ZA200501033B - 2,3,-dihydro-6-nitroimidazoÄ2,1-BÜoxazoles - Google Patents
2,3,-dihydro-6-nitroimidazoÄ2,1-BÜoxazoles Download PDFInfo
- Publication number
- ZA200501033B ZA200501033B ZA200501033A ZA200501033A ZA200501033B ZA 200501033 B ZA200501033 B ZA 200501033B ZA 200501033 A ZA200501033 A ZA 200501033A ZA 200501033 A ZA200501033 A ZA 200501033A ZA 200501033 B ZA200501033 B ZA 200501033B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- substituted
- halogen
- unsubstituted
- phenyl
- Prior art date
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 535
- 125000000217 alkyl group Chemical group 0.000 claims description 465
- -1 isohexyloxy group Chemical group 0.000 claims description 297
- 125000003545 alkoxy group Chemical group 0.000 claims description 235
- 125000001424 substituent group Chemical group 0.000 claims description 106
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 39
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 18
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000005925 3-methylpentyloxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- WGUXTQDCAZNJIF-UHFFFAOYSA-N 1-methyl-3,5-bis(trifluoromethyl)benzene Chemical group CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WGUXTQDCAZNJIF-UHFFFAOYSA-N 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- 125000006012 2-chloroethoxy group Chemical group 0.000 claims 1
- 125000006499 2-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006500 3-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC(F)(F)F)=C1[H])C([H])([H])* 0.000 claims 1
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
- 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims 1
- 125000006015 bromomethoxy group Chemical group 0.000 claims 1
- 125000004651 chloromethoxy group Chemical group ClCO* 0.000 claims 1
- 125000004788 dichlorofluoromethoxy group Chemical group ClC(O*)(F)Cl 0.000 claims 1
- 125000004783 dichloromethoxy group Chemical group ClC(O*)Cl 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 270
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 109
- 150000001875 compounds Chemical class 0.000 description 74
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 50
- 150000003839 salts Chemical class 0.000 description 44
- 125000003277 amino group Chemical group 0.000 description 39
- 125000002252 acyl group Chemical group 0.000 description 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 description 28
- 125000004093 cyano group Chemical group *C#N 0.000 description 27
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 24
- 125000004043 oxo group Chemical group O=* 0.000 description 24
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 22
- 125000000623 heterocyclic group Chemical group 0.000 description 21
- 125000004193 piperazinyl group Chemical group 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 18
- 125000005842 heteroatom Chemical group 0.000 description 18
- 125000003386 piperidinyl group Chemical group 0.000 description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 13
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 13
- 125000004076 pyridyl group Chemical group 0.000 description 13
- 239000003814 drug Substances 0.000 description 12
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 125000003831 tetrazolyl group Chemical group 0.000 description 10
- 201000008827 tuberculosis Diseases 0.000 description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 9
- 125000002883 imidazolyl group Chemical group 0.000 description 9
- 125000002971 oxazolyl group Chemical group 0.000 description 9
- 125000005936 piperidyl group Chemical group 0.000 description 9
- 125000003003 spiro group Chemical group 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 7
- 125000000168 pyrrolyl group Chemical group 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- 239000000814 tuberculostatic agent Substances 0.000 description 7
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 6
- 125000000335 thiazolyl group Chemical group 0.000 description 6
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical group C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 5
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 5
- 229960001225 rifampicin Drugs 0.000 description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical class 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 206010067484 Adverse reaction Diseases 0.000 description 4
- 208000035143 Bacterial infection Diseases 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000006838 adverse reaction Effects 0.000 description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 208000022362 bacterial infectious disease Diseases 0.000 description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 229960003350 isoniazid Drugs 0.000 description 4
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 125000000160 oxazolidinyl group Chemical group 0.000 description 4
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 4
- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229960000285 ethambutol Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 208000019423 liver disease Diseases 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 229960005322 streptomycin Drugs 0.000 description 3
- 125000005505 thiomorpholino group Chemical group 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical group C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- 241000186367 Mycobacterium avium Species 0.000 description 2
- 241000186365 Mycobacterium fortuitum Species 0.000 description 2
- 241000186364 Mycobacterium intracellulare Species 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000005236 alkanoylamino group Chemical group 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005484 neopentoxy group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000007918 pathogenicity Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 229960005206 pyrazinamide Drugs 0.000 description 2
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 2
- 125000005920 sec-butoxy group Chemical group 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- LYOIGYXSILNCGD-HSZRJFAPSA-N (2r)-2-[[4-[4-(4-chlorophenyl)piperazin-1-yl]phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1C1=CC=C(Cl)C=C1 LYOIGYXSILNCGD-HSZRJFAPSA-N 0.000 description 1
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 description 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 1
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical group C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- AIUOUEPKBRDPLG-UHFFFAOYSA-N 1,3-benzoxathiole Chemical group C1=CC=C2SCOC2=C1 AIUOUEPKBRDPLG-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- FDUVAPUGTURJLJ-UHFFFAOYSA-N 1,4-dioxa-2-azaspiro[4.5]decane Chemical group O1CNOC11CCCCC1 FDUVAPUGTURJLJ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
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- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/06—Antibacterial agents for tuberculosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002298259 | 2002-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200501033B true ZA200501033B (en) | 2006-06-28 |
Family
ID=32089299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200501033A ZA200501033B (en) | 2002-10-11 | 2005-02-03 | 2,3,-dihydro-6-nitroimidazoÄ2,1-BÜoxazoles |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7262212B2 (sr) |
| EP (2) | EP2570418A3 (sr) |
| JP (1) | JP4186065B2 (sr) |
| KR (1) | KR100723847B1 (sr) |
| CN (4) | CN101255170A (sr) |
| AR (4) | AR041198A1 (sr) |
| AU (1) | AU2003272979B2 (sr) |
| BE (1) | BE2014C053I2 (sr) |
| BR (1) | BRPI0314344B8 (sr) |
| CA (1) | CA2497569C (sr) |
| CY (2) | CY1113578T1 (sr) |
| DK (1) | DK1555267T3 (sr) |
| ES (1) | ES2400179T3 (sr) |
| FR (1) | FR14C0066I2 (sr) |
| HK (2) | HK1085463A1 (sr) |
| HU (1) | HUS1400046I1 (sr) |
| LU (1) | LU92517I2 (sr) |
| MX (1) | MXPA05003674A (sr) |
| MY (1) | MY139244A (sr) |
| PL (3) | PL217919B1 (sr) |
| PT (1) | PT1555267E (sr) |
| RU (1) | RU2326121C3 (sr) |
| SI (1) | SI1555267T1 (sr) |
| TW (1) | TWI347946B (sr) |
| UA (1) | UA83200C2 (sr) |
| WO (1) | WO2004033463A1 (sr) |
| ZA (1) | ZA200501033B (sr) |
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1330444B1 (en) | 2000-11-01 | 2011-03-23 | Millennium Pharmaceuticals, Inc. | Nitrogenous heterocyclic compounds and process for making them |
| BR0313566A (pt) | 2002-10-15 | 2005-06-21 | Otsuka Pharma Co Ltd | Composto de 4-nitroimidazol 1-substituìdo, método para preparar um composto de 4-nitroimidazol, método para preparar um composto de 4-nitroimidazol 1-substituìdo, derivado de 4-nitroimidazol, e, composto |
| JP4761756B2 (ja) * | 2003-10-31 | 2011-08-31 | 大塚製薬株式会社 | ２，３−ジヒドロイミダゾ［２，１−ｂ］オキサゾ−ル化合物 |
| KR100851802B1 (ko) * | 2003-10-31 | 2008-08-13 | 오쓰까 세이야꾸 가부시키가이샤 | 결핵의 치료를 위한2,3-디히드로-6-니트로이미다조[2,1-ｂ]옥사졸 화합물 |
| TWI300409B (en) | 2004-02-18 | 2008-09-01 | Otsuka Pharma Co Ltd | Method for producing 4-nitroimidazole compound |
| EP1731518B1 (en) | 2004-03-31 | 2014-06-25 | Nippon Soda Co., Ltd. | Cyclic amine compound and pest control agent |
| JP4789966B2 (ja) * | 2004-04-09 | 2011-10-12 | 大塚製薬株式会社 | 医薬組成物 |
| JP4787529B2 (ja) * | 2004-04-09 | 2011-10-05 | 大塚製薬株式会社 | 医薬組成物 |
| EP1896453B1 (en) * | 2005-06-20 | 2009-12-02 | Schering Corporation | Carbon-linked substituted piperidines and derivatives thereof useful as histamine h3 antagonists |
| KR101294921B1 (ko) * | 2005-07-28 | 2013-08-08 | 오츠카 세이야쿠 가부시키가이샤 | 2,3-디히드로-6-니트로이미다조〔2,1-ｂ〕옥사졸 유도체 함유 제약 조성물 |
| TW201434467A (zh) * | 2005-10-05 | 2014-09-16 | Otsuka Pharma Co Ltd | 抗結核治療藥物及含彼之套組 |
| JP5105818B2 (ja) * | 2005-10-05 | 2012-12-26 | 大塚製薬株式会社 | 医薬組成物 |
| SI1947098T1 (sl) * | 2005-10-06 | 2012-02-29 | Nippon Soda Co | Ciklične aminske spojine in sredstvo za zatiranje škodljivcev |
| TW200800268A (en) * | 2005-11-04 | 2008-01-01 | Otsuka Pharma Co Ltd | Medicinal composition showing improved drug absorbability |
| AU2006333522A1 (en) * | 2005-12-21 | 2007-07-12 | Decode Genetics, Ehf. | Biaryl nitrogen heterocycle inhibitors of LTA4H for treating inflammation |
| EP1986637A1 (en) * | 2006-02-13 | 2008-11-05 | Laboratoires Serono SA | Sulfonamide derivatives for the treatment of bacterial infections |
| JP2007297305A (ja) * | 2006-04-28 | 2007-11-15 | Daiso Co Ltd | Ｎ−（２，３−エポキシ−２−メチルプロピル）フタルイミドの製造法 |
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| AR070301A1 (es) * | 2007-05-08 | 2010-03-31 | Otsuka Pharma Co Ltd | Compuesto epoxi y metodo para producir el mismo |
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| US5668127A (en) | 1995-06-26 | 1997-09-16 | Pathogenesis Corporation | Nitroimidazole antibacterial compounds and methods of use thereof |
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