JPS5824589A - 生化学的に活性のヒドラゾノセフエム誘導体 - Google Patents

生化学的に活性のヒドラゾノセフエム誘導体

Info

Publication number: JPS5824589A
Authority: JP; Japan
Prior art keywords: methyl; tetrazol; solution; derivative; hydrazinocephem
Prior art date: 1981-07-21
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.): Pending

Application number

JP57125241A

Other languages

English (en)

Japanese (ja)

Inventor

ピエロ・ベラニ

ジアン・ピエトロ・ブロツカリ

ジオルダノ・ブル−ノ・コルシ−

セルジオ・イノセンチ

ウンベルト・バルカビ

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.)

KURAFU SUUDO

Original Assignee

KURAFU SUUDO

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.)

1981-07-21

Filing date

1982-07-20

Publication date

1983-02-14

1982-07-20 Application filed by KURAFU SUUDO filed Critical KURAFU SUUDO

1983-02-14 Publication of JPS5824589A publication Critical patent/JPS5824589A/ja

Status Pending legal-status Critical Current

Links

-1 Hydrazinocephem derivatives Chemical class 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 14
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 5
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
239000003586 protic polar solvent Substances 0.000 claims description 3
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
239000000243 solution Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
239000002244 precipitate Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000005973 Carvone Substances 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
239000007787 solid Substances 0.000 description 4
VMASTYPGLHRVNL-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetic acid Chemical compound NC1=NC(C(=O)C(O)=O)=CS1 VMASTYPGLHRVNL-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
239000000908 ammonium hydroxide Substances 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
JPJMIBGVCGNFQD-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CSC(NC=O)=N1 JPJMIBGVCGNFQD-UHFFFAOYSA-N 0.000 description 1
CIBONMJTQXKNEA-UHFFFAOYSA-N 2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NC(=O)CCl)=N1 CIBONMJTQXKNEA-UHFFFAOYSA-N 0.000 description 1
IXVJKFCFNGQJTG-UHFFFAOYSA-N 3-oxopropanoyl 3-oxopropanoate Chemical compound O=CCC(=O)OC(=O)CC=O IXVJKFCFNGQJTG-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
108020004256 Beta-lactamase Proteins 0.000 description 1
229930186147 Cephalosporin Natural products 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
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
102000006635 beta-lactamase Human genes 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 1
229960001139 cefazolin Drugs 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
PYHXGXCGESYPCW-UHFFFAOYSA-N diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000000034 method Methods 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
SOEVVANXSDKPIY-UHFFFAOYSA-M sodium glyoxylate Chemical compound [Na+].[O-]C(=O)C=O SOEVVANXSDKPIY-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP57125241A 1981-07-21 1982-07-20 生化学的に活性のヒドラゾノセフエム誘導体 Pending JPS5824589A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT8123033A IT1211080B (it)	1981-07-21	1981-07-21	Idrazonocefem derivati biologicamente attivi.
IT23033A/81		1981-07-21

Publications (1)

Publication Number	Publication Date
JPS5824589A true JPS5824589A (ja)	1983-02-14

Family

ID=11203099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57125241A Pending JPS5824589A (ja)	1981-07-21	1982-07-20	生化学的に活性のヒドラゾノセフエム誘導体

Country Status (7)

Country	Link
JP (1)	JPS5824589A (it)
DE (1)	DE3227284A1 (it)
ES (1)	ES514106A0 (it)
FR (1)	FR2510117B1 (it)
GB (1)	GB2102423B (it)
IT (1)	IT1211080B (it)
PT (1)	PT75281A (it)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT381944B (de) *	1984-04-10	1986-12-10	Biochemie Gmbh	Verfahren zur herstellung von cephalosporinantibiotika
CA2783572C (en)	2005-12-07	2016-08-09	Basilea Pharmaceutica Ag	Useful combinations of monobactam antibiotics with beta-lactamase inhibitors
EP2105435A4 (en) *	2007-01-10	2011-06-15	Mitsubishi Tanabe Pharma Corp	Hydrazone derivative
CN112010821A (zh) *	2020-09-29	2020-12-01	山东金城医药化工有限公司	氨噻肟酸乙酯的回收方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1208015A (en) *	1967-03-23	1970-10-07	Glaxo Lab Ltd	Cephalosporins
GB1208014A (en) *	1967-03-23	1970-10-07	Glaxo Lab Ltd	Cephalosporins
DK400074A (it)	1973-10-01	1975-06-09	Ciba Geigy Ag
IT1081809B (it) *	1977-06-07	1985-05-21	Isf Spa	Idrazono cefalosporine
DE2818263A1 (de) *	1978-04-26	1979-11-08	Bayer Ag	Beta-lactamantibiotika

1981
- 1981-07-21 IT IT8123033A patent/IT1211080B/it active
1982
- 1982-07-15 FR FR8212347A patent/FR2510117B1/fr not_active Expired
- 1982-07-19 ES ES514106A patent/ES514106A0/es active Granted
- 1982-07-20 JP JP57125241A patent/JPS5824589A/ja active Pending
- 1982-07-20 GB GB08220930A patent/GB2102423B/en not_active Expired
- 1982-07-20 PT PT75281A patent/PT75281A/pt unknown
- 1982-07-21 DE DE19823227284 patent/DE3227284A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
IT8123033A0 (it)	1981-07-21
GB2102423A (en)	1983-02-02
PT75281A (en)	1982-08-01
FR2510117A1 (fr)	1983-01-28
FR2510117B1 (fr)	1985-07-05
ES8304997A1 (es)	1983-04-01
DE3227284A1 (de)	1983-02-24
ES514106A0 (es)	1983-04-01
GB2102423B (en)	1985-08-14
IT1211080B (it)	1989-09-29

Publication	Publication Date	Title
DE2727753C2 (it)	1987-11-05
DE2715385C2 (it)	1991-10-17
DE2461478C2 (de)	1982-04-15	Cephalosporinderivate und Verfahren zu deren Herstellung
JPS5834474B2 (ja)	1983-07-27	チアゾリジン誘導体の製造法
GB1599722A (en)	1981-10-07	Cephalosporin derivatives
US3989694A (en)	1976-11-02	7-Acyl-3-(substituted triazolyl thiomethyl)cephalosporins
CH617202A5 (it)	1980-05-14
CH654010A5 (de)	1986-01-31	Zwischenprodukte zur verwendung bei der herstellung von cephalosporin-antibiotika.
EP0126859B1 (en)	1987-08-19	Intermediate compounds for preparing cephem compounds and processes for their preparation
JPS5824589A (ja)	1983-02-14	生化学的に活性のヒドラゾノセフエム誘導体
SU1249017A1 (ru)	1986-08-07	Цефалоспорины как промежуточные продукты в синтезе цефалоспоринов,обладающих антибактериальными свойствами
US4051129A (en)	1977-09-27	Process for preparing 7-methoxycephalosporin compounds
JPS6259283A (ja)	1987-03-14	セフアロスポリン化合物
EP0023045B1 (en)	1984-04-11	Imidazolecarboxylic acid derivatives of penicillins and cephalosporins
DE2714419C2 (de)	1985-12-05	Cephalosporinderivate, Verfahren zu deren Herstellung und Arzneimittel
JPS6133825B2 (it)	1986-08-04
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