IL33889A - Preparation of 7-amino cephalosporin esters - Google Patents
Preparation of 7-amino cephalosporin estersInfo
- Publication number
- IL33889A IL33889A IL33889A IL3388970A IL33889A IL 33889 A IL33889 A IL 33889A IL 33889 A IL33889 A IL 33889A IL 3388970 A IL3388970 A IL 3388970A IL 33889 A IL33889 A IL 33889A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- hydrogen
- formula
- solvent
- compound
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 title claims description 9
- 229940124587 cephalosporin Drugs 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- -1 nitra Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 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 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- YSJGVKHCAVGBIT-AVKWCDSFSA-N (4-nitrophenyl)methyl (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)COC1=CC=CC=C1 YSJGVKHCAVGBIT-AVKWCDSFSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229930195708 Penicillin V Natural products 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 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
-
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80582369A | 1969-03-10 | 1969-03-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33889A0 IL33889A0 (en) | 1970-04-20 |
| IL33889A true IL33889A (en) | 1973-04-30 |
Family
ID=25192601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33889A IL33889A (en) | 1969-03-10 | 1970-02-12 | Preparation of 7-amino cephalosporin esters |
Country Status (13)
-
1970
- 1970-02-06 CA CA074,173A patent/CA974516A/en not_active Expired
- 1970-02-10 IE IE176/70A patent/IE33722B1/xx unknown
- 1970-02-12 IL IL33889A patent/IL33889A/en unknown
- 1970-03-03 NL NL7003048A patent/NL7003048A/xx unknown
- 1970-03-05 BE BE746860D patent/BE746860A/xx unknown
- 1970-03-06 DE DE19702010757 patent/DE2010757A1/de active Pending
- 1970-03-06 ES ES377228A patent/ES377228A1/es not_active Expired
- 1970-03-09 SE SE7003123A patent/SE374374B/xx unknown
- 1970-03-10 CH CH351170A patent/CH529788A/de not_active IP Right Cessation
- 1970-03-10 FR FR7008534A patent/FR2037887A5/fr not_active Expired
- 1970-03-10 GB GB1266252D patent/GB1266252A/en not_active Expired
- 1970-03-10 AT AT224670A patent/AT293620B/de not_active IP Right Cessation
- 1970-03-10 JP JP45019797A patent/JPS4931999B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2037887A5 (fr) | 1970-12-31 |
| NL7003048A (enrdf_load_stackoverflow) | 1970-09-14 |
| JPS4931999B1 (enrdf_load_stackoverflow) | 1974-08-27 |
| BE746860A (fr) | 1970-09-07 |
| IE33722L (en) | 1970-09-10 |
| SE374374B (enrdf_load_stackoverflow) | 1975-03-03 |
| IE33722B1 (en) | 1974-10-02 |
| IL33889A0 (en) | 1970-04-20 |
| AT293620B (de) | 1971-10-25 |
| CH529788A (de) | 1972-10-31 |
| GB1266252A (enrdf_load_stackoverflow) | 1972-03-08 |
| CA974516A (en) | 1975-09-16 |
| ES377228A1 (es) | 1972-06-01 |
| DE2010757A1 (de) | 1970-09-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL184556B1 (pl) | Nowy sposób wytwarzania pochodnych taksanu | |
| JP2021506762A (ja) | オピカポンとその中間体の製造方法 | |
| DE2852538C2 (enrdf_load_stackoverflow) | ||
| KR100223384B1 (ko) | 삼중수화된 세픽시미(cefixime)의 제조방법 | |
| US5389627A (en) | Cephem compounds | |
| SU784766A3 (ru) | Способ получени бенз-ацил-бензимидазол(2)-производных | |
| EP0017465A1 (en) | Production of 2,6-diaminonebularines | |
| IL33889A (en) | Preparation of 7-amino cephalosporin esters | |
| US3814754A (en) | Cleavage of 7-acylamino cephalosporins | |
| SU578876A3 (ru) | Способ получени производных пиразин-4-оксида или их солей | |
| US4193918A (en) | Process for the preparation of hydroxy-alpha-amino-benzyl penicillin | |
| SU541429A3 (ru) | Способ получени производных 3-алкил-4-сульфамоиланилина или их солей | |
| KR100416673B1 (ko) | 실릴화방법 | |
| EP0882011B1 (en) | Process for preparing n-(3-amino-4-chlorophenyl) acylamides | |
| US4417047A (en) | Novel tetrazole-5-thiol ester and process for preparing cefamandole using same | |
| KR101159837B1 (ko) | Ｎ-데벤조일파크리탁셀의 반합성 제조방법 | |
| US3399207A (en) | Esters of 6-aminopenicillanic acid | |
| US4064242A (en) | 7-Acylamino-3-[1-(2,3-dihydroxypropyl)tetrazole-5-ylthiomethyl]-3-cephem-4-carboxylic acids | |
| US3052687A (en) | Process for the production of | |
| JPH0587512B2 (enrdf_load_stackoverflow) | ||
| US4251657A (en) | Method for removing protective groups | |
| SU543353A3 (ru) | Способ получени производных 7-монохлорацетамидо-3-дезацетоксицефалоспорановой кислоты | |
| KR890000523B1 (ko) | 세팔로스포린 유도체의 제조방법 | |
| JP3279195B2 (ja) | スレオ−ｎ−フタロイル−３−（３，４−ジヒドロキシフェニル）セリンの製造法 | |
| KR100213442B1 (ko) | 세펨 유도체의 새로운 제조방법 |