SE447117B - Kristallint hemisyrasalt av en molekyl 7beta-/2-(2-aminotiazol-4-yl)-(z)-2metoxiiminoacetamido/-3-/(1-metyl-1h-tetrazol-5-yl)tiometyl/-cef-3-em-4-karboxylsyra och en halv molekyl hcl eller hbr - Google Patents
Kristallint hemisyrasalt av en molekyl 7beta-/2-(2-aminotiazol-4-yl)-(z)-2metoxiiminoacetamido/-3-/(1-metyl-1h-tetrazol-5-yl)tiometyl/-cef-3-em-4-karboxylsyra och en halv molekyl hcl eller hbrInfo
- Publication number
- SE447117B SE447117B SE7909998A SE7909998A SE447117B SE 447117 B SE447117 B SE 447117B SE 7909998 A SE7909998 A SE 7909998A SE 7909998 A SE7909998 A SE 7909998A SE 447117 B SE447117 B SE 447117B
- Authority
- SE
- Sweden
- Prior art keywords
- hcl
- salt
- molecule
- carboxylic acid
- hbr
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 27
- -1 (1-METHYL-1H-TETRAZOL-5-YL) THIOMETHYL Chemical class 0.000 title claims description 23
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims description 2
- 235000019801 trisodium phosphate Nutrition 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000013078 crystal Substances 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000000634 powder X-ray diffraction Methods 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 7
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical group NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 241000588772 Morganella morganii Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000588767 Proteus vulgaris Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000249 desinfective effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229940007042 proteus vulgaris Drugs 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- CQOALHPQGSYSNO-UHFFFAOYSA-N 5h-1,3-thiazol-2-imine Chemical group N=C1SCC=N1 CQOALHPQGSYSNO-UHFFFAOYSA-N 0.000 description 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000588919 Citrobacter freundii Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 238000001159 Fisher's combined probability test Methods 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
- 241001465754 Metazoa Species 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000588777 Providencia rettgeri Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 239000003021 water soluble solvent Substances 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
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15337778A JPS5579393A (en) | 1978-12-11 | 1978-12-11 | Cephalosporin derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7909998L SE7909998L (sv) | 1980-06-12 |
| SE447117B true SE447117B (sv) | 1986-10-27 |
Family
ID=15561123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7909998A SE447117B (sv) | 1978-12-11 | 1979-12-04 | Kristallint hemisyrasalt av en molekyl 7beta-/2-(2-aminotiazol-4-yl)-(z)-2metoxiiminoacetamido/-3-/(1-metyl-1h-tetrazol-5-yl)tiometyl/-cef-3-em-4-karboxylsyra och en halv molekyl hcl eller hbr |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4298607A (no) |
| JP (1) | JPS5579393A (no) |
| BE (1) | BE880518A (no) |
| CA (1) | CA1128499A (no) |
| CH (1) | CH646437A5 (no) |
| DE (1) | DE2949485A1 (no) |
| DK (1) | DK159785C (no) |
| ES (1) | ES8100299A1 (no) |
| FR (1) | FR2444042A1 (no) |
| GB (1) | GB2036746B (no) |
| GR (1) | GR74078B (no) |
| HK (1) | HK9486A (no) |
| IT (1) | IT1126514B (no) |
| MY (1) | MY8500456A (no) |
| NL (1) | NL190487C (no) |
| NO (1) | NO158219C (no) |
| SE (1) | SE447117B (no) |
| SG (1) | SG93185G (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR78221B (no) * | 1980-02-01 | 1984-09-26 | Ciba Geigy Ag | |
| US4400503A (en) * | 1981-10-30 | 1983-08-23 | Eli Lilly And Company | Purification of syn-7-[[(2-amino-4-thiazolyl)(methoxyimino) acetyl]amino]-3-methyl-3-cephem-4-carboxylic acid |
| US4594417A (en) * | 1981-10-30 | 1986-06-10 | Eli Lilly Company | Crystalline antibiotic salt |
| US4902683A (en) * | 1984-10-25 | 1990-02-20 | The Upjohn Company | Crystalline cephalosporin hydrohalide salts |
| EP0638573A1 (en) * | 1993-08-10 | 1995-02-15 | Lucky Ltd. | Crystalline hydrates of cephalosporin and process for preparation thereof |
| ATE440101T1 (de) * | 2003-03-27 | 2009-09-15 | Basilea Pharmaceutica Ag | Cephalosporin in kristalliner form |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| FR2345153A1 (fr) * | 1976-03-25 | 1977-10-21 | Roussel Uclaf | Nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| US4166115A (en) * | 1976-04-12 | 1979-08-28 | Fujisawa Pharmaceutical Co., Ltd. | Syn 7-oxoimino substituted derivatives of cephalosporanic acid |
| GB1576625A (en) * | 1976-04-12 | 1980-10-08 | Fujisawa Pharmaceutical Co | Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof |
| JPS603314B2 (ja) * | 1976-08-31 | 1985-01-26 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
-
1978
- 1978-12-11 JP JP15337778A patent/JPS5579393A/ja active Granted
-
1979
- 1979-12-03 GR GR60660A patent/GR74078B/el unknown
- 1979-12-04 SE SE7909998A patent/SE447117B/sv not_active IP Right Cessation
- 1979-12-06 CH CH1083579A patent/CH646437A5/de not_active IP Right Cessation
- 1979-12-07 NO NO793989A patent/NO158219C/no unknown
- 1979-12-07 IT IT27924/79A patent/IT1126514B/it active
- 1979-12-07 ES ES486680A patent/ES8100299A1/es not_active Expired
- 1979-12-08 DE DE19792949485 patent/DE2949485A1/de active Granted
- 1979-12-10 BE BE0/198489A patent/BE880518A/fr not_active IP Right Cessation
- 1979-12-10 FR FR7930257A patent/FR2444042A1/fr active Granted
- 1979-12-10 DK DK524579A patent/DK159785C/da active
- 1979-12-10 CA CA341,581A patent/CA1128499A/en not_active Expired
- 1979-12-10 NL NLAANVRAGE7908869,A patent/NL190487C/xx not_active IP Right Cessation
- 1979-12-11 GB GB7942746A patent/GB2036746B/en not_active Expired
- 1979-12-11 US US06/102,525 patent/US4298607A/en not_active Expired - Lifetime
-
1985
- 1985-12-06 SG SG931/85A patent/SG93185G/en unknown
- 1985-12-30 MY MY456/85A patent/MY8500456A/xx unknown
-
1986
- 1986-02-05 HK HK94/86A patent/HK9486A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL190487B (nl) | 1993-10-18 |
| DK524579A (da) | 1980-06-12 |
| DE2949485C2 (no) | 1989-06-08 |
| IT7927924A0 (it) | 1979-12-07 |
| CA1128499A (en) | 1982-07-27 |
| IT1126514B (it) | 1986-05-21 |
| NO793989L (no) | 1980-06-12 |
| MY8500456A (en) | 1985-12-31 |
| NL190487C (nl) | 1994-03-16 |
| GB2036746B (en) | 1983-02-09 |
| BE880518A (fr) | 1980-06-10 |
| JPS5579393A (en) | 1980-06-14 |
| FR2444042B1 (no) | 1983-06-24 |
| DK159785C (da) | 1991-04-22 |
| FR2444042A1 (fr) | 1980-07-11 |
| DK159785B (da) | 1990-12-03 |
| ES486680A0 (es) | 1980-11-01 |
| HK9486A (en) | 1986-02-14 |
| DE2949485A1 (de) | 1980-06-19 |
| ES8100299A1 (es) | 1980-11-01 |
| NO158219B (no) | 1988-04-25 |
| NL7908869A (nl) | 1980-06-13 |
| CH646437A5 (de) | 1984-11-30 |
| SG93185G (en) | 1987-03-27 |
| US4298607A (en) | 1981-11-03 |
| GR74078B (no) | 1984-06-06 |
| SE7909998L (sv) | 1980-06-12 |
| GB2036746A (en) | 1980-07-02 |
| NO158219C (no) | 1988-08-03 |
| JPS636552B2 (no) | 1988-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR840001776B1 (ko) | 세프타지딤 펜타하이드레이트의 제조방법 | |
| RU2118959C1 (ru) | ГИДРОХЛОРИД 7β-[(Z)-2-(2-АМИНО-4-ТИАЗОЛИЛ)-2-ГИДРОКСИИМИНОАЦЕТАМИДО]-3-(1,2,3-ТРИАЗОЛ-4-ИЛ)-ТИОМЕТИЛТИО-3-ЦЕФЕМ-4-КАРБОНОВОЙ КИСЛОТЫ, ЕГО КРИСТАЛЛОГИДРАТ И СПОСОБ ИХ ПОЛУЧЕНИЯ | |
| SE449749B (sv) | Bis-estrar av metandiol med penicilliner och penicillansyra-1,1-dioxid | |
| US4609653A (en) | Crystalline cephem-acid addition salts and processes for their preparation | |
| SE437522B (sv) | (6r,7r)-7-/2-(2-amino-4-tiazolyl)-2-(z-metoxiimino)-acetamido/-3-(substituerad tiometyl)-cefalosporinsyra samt legre alkanoylalkyl estar/etrar derav | |
| JPS6153359B2 (no) | ||
| JP4480396B2 (ja) | カルバペネム化合物の製造方法 | |
| SE447117B (sv) | Kristallint hemisyrasalt av en molekyl 7beta-/2-(2-aminotiazol-4-yl)-(z)-2metoxiiminoacetamido/-3-/(1-metyl-1h-tetrazol-5-yl)tiometyl/-cef-3-em-4-karboxylsyra och en halv molekyl hcl eller hbr | |
| BG60439B2 (bg) | Твърда цефалоспоринова сол | |
| US20020193587A1 (en) | Penicillin crystal and process for producing the same | |
| DK148022B (da) | Fremgangsmaade til fremstilling af alfa-formen af krystallinsk natrium-o-formyl-cefamandol | |
| DE2739448A1 (de) | 7-substituierte aminoacetamido- oxadethiacephalosporine, verfahren zu deren herstellung und deren verwendung bei der behandlung bakterieller erkrankungen | |
| KR910010002B1 (ko) | 소듐 세펨 카르복실레이트의 결정의 제조방법 | |
| JP2003300985A (ja) | セフェム化合物 | |
| KR100696422B1 (ko) | 항생물질로서 사이클릭 아미노구아니딘 치환체를 가진세팔로스포린 | |
| KR890000787B1 (ko) | 세팔로스포린 유도체 성분의 주사용 또는 외용제의 제조방법 | |
| US4497811A (en) | 1-Oxadethiacephalosporin compound and antibacterial agent containing the _same | |
| IE47929B1 (en) | Substituted imidazolidinyl-3-chloro-3-cephem-4-carboxylic acids | |
| HU185685B (en) | Process for preparing new cefem-carboxylic acid derivatives | |
| US4173703A (en) | Preparation of carbamates | |
| SU980626A3 (ru) | Способ получени производных цефалоспорина или их щелочных солей | |
| US3879384A (en) | 7-{8 2-(1-and 2 cyclopenten-1-yl)acetamido{9 cephalosporanic acids | |
| KR100283591B1 (ko) | 1-베타메틸카르바페넴유도체및이의제조방법 | |
| EP0098615A1 (en) | 1-Oxadethiacephalosporin compound and antibacterial agent containing the same | |
| KR19980077157A (ko) | 세펨 유도체 제조용 중간체의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 7909998-2 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 7909998-2 Format of ref document f/p: F |