AU2004261550A1 - Novel lincomycin derivatives possessing antimicrobial activity - Google Patents
Novel lincomycin derivatives possessing antimicrobial activity Download PDFInfo
- Publication number
- AU2004261550A1 AU2004261550A1 AU2004261550A AU2004261550A AU2004261550A1 AU 2004261550 A1 AU2004261550 A1 AU 2004261550A1 AU 2004261550 A AU2004261550 A AU 2004261550A AU 2004261550 A AU2004261550 A AU 2004261550A AU 2004261550 A1 AU2004261550 A1 AU 2004261550A1
- Authority
- AU
- Australia
- Prior art keywords
- propyl
- tetrahydro
- pyran
- trihydroxy
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical class CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 title description 17
- 230000000845 anti-microbial effect Effects 0.000 title description 4
- -1 p-dichlorophenyl Chemical group 0.000 claims description 343
- 125000000217 alkyl group Chemical group 0.000 claims description 300
- 229910052739 hydrogen Inorganic materials 0.000 claims description 186
- 239000001257 hydrogen Substances 0.000 claims description 185
- 150000001875 compounds Chemical class 0.000 claims description 173
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 141
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 128
- 125000004414 alkyl thio group Chemical group 0.000 claims description 101
- 239000000203 mixture Substances 0.000 claims description 93
- 125000003342 alkenyl group Chemical group 0.000 claims description 92
- 125000005843 halogen group Chemical group 0.000 claims description 89
- 125000001072 heteroaryl group Chemical group 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 78
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 78
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 46
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 43
- 125000001153 fluoro group Chemical group F* 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 239000001301 oxygen Substances 0.000 claims description 40
- 125000003107 substituted aryl group Chemical group 0.000 claims description 37
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 33
- 239000000651 prodrug Substances 0.000 claims description 31
- 229940002612 prodrug Drugs 0.000 claims description 31
- FYEFLEUMNQBKHG-UHFFFAOYSA-N 2-(1-amino-2-methylpropyl)-6-methylsulfanyloxane-3,4,5-triol Chemical compound CSC1OC(C(N)C(C)C)C(O)C(O)C1O FYEFLEUMNQBKHG-UHFFFAOYSA-N 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 241000124008 Mammalia Species 0.000 claims description 26
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 26
- 150000002829 nitrogen Chemical class 0.000 claims description 26
- 150000002926 oxygen Chemical class 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 208000015181 infectious disease Diseases 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 229910020008 S(O) Inorganic materials 0.000 claims description 17
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 16
- 150000001409 amidines Chemical class 0.000 claims description 16
- 239000012634 fragment Substances 0.000 claims description 16
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 12
- 125000004001 thioalkyl group Chemical group 0.000 claims description 12
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 11
- NJIGWPJQQDNCKQ-UHFFFAOYSA-N 4-fluoro-4-propylpyrrolidine-2-carboxylic acid Chemical compound CCCC1(F)CNC(C(O)=O)C1 NJIGWPJQQDNCKQ-UHFFFAOYSA-N 0.000 claims description 10
- QSWMXBBKOQVGOX-UHFFFAOYSA-N 4-fluoro-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)(F)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 QSWMXBBKOQVGOX-UHFFFAOYSA-N 0.000 claims description 10
- 241000606768 Haemophilus influenzae Species 0.000 claims description 10
- 125000005518 carboxamido group Chemical group 0.000 claims description 10
- 230000000813 microbial effect Effects 0.000 claims description 10
- DNSDOTXFVIOTHM-UHFFFAOYSA-N 4-(3-imidazol-1-ylpropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCN2C=NC=C2)C1 DNSDOTXFVIOTHM-UHFFFAOYSA-N 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 229940047650 haemophilus influenzae Drugs 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 229910003827 NRaRb Inorganic materials 0.000 claims description 8
- 235000021314 Palmitic acid Nutrition 0.000 claims description 8
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 8
- AEEIMWYSDWZKAT-UHFFFAOYSA-N 2-(1-amino-2-hydroxypropyl)-6-methylsulfanyloxane-3,4,5-triol Chemical compound CSC1OC(C(N)C(C)O)C(O)C(O)C1O AEEIMWYSDWZKAT-UHFFFAOYSA-N 0.000 claims description 7
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 7
- 101150065749 Churc1 gene Proteins 0.000 claims description 7
- 241000194032 Enterococcus faecalis Species 0.000 claims description 7
- 241000194031 Enterococcus faecium Species 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
- 102100038239 Protein Churchill Human genes 0.000 claims description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
- 230000037396 body weight Effects 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 6
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
- 150000003141 primary amines Chemical class 0.000 claims description 6
- LMYKEXDWFJPOPP-UHFFFAOYSA-N 1-(1h-imidazol-2-ylmethyl)-4-pentylpyrrolidine-2-carboxylic acid Chemical compound C1C(CCCCC)CC(C(O)=O)N1CC1=NC=CN1 LMYKEXDWFJPOPP-UHFFFAOYSA-N 0.000 claims description 5
- MFRNJOFFXJVNGY-UHFFFAOYSA-N 1-(2-amino-2-oxoethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound NC(=O)CN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 MFRNJOFFXJVNGY-UHFFFAOYSA-N 0.000 claims description 5
- CVIFYQUYQFXVDZ-UHFFFAOYSA-N 1-(2-aminoethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound NCCN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 CVIFYQUYQFXVDZ-UHFFFAOYSA-N 0.000 claims description 5
- UMLHDABYMANNEV-UHFFFAOYSA-N 1-(2-methoxyethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound COCCN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 UMLHDABYMANNEV-UHFFFAOYSA-N 0.000 claims description 5
- ORHUTNZUHATDOA-UHFFFAOYSA-N 4-(3-cyanopropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCC#N)C1 ORHUTNZUHATDOA-UHFFFAOYSA-N 0.000 claims description 5
- ZLAXTLUWJXUNMJ-UHFFFAOYSA-N 4-butylsulfanyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound C1C(SCCCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 ZLAXTLUWJXUNMJ-UHFFFAOYSA-N 0.000 claims description 5
- MKTSNRNWQWWNBS-UHFFFAOYSA-N 4-fluoro-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpiperidine-2-carboxamide Chemical compound C1C(CCC)(F)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 MKTSNRNWQWWNBS-UHFFFAOYSA-N 0.000 claims description 5
- DQHUOKOFSXEEAW-UHFFFAOYSA-N 4-propylpyrrolidin-1-ium-2-carboxylate Chemical compound CCCC1CNC(C(O)=O)C1 DQHUOKOFSXEEAW-UHFFFAOYSA-N 0.000 claims description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 5
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- QJGYZJVCWOMBJW-UHFFFAOYSA-N methyl 2-[2-[[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]carbamoyl]-4-pentylpyrrolidin-1-yl]acetate Chemical compound COC(=O)CN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 QJGYZJVCWOMBJW-UHFFFAOYSA-N 0.000 claims description 5
- GCBGCRVFIGNWLR-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(pyrazin-2-ylmethylsulfanyl)pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC=2N=CC=NC=2)C1 GCBGCRVFIGNWLR-UHFFFAOYSA-N 0.000 claims description 5
- QISPYBSUSXGYPY-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(pyridin-2-ylmethylsulfanyl)pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC=2N=CC=CC=2)C1 QISPYBSUSXGYPY-UHFFFAOYSA-N 0.000 claims description 5
- JYWRNFNQNIZOEQ-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(thiophen-2-ylmethylsulfanyl)pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC=2SC=CC=2)C1 JYWRNFNQNIZOEQ-UHFFFAOYSA-N 0.000 claims description 5
- HARUDSUZZMKALL-UHFFFAOYSA-N 1-(cyanomethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound N#CCN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 HARUDSUZZMKALL-UHFFFAOYSA-N 0.000 claims description 4
- WUYRBSXENHJOMH-UHFFFAOYSA-N 1-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpiperidine-2-carboxamide Chemical compound O1C(SC)C(O)C(O)C(O)C1C(C(C)C)NC(=O)C1CC(CCC)CCN1CC=1OC(=O)OC=1C WUYRBSXENHJOMH-UHFFFAOYSA-N 0.000 claims description 4
- BERAAJKLZUCLOQ-UHFFFAOYSA-N 1-methanimidoyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound N=CN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 BERAAJKLZUCLOQ-UHFFFAOYSA-N 0.000 claims description 4
- YXHXKZBXKLKBML-UHFFFAOYSA-N 4-(3-ethylsulfanylpropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CCCSCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 YXHXKZBXKLKBML-UHFFFAOYSA-N 0.000 claims description 4
- HDINUXUNJMXPJX-UHFFFAOYSA-N 4-[3-(furan-2-ylmethylsulfanyl)propyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCSCC=2OC=CC=2)C1 HDINUXUNJMXPJX-UHFFFAOYSA-N 0.000 claims description 4
- ZOGNUIUCLMYNTO-UHFFFAOYSA-N 4-propylpiperidine-2-carboxylic acid Chemical compound CCCC1CCNC(C(O)=O)C1 ZOGNUIUCLMYNTO-UHFFFAOYSA-N 0.000 claims description 4
- 241000606123 Bacteroides thetaiotaomicron Species 0.000 claims description 4
- 241000193163 Clostridioides difficile Species 0.000 claims description 4
- 241000191967 Staphylococcus aureus Species 0.000 claims description 4
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 4
- 241000193998 Streptococcus pneumoniae Species 0.000 claims description 4
- 229940032049 enterococcus faecalis Drugs 0.000 claims description 4
- UZRDREPVAWXHDU-UHFFFAOYSA-N ethyl 2-[[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]carbamoyl]-4-propylpiperidine-1-carboxylate Chemical compound C1C(CCC)CCN(C(=O)OCC)C1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 UZRDREPVAWXHDU-UHFFFAOYSA-N 0.000 claims description 4
- LOTXOLDKOMAKAY-UHFFFAOYSA-N n-[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-ethylsulfanylpyrrolidine-2-carboxamide Chemical compound C1C(SCC)CNC1C(=O)NC(C(C)Cl)C1C(O)C(O)C(O)C(SC)O1 LOTXOLDKOMAKAY-UHFFFAOYSA-N 0.000 claims description 4
- CIOSLAWOFPYTJD-UHFFFAOYSA-N n-[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propyl-1,2,3,6-tetrahydropyridine-2-carboxamide Chemical compound C1C(CCC)=CCNC1C(=O)NC(C(C)Cl)C1C(O)C(O)C(O)C(SC)O1 CIOSLAWOFPYTJD-UHFFFAOYSA-N 0.000 claims description 4
- BQABFQXRHPUTGW-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(3-pyridin-4-ylpropyl)pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCC(CCCC=2C=CN=CC=2)C1 BQABFQXRHPUTGW-UHFFFAOYSA-N 0.000 claims description 4
- UXIKMADAIRHBGI-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propyl-1,2,3,6-tetrahydropyridine-2-carboxamide Chemical compound C1C(CCC)=CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 UXIKMADAIRHBGI-UHFFFAOYSA-N 0.000 claims description 4
- HETSCOAYMHOHEH-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylidenepiperidine-2-carboxamide Chemical compound C1C(=CCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 HETSCOAYMHOHEH-UHFFFAOYSA-N 0.000 claims description 4
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 4
- UGGZVDLWLHNKNW-UHFFFAOYSA-N 1-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound C1C(CCCCC)CC(C(=O)NC(C(C)C)C2C(C(O)C(O)C(CCC)O2)O)N1CC=1OC(=O)OC=1C UGGZVDLWLHNKNW-UHFFFAOYSA-N 0.000 claims description 3
- BUYZXQSVHVDPON-UHFFFAOYSA-N 1-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)CC(C(=O)NC(C(C)C)C2C(C(O)C(O)C(CCC)O2)O)N1CC=1OC(=O)OC=1C BUYZXQSVHVDPON-UHFFFAOYSA-N 0.000 claims description 3
- UAHGURVACUUGBB-UHFFFAOYSA-N 4-(3-thiophen-2-ylsulfanylpropyl)piperidine-2-carboxylic acid Chemical compound C1CNC(C(=O)O)CC1CCCSC1=CC=CS1 UAHGURVACUUGBB-UHFFFAOYSA-N 0.000 claims description 3
- RIBVZRFRMBNDEX-UHFFFAOYSA-N 4-ethylsulfanyl-n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound C1C(SCC)CNC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 RIBVZRFRMBNDEX-UHFFFAOYSA-N 0.000 claims description 3
- 241000606124 Bacteroides fragilis Species 0.000 claims description 3
- 241000588724 Escherichia coli Species 0.000 claims description 3
- AZFCXGNLOCDOJB-UHFFFAOYSA-N [4,5-dihydroxy-6-[2-methyl-1-[(4-propylpyrrolidine-2-carbonyl)amino]propyl]-2-propyloxan-3-yl] dihydrogen phosphate Chemical compound C1C(CCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(OP(O)(O)=O)C(CCC)O1 AZFCXGNLOCDOJB-UHFFFAOYSA-N 0.000 claims description 3
- OUYYNZDOJHSQBW-UHFFFAOYSA-N cyanomethanimidamide Chemical compound NC(=N)C#N OUYYNZDOJHSQBW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- SFAPNAFXCFKSJI-UHFFFAOYSA-N n-[1-(6-butoxy-3,4,5-trihydroxyoxan-2-yl)-2-methylpropyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound C1C(CCCCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(OCCCC)O1 SFAPNAFXCFKSJI-UHFFFAOYSA-N 0.000 claims description 3
- MWFXOTFLZLDBEM-UHFFFAOYSA-N n-[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-fluoro-4-propylpiperidine-2-carboxamide Chemical compound C1C(CCC)(F)CCNC1C(=O)NC(C(C)Cl)C1C(O)C(O)C(O)C(SC)O1 MWFXOTFLZLDBEM-UHFFFAOYSA-N 0.000 claims description 3
- SZOJVKWLQWSYCL-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound C1C(CCCCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CCC)O1 SZOJVKWLQWSYCL-UHFFFAOYSA-N 0.000 claims description 3
- NSKMMGDLZOZZNL-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]-4-propylpiperidine-2-carboxamide Chemical compound C1C(CCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CCC)O1 NSKMMGDLZOZZNL-UHFFFAOYSA-N 0.000 claims description 3
- FRPCTAZJHCODMF-UHFFFAOYSA-N n-[2-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CO)O1 FRPCTAZJHCODMF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052705 radium Inorganic materials 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- WGSLYMHXZQYHCE-UHFFFAOYSA-N 1-(2-hydroxyethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound OCCN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CCC)O1 WGSLYMHXZQYHCE-UHFFFAOYSA-N 0.000 claims description 2
- AVQLXPWGFFXNKF-UHFFFAOYSA-N 4-(3-ethoxyiminopropyl)piperidine-2-carboxylic acid Chemical compound CCON=CCCC1CCNC(C(O)=O)C1 AVQLXPWGFFXNKF-UHFFFAOYSA-N 0.000 claims description 2
- VHDFWRRYDWHMAL-UHFFFAOYSA-N 4-(3-methoxyiminopropyl)piperidine-2-carboxylic acid Chemical compound CON=CCCC1CCNC(C(O)=O)C1 VHDFWRRYDWHMAL-UHFFFAOYSA-N 0.000 claims description 2
- BFZVMDXCWJWEIG-UHFFFAOYSA-N 4-[3-(furan-2-ylmethylsulfanyl)propyl]piperidine-2-carboxylic acid Chemical compound C1CNC(C(=O)O)CC1CCCSCC1=CC=CO1 BFZVMDXCWJWEIG-UHFFFAOYSA-N 0.000 claims description 2
- SWBGPJIGJIFMFZ-UHFFFAOYSA-N 4-pentylpyrrolidine-2-carboxylic acid Chemical compound CCCCCC1CNC(C(O)=O)C1 SWBGPJIGJIFMFZ-UHFFFAOYSA-N 0.000 claims description 2
- PJAIRCFEKPCWHY-UHFFFAOYSA-N [6-[2-chloro-1-[(4-fluoro-4-propylpiperidine-2-carbonyl)amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate Chemical compound C1C(CCC)(F)CCNC1C(=O)NC(C(C)Cl)C1C(O)C(O)C(OP(O)(O)=O)C(SC)O1 PJAIRCFEKPCWHY-UHFFFAOYSA-N 0.000 claims description 2
- SWLXTVSLIMVWFW-UHFFFAOYSA-N [6-[2-chloro-1-[[5-(cyclopropylmethyl)azepane-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate Chemical compound OC1C(O)C(OP(O)(O)=O)C(SC)OC1C(C(C)Cl)NC(=O)C1NCCC(CC2CC2)CC1 SWLXTVSLIMVWFW-UHFFFAOYSA-N 0.000 claims description 2
- HCFRXDXGDYLNKB-UHFFFAOYSA-N n-[1-[6-(cyclopropylmethyl)-3,4,5-trihydroxyoxan-2-yl]-2-methylpropyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CC2CC2)O1 HCFRXDXGDYLNKB-UHFFFAOYSA-N 0.000 claims description 2
- DZWARKMMNMLORV-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(3,3,3-trifluoropropylsulfanyl)pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCCC(F)(F)F)C1 DZWARKMMNMLORV-UHFFFAOYSA-N 0.000 claims description 2
- LMWCAOHYAYDOSH-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxyoxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound C1C(CCCCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)CO1 LMWCAOHYAYDOSH-UHFFFAOYSA-N 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 16
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- KOGLZVRPQJRCHE-UHFFFAOYSA-N phenyl 2-[[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]carbamoyl]-4-propylpiperidine-1-carboxylate Chemical compound C1C(CCC)CCN(C(=O)OC=2C=CC=CC=2)C1C(=O)NC(C(C)C)C1OC(SC)C(O)C(O)C1O KOGLZVRPQJRCHE-UHFFFAOYSA-N 0.000 claims 6
- UUHWQBMPDDOBFD-UHFFFAOYSA-N 4-[(2,4-dichlorophenyl)methylsulfanyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCC(SCC=2C(=CC(Cl)=CC=2)Cl)C1 UUHWQBMPDDOBFD-UHFFFAOYSA-N 0.000 claims 4
- LENXSCSKTOFZOG-UHFFFAOYSA-N 4-[(4-fluorophenyl)methylsulfanyl]-n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC=2C=CC(F)=CC=2)C1 LENXSCSKTOFZOG-UHFFFAOYSA-N 0.000 claims 4
- VMVKTZMYJAAJIR-UHFFFAOYSA-N 4-[2-(1,3-dithiolan-2-yl)ethyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCC2SCCS2)C1 VMVKTZMYJAAJIR-UHFFFAOYSA-N 0.000 claims 4
- CVROZZFVFAXTKC-UHFFFAOYSA-N 4-[2-(4-ethyl-1,3-thiazol-2-yl)ethyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound CCC1=CSC(CCC2CC(NCC2)C(=O)NC(C(C)C)C2C(C(O)C(O)C(SC)O2)O)=N1 CVROZZFVFAXTKC-UHFFFAOYSA-N 0.000 claims 4
- OZBVXYHTCGJFOZ-UHFFFAOYSA-N 4-[2-(4-methyl-1,3-thiazol-2-yl)ethyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCC=2SC=C(C)N=2)C1 OZBVXYHTCGJFOZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 4
- JEWPVRAVLNZTFI-UHFFFAOYSA-N n-[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-[3-(difluoromethylsulfanyl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)Cl)NC(=O)C1NCCC(CCCSC(F)F)C1 JEWPVRAVLNZTFI-UHFFFAOYSA-N 0.000 claims 4
- WMLLIPGOPKGHDP-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-[(4-methylphenyl)methylsulfanyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC=2C=CC(C)=CC=2)C1 WMLLIPGOPKGHDP-UHFFFAOYSA-N 0.000 claims 4
- NBTVKZAHDVVTCW-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(pyrrol-1-ylmethyl)piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CN2C=CC=C2)C1 NBTVKZAHDVVTCW-UHFFFAOYSA-N 0.000 claims 4
- ADZCSXXLFDMSBV-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-[2-(triazol-1-yl)ethyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCN2N=NC=C2)C1 ADZCSXXLFDMSBV-UHFFFAOYSA-N 0.000 claims 4
- KAJCUQFVHXVSBW-UHFFFAOYSA-N 1-(2-formamidoethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound O=CNCCN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 KAJCUQFVHXVSBW-UHFFFAOYSA-N 0.000 claims 3
- VXBWHDAHGGGGRO-UHFFFAOYSA-N 1-[2-(methylamino)-2-oxoethyl]-4-pentylpyrrolidine-2-carboxylic acid Chemical compound CCCCCC1CC(C(O)=O)N(CC(=O)NC)C1 VXBWHDAHGGGGRO-UHFFFAOYSA-N 0.000 claims 3
- IPSSNWBTNLRVJF-UHFFFAOYSA-N 4-(3-cyclohexyloxypropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCOC2CCCCC2)C1 IPSSNWBTNLRVJF-UHFFFAOYSA-N 0.000 claims 3
- XIMHZYAPAGVPED-UHFFFAOYSA-N 4-(3-ethoxyiminopropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CCC=NOCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 XIMHZYAPAGVPED-UHFFFAOYSA-N 0.000 claims 3
- DFFGSIHJPZINEB-UHFFFAOYSA-N 4-(3-methoxyiminopropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CCC=NOC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 DFFGSIHJPZINEB-UHFFFAOYSA-N 0.000 claims 3
- SQKDXZQUEXTRJB-UHFFFAOYSA-N 4-[3-(difluoromethylsulfanyl)propyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCSC(F)F)C1 SQKDXZQUEXTRJB-UHFFFAOYSA-N 0.000 claims 3
- FPMGQPCEYFNJEM-UHFFFAOYSA-N n-[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-fluoro-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)(F)CNC1C(=O)NC(C(C)Cl)C1C(O)C(O)C(O)C(SC)O1 FPMGQPCEYFNJEM-UHFFFAOYSA-N 0.000 claims 3
- ZLYNPMCTYTWOKI-UHFFFAOYSA-N (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-[[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]carbamoyl]-4-pentylpyrrolidine-1-carboxylate Chemical compound C1C(CCCCC)CC(C(=O)NC(C(C)C)C2C(C(O)C(O)C(CCC)O2)O)N1C(=O)OCC=1OC(=O)OC=1C ZLYNPMCTYTWOKI-UHFFFAOYSA-N 0.000 claims 2
- XFNUUYSUWJWLNT-UHFFFAOYSA-N 4-(4-fluorophenyl)sulfanyl-n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SC=2C=CC(F)=CC=2)C1 XFNUUYSUWJWLNT-UHFFFAOYSA-N 0.000 claims 2
- YVHZPBYIMYXYOQ-UHFFFAOYSA-N 4-[(2-chlorophenyl)methylsulfanyl]-n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC=2C(=CC=CC=2)Cl)C1 YVHZPBYIMYXYOQ-UHFFFAOYSA-N 0.000 claims 2
- YDLWJBLUPXZDMU-UHFFFAOYSA-N 4-[3-(2-oxopyrrolidin-1-yl)propyl]piperidine-2-carboxylic acid Chemical compound C1CNC(C(=O)O)CC1CCCN1C(=O)CCC1 YDLWJBLUPXZDMU-UHFFFAOYSA-N 0.000 claims 2
- RIARHRRVRFDSBD-UHFFFAOYSA-N 4-butylsulfanyl-n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound C1C(SCCCC)CNC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 RIARHRRVRFDSBD-UHFFFAOYSA-N 0.000 claims 2
- XOJKYRONHSCESN-UHFFFAOYSA-N 4-fluoro-4-propylpiperidine-2-carboxylic acid Chemical compound CCCC1(F)CCNC(C(O)=O)C1 XOJKYRONHSCESN-UHFFFAOYSA-N 0.000 claims 2
- KJQAZPSDPJLGHW-UHFFFAOYSA-N 4-fluoro-n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)(F)CNC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 KJQAZPSDPJLGHW-UHFFFAOYSA-N 0.000 claims 2
- LIAGTEFTMYPSRZ-UHFFFAOYSA-N [4,5-dihydroxy-6-[2-methyl-1-[(4-pentylpyrrolidine-2-carbonyl)amino]propyl]-2-propyloxan-3-yl] dihydrogen phosphate Chemical compound C1C(CCCCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(OP(O)(O)=O)C(CCC)O1 LIAGTEFTMYPSRZ-UHFFFAOYSA-N 0.000 claims 2
- JNOLRCFZNMPDIO-UHFFFAOYSA-N [4,5-dihydroxy-6-[2-methyl-1-[(4-pentylpyrrolidine-2-carbonyl)amino]propyl]-2-propyloxan-3-yl] hexadecanoate Chemical compound OC1C(O)C(OC(=O)CCCCCCCCCCCCCCC)C(CCC)OC1C(C(C)C)NC(=O)C1NCC(CCCCC)C1 JNOLRCFZNMPDIO-UHFFFAOYSA-N 0.000 claims 2
- IBWQQAGVOVLECJ-UHFFFAOYSA-N [4,5-dihydroxy-6-[2-methyl-1-[(4-propylpyrrolidine-2-carbonyl)amino]propyl]-2-propyloxan-3-yl] hexadecanoate Chemical compound OC1C(O)C(OC(=O)CCCCCCCCCCCCCCC)C(CCC)OC1C(C(C)C)NC(=O)C1NCC(CCC)C1 IBWQQAGVOVLECJ-UHFFFAOYSA-N 0.000 claims 2
- YQRAVPQGKCBDCK-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(3-methylbutylsulfanyl)pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCCC(C)C)C1 YQRAVPQGKCBDCK-UHFFFAOYSA-N 0.000 claims 2
- AUWNMJQCSHMKMT-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-[(3-methylphenyl)methylsulfanyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC=2C=C(C)C=CC=2)C1 AUWNMJQCSHMKMT-UHFFFAOYSA-N 0.000 claims 2
- DVCMRITUTVVRFF-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-[2-(2-sulfanylethoxy)ethylsulfanyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCCOCCS)C1 DVCMRITUTVVRFF-UHFFFAOYSA-N 0.000 claims 2
- WQWPEFCBEHKSOA-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC=2C=CC(OC(F)(F)F)=CC=2)C1 WQWPEFCBEHKSOA-UHFFFAOYSA-N 0.000 claims 2
- GCZKMIKZQQZWNE-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pyridin-4-ylsulfanylpyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SC=2C=CN=CC=2)C1 GCZKMIKZQQZWNE-UHFFFAOYSA-N 0.000 claims 2
- PTBVYWPTUFDVAQ-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-[3-(2-oxopyrrolidin-1-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCN2C(CCC2)=O)C1 PTBVYWPTUFDVAQ-UHFFFAOYSA-N 0.000 claims 2
- YKTCRJMDZJEYIR-UHFFFAOYSA-N n-[2-methyl-1-[3,4,5-trihydroxy-6-(2-methylsulfanylethyl)oxan-2-yl]propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CCSC)O1 YKTCRJMDZJEYIR-UHFFFAOYSA-N 0.000 claims 2
- WRCFHQGUCJQRQD-UHFFFAOYSA-N n-[2-methyl-1-[3,4,5-trihydroxy-6-(3-hydroxypropyl)oxan-2-yl]propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CCCO)O1 WRCFHQGUCJQRQD-UHFFFAOYSA-N 0.000 claims 2
- DXLZIQZZYZSKEP-UHFFFAOYSA-N (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-[[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]carbamoyl]-4-propylpyrrolidine-1-carboxylate Chemical compound C1C(CCC)CC(C(=O)NC(C(C)C)C2C(C(O)C(O)C(CCC)O2)O)N1C(=O)OCC=1OC(=O)OC=1C DXLZIQZZYZSKEP-UHFFFAOYSA-N 0.000 claims 1
- YXTGYVVINPIWMF-UHFFFAOYSA-N 1-(1h-imidazol-2-ylmethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound C1C(CCCCC)CC(C(=O)NC(C(C)C)C2C(C(O)C(O)C(SC)O2)O)N1CC1=NC=CN1 YXTGYVVINPIWMF-UHFFFAOYSA-N 0.000 claims 1
- LZDZOCRKNQTXBI-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-pentylpyrrolidine-2-carboxylic acid Chemical compound CCCCCC1CC(C(O)=O)N(CCO)C1 LZDZOCRKNQTXBI-UHFFFAOYSA-N 0.000 claims 1
- FTQINIXAQTXBTI-UHFFFAOYSA-N 1-(cyanomethyl)-4-pentylpyrrolidine-2-carboxylic acid Chemical compound CCCCCC1CC(C(O)=O)N(CC#N)C1 FTQINIXAQTXBTI-UHFFFAOYSA-N 0.000 claims 1
- RJXIDLJYORRWLJ-UHFFFAOYSA-N 1-[2-(methylamino)-2-oxoethyl]-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound CNC(=O)CN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 RJXIDLJYORRWLJ-UHFFFAOYSA-N 0.000 claims 1
- FLOCIAVGIOZWEB-UHFFFAOYSA-N 2-[[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]carbamoyl]-5-propylazepane-1-carboxylic acid Chemical compound OC(=O)N1CCC(CCC)CCC1C(=O)NC(C(C)Cl)C1C(O)C(O)C(O)C(SC)O1 FLOCIAVGIOZWEB-UHFFFAOYSA-N 0.000 claims 1
- CWQJFMOBMLREAC-UHFFFAOYSA-N 4-(2,2,2-trifluoroethylsulfanyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CC(SCC(F)(F)F)CN1 CWQJFMOBMLREAC-UHFFFAOYSA-N 0.000 claims 1
- KBOXSFMMTPTBRC-UHFFFAOYSA-N 4-(2-cyclopropylethyl)piperidine-2-carboxylic acid Chemical compound C1CNC(C(=O)O)CC1CCC1CC1 KBOXSFMMTPTBRC-UHFFFAOYSA-N 0.000 claims 1
- CRHNWQQNNGAEER-UHFFFAOYSA-N 4-(3,3,3-trifluoropropylsulfanyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CC(SCCC(F)(F)F)CN1 CRHNWQQNNGAEER-UHFFFAOYSA-N 0.000 claims 1
- RDZFQGXFGQWNTQ-UHFFFAOYSA-N 4-(3-cyclohexyloxypropyl)piperidine-2-carboxylic acid Chemical compound C1CNC(C(=O)O)CC1CCCOC1CCCCC1 RDZFQGXFGQWNTQ-UHFFFAOYSA-N 0.000 claims 1
- MLSLWQHJKLGJOT-UHFFFAOYSA-N 4-(3-ethylsulfanylpropyl)piperidine-2-carboxylic acid Chemical compound CCSCCCC1CCNC(C(O)=O)C1 MLSLWQHJKLGJOT-UHFFFAOYSA-N 0.000 claims 1
- KIEQCVIQWZRPGB-UHFFFAOYSA-N 4-(3-pyridin-4-ylpropyl)pyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1CCCC1=CC=NC=C1 KIEQCVIQWZRPGB-UHFFFAOYSA-N 0.000 claims 1
- GKALPOLBBGCSPP-UHFFFAOYSA-N 4-(pyrazin-2-ylmethylsulfanyl)pyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1SCC1=CN=CC=N1 GKALPOLBBGCSPP-UHFFFAOYSA-N 0.000 claims 1
- LYXZERIBWVQOKI-UHFFFAOYSA-N 4-(thiophen-2-ylmethylsulfanyl)pyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1SCC1=CC=CS1 LYXZERIBWVQOKI-UHFFFAOYSA-N 0.000 claims 1
- LXPYIDVMBKEWSR-UHFFFAOYSA-N 4-[(2,4-dichlorophenyl)methylsulfanyl]pyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1SCC1=CC=C(Cl)C=C1Cl LXPYIDVMBKEWSR-UHFFFAOYSA-N 0.000 claims 1
- HXWYQIJZYOXRLX-UHFFFAOYSA-N 4-[3-(difluoromethylsulfanyl)propyl]piperidine-2-carboxylic acid Chemical compound OC(=O)C1CC(CCCSC(F)F)CCN1 HXWYQIJZYOXRLX-UHFFFAOYSA-N 0.000 claims 1
- FWKVABSODRWXDO-UHFFFAOYSA-N 4-butyl-1-methyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound CN1CC(CCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CCC)O1 FWKVABSODRWXDO-UHFFFAOYSA-N 0.000 claims 1
- SFISUKXJHSHWIA-UHFFFAOYSA-N 4-butyl-1-methylpyrrolidine-2-carboxylic acid Chemical compound CCCCC1CC(C(O)=O)N(C)C1 SFISUKXJHSHWIA-UHFFFAOYSA-N 0.000 claims 1
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- 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 description 1
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- ZYDKYFIXEYSNPO-UHFFFAOYSA-N tert-butyl-dimethyl-prop-2-ynoxysilane Chemical compound CC(C)(C)[Si](C)(C)OCC#C ZYDKYFIXEYSNPO-UHFFFAOYSA-N 0.000 description 1
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- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Epidemiology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US47929603P | 2003-06-17 | 2003-06-17 | |
US47950203P | 2003-06-17 | 2003-06-17 | |
US60/479,296 | 2003-06-17 | ||
US60/479,502 | 2003-06-17 | ||
US10/642,807 | 2003-08-15 | ||
US10/642,807 US7164011B2 (en) | 2002-08-15 | 2003-08-15 | Lincomycin derivatives possessing antibacterial activity |
US10/777,455 US7199105B2 (en) | 2002-08-15 | 2004-02-11 | Lincomycin derivatives possessing antibacterial activity |
US10/777,455 | 2004-02-11 | ||
PCT/US2004/019689 WO2005012320A2 (fr) | 2003-06-17 | 2004-06-17 | Nouveaux derives de lincomycine possedant une activite antimicrobienne |
Publications (1)
Publication Number | Publication Date |
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AU2004261550A1 true AU2004261550A1 (en) | 2005-02-10 |
Family
ID=40203032
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2004261550A Abandoned AU2004261550A1 (en) | 2003-06-17 | 2004-06-17 | Novel lincomycin derivatives possessing antimicrobial activity |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP1644393A2 (fr) |
JP (1) | JP2007516172A (fr) |
KR (1) | KR20060091050A (fr) |
AU (1) | AU2004261550A1 (fr) |
BR (1) | BRPI0411534A (fr) |
CA (1) | CA2528592A1 (fr) |
EC (1) | ECSP056233A (fr) |
GE (1) | GEP20084437B (fr) |
HK (1) | HK1090061A1 (fr) |
IL (1) | IL172183A0 (fr) |
IS (1) | IS8147A (fr) |
MA (1) | MA27860A1 (fr) |
MX (1) | MXPA05013915A (fr) |
NO (1) | NO20055893L (fr) |
OA (1) | OA13179A (fr) |
RS (1) | RS20050931A (fr) |
WO (1) | WO2005012320A2 (fr) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7199105B2 (en) | 2002-08-15 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
EP1529052A2 (fr) | 2002-08-15 | 2005-05-11 | Vicuron Pharmaceuticals, Inc. | Derives de lincomycine presentant une activite antibacterienne |
US7256177B2 (en) | 2003-06-17 | 2007-08-14 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
EP1654268A2 (fr) * | 2003-06-17 | 2006-05-10 | Vicuron Pharmaceuticals, Inc. | Derives de lincomycine a activite anti-bacterienne |
US7199106B2 (en) | 2003-06-17 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antimicrobial activity |
US7361743B2 (en) * | 2004-02-11 | 2008-04-22 | Pfizer Inc | Lincomycin derivatives possessing antibacterial activity |
KR20080041722A (ko) * | 2005-08-31 | 2008-05-13 | 와이어쓰 | 글리실사이클린의 9-아미노카르보닐 치환된 유도체 |
JP5064237B2 (ja) | 2005-12-09 | 2012-10-31 | Meiji Seikaファルマ株式会社 | リンコマイシン誘導体およびこれを有効成分とする抗菌剤 |
US7867980B2 (en) | 2007-05-31 | 2011-01-11 | Meiji Seika Kaisha, Ltd. | Lincosamide derivatives and antimicrobial agents comprising the same as active ingredient |
US7879808B2 (en) | 2007-05-31 | 2011-02-01 | Meiji Seika Kaisha, Ltd. | Lincomycin derivatives and antimicrobial agents comprising the same as active ingredient |
US8822679B2 (en) * | 2011-06-24 | 2014-09-02 | California Institute Of Technology | Quaternary heteroatom containing compounds |
US20130267699A1 (en) | 2011-06-24 | 2013-10-10 | California Institute Of Technology | Quaternary heteroatom containing compounds |
US10421696B2 (en) | 2014-12-18 | 2019-09-24 | California Institute Of Technology | Enantioselective synthesis of α-quaternary mannich adducts by palladium-catalyzed allylic alkylation |
US10106479B2 (en) | 2015-03-27 | 2018-10-23 | California Institute Of Technology | Asymmetric catalytic decarboxylative alkyl alkylation using low catalyst concentrations and a robust precatalyst |
WO2017156239A1 (fr) | 2016-03-11 | 2017-09-14 | California Institute Of Technology | Compositions et procédés d'acylation de lactames |
EP3480190B1 (fr) | 2017-11-01 | 2023-01-04 | California Institute of Technology | Procédés d'alkylation allylique énantiosélective d'esters, lactones et lactames avec des alcools allyliques inactivés |
EP3699173A1 (fr) | 2018-10-18 | 2020-08-26 | California Institute of Technology | Pyrrolidines, pipérazines et diazépanes disubstitués par gem, compositions et leurs procédés de fabrication |
CN110357839A (zh) * | 2019-08-29 | 2019-10-22 | 重庆经致制药技术开发有限公司 | 布瓦西坦手性中间体的制备方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL128232C (fr) * | 1964-04-13 | |||
US3268556A (en) * | 1964-04-13 | 1966-08-23 | Upjohn Co | Novel lincomycin derivatives |
NL146501C (fr) * | 1964-07-01 | |||
US3282917A (en) * | 1964-08-17 | 1966-11-01 | Upjohn Co | Methyl n-(1-alkyl-4-alkoxy-prolyl)-alpha-thiolincosaminide compounds and process therefor |
NL140527B (nl) * | 1965-02-08 | 1973-12-17 | Upjohn Co | Werkwijze ter bereiding van aan lincomycine verwante verbindingen. |
US3496163A (en) * | 1965-02-08 | 1970-02-17 | Upjohn Co | 7-halo-7-deoxylincomycins and process for preparing the same |
US3555007A (en) * | 1968-07-22 | 1971-01-12 | Upjohn Co | 7-deoxy-7-halo lincomycin d derivatives |
US3549615A (en) * | 1968-10-17 | 1970-12-22 | Upjohn Co | Lincomycin derivatives and process for producing the same |
DE2118636A1 (de) * | 1970-04-20 | 1971-11-04 | The Upjohn Co., Kalamazoo, Mich. (V.StA.) | 3-Nucleotide von Lincomycin und deren Analogen, Verfahren zu ihrer Herstellung und ihre Verwendung in therapeutischen Präparaten |
US3787390A (en) * | 1971-06-23 | 1974-01-22 | Upjohn Co | Analogs of lincomycin and process |
US3849396A (en) * | 1973-01-08 | 1974-11-19 | Upjohn Co | Lincomycin and clindamycin 1-o-ethers |
US3923602A (en) * | 1973-10-25 | 1975-12-02 | Upjohn Co | Composition of matter and process |
JPS5641239A (en) * | 1979-09-13 | 1981-04-17 | Hitachi Cable Ltd | Flame-retardant composition |
US4278789A (en) * | 1979-11-23 | 1981-07-14 | The Upjohn Company | Lincomycin compounds |
EP1529052A2 (fr) * | 2002-08-15 | 2005-05-11 | Vicuron Pharmaceuticals, Inc. | Derives de lincomycine presentant une activite antibacterienne |
BRPI0411537A (pt) * | 2003-06-17 | 2006-08-01 | Vicuron Pharm Inc | derivados de lincomicina que possuem atividade antibacteriana |
-
2004
- 2004-06-17 CA CA002528592A patent/CA2528592A1/fr not_active Abandoned
- 2004-06-17 OA OA1200500364A patent/OA13179A/en unknown
- 2004-06-17 WO PCT/US2004/019689 patent/WO2005012320A2/fr active Application Filing
- 2004-06-17 JP JP2006517464A patent/JP2007516172A/ja active Pending
- 2004-06-17 RS YUP-2005/0931A patent/RS20050931A/sr unknown
- 2004-06-17 MX MXPA05013915A patent/MXPA05013915A/es unknown
- 2004-06-17 AU AU2004261550A patent/AU2004261550A1/en not_active Abandoned
- 2004-06-17 GE GEAP20049117A patent/GEP20084437B/en unknown
- 2004-06-17 BR BRPI0411534-1A patent/BRPI0411534A/pt not_active IP Right Cessation
- 2004-06-17 KR KR1020057024291A patent/KR20060091050A/ko active Search and Examination
- 2004-06-17 EP EP04776816A patent/EP1644393A2/fr not_active Withdrawn
-
2005
- 2005-11-24 IL IL172183A patent/IL172183A0/en unknown
- 2005-11-24 IS IS8147A patent/IS8147A/is unknown
- 2005-12-12 NO NO20055893A patent/NO20055893L/no not_active Application Discontinuation
- 2005-12-16 MA MA28672A patent/MA27860A1/fr unknown
- 2005-12-16 EC EC2005006233A patent/ECSP056233A/es unknown
-
2006
- 2006-09-21 HK HK06110528.4A patent/HK1090061A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NO20055893L (no) | 2006-03-14 |
CA2528592A1 (fr) | 2005-02-10 |
IS8147A (is) | 2005-11-24 |
IL172183A0 (en) | 2011-08-01 |
HK1090061A1 (en) | 2006-12-15 |
WO2005012320A3 (fr) | 2005-10-20 |
RS20050931A (en) | 2008-04-04 |
KR20060091050A (ko) | 2006-08-17 |
EP1644393A2 (fr) | 2006-04-12 |
MA27860A1 (fr) | 2006-04-03 |
WO2005012320A2 (fr) | 2005-02-10 |
BRPI0411534A (pt) | 2006-08-22 |
OA13179A (en) | 2006-12-13 |
GEP20084437B (en) | 2008-07-25 |
MXPA05013915A (es) | 2006-07-03 |
JP2007516172A (ja) | 2007-06-21 |
ECSP056233A (es) | 2006-04-19 |
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Legal Events
Date | Code | Title | Description |
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MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |