JP2003503505A5 - - Google Patents
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- Publication number
- JP2003503505A5 JP2003503505A5 JP2001507847A JP2001507847A JP2003503505A5 JP 2003503505 A5 JP2003503505 A5 JP 2003503505A5 JP 2001507847 A JP2001507847 A JP 2001507847A JP 2001507847 A JP2001507847 A JP 2001507847A JP 2003503505 A5 JP2003503505 A5 JP 2003503505A5
- Authority
- JP
- Japan
- Prior art keywords
- heteroaryl
- aryl
- group
- alkyl
- aralkyl
- 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
- 125000001072 heteroaryl group Chemical group 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 15
- -1 5-dimethylamino-1-naphthyl Chemical group 0.000 claims description 13
- 239000000651 prodrug Substances 0.000 claims description 13
- 229940002612 prodrug Drugs 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 239000004305 biphenyl Chemical group 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000002132 β-lactam antibiotic Substances 0.000 claims 1
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 1
- BLZKSRBAQDZAIX-UHFFFAOYSA-N Cc1cc(cccc2)c2[s]1 Chemical compound Cc1cc(cccc2)c2[s]1 BLZKSRBAQDZAIX-UHFFFAOYSA-N 0.000 description 28
- 0 CS(N(*)C(*)P(*)(*)=O)O Chemical compound CS(N(*)C(*)P(*)(*)=O)O 0.000 description 26
- BQUWGTCEDHMBRB-UHFFFAOYSA-N Cc1cc(c(Cl)ccc2Cl)c2[s]1 Chemical compound Cc1cc(c(Cl)ccc2Cl)c2[s]1 BQUWGTCEDHMBRB-UHFFFAOYSA-N 0.000 description 12
- REIVHYDACHXPNH-UHFFFAOYSA-N N#Cc(c(F)c1)ccc1O Chemical compound N#Cc(c(F)c1)ccc1O REIVHYDACHXPNH-UHFFFAOYSA-N 0.000 description 7
- XKAHNODIWXKQHL-UHFFFAOYSA-N CC(SC1=C(CC2)Cl)=CC1=C2Cl Chemical compound CC(SC1=C(CC2)Cl)=CC1=C2Cl XKAHNODIWXKQHL-UHFFFAOYSA-N 0.000 description 5
- ZEFMBAFMCSYJOO-UHFFFAOYSA-N [O-][N+](c(c(C(F)(F)F)c1)ccc1O)=O Chemical compound [O-][N+](c(c(C(F)(F)F)c1)ccc1O)=O ZEFMBAFMCSYJOO-UHFFFAOYSA-N 0.000 description 4
- TUIDQYRZDZRHPQ-UHFFFAOYSA-N Oc1cncc(Cl)c1 Chemical compound Oc1cncc(Cl)c1 TUIDQYRZDZRHPQ-UHFFFAOYSA-N 0.000 description 3
- OLWCVKIIIHFYEV-UHFFFAOYSA-N CC(SC1CCC2)=CC1C2OC Chemical compound CC(SC1CCC2)=CC1C2OC OLWCVKIIIHFYEV-UHFFFAOYSA-N 0.000 description 2
- PLSKGDOOMXUQEV-UHFFFAOYSA-N CC1=C(C)SC2=CCCC=C12 Chemical compound CC1=C(C)SC2=CCCC=C12 PLSKGDOOMXUQEV-UHFFFAOYSA-N 0.000 description 2
- WLHCBQAPPJAULW-UHFFFAOYSA-N Cc(cc1)ccc1S Chemical compound Cc(cc1)ccc1S WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 2
- PIIZYNQECPTVEO-UHFFFAOYSA-N Cc1cc(O)ccc1[N+]([O-])=O Chemical compound Cc1cc(O)ccc1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 description 2
- ZJNKDSJWCWYSOJ-UHFFFAOYSA-N Cc1cc(cc(cc2Cl)Cl)c2[s]1 Chemical compound Cc1cc(cc(cc2Cl)Cl)c2[s]1 ZJNKDSJWCWYSOJ-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Cc1ccc(C)cc1 Chemical compound Cc1ccc(C)cc1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- CVNOWLNNPYYEOH-UHFFFAOYSA-N N#Cc(cc1)ccc1O Chemical compound N#Cc(cc1)ccc1O CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 2
- NDACNGSDAFKTGE-UHFFFAOYSA-N Oc1cccc(Nc2ccccc2)c1 Chemical compound Oc1cccc(Nc2ccccc2)c1 NDACNGSDAFKTGE-UHFFFAOYSA-N 0.000 description 2
- ORPHLVJBJOCHBR-UHFFFAOYSA-N [O-][N+](c(cc1)cc(F)c1O)=O Chemical compound [O-][N+](c(cc1)cc(F)c1O)=O ORPHLVJBJOCHBR-UHFFFAOYSA-N 0.000 description 2
- CYGBOHMVSBKTEZ-UHFFFAOYSA-N C=Cc(c(C#N)c1)ccc1-c(cc1)ccc1O Chemical compound C=Cc(c(C#N)c1)ccc1-c(cc1)ccc1O CYGBOHMVSBKTEZ-UHFFFAOYSA-N 0.000 description 1
- BYIKGUCVIJYTDZ-UHFFFAOYSA-N C=[O]c(c1ncccc1c(Cl)c1)c1Cl Chemical compound C=[O]c(c1ncccc1c(Cl)c1)c1Cl BYIKGUCVIJYTDZ-UHFFFAOYSA-N 0.000 description 1
- KTLSJYNXAJFAJK-UHFFFAOYSA-N CC(C(C1)C1C1=C(CC2)Cl)=CC1=C2Cl Chemical compound CC(C(C1)C1C1=C(CC2)Cl)=CC1=C2Cl KTLSJYNXAJFAJK-UHFFFAOYSA-N 0.000 description 1
- CDFYHOWHJFDGEL-UHFFFAOYSA-N CC(C12CC1)=Cc1c2c(Cl)ccc1Cl Chemical compound CC(C12CC1)=Cc1c2c(Cl)ccc1Cl CDFYHOWHJFDGEL-UHFFFAOYSA-N 0.000 description 1
- LRPNUYLNUSSJOW-UHFFFAOYSA-N CC(SC1(C2CC3)C2Cl)=NC1=C3Cl Chemical compound CC(SC1(C2CC3)C2Cl)=NC1=C3Cl LRPNUYLNUSSJOW-UHFFFAOYSA-N 0.000 description 1
- CISRCEULUWTPKG-UHFFFAOYSA-N CC(SC1=C(CC2)Cl)=NC1=C2Cl Chemical compound CC(SC1=C(CC2)Cl)=NC1=C2Cl CISRCEULUWTPKG-UHFFFAOYSA-N 0.000 description 1
- POWYHFJSURREEI-UHFFFAOYSA-N CC(SC1=C(CC2)[ClH]C)=CC1=C2Cl Chemical compound CC(SC1=C(CC2)[ClH]C)=CC1=C2Cl POWYHFJSURREEI-UHFFFAOYSA-N 0.000 description 1
- NHGKSOKOMJCNKT-UHFFFAOYSA-N CC1(C2C1)Sc1c2c(Cl)ccc1Cl Chemical compound CC1(C2C1)Sc1c2c(Cl)ccc1Cl NHGKSOKOMJCNKT-UHFFFAOYSA-N 0.000 description 1
- MTXOEZSEPDKTKA-UHFFFAOYSA-N CCc(cc1)cc(F)c1[N+]([O-])=O Chemical compound CCc(cc1)cc(F)c1[N+]([O-])=O MTXOEZSEPDKTKA-UHFFFAOYSA-N 0.000 description 1
- IRXFFUIDSQITGU-YNODCEANSA-N C[C@@H]1C=CC(COC(C(C=C2)=CCC2O)=O)=CC1 Chemical compound C[C@@H]1C=CC(COC(C(C=C2)=CCC2O)=O)=CC1 IRXFFUIDSQITGU-YNODCEANSA-N 0.000 description 1
- ACHMHHCOSAKQSS-UHFFFAOYSA-N Cc1c(C)[s]c2c1cccc2 Chemical compound Cc1c(C)[s]c2c1cccc2 ACHMHHCOSAKQSS-UHFFFAOYSA-N 0.000 description 1
- MJJZKKADFRELSY-UHFFFAOYSA-N Cc1cc(C(CCC2)OC)c2[s]1 Chemical compound Cc1cc(C(CCC2)OC)c2[s]1 MJJZKKADFRELSY-UHFFFAOYSA-N 0.000 description 1
- UTFSSVWJVFAACX-UHFFFAOYSA-N Cc1cc(cc(cc2)Br)c2[s]1 Chemical compound Cc1cc(cc(cc2)Br)c2[s]1 UTFSSVWJVFAACX-UHFFFAOYSA-N 0.000 description 1
- JNICXVHWTSHDHF-UHFFFAOYSA-M Cc1cc(cc(cc2)[O-])c2[s]1 Chemical compound Cc1cc(cc(cc2)[O-])c2[s]1 JNICXVHWTSHDHF-UHFFFAOYSA-M 0.000 description 1
- TZRLJRADEMLICJ-UHFFFAOYSA-N Cc1cc2cc(Cl)ccc2[s]1 Chemical compound Cc1cc2cc(Cl)ccc2[s]1 TZRLJRADEMLICJ-UHFFFAOYSA-N 0.000 description 1
- RKQWKIZYDYKFNE-UHFFFAOYSA-N Cc1cc2ncccc2[s]1 Chemical compound Cc1cc2ncccc2[s]1 RKQWKIZYDYKFNE-UHFFFAOYSA-N 0.000 description 1
- BKCMYFAEMBQFQZ-UHFFFAOYSA-N Cc1ccc(CCOC(C(CC2)CCC2O)=O)cc1 Chemical compound Cc1ccc(CCOC(C(CC2)CCC2O)=O)cc1 BKCMYFAEMBQFQZ-UHFFFAOYSA-N 0.000 description 1
- XCALAYIRFYALSX-UHFFFAOYSA-N Cc1nc(cc(cc2)Cl)c2[s]1 Chemical compound Cc1nc(cc(cc2)Cl)c2[s]1 XCALAYIRFYALSX-UHFFFAOYSA-N 0.000 description 1
- MDBVIOUGHSKRMT-UHFFFAOYSA-N N#Cc(cc1)c(C(F)(F)F)cc1O Chemical compound N#Cc(cc1)c(C(F)(F)F)cc1O MDBVIOUGHSKRMT-UHFFFAOYSA-N 0.000 description 1
- QHNXPYROGGWQDV-UHFFFAOYSA-N N#Cc(cc1)ccc1-c(cc1)cc(F)c1O Chemical compound N#Cc(cc1)ccc1-c(cc1)cc(F)c1O QHNXPYROGGWQDV-UHFFFAOYSA-N 0.000 description 1
- LYCMNMIPSJWQRL-UHFFFAOYSA-N N#Cc(cc1)ccc1-c1cc(O)ccc1 Chemical compound N#Cc(cc1)ccc1-c1cc(O)ccc1 LYCMNMIPSJWQRL-UHFFFAOYSA-N 0.000 description 1
- BRTMQANYAKIFNX-UHFFFAOYSA-N N#Cc(ccc(C1=CC(O)=CCC1)c1)c1F Chemical compound N#Cc(ccc(C1=CC(O)=CCC1)c1)c1F BRTMQANYAKIFNX-UHFFFAOYSA-N 0.000 description 1
- WLNIRLBZLAAEAQ-UHFFFAOYSA-N N#Cc1ccc(C2OC2)cc1 Chemical compound N#Cc1ccc(C2OC2)cc1 WLNIRLBZLAAEAQ-UHFFFAOYSA-N 0.000 description 1
- RVMSNUOZZCOXBA-JAIVOQCGSA-N N=C/C(/C(c(cccc1)c1O)=O)=C\Nc1ccccc1 Chemical compound N=C/C(/C(c(cccc1)c1O)=O)=C\Nc1ccccc1 RVMSNUOZZCOXBA-JAIVOQCGSA-N 0.000 description 1
- QXSAKPUBHTZHKW-UHFFFAOYSA-N NC(c(cc1)ccc1O)=O Chemical compound NC(c(cc1)ccc1O)=O QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 description 1
- XAZASYPEWLWTDH-UHFFFAOYSA-N NCCOC(C1=CCC(C2CC2)C=C1)=O Chemical compound NCCOC(C1=CCC(C2CC2)C=C1)=O XAZASYPEWLWTDH-UHFFFAOYSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N O=C(C(c1ccccc1)(c1ccccc1)N1)NC1=O Chemical compound O=C(C(c1ccccc1)(c1ccccc1)N1)NC1=O CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- HDTDFHIHKBOVMM-UHFFFAOYSA-N OC(c(cc1)ccc1O)Nc1ccccc1 Chemical compound OC(c(cc1)ccc1O)Nc1ccccc1 HDTDFHIHKBOVMM-UHFFFAOYSA-N 0.000 description 1
- CVXZLSJNMZNJQH-UHFFFAOYSA-N OCCOC(C1C=CC(O)=CC1)O Chemical compound OCCOC(C1C=CC(O)=CC1)O CVXZLSJNMZNJQH-UHFFFAOYSA-N 0.000 description 1
- GFHGEIJFEHZKHZ-UHFFFAOYSA-N OCCOC(c(cc1)ccc1O)=O Chemical compound OCCOC(c(cc1)ccc1O)=O GFHGEIJFEHZKHZ-UHFFFAOYSA-N 0.000 description 1
- CZXKAQGBZPKRHU-UHFFFAOYSA-N Oc(c(-c1ccn[o]1)c1)ccc1Br Chemical compound Oc(c(-c1ccn[o]1)c1)ccc1Br CZXKAQGBZPKRHU-UHFFFAOYSA-N 0.000 description 1
- AAJXJLYUWKMQNO-UHFFFAOYSA-N Oc(c(-c1ccn[o]1)c1)ccc1Cl Chemical compound Oc(c(-c1ccn[o]1)c1)ccc1Cl AAJXJLYUWKMQNO-UHFFFAOYSA-N 0.000 description 1
- CTQMJYWDVABFRZ-UHFFFAOYSA-N Oc(c1c2cccn1)ccc2Cl Chemical compound Oc(c1c2cccn1)ccc2Cl CTQMJYWDVABFRZ-UHFFFAOYSA-N 0.000 description 1
- DZFYHZOKUQKDFS-UHFFFAOYSA-N Oc(cc1)ccc1-c1cc(F)cc(F)c1 Chemical compound Oc(cc1)ccc1-c1cc(F)cc(F)c1 DZFYHZOKUQKDFS-UHFFFAOYSA-N 0.000 description 1
- QCNLNQVIZYSFBA-UHFFFAOYSA-N Oc(cc1)ccc1-c1n[nH]c(-c2ccccc2)c1 Chemical compound Oc(cc1)ccc1-c1n[nH]c(-c2ccccc2)c1 QCNLNQVIZYSFBA-UHFFFAOYSA-N 0.000 description 1
- FVQDRWUYZFPHLU-UHFFFAOYSA-N Oc(cc1)ccc1C(NCc1ccccc1)=O Chemical compound Oc(cc1)ccc1C(NCc1ccccc1)=O FVQDRWUYZFPHLU-UHFFFAOYSA-N 0.000 description 1
- ZIRGVXKBLCKLPE-UHFFFAOYSA-N Oc(cc1)ccc1C1=NCC(c2ccccc2)O1 Chemical compound Oc(cc1)ccc1C1=NCC(c2ccccc2)O1 ZIRGVXKBLCKLPE-UHFFFAOYSA-N 0.000 description 1
- WEUIJSDNBZVSNY-UHFFFAOYSA-N Oc(ccc(C(F)(F)F)c1)c1F Chemical compound Oc(ccc(C(F)(F)F)c1)c1F WEUIJSDNBZVSNY-UHFFFAOYSA-N 0.000 description 1
- DBDXTIAEVFSDNN-UHFFFAOYSA-N Oc(cccc1)c1-c1ccn[o]1 Chemical compound Oc(cccc1)c1-c1ccn[o]1 DBDXTIAEVFSDNN-UHFFFAOYSA-N 0.000 description 1
- CKSCMRNFDBWFND-UHFFFAOYSA-N Oc1c(CCC2=O)c2ccc1 Chemical compound Oc1c(CCC2=O)c2ccc1 CKSCMRNFDBWFND-UHFFFAOYSA-N 0.000 description 1
- HQYMWPRTZRNUCQ-UHFFFAOYSA-N Oc1cc(F)cc(-c(cc2)ccc2F)c1 Chemical compound Oc1cc(F)cc(-c(cc2)ccc2F)c1 HQYMWPRTZRNUCQ-UHFFFAOYSA-N 0.000 description 1
- ORWGYWJZBFJKIC-UHFFFAOYSA-N [O-][N+](c(cc1)c(C2NC2)cc1O)=O Chemical compound [O-][N+](c(cc1)c(C2NC2)cc1O)=O ORWGYWJZBFJKIC-UHFFFAOYSA-N 0.000 description 1
- 239000003781 beta lactamase inhibitor Substances 0.000 description 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14236299P | 1999-07-06 | 1999-07-06 | |
| US60/142,362 | 1999-07-06 | ||
| PCT/US2000/018344 WO2001002411A1 (en) | 1999-07-06 | 2000-07-05 | SULFONAMIDOMETHYL PHOSPHONATE INHIBITORS OF β-LACTAMASE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003503505A JP2003503505A (ja) | 2003-01-28 |
| JP2003503505A5 true JP2003503505A5 (https=) | 2008-08-14 |
| JP4226818B2 JP4226818B2 (ja) | 2009-02-18 |
Family
ID=22499561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001507847A Expired - Fee Related JP4226818B2 (ja) | 1999-07-06 | 2000-07-05 | ベータ−ラクタマーゼのスルフォンアミドメチルホスホン酸阻害剤 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6472406B1 (https=) |
| EP (1) | EP1194436B1 (https=) |
| JP (1) | JP4226818B2 (https=) |
| KR (1) | KR100686988B1 (https=) |
| AT (1) | ATE311397T1 (https=) |
| AU (1) | AU770599B2 (https=) |
| CA (1) | CA2377762C (https=) |
| DE (1) | DE60024455T2 (https=) |
| ES (1) | ES2250150T3 (https=) |
| MX (1) | MXPA02000246A (https=) |
| WO (1) | WO2001002411A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6884791B2 (en) * | 1999-07-06 | 2005-04-26 | Methylgene, Inc. | Inhibitors of β-lactamase |
| US6921756B2 (en) * | 1999-07-06 | 2005-07-26 | Methylgene, Inc. | Inhibitors of β-lactamase |
| ES2258980T3 (es) * | 1999-08-16 | 2006-09-16 | Revaax Pharmaceuticals Llc | Composiciones farmaceuticas que comprenden acido clavulanico o derivados del mismo para el tratamiento de trastornos del comportamiento. |
| US6426342B2 (en) * | 1999-08-16 | 2002-07-30 | Revaax Pharmaceuticals, Llc | Use of β-lactamase inhibitors as neuroprotectants |
| US20100317625A1 (en) * | 2006-05-22 | 2010-12-16 | Dininno Frank | Novel sulfonamidomethylphosphonate inhibitors of beta-lactamase |
| ES2543842T3 (es) * | 2006-05-22 | 2015-08-24 | Methylgene Inc. | Nuevos inhibidores de la beta-lactamasa |
| EP2069347A2 (en) * | 2006-09-27 | 2009-06-17 | Merck & Co., Inc. | Novel inhibitors of beta-lactamase |
| WO2009091856A2 (en) | 2008-01-18 | 2009-07-23 | Merck & Co., Inc. | Beta-lactamase inhibitors |
| US20110046101A1 (en) * | 2008-03-17 | 2011-02-24 | Dmitrienko Gary I | Bate-lactamase inhibitors |
| BRPI1013901A2 (pt) * | 2009-04-29 | 2019-09-24 | Rexahn Pharmaceuticals Inc | formulação de clavulanato para neuroproteção e tratamento de distúrbios neurodegenerativos |
| WO2015112441A1 (en) | 2014-01-22 | 2015-07-30 | Merck Sharp & Dohme Corp. | Metallo-beta-lactamase inhibitors |
| EP3139918B1 (en) | 2014-05-09 | 2019-12-25 | Merck Sharp & Dohme Corp. | Beta-tetrazolyl-propionic acids as metallo-beta-lactamase inhibitors |
| WO2016206101A1 (en) | 2015-06-26 | 2016-12-29 | Merck Sharp & Dohme Corp. | Metallo-beta-lactamase inhibitors |
| BR112018008597B1 (pt) | 2015-10-28 | 2022-03-03 | Fmc Corporation | Composto, composições herbicidas, mistura herbicida e método para o controle do crescimento de vegetação indesejada |
| WO2019018186A1 (en) | 2017-07-17 | 2019-01-24 | Merck Sharp & Dohme Corp. | Metallo-beta-lactamase inhibitors and methods of use thereof |
| CN121005742A (zh) * | 2024-05-23 | 2025-11-25 | 华东师范大学 | 作为cd73抑制剂衍生物及其应用 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2059923C3 (de) | 1970-12-05 | 1979-01-25 | Knoll Ag, 6700 Ludwigshafen | l-a-Isopropyl-o-[(N-methyl-N-homoveratryl)v-aminopropyl] -3,4-dimethoxyphenylacetonitril, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel |
| US3959551A (en) | 1972-03-30 | 1976-05-25 | Hooker Chemicals & Plastics Corporation | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
| US3870771A (en) | 1972-03-30 | 1975-03-11 | Hooker Chemicals Plastics Corp | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
| DE2261081A1 (de) | 1972-12-14 | 1974-06-27 | Bayer Ag | Amidomethanphosphonsaeure-derivate |
| US4031170A (en) | 1973-08-06 | 1977-06-21 | Monsanto Company | Phosphorus compounds |
| US4032601A (en) | 1973-08-06 | 1977-06-28 | Monsanto Company | Process for the production of sulfonamide phosphonates |
| JPS5490160A (en) | 1977-12-26 | 1979-07-17 | Ihara Chem Ind Co Ltd | Alpha,alpha-disubstituted-benzylcyanide derivatives |
| JPS62126160A (ja) | 1985-11-25 | 1987-06-08 | Hokuriku Seiyaku Co Ltd | 新規なフエニルブチラルデヒド誘導体およびその製造法 |
| DE3628300A1 (de) | 1986-08-21 | 1988-02-25 | Schering Ag | Alkan- und alkoxyalkan-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide und akarizide mittel |
| EP0505122A1 (en) | 1991-03-21 | 1992-09-23 | Zeneca Limited | Alpha, alpha-dialkylbenzyl derivatives |
| GB9410721D0 (en) | 1994-05-27 | 1994-07-13 | Chiroscience Ltd | Chiral compounds and their resolution |
| US5681821A (en) | 1994-10-18 | 1997-10-28 | Georgia Tech Research Corp. | Fluorescent 1-peptidylaminoalkanephosphonate derivatives |
| GB9602516D0 (en) | 1996-02-08 | 1996-04-10 | Chiroscience Ltd | Racemisation |
| CA2204082A1 (en) | 1996-05-03 | 1997-11-03 | Michael William John Urquhart | Pharmaceutical compounds |
| WO1998056392A1 (en) * | 1997-06-13 | 1998-12-17 | Northwestern University | INHIBITORS OF β-LACTAMASES AND USES THEREFOR |
| KR100591572B1 (ko) | 1997-12-24 | 2006-06-20 | 메틸진, 인크. | 신규의 β-락타마아제 및 ＤＤ-펩티다아제 저해제 |
| ATE227295T1 (de) | 1998-07-16 | 2002-11-15 | Aventis Pharma Gmbh | Phosphin- und phosphonsäurederivate als arzneimittel |
-
2000
- 2000-07-05 KR KR1020027000135A patent/KR100686988B1/ko not_active Expired - Fee Related
- 2000-07-05 ES ES00943381T patent/ES2250150T3/es not_active Expired - Lifetime
- 2000-07-05 DE DE60024455T patent/DE60024455T2/de not_active Expired - Lifetime
- 2000-07-05 EP EP00943381A patent/EP1194436B1/en not_active Expired - Lifetime
- 2000-07-05 WO PCT/US2000/018344 patent/WO2001002411A1/en not_active Ceased
- 2000-07-05 MX MXPA02000246A patent/MXPA02000246A/es active IP Right Grant
- 2000-07-05 AU AU57858/00A patent/AU770599B2/en not_active Ceased
- 2000-07-05 CA CA002377762A patent/CA2377762C/en not_active Expired - Fee Related
- 2000-07-05 US US09/610,456 patent/US6472406B1/en not_active Expired - Fee Related
- 2000-07-05 JP JP2001507847A patent/JP4226818B2/ja not_active Expired - Fee Related
- 2000-07-05 AT AT00943381T patent/ATE311397T1/de not_active IP Right Cessation
-
2002
- 2002-10-08 US US10/266,213 patent/US7030103B2/en not_active Expired - Fee Related
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