CA2401578A1 - Formes cristallines d'intermediaires a chaines laterales pour des antibiotiques - Google Patents
Formes cristallines d'intermediaires a chaines laterales pour des antibiotiques Download PDFInfo
- Publication number
- CA2401578A1 CA2401578A1 CA002401578A CA2401578A CA2401578A1 CA 2401578 A1 CA2401578 A1 CA 2401578A1 CA 002401578 A CA002401578 A CA 002401578A CA 2401578 A CA2401578 A CA 2401578A CA 2401578 A1 CA2401578 A1 CA 2401578A1
- Authority
- CA
- Canada
- Prior art keywords
- crystalline forms
- side chain
- compound
- crystalline
- dipp
- 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.)
- Abandoned
Links
- 239000000543 intermediate Substances 0.000 title description 3
- 230000003115 biocidal effect Effects 0.000 title description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 abstract description 5
- 239000012453 solvate Substances 0.000 abstract description 3
- PSXUKPCAIKETHF-UHFFFAOYSA-N 2-[4-[3-[4-(4,5-dihydro-1h-imidazol-2-yl)phenoxy]propoxy]phenyl]-4,5-dihydro-1h-imidazole Chemical compound C=1C=C(C=2NCCN=2)C=CC=1OCCCOC(C=C1)=CC=C1C1=NCCN1 PSXUKPCAIKETHF-UHFFFAOYSA-N 0.000 abstract 1
- 102100029579 Diphosphoinositol polyphosphate phosphohydrolase 1 Human genes 0.000 abstract 1
- 101710153356 mRNA-decapping protein g5R Proteins 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- -1 (1S)-3-oxo-2-thia-5-azabicyclo[2.2.1]hept-5-yl Chemical group 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QPQGTZMAQRXCJW-UHFFFAOYSA-N [chloro(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(Cl)C1=CC=CC=C1 QPQGTZMAQRXCJW-UHFFFAOYSA-N 0.000 description 2
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- TWKKUWBBCHHMLT-UHFFFAOYSA-N disodium;sulfide;trihydrate Chemical compound O.O.O.[Na+].[Na+].[S-2] TWKKUWBBCHHMLT-UHFFFAOYSA-N 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
On décrit de la thiolactone DIPP cristalline et des solvates de cette dernière ainsi qu'un type cristallin de ces composés.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18603900P | 2000-03-01 | 2000-03-01 | |
| US60/186,039 | 2000-03-01 | ||
| PCT/US2001/006179 WO2001064684A1 (fr) | 2000-03-01 | 2001-02-27 | Formes cristallines d'intermediaires a chaines laterales pour des antibiotiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2401578A1 true CA2401578A1 (fr) | 2001-09-07 |
Family
ID=22683405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002401578A Abandoned CA2401578A1 (fr) | 2000-03-01 | 2001-02-27 | Formes cristallines d'intermediaires a chaines laterales pour des antibiotiques |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1261612A4 (fr) |
| JP (1) | JP2003525297A (fr) |
| AU (1) | AU4723501A (fr) |
| CA (1) | CA2401578A1 (fr) |
| WO (1) | WO2001064684A1 (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002504156A (ja) * | 1997-07-09 | 2002-02-05 | メルク エンド カンパニー インコーポレーテッド | カルバペネム側鎖中間体の合成プロセス |
-
2001
- 2001-02-27 WO PCT/US2001/006179 patent/WO2001064684A1/fr not_active Application Discontinuation
- 2001-02-27 EP EP01920152A patent/EP1261612A4/fr not_active Withdrawn
- 2001-02-27 CA CA002401578A patent/CA2401578A1/fr not_active Abandoned
- 2001-02-27 JP JP2001564180A patent/JP2003525297A/ja not_active Withdrawn
- 2001-02-27 AU AU47235/01A patent/AU4723501A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU4723501A (en) | 2001-09-12 |
| EP1261612A1 (fr) | 2002-12-04 |
| EP1261612A4 (fr) | 2003-04-02 |
| JP2003525297A (ja) | 2003-08-26 |
| WO2001064684A1 (fr) | 2001-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |