CA1132905A - Antibiotique - Google Patents

Antibiotique

Info

Publication number: CA1132905A
Authority: CA; Canada
Prior art keywords: vial; hydrate; vacuum; ttc; acid salt
Prior art date: 1976-08-31
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.): Expired

Application number

CA385,979A

Other languages

English (en)

Inventor

Kenzo Ishizuka

Hiroshi Fujisawa

Etsunosuke Noda

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date (The priority date 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 date listed.)

1976-08-31

Filing date

1981-09-15

Publication date

1982-10-05

1976-08-31 Priority claimed from JP10458276A external-priority patent/JPS5329936A/ja

1981-09-15 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1981-09-15 Priority to CA385,979A priority Critical patent/CA1132905A/fr

1982-10-05 Application granted granted Critical

1982-10-05 Publication of CA1132905A publication Critical patent/CA1132905A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 40
230000003115 biocidal effect Effects 0.000 title claims abstract description 11
125000005588 carbonic acid salt group Chemical group 0.000 claims abstract description 18
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 9
239000007787 solid Substances 0.000 claims abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
238000000034 method Methods 0.000 claims description 26
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 16
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 8
235000017557 sodium bicarbonate Nutrition 0.000 claims description 8
229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims description 2
238000007789 sealing Methods 0.000 claims description 2
QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical group Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 claims 2
238000012856 packing Methods 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 35
239000013078 crystal Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 18
239000000243 solution Substances 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000004090 dissolution Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
-1 alkali metal hydrogen carbonates Chemical class 0.000 description 6
239000012153 distilled water Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000007924 injection Substances 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
238000005406 washing Methods 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
206010024769 Local reaction Diseases 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000011049 filling Methods 0.000 description 5
238000000634 powder X-ray diffraction Methods 0.000 description 5
235000017550 sodium carbonate Nutrition 0.000 description 5
229940001593 sodium carbonate Drugs 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
241000282414 Homo sapiens Species 0.000 description 4
206010020565 Hyperaemia Diseases 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
239000000645 desinfectant Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
208000035473 Communicable disease Diseases 0.000 description 3
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
150000008041 alkali metal carbonates Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
150000004677 hydrates Chemical class 0.000 description 3
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 3
239000001095 magnesium carbonate Substances 0.000 description 3
229910000021 magnesium carbonate Inorganic materials 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
230000017074 necrotic cell death Effects 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
235000002639 sodium chloride Nutrition 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
125000002769 thiazolinyl group Chemical group 0.000 description 3
ODDAWJGQWOGBCX-UHFFFAOYSA-N 1-[2-(dimethylazaniumyl)ethyl]tetrazole-5-thiolate Chemical compound CN(C)CCN1N=NN=C1S ODDAWJGQWOGBCX-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000588772 Morganella morganii Species 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
241000588767 Proteus vulgaris Species 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
239000003086 colorant Substances 0.000 description 2
230000007850 degeneration Effects 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000003589 local anesthetic agent Substances 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000006864 oxidative decomposition reaction Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229940007042 proteus vulgaris Drugs 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
241000272496 Galliformes Species 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
238000005481 NMR spectroscopy Methods 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
231100000369 acute toxicity data Toxicity 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
230000002924 anti-infective effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
150000004687 hexahydrates Chemical class 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
208000014674 injury Diseases 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
239000002370 magnesium bicarbonate Substances 0.000 description 1
235000014824 magnesium bicarbonate Nutrition 0.000 description 1
229960002660 mepivacaine hydrochloride Drugs 0.000 description 1
RETIMRUQNCDCQB-UHFFFAOYSA-N mepivacaine hydrochloride Chemical compound Cl.CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C RETIMRUQNCDCQB-UHFFFAOYSA-N 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
210000000663 muscle cell Anatomy 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000004686 pentahydrates Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
210000003314 quadriceps muscle Anatomy 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
102220043690 rs1049562 Human genes 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000005201 scrubbing Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940083542 sodium Drugs 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229960002668 sodium chloride Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical group C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

CA385,979A 1976-08-31 1981-09-15 Antibiotique Expired CA1132905A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA385,979A CA1132905A (fr)	1976-08-31	1981-09-15	Antibiotique

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP10458276A JPS5329936A (en)	1976-08-31	1976-08-31	Antibiotic composition
JP104582/1976		1976-08-31
CA285,794A CA1109795A (fr)	1976-08-31	1977-08-30	Compose pharmaceutique contenant de la cephalosporine et un sel de l'acide carbonique
CA385,979A CA1132905A (fr)	1976-08-31	1981-09-15	Antibiotique

Publications (1)

Publication Number	Publication Date
CA1132905A true CA1132905A (fr)	1982-10-05

Family

ID=27165256

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA385,979A Expired CA1132905A (fr)	1976-08-31	1981-09-15	Antibiotique

Country Status (1)

Country	Link
CA (1)	CA1132905A (fr)

1981
- 1981-09-15 CA CA385,979A patent/CA1132905A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-10-05	MKEX	Expiry

Publication	Publication Date	Title
US4161527A (en)	1979-07-17	Antibiotic compositions
KR840001776B1 (ko)	1984-10-19	세프타지딤 펜타하이드레이트의 제조방법
PL172835B1 (pl)	1997-12-31	Chlorowodorek kwasu 7- ß -[(Z)-2-(2-amino-4-tiazolilo)-2-hydroksyiminoacetamido]-3-(1,2,3-triazol-4-ilo)-tiometylotio-3 -cefemo-4-karboksylowego oraz sposób jego wytwarzania, krystaliczny wodzian chlorowodorku kwasu 7- ß -(Z)-2-(2-amino-4-tiazolilo)-2-hydroksyiminoacetamido]-3-(1,2,3-triazol-4-ilo)-tiometylotio-3-ce- femo-4-karboksylowego oraz sposób jego wytwarzania PL PL PL PL PL
IE59613B1 (en)	1994-03-09	A crystalline oral cephalosporin hydrate and its compositions
DE1795292B2 (de)	1974-08-29	Cephalosporinderivate und Verfahren zu deren Herstellung
JPH08505645A (ja)	1996-06-18	結晶性ペニシリン誘導体並びにその製造及び使用
IE58639B1 (en)	1993-10-20	9-substituted guanine monohydrates
IE67447B1 (en)	1996-04-03	Cephalosporin salts and injectable compositions
IE47230B1 (en)	1984-01-25	A new crystalline form of the sodium salt of an oxime derivative of 7-amino-thiazolyl-acetamido-cephalosporanic acid, a process for preparing it and pharmaceutical compositions containing it
IE50269B1 (en)	1986-03-19	Improvements in or relating to a cephalosporin antibiotic
SU1324586A3 (ru)	1987-07-15	Способ получени производного 7 @ -[(Z)-2-(2-аминотиазол-4-ил)-2-оксииминоацетамидо]-3-цефем-4-карбоновой кислоты или его соли щелочного металла
DD282691A5 (de)	1990-09-19	Verfahren zur herstellung von cephalosporin
US3813388A (en)	1974-05-28	7-(d-(alpha-amino-alpha-phenyl-,2-thienyl-and 3-thienyl-acetamido))-3-(s-(2-methyl-1,2,3-triazole-4-yl)thiomethyl)-3-cephem-4-carboxylic acids
JPH06500769A (ja)	1994-01-27	抗菌性ペネムエステル誘導体
CA1132905A (fr)	1982-10-05	Antibiotique
US4189479A (en)	1980-02-19	Cephalosporin esters
JPS5917117B2 (ja)	1984-04-19	抗菌剤の製法
JPH03500536A (ja)	1991-02-07	セファロスポリン抗生物質類
JP2003300985A (ja)	2003-10-21	セフェム化合物
US3539562A (en)	1970-11-10	Alpha - amino - 2,4,6 - cycloheptatrienylmethylcephalosporins
JPH06503805A (ja)	1994-04-28	ペネム化合物
US6034076A (en)	2000-03-07	Stable hydrates of a cephalosporin chloride salt
JP3148235B2 (ja)	2001-03-19	抗菌性ペネム化合物
US4046904A (en)	1977-09-06	Novel penicillin, and its preparation and use
JP2000514832A (ja)	2000-11-07	抗菌性の置換７−アシルアミノ−３−（メチルヒドラゾノ）メチルセファロスポリンおよび中間体