1) | AU2018232799B2 (enExample) |
| BR (1) | BR112019018495A2 (enExample) |
| CA (1) | CA3055122A1 (enExample) |
| IL (1) | IL269127A (enExample) |
| RU (1) | RU2019131478A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL281161B2 (en) * | 2018-09-06 | 2024-01-01 | OP2 Drugs | Pharmaceutical composition comprising cyclodextrin compexes of anethole trithione or derivatives thereof |
| CN112546216B (zh) * | 2020-11-20 | 2022-10-28 | 西湖大学 | 小分子化合物奥替普拉在制备增强体液免疫应答的药物中的应用 |
| WO2022123038A1 (en) * | 2020-12-10 | 2022-06-16 | OP2 Drugs | Anethole trithione administration regimen for the prevention or treatment of ischemia-reperfusion injuries |
| EP4291552B1 (en) * | 2021-02-09 | 2025-04-09 | Boehringer Ingelheim International GmbH | Modulators of complex i |
| CN114414332B (zh) * | 2022-01-05 | 2024-04-16 | 北京科技大学 | 一种基于Al-CQDs和Al-CNSs的抗氧化剂的制备方法 |
| CN119185368A (zh) * | 2024-09-26 | 2024-12-27 | 中南大学 | 具有线粒体序贯靶向能力的强抗氧化性纳米药物及其制备方法和应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5474198A (en) * | 1996-12-24 | 1998-07-17 | National Research Council Of Canada | Treatment of diseases or prevention of cellular damage caused by oxygen-containing free radicals |
| WO2001009118A2 (en) * | 1999-07-29 | 2001-02-08 | Patrick T Prendergast | Dithiolthione compounds for the treatment of neurological disorders and for memory enhancement |
| KR20030067935A (ko) | 2002-02-09 | 2003-08-19 | 김상건 | 올티프라즈를 포함하는 간경화(간경변증) 치료를 위한 간 조직 재생용 제약 조성물 |
| DE60140668D1 (de) * | 2000-05-22 | 2010-01-14 | Clarion Co Ltd | Plattenspieler |
| CN1355156A (zh) * | 2000-11-27 | 2002-06-26 | 朱国和 | 含有造纸废料污泥的微生物菌肥及其制备方法 |
| CN1244325C (zh) | 2001-05-11 | 2006-03-08 | 成都国嘉联合制药有限公司 | 胆维他在制药中的应用 |
| US7199122B2 (en) | 2001-10-02 | 2007-04-03 | Fox Chase Cancer Center | Methods for inhibiting angiogenesis |
| DE60309834D1 (de) | 2002-02-13 | 2007-01-04 | Solvay Pharma | Verwendung von anethol-dithiolethion zur vorbeugung von lungenkrebs |
| TW200640898A (en) | 2005-02-24 | 2006-12-01 | Solvay Pharm Bv | Anethole dithiolethione and other dithiolethiones for the treatment of conditions associated with dysfunction of monoamine neurotransmission |
| WO2008106640A1 (en) | 2007-03-01 | 2008-09-04 | Cedars-Sinai Medical Center | Antioxidant polymers containing [1,2]-dithiolane moieties and uses thereof |
| CN102807557B (zh) * | 2012-08-21 | 2015-02-04 | 苏州大学 | 3h-1,2-二硫环戊烯-3-硫酮类化合物及其应用 |
| CN102961376B (zh) * | 2012-11-06 | 2015-06-10 | 暨南大学 | HMG-CoA还原酶抑制剂氟伐他汀在制备抗淋巴瘤药物中的应用 |
| CN102961375B (zh) | 2012-12-05 | 2015-01-14 | 苏州大学 | 一种ampk激活剂及其在制备治疗糖尿病和/或糖尿病并发症的药物中的应用 |
-
2018
- 2018-03-07 RU RU2019131478A patent/RU2019131478A/ru unknown
- 2018-03-07 CN CN201880029927.4A patent/CN110662535A/zh active Pending
- 2018-03-07 JP JP2019548696A patent/JP2020511450A/ja active Pending
- 2018-03-07 AU AU2018232799A patent/AU2018232799B2/en not_active Ceased
- 2018-03-07 CA CA3055122A patent/CA3055122A1/en active Pending
- 2018-03-07 KR KR1020197028579A patent/KR20190129900A/ko not_active Ceased
- 2018-03-07 BR BR112019018495A patent/BR112019018495A2/pt not_active IP Right Cessation
- 2018-03-07 EP EP18711055.6A patent/EP3592348A1/en not_active Withdrawn
- 2018-03-07 US US16/491,617 patent/US11484529B2/en active Active
-
2019
- 2019-09-04 IL IL26912719A patent/IL269127A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20190129900A (ko) | 2019-11-20 |
| EP3592348A1 (en) | 2020-01-15 |
| IL269127A (en) | 2019-11-28 |
| AU2018232799A1 (en) | 2019-10-03 |
| RU2019131478A3 (enExample) | 2021-07-09 |
| US11484529B2 (en) | 2022-11-01 |
| CA3055122A1 (en) | 2018-09-13 |
| US20210154175A1 (en) | 2021-05-27 |
| AU2018232799B2 (en) | 2021-11-25 |
| CN110662535A (zh) | 2020-01-07 |
| JP2020511450A (ja) | 2020-04-16 |
| BR112019018495A2 (pt) | 2020-04-14 |
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