EA024643B1 - КЛАТРАТНЫЕ КОМПЛЕКСЫ β-ЦИКЛОДЕКСТРИНА С ПРОИЗВОДНЫМ 5-ГИДРОКСИ-4-АМИНОМЕТИЛ-1-ЦИКЛОГЕКСИЛ( ИЛИ ЦИКЛОГЕПТИЛ)-3-АЛКОКСИКАРБОНИЛИНДОЛА, ОБЛАДАЮЩИЕ ПРОТИВОВИРУСНЫМ ДЕЙСТВИЕМ, И СПОСОБЫ ИХ ПОЛУЧЕНИЯ - Google Patents

КЛАТРАТНЫЕ КОМПЛЕКСЫ β-ЦИКЛОДЕКСТРИНА С ПРОИЗВОДНЫМ 5-ГИДРОКСИ-4-АМИНОМЕТИЛ-1-ЦИКЛОГЕКСИЛ( ИЛИ ЦИКЛОГЕПТИЛ)-3-АЛКОКСИКАРБОНИЛИНДОЛА, ОБЛАДАЮЩИЕ ПРОТИВОВИРУСНЫМ ДЕЙСТВИЕМ, И СПОСОБЫ ИХ ПОЛУЧЕНИЯ Download PDF

Info

Publication number: EA024643B1
Authority: EA; Eurasian Patent Office
Prior art keywords: hydroxy; cyclohexyl; aminomethyl; cycloheptyl; cyclodextrin
Prior art date: 2011-03-31

Application number

EA201370198A

Other languages

English (en)

Russian (ru)

Other versions

EA201370198A1 (ru

Inventor

Анатолий Федорович ЦЫБ

Анна Яковлевна ГОНЧАРОВА

Рахимджан Ахметджанович РОЗИЕВ

Илья Владимирович ВОРОБЬЕВ

Владимир Константинович ПОДГОРОДНИЧЕНКО

Виктор Владимирович ХОМИЧЕНОК

Original Assignee

Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания" Медбиофарм"

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.)

2011-03-31

Filing date

2012-03-27

Publication date

2016-10-31

2012-03-27 Application filed by Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания" Медбиофарм" filed Critical Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания" Медбиофарм"

2014-01-30 Publication of EA201370198A1 publication Critical patent/EA201370198A1/ru

2016-10-31 Publication of EA024643B1 publication Critical patent/EA024643B1/ru

Links

229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 61
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims abstract description 51
235000011175 beta-cyclodextrine Nutrition 0.000 title claims abstract description 46
239000001116 FEMA 4028 Substances 0.000 title claims abstract description 45
229960004853 betadex Drugs 0.000 title claims abstract description 45
-1 5-hydroxy-4-aminomethyl-1-cyclohexyl Chemical group 0.000 title claims abstract description 42
230000000840 anti-viral effect Effects 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims description 25
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
239000002105 nanoparticle Substances 0.000 claims abstract description 12
238000010532 solid phase synthesis reaction Methods 0.000 claims abstract description 8
239000007791 liquid phase Substances 0.000 claims abstract description 7
LVYUPANIUOJDGE-UHFFFAOYSA-N ethyl 4-(aminomethyl)-1-cyclohexyl-5-hydroxy-2-methylindole-3-carboxylate Chemical group C12=CC=C(O)C(CN)=C2C(C(=O)OCC)=C(C)N1C1CCCCC1 LVYUPANIUOJDGE-UHFFFAOYSA-N 0.000 claims abstract description 5
241000712461 unidentified influenza virus Species 0.000 claims abstract 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 35
238000000227 grinding Methods 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
239000000243 solution Substances 0.000 claims description 9
239000002552 dosage form Substances 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 5
238000003756 stirring Methods 0.000 claims description 5
239000002775 capsule Substances 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
206010022000 influenza Diseases 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000003826 tablet Substances 0.000 claims description 4
206010035664 Pneumonia Diseases 0.000 claims description 3
125000004494 ethyl ester group Chemical group 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
239000007924 injection Substances 0.000 claims description 3
238000002347 injection Methods 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000000460 chlorine Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000945 filler Substances 0.000 claims description 2
239000012456 homogeneous solution Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000011630 iodine Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
BHFYJMNOBRLYSC-UHFFFAOYSA-N 2-methyl-1h-indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C)NC2=C1 BHFYJMNOBRLYSC-UHFFFAOYSA-N 0.000 claims 2
241000712431 Influenza A virus Species 0.000 claims 1
241000713196 Influenza B virus Species 0.000 claims 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
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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 description 17
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 13
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241000700605 Viruses Species 0.000 description 6
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239000002904 solvent Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000000654 additive Substances 0.000 description 5
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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239000000126 substance Substances 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
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GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
QBZGLPNNABDLMW-UHFFFAOYSA-N CCOC(=O)C1=C(N(C2=CC=CC(=C21)C)C3CCCCC3)C Chemical compound CCOC(=O)C1=C(N(C2=CC=CC(=C21)C)C3CCCCC3)C QBZGLPNNABDLMW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
229960004150 aciclovir Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000004913 activation Effects 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 2
239000003443 antiviral agent Substances 0.000 description 2
230000008859 change Effects 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229940097362 cyclodextrins Drugs 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
238000011161 development Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
230000008569 process Effects 0.000 description 2
238000012216 screening Methods 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
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238000011287 therapeutic dose Methods 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
VYITUJFLKQKLLW-UHFFFAOYSA-N 4-(aminomethyl)-1-cyclohexyl-5-hydroxy-2-methylindole-3-carboxylic acid Chemical compound C1(CCCCC1)N1C(=C(C2=C(C(=CC=C12)O)CN)C(=O)O)C VYITUJFLKQKLLW-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
UZDMDPCTGLFVIV-UHFFFAOYSA-N CCOC(=O)C1=C(N(C2=C1C(=C(C=C2)O)CN)C3CCCCC3)C.Cl Chemical compound CCOC(=O)C1=C(N(C2=C1C(=C(C=C2)O)CN)C3CCCCC3)C.Cl UZDMDPCTGLFVIV-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
YLCXGBZIZBEVPZ-UHFFFAOYSA-N Medazepam Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=CC=CC=C1 YLCXGBZIZBEVPZ-UHFFFAOYSA-N 0.000 description 1
239000004909 Moisturizer Substances 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
LBQHRYLMGOPITI-UHFFFAOYSA-N OC=1C(=C2C(=C(N(C2=CC=1)C1CCCCC1)C)C(=O)OCC)CN(CC)CC Chemical compound OC=1C(=C2C(=C(N(C2=CC=1)C1CCCCC1)C)C(=O)OCC)CN(CC)CC LBQHRYLMGOPITI-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
230000009471 action Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
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125000000217 alkyl group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
229940097217 cardiac glycoside Drugs 0.000 description 1
239000002368 cardiac glycoside Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000010835 comparative analysis Methods 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
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NEZHOHUTJPXQRC-UHFFFAOYSA-N ethyl 1-cycloheptyl-4-[(dimethylamino)methyl]-5-hydroxy-2-methylindole-3-carboxylate Chemical compound C12=CC=C(O)C(CN(C)C)=C2C(C(=O)OCC)=C(C)N1C1CCCCCC1 NEZHOHUTJPXQRC-UHFFFAOYSA-N 0.000 description 1
BMBROEAVSISUSK-UHFFFAOYSA-N ethyl 1-cyclohexyl-4-(dimethylamino)-5-hydroxy-2-methylindole-3-carboxylate Chemical compound C12=CC=C(O)C(N(C)C)=C2C(C(=O)OCC)=C(C)N1C1CCCCC1 BMBROEAVSISUSK-UHFFFAOYSA-N 0.000 description 1
FTILETWSRMKYSA-UHFFFAOYSA-N ethyl 1-cyclohexyl-5-hydroxy-2-methyl-4-(morpholin-4-ylmethyl)indole-3-carboxylate Chemical compound C12=CC=C(O)C(CN3CCOCC3)=C2C(C(=O)OCC)=C(C)N1C1CCCCC1 FTILETWSRMKYSA-UHFFFAOYSA-N 0.000 description 1
ZIVZRNQZNHVVGT-UHFFFAOYSA-N ethyl 6-chloro-1-cyclohexyl-4-[(dimethylamino)methyl]-2-ethyl-5-hydroxyindole-3-carboxylate Chemical compound C12=CC(Cl)=C(O)C(CN(C)C)=C2C(C(=O)OCC)=C(CC)N1C1CCCCC1 ZIVZRNQZNHVVGT-UHFFFAOYSA-N 0.000 description 1
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235000003599 food sweetener Nutrition 0.000 description 1
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DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
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TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
- 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
- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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EA201370198A 2011-03-31 2012-03-27 КЛАТРАТНЫЕ КОМПЛЕКСЫ β-ЦИКЛОДЕКСТРИНА С ПРОИЗВОДНЫМ 5-ГИДРОКСИ-4-АМИНОМЕТИЛ-1-ЦИКЛОГЕКСИЛ( ИЛИ ЦИКЛОГЕПТИЛ)-3-АЛКОКСИКАРБОНИЛИНДОЛА, ОБЛАДАЮЩИЕ ПРОТИВОВИРУСНЫМ ДЕЙСТВИЕМ, И СПОСОБЫ ИХ ПОЛУЧЕНИЯ EA024643B1 (ru)

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RU2011112073/04A RU2464042C1 (ru)	2011-03-31	2011-03-31	КЛАТРАТНЫЙ КОМПЛЕКС β-ЦИКЛОДЕКСТРИНА С ПРОИЗВОДНЫМ 5-ГИДРОКСИ-4-АМИНОМЕТИЛ-1-ЦИКЛОГЕКСИЛ(ИЛИ ЦИКЛОГЕПТИЛ)-3-АЛКОКСИКАРБОНИЛИНДОЛА, СПОСОБ ЕГО ПОЛУЧЕНИЯ (ВАРИАНТЫ), ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И ЛЕКАРСТВЕННОЕ СРЕДСТВО
PCT/RU2012/000222 WO2012134351A1 (fr)	2011-03-31	2012-03-27	COMPLEXES DE CLATHRATES DE β-CYCLODEXTRINE ET DES DÉRIVÉS DE 5-HYDROXY-4-AMINOMÉTHYL-1-CYCLOHEXYL (OU CYCLOHEPTYL)-3-ALCOXYCARBONYLE INDOLE POSSÉDANT UN EFFET ANTIVIRAL ET PROCÉDÉ DE LEUR PRODUCTION

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RU2570382C1 (ru) *	2014-12-10	2015-12-10	Общество с ограниченной ответственностью "ЛАЙФ САЙНСЕС ОХФК"	Фармацевтическая композиция и лекарственное средство на основе клатратного комплекса 7-бром-5-(орто-хлорфенил)-2,3-дигидро-1н-1,4-бензодиазепин-2-она с циклодекстрином, способы его получения (варианты)
RU2761429C2 (ru) *	2018-06-13	2021-12-08	Общество с ограниченной ответственностью "Тиацен"	Средство, обладающее противоопухолевым действием, для лечения онкологических заболеваний

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2012
- 2012-03-27 WO PCT/RU2012/000222 patent/WO2012134351A1/fr not_active Ceased
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WO2012134351A1 (fr)	2012-10-04
RU2464042C1 (ru)	2012-10-20

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