ES2251966T3 - Macrolidos con actividad anti-inflamatoria. - Google Patents
Macrolidos con actividad anti-inflamatoria.Info
- Publication number
- ES2251966T3 ES2251966T3 ES00904899T ES00904899T ES2251966T3 ES 2251966 T3 ES2251966 T3 ES 2251966T3 ES 00904899 T ES00904899 T ES 00904899T ES 00904899 T ES00904899 T ES 00904899T ES 2251966 T3 ES2251966 T3 ES 2251966T3
- Authority
- ES
- Spain
- Prior art keywords
- groups
- hydrogen
- compound
- formula
- branched
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- -1 carboxylic groups Chemical group 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 150000002923 oximes Chemical class 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 6
- 229940126214 compound 3 Drugs 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 3
- 125000000101 thioether group Chemical group 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 15
- 239000003120 macrolide antibiotic agent Substances 0.000 description 15
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 239000002158 endotoxin Substances 0.000 description 10
- 229940041033 macrolides Drugs 0.000 description 10
- 102000004890 Interleukin-8 Human genes 0.000 description 9
- 108090001007 Interleukin-8 Proteins 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229960003276 erythromycin Drugs 0.000 description 9
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 9
- 229940096397 interleukin-8 Drugs 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 229940098779 methanesulfonic acid Drugs 0.000 description 8
- 210000000440 neutrophil Anatomy 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229920006008 lipopolysaccharide Polymers 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- RXZBMPWDPOLZGW-XMRMVWPWSA-N (E)-roxithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/OCOCCOC)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 RXZBMPWDPOLZGW-XMRMVWPWSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012981 Hank's balanced salt solution Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229960002626 clarithromycin Drugs 0.000 description 4
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229960005224 roxithromycin Drugs 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000000743 Interleukin-5 Human genes 0.000 description 3
- 108010002616 Interleukin-5 Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 239000004264 Petrolatum Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 210000000038 chest Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000007306 functionalization reaction Methods 0.000 description 3
- 229940100602 interleukin-5 Drugs 0.000 description 3
- KNJDBYZZKAZQNG-UHFFFAOYSA-N lucigenin Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.C12=CC=CC=C2[N+](C)=C(C=CC=C2)C2=C1C1=C(C=CC=C2)C2=[N+](C)C2=CC=CC=C12 KNJDBYZZKAZQNG-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229940066842 petrolatum Drugs 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\O)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI99A0061 | 1999-01-15 | ||
| IT1999MI000061A IT1306205B1 (it) | 1999-01-15 | 1999-01-15 | Macrolidi ad attivita' antiinfiammatoria. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2251966T3 true ES2251966T3 (es) | 2006-05-16 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00904899T Expired - Lifetime ES2251966T3 (es) | 1999-01-15 | 2000-01-12 | Macrolidos con actividad anti-inflamatoria. |
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|---|---|
| US (1) | US6455576B1 (https=) |
| EP (1) | EP1144427B1 (https=) |
| JP (1) | JP4568433B2 (https=) |
| CN (1) | CN1151165C (https=) |
| AT (1) | ATE308552T1 (https=) |
| AU (1) | AU769006B2 (https=) |
| BR (1) | BR0007514A (https=) |
| CA (1) | CA2368400C (https=) |
| DE (1) | DE60023647T2 (https=) |
| ES (1) | ES2251966T3 (https=) |
| HU (1) | HU229228B1 (https=) |
| IL (2) | IL144044A0 (https=) |
| IT (1) | IT1306205B1 (https=) |
| MX (1) | MXPA01007164A (https=) |
| NO (1) | NO318982B1 (https=) |
| RU (1) | RU2243230C2 (https=) |
| SK (1) | SK286772B6 (https=) |
| WO (1) | WO2000042055A2 (https=) |
| ZA (1) | ZA200105748B (https=) |
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| HRP20010018A2 (en) | 2001-01-09 | 2002-12-31 | Pliva D D | Novel anti-inflammatory compounds |
| AU2003264917A1 (en) | 2002-07-08 | 2004-01-23 | Pliva - Istrazivacki Institut D.O.O. | Hybrid molecules of macrolides with steroid/non-steroid anti-inflammatory, antineoplastic and antiviral active molecules |
| RS20050008A (sr) | 2002-07-08 | 2007-06-04 | Pliva-Istraživački Institut D.O.O., | Nova jedinjenja,kompozicije i metode za lečenje inflamatornih oboljenja i stanja |
| EP1521763A2 (en) * | 2002-07-08 | 2005-04-13 | Pliva - Istrazivacki Institut d.o.o. | Novel nonsteroidal anti-inflammatory substances, compositions and methods for their use |
| ITMI20021726A1 (it) | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| TW200420573A (en) | 2002-09-26 | 2004-10-16 | Rib X Pharmaceuticals Inc | Bifunctional heterocyclic compounds and methods of making and using same |
| ITMI20022292A1 (it) * | 2002-10-29 | 2004-04-30 | Zambon Spa | 9a-azalidi ad attivita' antiinfiammatoria. |
| BRPI0410638A (pt) * | 2003-04-17 | 2006-06-13 | Sandoz Ag | derivados de azitromicina |
| HRP20030324A2 (en) | 2003-04-24 | 2005-02-28 | Pliva-Istra�iva�ki institut d.o.o. | Compounds of antiinflammatory effect |
| ITMI20040124A1 (it) * | 2004-01-29 | 2004-04-29 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria |
| WO2006130128A2 (en) * | 2004-02-18 | 2006-12-07 | Chiron Corporation | Methods of identifying anti-inflammatory macrolides |
| EP1723159B1 (en) | 2004-02-27 | 2019-06-12 | Melinta Therapeutics, Inc. | Macrocyclic compounds and methods of making and using the same |
| WO2006035301A2 (en) * | 2004-09-27 | 2006-04-06 | Ranbaxy Laboratories Limited | Erythromycin a derivatives as antibacterial agents |
| ES2337915T3 (es) | 2004-10-27 | 2010-04-30 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | Conjugados con adtividad antiinflamatoria. |
| US20080249034A1 (en) * | 2005-03-21 | 2008-10-09 | Zambon S.P.A. | Use of Macrolides for Treating Intestinal Inflammation |
| US7582611B2 (en) * | 2005-05-24 | 2009-09-01 | Pfizer Inc. | Motilide compounds |
| US20110178287A1 (en) | 2010-01-19 | 2011-07-21 | Cerulean Pharma Inc. | Cyclodextrin-based polymers for therapeutic delivery |
| RU2455309C2 (ru) * | 2010-07-20 | 2012-07-10 | Открытое Акционерное Общество "Татхимфармпрепараты" | Способ получения аморфной формы рокситромицина |
| GB201608236D0 (en) | 2016-05-11 | 2016-06-22 | Fidelta D O O | Seco macrolide compounds |
| TWI830987B (zh) | 2020-03-12 | 2024-02-01 | 美商碩騰服務公司 | 免疫調節脲氮雜內酯 |
| WO2021195126A1 (en) | 2020-03-24 | 2021-09-30 | Burnet Michael W | Anti-infective and anti-viral compounds and compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928387A (en) * | 1974-02-04 | 1975-12-23 | Hoffmann La Roche | Antibiotic 1745A/X and methods for the production thereof |
| IT1189285B (it) * | 1982-05-28 | 1988-02-04 | Nuovo Consor Sanitar Nazionale | Sali dell'antibiotico eritromicina e del suo estere propionico con acidi ad attivita' terapeutica coadiuvante |
| EP0254534A3 (en) * | 1986-07-24 | 1991-04-17 | William S. Robinson | Erythromycin derivatives and compositions and use for inhibiting virus replication and disease |
| FR2697524B1 (fr) * | 1992-11-05 | 1994-12-23 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| IT1276901B1 (it) * | 1994-12-13 | 1997-11-03 | Zambon Spa | Derivati dell'eritromicina a 9-0-ossina dotati di attivita' antibiotica |
| KR19980701895A (ko) * | 1995-03-08 | 1998-06-25 | 이라우치지마 가즈다카 | 면역관련병 처치제 및 그의 탐색 방법 |
-
1999
- 1999-01-15 IT IT1999MI000061A patent/IT1306205B1/it active
-
2000
- 2000-01-12 WO PCT/EP2000/000163 patent/WO2000042055A2/en not_active Ceased
- 2000-01-12 AT AT00904899T patent/ATE308552T1/de not_active IP Right Cessation
- 2000-01-12 EP EP00904899A patent/EP1144427B1/en not_active Expired - Lifetime
- 2000-01-12 HU HU0105105A patent/HU229228B1/hu not_active IP Right Cessation
- 2000-01-12 AU AU26636/00A patent/AU769006B2/en not_active Ceased
- 2000-01-12 CN CNB008027676A patent/CN1151165C/zh not_active Expired - Fee Related
- 2000-01-12 JP JP2000593622A patent/JP4568433B2/ja not_active Expired - Fee Related
- 2000-01-12 CA CA002368400A patent/CA2368400C/en not_active Expired - Fee Related
- 2000-01-12 ES ES00904899T patent/ES2251966T3/es not_active Expired - Lifetime
- 2000-01-12 DE DE60023647T patent/DE60023647T2/de not_active Expired - Lifetime
- 2000-01-12 MX MXPA01007164A patent/MXPA01007164A/es unknown
- 2000-01-12 BR BR0007514-0A patent/BR0007514A/pt not_active IP Right Cessation
- 2000-01-12 SK SK981-2001A patent/SK286772B6/sk not_active IP Right Cessation
- 2000-01-12 IL IL14404400A patent/IL144044A0/xx active IP Right Grant
- 2000-01-12 RU RU2001118831/04A patent/RU2243230C2/ru not_active IP Right Cessation
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2001
- 2001-01-12 US US09/889,284 patent/US6455576B1/en not_active Expired - Lifetime
- 2001-06-28 IL IL144044A patent/IL144044A/en not_active IP Right Cessation
- 2001-07-12 ZA ZA200105748A patent/ZA200105748B/en unknown
- 2001-07-16 NO NO20013517A patent/NO318982B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1151165C (zh) | 2004-05-26 |
| AU2663600A (en) | 2000-08-01 |
| ATE308552T1 (de) | 2005-11-15 |
| DE60023647T2 (de) | 2006-08-10 |
| NO20013517D0 (no) | 2001-07-16 |
| JP4568433B2 (ja) | 2010-10-27 |
| HUP0105105A2 (hu) | 2002-04-29 |
| EP1144427B1 (en) | 2005-11-02 |
| CA2368400A1 (en) | 2000-07-20 |
| BR0007514A (pt) | 2001-11-20 |
| IL144044A (en) | 2006-12-31 |
| MXPA01007164A (es) | 2002-03-27 |
| IL144044A0 (en) | 2002-04-21 |
| IT1306205B1 (it) | 2001-05-30 |
| RU2243230C2 (ru) | 2004-12-27 |
| SK286772B6 (sk) | 2009-05-07 |
| HU229228B1 (en) | 2013-09-30 |
| ZA200105748B (en) | 2002-10-14 |
| EP1144427A2 (en) | 2001-10-17 |
| HUP0105105A3 (en) | 2003-05-28 |
| JP2002534531A (ja) | 2002-10-15 |
| DE60023647D1 (de) | 2005-12-08 |
| US6455576B1 (en) | 2002-09-24 |
| CN1336932A (zh) | 2002-02-20 |
| ITMI990061A1 (it) | 2000-07-15 |
| SK9812001A3 (en) | 2002-01-07 |
| WO2000042055A2 (en) | 2000-07-20 |
| EP1144427A3 (en) | 2002-08-28 |
| WO2000042055A3 (en) | 2001-09-07 |
| NO20013517L (no) | 2001-07-16 |
| NO318982B1 (no) | 2005-05-30 |
| AU769006B2 (en) | 2004-01-15 |
| CA2368400C (en) | 2007-06-05 |
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