UA73512C2 - Streptogramines derivatives, a method for the preparation thereof and composition based thereon - Google Patents

Streptogramines derivatives, a method for the preparation thereof and composition based thereon Download PDF

Info

Publication number: UA73512C2
Authority: UA; Ukraine
Prior art keywords: radical; alkyl; substituted; saturated; radicals
Prior art date: 1999-07-27

Application number

UA2002010570A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Aventis Pharma Sa

Priority date (The priority date 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 date listed.)

1999-07-27

Filing date

2000-07-26

Publication date

2005-08-15

2000-07-26 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2005-08-15 Publication of UA73512C2 publication Critical patent/UA73512C2/uk

Links

238000000034 method Methods 0.000 title claims description 18
239000000203 mixture Substances 0.000 title description 83
238000002360 preparation method Methods 0.000 title description 2
108010063483 Streptogramin Group A Proteins 0.000 claims abstract description 10
108010063479 Streptogramin Group B Proteins 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims description 163
-1 C--C8-alkyl Chemical group 0.000 claims description 91
150000003254 radicals Chemical class 0.000 claims description 75
229920006395 saturated elastomer Polymers 0.000 claims description 70
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
229910052757 nitrogen Inorganic materials 0.000 claims description 42
108010034396 Streptogramins Proteins 0.000 claims description 35
125000000623 heterocyclic group Chemical group 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 27
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
125000005842 heteroatom Chemical group 0.000 claims description 26
229910052760 oxygen Chemical group 0.000 claims description 26
239000001301 oxygen Chemical group 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
229910052717 sulfur Inorganic materials 0.000 claims description 26
239000011593 sulfur Chemical group 0.000 claims description 26
229960003961 pristinamycin Drugs 0.000 claims description 24
108010079780 Pristinamycin Proteins 0.000 claims description 23
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 23
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 23
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 23
125000005843 halogen group Chemical group 0.000 claims description 22
238000004587 chromatography analysis Methods 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
125000004663 dialkyl amino 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
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
125000003884 phenylalkyl group Chemical group 0.000 claims description 10
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
229940041030 streptogramins Drugs 0.000 claims description 6
125000004001 thioalkyl group Chemical group 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 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
125000004122 cyclic group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 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
229910052740 iodine Inorganic materials 0.000 claims description 4
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
239000012025 fluorinating agent Substances 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000004953 trihalomethyl group Chemical group 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
NYAZXHASVIWIRJ-UHFFFAOYSA-N nitridosulfidocarbon(.) Chemical compound [S]C#N NYAZXHASVIWIRJ-UHFFFAOYSA-N 0.000 claims description 2
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 7
238000002955 isolation Methods 0.000 claims 2
230000009466 transformation Effects 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
244000257739 Dioscorea bulbifera Species 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
150000002391 heterocyclic compounds Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229940041022 streptomycins Drugs 0.000 claims 1
125000003396 thiol group Chemical class [H]S* 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 258
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 189
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
239000007787 solid Substances 0.000 description 107
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 92
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 56
239000003480 eluent Substances 0.000 description 50
239000000741 silica gel Substances 0.000 description 50
229910002027 silica gel Inorganic materials 0.000 description 50
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
229960001866 silicon dioxide Drugs 0.000 description 49
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
239000011541 reaction mixture Substances 0.000 description 39
239000000126 substance Substances 0.000 description 39
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 34
239000012074 organic phase Substances 0.000 description 34
239000007864 aqueous solution Substances 0.000 description 33
235000017557 sodium bicarbonate Nutrition 0.000 description 33
229910000030 sodium bicarbonate Inorganic materials 0.000 description 33
239000000047 product Substances 0.000 description 31
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
230000015572 biosynthetic process Effects 0.000 description 30
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
238000002844 melting Methods 0.000 description 29
230000008018 melting Effects 0.000 description 29
239000008346 aqueous phase Substances 0.000 description 27
239000000243 solution Substances 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
229910052938 sodium sulfate Inorganic materials 0.000 description 25
235000011152 sodium sulphate Nutrition 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
MVTQIFVKRXBCHS-SMMNFGSLSA-N N-[(3S,6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone Chemical compound CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c2coc(CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@H]1C)n2.CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]2CC(=O)CCN2C(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H]2CCCN2C1=O)c1ccccc1 MVTQIFVKRXBCHS-SMMNFGSLSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
239000002244 precipitate Substances 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
239000012265 solid product Substances 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 11
239000002904 solvent Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
239000013078 crystal Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
239000012043 crude product Substances 0.000 description 7
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 7
238000002953 preparative HPLC Methods 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 6
230000008859 change Effects 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000012047 saturated solution Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 5
239000002585 base Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
239000011575 calcium Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
229910052741 iridium Inorganic materials 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
150000001540 azides Chemical class 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
239000003795 chemical substances by application Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
JMTFRQZEUVQLRL-ZETCQYMHSA-N C(C)(=O)N[C@H](C(=O)NCC#CBr)CC(=O)N Chemical compound C(C)(=O)N[C@H](C(=O)NCC#CBr)CC(=O)N JMTFRQZEUVQLRL-ZETCQYMHSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
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239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
229960003085 meticillin Drugs 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
BNTFCVMJHBNJAR-UHFFFAOYSA-N n,n-diethyl-1,1,2,3,3,3-hexafluoropropan-1-amine Chemical compound CCN(CC)C(F)(F)C(F)C(F)(F)F BNTFCVMJHBNJAR-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
238000004651 near-field scanning optical microscopy Methods 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase 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
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
YGXCETJZBDTKRY-DZCVGBHJSA-N pristinamycin IA Chemical compound 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 YGXCETJZBDTKRY-DZCVGBHJSA-N 0.000 description 1
230000008569 process Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 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
239000006215 rectal suppository Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229960004029 silicic acid Drugs 0.000 description 1
229910052708 sodium Inorganic materials 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
239000011877 solvent mixture Substances 0.000 description 1
239000004071 soot Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical class 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 1
125000001424 substituent group Chemical group 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
229960000909 sulfur hexafluoride Drugs 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 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
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 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
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- 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
- 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)
Bioinformatics & Cheminformatics (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (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)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines Containing Plant Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UA2002010570A 1999-07-27 2000-07-26 Streptogramines derivatives, a method for the preparation thereof and composition based thereon UA73512C2 (en)

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 (1)

Publication Number	Publication Date
UA73512C2 true UA73512C2 (en)	2005-08-15

Family

ID=9548546

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002010570A UA73512C2 (en)	1999-07-27	2000-07-26	Streptogramines derivatives, a method for the preparation thereof and composition based thereon

Country Status (38)

Country	Link
US (1)	US6541451B1 (de)
EP (1)	EP1204675B1 (de)
JP (1)	JP4326178B2 (de)
KR (3)	KR20080077414A (de)
CN (1)	CN1360592B (de)
AP (1)	AP1376A (de)
AR (1)	AR024937A1 (de)
AT (1)	ATE240970T1 (de)
AU (1)	AU778033B2 (de)
BG (1)	BG65108B1 (de)
BR (1)	BR0012761B1 (de)
CA (1)	CA2380305C (de)
CL (1)	CL2004001094A1 (de)
CZ (1)	CZ2002227A3 (de)
DE (1)	DE60002891T2 (de)
DK (1)	DK1204675T3 (de)
DZ (1)	DZ3204A1 (de)
EA (1)	EA004297B1 (de)
EE (1)	EE05038B1 (de)
ES (1)	ES2199855T3 (de)
FR (1)	FR2796949B1 (de)
GE (1)	GEP20063973B (de)
HR (1)	HRP20020047B1 (de)
HU (1)	HUP0202594A3 (de)
IL (2)	IL146812A0 (de)
MA (1)	MA26809A1 (de)
MX (1)	MXPA02000319A (de)
NO (1)	NO328544B1 (de)
NZ (1)	NZ516621A (de)
OA (1)	OA11996A (de)
PL (1)	PL201854B1 (de)
PT (1)	PT1204675E (de)
RS (1)	RS50384B (de)
SK (1)	SK1132002A3 (de)
TN (1)	TNSN00164A1 (de)
UA (1)	UA73512C2 (de)
WO (1)	WO2001010895A1 (de)
ZA (1)	ZA200200312B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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 (de)	2020-05-27	2023-04-05	Università Degli Studi Di Trento	Neue therapie zur behandlung von tumoren

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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 PT PT00958620T patent/PT1204675E/pt unknown
- 2000-07-26 IL IL14681200A patent/IL146812A0/xx unknown
- 2000-07-26 AP APAP/P/2002/002402A patent/AP1376A/en active
- 2000-07-26 SK SK113-2002A patent/SK1132002A3/sk unknown
- 2000-07-26 CZ CZ2002227A patent/CZ2002227A3/cs unknown
- 2000-07-26 ES ES00958620T patent/ES2199855T3/es not_active Expired - Lifetime
- 2000-07-26 KR KR1020087019597A patent/KR20080077414A/ko not_active Ceased
- 2000-07-26 TN TNTNSN00164A patent/TNSN00164A1/fr unknown
- 2000-07-26 RS YUP-53/02A patent/RS50384B/sr unknown
- 2000-07-26 KR KR1020077012826A patent/KR20070067244A/ko not_active Ceased
- 2000-07-26 BR BRPI0012761-2A patent/BR0012761B1/pt not_active IP Right Cessation
- 2000-07-26 HU HU0202594A patent/HUP0202594A3/hu unknown
- 2000-07-26 CN CN008101833A patent/CN1360592B/zh not_active Expired - Fee Related
- 2000-07-26 MX MXPA02000319A patent/MXPA02000319A/es active IP Right Grant
- 2000-07-26 DK DK00958620T patent/DK1204675T3/da active
- 2000-07-26 GE GE4723A patent/GEP20063973B/en unknown
- 2000-07-26 EA EA200200197A patent/EA004297B1/ru not_active IP Right Cessation
- 2000-07-26 OA OA1200200023A patent/OA11996A/fr unknown
- 2000-07-26 HR HR20020047A patent/HRP20020047B1/xx not_active IP Right Cessation
- 2000-07-26 JP JP2001515703A patent/JP4326178B2/ja not_active Expired - Fee Related
- 2000-07-26 AT AT00958620T patent/ATE240970T1/de active
- 2000-07-26 WO PCT/FR2000/002146 patent/WO2001010895A1/fr not_active Ceased
- 2000-07-26 EE EEP200200043A patent/EE05038B1/xx not_active IP Right Cessation
- 2000-07-26 NZ NZ516621A patent/NZ516621A/en not_active IP Right Cessation
- 2000-07-26 AU AU70083/00A patent/AU778033B2/en not_active Ceased
- 2000-07-26 EP EP00958620A patent/EP1204675B1/de not_active Expired - Lifetime
- 2000-07-26 DZ DZ003204A patent/DZ3204A1/xx active
- 2000-07-26 PL PL353306A patent/PL201854B1/pl not_active IP Right Cessation
- 2000-07-26 KR KR1020027001046A patent/KR100824479B1/ko not_active Expired - Fee Related
- 2000-07-26 DE DE60002891T patent/DE60002891T2/de not_active Expired - Lifetime
- 2000-07-26 UA UA2002010570A patent/UA73512C2/uk unknown
- 2000-07-26 CA CA2380305A patent/CA2380305C/fr not_active Expired - Fee Related
- 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
- 2002-01-21 MA MA26493A patent/MA26809A1/fr unknown
- 2002-01-25 NO NO20020404A patent/NO328544B1/no not_active IP Right Cessation
- 2002-01-25 BG BG106352A patent/BG65108B1/bg unknown
2004
- 2004-05-18 CL CL200401094A patent/CL2004001094A1/es unknown

Also Published As

Publication number	Publication date
BR0012761A (pt)	2002-04-02
JP4326178B2 (ja)	2009-09-02
GEP20063973B (en)	2006-11-27
FR2796949A1 (fr)	2001-02-02
DK1204675T3 (da)	2003-09-15
NO328544B1 (no)	2010-03-15
NO20020404L (no)	2002-03-21
HRP20020047B1 (en)	2005-08-31
AU7008300A (en)	2001-03-05
TNSN00164A1 (fr)	2002-05-30
BR0012761B1 (pt)	2015-03-10
BG65108B1 (bg)	2007-02-28
SK1132002A3 (en)	2002-06-04
EA200200197A1 (ru)	2002-06-27
KR20080077414A (ko)	2008-08-22
AP2002002402A0 (en)	2002-03-31
AR024937A1 (es)	2002-10-30
US6541451B1 (en)	2003-04-01
KR20070067244A (ko)	2007-06-27
PL353306A1 (en)	2003-11-17
RS50384B (sr)	2009-12-31
DZ3204A1 (fr)	2001-02-15
HK1047114A1 (zh)	2003-02-07
AU778033B2 (en)	2004-11-11
CZ2002227A3 (cs)	2002-09-11
IL146812A (en)	2009-07-20
BG106352A (en)	2002-09-30
AP1376A (en)	2005-03-11
PL201854B1 (pl)	2009-05-29
EP1204675B1 (de)	2003-05-21
EE05038B1 (et)	2008-06-16
EP1204675A1 (de)	2002-05-15
MA26809A1 (fr)	2004-12-20
CA2380305C (fr)	2011-06-28
EE200200043A (et)	2003-04-15
CN1360592B (zh)	2010-04-14
HUP0202594A2 (hu)	2002-11-28
NO20020404D0 (no)	2002-01-25
ES2199855T3 (es)	2004-03-01
KR100824479B1 (ko)	2008-04-22
ATE240970T1 (de)	2003-06-15
PT1204675E (pt)	2003-10-31
CN1360592A (zh)	2002-07-24
KR20020015718A (ko)	2002-02-28
FR2796949B1 (fr)	2001-09-21
HUP0202594A3 (en)	2003-10-28
CL2004001094A1 (es)	2005-06-03
HRP20020047A2 (en)	2003-12-31
YU5302A (sh)	2006-05-25
ZA200200312B (en)	2003-06-25
NZ516621A (en)	2004-07-30
IL146812A0 (en)	2002-07-25
WO2001010895A1 (fr)	2001-02-15
CA2380305A1 (fr)	2001-02-15
MXPA02000319A (es)	2002-06-21
OA11996A (fr)	2006-04-18
JP2003532625A (ja)	2003-11-05
EA004297B1 (ru)	2004-02-26
DE60002891D1 (de)	2003-06-26
DE60002891T2 (de)	2004-03-11

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