DE3431273A1 - Kristallines natriumsalz der d-6-((alpha)-(2-oxo-3-furfuryl-iden-amino-imidazolidin-1-yl)-carbonylamino)-thienyl-2-acetamido)-penicillansaeure, verfahren zur herstellung und seine verwendung in arzneimitteln - Google Patents
Kristallines natriumsalz der d-6-((alpha)-(2-oxo-3-furfuryl-iden-amino-imidazolidin-1-yl)-carbonylamino)-thienyl-2-acetamido)-penicillansaeure, verfahren zur herstellung und seine verwendung in arzneimittelnInfo
- Publication number
- DE3431273A1 DE3431273A1 DE19843431273 DE3431273A DE3431273A1 DE 3431273 A1 DE3431273 A1 DE 3431273A1 DE 19843431273 DE19843431273 DE 19843431273 DE 3431273 A DE3431273 A DE 3431273A DE 3431273 A1 DE3431273 A1 DE 3431273A1
- Authority
- DE
- Germany
- Prior art keywords
- sodium salt
- acid
- oxo
- formula
- thienyl
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 10
- 229940126601 medicinal product Drugs 0.000 title 1
- NOJNFULGOQGBKB-UHFFFAOYSA-M sodium;3-[3-tert-butylsulfanyl-1-[[4-(6-ethoxypyridin-3-yl)phenyl]methyl]-5-[(5-methylpyridin-2-yl)methoxy]indol-2-yl]-2,2-dimethylpropanoate Chemical compound [Na+].C1=NC(OCC)=CC=C1C(C=C1)=CC=C1CN1C2=CC=C(OCC=3N=CC(C)=CC=3)C=C2C(SC(C)(C)C)=C1CC(C)(C)C([O-])=O NOJNFULGOQGBKB-UHFFFAOYSA-M 0.000 title 1
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- -1 2-oxo-3- furfurylideneamino-imidazolidin-1-yl Chemical group 0.000 abstract description 3
- ZMXDDKWLCZADIW-YYWVXINBSA-N N,N-dimethylformamide-d7 Chemical compound [2H]C(=O)N(C([2H])([2H])[2H])C([2H])([2H])[2H] ZMXDDKWLCZADIW-YYWVXINBSA-N 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WNPVZANXRCPJPW-UHFFFAOYSA-N 5-[isocyano-(4-methylphenyl)sulfonylmethyl]-1,2,3-trimethoxybenzene Chemical compound COC1=C(OC)C(OC)=CC(C([N+]#[C-])S(=O)(=O)C=2C=CC(C)=CC=2)=C1 WNPVZANXRCPJPW-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- YCOFRPYSZKIPBQ-UHFFFAOYSA-N penicillic acid Natural products COC1=CC(=O)OC1(O)C(C)=C YCOFRPYSZKIPBQ-UHFFFAOYSA-N 0.000 description 5
- VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 4
- 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 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GAQWDBUWBUOFLS-UHFFFAOYSA-N (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid;hydrate Chemical compound O.C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C GAQWDBUWBUOFLS-UHFFFAOYSA-N 0.000 description 1
- HOWSSPXWUOKFGP-UHFFFAOYSA-N 1-(furan-2-ylmethylideneamino)imidazolidin-2-one Chemical compound O=C1NCCN1N=CC1=CC=CO1 HOWSSPXWUOKFGP-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000002983 circular dichroism Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001291 vacuum drying 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
- 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
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/70—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with hetero rings as additional substituents on the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843431273 DE3431273A1 (de) | 1984-08-25 | 1984-08-25 | Kristallines natriumsalz der d-6-((alpha)-(2-oxo-3-furfuryl-iden-amino-imidazolidin-1-yl)-carbonylamino)-thienyl-2-acetamido)-penicillansaeure, verfahren zur herstellung und seine verwendung in arzneimitteln |
| NO853188A NO853188L (no) | 1984-08-25 | 1985-08-13 | Krystallinsk natriumsalt av d-6-(d-((2-okso-3-furfuryli-den-amino-imidazolidin-1-yl)karbonyl-amino)-tienyl-2-acet-amido)-penicillansyre, fremgangsmaate til dens fremstilling og dens anvendelse i legemidler. |
| AT85110189T ATE34576T1 (de) | 1984-08-25 | 1985-08-14 | Kristallines natriumsalz der d-6-(alpha-((2-oxo-3-furfuryliden-amino-imidazo idin-1yl)carbonylamino>-thienyl-2-acetamido)- penicillansaeure, verfahren zur herstellung und seine verwendung in arzneimitteln. |
| DE8585110189T DE3562918D1 (en) | 1984-08-25 | 1985-08-14 | Crystalline sodium salt of d-6-(alpha-û(2-oxo-3-furfurylidene-amino-imidazolidin-1-yl)carbonylamine¨-thienyl-2-acetamido)-penicillanic acid, process for its preparation and its use in pharmaceutical compounds |
| EP85110189A EP0176716B1 (de) | 1984-08-25 | 1985-08-14 | Kristallines Natriumsalz der D-6-(alpha-[(2-Oxo-3-furfuryliden-amino-imidazolidin-1-yl)carbonylamino]-thienyl-2-acetamido)-penicillansäure, Verfahren zur Herstellung und seine Verwendung in Arzneimitteln |
| FI853211A FI853211L (fi) | 1984-08-25 | 1985-08-21 | Kristalliniskt natriumsalt av d-6/ -/(2-oxo-3-furfurylden-amino-imidazolin-1-yl)karbonylamino/-tienyl -2-acetamido/-penicillansyra, foerfarande foer dess framstaellning och dess anvaendning i laekemedel. |
| IL76164A IL76164A0 (en) | 1984-08-25 | 1985-08-22 | Crystalline sodium salt of d-6-(alpha-((2-oxo-3-furfurylidene-amino-imidazolidin-1-yl)carbonylamino)-2-thienylacetamido)-penicillanic acid,its preparation and pharmaceutical compositions containing it |
| NZ213198A NZ213198A (en) | 1984-08-25 | 1985-08-22 | The crystalline sodium salt of a penicillanic acid derivative, preparation and pharmaceutical compositions |
| AU46577/85A AU559040B2 (en) | 1984-08-25 | 1985-08-22 | Penicilline derivative |
| PH32687A PH21842A (en) | 1984-08-25 | 1985-08-23 | Crystalline sodium salt of d-6-o(-(2-oxo-3-furfurylidene-amino-imidazolidin-1-yl)carbonyl-amino)-2-thienylacetamido-penicillanic acid |
| PT81014A PT81014B (pt) | 1984-08-25 | 1985-08-23 | Processo de preparacao do sal cristalino de sodio do acido d-6-< alfa-{(2-oxo-3-furfurilidenoamino-imidazolidin-1-il)-carbonilamino}-2-tienilacetamido>- penicilamico util como medicamento |
| DK385085A DK385085A (da) | 1984-08-25 | 1985-08-23 | Krystallinsk natriumsalt af d-6-(alfa-((2-oxo-3-furfuryliden-aminoimidazolidin-1-yl)carbonylamino)-thienyl-2-acetamido)-penicillansyre, fremgangsmaade til dets fremstilling til dets anvendelse i laegemidler |
| HU853216A HU194893B (en) | 1984-08-25 | 1985-08-23 | Process for producing cristalline sodium salt of d-6-brace alpha-(/2-oxo-3-furfuriliden-amino-imidazolidin-1-yl/-carbonyl-amino)-thienyl-2-acetamido-brace closed-penicillanic acid and pharmaceutical compositions containing them |
| JP60185652A JPS6157589A (ja) | 1984-08-25 | 1985-08-23 | 純粋な結晶の形態のＤ‐６‐｛α‐［（２‐オキソ‐３‐フルフリリデン‐アミノ‐イミダゾリジン‐１‐イル）‐カルボニルアミノ］‐２‐チエニルアセタミド｝‐ペニシラン酸のナトリウム塩、その製造方法およびその薬物における使用 |
| ZA856413A ZA856413B (en) | 1984-08-25 | 1985-08-23 | Crystalline sodium salt of d-6-(alpha-((2-oxo-3-furfurylidene-amino-imidazolidin-1-yl)carbonylamino)-2-thienylacetamido)-pencillanic acid,processes for its preparation and its use in medicaments |
| ES546379A ES8609340A1 (es) | 1984-08-25 | 1985-08-23 | Sal sodica del acido d-6-(a-(2-oxo-3-furfurilidenaminoimida-zolidin-1-il)-carbonilamino)-tienil-2-acetamido)-penicilani-co |
| GR852047A GR852047B (OSRAM) | 1984-08-25 | 1985-08-23 | |
| KR1019850006132A KR860001818A (ko) | 1984-08-25 | 1985-08-24 | D-6-｛α-〔(2-옥소-3- 푸르푸릴리덴- 아미노-이미다졸리딘-1-일)카르보닐아미노〕-2-티에닐아세트아미도｝-페니실란산의 결정성 나트륨의 제조방법 |
| CN85106479A CN85106479B (zh) | 1984-08-25 | 1985-08-29 | 晶状的右旋-6-{α-[(2-氧代-3-亚糠基-氨基-咪唑烷-1-基)碳酰氨基]-2-噻吩基乙酰氨基}-青霉烷酸钠盐制备方法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843431273 DE3431273A1 (de) | 1984-08-25 | 1984-08-25 | Kristallines natriumsalz der d-6-((alpha)-(2-oxo-3-furfuryl-iden-amino-imidazolidin-1-yl)-carbonylamino)-thienyl-2-acetamido)-penicillansaeure, verfahren zur herstellung und seine verwendung in arzneimitteln |
| CN85106479A CN85106479B (zh) | 1984-08-25 | 1985-08-29 | 晶状的右旋-6-{α-[(2-氧代-3-亚糠基-氨基-咪唑烷-1-基)碳酰氨基]-2-噻吩基乙酰氨基}-青霉烷酸钠盐制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3431273A1 true DE3431273A1 (de) | 1986-03-06 |
Family
ID=25741999
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843431273 Withdrawn DE3431273A1 (de) | 1984-08-25 | 1984-08-25 | Kristallines natriumsalz der d-6-((alpha)-(2-oxo-3-furfuryl-iden-amino-imidazolidin-1-yl)-carbonylamino)-thienyl-2-acetamido)-penicillansaeure, verfahren zur herstellung und seine verwendung in arzneimitteln |
| DE8585110189T Expired DE3562918D1 (en) | 1984-08-25 | 1985-08-14 | Crystalline sodium salt of d-6-(alpha-û(2-oxo-3-furfurylidene-amino-imidazolidin-1-yl)carbonylamine¨-thienyl-2-acetamido)-penicillanic acid, process for its preparation and its use in pharmaceutical compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585110189T Expired DE3562918D1 (en) | 1984-08-25 | 1985-08-14 | Crystalline sodium salt of d-6-(alpha-û(2-oxo-3-furfurylidene-amino-imidazolidin-1-yl)carbonylamine¨-thienyl-2-acetamido)-penicillanic acid, process for its preparation and its use in pharmaceutical compounds |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0176716B1 (OSRAM) |
| JP (1) | JPS6157589A (OSRAM) |
| KR (1) | KR860001818A (OSRAM) |
| CN (1) | CN85106479B (OSRAM) |
| AT (1) | ATE34576T1 (OSRAM) |
| AU (1) | AU559040B2 (OSRAM) |
| DE (2) | DE3431273A1 (OSRAM) |
| DK (1) | DK385085A (OSRAM) |
| ES (1) | ES8609340A1 (OSRAM) |
| FI (1) | FI853211L (OSRAM) |
| GR (1) | GR852047B (OSRAM) |
| HU (1) | HU194893B (OSRAM) |
| IL (1) | IL76164A0 (OSRAM) |
| NO (1) | NO853188L (OSRAM) |
| NZ (1) | NZ213198A (OSRAM) |
| PH (1) | PH21842A (OSRAM) |
| PT (1) | PT81014B (OSRAM) |
| ZA (1) | ZA856413B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW347383B (en) * | 1995-10-26 | 1998-12-11 | Biochemie Gmbh | A process for the production of a crystalline sodium salt of amoxicillin in ethanol as solvent |
| US9844374B2 (en) | 2014-12-18 | 2017-12-19 | Ethicon Llc | Surgical instrument systems comprising an articulatable end effector and means for adjusting the firing stroke of a firing member |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL85039B1 (pl) * | 1972-02-17 | 1977-02-26 | Tarchomińskie Zakłady Farmaceutyczne | Sposób wytwarzania soli sodowej a-ftminobenzylopeiiicylmy |
| PL87153B1 (pl) * | 1973-07-13 | 1976-12-15 | Tarchomińskie Zakłady Farmaceutyczne | Sposób otrzymywania krystalicznej soli dwusodowej penicyliny a-karboksybenzylowej |
| DE2732283A1 (de) * | 1977-07-16 | 1979-01-25 | Bayer Ag | Beta-lactam-verbindungen |
| DE2732323A1 (de) * | 1977-07-16 | 1979-01-25 | Bayer Ag | Beta-lactam-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung |
| JPS5940727A (ja) * | 1982-07-28 | 1984-03-06 | Fujitsu Ltd | 自動等化方式 |
-
1984
- 1984-08-25 DE DE19843431273 patent/DE3431273A1/de not_active Withdrawn
-
1985
- 1985-08-13 NO NO853188A patent/NO853188L/no unknown
- 1985-08-14 EP EP85110189A patent/EP0176716B1/de not_active Expired
- 1985-08-14 AT AT85110189T patent/ATE34576T1/de active
- 1985-08-14 DE DE8585110189T patent/DE3562918D1/de not_active Expired
- 1985-08-21 FI FI853211A patent/FI853211L/fi not_active Application Discontinuation
- 1985-08-22 NZ NZ213198A patent/NZ213198A/xx unknown
- 1985-08-22 IL IL76164A patent/IL76164A0/xx unknown
- 1985-08-22 AU AU46577/85A patent/AU559040B2/en not_active Ceased
- 1985-08-23 JP JP60185652A patent/JPS6157589A/ja active Pending
- 1985-08-23 ZA ZA856413A patent/ZA856413B/xx unknown
- 1985-08-23 HU HU853216A patent/HU194893B/hu not_active IP Right Cessation
- 1985-08-23 GR GR852047A patent/GR852047B/el unknown
- 1985-08-23 ES ES546379A patent/ES8609340A1/es not_active Expired
- 1985-08-23 DK DK385085A patent/DK385085A/da not_active Application Discontinuation
- 1985-08-23 PT PT81014A patent/PT81014B/pt not_active IP Right Cessation
- 1985-08-23 PH PH32687A patent/PH21842A/en unknown
- 1985-08-24 KR KR1019850006132A patent/KR860001818A/ko not_active Abandoned
- 1985-08-29 CN CN85106479A patent/CN85106479B/zh not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL76164A0 (en) | 1985-12-31 |
| HUT38354A (en) | 1986-05-28 |
| ATE34576T1 (de) | 1988-06-15 |
| HU194893B (en) | 1988-03-28 |
| DE3562918D1 (en) | 1988-06-30 |
| ES546379A0 (es) | 1986-07-16 |
| NO853188L (no) | 1986-02-26 |
| FI853211A0 (fi) | 1985-08-21 |
| EP0176716B1 (de) | 1988-05-25 |
| PH21842A (en) | 1988-03-17 |
| CN85106479A (zh) | 1987-03-18 |
| PT81014A (en) | 1985-09-01 |
| KR860001818A (ko) | 1986-03-22 |
| EP0176716A1 (de) | 1986-04-09 |
| FI853211A7 (fi) | 1986-02-26 |
| JPS6157589A (ja) | 1986-03-24 |
| NZ213198A (en) | 1989-02-24 |
| AU4657785A (en) | 1986-02-27 |
| PT81014B (pt) | 1987-12-30 |
| AU559040B2 (en) | 1987-02-19 |
| DK385085A (da) | 1986-02-26 |
| DK385085D0 (da) | 1985-08-23 |
| ZA856413B (en) | 1986-04-30 |
| CN85106479B (zh) | 1988-07-27 |
| ES8609340A1 (es) | 1986-07-16 |
| FI853211L (fi) | 1986-02-26 |
| GR852047B (OSRAM) | 1985-12-20 |
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| Date | Code | Title | Description |
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| 8130 | Withdrawal |