IL109543A - Pharmaceutical compositions containing spiropiperidyl derivatives of rifamycin s for reducing severity of toxoplasmosis - Google Patents
Pharmaceutical compositions containing spiropiperidyl derivatives of rifamycin s for reducing severity of toxoplasmosisInfo
- Publication number
- IL109543A IL109543A IL109543A IL10954394A IL109543A IL 109543 A IL109543 A IL 109543A IL 109543 A IL109543 A IL 109543A IL 10954394 A IL10954394 A IL 10954394A IL 109543 A IL109543 A IL 109543A
- Authority
- IL
- Israel
- Prior art keywords
- rifabutin
- spiropiperidyl
- combination
- rifamycin
- infection
- Prior art date
Links
- 201000005485 Toxoplasmosis Diseases 0.000 title claims abstract description 59
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 title description 11
- 239000008194 pharmaceutical composition Substances 0.000 title description 6
- 238000011282 treatment Methods 0.000 claims abstract description 69
- 208000015181 infectious disease Diseases 0.000 claims abstract description 63
- 241000223997 Toxoplasma gondii Species 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 claims abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 14
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 7
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical group OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 claims abstract description 4
- 229960000885 rifabutin Drugs 0.000 claims description 122
- ZWBTYMGEBZUQTK-PVLSIAFMSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c4NC5(CCN(CC(C)C)CC5)N=c4c(=NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C ZWBTYMGEBZUQTK-PVLSIAFMSA-N 0.000 claims description 112
- 239000003814 drug Substances 0.000 claims description 47
- 229940079593 drug Drugs 0.000 claims description 42
- 229940124530 sulfonamide Drugs 0.000 claims description 20
- 150000003456 sulfonamides Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 206010014599 encephalitis Diseases 0.000 claims description 10
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 8
- CSFWPUWCSPOLJW-UHFFFAOYSA-N hydroxynaphthoquinone Natural products C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 4
- 239000004052 folic acid antagonist Substances 0.000 claims description 3
- 229940123414 Folate antagonist Drugs 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 7
- 241000699670 Mus sp. Species 0.000 description 80
- 230000000694 effects Effects 0.000 description 35
- 229960002227 clindamycin Drugs 0.000 description 25
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 25
- 208000031513 cyst Diseases 0.000 description 23
- 229960003159 atovaquone Drugs 0.000 description 22
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 21
- 229960000611 pyrimethamine Drugs 0.000 description 21
- 201000010099 disease Diseases 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 229960004306 sulfadiazine Drugs 0.000 description 20
- 230000001154 acute effect Effects 0.000 description 19
- KUCQYCKVKVOKAY-CTYIDZIISA-N atovaquone Chemical compound C1([C@H]2CC[C@@H](CC2)C2=C(C(C3=CC=CC=C3C2=O)=O)O)=CC=C(Cl)C=C1 KUCQYCKVKVOKAY-CTYIDZIISA-N 0.000 description 19
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 19
- 210000000059 tachyzoite Anatomy 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 17
- 238000001727 in vivo Methods 0.000 description 17
- 244000045947 parasite Species 0.000 description 17
- QCLZTUZOMPXOSC-WJGMNZNNSA-N spiropiperidylrifamycin Chemical class O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC(=C2N3)C(=O)C=4C(O)=C5C)C)OC)C5=C1C=4C2=NC13CCNCC1 QCLZTUZOMPXOSC-WJGMNZNNSA-N 0.000 description 17
- 208000030507 AIDS Diseases 0.000 description 16
- 230000004083 survival effect Effects 0.000 description 15
- -1 rifampin Chemical class 0.000 description 14
- YVOFSHPIJOYKSH-NLYBMVFSSA-M sodium rifomycin sv Chemical group [Na+].OC1=C(C(O)=C2C)C3=C([O-])C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O YVOFSHPIJOYKSH-NLYBMVFSSA-M 0.000 description 14
- 210000003754 fetus Anatomy 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 210000004556 brain Anatomy 0.000 description 12
- 229930189077 Rifamycin Natural products 0.000 description 11
- 229960004099 azithromycin Drugs 0.000 description 10
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 10
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 10
- 229960001225 rifampicin Drugs 0.000 description 10
- 229940081192 rifamycins Drugs 0.000 description 10
- 206010061598 Immunodeficiency Diseases 0.000 description 9
- 238000011321 prophylaxis Methods 0.000 description 9
- 238000003304 gavage Methods 0.000 description 8
- 238000010172 mouse model Methods 0.000 description 8
- 230000002195 synergetic effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000223996 Toxoplasma Species 0.000 description 7
- 229960002626 clarithromycin Drugs 0.000 description 7
- 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 7
- 239000002953 phosphate buffered saline Substances 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 6
- 239000007928 intraperitoneal injection Substances 0.000 description 6
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- 229940088710 antibiotic agent Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
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- 150000004340 hydroxynaphthoquinones Chemical class 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 description 4
- BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 description 4
- 239000004187 Spiramycin Substances 0.000 description 4
- 241000504303 Toxoplasma gondii RH Species 0.000 description 4
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- 239000003085 diluting agent Substances 0.000 description 4
- 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 4
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- 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 3
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- 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 2
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- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 description 2
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- ATEBXHFBFRCZMA-VXTBVIBXSA-N rifabutin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC(=C2N3)C(=O)C=4C(O)=C5C)C)OC)C5=C1C=4C2=NC13CCN(CC(C)C)CC1 ATEBXHFBFRCZMA-VXTBVIBXSA-N 0.000 description 2
- SQTCRTQCPJICLD-KTQDUKAHSA-N rifamycin B Chemical compound OC1=C(C(O)=C2C)C3=C(OCC(O)=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O SQTCRTQCPJICLD-KTQDUKAHSA-N 0.000 description 2
- SQTCRTQCPJICLD-OQQFTUDCSA-N rifomycin-B Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(OCC(=O)O)c4c3C2=O SQTCRTQCPJICLD-OQQFTUDCSA-N 0.000 description 2
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- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 2
- 229960002135 sulfadimidine Drugs 0.000 description 2
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 2
- VACCAVUAMIDAGB-UHFFFAOYSA-N sulfamethizole Chemical compound S1C(C)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 VACCAVUAMIDAGB-UHFFFAOYSA-N 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 2
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 2
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- 239000002459 polyene antibiotic agent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000020995 raw meat Nutrition 0.000 description 1
- 229950010526 relomycin Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940063639 rifadin Drugs 0.000 description 1
- 229950003104 rifamide Drugs 0.000 description 1
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- VFYNXKZVOUXHDX-VDPUEHCXSA-N rifamycin b diethylamide Chemical compound CC1=C(O)C(C=2O)=C3C(OCC(=O)N(CC)CC)=CC=2NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]2(C)OC1=C3C2=O VFYNXKZVOUXHDX-VDPUEHCXSA-N 0.000 description 1
- 229940109171 rifamycin sv Drugs 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RGHFKWPGWBFQLN-UHFFFAOYSA-M sodium;5,5-diethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CCC1(CC)C([O-])=NC(=O)NC1=O RGHFKWPGWBFQLN-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 208000000995 spontaneous abortion Diseases 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002673 sulfacetamide Drugs 0.000 description 1
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 1
- 229960000973 sulfadimethoxine Drugs 0.000 description 1
- 229960004257 sulfaguanidine Drugs 0.000 description 1
- BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 1
- 229960005158 sulfamethizole Drugs 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- 229960001544 sulfathiazole Drugs 0.000 description 1
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- 239000000375 suspending agent Substances 0.000 description 1
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- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 231100000378 teratogenic Toxicity 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960005041 troleandomycin Drugs 0.000 description 1
- LQCLVBQBTUVCEQ-QTFUVMRISA-N troleandomycin Chemical compound O1[C@@H](C)[C@H](OC(C)=O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](OC(C)=O)[C@@H](C)C(=O)[C@@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(C)=O)[C@H]1C LQCLVBQBTUVCEQ-QTFUVMRISA-N 0.000 description 1
- 229960004059 tylosin Drugs 0.000 description 1
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
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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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5728893A | 1993-05-05 | 1993-05-05 | |
| US08/203,539 US5529994A (en) | 1993-05-05 | 1994-02-28 | Treatment for toxoplasmosis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL109543A0 IL109543A0 (en) | 1994-08-26 |
| IL109543A true IL109543A (en) | 1998-06-15 |
Family
ID=26736295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL109543A IL109543A (en) | 1993-05-05 | 1994-05-04 | Pharmaceutical compositions containing spiropiperidyl derivatives of rifamycin s for reducing severity of toxoplasmosis |
Country Status (14)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9224739D0 (en) * | 1992-11-26 | 1993-01-13 | Wellcome Found | Medicaments |
| GB9424013D0 (en) * | 1994-11-29 | 1995-01-18 | Wellcome Found | Medicaments |
| US6710033B1 (en) | 1996-08-14 | 2004-03-23 | Vanderbilt University | Methods and treatment of multiple sclerosis |
| US6258532B1 (en) | 1997-08-14 | 2001-07-10 | Vanderbilt University | Methods for in vitro susceptibility testing of chlamydia |
| US6579854B1 (en) | 1996-08-14 | 2003-06-17 | Vanderbilt University | Diagnosis and management of infection caused by chlamydia |
| US6890526B2 (en) | 1997-05-06 | 2005-05-10 | Vanderbilt University | Methods and reagents for the treatment of multiple sclerosis |
| AU3760400A (en) * | 1999-03-19 | 2000-10-09 | Vanderbilt University | Methods and reagents for the diagnosis and treatment of multiple sclerosis |
| US6429231B1 (en) * | 2001-09-24 | 2002-08-06 | Bradley Pharmaceuticals, Inc. | Compositions containing antimicrobials and urea for the treatment of dermatological disorders and methods for their use |
| US7074832B2 (en) | 2001-09-24 | 2006-07-11 | Bradley Pharmaceuticals, Inc. | Compositions containing antimicrobials and urea for the treatment of dermatological disorders and methods for their use |
| JP2003327536A (ja) * | 2002-03-07 | 2003-11-19 | Kitasato Inst:The | ヒト免疫不全症候群ウイルスの感染、増殖抑制剤 |
| US6858083B2 (en) * | 2002-06-05 | 2005-02-22 | Scimed Lifesystems, Inc. | Apparatus and method for closed-loop control of RF generator for welding polymeric catheter components |
| US20030017985A1 (en) * | 2002-07-02 | 2003-01-23 | Taylor Gregory Alan | Molecules that influence pathogen resistance |
| RU2255730C1 (ru) * | 2003-10-14 | 2005-07-10 | Федеральное государственное унитарное предприятие "Всероссийкий научный центр по безопасности биологически активных веществ" (ФГУП "ВНЦ БАВ") | Стабильная фармацевтическая суспензия азитромицина и способ ее получения |
| DE102004055316A1 (de) * | 2004-11-16 | 2006-05-18 | Bayer Healthcare Ag | Verhinderung vertikaler Endoparasiten-Infektionen |
| TWI368509B (en) | 2005-10-05 | 2012-07-21 | Otsuka Pharma Co Ltd | Antituberculous therapeutic drugs and kit containing the same |
| US7799885B2 (en) | 2005-11-30 | 2010-09-21 | Corning Incorporated | Photo or electron beam curable compositions |
| US20090054380A1 (en) * | 2005-12-20 | 2009-02-26 | Greenstein Robert J | Methods for diagnosing and treating a mycobacterium avium subspecies paratuberculosis infection |
| SG10201405158QA (en) * | 2006-02-24 | 2014-10-30 | Callida Genomics Inc | High throughput genome sequencing on dna arrays |
| RU2320337C1 (ru) * | 2006-06-09 | 2008-03-27 | Федеральное государственное унитарное предприятие "Государственный научный центр по антибиотикам" | Способ получения антимикробной композиции с рифабутином |
| FR2944014A1 (fr) | 2009-04-06 | 2010-10-08 | Univ Grenoble 1 | Peptides cycliques a activite antiparasitaire |
| CN114601840A (zh) * | 2020-12-08 | 2022-06-10 | 复旦大学附属中山医院 | 一种联合用药,用于治疗卡氏肺孢子虫肺炎 |
| CN113230248A (zh) * | 2021-06-18 | 2021-08-10 | 宁波大学 | 利卡灵-b及其组合物在制备治疗或预防弓形虫病药物中的应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644616A (en) * | 1969-03-24 | 1972-02-22 | Ciba Geigy Corp | Synergistic composition of rifampicin and streptomycin |
| US4054663A (en) * | 1974-12-23 | 1977-10-18 | Sankyo Company Limited | Pyridine derivatives and their use as anticoccidial agents |
| US4094982A (en) * | 1975-05-15 | 1978-06-13 | Sankyo Company Limited | Pyridine sulfonamides and their use as anticoccidial agents |
| IT1056272B (it) * | 1975-06-13 | 1982-01-30 | Archifar Ind Chim Trentino | Prodotti derivati dalle amine aromatiche |
| IT1135270B (it) * | 1980-04-12 | 1986-08-20 | Erba Farmitalia | 3-amidino-ansamicine |
| US5053432A (en) * | 1983-04-14 | 1991-10-01 | Burroughs Wellcome Co. | Naphthoquinone derivatives |
| US5175319A (en) * | 1983-04-14 | 1992-12-29 | Burroughs Wellcome Co. | Naphthoquinone derivatives |
| DE3512194A1 (de) * | 1985-04-03 | 1986-10-09 | Hoechst Ag, 6230 Frankfurt | Ein neues ansamycin-antibiotikum, ein mikrobielles verfahren zu seiner herstellung und seine verwendung als arzneimittel |
| WO1989002271A1 (en) * | 1987-09-10 | 1989-03-23 | Pfizer | Azithromycin and derivatives as antiprotozoal agents |
| GB9000241D0 (en) * | 1990-01-05 | 1990-03-07 | Coopers Animal Health | Pharmaceutical use |
| US5529994A (en) * | 1993-05-05 | 1996-06-25 | Palo Alto Medical Foundation | Treatment for toxoplasmosis |
-
1994
- 1994-04-29 CA CA002138643A patent/CA2138643A1/en not_active Abandoned
- 1994-04-29 DE DE69400631T patent/DE69400631T2/de not_active Expired - Fee Related
- 1994-04-29 EP EP94917283A patent/EP0648121B1/en not_active Expired - Lifetime
- 1994-04-29 JP JP6524580A patent/JPH07509003A/ja active Pending
- 1994-04-29 RU RU95105973A patent/RU2121838C1/ru active
- 1994-04-29 AT AT94917283T patent/ATE143601T1/de not_active IP Right Cessation
- 1994-04-29 WO PCT/US1994/004765 patent/WO1994025038A1/en active IP Right Grant
- 1994-04-29 DK DK94917283.7T patent/DK0648121T3/da active
- 1994-04-29 AU AU69050/94A patent/AU669300B2/en not_active Ceased
- 1994-04-29 ES ES94917283T patent/ES2095772T3/es not_active Expired - Lifetime
- 1994-05-04 IL IL109543A patent/IL109543A/en not_active IP Right Cessation
-
1995
- 1995-01-04 NO NO950030A patent/NO950030L/no unknown
- 1995-06-07 US US08/487,721 patent/US5665707A/en not_active Expired - Fee Related
- 1995-06-07 US US08/481,689 patent/US5641769A/en not_active Expired - Fee Related
- 1995-06-07 US US08/481,741 patent/US5650405A/en not_active Expired - Fee Related
- 1995-06-07 US US08/476,508 patent/US5670496A/en not_active Expired - Fee Related
- 1995-06-07 US US08/474,998 patent/US5648345A/en not_active Expired - Fee Related
-
1996
- 1996-11-28 GR GR960403219T patent/GR3021828T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69400631T2 (de) | 1997-02-27 |
| NO950030D0 (no) | 1995-01-04 |
| AU6905094A (en) | 1994-11-21 |
| ES2095772T3 (es) | 1997-02-16 |
| DE69400631D1 (de) | 1996-11-07 |
| NO950030L (no) | 1995-01-04 |
| US5670496A (en) | 1997-09-23 |
| US5650405A (en) | 1997-07-22 |
| US5641769A (en) | 1997-06-24 |
| GR3021828T3 (en) | 1997-02-28 |
| EP0648121B1 (en) | 1996-10-02 |
| WO1994025038A1 (en) | 1994-11-10 |
| CA2138643A1 (en) | 1994-11-10 |
| EP0648121A1 (en) | 1995-04-19 |
| IL109543A0 (en) | 1994-08-26 |
| ATE143601T1 (de) | 1996-10-15 |
| RU95105973A (ru) | 1997-01-20 |
| JPH07509003A (ja) | 1995-10-05 |
| RU2121838C1 (ru) | 1998-11-20 |
| US5648345A (en) | 1997-07-15 |
| AU669300B2 (en) | 1996-05-30 |
| DK0648121T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1997-02-24 |
| US5665707A (en) | 1997-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| RH | Patent void |