RU2365374C2 - Лекарственный состав для ингибирования репродукции вируса иммунодефицита человека - Google Patents

Лекарственный состав для ингибирования репродукции вируса иммунодефицита человека Download PDF

Info

Publication number: RU2365374C2
Authority: RU; Russia
Prior art keywords: glycyrrhizic acid; sodium carbonate; trinicotinates; human immunodeficiency; immunodeficiency virus
Prior art date: 2006-09-18

Application number

RU2006133168/15A

Other languages

English (en)

Russian (ru)

Other versions

RU2006133168A (ru

Inventor

Генрих Александрович Толстиков (RU)

Генрих Александрович Толстиков

Андрей Георгиевич Покровский (RU)

Андрей Георгиевич Покровский

Нариман Фаридович Салахутдинов (RU)

Нариман Фаридович Салахутдинов

Original Assignee

Общество с ограниченной ответственностью "Сибфармакон" (ООО "Сибфармакон")

Priority date (The priority date 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 date listed.)

2006-09-18

Filing date

2006-09-18

Publication date

2009-08-27

2006-09-18 Application filed by Общество с ограниченной ответственностью "Сибфармакон" (ООО "Сибфармакон") filed Critical Общество с ограниченной ответственностью "Сибфармакон" (ООО "Сибфармакон")

2006-09-18 Priority to RU2006133168/15A priority Critical patent/RU2365374C2/ru

2006-11-02 Priority to PCT/RU2006/000573 priority patent/WO2008035998A1/fr

2008-03-27 Publication of RU2006133168A publication Critical patent/RU2006133168A/ru

2009-08-27 Application granted granted Critical

2009-08-27 Publication of RU2365374C2 publication Critical patent/RU2365374C2/ru

Links

241000725303 Human immunodeficiency virus Species 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 title abstract description 10
230000005764 inhibitory process Effects 0.000 title abstract description 3
LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical class O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims abstract description 46
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 36
VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 claims abstract description 35
LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims abstract description 35
229960004949 glycyrrhizic acid Drugs 0.000 claims abstract description 35
UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims abstract description 35
239000001685 glycyrrhizic acid Substances 0.000 claims abstract description 35
235000019410 glycyrrhizin Nutrition 0.000 claims abstract description 35
229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 18
239000000203 mixture Substances 0.000 claims description 13
230000002401 inhibitory effect Effects 0.000 claims description 2
239000003814 drug Substances 0.000 abstract description 13
230000000694 effects Effects 0.000 abstract description 7
239000003112 inhibitor Substances 0.000 abstract description 3
235000001968 nicotinic acid Nutrition 0.000 abstract description 3
239000000126 substance Substances 0.000 abstract description 2
-1 glycyrrhizic acid nicotinates Chemical class 0.000 abstract 2
229940079593 drug Drugs 0.000 description 8
239000002253 acid Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
241000700159 Rattus Species 0.000 description 5
241000700605 Viruses Species 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
230000004071 biological effect Effects 0.000 description 4
230000007423 decrease Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
230000003612 virological effect Effects 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000000840 anti-viral effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011664 nicotinic acid Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000202807 Glycyrrhiza Species 0.000 description 2
235000006200 Glycyrrhiza glabra Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000036436 anti-hiv Effects 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
238000012797 qualification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 1
GBYYTNDVCDADIY-HCWSKCQFSA-N 1-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-iodooxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@@]1(I)N1C(=O)NC(=O)C=C1 GBYYTNDVCDADIY-HCWSKCQFSA-N 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
241000450599 DNA viruses Species 0.000 description 1
102000002068 Glycopeptides Human genes 0.000 description 1
108010015899 Glycopeptides Proteins 0.000 description 1
MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 description 1
235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
244000303040 Glycyrrhiza glabra Species 0.000 description 1
235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
206010019799 Hepatitis viral Diseases 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
208000007514 Herpes zoster Diseases 0.000 description 1
241000701806 Human papillomavirus Species 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
229910013684 LiClO 4 Inorganic materials 0.000 description 1
241001115401 Marburgvirus Species 0.000 description 1
108091000080 Phosphotransferase Proteins 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960004150 aciclovir Drugs 0.000 description 1
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000001139 anti-pruritic effect Effects 0.000 description 1
239000003908 antipruritic agent Substances 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000012620 biological material Substances 0.000 description 1
210000000234 capsid Anatomy 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
229940088679 drug related substance Drugs 0.000 description 1
241001493065 dsRNA viruses Species 0.000 description 1
229960003720 enoxolone Drugs 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000002519 immonomodulatory effect Effects 0.000 description 1
230000036039 immunity Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
229940010454 licorice Drugs 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
231100000590 oncogenic Toxicity 0.000 description 1
230000002246 oncogenic effect Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
230000000865 phosphorylative effect Effects 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000010076 replication Effects 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
201000001862 viral hepatitis Diseases 0.000 description 1
210000002845 virion Anatomy 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P31/18—Antivirals for RNA viruses for HIV

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Virology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
AIDS & HIV (AREA)
Chemical Kinetics & Catalysis (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

RU2006133168/15A 2006-09-18 2006-09-18 Лекарственный состав для ингибирования репродукции вируса иммунодефицита человека RU2365374C2 (ru)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
RU2006133168/15A RU2365374C2 (ru)	2006-09-18	2006-09-18	Лекарственный состав для ингибирования репродукции вируса иммунодефицита человека
PCT/RU2006/000573 WO2008035998A1 (fr)	2006-09-18	2006-11-02	Formulation médicinale destinée à inhiber la propagation du virus de l'immunodéficience humaine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
RU2006133168/15A RU2365374C2 (ru)	2006-09-18	2006-09-18	Лекарственный состав для ингибирования репродукции вируса иммунодефицита человека

Publications (2)

Publication Number	Publication Date
RU2006133168A RU2006133168A (ru)	2008-03-27
RU2365374C2 true RU2365374C2 (ru)	2009-08-27

Family

ID=39200740

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
RU2006133168/15A RU2365374C2 (ru)	2006-09-18	2006-09-18	Лекарственный состав для ингибирования репродукции вируса иммунодефицита человека

Country Status (2)

Country	Link
RU (1)	RU2365374C2 (fr)
WO (1)	WO2008035998A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2834426C2 (ru) *	2023-03-28	2025-02-07	Алексей Владимирович Тарасевич	Способ лечения вирусных инфекций и композиция для его осуществления

Citations (2)

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SU1625882A1 (ru) *	1988-10-04	1991-02-07	Институт химии Башкирского научного центра Уральского отделения АН СССР	Способ получени гликопептидов глицирризиновой кислоты
RU2024546C1 (ru) *	1991-03-04	1994-12-15	Институт органической химии УНЦ РАН	ГЛИКОПЕПТИД β-ГЛИЦИРРИЗИНОВОЙ КИСЛОТЫ С ДИБУТИЛОВЫМ ЭФИРОМ L-ГЛУТАМИНОВОЙ КИСЛОТЫ, ПРОЯВЛЯЮЩИЙ АНТИ-СПИД-АКТИВНОСТЬ

Family Cites Families (1)

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RU2272631C2 (ru) *	2004-04-20	2006-03-27	Государственный научный центр вирусологии и биотехнологии "Вектор" (ГНЦ ВБ "Вектор")	Синергическая композиция для ингибирования вич

2006
- 2006-09-18 RU RU2006133168/15A patent/RU2365374C2/ru not_active IP Right Cessation
- 2006-11-02 WO PCT/RU2006/000573 patent/WO2008035998A1/fr not_active Ceased

Patent Citations (2)

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Publication number	Priority date	Publication date	Assignee	Title
SU1625882A1 (ru) *	1988-10-04	1991-02-07	Институт химии Башкирского научного центра Уральского отделения АН СССР	Способ получени гликопептидов глицирризиновой кислоты
RU2024546C1 (ru) *	1991-03-04	1994-12-15	Институт органической химии УНЦ РАН	ГЛИКОПЕПТИД β-ГЛИЦИРРИЗИНОВОЙ КИСЛОТЫ С ДИБУТИЛОВЫМ ЭФИРОМ L-ГЛУТАМИНОВОЙ КИСЛОТЫ, ПРОЯВЛЯЮЩИЙ АНТИ-СПИД-АКТИВНОСТЬ

Non-Patent Citations (1)

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Title
TOLSTIKOV G.A. et al. Transformation of glycyrrhizic acid. Synthesis of glycopeptides of glycyrrhizic acid monomethyl ether, having anti-inflammatory and immunostimulating action. Bioorg. Khim. 1989; 15(3): 392-8. Реферат Entrez-PubMed. HOEVER G. et al. Antiviral activity of glycyrrhizic acid derivatives against SARS-coronavirus. J. Med. Chem. 2005; 48(4): 1256-9. ПЛЯСУНОВА О.А., ЕГОРИЧЕВА И.Н., ФЕДЮК Н.В. и др. Изучение анти-ВИЧ активности β-глицирризиновой кислоты. Вопросы вирусологии.. N 5-6, с.235-238. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2834426C2 (ru) *	2023-03-28	2025-02-07	Алексей Владимирович Тарасевич	Способ лечения вирусных инфекций и композиция для его осуществления

Also Published As

Publication number	Publication date
RU2006133168A (ru)	2008-03-27
WO2008035998A1 (fr)	2008-03-27

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Legal Events

Date	Code	Title	Description
2008-09-10	FZ9A	Application not withdrawn (correction of the notice of withdrawal)	Effective date: 20080718
2010-09-10	PC4A	Invention patent assignment	Effective date: 20100727
2011-12-10	MM4A	The patent is invalid due to non-payment of fees	Effective date: 20100919
2013-04-20	NF4A	Reinstatement of patent	Effective date: 20130420
2017-05-30	MM4A	The patent is invalid due to non-payment of fees	Effective date: 20160919

RU2365374C2 - Лекарственный состав для ингибирования репродукции вируса иммунодефицита человека - Google Patents

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