CA2466964A1 - Produits de solvatation d'alcools en c1-c3 et de chlorhydrate de loracarbef, leur utilite - Google Patents
Produits de solvatation d'alcools en c1-c3 et de chlorhydrate de loracarbef, leur utilite Download PDFInfo
- Publication number
- CA2466964A1 CA2466964A1 CA002466964A CA2466964A CA2466964A1 CA 2466964 A1 CA2466964 A1 CA 2466964A1 CA 002466964 A CA002466964 A CA 002466964A CA 2466964 A CA2466964 A CA 2466964A CA 2466964 A1 CA2466964 A1 CA 2466964A1
- Authority
- CA
- Canada
- Prior art keywords
- loracarbef
- hydrochloride
- alcohol
- yield
- ethanol
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 239000012453 solvate Substances 0.000 title claims abstract description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229960001977 loracarbef Drugs 0.000 title claims description 45
- JAPHQRWPEGVNBT-UTUOFQBUSA-M loracarbef anion Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CC[C@@H]32)C([O-])=O)=O)N)=CC=CC=C1 JAPHQRWPEGVNBT-UTUOFQBUSA-M 0.000 title claims 3
- 238000000034 method Methods 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 11
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 3
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract description 5
- GPYKKBAAPVOCIW-HSASPSRMSA-N (6r,7s)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate Chemical compound O.C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CC[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 GPYKKBAAPVOCIW-HSASPSRMSA-N 0.000 description 49
- 235000019441 ethanol Nutrition 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002002 slurry Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000004682 monohydrates Chemical group 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 238000005917 acylation reaction Methods 0.000 description 7
- 230000010933 acylation Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- RMIGTEGRHJUHHM-UHFFFAOYSA-N propan-1-ol;hydrochloride Chemical compound Cl.CCCO RMIGTEGRHJUHHM-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 0 OC(C(N([C@@](CC1)[C@@]2NC3=*[C@]3c3ccccc3)C2=O)=C1Cl)=O Chemical compound OC(C(N([C@@](CC1)[C@@]2NC3=*[C@]3c3ccccc3)C2=O)=C1Cl)=O 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009838 combustion analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/077,305 | 1993-06-15 | ||
| US08/077,305 US5550231A (en) | 1993-06-15 | 1993-06-15 | Loracarbef hydrochloride C1-C3 alcohol solvates and uses thereof |
| CA002125762A CA2125762A1 (fr) | 1993-06-15 | 1994-06-13 | Produits de solvatation d'alcools en c1-c3 et de chlorhydrate de loracarbef, leur utilite |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002125762A Division CA2125762A1 (fr) | 1993-06-15 | 1994-06-13 | Produits de solvatation d'alcools en c1-c3 et de chlorhydrate de loracarbef, leur utilite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2466964A1 true CA2466964A1 (fr) | 1994-12-16 |
Family
ID=32683207
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002466974A Abandoned CA2466974A1 (fr) | 1993-06-15 | 1994-06-13 | Solvats alcooliques (c1-c3) de chlorhydrate de loracarbef et leurs utilisations |
| CA002466964A Abandoned CA2466964A1 (fr) | 1993-06-15 | 1994-06-13 | Produits de solvatation d'alcools en c1-c3 et de chlorhydrate de loracarbef, leur utilite |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002466974A Abandoned CA2466974A1 (fr) | 1993-06-15 | 1994-06-13 | Solvats alcooliques (c1-c3) de chlorhydrate de loracarbef et leurs utilisations |
Country Status (1)
| Country | Link |
|---|---|
| CA (2) | CA2466974A1 (fr) |
-
1994
- 1994-06-13 CA CA002466974A patent/CA2466974A1/fr not_active Abandoned
- 1994-06-13 CA CA002466964A patent/CA2466964A1/fr not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2466974A1 (fr) | 1994-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |