PH26159A - Antiviral pharmaceutical compositions containing cyclodextrins - Google Patents
Antiviral pharmaceutical compositions containing cyclodextrins Download PDFInfo
- Publication number
- PH26159A PH26159A PH37160A PH37160A PH26159A PH 26159 A PH26159 A PH 26159A PH 37160 A PH37160 A PH 37160A PH 37160 A PH37160 A PH 37160A PH 26159 A PH26159 A PH 26159A
- Authority
- PH
- Philippines
- Prior art keywords
- alkyl
- aryl
- composition according
- hydrogen
- phenyl
- Prior art date
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- 229920000858 Cyclodextrin Polymers 0.000 title claims description 51
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 230000000840 anti-viral effect Effects 0.000 title claims description 9
- 229940097362 cyclodextrins Drugs 0.000 title description 13
- -1 hydroxy, mercapto, amino Chemical group 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000003443 antiviral agent Substances 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound 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 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000007921 spray Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 208000036142 Viral infection Diseases 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical class C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 3
- 125000001033 ether group Chemical group 0.000 claims 3
- DVOVBGJJSFSOPZ-UHFFFAOYSA-N 2-acetamidopropanamide Chemical compound NC(=O)C(C)NC(C)=O DVOVBGJJSFSOPZ-UHFFFAOYSA-N 0.000 claims 1
- UHOVUWJBKPGIPO-UHFFFAOYSA-N 3-methoxy-6-[4-(3-methylphenyl)-3,6-dihydro-2h-pyridin-1-yl]pyridazine Chemical group N1=NC(OC)=CC=C1N1CC=C(C=2C=C(C)C=CC=2)CC1 UHOVUWJBKPGIPO-UHFFFAOYSA-N 0.000 claims 1
- 101100102516 Clonostachys rogersoniana vern gene Proteins 0.000 claims 1
- 101100386623 Mus musculus Amd2 gene Proteins 0.000 claims 1
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 claims 1
- 125000005638 hydrazono group Chemical group 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 description 35
- 229940079593 drug Drugs 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
- 239000012153 distilled water Substances 0.000 description 17
- 239000000902 placebo Substances 0.000 description 17
- 229940068196 placebo Drugs 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- 241000700605 Viruses Species 0.000 description 14
- 208000015181 infectious disease Diseases 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 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 description 9
- 125000002947 alkylene group Chemical group 0.000 description 8
- 241000709661 Enterovirus Species 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229940052303 ethers for general anesthesia Drugs 0.000 description 7
- 230000028327 secretion Effects 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- MMOTUYBUAZJWRU-UHFFFAOYSA-N 1-(5-tetradecoxyfuran-2-yl)ethanone Chemical compound CCCCCCCCCCCCCCOC1=CC=C(C(C)=O)O1 MMOTUYBUAZJWRU-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 201000009240 nasopharyngitis Diseases 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- IWKXBHQELWQLHF-CAPFRKAQSA-N (ne)-n-[(2-amino-3-propan-2-ylsulfonylbenzimidazol-5-yl)-phenylmethylidene]hydroxylamine Chemical compound C1=C2N(S(=O)(=O)C(C)C)C(N)=NC2=CC=C1C(=N\O)\C1=CC=CC=C1 IWKXBHQELWQLHF-CAPFRKAQSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- QQFJUDMWXYKXFF-UHFFFAOYSA-N acetic acid;mercury Chemical compound [Hg].CC(O)=O QQFJUDMWXYKXFF-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 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 3
- 239000002585 base Substances 0.000 description 3
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- 238000003255 drug test Methods 0.000 description 3
- 229950008161 enviroxime Drugs 0.000 description 3
- 230000002489 hematologic effect Effects 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
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- 241000894007 species Species 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- YNJFYAVGJCAZGH-UHFFFAOYSA-N 2,3-dichloro-2-phenyl-3,4-dihydrochromene Chemical compound ClC1CC2=CC=CC=C2OC1(Cl)C1=CC=CC=C1 YNJFYAVGJCAZGH-UHFFFAOYSA-N 0.000 description 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 2
- GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 2
- ZFEMBLOGBQVWKR-UHFFFAOYSA-N 3-chloro-6-[4-(3-methylphenyl)-3,6-dihydro-2h-pyridin-1-yl]pyridazine Chemical compound CC1=CC=CC(C=2CCN(CC=2)C=2N=NC(Cl)=CC=2)=C1 ZFEMBLOGBQVWKR-UHFFFAOYSA-N 0.000 description 2
- DDOAUTHWSCUHQA-UHFFFAOYSA-N 3-methoxy-6-[4-(3-methylphenyl)-1-piperazinyl]pyridazine Chemical compound N1=NC(OC)=CC=C1N1CCN(C=2C=C(C)C=CC=2)CC1 DDOAUTHWSCUHQA-UHFFFAOYSA-N 0.000 description 2
- BFPYUXIFGJJYHU-AYSLTRBKSA-N 6-[(e)-1-phenylprop-1-enyl]-1-propan-2-ylsulfonylbenzimidazol-2-amine Chemical compound C=1C=C2N=C(N)N(S(=O)(=O)C(C)C)C2=CC=1C(=C/C)/C1=CC=CC=C1 BFPYUXIFGJJYHU-AYSLTRBKSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000709664 Picornaviridae Species 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 229940121357 antivirals Drugs 0.000 description 2
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- KDQPSPMLNJTZAL-UHFFFAOYSA-L disodium hydrogenphosphate dihydrate Chemical compound O.O.[Na+].[Na+].OP([O-])([O-])=O KDQPSPMLNJTZAL-UHFFFAOYSA-L 0.000 description 2
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- 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 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
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- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
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- 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
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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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Nanotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- Organic Chemistry (AREA)
- Medical Informatics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6851287A | 1987-07-01 | 1987-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26159A true PH26159A (en) | 1992-03-18 |
Family
ID=22083057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH37160A PH26159A (en) | 1987-07-01 | 1988-07-01 | Antiviral pharmaceutical compositions containing cyclodextrins |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4956351A (pt) |
| EP (1) | EP0300526A3 (pt) |
| JP (1) | JPS6445319A (pt) |
| KR (1) | KR890001554A (pt) |
| AU (1) | AU611692B2 (pt) |
| CA (1) | CA1322172C (pt) |
| DK (1) | DK360988A (pt) |
| FI (1) | FI883136A (pt) |
| HU (1) | HU204705B (pt) |
| IL (1) | IL86910A0 (pt) |
| NO (1) | NO882926L (pt) |
| NZ (1) | NZ225045A (pt) |
| PH (1) | PH26159A (pt) |
| PT (1) | PT87880A (pt) |
| RU (1) | RU2016567C1 (pt) |
| ZA (1) | ZA884747B (pt) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5001125A (en) * | 1984-03-26 | 1991-03-19 | Janssen Pharmaceutica N.V. | Anti-virally active pyridazinamines |
| EP0491812A4 (en) * | 1989-09-14 | 1992-11-04 | Australian Commercial Research & Development Limited | Drug delivery compositions |
| JO1645B1 (en) * | 1989-12-26 | 1991-11-27 | شركة جانسين فارماسوتيكا ان. في | Pyridazine compounds are antibacterial viruses |
| GB9012663D0 (en) * | 1990-06-07 | 1990-08-01 | Erba Carlo Spa | Galenic formulations containing cyclodextrins |
| IL100856A (en) * | 1991-02-15 | 1998-03-10 | Janssen Pharmaceutica Nv | History of carboxyl (alkyloxyalkyl of cyclodextrins, their preparation and pharmaceutical preparations containing them |
| US5221669A (en) * | 1991-04-19 | 1993-06-22 | The United States Of America As Represented By The Department Of Health And Human Services | Antiviral compositions containing α-cyclodextrin sulfates alone and in combination with other known antiviral agents and glucocorticoids and methods of treating viral infections |
| US5321014A (en) * | 1991-06-28 | 1994-06-14 | The United States Of America As Represented By The Department Of Health And Human Services | Molecular encapsulation and delivery of alkenes alkynes and long chain alkanes, to living mammalian cells |
| US5254541A (en) * | 1991-11-15 | 1993-10-19 | Merck Frosst Canada, Inc. | (Quinolin-2-ylmethoxy)indole/cyclodextrin complex |
| DE4204315A1 (de) * | 1992-02-13 | 1993-08-19 | Consortium Elektrochem Ind | Cyclodextringlycoside und verfahren zu ihrer herstellung |
| EP0674528A4 (en) * | 1992-12-02 | 1996-06-26 | Insite Vision Inc | DRUG DELIVERY SYSTEM BASED ON CYCLODEXTRIN AND A POLYMER. |
| JP2787539B2 (ja) * | 1993-02-26 | 1998-08-20 | 松森 昭 | ウイルス性疾患の予防または治療剤 |
| DE4333598A1 (de) * | 1993-10-01 | 1995-04-06 | Consortium Elektrochem Ind | Verfahren zur Herstellung von alkylierten Cyclodextrin-Derivaten, nach dem Verfahren herstellbare methylierte Cyclodextrin-Derivate und die Verwendung der Produkte |
| EP0709099A3 (en) | 1994-09-28 | 1996-07-24 | Senju Pharma Co | Aqueous suspension for nasal administration containing cyclodextrin |
| DE69733664T3 (de) | 1996-04-19 | 2011-04-14 | Grifols Inc. (n.d. Ges.d.Staates Delaware), Los Angeles | Verfahren zur INaktivierung von Viren und Lyophilisierung von Blutproteinen |
| GB9711643D0 (en) * | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| US6683100B2 (en) | 1999-01-19 | 2004-01-27 | Novartis Ag | Organic compounds |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| AUPQ105499A0 (en) | 1999-06-18 | 1999-07-08 | Biota Scientific Management Pty Ltd | Antiviral agents |
| US6479467B1 (en) | 1999-12-16 | 2002-11-12 | Eastman Chemical Company | Cyclodextrin ethers |
| AUPR213700A0 (en) * | 2000-12-18 | 2001-01-25 | Biota Scientific Management Pty Ltd | Antiviral agents |
| US20020146409A1 (en) * | 2001-01-30 | 2002-10-10 | Herring Steven W. | Methods for stabilizing lyophilized blood proteins |
| DE10203999A1 (de) * | 2002-02-01 | 2003-08-14 | Nutricia Nv | Cycloglycane |
| AU2003215027A1 (en) * | 2002-03-21 | 2003-10-08 | Regents Of The University Of Minnesota | Cyclodextrin compositions and methods of treating viral infections |
| WO2004078115A2 (en) * | 2003-02-28 | 2004-09-16 | Viropharma, Incorporated | Benzothiazole compounds, compositions and methods for treatment and prophylaxis of rotavirus infections and associated diseases |
| CN101083982A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 用于治疗硬脂酰CoA去饱和酶介导的疾病的杂环衍生物 |
| TW200626154A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| CN101084207A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶抑制剂的用途 |
| TW200626155A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| AU2005329423A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| BRPI0515478A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seu uso como mediadores de estearoil-coa-desaturase |
| WO2006034279A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| PL1888548T3 (pl) | 2005-05-26 | 2013-01-31 | Neuron Systems Inc | Pochodna chinoliny do leczenia schorzeń siatkówki |
| BRPI0611187A2 (pt) | 2005-06-03 | 2010-08-24 | Xenon Pharmaceuticals Inc | derivados aminotiazàis como inibidores da estearoil-coa desaturase humana |
| US8158609B1 (en) * | 2006-11-02 | 2012-04-17 | Novartis Ag | Use of cyclodextrins as an active ingredient for treating dry AMD and solubilizing drusen |
| CA2782015C (en) | 2009-12-11 | 2020-08-25 | Neuron Systems, Inc. | Topical ophthalmic compositions and methods for the treatment of macular degeneration |
| RU2448120C1 (ru) * | 2010-11-01 | 2012-04-20 | Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания "Медбиофарм" | Клатратные комплексы бета-циклодекстрина с 1-{[6-бром-1-метил-5-метокси-2-фенилтиометил-1-н-индол-3-ил]карбонил}-4-бензилпиперазином, обладающие противовирусной активностью, их получение и применение |
| RU2451680C1 (ru) | 2011-02-21 | 2012-05-27 | Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания "Медбиофарм" | Клатратный комплекс циклодекстрина или арабиногалактана с 9-фенил-симм-октагидроселеноксантеном, способ его получения (варианты), фармацевтическая композиция и лекарственное средство |
| RU2464042C1 (ru) * | 2011-03-31 | 2012-10-20 | Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания "Медбиофарм" | 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 |
| KR102435676B1 (ko) | 2013-01-23 | 2022-08-24 | 알데이라 테라퓨틱스, 아이엔씨. | 독성 알데히드 관련된 질병 및 치료 |
| BR112018003250A2 (pt) | 2015-08-21 | 2018-09-25 | Aldeyra Therapeutics Inc | compostos deuterados e usos dos mesmos |
| MX2018010292A (es) | 2016-02-28 | 2018-09-27 | Aldeyra Therapeutics Inc | Tratamiento de condiciones oculares alergicas con ciclodextrinas. |
| AU2017264697A1 (en) | 2016-05-09 | 2018-11-22 | Aldeyra Therapeutics, Inc. | Combination treatment of ocular inflammatory disorders and diseases |
| WO2018170476A1 (en) | 2017-03-16 | 2018-09-20 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| CA3077362A1 (en) | 2017-10-10 | 2019-04-18 | Aldeyra Therapeutics, Inc. | Treatment of inflammatory disorders |
| US12006298B2 (en) | 2018-08-06 | 2024-06-11 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| JP7505786B2 (ja) | 2018-09-25 | 2024-06-25 | アルデイラ セラピューティクス， インコーポレイテッド | ドライアイ疾患を処置するための製剤 |
| WO2020198064A1 (en) | 2019-03-26 | 2020-10-01 | Aldeyra Therapeutics, Inc. | Ophthalmic formulations and uses thereof |
| US12098132B2 (en) | 2019-05-02 | 2024-09-24 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
| CA3137301A1 (en) | 2019-05-02 | 2020-11-05 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| EP4149470A4 (en) | 2020-05-13 | 2024-04-24 | Aldeyra Therapeutics, Inc. | PHARMACEUTICAL FORMULATIONS AND USES THEREOF |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR64915B (en) * | 1978-09-14 | 1980-06-09 | Janssen Pharmaceutica Nv | Improved etomidate-containing compositions |
| HU194858B (en) * | 1982-12-03 | 1988-03-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing dibenzo/b,d/pirane derivatives and pharmaceutical compositions containing them |
| DE3346123A1 (de) * | 1983-12-21 | 1985-06-27 | Janssen Pharmaceutica, N.V., Beerse | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung |
| IT1196033B (it) * | 1984-02-22 | 1988-11-10 | Chiesi Farma Spa | Composto ad attivita' antiinfiammatoria ottenuto per complessazione con beta-ciclodestrina e relative formulazioni farmaceutiche |
| US5001125A (en) * | 1984-03-26 | 1991-03-19 | Janssen Pharmaceutica N.V. | Anti-virally active pyridazinamines |
| US4727064A (en) * | 1984-04-25 | 1988-02-23 | The United States Of America As Represented By The Department Of Health And Human Services | Pharmaceutical preparations containing cyclodextrin derivatives |
| GB8506792D0 (en) * | 1985-03-15 | 1985-04-17 | Janssen Pharmaceutica Nv | Derivatives of y-cyclodextrin |
| GB8613688D0 (en) * | 1986-06-05 | 1986-07-09 | Euro Celtique Sa | Pharmaceutical composition |
-
1988
- 1988-06-15 NZ NZ225045A patent/NZ225045A/xx unknown
- 1988-06-22 EP EP88201288A patent/EP0300526A3/en not_active Ceased
- 1988-06-23 US US07/210,677 patent/US4956351A/en not_active Expired - Fee Related
- 1988-06-24 AU AU18352/88A patent/AU611692B2/en not_active Ceased
- 1988-06-29 IL IL86910A patent/IL86910A0/xx unknown
- 1988-06-29 KR KR1019880007902A patent/KR890001554A/ko not_active Application Discontinuation
- 1988-06-30 HU HU883383A patent/HU204705B/hu not_active IP Right Cessation
- 1988-06-30 NO NO88882926A patent/NO882926L/no unknown
- 1988-06-30 CA CA000570955A patent/CA1322172C/en not_active Expired - Fee Related
- 1988-06-30 DK DK360988A patent/DK360988A/da not_active Application Discontinuation
- 1988-06-30 PT PT87880A patent/PT87880A/pt not_active Application Discontinuation
- 1988-06-30 FI FI883136A patent/FI883136A/fi not_active Application Discontinuation
- 1988-06-30 RU SU884356120A patent/RU2016567C1/ru active
- 1988-07-01 PH PH37160A patent/PH26159A/en unknown
- 1988-07-01 ZA ZA884747A patent/ZA884747B/xx unknown
- 1988-07-01 JP JP63162733A patent/JPS6445319A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU1835288A (en) | 1989-01-05 |
| US4956351A (en) | 1990-09-11 |
| DK360988A (da) | 1989-01-02 |
| NZ225045A (en) | 1990-06-26 |
| CA1322172C (en) | 1993-09-14 |
| HU204705B (en) | 1992-02-28 |
| IL86910A0 (en) | 1988-11-30 |
| ZA884747B (en) | 1990-03-28 |
| PT87880A (pt) | 1989-06-30 |
| FI883136A (fi) | 1989-01-02 |
| EP0300526A3 (en) | 1989-04-12 |
| FI883136A0 (fi) | 1988-06-30 |
| AU611692B2 (en) | 1991-06-20 |
| HUT47433A (en) | 1989-03-28 |
| JPS6445319A (en) | 1989-02-17 |
| NO882926L (no) | 1989-01-02 |
| NO882926D0 (no) | 1988-06-30 |
| DK360988D0 (da) | 1988-06-30 |
| EP0300526A2 (en) | 1989-01-25 |
| RU2016567C1 (ru) | 1994-07-30 |
| KR890001554A (ko) | 1989-03-27 |
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