FI108133B - Menetelmä loracarbef-monohydraatin valmistamiseksi ja kiteinen loracarbef-isopropanolaatti - Google Patents
Menetelmä loracarbef-monohydraatin valmistamiseksi ja kiteinen loracarbef-isopropanolaatti Download PDFInfo
- Publication number
- FI108133B FI108133B FI942631A FI942631A FI108133B FI 108133 B FI108133 B FI 108133B FI 942631 A FI942631 A FI 942631A FI 942631 A FI942631 A FI 942631A FI 108133 B FI108133 B FI 108133B
- Authority
- FI
- Finland
- Prior art keywords
- loracarbef
- isopropanolate
- crystalline
- monohydrate
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 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 title abstract description 15
- 229960001977 loracarbef Drugs 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 5
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 title description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 37
- 150000004682 monohydrates Chemical group 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 abstract description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000000023 Kugelrohr distillation Methods 0.000 description 2
- 150000004683 dihydrates Chemical group 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- KYUTYGAHECGMSX-RXMQYKEDSA-N (6r)-4,5-dithia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1SC=CN2C(=O)C[C@H]21 KYUTYGAHECGMSX-RXMQYKEDSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 238000004846 x-ray emission Methods 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
- C07D463/16—Nitrogen atoms
- C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
- C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D463/22—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen further substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/072,204 US5399686A (en) | 1993-06-04 | 1993-06-04 | Loracarbef isopropanolate and a process for converting loracarbef isopropanolate to loracarbef monohydrate |
| US7220493 | 1993-06-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI942631A0 FI942631A0 (fi) | 1994-06-03 |
| FI942631A FI942631A (fi) | 1994-12-05 |
| FI108133B true FI108133B (fi) | 2001-11-30 |
Family
ID=22106211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI942631A FI108133B (fi) | 1993-06-04 | 1994-06-03 | Menetelmä loracarbef-monohydraatin valmistamiseksi ja kiteinen loracarbef-isopropanolaatti |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US5399686A (pt) |
| EP (1) | EP0627429B1 (pt) |
| JP (1) | JP3442861B2 (pt) |
| KR (1) | KR100308746B1 (pt) |
| AT (1) | ATE178328T1 (pt) |
| BR (1) | BR9402148A (pt) |
| CA (1) | CA2124999C (pt) |
| DE (1) | DE69417472T2 (pt) |
| DK (1) | DK0627429T3 (pt) |
| ES (1) | ES2129106T3 (pt) |
| FI (1) | FI108133B (pt) |
| GR (1) | GR3030211T3 (pt) |
| HU (1) | HUT67911A (pt) |
| IL (1) | IL109869A (pt) |
| SI (1) | SI0627429T1 (pt) |
| TW (1) | TW492968B (pt) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5399686A (en) * | 1993-06-04 | 1995-03-21 | Eli Lilly And Company | Loracarbef isopropanolate and a process for converting loracarbef isopropanolate to loracarbef monohydrate |
| US5550231A (en) * | 1993-06-15 | 1996-08-27 | Eli Lilly And Company | Loracarbef hydrochloride C1-C3 alcohol solvates and uses thereof |
| US5580977A (en) * | 1995-03-01 | 1996-12-03 | Eli Lilly And Company | Process for preparing loracarbef monohydrate |
| GB9717629D0 (en) | 1997-08-21 | 1997-10-22 | Johnson Matthey Plc | Removal of residual organic solvents |
| KR100519650B1 (ko) * | 1999-02-05 | 2005-10-07 | 제일모직주식회사 | 점도가 균일한 폴리아믹산의 제조방법 |
| AU2003283624A1 (en) * | 2002-11-21 | 2004-06-15 | Ranbaxy Laboratories Limited | Monohydrate solvates of loracarbef |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502663A (en) * | 1969-04-21 | 1970-03-24 | Lilly Co Eli | Crystalline cephalosporin,method for its manufacture |
| US3531481A (en) * | 1969-04-21 | 1970-09-29 | Lilly Co Eli | Method for manufacture of crystalline cephalosporin |
| US4775751A (en) * | 1985-06-03 | 1988-10-04 | Eli Lilly & Company | Process for cephalexin hydrochloride alcoholates |
| ZA887409B (en) * | 1987-10-06 | 1990-06-27 | Lilly Co Eli | Crystalline beta-lactam hydrate |
| US4977257A (en) * | 1988-11-14 | 1990-12-11 | Eli Lilly And Company | DMF solvates of a β-lactam antibiotic |
| CA2002596A1 (en) * | 1988-11-14 | 1990-05-14 | Thomas M. Eckrich | Hydrates of b-lactam antibiotic |
| US5352782A (en) * | 1993-06-04 | 1994-10-04 | Eli Lilly And Company | Process for preparing crystalline β-lactam monohydrate |
| US5399686A (en) * | 1993-06-04 | 1995-03-21 | Eli Lilly And Company | Loracarbef isopropanolate and a process for converting loracarbef isopropanolate to loracarbef monohydrate |
-
1993
- 1993-06-04 US US08/072,204 patent/US5399686A/en not_active Expired - Lifetime
-
1994
- 1994-06-01 TW TW083105010A patent/TW492968B/zh not_active IP Right Cessation
- 1994-06-01 BR BR9402148A patent/BR9402148A/pt not_active Application Discontinuation
- 1994-06-01 DE DE69417472T patent/DE69417472T2/de not_active Expired - Fee Related
- 1994-06-01 DK DK94303942T patent/DK0627429T3/da active
- 1994-06-01 SI SI9430256T patent/SI0627429T1/xx not_active IP Right Cessation
- 1994-06-01 ES ES94303942T patent/ES2129106T3/es not_active Expired - Lifetime
- 1994-06-01 AT AT94303942T patent/ATE178328T1/de not_active IP Right Cessation
- 1994-06-01 EP EP94303942A patent/EP0627429B1/en not_active Expired - Lifetime
- 1994-06-02 KR KR1019940012342A patent/KR100308746B1/ko not_active IP Right Cessation
- 1994-06-02 CA CA002124999A patent/CA2124999C/en not_active Expired - Fee Related
- 1994-06-02 IL IL109869A patent/IL109869A/en not_active IP Right Cessation
- 1994-06-03 HU HU9401673A patent/HUT67911A/hu unknown
- 1994-06-03 FI FI942631A patent/FI108133B/fi not_active IP Right Cessation
- 1994-06-03 JP JP12229794A patent/JP3442861B2/ja not_active Expired - Fee Related
- 1994-12-01 US US08/347,759 patent/US5672700A/en not_active Expired - Fee Related
-
1999
- 1999-05-13 GR GR990401296T patent/GR3030211T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR3030211T3 (en) | 1999-08-31 |
| EP0627429B1 (en) | 1999-03-31 |
| DE69417472D1 (de) | 1999-05-06 |
| KR100308746B1 (ko) | 2001-11-30 |
| ATE178328T1 (de) | 1999-04-15 |
| DE69417472T2 (de) | 1999-08-19 |
| HU9401673D0 (en) | 1994-09-28 |
| SI0627429T1 (en) | 1999-10-31 |
| US5399686A (en) | 1995-03-21 |
| BR9402148A (pt) | 1994-12-27 |
| FI942631A (fi) | 1994-12-05 |
| KR950000703A (ko) | 1995-01-03 |
| EP0627429A1 (en) | 1994-12-07 |
| FI942631A0 (fi) | 1994-06-03 |
| DK0627429T3 (da) | 1999-10-11 |
| TW492968B (en) | 2002-07-01 |
| CA2124999A1 (en) | 1994-12-05 |
| JP3442861B2 (ja) | 2003-09-02 |
| ES2129106T3 (es) | 1999-06-01 |
| US5672700A (en) | 1997-09-30 |
| CA2124999C (en) | 2004-08-10 |
| JPH06345762A (ja) | 1994-12-20 |
| IL109869A0 (en) | 1994-10-07 |
| HUT67911A (en) | 1995-05-29 |
| IL109869A (en) | 1998-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |