JP2006503053A5 - - Google Patents
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- Publication number
- JP2006503053A5 JP2006503053A5 JP2004537129A JP2004537129A JP2006503053A5 JP 2006503053 A5 JP2006503053 A5 JP 2006503053A5 JP 2004537129 A JP2004537129 A JP 2004537129A JP 2004537129 A JP2004537129 A JP 2004537129A JP 2006503053 A5 JP2006503053 A5 JP 2006503053A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydrogen
- compound
- alkyl
- butyl
- 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.)
- Pending
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 37
- 239000001257 hydrogen Substances 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 32
- 238000000034 method Methods 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 239000002904 solvent Substances 0.000 claims 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 10
- 230000015572 biosynthetic process Effects 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 239000012190 activator Substances 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- -1 n- butyl Chemical group 0.000 claims 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 235000019439 ethyl acetate Nutrition 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 2
- 229940011051 isopropyl acetate Drugs 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical group CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims 1
- CAFROQYMUICGNO-UHFFFAOYSA-N 2,2,2-trifluoroethyl formate Chemical compound FC(F)(F)COC=O CAFROQYMUICGNO-UHFFFAOYSA-N 0.000 claims 1
- GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 claims 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
- 229910052808 lithium carbonate Inorganic materials 0.000 claims 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 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
- 125000005425 toluyl group Chemical group 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 Cc1c(*)c(*)c(*)c(*)n1 Chemical compound Cc1c(*)c(*)c(*)c(*)n1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41192002P | 2002-09-19 | 2002-09-19 | |
| US48024203P | 2003-06-20 | 2003-06-20 | |
| PCT/EP2003/010416 WO2004026824A1 (en) | 2002-09-19 | 2003-09-18 | Process for preparing intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006503053A JP2006503053A (ja) | 2006-01-26 |
| JP2006503053A5 true JP2006503053A5 (enExample) | 2006-11-09 |
Family
ID=32033579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004537129A Pending JP2006503053A (ja) | 2002-09-19 | 2003-09-18 | 中間体の製造法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7589216B2 (enExample) |
| EP (1) | EP1542968B1 (enExample) |
| JP (1) | JP2006503053A (enExample) |
| KR (1) | KR20050057429A (enExample) |
| CN (1) | CN100439334C (enExample) |
| AT (1) | ATE417826T1 (enExample) |
| AU (1) | AU2003273404B2 (enExample) |
| BR (1) | BR0314592A (enExample) |
| CA (1) | CA2499426A1 (enExample) |
| DE (1) | DE60325390D1 (enExample) |
| DK (1) | DK1542968T3 (enExample) |
| EC (1) | ECSP055692A (enExample) |
| ES (1) | ES2321504T3 (enExample) |
| MX (1) | MXPA05003089A (enExample) |
| NO (1) | NO20051867D0 (enExample) |
| NZ (1) | NZ538833A (enExample) |
| PL (1) | PL374961A1 (enExample) |
| PT (1) | PT1542968E (enExample) |
| RU (1) | RU2374227C2 (enExample) |
| WO (1) | WO2004026824A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1406893E (pt) | 2001-06-15 | 2007-07-12 | Vicuron Pharm Inc | Compostos bicíclicos de pirrolidina |
| WO2004026824A1 (en) | 2002-09-19 | 2004-04-01 | Novartis Ag | Process for preparing intermediates |
| EP1599440A2 (en) | 2003-02-21 | 2005-11-30 | Novartis AG | Chemical process for the preparation of intermediates to obtain n-formyl hydroxylamine compounds |
| GT200600196A (es) * | 2005-05-23 | 2007-01-15 | Compuestos n-formil de hidroxilamina | |
| CN101434570B (zh) * | 2007-11-16 | 2011-02-02 | 上海医药工业研究院 | 吡咯烷衍生物及其制备方法和应用 |
| US11174288B2 (en) | 2016-12-06 | 2021-11-16 | Northeastern University | Heparin-binding cationic peptide self-assembling peptide amphiphiles useful against drug-resistant bacteria |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU384814A1 (ru) * | 1970-12-25 | 1973-05-29 | Всесоюзный научно исследовательский институт тетических , натуральных душистых веществ | СПОСОБ ПОЛУЧЕНИЯ р-МЕТИЛЗАМЕЩЕННЫХ со-ОКСИКАРБОНОВЫХ КИСЛОТ |
| US4123465A (en) * | 1975-10-16 | 1978-10-31 | Hoffmann-La Roche Inc. | Chiral tertiary phosphines |
| JPS5377010A (en) * | 1976-12-16 | 1978-07-08 | Mitsui Toatsu Chem Inc | Preparation of hydroxypivalic acid |
| JPS6030666B2 (ja) * | 1980-08-20 | 1985-07-17 | 鐘淵化学工業株式会社 | 光学活性メルカプトカルボン酸の製造法 |
| JPS5953839B2 (ja) * | 1980-10-06 | 1984-12-27 | 鐘淵化学工業株式会社 | （−）−α−ヒドロキシメチル酪酸の製造方法 |
| JPH01149751A (ja) * | 1987-12-08 | 1989-06-12 | Agency Of Ind Science & Technol | ２−ｎ−ヘキシル−３−ヒドロキシ−ｎ−デカン酸及びそのエステル |
| AU633260B2 (en) * | 1988-08-09 | 1993-01-28 | Genencor International, Inc. | Chiral hydroxycarboxylic acids from prochiral diols |
| JPH0592948A (ja) * | 1991-02-06 | 1993-04-16 | Yoshitomi Pharmaceut Ind Ltd | プロピオン酸アミド誘導体およびその医薬用途 |
| IL137312A (en) | 1998-02-07 | 2005-12-18 | Vernalis Oxford Ltd | Pharmaceutical anti-bacterial compositions comprising n-formyl hydroxylamine derivatives and severalsuch derivatives |
| US6977141B2 (en) | 1998-02-10 | 2005-12-20 | Vicuron Pharmaceuticals Inc. | Direct adsorption scintillation assay for measuring enzyme activity and assaying biochemical processes |
| UY27192A1 (es) * | 2001-03-01 | 2002-09-30 | Smithkline Beecham Corp | Inhibidores de peptido-deformilasa |
| PT1406893E (pt) | 2001-06-15 | 2007-07-12 | Vicuron Pharm Inc | Compostos bicíclicos de pirrolidina |
| AR036053A1 (es) | 2001-06-15 | 2004-08-04 | Versicor Inc | Compuestos de n-formil-hidroxilamina, un proceso para su preparacion y composiciones farmaceuticas |
| JP2006052138A (ja) * | 2002-08-23 | 2006-02-23 | Dainippon Sumitomo Pharma Co Ltd | プロリン誘導体 |
| WO2004026824A1 (en) | 2002-09-19 | 2004-04-01 | Novartis Ag | Process for preparing intermediates |
| EP1599440A2 (en) | 2003-02-21 | 2005-11-30 | Novartis AG | Chemical process for the preparation of intermediates to obtain n-formyl hydroxylamine compounds |
| TW200427458A (en) | 2003-04-02 | 2004-12-16 | Novartis Ag | Crystalline N-formyl hydroxylamine compounds |
| AU2004251876A1 (en) | 2003-06-26 | 2005-01-06 | Novartis Ag | Process for preparing intermediates useful to prepare certain antibacterial N-formyl hydroxylamines |
-
2003
- 2003-09-18 WO PCT/EP2003/010416 patent/WO2004026824A1/en not_active Ceased
- 2003-09-18 KR KR1020057004645A patent/KR20050057429A/ko not_active Ceased
- 2003-09-18 US US10/527,628 patent/US7589216B2/en not_active Expired - Fee Related
- 2003-09-18 DE DE60325390T patent/DE60325390D1/de not_active Expired - Lifetime
- 2003-09-18 CN CNB038224712A patent/CN100439334C/zh not_active Expired - Fee Related
- 2003-09-18 RU RU2005111600/04A patent/RU2374227C2/ru not_active IP Right Cessation
- 2003-09-18 MX MXPA05003089A patent/MXPA05003089A/es active IP Right Grant
- 2003-09-18 AT AT03755559T patent/ATE417826T1/de not_active IP Right Cessation
- 2003-09-18 JP JP2004537129A patent/JP2006503053A/ja active Pending
- 2003-09-18 NZ NZ538833A patent/NZ538833A/en not_active IP Right Cessation
- 2003-09-18 AU AU2003273404A patent/AU2003273404B2/en not_active Ceased
- 2003-09-18 EP EP03755559A patent/EP1542968B1/en not_active Expired - Lifetime
- 2003-09-18 ES ES03755559T patent/ES2321504T3/es not_active Expired - Lifetime
- 2003-09-18 DK DK03755559T patent/DK1542968T3/da active
- 2003-09-18 CA CA002499426A patent/CA2499426A1/en not_active Abandoned
- 2003-09-18 BR BR0314592-1A patent/BR0314592A/pt not_active IP Right Cessation
- 2003-09-18 PL PL03374961A patent/PL374961A1/xx not_active Application Discontinuation
- 2003-09-18 PT PT03755559T patent/PT1542968E/pt unknown
-
2005
- 2005-03-18 EC EC2005005692A patent/ECSP055692A/es unknown
- 2005-04-18 NO NO20051867A patent/NO20051867D0/no not_active Application Discontinuation
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