JP2017513892A5 - - Google Patents
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- Publication number
- JP2017513892A5 JP2017513892A5 JP2016564087A JP2016564087A JP2017513892A5 JP 2017513892 A5 JP2017513892 A5 JP 2017513892A5 JP 2016564087 A JP2016564087 A JP 2016564087A JP 2016564087 A JP2016564087 A JP 2016564087A JP 2017513892 A5 JP2017513892 A5 JP 2017513892A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydroxy
- methylsulfonyl
- propanamide
- dihydroisoxazol
- 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
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 15
- -1 amino, hydroxy Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 241000588921 Enterobacteriaceae Species 0.000 claims 4
- 241000588771 Morganella <proteobacterium> Species 0.000 claims 4
- 241000607142 Salmonella Species 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- 241000588724 Escherichia coli Species 0.000 claims 3
- 241000588653 Neisseria Species 0.000 claims 3
- 241000588769 Proteus <enterobacteria> Species 0.000 claims 3
- 241000607720 Serratia Species 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 241001673062 Achromobacter xylosoxidans Species 0.000 claims 2
- 241000589291 Acinetobacter Species 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 241000046135 Cedecea Species 0.000 claims 2
- 241000607473 Edwardsiella <enterobacteria> Species 0.000 claims 2
- 241000588914 Enterobacter Species 0.000 claims 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims 2
- 241000606790 Haemophilus Species 0.000 claims 2
- 241000588748 Klebsiella Species 0.000 claims 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 2
- 241000588768 Providencia Species 0.000 claims 2
- 241000122973 Stenotrophomonas maltophilia Species 0.000 claims 2
- 241000607734 Yersinia <bacteria> Species 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229960002227 clindamycin Drugs 0.000 claims 2
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- MMRINLZOZVAPDZ-LSGRDSQZSA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;chloride Chemical compound Cl.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 MMRINLZOZVAPDZ-LSGRDSQZSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims 1
- 241000606125 Bacteroides Species 0.000 claims 1
- 241000588807 Bordetella Species 0.000 claims 1
- 241001453380 Burkholderia Species 0.000 claims 1
- 241000589513 Burkholderia cepacia Species 0.000 claims 1
- 241000588923 Citrobacter Species 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 241000589601 Francisella Species 0.000 claims 1
- 241000589248 Legionella Species 0.000 claims 1
- 208000007764 Legionnaires' Disease Diseases 0.000 claims 1
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims 1
- 241000588621 Moraxella Species 0.000 claims 1
- 108010040201 Polymyxins Proteins 0.000 claims 1
- 241000589516 Pseudomonas Species 0.000 claims 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims 1
- 241000607768 Shigella Species 0.000 claims 1
- 239000004098 Tetracycline Substances 0.000 claims 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims 1
- 108010059993 Vancomycin Proteins 0.000 claims 1
- 241000607598 Vibrio Species 0.000 claims 1
- 229960004821 amikacin Drugs 0.000 claims 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims 1
- 229960000723 ampicillin Drugs 0.000 claims 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical group C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims 1
- 229960004099 azithromycin Drugs 0.000 claims 1
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims 1
- 229960003644 aztreonam Drugs 0.000 claims 1
- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229960002100 cefepime Drugs 0.000 claims 1
- 229960004261 cefotaxime Drugs 0.000 claims 1
- AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 claims 1
- 229960004755 ceftriaxone Drugs 0.000 claims 1
- VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229960003276 erythromycin Drugs 0.000 claims 1
- 229960002182 imipenem Drugs 0.000 claims 1
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 210000000936 intestine Anatomy 0.000 claims 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 1
- 229960003376 levofloxacin Drugs 0.000 claims 1
- 229960002260 meropenem Drugs 0.000 claims 1
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229940056360 penicillin g Drugs 0.000 claims 1
- 229960002292 piperacillin Drugs 0.000 claims 1
- WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 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 claims 1
- 229960001225 rifampicin Drugs 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 235000019364 tetracycline Nutrition 0.000 claims 1
- 229940040944 tetracyclines Drugs 0.000 claims 1
- 150000003522 tetracyclines Chemical class 0.000 claims 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims 1
- 229960004659 ticarcillin Drugs 0.000 claims 1
- 229960000707 tobramycin Drugs 0.000 claims 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims 1
- 229960003165 vancomycin Drugs 0.000 claims 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims 1
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461982467P | 2014-04-22 | 2014-04-22 | |
| US61/982,467 | 2014-04-22 | ||
| PCT/US2015/027009 WO2015164458A1 (en) | 2014-04-22 | 2015-04-22 | Isoxazoline hydroxamic acid derivatives as lpxc inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017513892A JP2017513892A (ja) | 2017-06-01 |
| JP2017513892A5 true JP2017513892A5 (https=) | 2018-05-24 |
| JP6514716B2 JP6514716B2 (ja) | 2019-05-15 |
Family
ID=53059459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016564087A Expired - Fee Related JP6514716B2 (ja) | 2014-04-22 | 2015-04-22 | ＬｐｘＣ阻害剤としてのイソオキサゾリンヒドロキサム酸誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9637482B2 (https=) |
| EP (1) | EP3134401B1 (https=) |
| JP (1) | JP6514716B2 (https=) |
| CN (1) | CN106573924B (https=) |
| ES (1) | ES2687393T3 (https=) |
| WO (1) | WO2015164458A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019501896A (ja) * | 2015-12-08 | 2019-01-24 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 抗菌化合物としての置換ベンザジノン |
| SG11201810656WA (en) | 2016-06-14 | 2018-12-28 | Novartis Ag | Crystalline form of (r)-4-(5-(cyclopropylethynyl)isoxazol-3-yl)-n-hydroxy-2-methyl-2-(methylsulfonyl)butanamide as an antibacterial agent |
| AU2017337946B2 (en) * | 2016-09-28 | 2020-05-07 | Dong-A St Co., Ltd. | Tetrahydropyridine derivatives and their use as antibacterial agents |
| TW202039478A (zh) * | 2018-11-21 | 2020-11-01 | 日商大正製藥股份有限公司 | 新穎咪唑衍生物 |
| KR20210113648A (ko) * | 2019-01-06 | 2021-09-16 | 소마젠 인크 | Ｈｔｒａ 저해제 및 ｃａｇａ 저해제 및 이의 용도 |
| WO2024067812A1 (zh) * | 2022-09-28 | 2024-04-04 | 浙江海正药业股份有限公司 | 芳香乙炔类衍生物及其制备方法和用途 |
| CN120569379A (zh) * | 2023-01-19 | 2025-08-29 | 浙江海正药业股份有限公司 | 芳香乙炔类衍生物及其制备方法和用途 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE154932T1 (de) * | 1993-11-26 | 1997-07-15 | Pfizer | Isoxazolinverbindungen als entzündungshemmende mittel |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| US7125870B2 (en) | 2002-11-06 | 2006-10-24 | Bristol-Myers Squibb Company | Isoxazoline derivatives as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme |
| CA2851462A1 (en) | 2003-01-08 | 2004-07-29 | University Of Washington | Antibacterial agents |
| WO2010032147A2 (en) | 2008-09-19 | 2010-03-25 | Pfizer Inc. | Hydroxamic acid derivatives useful as antibacterial agents |
| WO2011045703A2 (en) * | 2009-10-13 | 2011-04-21 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| DK2512474T3 (en) | 2009-12-16 | 2014-12-01 | Pfizer | N-linked hydroxamic acid derivatives which can be used as antibacterial agents |
| MA34963B1 (fr) | 2011-03-07 | 2014-03-01 | Pfizer | Derives de fluoro-pyridinone utiles en tant qu'agents antibacteriens |
| WO2012137094A1 (en) * | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Isoxazole derivatives useful as antibacterial agents |
| KR20120137094A (ko) * | 2011-06-10 | 2012-12-20 | 현대자동차주식회사 | 차량용 소음기 |
| WO2014160649A1 (en) | 2013-03-29 | 2014-10-02 | Novartis Ag | Hydroxamic acid derivatives as lpxc inhibitors for the treatment of bacterial infections |
-
2015
- 2015-04-22 EP EP15721435.4A patent/EP3134401B1/en not_active Not-in-force
- 2015-04-22 ES ES15721435.4T patent/ES2687393T3/es active Active
- 2015-04-22 CN CN201580033532.8A patent/CN106573924B/zh not_active Expired - Fee Related
- 2015-04-22 JP JP2016564087A patent/JP6514716B2/ja not_active Expired - Fee Related
- 2015-04-22 US US15/304,044 patent/US9637482B2/en not_active Expired - Fee Related
- 2015-04-22 WO PCT/US2015/027009 patent/WO2015164458A1/en not_active Ceased
-
2017
- 2017-03-09 US US15/454,187 patent/US9718792B2/en not_active Expired - Fee Related
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