NO329456B1 - Streptograminderivater, deres fremstilling samt preparater inneholdende derivatene - Google Patents

Streptograminderivater, deres fremstilling samt preparater inneholdende derivatene Download PDF

Info

Publication number: NO329456B1
Authority: NO; Norway
Prior art keywords: residue; alkyl; fluoro; pristinamycin; substituted
Prior art date: 1999-06-30

Application number

NO20016247A

Other languages

English (en)

Norwegian (no)

Other versions

NO20016247L (no

NO20016247D0 (no

Inventor

Serge Grisoni

Eric Bacque

Jean-Claude Barriere

Jean Bouquerel

Baptiste Ronan

Yves Ribeill

Pascal Desmazeau

Jean-Pierre Leconte

Daniel Achard

Original Assignee

Novexel

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.)

1999-06-30

Filing date

2001-12-19

Publication date

2010-10-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9547496&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO329456(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-12-19 Application filed by Novexel filed Critical Novexel

2001-12-19 Publication of NO20016247D0 publication Critical patent/NO20016247D0/no

2002-02-08 Publication of NO20016247L publication Critical patent/NO20016247L/no

2010-10-25 Publication of NO329456B1 publication Critical patent/NO329456B1/no

Links

108010034396 Streptogramins Proteins 0.000 title claims description 40
238000002360 preparation method Methods 0.000 title description 19
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 206
229960003961 pristinamycin Drugs 0.000 claims description 135
-1 cycloaliphatic Chemical group 0.000 claims description 71
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 62
125000000217 alkyl group Chemical group 0.000 claims description 59
229920006395 saturated elastomer Polymers 0.000 claims description 56
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 53
125000000623 heterocyclic group Chemical group 0.000 claims description 46
108010079780 Pristinamycin Proteins 0.000 claims description 44
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 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
125000003545 alkoxy group Chemical group 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 29
229940041030 streptogramins Drugs 0.000 claims description 22
125000004663 dialkyl amino group Chemical group 0.000 claims description 19
125000003282 alkyl amino group Chemical group 0.000 claims description 18
DFSJQGCLWZVMOD-IQIMCDJDSA-N flopristin Chemical group C1[C@H](F)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@@H](C)[C@@H](C(C)C)OC(=O)[C@H]2CCCN2C(=O)C2=COC1=N2 DFSJQGCLWZVMOD-IQIMCDJDSA-N 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
125000004414 alkyl thio group Chemical group 0.000 claims description 14
125000004001 thioalkyl group Chemical group 0.000 claims description 14
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
229910052760 oxygen Inorganic materials 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
229910052702 rhenium Inorganic materials 0.000 claims description 12
229910021481 rutherfordium Inorganic materials 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
125000004953 trihalomethyl group Chemical group 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 8
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 7
150000003254 radicals Chemical class 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
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 claims description 6
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
150000004820 halides Chemical class 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
150000004767 nitrides Chemical class 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 6
125000003884 phenylalkyl group Chemical group 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
230000009466 transformation Effects 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
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 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
PCOXSOQWQVRJCH-RIECGXCRSA-N efepristin Chemical compound N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(NC)=CC=2)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 PCOXSOQWQVRJCH-RIECGXCRSA-N 0.000 claims description 4
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
BYRKDHSWMQLYJB-UHFFFAOYSA-N pristinamycin IC Chemical compound CN1C(=O)C2CCCN2C(=O)C(C)NC(=O)C(NC(=O)C=2C(=CC=CN=2)O)C(C)OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C1CC1=CC=C(N(C)C)C=C1 BYRKDHSWMQLYJB-UHFFFAOYSA-N 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
229910052701 rubidium Inorganic materials 0.000 claims description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
PCOXSOQWQVRJCH-UHFFFAOYSA-N vernamycin-Bbeta Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(NC)=CC=2)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O PCOXSOQWQVRJCH-UHFFFAOYSA-N 0.000 claims description 4
LFOMGBBERKOUPQ-UHFFFAOYSA-N NS(F)(F)F Chemical compound NS(F)(F)F LFOMGBBERKOUPQ-UHFFFAOYSA-N 0.000 claims description 3
YGXCETJZBDTKRY-UHFFFAOYSA-N Pristinamycin Component I A 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)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-UHFFFAOYSA-N 0.000 claims description 3
108010015795 Streptogramin B Proteins 0.000 claims description 3
230000009471 action Effects 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
238000003682 fluorination reaction Methods 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
238000005658 halogenation reaction Methods 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
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 claims description 3
QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 claims description 3
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 3
UFXIRMVZNARBDL-UHFFFAOYSA-N trifluoro(morpholin-4-yl)-$l^{4}-sulfane Chemical compound FS(F)(F)N1CCOCC1 UFXIRMVZNARBDL-UHFFFAOYSA-N 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
BDZHKUAKSMWSAJ-UHFFFAOYSA-N 2-chloro-n,n-diethyl-1,1,2-trifluoroethanamine Chemical compound CCN(CC)C(F)(F)C(F)Cl BDZHKUAKSMWSAJ-UHFFFAOYSA-N 0.000 claims description 2
SATIISJKSAELDC-ZIOPZPSVSA-N 3-hydroxy-N-[(3R,6S,7R,10S,13S,16S,22R,24R)-24-hydroxy-7,11,13,17,20-pentamethyl-16-[(2S)-3-methylbutan-2-yl]-3-(2-methylpropyl)-2,5,9,12,15,18,21-heptaoxo-10-phenyl-8-oxa-1,4,11,14,17,20-hexazabicyclo[20.3.0]pentacosan-6-yl]pyridine-2-carboxamide Chemical compound CC(C)C[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](N(C)C(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)C(C)C)N(C)C(=O)CN(C)C(=O)[C@H]2C[C@@H](O)CN2C1=O)c1ccccc1 SATIISJKSAELDC-ZIOPZPSVSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
108010066860 Vernamycin B Proteins 0.000 claims description 2
108010080702 Virginiamycin Proteins 0.000 claims description 2
239000004188 Virginiamycin Substances 0.000 claims description 2
125000005042 acyloxymethyl group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000003983 crown ethers Chemical class 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
239000012025 fluorinating agent Substances 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
230000026030 halogenation Effects 0.000 claims description 2
125000004970 halomethyl group Chemical group 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
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 claims description 2
XMKLKZFSQXZUQU-UHFFFAOYSA-N neoviridogrisein-II Natural products CC1OC(=O)C(C=2C=CC=CC=2)N(C)C(=O)C(C)NC(=O)C(C(C)C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(CC(C)C)NC(=O)C1NC(=O)C1=NC=CC=C1O XMKLKZFSQXZUQU-UHFFFAOYSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 claims description 2
229960000909 sulfur hexafluoride Drugs 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
229960003842 virginiamycin Drugs 0.000 claims description 2
235000019373 virginiamycin Nutrition 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
239000005864 Sulphur Substances 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
239000012374 esterification agent Substances 0.000 claims 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
229930014626 natural product Natural products 0.000 claims 1
125000004954 trialkylamino group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 672
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 279
239000007787 solid Substances 0.000 description 251
239000000243 solution Substances 0.000 description 228
238000003756 stirring Methods 0.000 description 196
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
108010015791 Streptogramin A Proteins 0.000 description 175
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 128
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 121
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 107
238000003818 flash chromatography Methods 0.000 description 92
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 91
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 85
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 84
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 84
239000011541 reaction mixture Substances 0.000 description 84
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
239000012074 organic phase Substances 0.000 description 75
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
229910052943 magnesium sulfate Inorganic materials 0.000 description 64
235000019341 magnesium sulphate Nutrition 0.000 description 64
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 60
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
238000002844 melting Methods 0.000 description 57
230000008018 melting Effects 0.000 description 57
238000001914 filtration Methods 0.000 description 56
238000000354 decomposition reaction Methods 0.000 description 53
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 51
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 51
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
238000001035 drying Methods 0.000 description 46
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
229910052786 argon Inorganic materials 0.000 description 42
239000003921 oil Substances 0.000 description 41
235000019198 oils Nutrition 0.000 description 41
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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
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
239000001384 succinic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository 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
150000003892 tartrate salts Chemical class 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
RSHBFZCIFFBTEW-UHFFFAOYSA-M tetrabutylazanium;thiocyanate Chemical compound [S-]C#N.CCCC[N+](CCCC)(CCCC)CCCC RSHBFZCIFFBTEW-UHFFFAOYSA-M 0.000 description 1
BXWPWVMXHSWPGZ-UHFFFAOYSA-N tetracyclohexylazanium Chemical compound C1CCCCC1[N+](C1CCCCC1)(C1CCCCC1)C1CCCCC1 BXWPWVMXHSWPGZ-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-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
238000004809 thin layer chromatography Methods 0.000 description 1
150000003567 thiocyanates Chemical class 0.000 description 1
125000000858 thiocyanato group Chemical group *SC#N 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
125000004665 trialkylsilyl group Chemical group 0.000 description 1
HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
239000002966 varnish Substances 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000012712 vegetable carbon Nutrition 0.000 description 1
239000004108 vegetable carbon Substances 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 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
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/15—Depsipeptides; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06182—Dipeptides with the first amino acid being heterocyclic and Pristinamycin II; Derivatives thereof

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Organic Chemistry (AREA)
Immunology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Gastroenterology & Hepatology (AREA)
Epidemiology (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Saccharide Compounds (AREA)

NO20016247A 1999-06-30 2001-12-19 Streptograminderivater, deres fremstilling samt preparater inneholdende derivatene NO329456B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9908375A FR2795733B1 (fr)	1999-06-30	1999-06-30	Derives de streptogramines, leur preparation et les compositions qui les contiennent
PCT/FR2000/001818 WO2001002427A1 (fr)	1999-06-30	2000-06-29	Derives de streptogramines, leur preparation et les compositions qui les contiennent

Publications (3)

Publication Number	Publication Date
NO20016247D0 NO20016247D0 (no)	2001-12-19
NO20016247L NO20016247L (no)	2002-02-08
NO329456B1 true NO329456B1 (no)	2010-10-25

Family

ID=9547496

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20016247A NO329456B1 (no)	1999-06-30	2001-12-19	Streptograminderivater, deres fremstilling samt preparater inneholdende derivatene

Country Status (37)

Country	Link
US (2)	US6569854B1 (et)
EP (1)	EP1187847B1 (et)
JP (1)	JP4585728B2 (et)
KR (1)	KR100742035B1 (et)
CN (2)	CN100543032C (et)
AP (1)	AP1392A (et)
AR (2)	AR029758A1 (et)
AT (1)	ATE255592T1 (et)
AU (1)	AU781923B2 (et)
BG (1)	BG65786B1 (et)
BR (1)	BRPI0012032B1 (et)
CA (1)	CA2376698C (et)
CZ (1)	CZ301048B6 (et)
DE (1)	DE60006958T2 (et)
DK (1)	DK1187847T3 (et)
EA (1)	EA005199B1 (et)
EE (1)	EE04683B1 (et)
ES (1)	ES2207535T3 (et)
FR (1)	FR2795733B1 (et)
GE (1)	GEP20063972B (et)
HR (1)	HRP20010937B1 (et)
HU (1)	HUP0201692A3 (et)
IL (2)	IL146185A0 (et)
MA (1)	MA26802A1 (et)
MX (1)	MXPA01012807A (et)
NO (1)	NO329456B1 (et)
NZ (1)	NZ516100A (et)
OA (1)	OA11979A (et)
PT (1)	PT1187847E (et)
RS (1)	RS50138B (et)
SI (1)	SI1187847T1 (et)
SK (1)	SK285605B6 (et)
TN (1)	TNSN00145A1 (et)
TR (1)	TR200103829T2 (et)
UA (1)	UA71619C2 (et)
WO (1)	WO2001002427A1 (et)
ZA (1)	ZA200110150B (et)

Families Citing this family (16)

* 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
FR2795733B1 (fr) *	1999-06-30	2001-09-07	Aventis Pharma Sa	Derives de streptogramines, leur preparation et les compositions 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
US7488747B2 (en)	2003-12-29	2009-02-10	Sepracor Inc.	Pyrrole and pyrazole DAAO inhibitors
US7565200B2 (en) *	2004-11-12	2009-07-21	Advanced Neuromodulation Systems, Inc.	Systems and methods for selecting stimulation sites and applying treatment, including treatment of symptoms of Parkinson's disease, other movement disorders, and/or drug side effects
CN101394847B (zh)	2006-01-06	2017-05-24	塞普拉柯公司	作为单胺重摄取抑制剂的环烷基胺类
CA2636275C (en)	2006-01-06	2013-02-12	Sepracor Inc.	Tetralone-based monoamine reuptake inhibitors
JP5377285B2 (ja)	2006-03-31	2013-12-25	サノビオンファーマシューティカルズインク	キラルアミドおよびキラルアミンの調製
US7884124B2 (en)	2006-06-30	2011-02-08	Sepracor Inc.	Fluoro-substituted inhibitors of D-amino acid oxidase
US7902252B2 (en)	2007-01-18	2011-03-08	Sepracor, Inc.	Inhibitors of D-amino acid oxidase
CN103936605B (zh)	2007-05-31	2017-09-01	赛诺维信制药公司	苯基取代的环烷胺作为一元胺再摄取抑制剂
CN103508981A (zh) *	2012-06-18	2014-01-15	北京美倍他药物研究有限公司	新的哌嗪衍生物及其医药用途
CA3070851A1 (en) *	2017-08-01	2019-02-07	The Regents Of The University Of California	Methods of making streptogramin compositions and the use thereof
KR102107659B1 (ko)	2018-12-07	2020-05-07	경상대학교 산학협력단	Mmagnu1 화합물을 유효성분으로 함유하는 결핵균 또는 비결핵 항산균 감염 질환 예방 또는 치료용 조성물
AU2021279243A1 (en)	2020-05-27	2023-01-05	Fondazione Giovanni Celeghin - Onlus	New therapy for the treatment of tumors

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2549065B1 (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
BE1001013A4 (fr) *	1987-10-22	1989-06-13	Icp Internat Inst Of Cellular	Derives de synergimycines de types a et b, procede pour leur preparation et utilisation de ceux-ci.
IL121821A (en) *	1993-02-17	2000-02-17	Rhone Poulenc Rorer Sa	Process for purifying a group A minority component of streptogramin some such purified components and their uses
FR2766489B1 (fr) *	1997-07-28	1999-08-27	Rhone Poulenc Rorer Sa	Derives de streptogramines, leur preparation et les compositions qui les contiennent
FR2795733B1 (fr) *	1999-06-30	2001-09-07	Aventis Pharma Sa	Derives de streptogramines, leur preparation et les compositions qui les contiennent

1999
- 1999-06-30 FR FR9908375A patent/FR2795733B1/fr not_active Expired - Fee Related
2000
- 2000-06-29 DK DK00949570T patent/DK1187847T3/da active
- 2000-06-29 UA UA2001128962A patent/UA71619C2/uk unknown
- 2000-06-29 SI SI200030278T patent/SI1187847T1/xx unknown
- 2000-06-29 TR TR2001/03829T patent/TR200103829T2/xx unknown
- 2000-06-29 JP JP2001507863A patent/JP4585728B2/ja not_active Expired - Fee Related
- 2000-06-29 CN CNB008095965A patent/CN100543032C/zh not_active Expired - Fee Related
- 2000-06-29 ES ES00949570T patent/ES2207535T3/es not_active Expired - Lifetime
- 2000-06-29 GE GE4674A patent/GEP20063972B/en unknown
- 2000-06-29 CN CNA2005100755816A patent/CN1961878A/zh active Pending
- 2000-06-29 NZ NZ516100A patent/NZ516100A/xx not_active IP Right Cessation
- 2000-06-29 DE DE60006958T patent/DE60006958T2/de not_active Expired - Lifetime
- 2000-06-29 IL IL14618500A patent/IL146185A0/xx active IP Right Grant
- 2000-06-29 AT AT00949570T patent/ATE255592T1/de active
- 2000-06-29 AU AU62886/00A patent/AU781923B2/en not_active Ceased
- 2000-06-29 WO PCT/FR2000/001818 patent/WO2001002427A1/fr active IP Right Grant
- 2000-06-29 CZ CZ20014641A patent/CZ301048B6/cs not_active IP Right Cessation
- 2000-06-29 CA CA2376698A patent/CA2376698C/fr not_active Expired - Fee Related
- 2000-06-29 KR KR1020017016856A patent/KR100742035B1/ko not_active IP Right Cessation
- 2000-06-29 EA EA200200108A patent/EA005199B1/ru not_active IP Right Cessation
- 2000-06-29 EP EP00949570A patent/EP1187847B1/fr not_active Expired - Lifetime
- 2000-06-29 SK SK1930-2001A patent/SK285605B6/sk not_active IP Right Cessation
- 2000-06-29 AP APAP/P/2001/002371A patent/AP1392A/en active
- 2000-06-29 EE EEP200100706A patent/EE04683B1/et not_active IP Right Cessation
- 2000-06-29 OA OA1200100346A patent/OA11979A/fr unknown
- 2000-06-29 PT PT00949570T patent/PT1187847E/pt unknown
- 2000-06-29 BR BRPI0012032-4A patent/BRPI0012032B1/pt not_active IP Right Cessation
- 2000-06-29 HU HU0201692A patent/HUP0201692A3/hu unknown
- 2000-06-29 TN TNTNSN00145A patent/TNSN00145A1/fr unknown
- 2000-06-29 MX MXPA01012807A patent/MXPA01012807A/es active IP Right Grant
- 2000-06-30 US US09/609,717 patent/US6569854B1/en not_active Expired - Lifetime
- 2000-06-30 AR ARP000103367A patent/AR029758A1/es active IP Right Grant
- 2000-07-29 RS YUP-895/01A patent/RS50138B/sr unknown
2001
- 2001-10-25 IL IL146185A patent/IL146185A/en not_active IP Right Cessation
- 2001-12-10 ZA ZA200110150A patent/ZA200110150B/xx unknown
- 2001-12-19 NO NO20016247A patent/NO329456B1/no not_active IP Right Cessation
- 2001-12-19 BG BG106235A patent/BG65786B1/bg unknown
- 2001-12-20 HR HR20010937A patent/HRP20010937B1/xx not_active IP Right Cessation
- 2001-12-27 MA MA26453A patent/MA26802A1/fr unknown
2002
- 2002-12-06 US US10/310,773 patent/US7166594B2/en not_active Expired - Fee Related
2008
- 2008-06-06 AR ARP080102448A patent/AR066926A2/es unknown

Also Published As

Publication number	Publication date
AR029758A1 (es)	2003-07-16
CA2376698A1 (fr)	2001-01-11
FR2795733A1 (fr)	2001-01-05
DE60006958D1 (de)	2004-01-15
EE04683B1 (et)	2006-08-15
EP1187847B1 (fr)	2003-12-03
CN100543032C (zh)	2009-09-23
UA71619C2 (uk)	2004-12-15
ZA200110150B (en)	2003-03-10
EE200100706A (et)	2003-04-15
HRP20010937A2 (en)	2003-08-31
KR20020020763A (ko)	2002-03-15
DK1187847T3 (da)	2004-01-05
US20030149004A1 (en)	2003-08-07
RS50138B (sr)	2009-03-25
CN1961878A (zh)	2007-05-16
YU89501A (sh)	2004-05-12
MA26802A1 (fr)	2004-12-20
TR200103829T2 (tr)	2002-04-22
OA11979A (fr)	2006-04-18
NZ516100A (en)	2004-01-30
DE60006958T2 (de)	2004-10-21
HUP0201692A3 (en)	2002-10-28
JP4585728B2 (ja)	2010-11-24
AR066926A2 (es)	2009-09-23
EP1187847A1 (fr)	2002-03-20
BG65786B1 (bg)	2009-11-30
EA200200108A1 (ru)	2002-06-27
KR100742035B1 (ko)	2007-07-23
HUP0201692A2 (en)	2002-09-28
IL146185A0 (en)	2002-07-25
SK285605B6 (sk)	2007-04-05
CZ20014641A3 (cs)	2002-04-17
CN1358194A (zh)	2002-07-10
IL146185A (en)	2007-08-19
ES2207535T3 (es)	2004-06-01
PT1187847E (pt)	2004-04-30
BRPI0012032B1 (pt)	2015-06-30
WO2001002427A1 (fr)	2001-01-11
BG106235A (en)	2002-08-30
AP2001002371A0 (en)	2001-12-31
SI1187847T1 (en)	2004-04-30
GEP20063972B (en)	2006-11-27
CA2376698C (fr)	2013-05-14
ATE255592T1 (de)	2003-12-15
AU6288600A (en)	2001-01-22
US7166594B2 (en)	2007-01-23
NO20016247L (no)	2002-02-08
NO20016247D0 (no)	2001-12-19
AP1392A (en)	2005-04-15
AU781923B2 (en)	2005-06-23
MXPA01012807A (es)	2002-07-22
HRP20010937B1 (en)	2005-02-28
PL352781A1 (en)	2003-09-08
CZ301048B6 (cs)	2009-10-21
FR2795733B1 (fr)	2001-09-07
JP2003503509A (ja)	2003-01-28
BR0012032A (pt)	2002-03-19
TNSN00145A1 (fr)	2002-05-30
EA005199B1 (ru)	2004-12-30
US6569854B1 (en)	2003-05-27
SK19302001A3 (sk)	2002-07-02

Publication	Publication Date	Title
NO329456B1 (no)	2010-10-25	Streptograminderivater, deres fremstilling samt preparater inneholdende derivatene
EP1064298B1 (en)	2008-10-08	Inhibitors of caspases
KR100824479B1 (ko)	2008-04-22	스트렙토그라민 유도체, 이의 제조방법 및 이를 함유하는조성물
US6596717B2 (en)	2003-07-22	Streptogramin derivatives, their preparation and compositions which contain them
PL203554B1 (pl)	2009-10-30	Pochodna streptograminy z grupy A, sposób wytwarzania pochodnej streptograminy z grupy A oraz kompozycja farmaceutyczna zawieraj aca pochodn a streptograminy z grupy A
JP4282323B2 (ja)	2009-06-17	ストレプトグラミン誘導体、その製造およびそれを含有する組成物
JP4225377B2 (ja)	2009-02-18	ストレプトグラミン誘導体、その製造およびそれを含有する組成物

Legal Events

Date	Code	Title	Description
2013-02-04	MM1K	Lapsed by not paying the annual fees