NO328544B1 - Streptograminderivater, en fremgangsmate for fremstilling derav samt farmasoytiske preparater inneholdende derivatene og assosiasjoner omfattende derivatene - Google Patents
Streptograminderivater, en fremgangsmate for fremstilling derav samt farmasoytiske preparater inneholdende derivatene og assosiasjoner omfattende derivatene Download PDFInfo
- Publication number
- NO328544B1 NO328544B1 NO20020404A NO20020404A NO328544B1 NO 328544 B1 NO328544 B1 NO 328544B1 NO 20020404 A NO20020404 A NO 20020404A NO 20020404 A NO20020404 A NO 20020404A NO 328544 B1 NO328544 B1 NO 328544B1
- Authority
- NO
- Norway
- Prior art keywords
- residue
- alkyl
- pristinamycin
- saturated
- derivative
- Prior art date
Links
- 108010034396 Streptogramins Proteins 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 15
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 19
- 125000003118 aryl group Chemical group 0.000 claims description 164
- 229960003961 pristinamycin Drugs 0.000 claims description 138
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 229920006395 saturated elastomer Polymers 0.000 claims description 70
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
- JOOMGSFOCRDAHL-XKCHLWDXSA-N pristinamycin-IIB Natural products CC(C)[C@@H]1OC(=O)[C@H]2CCCN2C(=O)c3coc(CC(=O)C[C@@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3 JOOMGSFOCRDAHL-XKCHLWDXSA-N 0.000 claims description 35
- -1 C3-galkenyl Chemical group 0.000 claims description 34
- 108010079780 Pristinamycin Proteins 0.000 claims description 33
- YVMBAUWDIGJRNY-BESUKNQGSA-N 4o8o7q7iu4 Chemical compound C1C(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@@H](C)[C@@H](C(C)C)OC(=O)C2=CCCN2C(=O)C2=COC1=N2.N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YVMBAUWDIGJRNY-BESUKNQGSA-N 0.000 claims description 32
- RLNUPSVMIYRZSM-UHFFFAOYSA-N Pristinamycin Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(=CC=2)N(C)C)CCN(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O RLNUPSVMIYRZSM-UHFFFAOYSA-N 0.000 claims description 31
- DAIKHDNSXMZDCU-OUDXUNEISA-N pristinamycin-IIA Natural products CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@@H]1C)n3 DAIKHDNSXMZDCU-OUDXUNEISA-N 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 238000004587 chromatography analysis Methods 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 239000000460 chlorine Chemical group 0.000 claims description 18
- 229940041030 streptogramins Drugs 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 6
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 150000002148 esters Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 108010015791 Streptogramin A Proteins 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 239000012025 fluorinating agent Substances 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 538
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 251
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 191
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 146
- 239000007787 solid Substances 0.000 description 125
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 95
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 84
- 239000000203 mixture Substances 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 61
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 41
- 239000000377 silicon dioxide Substances 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
- 239000012074 organic phase Substances 0.000 description 35
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 34
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
- 239000008346 aqueous phase Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 235000017557 sodium bicarbonate Nutrition 0.000 description 27
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
- 229910052938 sodium sulfate Inorganic materials 0.000 description 27
- 235000011152 sodium sulphate Nutrition 0.000 description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
- 239000000155 melt Substances 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
- 238000010828 elution Methods 0.000 description 14
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 238000002953 preparative HPLC Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 6
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 238000000451 chemical ionisation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000009471 action Effects 0.000 description 3
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- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- MBXKCLHOVPXMCJ-UHFFFAOYSA-N 3-(mercaptomethylene)pyridine Chemical compound SCC1=CC=CN=C1 MBXKCLHOVPXMCJ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241001070941 Castanea Species 0.000 description 2
- 235000014036 Castanea Nutrition 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
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- 239000004006 olive oil Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 238000012306 spectroscopic technique Methods 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
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository 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
- 150000003892 tartrate salts Chemical class 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- FEPMHVLSLDOMQC-UHFFFAOYSA-N virginiamycin-S1 Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC=CC=2)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O FEPMHVLSLDOMQC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed 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
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9909708A FR2796949B1 (fr) | 1999-07-27 | 1999-07-27 | Derives de streptogramines, leur preparation et les compositions qui les contiennent |
| PCT/FR2000/002146 WO2001010895A1 (fr) | 1999-07-27 | 2000-07-26 | Derives de streptogramines, leur preparation et les compositions qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20020404D0 NO20020404D0 (no) | 2002-01-25 |
| NO20020404L NO20020404L (no) | 2002-03-21 |
| NO328544B1 true NO328544B1 (no) | 2010-03-15 |
Family
ID=9548546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20020404A NO328544B1 (no) | 1999-07-27 | 2002-01-25 | Streptograminderivater, en fremgangsmate for fremstilling derav samt farmasoytiske preparater inneholdende derivatene og assosiasjoner omfattende derivatene |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US6541451B1 (et) |
| EP (1) | EP1204675B1 (et) |
| JP (1) | JP4326178B2 (et) |
| KR (3) | KR100824479B1 (et) |
| CN (1) | CN1360592B (et) |
| AP (1) | AP1376A (et) |
| AR (1) | AR024937A1 (et) |
| AT (1) | ATE240970T1 (et) |
| AU (1) | AU778033B2 (et) |
| BG (1) | BG65108B1 (et) |
| BR (1) | BR0012761B1 (et) |
| CA (1) | CA2380305C (et) |
| CL (1) | CL2004001094A1 (et) |
| CZ (1) | CZ2002227A3 (et) |
| DE (1) | DE60002891T2 (et) |
| DK (1) | DK1204675T3 (et) |
| DZ (1) | DZ3204A1 (et) |
| EA (1) | EA004297B1 (et) |
| EE (1) | EE05038B1 (et) |
| ES (1) | ES2199855T3 (et) |
| FR (1) | FR2796949B1 (et) |
| GE (1) | GEP20063973B (et) |
| HK (1) | HK1047114A1 (et) |
| HR (1) | HRP20020047B1 (et) |
| HU (1) | HUP0202594A3 (et) |
| IL (2) | IL146812A0 (et) |
| MA (1) | MA26809A1 (et) |
| MX (1) | MXPA02000319A (et) |
| NO (1) | NO328544B1 (et) |
| NZ (1) | NZ516621A (et) |
| OA (1) | OA11996A (et) |
| PL (1) | PL201854B1 (et) |
| PT (1) | PT1204675E (et) |
| RS (1) | RS50384B (et) |
| SK (1) | SK1132002A3 (et) |
| TN (1) | TNSN00164A1 (et) |
| UA (1) | UA73512C2 (et) |
| WO (1) | WO2001010895A1 (et) |
| ZA (1) | ZA200200312B (et) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2775288B1 (fr) * | 1998-02-26 | 2000-03-31 | Rhone Poulenc Rorer Sa | Derives de streptogramines, leur preparation et les compositons qui les contiennent |
| US7232799B2 (en) | 2000-12-21 | 2007-06-19 | Aventis Pharma Sa | Streptogramin derivatives and compositions thereof |
| US6596717B2 (en) | 2000-12-21 | 2003-07-22 | Aventis Pharma S.A. | Streptogramin derivatives, their preparation and compositions which contain them |
| EP4157268A1 (en) | 2020-05-27 | 2023-04-05 | Università Degli Studi Di Trento | New therapy for the treatment of tumors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2549063B1 (fr) * | 1983-07-13 | 1985-10-25 | Rhone Poulenc Sante | Nouveaux derives de synergistines, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2576022B1 (fr) * | 1985-01-11 | 1987-09-11 | Rhone Poulenc Sante | Nouveaux derives de la pristinamycine ii b, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2599036B1 (fr) * | 1986-05-22 | 1988-09-09 | Rhone Poulenc Sante | Nouveaux derives de synergistines, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2722210B1 (fr) * | 1994-07-08 | 1996-08-14 | Rhone Poulenc Rorer Sa | Nouvelles streptogramines et procede de preparation de streptogramines par mutasynthese |
| FR2723372B1 (fr) | 1994-08-02 | 1996-10-04 | Rhone Poulenc Rorer Sa | Nouveaux derives de streptogramine, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2733236B1 (fr) | 1995-04-18 | 1997-05-23 | Rhone Poulenc Rorer Sa | Procede de preparation de streptogramines |
| FR2775288B1 (fr) * | 1998-02-26 | 2000-03-31 | Rhone Poulenc Rorer Sa | Derives de streptogramines, leur preparation et les compositons qui les contiennent |
-
1999
- 1999-07-27 FR FR9909708A patent/FR2796949B1/fr not_active Expired - Fee Related
-
2000
- 2000-07-25 AR ARP000103848A patent/AR024937A1/es active IP Right Grant
- 2000-07-26 CN CN008101833A patent/CN1360592B/zh not_active Expired - Fee Related
- 2000-07-26 AP APAP/P/2002/002402A patent/AP1376A/en active
- 2000-07-26 RS YUP-53/02A patent/RS50384B/sr unknown
- 2000-07-26 DE DE60002891T patent/DE60002891T2/de not_active Expired - Lifetime
- 2000-07-26 KR KR1020027001046A patent/KR100824479B1/ko not_active IP Right Cessation
- 2000-07-26 ES ES00958620T patent/ES2199855T3/es not_active Expired - Lifetime
- 2000-07-26 AT AT00958620T patent/ATE240970T1/de active
- 2000-07-26 PL PL353306A patent/PL201854B1/pl not_active IP Right Cessation
- 2000-07-26 DK DK00958620T patent/DK1204675T3/da active
- 2000-07-26 EE EEP200200043A patent/EE05038B1/et not_active IP Right Cessation
- 2000-07-26 IL IL14681200A patent/IL146812A0/xx unknown
- 2000-07-26 PT PT00958620T patent/PT1204675E/pt unknown
- 2000-07-26 SK SK113-2002A patent/SK1132002A3/sk unknown
- 2000-07-26 KR KR1020087019597A patent/KR20080077414A/ko not_active Application Discontinuation
- 2000-07-26 BR BRPI0012761-2A patent/BR0012761B1/pt not_active IP Right Cessation
- 2000-07-26 TN TNTNSN00164A patent/TNSN00164A1/fr unknown
- 2000-07-26 OA OA1200200023A patent/OA11996A/fr unknown
- 2000-07-26 HU HU0202594A patent/HUP0202594A3/hu unknown
- 2000-07-26 MX MXPA02000319A patent/MXPA02000319A/es active IP Right Grant
- 2000-07-26 UA UA2002010570A patent/UA73512C2/uk unknown
- 2000-07-26 WO PCT/FR2000/002146 patent/WO2001010895A1/fr active Application Filing
- 2000-07-26 CZ CZ2002227A patent/CZ2002227A3/cs unknown
- 2000-07-26 GE GE4723A patent/GEP20063973B/en unknown
- 2000-07-26 NZ NZ516621A patent/NZ516621A/en not_active IP Right Cessation
- 2000-07-26 JP JP2001515703A patent/JP4326178B2/ja not_active Expired - Fee Related
- 2000-07-26 KR KR1020077012826A patent/KR20070067244A/ko not_active Application Discontinuation
- 2000-07-26 AU AU70083/00A patent/AU778033B2/en not_active Ceased
- 2000-07-26 EP EP00958620A patent/EP1204675B1/fr not_active Expired - Lifetime
- 2000-07-26 EA EA200200197A patent/EA004297B1/ru not_active IP Right Cessation
- 2000-07-26 CA CA2380305A patent/CA2380305C/fr not_active Expired - Fee Related
- 2000-07-26 DZ DZ003204A patent/DZ3204A1/xx active
- 2000-07-27 US US09/627,791 patent/US6541451B1/en not_active Expired - Lifetime
-
2001
- 2001-11-29 IL IL146812A patent/IL146812A/en not_active IP Right Cessation
-
2002
- 2002-01-14 ZA ZA200200312A patent/ZA200200312B/en unknown
- 2002-01-17 HR HR20020047A patent/HRP20020047B1/xx not_active IP Right Cessation
- 2002-01-21 MA MA26493A patent/MA26809A1/fr unknown
- 2002-01-25 BG BG106352A patent/BG65108B1/bg unknown
- 2002-01-25 NO NO20020404A patent/NO328544B1/no not_active IP Right Cessation
- 2002-11-29 HK HK02108626.3A patent/HK1047114A1/xx not_active IP Right Cessation
-
2004
- 2004-05-18 CL CL200401094A patent/CL2004001094A1/es unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |