OA13179A - Novel lincomycin derivatives possessing antimicrobial activity. - Google Patents

Novel lincomycin derivatives possessing antimicrobial activity. Download PDF

Info

Publication number: OA13179A
Authority: OA; OAPI
Prior art keywords: propyl; tetrahydro; pyran; trihydroxy; methylsulfanyl
Prior art date: 2003-06-17

Application number

OA1200500364A

Other languages

English (en)

Inventor

Sampath K Anandan

Mikhail F Gordeev

Jason G Lewis

Hardwin O'dowd

Original Assignee

Vicuron Pharm Inc

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.)

2003-06-17

Filing date

2004-06-17

Publication date

2006-12-13

2003-08-15 Priority claimed from US10/642,807 external-priority patent/US7164011B2/en

2004-02-11 Priority claimed from US10/777,455 external-priority patent/US7199105B2/en

2004-06-17 Application filed by Vicuron Pharm Inc filed Critical Vicuron Pharm Inc

2006-12-13 Publication of OA13179A publication Critical patent/OA13179A/en

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 abstract description 18
230000000845 anti-microbial effect Effects 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 177
125000000217 alkyl group Chemical group 0.000 claims description 291
-1 4-pentyl-pyrrolidine-2-carbonyl Chemical group 0.000 claims description 227
229910052739 hydrogen Inorganic materials 0.000 claims description 184
239000001257 hydrogen Substances 0.000 claims description 183
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 157
125000000547 substituted alkyl group Chemical group 0.000 claims description 126
125000004414 alkyl thio group Chemical group 0.000 claims description 99
125000003342 alkenyl group Chemical group 0.000 claims description 90
125000005843 halogen group Chemical group 0.000 claims description 88
125000001072 heteroaryl group Chemical group 0.000 claims description 87
125000005017 substituted alkenyl group Chemical group 0.000 claims description 76
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 67
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
125000003545 alkoxy group Chemical group 0.000 claims description 53
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 53
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
125000003118 aryl group Chemical group 0.000 claims description 47
125000000623 heterocyclic group Chemical group 0.000 claims description 45
125000005415 substituted alkoxy group Chemical group 0.000 claims description 44
239000002253 acid Substances 0.000 claims description 42
229910052757 nitrogen Inorganic materials 0.000 claims description 42
229910052760 oxygen Inorganic materials 0.000 claims description 41
239000001301 oxygen Substances 0.000 claims description 40
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
125000003107 substituted aryl 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 33
239000000651 prodrug Substances 0.000 claims description 32
229940002612 prodrug Drugs 0.000 claims description 32
125000000753 cycloalkyl group Chemical group 0.000 claims description 30
125000001424 substituent group Chemical group 0.000 claims description 30
150000001412 amines Chemical class 0.000 claims description 28
150000002148 esters Chemical class 0.000 claims description 26
125000004356 hydroxy functional group Chemical group O* 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 26
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 23
241000124008 Mammalia Species 0.000 claims description 22
125000000304 alkynyl group Chemical group 0.000 claims description 22
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
208000015181 infectious disease Diseases 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 20
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 19
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
TVVQUVMUAMNLLX-UHFFFAOYSA-N 2-(1-amino-2-chloropropyl)-6-methylsulfanyloxane-3,4,5-triol Chemical compound CSC1OC(C(N)C(C)Cl)C(O)C(O)C1O TVVQUVMUAMNLLX-UHFFFAOYSA-N 0.000 claims description 16
229910020008 S(O) Inorganic materials 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
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 14
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 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
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
125000004001 thioalkyl group Chemical group 0.000 claims description 12
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
125000001153 fluoro group Chemical group F* 0.000 claims description 10
230000000813 microbial effect Effects 0.000 claims description 10
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
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 description 9
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 8
229910003827 NRaRb Inorganic materials 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
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
241000194031 Enterococcus faecium Species 0.000 claims description 7
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
125000005518 carboxamido group Chemical group 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 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 description 6
241000194032 Enterococcus faecalis Species 0.000 claims description 6
241000588655 Moraxella catarrhalis Species 0.000 claims description 6
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
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
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 description 6
150000003141 primary amines Chemical class 0.000 claims description 6
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 6
229910052705 radium Inorganic materials 0.000 claims description 6
229910052701 rubidium Inorganic materials 0.000 claims description 6
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 description 5
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 description 5
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 description 5
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 5
HMSWIFDRIQNBGG-UHFFFAOYSA-N 2-(1-amino-2-methylpropyl)-6-propyloxane-3,4,5-triol Chemical compound CCCC1OC(C(N)C(C)C)C(O)C(O)C1O HMSWIFDRIQNBGG-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
241000606124 Bacteroides fragilis Species 0.000 claims description 4
241000606123 Bacteroides thetaiotaomicron Species 0.000 claims description 4
241000193163 Clostridioides difficile Species 0.000 claims description 4
241000588724 Escherichia coli Species 0.000 claims description 4
241000191967 Staphylococcus aureus Species 0.000 claims description 4
241000193998 Streptococcus pneumoniae Species 0.000 claims description 4
229940032049 enterococcus faecalis Drugs 0.000 claims description 4
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 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 description 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 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
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 description 3
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 3
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 3
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 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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 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
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 3
235000021314 Palmitic acid Nutrition 0.000 claims description 3
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 description 3
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 3
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 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
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 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
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 description 2
FQBCBGDNIAEUOW-UHFFFAOYSA-N 2-[[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]carbamoyl]-4-fluoro-4-propylpiperidine-1-carboxylic acid Chemical compound C1C(CCC)(F)CCN(C(O)=O)C1C(=O)NC(C(C)Cl)C1C(O)C(O)C(O)C(SC)O1 FQBCBGDNIAEUOW-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
NKXGEEURCBYMOZ-UHFFFAOYSA-N 4-[(4-methylphenyl)methylsulfanyl]pyrrolidine-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1CSC1CC(C(O)=O)NC1 NKXGEEURCBYMOZ-UHFFFAOYSA-N 0.000 claims description 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 description 2
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 description 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 description 2
YTWSNEQETWKOEE-UHFFFAOYSA-N 4-butylsulfanylpyrrolidine-2-carboxylic acid Chemical compound CCCCSC1CNC(C(O)=O)C1 YTWSNEQETWKOEE-UHFFFAOYSA-N 0.000 claims description 2
DQHUOKOFSXEEAW-UHFFFAOYSA-N 4-propylpyrrolidin-1-ium-2-carboxylate Chemical compound CCCC1CNC(C(O)=O)C1 DQHUOKOFSXEEAW-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
KZCMXQCUJQVHEX-UHFFFAOYSA-N [6-[2-chloro-1-[(4-fluoro-4-propylpiperidine-2-carbonyl)amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] hexadecanoate Chemical compound O1C(SC)C(OC(=O)CCCCCCCCCCCCCCC)C(O)C(O)C1C(C(C)Cl)NC(=O)C1NCCC(F)(CCC)C1 KZCMXQCUJQVHEX-UHFFFAOYSA-N 0.000 claims description 2
WXMKEDHDRCJXMX-UHFFFAOYSA-N [6-[2-chloro-1-[(5-fluoro-5-propylazepane-2-carbonyl)amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate Chemical compound C1CC(CCC)(F)CCNC1C(=O)NC(C(C)Cl)C1C(O)C(O)C(OP(O)(O)=O)C(SC)O1 WXMKEDHDRCJXMX-UHFFFAOYSA-N 0.000 claims description 2
KLKVEPCCSKYZHJ-UHFFFAOYSA-N [6-[2-chloro-1-[(5-propylazepane-2-carbonyl)amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] hexadecanoate Chemical compound O1C(SC)C(OC(=O)CCCCCCCCCCCCCCC)C(O)C(O)C1C(C(C)Cl)NC(=O)C1NCCC(CCC)CC1 KLKVEPCCSKYZHJ-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
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 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
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 description 2
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 2
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 description 2
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 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 description 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 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 17
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
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 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
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 4
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 4
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 3
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 3
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 3
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 3
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 3
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 3
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 2
JAGZVFIOIJHOFQ-UHFFFAOYSA-N 2-[[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]carbamoyl]-4-pentylpyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CCC)O1 JAGZVFIOIJHOFQ-UHFFFAOYSA-N 0.000 claims 2
ORFBIJWBRZFLCN-UHFFFAOYSA-N 2-[[2-methyl-1-(3,4,5-trihydroxy-6-propyloxan-2-yl)propyl]carbamoyl]-4-propylpyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CC(CCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(CCC)O1 ORFBIJWBRZFLCN-UHFFFAOYSA-N 0.000 claims 2
LQWDJYFRULESRD-UHFFFAOYSA-N 4-(pyridin-2-ylmethylsulfanyl)pyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1SCC1=CC=CC=N1 LQWDJYFRULESRD-UHFFFAOYSA-N 0.000 claims 2
JNBJRGXYGPSWLD-UHFFFAOYSA-N 4-[(3-methylphenyl)methylsulfanyl]pyrrolidine-2-carboxylic acid Chemical compound CC1=CC=CC(CSC2CC(NC2)C(O)=O)=C1 JNBJRGXYGPSWLD-UHFFFAOYSA-N 0.000 claims 2
FVOOQCWRMPHUEZ-UHFFFAOYSA-N 4-[(4-fluorophenyl)methylsulfanyl]pyrrolidin-1-ium-2-carboxylate Chemical compound C1NC(C(=O)O)CC1SCC1=CC=C(F)C=C1 FVOOQCWRMPHUEZ-UHFFFAOYSA-N 0.000 claims 2
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 2
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 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
OLRKOHTWARFZBA-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(3-thiophen-2-ylsulfanylpropyl)piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCSC=2SC=CC=2)C1 OLRKOHTWARFZBA-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
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
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 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
COMCSRWICCBSDR-UHFFFAOYSA-N 2-(1-amino-2-methylpropyl)-6-(2-methylsulfanylethyl)oxane-3,4,5-triol Chemical compound CSCCC1OC(C(N)C(C)C)C(O)C(O)C1O COMCSRWICCBSDR-UHFFFAOYSA-N 0.000 claims 1
HVKOAHBGTNBHRY-UHFFFAOYSA-N 2-[[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]carbamoyl]-5-(cyclopropylmethyl)azepane-1-carboxylic acid Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)Cl)NC(=O)C1N(C(O)=O)CCC(CC2CC2)CC1 HVKOAHBGTNBHRY-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
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
KWYNZULENAEATP-UHFFFAOYSA-N 4-(3-cyanopropyl)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CC(CCCC#N)CCN1 KWYNZULENAEATP-UHFFFAOYSA-N 0.000 claims 1
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 1
IRTDOHPCDLCCLK-UHFFFAOYSA-N 4-(3-imidazol-1-ylpropyl)piperidine-2-carboxylic acid Chemical compound C1CNC(C(=O)O)CC1CCCN1C=NC=C1 IRTDOHPCDLCCLK-UHFFFAOYSA-N 0.000 claims 1
BCLJJMPHDXTYOS-UHFFFAOYSA-N 4-(3-methylbutylsulfanyl)pyrrolidine-2-carboxylic acid Chemical compound CC(C)CCSC1CNC(C(O)=O)C1 BCLJJMPHDXTYOS-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
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 1
LTLKPBZNDJKLHE-UHFFFAOYSA-N 4-propylidenepiperidine-2-carboxylic acid Chemical compound CCC=C1CCNC(C(O)=O)C1 LTLKPBZNDJKLHE-UHFFFAOYSA-N 0.000 claims 1
VPYASVSTOAXXEM-UHFFFAOYSA-N N-[2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-3-(3-cyclobutylpropyl)azetidine-2-carboxamide 4-[3-(difluoromethylsulfanyl)propyl]piperidine-2-carboxylic acid Chemical compound FC(F)SCCCC1CC(NCC1)C(=O)O.ClC(C(C1OC(C(C(C1O)O)O)SC)NC(=O)C1NCC1CCCC1CCC1)C VPYASVSTOAXXEM-UHFFFAOYSA-N 0.000 claims 1
241000191940 Staphylococcus Species 0.000 claims 1
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 1
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 1
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 1
AAZJFEAFVOXPRJ-UHFFFAOYSA-N [6-[2-chloro-1-[(5-fluoro-5-propylazepane-2-carbonyl)amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] hexadecanoate Chemical compound O1C(SC)C(OC(=O)CCCCCCCCCCCCCCC)C(O)C(O)C1C(C(C)Cl)NC(=O)C1NCCC(F)(CCC)CC1 AAZJFEAFVOXPRJ-UHFFFAOYSA-N 0.000 claims 1
VZXJDJJXAKSUMN-UHFFFAOYSA-N [6-[2-chloro-1-[(5-propylazepane-2-carbonyl)amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate Chemical compound C1CC(CCC)CCNC1C(=O)NC(C(C)Cl)C1C(O)C(O)C(OP(O)(O)=O)C(SC)O1 VZXJDJJXAKSUMN-UHFFFAOYSA-N 0.000 claims 1
244000052616 bacterial pathogen Species 0.000 claims 1
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 1
STVMYLXFNNOWLT-UHFFFAOYSA-N n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(2,2,2-trifluoroethylsulfanyl)pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)O)NC(=O)C1NCC(SCC(F)(F)F)C1 STVMYLXFNNOWLT-UHFFFAOYSA-N 0.000 claims 1
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IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
230000000541 pulsatile effect Effects 0.000 description 1
239000008213 purified water Substances 0.000 description 1
150000003214 pyranose derivatives Chemical class 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
102220007331 rs111033633 Human genes 0.000 description 1
VGGUKFAVHPGNBF-UHFFFAOYSA-N s-ethyl 2,2,2-trifluoroethanethioate Chemical compound CCSC(=O)C(F)(F)F VGGUKFAVHPGNBF-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000012058 sterile packaged powder Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003457 sulfones Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
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
238000012956 testing procedure Methods 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
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
230000002588 toxic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
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
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
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 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
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003952 β-lactams Chemical class 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
- A61K31/70—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)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Epidemiology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Crystallography & Structural Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)

OA1200500364A 2003-06-17 2004-06-17 Novel lincomycin derivatives possessing antimicrobial activity. OA13179A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US47929603P	2003-06-17	2003-06-17
US47950203P	2003-06-17	2003-06-17
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

Publications (1)

Publication Number	Publication Date
OA13179A true OA13179A (en)	2006-12-13

Family

ID=40203032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200500364A OA13179A (en)	2003-06-17	2004-06-17	Novel lincomycin derivatives possessing antimicrobial activity.

Country Status (16)

Country	Link
EP (1)	EP1644393A2 (pt)
JP (1)	JP2007516172A (pt)
KR (1)	KR20060091050A (pt)
AU (1)	AU2004261550A1 (pt)
BR (1)	BRPI0411534A (pt)
CA (1)	CA2528592A1 (pt)
EC (1)	ECSP056233A (pt)
GE (1)	GEP20084437B (pt)
IL (1)	IL172183A0 (pt)
IS (1)	IS8147A (pt)
MA (1)	MA27860A1 (pt)
MX (1)	MXPA05013915A (pt)
NO (1)	NO20055893L (pt)
OA (1)	OA13179A (pt)
RS (1)	RS20050931A (pt)
WO (1)	WO2005012320A2 (pt)

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US7164011B2 (en)	2002-08-15	2007-01-16	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
US7199105B2 (en)	2002-08-15	2007-04-03	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
US7256177B2 (en)	2003-06-17	2007-08-14	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
WO2005007665A2 (en) *	2003-06-17	2005-01-27	Vicuron Pharmaceuticals Inc.	Lincomycin derivatives possessing antibacterial activity
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
JP2009507793A (ja) *	2005-08-31	2009-02-26	ワイス	グリシルサイクリンの９−アミノカルボニル置換誘導体
EP1970377A4 (en)	2005-12-09	2013-02-27	Meiji Seika Kaisha	LINCOMYCIN DERIVATIVE AND ANTIBACTERIAL AGENT CONTAINING THIS AS AN ACTIVE SUBSTANCE
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
CN107922373A (zh)	2015-03-27	2018-04-17	加利福尼亚技术学院	使用低催化剂浓度和稳定的预催化剂的不对称催化脱羧烷基烷基化
WO2017156239A1 (en)	2016-03-11	2017-09-14	California Institute Of Technology	Compositions and methods for acylating lactams
EP3480190B1 (en)	2017-11-01	2023-01-04	California Institute of Technology	Methods for enantioselective allylic alkylation of esters, lactones, and lactams with unactivated allylic alcohols
US11214568B2 (en)	2018-10-18	2022-01-04	California Institute Of Technology	Gem-disubstituted pyrrolidines, piperazines, and diazepanes, and compositions and methods of making the same
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

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NL128232C (pt) *	1964-04-13
US3268556A (en) *	1964-04-13	1966-08-23	Upjohn Co	Novel lincomycin derivatives
NL146501C (pt) *	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
US7164011B2 (en) *	2002-08-15	2007-01-16	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
JP2007528360A (ja) *	2003-06-17	2007-10-11	ビキュロン・ファーマシューティカルズ・インコーポレイテッド	抗菌活性を有するリンコマイシン誘導体

2004
- 2004-06-17 AU AU2004261550A patent/AU2004261550A1/en not_active Abandoned
- 2004-06-17 WO PCT/US2004/019689 patent/WO2005012320A2/en not_active Ceased
- 2004-06-17 GE GEAP20049117A patent/GEP20084437B/en unknown
- 2004-06-17 KR KR1020057024291A patent/KR20060091050A/ko not_active Ceased
- 2004-06-17 EP EP04776816A patent/EP1644393A2/en not_active Withdrawn
- 2004-06-17 JP JP2006517464A patent/JP2007516172A/ja active Pending
- 2004-06-17 CA CA002528592A patent/CA2528592A1/en not_active Abandoned
- 2004-06-17 MX MXPA05013915A patent/MXPA05013915A/es unknown
- 2004-06-17 RS YUP-2005/0931A patent/RS20050931A/sr unknown
- 2004-06-17 OA OA1200500364A patent/OA13179A/en unknown
- 2004-06-17 BR BRPI0411534-1A patent/BRPI0411534A/pt not_active IP Right Cessation
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 EC EC2005006233A patent/ECSP056233A/es unknown
- 2005-12-16 MA MA28672A patent/MA27860A1/fr unknown

Also Published As

Publication number	Publication date
WO2005012320A3 (en)	2005-10-20
MA27860A1 (fr)	2006-04-03
EP1644393A2 (en)	2006-04-12
IS8147A (is)	2005-11-24
WO2005012320A2 (en)	2005-02-10
BRPI0411534A (pt)	2006-08-22
IL172183A0 (en)	2011-08-01
JP2007516172A (ja)	2007-06-21
CA2528592A1 (en)	2005-02-10
AU2004261550A1 (en)	2005-02-10
HK1090061A1 (zh)	2006-12-15
GEP20084437B (en)	2008-07-25
ECSP056233A (es)	2006-04-19
MXPA05013915A (es)	2006-07-03
KR20060091050A (ko)	2006-08-17
NO20055893L (no)	2006-03-14
RS20050931A (sr)	2008-04-04

Publication	Publication Date	Title
OA13179A (en)	2006-12-13	Novel lincomycin derivatives possessing antimicrobial activity.
US7361743B2 (en)	2008-04-22	Lincomycin derivatives possessing antibacterial activity
KR100976063B1 (ko)	2010-08-17	신규한 벤즈아미드 유도체 화합물 및 그의 제조방법
AU2003265475B2 (en)	2009-08-27	Lincomycin derivatives possessing antibacterial activity
TW201247693A (en)	2012-12-01	C-4" position substituted macrolide derivative
CA3066857A1 (en)	2019-01-03	Heteroaryldihydropyrimidine derivatives and methods of treating hepatitis b infections
EP1710248A1 (en)	2006-10-11	Novel aminoglycoside antibiotic effective against methicillin resistant staphylococcus aureus (mrsa)
US20040230046A1 (en)	2004-11-18	Lincomycin derivatives possessing antibacterial activity
US20050043248A1 (en)	2005-02-24	Novel lincomycin derivatives possessing antimicrobial activity
US7256177B2 (en)	2007-08-14	Lincomycin derivatives possessing antibacterial activity
EP1654268A2 (en)	2006-05-10	Lincomycin derivatives possessing antibacterial activity
JP5356223B2 (ja)	2013-12-04	リンコマイシン誘導体及びこれを有効成分とする抗菌剤
WO2007037518A9 (ja)	2007-05-31	ムチリン誘導体及びそれを含有する医薬組成物
HK1090061B (en)	2010-09-30	Novel lincomycin derivatives possessing antimicrobial activity
CN1823083B (zh)	2010-05-26	具备抗微生物活性的林可霉素衍生物
MXPA05014064A (en)	2006-10-17	Lincomycin derivatives possessing antibacterial activity
KR20090099594A (ko)	2009-09-22	항균 활성을 갖는 신규 린코마이신 유도체
JP2007528360A (ja)	2007-10-11	抗菌活性を有するリンコマイシン誘導体