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
Links
- 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
- 238000002512 chemotherapy Methods 0.000 description 3
- 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
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 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
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 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
- 238000010876 biochemical test Methods 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229960002303 citric acid monohydrate Drugs 0.000 description 2
- KDQPSPMLNJTZAL-UHFFFAOYSA-L disodium hydrogenphosphate dihydrate Chemical compound O.O.[Na+].[Na+].OP([O-])([O-])=O KDQPSPMLNJTZAL-UHFFFAOYSA-L 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 210000001508 eye Anatomy 0.000 description 2
- 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
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002545 isoxazoles Chemical class 0.000 description 2
- ODLHGICHYURWBS-FOSILIAISA-N molport-023-220-444 Chemical compound CC(O)COC[C@@H]([C@@H]([C@H]([C@@H]1O)O)O[C@@H]2O[C@H]([C@H](O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O3)[C@@H](O)[C@@H]2O)COCC(O)C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@H]3O[C@H]1COCC(C)O ODLHGICHYURWBS-FOSILIAISA-N 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229940067107 phenylethyl alcohol Drugs 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- KGFYDIZALLKOLQ-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one Chemical compound C1=CC(OC)=CC=C1CCC(=O)C1=C(O)C=C(OC)C=C1OC KGFYDIZALLKOLQ-UHFFFAOYSA-N 0.000 description 1
- JZKLXGZEUJUGIK-UHFFFAOYSA-N 2,3-dimethoxy-1,3-diphenylprop-2-en-1-one Chemical compound COC(=C(C1=CC=CC=C1)OC)C(=O)C1=CC=CC=C1 JZKLXGZEUJUGIK-UHFFFAOYSA-N 0.000 description 1
- QAYKDRUKUZJJSO-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile Chemical compound N#CC1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C(Cl)=C1 QAYKDRUKUZJJSO-UHFFFAOYSA-N 0.000 description 1
- ZGZXPGYGYRATEU-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1OC2=NC=CC=C2CC1 ZGZXPGYGYRATEU-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- OSQHNVJNVMDXCO-UHFFFAOYSA-N 2-[4-[(2,5-dimethylphenyl)methyl]piperazin-1-yl]-1,3-thiazole-4-carboxylic acid Chemical compound CC1=CC=C(C)C(CN2CCN(CC2)C=2SC=C(N=2)C(O)=O)=C1 OSQHNVJNVMDXCO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- JOAQSTREZQPHLS-UHFFFAOYSA-N 2-methyl-5-pyridin-2-yl-1h-benzimidazol-4-amine Chemical class NC1=C2NC(C)=NC2=CC=C1C1=CC=CC=N1 JOAQSTREZQPHLS-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- WNJWHEQEMFRZMT-UHFFFAOYSA-N 2-piperazin-1-yl-1,3-thiazole-4-carboxylic acid Chemical class OC(=O)C1=CSC(N2CCNCC2)=N1 WNJWHEQEMFRZMT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AWXFHJXPYIPUSS-UHFFFAOYSA-N 3,5,6-trimethoxy-2-phenylchromen-4-one Chemical compound COC=1C(=O)C2=C(OC)C(OC)=CC=C2OC=1C1=CC=CC=C1 AWXFHJXPYIPUSS-UHFFFAOYSA-N 0.000 description 1
- YUSMIUGOOGKMJN-UHFFFAOYSA-N 3,7-dimethoxy-2-(3-methoxyphenyl)chromen-4-one Chemical compound COC1=CC=CC(C2=C(C(=O)C3=CC=C(OC)C=C3O2)OC)=C1 YUSMIUGOOGKMJN-UHFFFAOYSA-N 0.000 description 1
- VEEKGKCCJDLMIG-UHFFFAOYSA-N 3-bromo-6-[4-(3-methylphenyl)piperazin-1-yl]pyridazine Chemical compound CC1=CC=CC(N2CCN(CC2)C=2N=NC(Br)=CC=2)=C1 VEEKGKCCJDLMIG-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- HEXCDWWIZFBJKV-UHFFFAOYSA-N 3-chloro-6-[3-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl]pyridazine Chemical compound FC(F)(F)C1=CC=CC(C2CN(CC2)C=2N=NC(Cl)=CC=2)=C1 HEXCDWWIZFBJKV-UHFFFAOYSA-N 0.000 description 1
- GJOWSEBTWQNKPC-UHFFFAOYSA-N 3-methyloxiran-2-ol Chemical compound CC1OC1O GJOWSEBTWQNKPC-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- HJSRRIKDASQDOU-UHFFFAOYSA-N 4-ethoxy-2-hydroxy-6-methoxy-n-[(4-methoxyphenyl)methyl]benzamide Chemical compound COC1=CC(OCC)=CC(O)=C1C(=O)NCC1=CC=C(OC)C=C1 HJSRRIKDASQDOU-UHFFFAOYSA-N 0.000 description 1
- GQRHSQRSXKECSK-UHFFFAOYSA-N 5-[3-[2-bromo-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]phenyl]-3-methyl-1,2-oxazole Chemical compound O1N=C(C)C=C1C1=CC=CC(OC=2C(=CC(=CC=2)C=2OCCN=2)Br)=C1 GQRHSQRSXKECSK-UHFFFAOYSA-N 0.000 description 1
- XUAMGNGLPVFBMF-UHFFFAOYSA-N 5-[5-(2,6-dichloro-4-pyridin-2-ylphenoxy)pentyl]-3-methyl-1,2-oxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=C(Cl)C=C(C=2N=CC=CC=2)C=C1Cl XUAMGNGLPVFBMF-UHFFFAOYSA-N 0.000 description 1
- CCSNBWHEWTVRHT-UHFFFAOYSA-N 5-[5-[2,6-dichloro-4-(furan-2-yl)phenoxy]pentyl]-3-methyl-1,2-oxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=C(Cl)C=C(C=2OC=CC=2)C=C1Cl CCSNBWHEWTVRHT-UHFFFAOYSA-N 0.000 description 1
- WDNAQQJUMPVRGM-UHFFFAOYSA-N 6-chloro-2-(4-chlorophenyl)-3,4-dihydro-2h-chromene Chemical compound C1=CC(Cl)=CC=C1C1OC2=CC=C(Cl)C=C2CC1 WDNAQQJUMPVRGM-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000428352 Amma Species 0.000 description 1
- 241000537222 Betabaculovirus Species 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- TVDRZXOSMBTIKU-NSCUHMNNSA-N C\C=C\C1=CC=C2NC=NC2=C1 Chemical class C\C=C\C1=CC=C2NC=NC2=C1 TVDRZXOSMBTIKU-NSCUHMNNSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000711573 Coronaviridae Species 0.000 description 1
- WHGYBXFWUBPSRW-UHFFFAOYSA-N Cycloheptaamylose Natural products O1C(C(C2O)O)C(CO)OC2OC(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 WHGYBXFWUBPSRW-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000353621 Eilat virus Species 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000187656 Eucalyptus cornuta Species 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 241000023320 Luma <angiosperm> Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000702670 Rotavirus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 229930092411 Swietenocoumarin D Natural products 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000002128 anti-rhinoviral effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000546 chi-square test Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 230000000797 effect on infection Effects 0.000 description 1
- 229950000529 enviradene Drugs 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- JACFWUYASCKTOW-UHFFFAOYSA-N n-(1h-benzimidazol-2-ylmethyl)pyridin-4-amine Chemical class N=1C2=CC=CC=C2NC=1CNC1=CC=NC=C1 JACFWUYASCKTOW-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- 230000037125 natural defense Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229960003857 proglumide Drugs 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Nanotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (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 (fr) |
EP (1) | EP0300526A3 (fr) |
JP (1) | JPS6445319A (fr) |
KR (1) | KR890001554A (fr) |
AU (1) | AU611692B2 (fr) |
CA (1) | CA1322172C (fr) |
DK (1) | DK360988A (fr) |
FI (1) | FI883136A (fr) |
HU (1) | HU204705B (fr) |
IL (1) | IL86910A0 (fr) |
NO (1) | NO882926L (fr) |
NZ (1) | NZ225045A (fr) |
PH (1) | PH26159A (fr) |
PT (1) | PT87880A (fr) |
RU (1) | RU2016567C1 (fr) |
ZA (1) | ZA884747B (fr) |
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 |
JPH08503951A (ja) * | 1992-12-02 | 1996-04-30 | インサイト・ビジョン・インコーポレイテッド | シクロデキストリンとポリマーを用いた薬剤供給系 |
US5605919A (en) * | 1993-02-26 | 1997-02-25 | Takeda Chemical Industries, Ltd. | Treatment for viral diseases |
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 (fr) | 1994-09-28 | 1996-07-24 | Senju Pharma Co | Suspension aqueuse nasale comprenant cyclodextrine |
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 |
WO2003080080A1 (fr) * | 2002-03-21 | 2003-10-02 | Regents Of The University Of Minnesota | Compositions de cyclodextrine et methodes de traitement d'infections virales |
WO2004078115A2 (fr) * | 2003-02-28 | 2004-09-16 | Viropharma, Incorporated | Composes de benzothiazole, compositions et procedes pour le traitement et la prophylaxie des infections par rotavirus et des maladies associees |
WO2006034341A2 (fr) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Derives heterocycliques et leur utilisation en tant qu'agents therapeutiques |
US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
CA2580787A1 (fr) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Derives heterocycliques et utilisation de ceux-ci comme agents therapeutiques |
US7592343B2 (en) | 2004-09-20 | 2009-09-22 | Xenon Pharmaceuticals Inc. | Pyridazine-piperazine compounds and their use as stearoyl-CoA desaturase inhibitors |
JP4958786B2 (ja) | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 複素環誘導体および治療薬としてのそれらの使用 |
BRPI0515488A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados de heterocìclicos e seu uso como agentes terapêuticos |
EP1799668A1 (fr) | 2004-09-20 | 2007-06-27 | Xenon Pharmaceuticals Inc. | Derives heterocycliques et leur utilisation en tant que modulateurs de stearoyle-coa desaturase |
EP2336117A1 (fr) | 2005-05-26 | 2011-06-22 | Neuron Systems, Inc | Composés hétérocycliques pour le traitement des maladies rétiniennes |
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 (fr) | 2009-12-11 | 2020-08-25 | Neuron Systems, Inc. | Compositions ophthalmiques topiques et methodes de traitement de la degenerescence maculaire |
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 |
SG11201505587YA (en) | 2013-01-23 | 2015-08-28 | Aldeyra Therapeutics Inc | Toxic aldehyde related diseases and treatment |
EP4400106A1 (fr) | 2015-08-21 | 2024-07-17 | Aldeyra Therapeutics, Inc. | Composés deutérés et leurs utilisations |
AU2017224249A1 (en) | 2016-02-28 | 2018-09-13 | Aldeyra Therapeutics, Inc. | Treatment of allergic eye conditions with cyclodextrins |
US11129823B2 (en) | 2016-05-09 | 2021-09-28 | Aldeyra Therapeutics, Inc. | Combination treatment of ocular inflammatory disorders and diseases |
ES2968462T3 (es) | 2017-03-16 | 2024-05-09 | Aldeyra Therapeutics Inc | Sal polimórfica de 6-cloro-3-amino-2(2-hidroxiprolil) quinolina y usos de la misma |
US11040039B2 (en) | 2017-10-10 | 2021-06-22 | Aldeyra Therapeutics, Inc. | Treatment of inflammatory disorders |
EP3833660A4 (fr) | 2018-08-06 | 2022-05-11 | Aldeyra Therapeutics, Inc. | Composés polymorphes et leurs utilisations |
EP3856478A4 (fr) | 2018-09-25 | 2022-06-08 | Aldeyra Therapeutics, Inc. | Formulations pour le traitement de la maladie de l'oeil sec |
JP2022526917A (ja) | 2019-03-26 | 2022-05-27 | アルデイラ セラピューティクス, インコーポレイテッド | 眼科用製剤およびその使用 |
US12098132B2 (en) | 2019-05-02 | 2024-09-24 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
JP2022530967A (ja) | 2019-05-02 | 2022-07-05 | アルデイラ セラピューティクス, インコーポレイテッド | 多形化合物およびその使用 |
JP2023526016A (ja) | 2020-05-13 | 2023-06-20 | アルデイラ セラピューティクス, インコーポレイテッド | 医薬製剤およびその使用 |
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/fr 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 KR KR1019880007902A patent/KR890001554A/ko not_active Application Discontinuation
- 1988-06-29 IL IL86910A patent/IL86910A0/xx unknown
- 1988-06-30 NO NO88882926A patent/NO882926L/no unknown
- 1988-06-30 RU SU884356120A patent/RU2016567C1/ru active
- 1988-06-30 FI FI883136A patent/FI883136A/fi not_active Application Discontinuation
- 1988-06-30 CA CA000570955A patent/CA1322172C/fr not_active Expired - Fee Related
- 1988-06-30 PT PT87880A patent/PT87880A/pt not_active Application Discontinuation
- 1988-06-30 DK DK360988A patent/DK360988A/da not_active Application Discontinuation
- 1988-06-30 HU HU883383A patent/HU204705B/hu not_active IP Right Cessation
- 1988-07-01 ZA ZA884747A patent/ZA884747B/xx unknown
- 1988-07-01 PH PH37160A patent/PH26159A/en unknown
- 1988-07-01 JP JP63162733A patent/JPS6445319A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
HUT47433A (en) | 1989-03-28 |
RU2016567C1 (ru) | 1994-07-30 |
DK360988A (da) | 1989-01-02 |
EP0300526A2 (fr) | 1989-01-25 |
FI883136A (fi) | 1989-01-02 |
AU611692B2 (en) | 1991-06-20 |
NZ225045A (en) | 1990-06-26 |
EP0300526A3 (fr) | 1989-04-12 |
PT87880A (pt) | 1989-06-30 |
DK360988D0 (da) | 1988-06-30 |
HU204705B (en) | 1992-02-28 |
AU1835288A (en) | 1989-01-05 |
CA1322172C (fr) | 1993-09-14 |
NO882926D0 (no) | 1988-06-30 |
ZA884747B (en) | 1990-03-28 |
IL86910A0 (en) | 1988-11-30 |
KR890001554A (ko) | 1989-03-27 |
JPS6445319A (en) | 1989-02-17 |
NO882926L (no) | 1989-01-02 |
US4956351A (en) | 1990-09-11 |
FI883136A0 (fi) | 1988-06-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
PH26159A (en) | Antiviral pharmaceutical compositions containing cyclodextrins | |
EP2402008B1 (fr) | Formulations contenant de l'amiodarone et de la cyclodextrine d'éther de sulfoalkyle | |
KR101689924B1 (ko) | 고농도 올로파타딘 안과용 조성물 | |
EP0472327B1 (fr) | Composition de gouttes pour les yeux | |
CZ283693A3 (en) | Antiallergic preparations for use in ophthalmology and otorhinology | |
US20090291913A1 (en) | FACTOR Xa INHIBITOR FORMULATION AND METHOD | |
US20060193783A1 (en) | Low dose corticosteroid composition | |
JPH04275222A (ja) | 安定性を強化したピロキシカム溶液、およびその製造方法 | |
EP0345926B1 (fr) | Compositions pharmaceutiques contenant de la pentamidine | |
US5886018A (en) | Pharmaceutical composition for parenteral administration containing an indole-carboxylic acid | |
MXPA05005587A (es) | Composicion liquida concentrada de valdecoxib. | |
EP0383680B1 (fr) | Solutions de la pentamidine | |
WO1993023032A1 (fr) | Remede contre la cataracte et procede de production associe | |
JP2013510172A (ja) | 置換ガンマラクタムを含有する眼科用製剤およびその使用法 | |
JP2022530657A (ja) | シュレム管を標的とするTie-2活性化物質 | |
JPH10152438A (ja) | 1−アザキサントン誘導体またはその塩の安定化方法および1−アザキサントン誘導体含有組成物 | |
AU2005291307B2 (en) | Pulmonary administration of an antithrombotic compound | |
JP3122163B2 (ja) | シクロデキストリン複合体 | |
JP2000256186A (ja) | 咽頭疾患用組成物 | |
JPH05124963A (ja) | テオフイリン含有液剤 | |
CA2161980A1 (fr) | Derives de substitution de methylenedioxy¬3',4':6,7|indolizino-¬1,2-b|quinolinones | |
JP2000186042A (ja) | ラクトン誘導体を用いる炎症性呼吸器疾患治療剤 | |
US20230073803A1 (en) | Pharmaceutical composition of cyclooxygenase - 2 inhibitors | |
ZA200506549B (en) | A low dose corticosteroid composition |