IL31807A - Process for the n-acylation of 6-aminopenicillanic acid - Google Patents
Process for the n-acylation of 6-aminopenicillanic acidInfo
- Publication number
- IL31807A IL31807A IL31807A IL3180769A IL31807A IL 31807 A IL31807 A IL 31807A IL 31807 A IL31807 A IL 31807A IL 3180769 A IL3180769 A IL 3180769A IL 31807 A IL31807 A IL 31807A
- Authority
- IL
- Israel
- Prior art keywords
- polymer
- solution
- acid
- acylating
- acylation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 title claims description 12
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 title claims description 12
- 238000005917 acylation reaction Methods 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims description 35
- 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 description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 229930182555 Penicillin Natural products 0.000 claims description 9
- 231100000252 nontoxic Toxicity 0.000 claims description 8
- 230000003000 nontoxic effect Effects 0.000 claims description 8
- 230000006181 N-acylation Effects 0.000 claims description 6
- 229940049954 penicillin Drugs 0.000 claims description 6
- 150000002960 penicillins Chemical class 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229920005615 natural polymer Polymers 0.000 claims description 2
- 239000011343 solid material Substances 0.000 claims description 2
- 229920001059 synthetic polymer Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- -1 dibenzylaine Chemical compound 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000019371 penicillin G benzathine Nutrition 0.000 description 4
- 229940056360 penicillin g Drugs 0.000 description 4
- BONORWCBNONWAT-UHFFFAOYSA-N 4-ethenyl-2-nitrophenol Chemical compound OC1=CC=C(C=C)C=C1[N+]([O-])=O BONORWCBNONWAT-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007979 citrate buffer Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101710084464 Purine nucleoside phosphorylase DeoD-type 2 Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 229960003669 carbenicillin Drugs 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 229960004894 pheneticillin Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/22—Oxygen
- C08F212/24—Phenols or alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/10—Acylation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB03840/68A GB1268631A (en) | 1968-03-21 | 1968-03-21 | Penicillins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31807A0 IL31807A0 (en) | 1969-05-28 |
| IL31807A true IL31807A (en) | 1973-03-30 |
Family
ID=10030313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31807A IL31807A (en) | 1968-03-21 | 1969-03-13 | Process for the n-acylation of 6-aminopenicillanic acid |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4948436B1 (cs) |
| AT (1) | AT285816B (cs) |
| BE (1) | BE730272A (cs) |
| BR (1) | BR6907214D0 (cs) |
| CH (1) | CH537414A (cs) |
| CS (1) | CS154638B2 (cs) |
| DE (1) | DE1913486A1 (cs) |
| DK (1) | DK131861C (cs) |
| ES (1) | ES364962A1 (cs) |
| FI (1) | FI50424C (cs) |
| FR (1) | FR2035797B1 (cs) |
| GB (1) | GB1268631A (cs) |
| IE (1) | IE32664B1 (cs) |
| IL (1) | IL31807A (cs) |
| NL (1) | NL6904041A (cs) |
| PL (1) | PL79945B1 (cs) |
| SE (1) | SE359094B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794118A (fr) * | 1972-01-18 | 1973-07-16 | Yeda Research And Dev Cy Ltd | Procede d'acylation d'acides carboxyliques |
-
1968
- 1968-03-21 GB GB03840/68A patent/GB1268631A/en not_active Expired
-
1969
- 1969-03-07 IE IE306/69A patent/IE32664B1/xx unknown
- 1969-03-13 IL IL31807A patent/IL31807A/en unknown
- 1969-03-14 NL NL6904041A patent/NL6904041A/xx unknown
- 1969-03-17 DE DE19691913486 patent/DE1913486A1/de active Pending
- 1969-03-17 BR BR207214/69A patent/BR6907214D0/pt unknown
- 1969-03-18 ES ES364962A patent/ES364962A1/es not_active Expired
- 1969-03-18 SE SE03761/69A patent/SE359094B/xx unknown
- 1969-03-19 CH CH417269A patent/CH537414A/de not_active IP Right Cessation
- 1969-03-19 AT AT272269A patent/AT285816B/de not_active IP Right Cessation
- 1969-03-19 DK DK150069A patent/DK131861C/da active
- 1969-03-20 FI FI690816A patent/FI50424C/fi active
- 1969-03-20 PL PL1969132469A patent/PL79945B1/pl unknown
- 1969-03-20 JP JP44020797A patent/JPS4948436B1/ja active Pending
- 1969-03-20 CS CS200069A patent/CS154638B2/cs unknown
- 1969-03-20 FR FR6908017A patent/FR2035797B1/fr not_active Expired
- 1969-03-21 BE BE730272D patent/BE730272A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH537414A (de) | 1973-05-31 |
| GB1268631A (en) | 1972-03-29 |
| PL79945B1 (cs) | 1975-08-30 |
| IE32664B1 (en) | 1973-10-17 |
| FR2035797B1 (cs) | 1974-01-11 |
| FI50424B (cs) | 1975-12-01 |
| DK131861C (da) | 1976-03-22 |
| ES364962A1 (es) | 1971-02-16 |
| SE359094B (cs) | 1973-08-20 |
| NL6904041A (cs) | 1969-09-23 |
| IE32664L (en) | 1969-09-21 |
| AT285816B (de) | 1970-11-10 |
| FR2035797A1 (cs) | 1970-12-24 |
| BE730272A (cs) | 1969-09-01 |
| BR6907214D0 (pt) | 1973-03-13 |
| FI50424C (fi) | 1976-03-10 |
| DK131861B (da) | 1975-09-15 |
| IL31807A0 (en) | 1969-05-28 |
| CS154638B2 (cs) | 1974-04-30 |
| DE1913486A1 (de) | 1969-10-30 |
| JPS4948436B1 (cs) | 1974-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3980637A (en) | Production of amoxicillin | |
| EP0399094A2 (en) | Improved process for the preparation of ceftriaxone | |
| FI59413C (fi) | Foerfarande foer framstaellning av 6-d(-)-alfa-amino-p-acetoxifenylacetamido penicillansyra anvaendbar saosom antibakteriskt aemne | |
| IL31807A (en) | Process for the n-acylation of 6-aminopenicillanic acid | |
| DE1670113B2 (de) | Ester der 6-aminopenicillansaeure und verfahren zu ihrer herstellung | |
| NO167098B (no) | Modulaer beskyttelsesstruktur for undervannsinstallasjoner. | |
| US4193918A (en) | Process for the preparation of hydroxy-alpha-amino-benzyl penicillin | |
| KR830002454B1 (ko) | 7-아미노-데스아세톡시 세파로스포란산 유도체의 제조방법 | |
| JPH072750B2 (ja) | ６−Ｄ−α−（４−エチル−２，３−ジオクソ−１−ピペラジノカルボニルアミノ）−フエニルアセトアミド−ペニシラン酸の製造方法 | |
| KR830001969B1 (ko) | 6―｛D―(―) α-(4―에틸-2. 3-디옥소-1 피페라지노카보닐아미노) 페닐(또는 하이드록시페닐)아세트아미도 페니실란산 및 그 염의 제조방법 | |
| US3284451A (en) | Activated esters of 7-amino-cephalosporanic acid | |
| IL99263A (en) | Preparation of crystalline 7-amino-3(5-carboxymethyl-4-methyl-1,3-thiazol-2-ylthiomethyl)-ceph-3-em-4-carboxylic acid | |
| CH617201A5 (cs) | ||
| US3196151A (en) | Derivatives of 7-aminocephalosporanic acid | |
| US4160086A (en) | 3-Heterocyclicthio-7-α-carboxy 2-aryl acetamido cephalosporanic acid | |
| KR840000115B1 (ko) | 카바졸 유도체의 제조방법 | |
| RU2123500C1 (ru) | Способ получения n-итаконоилхитозана | |
| US3864332A (en) | Method of preparing {60 -aminobenzlpenicillin | |
| CA1225954A (en) | Process for the preparation of cephem compounds | |
| SU802290A1 (ru) | Способ получени карбоксилсодер-жАщиХ пРОизВОдНыХ ХиТОзАНА | |
| JP2001517248A (ja) | β−ラクタム抗生物質の製造で有用なアミノチアゾール誘導体 | |
| US3531469A (en) | Derivatives of penicillanic acid | |
| US4107179A (en) | Method for preparing ticrynafen | |
| US4007178A (en) | O-acyl-7-acylaminocephalosporadesic acids | |
| SU197948A1 (ru) | Способ получени водорастворимых полимерных производных хлорэтиламинов |