KR930017907A - β-락탐 화합물에 이용하기 위한 에스테르 절단방법 - Google Patents
β-락탐 화합물에 이용하기 위한 에스테르 절단방법 Download PDFInfo
- Publication number
- KR930017907A KR930017907A KR1019930002043A KR930002043A KR930017907A KR 930017907 A KR930017907 A KR 930017907A KR 1019930002043 A KR1019930002043 A KR 1019930002043A KR 930002043 A KR930002043 A KR 930002043A KR 930017907 A KR930017907 A KR 930017907A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- substituted
- group
- phenyl
- formula
- 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.)
- Ceased
Links
- -1 β-lactam compounds Chemical class 0.000 title claims abstract 19
- 238000000034 method Methods 0.000 title claims abstract 7
- 238000007257 deesterification reaction Methods 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 3
- 239000000376 reactant Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000004149 thio group Chemical group *S* 0.000 claims 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical group [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 229910001416 lithium ion Inorganic materials 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 claims 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229940049954 penicillin Drugs 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000003952 β-lactams Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- C07D463/02—Preparation
- C07D463/06—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/836,640 US5302711A (en) | 1992-02-18 | 1992-02-18 | Ester cleavage process for use with β-lactams |
| US836,640 | 1992-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR930017907A true KR930017907A (ko) | 1993-09-20 |
Family
ID=25272395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930002043A Ceased KR930017907A (ko) | 1992-02-18 | 1993-02-12 | β-락탐 화합물에 이용하기 위한 에스테르 절단방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5302711A (enExample) |
| EP (1) | EP0557035A3 (enExample) |
| JP (1) | JPH05286971A (enExample) |
| KR (1) | KR930017907A (enExample) |
| BR (1) | BR9300542A (enExample) |
| CA (1) | CA2089540A1 (enExample) |
| HU (1) | HUT64351A (enExample) |
| IL (1) | IL104699A0 (enExample) |
| MX (1) | MX9300761A (enExample) |
| TW (1) | TW232694B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2379650C (en) | 1999-07-30 | 2008-09-02 | Eisai Co., Ltd. | Process for producing a basic antibiotic inorganic acid salt, and oxalate intermediate |
| CN103588790A (zh) * | 2013-11-29 | 2014-02-19 | 中国科学院长春应用化学研究所 | 7-氨基-3-氯-3-头孢-4-羧酸-对硝基苄基酯的制备方法 |
| CN106866704B (zh) * | 2017-02-08 | 2019-06-14 | 河北科技大学 | 催化氢化脱除对硝基苄酯以制备7-acca的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1546757A (en) * | 1975-04-10 | 1979-05-31 | Lilly Industries Ltd | Crystalline cephalosporin salts |
| JPS52106891A (en) * | 1976-03-03 | 1977-09-07 | Shionogi & Co Ltd | Removal of carboxyl protecting group |
| DE2725519A1 (de) * | 1977-06-06 | 1978-12-21 | Shionogi & Co | Verfahren zur herstellung freier carbonsaeuren durch esterspaltung |
| IL72412A (en) * | 1983-07-22 | 1988-05-31 | Lilly Co Eli | Deesterification of beta-lactam antibiotic esters |
| ATE138664T1 (de) * | 1985-08-12 | 1996-06-15 | Upjohn Co | Umwandlung des cephalosporin-hydrohalid-salzes zu einem alkalimetallsalz |
| EP0263901A1 (en) * | 1986-10-08 | 1988-04-20 | The Upjohn Company | Conversion of cephalosporin hydrohalide salt to alkali metal salt |
| DK0395219T3 (da) * | 1989-03-30 | 1999-02-15 | Pfizer | Cephalosporiner og deres homologer, fremgangsmåde til deres fremstilling og farmaceutiske præparater |
| US5043439A (en) * | 1990-03-08 | 1991-08-27 | Bristol-Myers Squibb Company | Process for production of cephalosporins |
| US5095107A (en) * | 1990-11-05 | 1992-03-10 | Eli Lilly And Company | Process for cleavage of esters during the production of cephalosporins |
-
1992
- 1992-02-18 US US07/836,640 patent/US5302711A/en not_active Expired - Lifetime
-
1993
- 1993-02-11 IL IL104699A patent/IL104699A0/xx unknown
- 1993-02-11 BR BR9300542A patent/BR9300542A/pt not_active Application Discontinuation
- 1993-02-12 KR KR1019930002043A patent/KR930017907A/ko not_active Ceased
- 1993-02-12 JP JP5024157A patent/JPH05286971A/ja not_active Withdrawn
- 1993-02-12 MX MX9300761A patent/MX9300761A/es not_active IP Right Cessation
- 1993-02-12 TW TW082100977A patent/TW232694B/zh active
- 1993-02-12 HU HU9300384A patent/HUT64351A/hu unknown
- 1993-02-15 CA CA002089540A patent/CA2089540A1/en not_active Abandoned
- 1993-02-15 EP EP19930301069 patent/EP0557035A3/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0557035A3 (en) | 1993-12-01 |
| EP0557035A2 (en) | 1993-08-25 |
| HU9300384D0 (en) | 1993-04-28 |
| TW232694B (enExample) | 1994-10-21 |
| US5302711A (en) | 1994-04-12 |
| BR9300542A (pt) | 1993-08-24 |
| JPH05286971A (ja) | 1993-11-02 |
| IL104699A0 (en) | 1993-06-10 |
| CA2089540A1 (en) | 1993-08-19 |
| HUT64351A (en) | 1993-12-28 |
| MX9300761A (es) | 1993-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19930212 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19980211 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19930212 Comment text: Patent Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19991129 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20000223 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19991129 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |