JP2009520804A5 - - Google Patents
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- Publication number
- JP2009520804A5 JP2009520804A5 JP2008546665A JP2008546665A JP2009520804A5 JP 2009520804 A5 JP2009520804 A5 JP 2009520804A5 JP 2008546665 A JP2008546665 A JP 2008546665A JP 2008546665 A JP2008546665 A JP 2008546665A JP 2009520804 A5 JP2009520804 A5 JP 2009520804A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- oxazino
- spiro
- tetrahydro
- quinoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 36
- 238000000034 method Methods 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 10
- -1 —OR 6 Chemical group 0.000 claims 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 150000002170 ethers Chemical class 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- AOGRSAIQGKKYQV-UHFFFAOYSA-N spiro[1,3-diazinane-5,5'-6h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C11C2=COC=CN2C2=CC=CC=C2C1 AOGRSAIQGKKYQV-UHFFFAOYSA-N 0.000 claims 3
- SSQYBZNZBNXQNO-LIBAHTEVSA-N (2'r,4's,4'as)-9',10'-difluoro-2',4'-dimethyl-8'-(5-methylpyrazin-2-yl)spiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=C(F)C(F)=C(C=C4C1)C=1N=CC(C)=NC=1)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O SSQYBZNZBNXQNO-LIBAHTEVSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical compound CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 150000003216 pyrazines Chemical class 0.000 claims 2
- WJWQTPKPCGYBAH-KSRUKNBBSA-N (2'r,4's,4'as)-8'-(5-aminopyrazin-2-yl)-9',10'-difluoro-2',4'-dimethylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=C(F)C(F)=C(C=C4C1)C=1N=CC(N)=NC=1)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O WJWQTPKPCGYBAH-KSRUKNBBSA-N 0.000 claims 1
- XHSMJCDFOZQTSG-KSRUKNBBSA-N (2'r,4's,4'as)-8'-(5-bromopyrazin-2-yl)-9',10'-difluoro-2',4'-dimethylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=C(F)C(F)=C(C=C4C1)C=1N=CC(Br)=NC=1)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O XHSMJCDFOZQTSG-KSRUKNBBSA-N 0.000 claims 1
- AESOLELBNNKZEG-RMDKCXRXSA-N (2'r,4's,4'as)-8'-(5-ethoxypyrazin-2-yl)-9',10'-difluoro-2',4'-dimethylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C1=NC(OCC)=CN=C1C(C(=C1F)F)=CC2=C1N1C[C@@H](C)O[C@@H](C)[C@@H]1C1(C(NC(=O)NC1=O)=O)C2 AESOLELBNNKZEG-RMDKCXRXSA-N 0.000 claims 1
- SYGPUHHACFBOLF-GPHJXTMHSA-N (2'r,4's,4'as)-9',10'-difluoro-2',4'-dimethyl-8'-pyrazin-2-ylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=C(F)C(F)=C(C=C4C1)C=1N=CC=NC=1)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O SYGPUHHACFBOLF-GPHJXTMHSA-N 0.000 claims 1
- PBNUIWUNGLZCCQ-AUSHCKSDSA-N (2'r,4's,4'as)-9',10'-difluoro-8'-(5-methoxypyrazin-2-yl)-2',4'-dimethylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C1=NC(OC)=CN=C1C(C(=C1F)F)=CC2=C1N1C[C@@H](C)O[C@@H](C)[C@@H]1C1(C(NC(=O)NC1=O)=O)C2 PBNUIWUNGLZCCQ-AUSHCKSDSA-N 0.000 claims 1
- HRTLIFOGJJTTBX-CRTZDJKQSA-N (2's,4'r,4'ar)-1,3-bis(bromomethyl)-9',10'-difluoro-2',4'-dimethyl-8'-pyrazin-2-ylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@H]3N(C4=C(F)C(F)=C(C=C4C1)C=1N=CC=NC=1)C[C@@H](O[C@@H]3C)C)C(=O)N(CBr)C(=O)N(CBr)C2=O HRTLIFOGJJTTBX-CRTZDJKQSA-N 0.000 claims 1
- SYGPUHHACFBOLF-GBNMTWHSSA-N (2's,4'r,4'ar)-9',10'-difluoro-2',4'-dimethyl-8'-pyrazin-2-ylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@H]3N(C4=C(F)C(F)=C(C=C4C1)C=1N=CC=NC=1)C[C@@H](O[C@@H]3C)C)C(=O)NC(=O)NC2=O SYGPUHHACFBOLF-GBNMTWHSSA-N 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000000539 amino acid group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 230000003385 bacteriostatic effect Effects 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 238000010537 deprotonation reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108090000765 processed proteins & peptides Chemical group 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75326205P | 2005-12-22 | 2005-12-22 | |
| US60/753,262 | 2005-12-22 | ||
| PCT/IB2006/003641 WO2007072151A1 (en) | 2005-12-22 | 2006-12-11 | 8-pyrazinyl-s-spiropyrimidinetrione-oxazinoquinoline derivatives as antibacterial agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009520804A JP2009520804A (ja) | 2009-05-28 |
| JP2009520804A5 true JP2009520804A5 (https=) | 2009-09-24 |
| JP5513743B2 JP5513743B2 (ja) | 2014-06-04 |
Family
ID=37872452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008546665A Expired - Fee Related JP5513743B2 (ja) | 2005-12-22 | 2006-12-11 | 抗菌剤としての８−ピラジニル−ｓ−スピロピリミジントリオン−オキサジノキノリン誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7557100B2 (https=) |
| EP (2) | EP1971612A1 (https=) |
| JP (1) | JP5513743B2 (https=) |
| AR (1) | AR058701A1 (https=) |
| CA (1) | CA2634644A1 (https=) |
| DO (1) | DOP2006000268A (https=) |
| GT (1) | GT200600520A (https=) |
| NL (1) | NL2000373C2 (https=) |
| PE (1) | PE20071137A1 (https=) |
| TW (1) | TW200734344A (https=) |
| UY (1) | UY30030A1 (https=) |
| WO (1) | WO2007072151A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2552682T3 (es) | 2003-03-10 | 2015-12-01 | Merck Sharp & Dohme Corp. | Agentes antibacterianos novedosos |
| DOP2006000268A (es) * | 2005-12-22 | 2007-07-31 | Pfizer Prod Inc | Agentes antibacterianos |
| US20100261719A1 (en) * | 2007-07-02 | 2010-10-14 | Gregory Steven Basarab | Chemical compounds |
| CA2729923A1 (en) * | 2007-07-06 | 2009-01-15 | Aarhus Universitet | Dehydrated chitosan nanoparticles |
| CN101687871A (zh) | 2007-07-16 | 2010-03-31 | 阿斯利康(瑞典)有限公司 | 用作抗菌剂的螺缩合巴比妥酸衍生物 |
| CN105732745A (zh) | 2007-10-25 | 2016-07-06 | 森普拉制药公司 | 大环内酯类抗菌剂的制备方法 |
| US9040528B2 (en) | 2008-10-14 | 2015-05-26 | Astrazeneca Ab | Chemical compounds 542 |
| CN102245605B (zh) * | 2008-10-14 | 2016-01-27 | 阿斯利康(瑞典)有限公司 | 用于治疗细菌感染的稠合、螺环杂芳族化合物 |
| AU2009308182B2 (en) * | 2008-10-24 | 2016-05-19 | Cempra Pharmaceuticals, Inc. | Biodefenses using triazole-containing macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| US9480679B2 (en) | 2009-09-10 | 2016-11-01 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and MAC diseases |
| DK2550286T3 (en) | 2010-03-22 | 2016-02-29 | Cempra Pharmaceuticals Inc | CRYSTALLINE FORMS OF A MACROLID AND APPLICATIONS THEREOF |
| CN105198944B (zh) | 2010-05-20 | 2018-06-01 | 森普拉制药公司 | 制备大环内酯和酮内酯及其中间体的方法 |
| EP2613630A4 (en) | 2010-09-10 | 2014-01-15 | Cempra Pharmaceuticals Inc | HYDROGEN BOND FOR THE PREPARATION OF FLUOROCHETOLIDES FOR THE TREATMENT OF DISEASES |
| MX2014011537A (es) | 2012-03-27 | 2015-02-10 | Cempra Pharmaceuticals Inc | Formulaciones parenterales para la administracion de antibioticos macrolidos. |
| US8952149B2 (en) | 2012-09-26 | 2015-02-10 | Zoetis Llc | Tricyclic tetrahydroquinoline antibacterial agents |
| US8889671B2 (en) | 2013-01-23 | 2014-11-18 | Astrazeneca Ab | Compounds and methods for treating bacterial infections |
| HK1217665A1 (zh) | 2013-03-14 | 2017-01-20 | 森普拉制药公司 | 用於治療呼吸道疾病的方法及其製劑 |
| RU2015138797A (ru) | 2013-03-15 | 2017-04-24 | Семпра Фармасьютикалс, Инк. | Конвергентные способы получения макролидных антибактериальных агентов |
| SG10201906842WA (en) | 2014-05-29 | 2019-08-27 | Entasis Therapeutics Ltd | Fused, spirocyclic heteroaromatic compounds for the treatment of bacterial infections |
| UY36851A (es) | 2015-08-16 | 2017-03-31 | Glaxosmithkline Ip Dev Ltd | Compuestos para uso en aplicaciones antibacterianas |
| KR102717819B1 (ko) | 2017-07-28 | 2024-10-14 | 다케다 야쿠힌 고교 가부시키가이샤 | Tyk2 억제제 및 이의 용도 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011860A (en) | 1986-04-11 | 1991-04-30 | Schering Corporation | Aryl-substituted naphthyridine and pyridopyrazine derivatives and their use in treating hyperproliferative skin diseases |
| DE19502178A1 (de) | 1994-01-27 | 1995-08-03 | Hoechst Ag | Thiadiazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Vorprodukte zur Herstellung von Flüssigkristallen |
| US6608081B2 (en) * | 1999-08-12 | 2003-08-19 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| CN1501937A (zh) | 2000-10-26 | 2004-06-02 | �Ʒ� | 螺-嘧啶-2,4,6-三酮金属蛋白酶抑制剂 |
| ATE315038T1 (de) * | 2001-05-30 | 2006-02-15 | Warner Lambert Co | Antibakterielle mittel |
| AU2003228701A1 (en) | 2002-04-25 | 2003-11-10 | Bristol-Myers Squibb Company | Spirobarbituric acid derivatives useful as inhibitors of matrix metalloproteases |
| US7208490B2 (en) | 2002-10-07 | 2007-04-24 | Pharmacia & Upjohn Company Llc | Tricyclic tetrahydroquinoline antibacterial agents |
| CA2606847A1 (en) | 2005-05-09 | 2006-11-16 | Warner-Lambert Company Llc | Antibacterial agents |
| DOP2006000268A (es) * | 2005-12-22 | 2007-07-31 | Pfizer Prod Inc | Agentes antibacterianos |
-
2006
- 2006-11-29 DO DO2006000268A patent/DOP2006000268A/es unknown
- 2006-12-11 WO PCT/IB2006/003641 patent/WO2007072151A1/en not_active Ceased
- 2006-12-11 CA CA002634644A patent/CA2634644A1/en not_active Abandoned
- 2006-12-11 EP EP06831728A patent/EP1971612A1/en not_active Withdrawn
- 2006-12-11 JP JP2008546665A patent/JP5513743B2/ja not_active Expired - Fee Related
- 2006-12-11 EP EP13151044.8A patent/EP2620439A1/en not_active Withdrawn
- 2006-12-13 NL NL2000373A patent/NL2000373C2/nl not_active IP Right Cessation
- 2006-12-19 UY UY30030A patent/UY30030A1/es not_active Application Discontinuation
- 2006-12-19 US US11/641,215 patent/US7557100B2/en not_active Expired - Fee Related
- 2006-12-20 AR ARP060105669A patent/AR058701A1/es unknown
- 2006-12-20 PE PE2006001657A patent/PE20071137A1/es not_active Application Discontinuation
- 2006-12-20 GT GT200600520A patent/GT200600520A/es unknown
- 2006-12-21 TW TW095148255A patent/TW200734344A/zh unknown
-
2009
- 2009-07-15 US US12/503,123 patent/US20090275536A1/en not_active Abandoned
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