IL42087A - The preparation of 7-aminocephalosporanic acid derivative - Google Patents
The preparation of 7-aminocephalosporanic acid derivativeInfo
- Publication number
- IL42087A IL42087A IL42087A IL4208773A IL42087A IL 42087 A IL42087 A IL 42087A IL 42087 A IL42087 A IL 42087A IL 4208773 A IL4208773 A IL 4208773A IL 42087 A IL42087 A IL 42087A
- Authority
- IL
- Israel
- Prior art keywords
- cephalosporin
- imino
- treated
- ether
- base
- Prior art date
Links
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 20
- -1 aminoadipoyl Chemical group 0.000 claims 20
- 238000000034 method Methods 0.000 claims 19
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 18
- 239000002585 base Substances 0.000 claims 15
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 claims 13
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 claims 12
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- 150000008064 anhydrides Chemical group 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 6
- 239000012346 acetyl chloride Substances 0.000 claims 6
- 229910052783 alkali metal Inorganic materials 0.000 claims 6
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- HZWLVUKHUSRPCG-OOARYINLSA-M sodium;(6r,7r)-3-(acetyloxymethyl)-7-[[(5r)-5-azaniumyl-5-carboxylatopentanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HZWLVUKHUSRPCG-OOARYINLSA-M 0.000 claims 5
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 150000004820 halides Chemical class 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 229930186147 Cephalosporin Natural products 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 229910052799 carbon Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229940124587 cephalosporin Drugs 0.000 claims 2
- 150000001780 cephalosporins Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 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
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 1
- 229940049954 penicillin Drugs 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 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
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
-
- 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US249293A US3904615A (en) | 1972-05-01 | 1972-05-01 | Process for cleaving cephalosporin compounds |
| US00249294A US3840532A (en) | 1972-05-01 | 1972-05-01 | Process for cleaving cephalosporin compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42087A0 IL42087A0 (en) | 1973-06-29 |
| IL42087A true IL42087A (en) | 1976-01-30 |
Family
ID=26939961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42087A IL42087A (en) | 1972-05-01 | 1973-04-20 | The preparation of 7-aminocephalosporanic acid derivative |
Country Status (16)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5256823U (enrdf_load_stackoverflow) * | 1975-10-22 | 1977-04-25 | ||
| DE2933075C2 (de) * | 1979-08-16 | 1984-04-19 | Zahnraederfabrik Renk Ag, 8900 Augsburg | Antriebs- und Bremsanlage von Kraftfahrzeugen |
| JPH0633990U (ja) * | 1992-09-29 | 1994-05-06 | 呉羽合繊株式会社 | 着色装置 |
| JP3487083B2 (ja) | 1996-02-09 | 2004-01-13 | 日立化成工業株式会社 | 熱硬化性樹脂組成物及びその硬化物 |
| US6518420B2 (en) | 1997-06-04 | 2003-02-11 | Biochemie Gesellschaft M.B.H. | Precipitation process of 7-aminocephalosporanic acid (7-ACA) |
| SK165399A3 (en) * | 1997-06-04 | 2000-05-16 | Biochemie Gmbh | Process for the preparation of rosettes or agglomerates of 7-aminocephalosporanic acid (7-aca) |
| CN110094151B (zh) * | 2018-01-31 | 2020-06-16 | 光宝电子(广州)有限公司 | 百叶窗 |
-
1973
- 1973-03-27 ES ES414153A patent/ES414153A1/es not_active Expired
- 1973-04-17 GB GB1839173A patent/GB1421199A/en not_active Expired
- 1973-04-20 IL IL42087A patent/IL42087A/en unknown
- 1973-04-20 YU YU01082/73A patent/YU108273A/xx unknown
- 1973-04-25 IE IE646/73A patent/IE37562B1/xx unknown
- 1973-04-26 DE DE2321234A patent/DE2321234A1/de not_active Ceased
- 1973-04-26 HU HUEI472A patent/HU167595B/hu unknown
- 1973-04-26 SE SE7305862A patent/SE418746B/xx unknown
- 1973-04-26 HU HUEI541A patent/HU167444B/hu unknown
- 1973-04-27 FR FR7315533A patent/FR2183098B1/fr not_active Expired
- 1973-04-28 SU SU731914796A patent/SU587867A3/ru active
- 1973-04-30 CH CH612873A patent/CH582184A5/xx not_active IP Right Cessation
- 1973-05-01 JP JP48047638A patent/JPS5842194B2/ja not_active Expired
- 1973-05-01 NL NLAANVRAGE7306068,A patent/NL181197C/xx active Search and Examination
- 1973-05-02 DD DD170570A patent/DD105239A5/xx unknown
- 1973-05-02 RO RO7300074662A patent/RO62896A/ro unknown
- 1973-10-26 AR AR250738A patent/AR203623A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4947387A (enrdf_load_stackoverflow) | 1974-05-08 |
| IE37562B1 (en) | 1977-08-17 |
| FR2183098B1 (enrdf_load_stackoverflow) | 1975-08-22 |
| FR2183098A1 (enrdf_load_stackoverflow) | 1973-12-14 |
| RO62896A (fr) | 1978-03-15 |
| HU167595B (enrdf_load_stackoverflow) | 1975-11-28 |
| AR203623A1 (es) | 1975-09-30 |
| GB1421199A (en) | 1976-01-14 |
| IL42087A0 (en) | 1973-06-29 |
| NL181197C (nl) | 1987-07-01 |
| DE2321234A1 (de) | 1973-11-22 |
| HU167444B (enrdf_load_stackoverflow) | 1975-10-28 |
| DD105239A5 (enrdf_load_stackoverflow) | 1974-04-12 |
| SE418746B (sv) | 1981-06-22 |
| SU587867A3 (ru) | 1978-01-05 |
| IE37562L (en) | 1973-11-01 |
| NL7306068A (enrdf_load_stackoverflow) | 1973-11-05 |
| JPS5842194B2 (ja) | 1983-09-17 |
| AU5468973A (en) | 1974-10-24 |
| ES414153A1 (es) | 1976-06-01 |
| CH582184A5 (enrdf_load_stackoverflow) | 1976-11-30 |
| YU108273A (en) | 1982-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3705897A (en) | Method for converting delta**2 cephalosporin to delta**3 cephalosporin | |
| IL42087A (en) | The preparation of 7-aminocephalosporanic acid derivative | |
| KR840002407A (ko) | 세팔로스포린 유도체의 제조방법 | |
| US3674784A (en) | 3-formyl cephalosporin sulfoxides | |
| DE2216146B2 (de) | Verfahren zur Herstellung von 3-Exomethylen-cephalosporinderivaten | |
| US3843637A (en) | Process for rearranging 6-acylamidopenicillanic acid-1-oxides to 7-acyla mido-3-methyl-ceph-3-em-4-carboxylic acids | |
| US3549628A (en) | Side chain cleavage in desacetoxycephalosporin esters | |
| US3962232A (en) | 7-methoxycephalosporins | |
| US3780028A (en) | Diphenylmethyl 7beta-(d-2,2-dimethyl-3-nitroso-5-oxo-4-phenyl-1-imidazolidinyl)-3-methyl-cephem-4-carboxylate | |
| JP3073437B2 (ja) | ３−ホルミル−セフェム誘導体の製造方法 | |
| US3716533A (en) | N-deformylation of 3-halomethyl-7beta-formamidocephalosporin-1-oxidesn-deformylation of 3-halomethyl-7 beta-formamidocephalosporin-1-oxide | |
| KR100458232B1 (ko) | 세펨화합물의 제조방법 | |
| ES2320940T3 (es) | Procedimiento mejorado para la precipitacion de acido 7-aminocefalosporanico (7-aca). | |
| CA1045115A (en) | Process for preparing 6-aminopenicillanic acid, 7-aminocephalosporanic acid and derivatives | |
| US3882108A (en) | Preparation of 7-amino cephalosporin compound | |
| GB1354017A (en) | Process for producing 7-amino-cephalosporanic acids | |
| JPS60202891A (ja) | デスアセチル‐７‐アミノセフアロスポラニツクアシツドから３‐エステルメチルセフアロスポリン類を製造する解媒方法 | |
| US3922268A (en) | 3-Halomethyl-{66 {hu 3-Cephalosporin esters | |
| US3879398A (en) | Salts of a monophosphonic acid and a monoamine | |
| GB1391271A (en) | Preparation of antibiotic compounds | |
| US3892736A (en) | Process for selective blocking of the carboxyl group on the 7-position of (6R, 7R)-3-acetoxymethyl-7-(4-carboxybutanamido)ceph-3-em-4-carboxylic acid | |
| JPH0649705B2 (ja) | ３位ハロゲン化セファロスポリン化合物のアミノ化 | |
| US3904615A (en) | Process for cleaving cephalosporin compounds | |
| GB1359374A (en) | Cycloaliphatic penicilins | |
| KR100387581B1 (ko) | 인듐과 아연 금속을 이용한 신규 페남 유도체 및 이의 제조 방법 |