SK8202003A3 - Heterocyclic compounds having antibacterial activity, process for their preparation and pharmaceutical compositions containing them - Google Patents

Heterocyclic compounds having antibacterial activity, process for their preparation and pharmaceutical compositions containing them Download PDF

Info

Publication number: SK8202003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; oxazolan; oxo; salts; phenyl
Prior art date: 2000-12-26

Application number

SK820-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Selvakumar Natesan

Jagattaran Das

Javed Iqbal

Sitaram Kumar Magadi

Naga Venkata Srinivasa Mamidi

Rajagopalan Ramanujam

Baskaran Sundarababu

Braj Bhushan Lohray

Original Assignee

Reddys Lab Ltd Dr

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.)

2000-12-26

Filing date

2001-12-26

Publication date

2004-07-07

2001-12-26 Application filed by Reddys Lab Ltd Dr filed Critical Reddys Lab Ltd Dr

2004-07-07 Publication of SK8202003A3 publication Critical patent/SK8202003A3/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 22
238000000034 method Methods 0.000 title claims description 77
238000002360 preparation method Methods 0.000 title claims description 56
230000008569 process Effects 0.000 title claims description 41
230000000844 anti-bacterial effect Effects 0.000 title description 4
150000002391 heterocyclic compounds Chemical class 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 337
239000012453 solvate Substances 0.000 claims abstract description 29
150000001875 compounds Chemical class 0.000 claims description 375
-1 pyrrolidinylthiocarbonyl Chemical group 0.000 claims description 254
125000000217 alkyl group Chemical group 0.000 claims description 181
238000006243 chemical reaction Methods 0.000 claims description 145
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 133
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 118
229910052736 halogen Inorganic materials 0.000 claims description 117
229910052739 hydrogen Inorganic materials 0.000 claims description 106
239000001257 hydrogen Substances 0.000 claims description 97
125000003118 aryl group Chemical group 0.000 claims description 96
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 83
125000003545 alkoxy group Chemical group 0.000 claims description 72
150000002367 halogens Chemical class 0.000 claims description 71
229910052717 sulfur Inorganic materials 0.000 claims description 71
125000004093 cyano group Chemical group *C#N 0.000 claims description 70
125000003710 aryl alkyl group Chemical group 0.000 claims description 67
125000004104 aryloxy group Chemical group 0.000 claims description 66
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 55
125000000623 heterocyclic group Chemical group 0.000 claims description 55
229910052760 oxygen Inorganic materials 0.000 claims description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
239000002585 base Substances 0.000 claims description 46
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 45
125000005843 halogen group Chemical group 0.000 claims description 45
125000005842 heteroatom Chemical group 0.000 claims description 45
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 44
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 42
239000000243 solution Substances 0.000 claims description 41
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 35
125000003282 alkyl amino group Chemical group 0.000 claims description 35
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
125000004475 heteroaralkyl group Chemical group 0.000 claims description 32
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 29
125000005129 aryl carbonyl group Chemical group 0.000 claims description 29
125000000753 cycloalkyl group Chemical group 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 29
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 28
125000001769 aryl amino group Chemical group 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 28
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 26
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 21
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 19
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 19
230000009467 reduction Effects 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000002252 acyl group Chemical group 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 15
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
125000000464 thioxo group Chemical group S=* 0.000 claims description 14
HXIRTSKHPFRRKO-UHFFFAOYSA-N o-methyl carbamothioate Chemical compound COC(N)=S HXIRTSKHPFRRKO-UHFFFAOYSA-N 0.000 claims description 13
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 12
229940024606 amino acid Drugs 0.000 claims description 12
235000001014 amino acid Nutrition 0.000 claims description 12
150000001413 amino acids Chemical class 0.000 claims description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
208000035143 Bacterial infection Diseases 0.000 claims description 11
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Chemical class 0.000 claims description 11
125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 11
150000001540 azides Chemical class 0.000 claims description 11
208000022362 bacterial infectious disease Diseases 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 10
150000005005 aminopyrimidines Chemical class 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
125000004423 acyloxy group Chemical group 0.000 claims description 9
125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 9
125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 9
ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 9
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
125000003441 thioacyl group Chemical group 0.000 claims description 8
XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims description 7
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Chemical class CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Chemical class CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 7
239000000725 suspension Substances 0.000 claims description 7
125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 6
238000007796 conventional method Methods 0.000 claims description 6
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 6
150000001350 alkyl halides Chemical class 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
150000002540 isothiocyanates Chemical class 0.000 claims description 5
239000000843 powder Substances 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical group CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 4
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 4
239000004472 Lysine Substances 0.000 claims description 4
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 4
239000002775 capsule Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
239000006188 syrup Substances 0.000 claims description 4
235000020357 syrup Nutrition 0.000 claims description 4
239000003826 tablet Substances 0.000 claims description 4
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
235000010323 ascorbic acid Nutrition 0.000 claims description 3
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 3
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 3
229960001231 choline Drugs 0.000 claims description 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
150000002357 guanidines Chemical class 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
UVKKXZAOOHKQGK-SECBINFHSA-N (5r)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1C(=O)OCC1 UVKKXZAOOHKQGK-SECBINFHSA-N 0.000 claims description 2
BAWYOZIGOLWAPE-OAHLLOKOSA-N (5r)-3-[3-fluoro-4-(2-oxo-3-phenylimidazolidin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1C(=O)N(C=2C=CC=CC=2)CC1 BAWYOZIGOLWAPE-OAHLLOKOSA-N 0.000 claims description 2
PHBJXIQJUQZHSI-SECBINFHSA-N (5r)-3-[3-fluoro-4-(2-sulfanylidene-1,3-oxazolidin-3-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1C(=S)OCC1 PHBJXIQJUQZHSI-SECBINFHSA-N 0.000 claims description 2
KGCOHZKSIRCQDH-SNVBAGLBSA-N (5r)-3-[3-fluoro-4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CO)C2)=O)C=C1F KGCOHZKSIRCQDH-SNVBAGLBSA-N 0.000 claims description 2
KIIOFADAAYVPRJ-SNVBAGLBSA-N (5r)-3-[3-fluoro-4-(3-methyl-4-oxoimidazolidin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound C1C(=O)N(C)CN1C1=CC=C(N2C(O[C@@H](CO)C2)=O)C=C1F KIIOFADAAYVPRJ-SNVBAGLBSA-N 0.000 claims description 2
NHHFXULAHBKCJV-SNVBAGLBSA-N (5r)-5-(aminomethyl)-3-[3-fluoro-4-(3-methyl-4-oxoimidazolidin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound C1C(=O)N(C)CN1C1=CC=C(N2C(O[C@H](CN)C2)=O)C=C1F NHHFXULAHBKCJV-SNVBAGLBSA-N 0.000 claims description 2
SUAHEWOAWXRFMO-SECBINFHSA-N (5r)-5-(aminomethyl)-3-[4-(2-oxo-1,3-oxazolidin-3-yl)-3-(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CN)CN1C(C=C1C(F)(F)F)=CC=C1N1C(=O)OCC1 SUAHEWOAWXRFMO-SECBINFHSA-N 0.000 claims description 2
CKONPXQNHZXJQM-LLVKDONJSA-N (5r)-5-(aminomethyl)-3-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CN)CN1C1=CC=C(N2C(OCC2)=O)C=C1 CKONPXQNHZXJQM-LLVKDONJSA-N 0.000 claims description 2
BAUYXWOSBYZLIU-VIFPVBQESA-N (5r)-5-(azidomethyl)-3-[2-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound FC1=CC(N2C(OCC2)=O)=CC=C1N1C[C@H](CN=[N+]=[N-])OC1=O BAUYXWOSBYZLIU-VIFPVBQESA-N 0.000 claims description 2
BNCMOAYLLRWVTM-JTQLQIEISA-N (5r)-5-(azidomethyl)-3-[3-fluoro-4-(3-methyl-4-oxoimidazolidin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound C1C(=O)N(C)CN1C1=CC=C(N2C(O[C@@H](CN=[N+]=[N-])C2)=O)C=C1F BNCMOAYLLRWVTM-JTQLQIEISA-N 0.000 claims description 2
IIGHHEQDSXWERE-VIFPVBQESA-N (5r)-5-(azidomethyl)-3-[4-(2-oxo-1,3-oxazolidin-3-yl)-3-(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one Chemical compound FC(F)(F)C1=CC(N2C(O[C@@H](CN=[N+]=[N-])C2)=O)=CC=C1N1CCOC1=O IIGHHEQDSXWERE-VIFPVBQESA-N 0.000 claims description 2
XQSQMKJQLZRECH-NSHDSACASA-N (5r)-5-(azidomethyl)-3-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CN=[N+]=[N-])CN1C1=CC=C(N2C(OCC2)=O)C=C1 XQSQMKJQLZRECH-NSHDSACASA-N 0.000 claims description 2
QBJWFDSSCNNXBM-SECBINFHSA-N (5r)-5-(hydroxymethyl)-3-[4-(2-oxo-1,3-oxazolidin-3-yl)-3-(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1C(F)(F)F)=CC=C1N1C(=O)OCC1 QBJWFDSSCNNXBM-SECBINFHSA-N 0.000 claims description 2
HLEXURKWLRGWFI-GFCCVEGCSA-N (5r)-5-(hydroxymethyl)-3-[4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CO)C2)=O)C=C1 HLEXURKWLRGWFI-GFCCVEGCSA-N 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
SOVGEJRUGATGBO-VIFPVBQESA-N 2,2,2-trifluoro-n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C(F)(F)F)C2)=O)=CC=C1N1CCOC1=O SOVGEJRUGATGBO-VIFPVBQESA-N 0.000 claims description 2
QNIHBTRLIJORED-UHFFFAOYSA-N 2,4-bis(2-methoxyphenyl)-2,4-bis(sulfanylidene)-1,3,2$l^{5},4$l^{5}-dithiadiphosphetane Chemical compound COC1=CC=CC=C1P1(=S)SP(=S)(C=2C(=CC=CC=2)OC)S1 QNIHBTRLIJORED-UHFFFAOYSA-N 0.000 claims description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 claims description 2
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
229940013085 2-diethylaminoethanol Drugs 0.000 claims description 2
KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical class OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 2
DDJBPAZIWNPETA-JTQLQIEISA-N 3,3,3-trifluoro-n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]propanethioamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=S)CC(F)(F)F)C2)=O)=CC=C1N1CCOC1=O DDJBPAZIWNPETA-JTQLQIEISA-N 0.000 claims description 2
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125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000004708 ribosome subunit Anatomy 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000005505 thiomorpholino group Chemical group 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000014616 translation Effects 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK820-2003A 2000-12-26 2001-12-26 Heterocyclic compounds having antibacterial activity, process for their preparation and pharmaceutical compositions containing them SK8202003A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IN1124MA2000		2000-12-26
IN15MA2001		2001-01-15
PCT/IN2001/000227 WO2002051819A2 (fr)	2000-12-26	2001-12-26	Composés hétérocycliques antibactériens, mode d'élaboration et compositions pharmaceutiques ainsi obtenues

Publications (1)

Publication Number	Publication Date
SK8202003A3 true SK8202003A3 (en)	2004-07-07

Family

ID=26324889

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK820-2003A SK8202003A3 (en)	2000-12-26	2001-12-26	Heterocyclic compounds having antibacterial activity, process for their preparation and pharmaceutical compositions containing them

Country Status (21)

Country	Link
US (2)	US7030148B2 (fr)
EP (1)	EP1345913A2 (fr)
JP (1)	JP2004525876A (fr)
KR (1)	KR20030063472A (fr)
CN (1)	CN1656083A (fr)
BG (1)	BG108022A (fr)
BR (1)	BR0116571A (fr)
CA (1)	CA2433138A1 (fr)
CZ (1)	CZ20031799A3 (fr)
EE (1)	EE200300254A (fr)
HR (1)	HRP20030522A2 (fr)
HU (1)	HUP0302580A2 (fr)
IL (1)	IL156662A0 (fr)
MX (1)	MXPA03005822A (fr)
NO (1)	NO20032926L (fr)
NZ (1)	NZ526716A (fr)
PL (1)	PL363616A1 (fr)
RU (1)	RU2322444C2 (fr)
SK (1)	SK8202003A3 (fr)
WO (1)	WO2002051819A2 (fr)
YU (1)	YU52403A (fr)

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US9643922B2 (en)	2008-08-18	2017-05-09	Yale University	MIF modulators
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CN101798302B (zh) *	2009-02-06	2014-11-05	上海盟科药业有限公司	抗生素类药物1-(邻-氟苯基)二氢吡啶酮的合成及生产的方法和工艺
WO2014045292A1 (fr) *	2012-09-20	2014-03-27	Symed Labs Limited	Procédé amélioré pour la préparation d'un intermédiaire de linézolide
AR092742A1 (es)	2012-10-02	2015-04-29	Intermune Inc	Piridinonas antifibroticas
KR102428252B1 (ko)	2014-02-21	2022-08-02	상하이 미큐알엑스 파마슈티컬 컴퍼니 리미티드	치료적 투여용 수용성 o-카보닐 포스포르아미데이트 전구약물
RU2692485C2 (ru)	2014-04-02	2019-06-25	Интермьюн, Инк.	Противофиброзные пиридиноны
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2001
- 2001-11-26 YU YU52403A patent/YU52403A/sh unknown
- 2001-12-21 US US10/032,392 patent/US7030148B2/en not_active Expired - Fee Related
- 2001-12-26 CA CA002433138A patent/CA2433138A1/fr not_active Abandoned
- 2001-12-26 RU RU2003123104/04A patent/RU2322444C2/ru not_active IP Right Cessation
- 2001-12-26 PL PL01363616A patent/PL363616A1/xx not_active Application Discontinuation
- 2001-12-26 MX MXPA03005822A patent/MXPA03005822A/es not_active Application Discontinuation
- 2001-12-26 BR BR0116571-2A patent/BR0116571A/pt not_active IP Right Cessation
- 2001-12-26 HU HU0302580A patent/HUP0302580A2/hu unknown
- 2001-12-26 WO PCT/IN2001/000227 patent/WO2002051819A2/fr not_active Ceased
- 2001-12-26 JP JP2002552914A patent/JP2004525876A/ja not_active Withdrawn
- 2001-12-26 SK SK820-2003A patent/SK8202003A3/sk not_active Application Discontinuation
- 2001-12-26 IL IL15666201A patent/IL156662A0/xx unknown
- 2001-12-26 EE EEP200300254A patent/EE200300254A/xx unknown
- 2001-12-26 EP EP01995805A patent/EP1345913A2/fr not_active Withdrawn
- 2001-12-26 KR KR10-2003-7008637A patent/KR20030063472A/ko not_active Ceased
- 2001-12-26 CZ CZ20031799A patent/CZ20031799A3/cs unknown
- 2001-12-26 NZ NZ526716A patent/NZ526716A/en unknown
- 2001-12-26 CN CNA018224210A patent/CN1656083A/zh active Pending
- 2001-12-26 HR HR20030522A patent/HRP20030522A2/hr not_active Application Discontinuation
2003
- 2003-06-25 NO NO20032926A patent/NO20032926L/no unknown
- 2003-07-22 BG BG108022A patent/BG108022A/bg unknown
- 2003-08-01 US US10/632,950 patent/US7183301B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HRP20030522A2 (en)	2005-06-30
YU52403A (sh)	2006-03-03
IL156662A0 (en)	2004-01-04
US20030065175A1 (en)	2003-04-03
PL363616A1 (en)	2004-11-29
RU2322444C2 (ru)	2008-04-20
EP1345913A2 (fr)	2003-09-24
WO2002051819A3 (fr)	2002-12-05
KR20030063472A (ko)	2003-07-28
NO20032926L (no)	2003-08-25
WO2002051819A2 (fr)	2002-07-04
WO2002051819A9 (fr)	2003-08-07
JP2004525876A (ja)	2004-08-26
US7183301B2 (en)	2007-02-27
BG108022A (bg)	2004-09-30
RU2003123104A (ru)	2005-03-10
CA2433138A1 (fr)	2002-07-04
US20040059120A1 (en)	2004-03-25
US7030148B2 (en)	2006-04-18
NO20032926D0 (no)	2003-06-25
BR0116571A (pt)	2004-03-02
CZ20031799A3 (cs)	2004-02-18
NZ526716A (en)	2005-08-26
CN1656083A (zh)	2005-08-17
MXPA03005822A (es)	2004-05-04
EE200300254A (et)	2003-12-15
HUP0302580A2 (hu)	2003-11-28

Publication	Publication Date	Title
SK8202003A3 (en)	2004-07-07	Heterocyclic compounds having antibacterial activity, process for their preparation and pharmaceutical compositions containing them
JP7585405B2 (ja)	2024-11-18	抗微生物治療のための置換フェニルオキサゾリジノン
HUT72296A (en)	1996-04-29	Oxazolidinones containing a substituted diazine moiety and pharmaceutical compositions containing them having antimicrobial effect
WO2006014357A1 (fr)	2006-02-09	Inhibiteurs de la cetp
KR20020067557A (ko)	2002-08-22	설폭시민 관능기를 가지는 옥사졸리디논 및항미생물제로서의 그의 용도
US6518285B2 (en)	2003-02-11	Piperidinyloxy and pyrrolidinyloxy oxazolidinone antibacterials
MXPA06003124A (es)	2006-06-20	Profarmacos de aciloximetilcarbamato-oxazolidinonas.
WO2005005398A2 (fr)	2005-01-20	Antibiotiques a base d'oxazolidinone substituee par un groupe cyclipropyl et derives
US8841306B2 (en)	2014-09-23	Antimicrobials
CA2478502A1 (fr)	2003-10-09	Nouveaux composes anti-infectieux, processus de preparation de ces composes et compositions pharmaceutiques les contenant
EP2170874A2 (fr)	2010-04-07	Nouveaux composés et leur utilisation
US20040102494A1 (en)	2004-05-27	Novel heterocyclic compounds having antibacterial activity: process for their preparation and pharmaceutical compositions containing them
WO2003093247A2 (fr)	2003-11-13	Nouveaux agents antibacteriens
KR100636961B1 (ko)	2006-10-19	아졸이 치환된 옥사졸리디논 유도체 및 이의 제조 방법
AU2002226669A1 (en)	2002-07-08	Heterocyclic compounds having antibacterial activity, process for their preparation and pharmaceutical compositions containing them
US20070004712A1 (en)	2007-01-04	Salts of novel heterocyclic compounds having antibacterial activity
US20100234390A1 (en)	2010-09-16	Novel compound and their use
WO2004101552A1 (fr)	2004-11-25	Derives d'oxazolidinone utiles comme agents antibacteriens
US20040072842A1 (en)	2004-04-15	Difluorothioacetamides of oxazolidinones with a glycoloylpiperazine substituent
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