SK75698A3 - Phospholipid derivatives of phosphono-carboxylic acids, the production of said derivatives and the use of said derivatives as antiviral medicaments - Google Patents
Phospholipid derivatives of phosphono-carboxylic acids, the production of said derivatives and the use of said derivatives as antiviral medicaments Download PDFInfo
- Publication number
- SK75698A3 SK75698A3 SK756-98A SK75698A SK75698A3 SK 75698 A3 SK75698 A3 SK 75698A3 SK 75698 A SK75698 A SK 75698A SK 75698 A3 SK75698 A3 SK 75698A3
- Authority
- SK
- Slovakia
- Prior art keywords
- acid
- formula
- compounds
- derivatives
- decyloxy
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 Phospholipid derivatives of phosphono-carboxylic acids Chemical class 0.000 title abstract description 83
- 230000000840 anti-viral effect Effects 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 150000007530 organic bases Chemical class 0.000 claims abstract description 4
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 46
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical class OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 8
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 229960004203 carnitine Drugs 0.000 claims description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 3
- 229960001231 choline Drugs 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229940031098 ethanolamine Drugs 0.000 claims description 3
- 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 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 210000000987 immune system Anatomy 0.000 claims description 2
- 230000001177 retroviral effect Effects 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 abstract description 5
- 239000000651 prodrug Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 3
- 210000004027 cell Anatomy 0.000 description 28
- 239000013543 active substance Substances 0.000 description 20
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 18
- 229960005102 foscarnet Drugs 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 239000000126 substance Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001727 in vivo Methods 0.000 description 9
- 239000002777 nucleoside Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 241000700605 Viruses Species 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 8
- 230000001225 therapeutic effect Effects 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 208000030507 AIDS Diseases 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000003835 nucleoside group Chemical group 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- 241001430294 unidentified retrovirus Species 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 206010001513 AIDS related complex Diseases 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 210000003714 granulocyte Anatomy 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000002502 liposome Substances 0.000 description 4
- 210000002540 macrophage Anatomy 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229960004679 doxorubicin Drugs 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 210000000265 leukocyte Anatomy 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 210000004698 lymphocyte Anatomy 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 210000001616 monocyte Anatomy 0.000 description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 description 2
- OGLYJYLEWCMZEI-UHFFFAOYSA-N 1-(3-dodecylsulfanyldecan-2-yloxy)propan-1-ol Chemical compound CCCCCCCCCCCCSC(C(C)OC(O)CC)CCCCCCC OGLYJYLEWCMZEI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- QOIQRLULIZSOFX-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC QOIQRLULIZSOFX-UHFFFAOYSA-N 0.000 description 2
- IFOOASKUGQQZPA-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC IFOOASKUGQQZPA-UHFFFAOYSA-N 0.000 description 2
- NJLHHACGWKAWKL-UHFFFAOYSA-N ClP(Cl)=O Chemical class ClP(Cl)=O NJLHHACGWKAWKL-UHFFFAOYSA-N 0.000 description 2
- 206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 description 2
- 208000031886 HIV Infections Diseases 0.000 description 2
- 241000701085 Human alphaherpesvirus 3 Species 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010049025 Persistent generalised lymphadenopathy Diseases 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000798 anti-retroviral effect Effects 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 210000002798 bone marrow cell Anatomy 0.000 description 2
- 231100000366 bone marrow toxicity Toxicity 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- 208000001763 cytomegalovirus retinitis Diseases 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 239000002158 endotoxin Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 231100000283 hepatitis Toxicity 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 201000003450 persistent generalized lymphadenopathy Diseases 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 description 1
- GUXRZQZCNOHHDO-UHFFFAOYSA-N 2-phosphonopropanoic acid Chemical compound OC(=O)C(C)P(O)(O)=O GUXRZQZCNOHHDO-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 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 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010051779 Bone marrow toxicity Diseases 0.000 description 1
- RQAWTJRMFUXZQR-UHFFFAOYSA-N C(C(C)(C)C)OC(C(C(C)OC(C)C(CCCCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C(C)(C)C)OC(C(C(C)OC(C)C(CCCCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O RQAWTJRMFUXZQR-UHFFFAOYSA-N 0.000 description 1
- GMLLTGJUENLUKY-UHFFFAOYSA-N C(C(C)(C)C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)=O Chemical compound C(C(C)(C)C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)=O GMLLTGJUENLUKY-UHFFFAOYSA-N 0.000 description 1
- RRQGDQFCRGFCCV-UHFFFAOYSA-N C(C)(C)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C)(C)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O RRQGDQFCRGFCCV-UHFFFAOYSA-N 0.000 description 1
- VKEZNMHXSRGUET-UHFFFAOYSA-N C(C)(C)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C)(C)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O VKEZNMHXSRGUET-UHFFFAOYSA-N 0.000 description 1
- MVAKVNYWRNQAGR-UHFFFAOYSA-N C(C)(C)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C)(C)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCCC)(O)P(=O)OCCC)=O MVAKVNYWRNQAGR-UHFFFAOYSA-N 0.000 description 1
- YISZDNRXQODVFP-UHFFFAOYSA-N C(C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)=O Chemical compound C(C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)=O YISZDNRXQODVFP-UHFFFAOYSA-N 0.000 description 1
- PTGLVICAUXXIOD-UHFFFAOYSA-N C(C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCC)SCCCCCCCCCCC)=O Chemical compound C(C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCC)SCCCCCCCCCCC)=O PTGLVICAUXXIOD-UHFFFAOYSA-N 0.000 description 1
- PSEJXVKOAFLMFZ-UHFFFAOYSA-N C(C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCC)SCCCCCCCCCCCC)=O Chemical compound C(C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCC)SCCCCCCCCCCCC)=O PSEJXVKOAFLMFZ-UHFFFAOYSA-N 0.000 description 1
- REUGGTDJPSKETH-UHFFFAOYSA-N C(C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCCC)SCCCCCCCCCC)=O Chemical compound C(C)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCCC)SCCCCCCCCCC)=O REUGGTDJPSKETH-UHFFFAOYSA-N 0.000 description 1
- JTKGEEUEBBKHOZ-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCC)(O)P(=O)OCCC)=O JTKGEEUEBBKHOZ-UHFFFAOYSA-N 0.000 description 1
- MGQDQOCDMHNCTH-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O MGQDQOCDMHNCTH-UHFFFAOYSA-N 0.000 description 1
- ZHDUKSNDEAFRQH-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O ZHDUKSNDEAFRQH-UHFFFAOYSA-N 0.000 description 1
- POUBAHPQXJFCBA-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCCC)(O)P(=O)OCCC)=O POUBAHPQXJFCBA-UHFFFAOYSA-N 0.000 description 1
- DMYIRQLIRWROAD-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O DMYIRQLIRWROAD-UHFFFAOYSA-N 0.000 description 1
- HEJLGRMQZCBESG-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(C(C)OC(C)C(CCCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O HEJLGRMQZCBESG-UHFFFAOYSA-N 0.000 description 1
- GMFDYBKDAPTYRE-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCC)=O GMFDYBKDAPTYRE-UHFFFAOYSA-N 0.000 description 1
- GSBHNRKQWQWLFQ-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)=O GSBHNRKQWQWLFQ-UHFFFAOYSA-N 0.000 description 1
- IIPTZZFFURCGDO-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCC)SCCCCCCCCCCCCC)=O IIPTZZFFURCGDO-UHFFFAOYSA-N 0.000 description 1
- CWXDCZFTABVMSL-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCC)SCCCCCCCCCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCC)SCCCCCCCCCCC)=O CWXDCZFTABVMSL-UHFFFAOYSA-N 0.000 description 1
- DHYPMRZXZYYRFI-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCC)SCCCCCCCCCCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCC)SCCCCCCCCCCCC)=O DHYPMRZXZYYRFI-UHFFFAOYSA-N 0.000 description 1
- LHZZVESFYMZSPO-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCCC)SCCCCCCCCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(O)(P(=O)OCCC)OC(C)C(CCCCCCCCC)SCCCCCCCCCC)=O LHZZVESFYMZSPO-UHFFFAOYSA-N 0.000 description 1
- QOEQCHNOOXBYLU-UHFFFAOYSA-N C(CCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC QOEQCHNOOXBYLU-UHFFFAOYSA-N 0.000 description 1
- NXFFVYIRZUXZLH-UHFFFAOYSA-N C(CCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC Chemical compound C(CCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC NXFFVYIRZUXZLH-UHFFFAOYSA-N 0.000 description 1
- BDSHXRXWOIZQHQ-UHFFFAOYSA-N C(CCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC BDSHXRXWOIZQHQ-UHFFFAOYSA-N 0.000 description 1
- LQYDBJZRROQPFC-UHFFFAOYSA-N C(CCCCCCCCCC)S(=O)(=O)C(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC Chemical compound C(CCCCCCCCCC)S(=O)(=O)C(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC LQYDBJZRROQPFC-UHFFFAOYSA-N 0.000 description 1
- WZMVNWAYFIALIN-UHFFFAOYSA-N C(CCCCCCCCCC)S(=O)(=O)C(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC Chemical compound C(CCCCCCCCCC)S(=O)(=O)C(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC WZMVNWAYFIALIN-UHFFFAOYSA-N 0.000 description 1
- VGGXTKFEOMIAMP-UHFFFAOYSA-N C(CCCCCCCCCC)S(=O)C(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC Chemical compound C(CCCCCCCCCC)S(=O)C(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC VGGXTKFEOMIAMP-UHFFFAOYSA-N 0.000 description 1
- GHGJNIHKKNRNQJ-UHFFFAOYSA-N C(CCCCCCCCCC)S(=O)C(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC Chemical compound C(CCCCCCCCCC)S(=O)C(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC GHGJNIHKKNRNQJ-UHFFFAOYSA-N 0.000 description 1
- XCXBZZPCKLKNQG-UHFFFAOYSA-N C(CCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCC Chemical compound C(CCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCC XCXBZZPCKLKNQG-UHFFFAOYSA-N 0.000 description 1
- DEASGHUXWKWWTO-UHFFFAOYSA-N C(CCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC DEASGHUXWKWWTO-UHFFFAOYSA-N 0.000 description 1
- QZZHCKSWGNCLMC-UHFFFAOYSA-N C(CCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC Chemical compound C(CCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC QZZHCKSWGNCLMC-UHFFFAOYSA-N 0.000 description 1
- XQOZUCWKCHSVKI-UHFFFAOYSA-N C(CCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC Chemical compound C(CCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC XQOZUCWKCHSVKI-UHFFFAOYSA-N 0.000 description 1
- RJNNWHSHLVGYIH-UHFFFAOYSA-N C(CCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCC Chemical compound C(CCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCC RJNNWHSHLVGYIH-UHFFFAOYSA-N 0.000 description 1
- ANCCXSFOABTBRN-UHFFFAOYSA-N C(CCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC ANCCXSFOABTBRN-UHFFFAOYSA-N 0.000 description 1
- KIWJHRMQKUBTJV-UHFFFAOYSA-N C(CCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC Chemical compound C(CCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC KIWJHRMQKUBTJV-UHFFFAOYSA-N 0.000 description 1
- YEMAGEIHLXLLCD-UHFFFAOYSA-N C(CCCCCCCCCCC)S(=O)(=O)C(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCCC)S(=O)(=O)C(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC YEMAGEIHLXLLCD-UHFFFAOYSA-N 0.000 description 1
- CUAWDCJXESXQLN-UHFFFAOYSA-N C(CCCCCCCCCCC)S(=O)(=O)C(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCCC)S(=O)(=O)C(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC CUAWDCJXESXQLN-UHFFFAOYSA-N 0.000 description 1
- UIIWSAYBNRMPRS-UHFFFAOYSA-N C(CCCCCCCCCCC)S(=O)C(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCCC)S(=O)C(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCC UIIWSAYBNRMPRS-UHFFFAOYSA-N 0.000 description 1
- HLMNVJWVJMSIPI-UHFFFAOYSA-N C(CCCCCCCCCCC)S(=O)C(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCCC)S(=O)C(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC HLMNVJWVJMSIPI-UHFFFAOYSA-N 0.000 description 1
- ZZRUWUMHPZGQDC-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCC ZZRUWUMHPZGQDC-UHFFFAOYSA-N 0.000 description 1
- IIGRBOVHACJBQN-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCC IIGRBOVHACJBQN-UHFFFAOYSA-N 0.000 description 1
- CRQDBDZSACBJKK-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC CRQDBDZSACBJKK-UHFFFAOYSA-N 0.000 description 1
- PBJTYCZZKVXICX-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OC(C(=O)O)(O)P(=O)OCCC)CCCCCCCCC PBJTYCZZKVXICX-UHFFFAOYSA-N 0.000 description 1
- FNXILBMCXHIRJR-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OC(C(C(=O)O)(O)P(=O)OCCC)C)CCCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OC(C(C(=O)O)(O)P(=O)OCCC)C)CCCCCCC FNXILBMCXHIRJR-UHFFFAOYSA-N 0.000 description 1
- QYSSVLZELIYRRM-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCC QYSSVLZELIYRRM-UHFFFAOYSA-N 0.000 description 1
- FULLOPYXHYJLRM-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCC FULLOPYXHYJLRM-UHFFFAOYSA-N 0.000 description 1
- PYDYKFUXESCSGG-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC PYDYKFUXESCSGG-UHFFFAOYSA-N 0.000 description 1
- ORMFYLSDRLVOIS-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC Chemical compound C(CCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCCC ORMFYLSDRLVOIS-UHFFFAOYSA-N 0.000 description 1
- CLVMXXALCSRQMS-UHFFFAOYSA-N C(CCCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC Chemical compound C(CCCCCCCCCCCC)SC(C(C)OCC(C(=O)O)(O)P(=O)OCCC)CCCCCCC CLVMXXALCSRQMS-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- ZJHFHECENDCHBQ-UHFFFAOYSA-N CCCCCCOC(C(O)=O)P(O)=O Chemical compound CCCCCCOC(C(O)=O)P(O)=O ZJHFHECENDCHBQ-UHFFFAOYSA-N 0.000 description 1
- YGKLUHGQXHUENF-UHFFFAOYSA-N COC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound COC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O YGKLUHGQXHUENF-UHFFFAOYSA-N 0.000 description 1
- JOOUSLDSMNWMBE-UHFFFAOYSA-N COC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound COC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCC)(O)P(=O)OCCC)=O JOOUSLDSMNWMBE-UHFFFAOYSA-N 0.000 description 1
- LDYJNAIKQCGXPX-UHFFFAOYSA-N COC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound COC(C(C(C)OC(C)C(CCCCCCC)SCCCCCCCCCCCCC)(O)P(=O)OCCC)=O LDYJNAIKQCGXPX-UHFFFAOYSA-N 0.000 description 1
- ZRUHPPHGZUEHOU-UHFFFAOYSA-N COC(C(C(C)OC(C)C(CCCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O Chemical compound COC(C(C(C)OC(C)C(CCCCCCCC)SCCCCCCCCCCC)(O)P(=O)OCCC)=O ZRUHPPHGZUEHOU-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 102000007644 Colony-Stimulating Factors Human genes 0.000 description 1
- 108010071942 Colony-Stimulating Factors Proteins 0.000 description 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 206010011831 Cytomegalovirus infection Diseases 0.000 description 1
- 229910014570 C—OH Inorganic materials 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
- 241000450599 DNA viruses Species 0.000 description 1
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 1
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
- 208000027219 Deficiency disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 1
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 1
- 102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 description 1
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 241000714260 Human T-lymphotropic virus 1 Species 0.000 description 1
- 241000714259 Human T-lymphotropic virus 2 Species 0.000 description 1
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
- 241000701027 Human herpesvirus 6 Species 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- 102000006992 Interferon-alpha Human genes 0.000 description 1
- 108010047761 Interferon-alpha Proteins 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 102000049772 Interleukin-16 Human genes 0.000 description 1
- 101800003050 Interleukin-16 Proteins 0.000 description 1
- 102000000588 Interleukin-2 Human genes 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- 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 1
- 241000713666 Lentivirus Species 0.000 description 1
- 239000000232 Lipid Bilayer Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- GTSOBGIMTNKIPJ-UHFFFAOYSA-N OP(Cl)=O Chemical compound OP(Cl)=O GTSOBGIMTNKIPJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 1
- 241000607662 Salmonella enterica subsp. enterica serovar Abortusequi Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 102000036693 Thrombopoietin Human genes 0.000 description 1
- 108010041111 Thrombopoietin Proteins 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 208000010094 Visna Diseases 0.000 description 1
- PZQUVLQLWUVRRK-UHFFFAOYSA-L [Na+].[Na+].[Na+].[O-]P([O-])=O Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])=O PZQUVLQLWUVRRK-UHFFFAOYSA-L 0.000 description 1
- PGHOBRCXAVJNSY-UHFFFAOYSA-N [hexadecoxy(hydroxy)phosphoryl]formic acid Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)C(O)=O PGHOBRCXAVJNSY-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- ZCLSQRQRWNDNLV-UHFFFAOYSA-N acetic acid;dichloromethane;methanol Chemical compound OC.ClCCl.CC(O)=O ZCLSQRQRWNDNLV-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 229960004150 aciclovir Drugs 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 230000001925 catabolic effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 229940047120 colony stimulating factors Drugs 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- IERHLVCPSMICTF-XVFCMESISA-N cytidine 5'-monophosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O1 IERHLVCPSMICTF-XVFCMESISA-N 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000007813 immunodeficiency Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- SIGOIUCRXKUEIG-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylacetate Chemical compound COC(=O)CP(=O)(OC)OC SIGOIUCRXKUEIG-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000000771 oncological effect Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004059 squalene synthase inhibitor Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000155 toxicity by organ Toxicity 0.000 description 1
- 230000007675 toxicity by organ Effects 0.000 description 1
- BGASRLNHTSXAIR-UHFFFAOYSA-N trimethyl(trimethylsilyloxyphosphonoyloxy)silane Chemical compound C[Si](C)(C)OP(=O)O[Si](C)(C)C BGASRLNHTSXAIR-UHFFFAOYSA-N 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1995147023 DE19547023A1 (de) | 1995-12-15 | 1995-12-15 | Neue Phospholipid-Derivate von Phosphonocarbonsäuren, deren Herstellung sowie deren Verwendung als antivirale Arzneimittel |
| DE1996143416 DE19643416A1 (de) | 1996-10-22 | 1996-10-22 | Neue Phospholipid-Derivate von Phosphonocarbonsäuren, deren Herstellung sowie deren Verwendung als antivirale Arzneimittel |
| PCT/EP1996/005647 WO1997022613A1 (de) | 1995-12-15 | 1996-12-16 | Phospholipid-derivate von phosphonocarbonsäuren, deren herstellung sowie deren verwendung als antivirale arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK75698A3 true SK75698A3 (en) | 1999-03-12 |
Family
ID=26021319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK756-98A SK75698A3 (en) | 1995-12-15 | 1996-12-16 | Phospholipid derivatives of phosphono-carboxylic acids, the production of said derivatives and the use of said derivatives as antiviral medicaments |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6136797A (es) |
| EP (1) | EP0868425B1 (es) |
| JP (1) | JP2000515113A (es) |
| KR (1) | KR20000064374A (es) |
| CN (1) | CN1085672C (es) |
| AR (1) | AR005089A1 (es) |
| AT (1) | ATE278698T1 (es) |
| AU (1) | AU714236B2 (es) |
| BR (1) | BR9612133A (es) |
| CA (1) | CA2240366A1 (es) |
| CZ (1) | CZ291823B6 (es) |
| DE (1) | DE59611111D1 (es) |
| ES (1) | ES2230574T3 (es) |
| HU (1) | HUP0001534A3 (es) |
| IL (1) | IL124790A (es) |
| NO (1) | NO982754L (es) |
| NZ (1) | NZ325259A (es) |
| PL (1) | PL186402B1 (es) |
| RU (1) | RU2166508C2 (es) |
| SK (1) | SK75698A3 (es) |
| TR (1) | TR199801082T2 (es) |
| TW (1) | TW343975B (es) |
| WO (1) | WO1997022613A1 (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19547022A1 (de) * | 1995-12-15 | 1997-06-19 | Boehringer Mannheim Gmbh | Kovalente Lipid-Phosphonocarbonsäure-Konjugate, deren Herstellung sowie deren Verwendung als antivirale Arzneimittel |
| US7915238B2 (en) * | 1999-02-01 | 2011-03-29 | Eisai R & D Management Co., Ltd. | Immunomodulatory compounds and methods of use thereof |
| US20040006242A1 (en) | 1999-02-01 | 2004-01-08 | Hawkins Lynn D. | Immunomodulatory compounds and method of use thereof |
| US6551600B2 (en) * | 1999-02-01 | 2003-04-22 | Eisai Co., Ltd. | Immunological adjuvant compounds compositions and methods of use thereof |
| US6835721B2 (en) | 1999-02-01 | 2004-12-28 | Eisai Co., Ltd. | Immunomodulatory compounds and methods of use thereof |
| US6818057B2 (en) | 1999-03-02 | 2004-11-16 | Construction Research & Technology Gmbh | Retarder for calcium sulfoaluminate cements |
| US20040172288A1 (en) * | 2003-02-27 | 2004-09-02 | Korn Lawrence D. | Method for disseminating medical alert information |
| US20070292418A1 (en) * | 2005-04-26 | 2007-12-20 | Eisai Co., Ltd. | Compositions and methods for immunotherapy |
| CA2605749C (en) | 2005-04-26 | 2015-06-30 | Eisai Co., Ltd. | Compositions and methods for cancer immunotherapy |
| JP5752599B2 (ja) * | 2008-11-06 | 2015-07-22 | ヴァスキュラー バイオジェニックス リミテッド | 酸化脂質化合物およびその使用 |
| EP2876094A1 (en) | 2014-04-03 | 2015-05-27 | Basf Se | Cement and calcium sulphate based binder composition |
| KR101658048B1 (ko) | 2014-06-25 | 2016-09-20 | 한국생명공학연구원 | 포스파티딜콜린 합성경로 관여 물질을 포함하는 항바이러스용 조성물 |
| JP7465416B2 (ja) | 2018-06-26 | 2024-04-11 | ティーエスアールエル インコーポレイテッド | 代謝安定性プロドラッグ |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3164332D1 (en) * | 1980-10-21 | 1984-07-26 | Boehringer Mannheim Gmbh | Phospholipids that contain sulphur, process for their preparation and medicines containing these compounds |
| US5194654A (en) * | 1989-11-22 | 1993-03-16 | Vical, Inc. | Lipid derivatives of phosphonoacids for liposomal incorporation and method of use |
| DE3929217A1 (de) * | 1989-09-02 | 1991-03-07 | Boehringer Mannheim Gmbh | Verwendung von phospholipid-derivaten als antivirale arzneimittel und neue phospholipide |
| DE4026265A1 (de) * | 1990-08-20 | 1992-02-27 | Boehringer Mannheim Gmbh | Neue phospholipid-derivate von nucleosiden, deren herstellung sowie deren verwendung als antivirale arzneimittel |
| US5696277A (en) * | 1994-11-15 | 1997-12-09 | Karl Y. Hostetler | Antiviral prodrugs |
| DE19547022A1 (de) * | 1995-12-15 | 1997-06-19 | Boehringer Mannheim Gmbh | Kovalente Lipid-Phosphonocarbonsäure-Konjugate, deren Herstellung sowie deren Verwendung als antivirale Arzneimittel |
-
1996
- 1996-12-14 TW TW085115475A patent/TW343975B/zh active
- 1996-12-16 WO PCT/EP1996/005647 patent/WO1997022613A1/de active IP Right Grant
- 1996-12-16 EP EP96943972A patent/EP0868425B1/de not_active Expired - Lifetime
- 1996-12-16 DE DE59611111T patent/DE59611111D1/de not_active Expired - Fee Related
- 1996-12-16 SK SK756-98A patent/SK75698A3/sk unknown
- 1996-12-16 CZ CZ19981810A patent/CZ291823B6/cs not_active IP Right Cessation
- 1996-12-16 KR KR1019980704352A patent/KR20000064374A/ko not_active Application Discontinuation
- 1996-12-16 AT AT96943972T patent/ATE278698T1/de not_active IP Right Cessation
- 1996-12-16 AR ARP960105701A patent/AR005089A1/es not_active Application Discontinuation
- 1996-12-16 NZ NZ325259A patent/NZ325259A/xx unknown
- 1996-12-16 BR BR9612133A patent/BR9612133A/pt not_active IP Right Cessation
- 1996-12-16 ES ES96943972T patent/ES2230574T3/es not_active Expired - Lifetime
- 1996-12-16 JP JP09522501A patent/JP2000515113A/ja not_active Ceased
- 1996-12-16 IL IL12479096A patent/IL124790A/en not_active IP Right Cessation
- 1996-12-16 US US09/077,891 patent/US6136797A/en not_active Expired - Fee Related
- 1996-12-16 AU AU13730/97A patent/AU714236B2/en not_active Ceased
- 1996-12-16 CA CA002240366A patent/CA2240366A1/en not_active Abandoned
- 1996-12-16 HU HU0001534A patent/HUP0001534A3/hu unknown
- 1996-12-16 TR TR1998/01082T patent/TR199801082T2/xx unknown
- 1996-12-16 CN CN96180011A patent/CN1085672C/zh not_active Expired - Fee Related
- 1996-12-16 RU RU98113304/04A patent/RU2166508C2/ru not_active IP Right Cessation
- 1996-12-16 PL PL96327173A patent/PL186402B1/pl not_active IP Right Cessation
-
1998
- 1998-06-15 NO NO982754A patent/NO982754L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0001534A3 (en) | 2002-08-28 |
| CA2240366A1 (en) | 1997-06-26 |
| CN1209133A (zh) | 1999-02-24 |
| US6136797A (en) | 2000-10-24 |
| PL327173A1 (en) | 1998-11-23 |
| CN1085672C (zh) | 2002-05-29 |
| ES2230574T3 (es) | 2005-05-01 |
| HUP0001534A2 (hu) | 2001-05-28 |
| TW343975B (en) | 1998-11-01 |
| NZ325259A (en) | 2000-01-28 |
| AU1373097A (en) | 1997-07-14 |
| AU714236B2 (en) | 1999-12-23 |
| IL124790A (en) | 2002-04-21 |
| CZ291823B6 (cs) | 2003-06-18 |
| TR199801082T2 (xx) | 1998-09-21 |
| BR9612133A (pt) | 1999-07-13 |
| NO982754D0 (no) | 1998-06-15 |
| DE59611111D1 (de) | 2004-11-11 |
| PL186402B1 (pl) | 2004-01-30 |
| RU2166508C2 (ru) | 2001-05-10 |
| EP0868425B1 (de) | 2004-10-06 |
| KR20000064374A (ko) | 2000-11-06 |
| ATE278698T1 (de) | 2004-10-15 |
| EP0868425A1 (de) | 1998-10-07 |
| AR005089A1 (es) | 1999-04-14 |
| JP2000515113A (ja) | 2000-11-14 |
| IL124790A0 (en) | 1999-01-26 |
| NO982754L (no) | 1998-08-13 |
| CZ181098A3 (cs) | 1998-10-14 |
| WO1997022613A1 (de) | 1997-06-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK9293A3 (en) | New phospolipid-derivatives of nucleosides, their preparation and their use as antiviral drugs | |
| SK75698A3 (en) | Phospholipid derivatives of phosphono-carboxylic acids, the production of said derivatives and the use of said derivatives as antiviral medicaments | |
| JPH05507929A (ja) | エーテル脂質―ヌクレオシド共有結合体 | |
| WO1996039831A1 (en) | Prodrugs of pharmaceuticals with improved bioavailability | |
| US6686462B2 (en) | Antiviral compounds and methods of administration | |
| SK282035B6 (sk) | Fosfolipidické deriváty fosfonokarboxylových kyselín, ich použitie a liečivo obsahujúce aspoň jeden z týchto derivátov | |
| KR100243440B1 (ko) | 세코-누클레오시드의 리포누클레오티드, 이들의 제조방법 및 항바이러스제로서 이들을 사용하는 방법 | |
| AU722835B2 (en) | Lipid alcohols as new immunosuppressive and antiviral drugs | |
| MXPA98004755A (es) | Derivados novedosos de fosfolipidos de acidos fosfonocarboxilicos, la produccion de los mismos, asi como su uso como agentes farmaceuticos antivirales | |
| CA2165979A1 (en) | Liponucleotides of deoxynucleosides, the production thereof and their use as antiviral pharmaceutical agents | |
| US6080734A (en) | Liponucleotides of seco-nucleosides, their production as well as their use as antiviral pharmaceutical agents | |
| DE19643416A1 (de) | Neue Phospholipid-Derivate von Phosphonocarbonsäuren, deren Herstellung sowie deren Verwendung als antivirale Arzneimittel | |
| DE19547023A1 (de) | Neue Phospholipid-Derivate von Phosphonocarbonsäuren, deren Herstellung sowie deren Verwendung als antivirale Arzneimittel | |
| CZ287942B6 (cs) | Deriváty fosfolipidů nukleotidů, je obsahující léčivo a použití |