SE438330B - Forfarande for framstellning av azetidinoner - Google Patents

Forfarande for framstellning av azetidinoner

Info

Publication number: SE438330B
Authority: SE; Sweden
Prior art keywords: formula; compound; give; iii; azetidinone
Prior art date: 1977-07-05

Application number

SE7807489A

Other languages

English (en)

Swedish (sv)

Other versions

SE7807489L (sv

Inventor

M Foglio

G Franceschi

P Lombardi

C Scarafile

F Arcamone

Original Assignee

Farmaceutici Italia

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.)

1977-07-05

Filing date

1978-07-03

Publication date

1985-04-15

1978-07-03 Application filed by Farmaceutici Italia filed Critical Farmaceutici Italia

1979-01-06 Publication of SE7807489L publication Critical patent/SE7807489L/xx

1985-04-15 Publication of SE438330B publication Critical patent/SE438330B/sv

Links

238000000034 method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 17
-1 α-aminobenzyl Chemical group 0.000 claims description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
239000000741 silica gel Substances 0.000 claims description 4
229910002027 silica gel Inorganic materials 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
150000001266 acyl halides Chemical class 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
238000003776 cleavage reaction Methods 0.000 claims description 2
238000006073 displacement reaction Methods 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
230000007017 scission Effects 0.000 claims description 2
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 2
230000006181 N-acylation Effects 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
238000005978 reductive desulfurization reaction Methods 0.000 claims 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
125000003118 aryl group Chemical group 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000003952 β-lactams Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
150000001539 azetidines Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
XFZHTGSNSUUBOU-UHFFFAOYSA-N methyl 2-(3-bromo-4-methoxyphenyl)-2-[2-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]acetate Chemical compound C=1C=C(OC)C(Br)=CC=1C(C(=O)OC)N(C1=O)CC1NC(=O)CC1=CC=CC=C1 XFZHTGSNSUUBOU-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003548 thiazolidines Chemical class 0.000 description 1
238000011282 treatment Methods 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SE7807489A 1977-07-05 1978-07-03 Forfarande for framstellning av azetidinoner SE438330B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2819377		1977-07-05

Publications (2)

Publication Number	Publication Date
SE7807489L SE7807489L (sv)	1979-01-06
SE438330B true SE438330B (sv)	1985-04-15

Family

ID=10271774

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7807489A SE438330B (sv)	1977-07-05	1978-07-03	Forfarande for framstellning av azetidinoner

Country Status (17)

Country	Link
US (1)	US4230619A (da)
JP (1)	JPS5414962A (da)
AT (1)	AT359190B (da)
AU (1)	AU3766278A (da)
BE (1)	BE868710A (da)
CA (1)	CA1152085A (da)
CH (1)	CH634555A5 (da)
DE (1)	DE2829315A1 (da)
DK (1)	DK300178A (da)
FR (1)	FR2396751A1 (da)
GB (1)	GB2017104B (da)
IE (1)	IE47063B1 (da)
IL (1)	IL55077A0 (da)
NL (1)	NL7806860A (da)
NO (1)	NO149774C (da)
SE (1)	SE438330B (da)
ZA (1)	ZA783812B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL70782A (en) *	1983-02-02	1991-03-10	Univ Notre Dame Du Lac	N-dicarboxymethyl azetidin-2-ones
US4992545A (en) *	1989-09-20	1991-02-12	Eli Lilly And Company	Process for preparing 4-substituted azetidinones
US5106475A (en) *	1989-09-20	1992-04-21	Eli Lilly And Company	Process for preparing 4-substituted azetidinones
US6723727B1 (en) *	1996-12-20	2004-04-20	Hoechst Aktiengesellschaft	Substituted purine derivatives, processes for their preparation, their use, and compositions comprising them

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1368231A (en) *	1970-07-31	1974-09-25	Glaxo Lab Ltd	Thio-substituted azetidinones and thiazolino azetidinones
BE794659A (fr) *	1972-01-28	1973-07-30	Glaxo Lab Ltd	Procede de preparation de composes intermediaires pour l'obtention d'antibiotiques de type beta-lactame
IT1043958B (it) *	1974-05-22	1980-02-29	Farmaceutici Italia	Procedimento per la preparazione di cefalosporine
FR2278335A1 (fr) *	1974-07-04	1976-02-13	Fujisawa Pharmaceutical Co	Derives d'azetidinones et leurs procedes de preparation
JPS5175056A (en) *	1974-12-23	1976-06-29	Fujisawa Pharmaceutical Co	33 chikanazejinonjudotaino seizoho
CH618161A5 (en) *	1974-07-04	1980-07-15	Fujisawa Pharmaceutical Co	Process for the preparation of azetidinone derivatives
FR2335212A2 (fr) *	1974-07-04	1977-07-15	Fujisawa Pharmaceutical Co	Azetidinones et procede pour leur preparation
JPS51127064A (en) *	1975-04-10	1976-11-05	Massachusetts Inst Technology	Novel betaalactam antibiotics and intermediate and preparation thereof
GB1570278A (en) *	1975-10-06	1980-06-25	Fujisawa Pharmaceutical Co	O-substituted-2-azetidinone derivatives and the preparation thereof
US4075219A (en) *	1977-03-31	1978-02-21	Eli Lilly And Company	Epimerization process

1978
- 1978-06-26 NL NL7806860A patent/NL7806860A/xx not_active Application Discontinuation
- 1978-06-30 GB GB7914816A patent/GB2017104B/en not_active Expired
- 1978-06-30 US US05/921,070 patent/US4230619A/en not_active Expired - Lifetime
- 1978-06-30 IE IE1325/78A patent/IE47063B1/en unknown
- 1978-06-30 AU AU37662/78A patent/AU3766278A/en active Pending
- 1978-07-03 ZA ZA00783812A patent/ZA783812B/xx unknown
- 1978-07-03 NO NO782301A patent/NO149774C/no unknown
- 1978-07-03 DK DK783001A patent/DK300178A/da not_active Application Discontinuation
- 1978-07-03 SE SE7807489A patent/SE438330B/sv unknown
- 1978-07-03 AT AT480778A patent/AT359190B/de not_active IP Right Cessation
- 1978-07-04 IL IL55077A patent/IL55077A0/xx unknown
- 1978-07-04 CH CH726278A patent/CH634555A5/de not_active IP Right Cessation
- 1978-07-04 BE BE189050A patent/BE868710A/xx not_active IP Right Cessation
- 1978-07-04 FR FR7819860A patent/FR2396751A1/fr active Granted
- 1978-07-04 JP JP8137878A patent/JPS5414962A/ja active Pending
- 1978-07-04 DE DE19782829315 patent/DE2829315A1/de not_active Withdrawn
- 1978-07-05 CA CA000306800A patent/CA1152085A/en not_active Expired

Also Published As

Publication number	Publication date
NO782301L (no)	1979-01-08
IE781325L (en)	1979-01-05
NO149774C (no)	1984-06-20
NL7806860A (nl)	1979-01-09
GB2017104A (en)	1979-10-03
IE47063B1 (en)	1983-12-14
AU3766278A (en)	1980-01-03
US4230619A (en)	1980-10-28
CH634555A5 (de)	1983-02-15
DK300178A (da)	1979-01-06
ZA783812B (en)	1979-07-25
IL55077A0 (en)	1978-09-29
NO149774B (no)	1984-03-12
FR2396751B1 (da)	1983-05-13
CA1152085A (en)	1983-08-16
ATA480778A (de)	1980-03-15
JPS5414962A (en)	1979-02-03
GB2017104B (en)	1982-01-20
DE2829315A1 (de)	1979-01-25
AT359190B (de)	1980-10-27
BE868710A (fr)	1979-01-04
FR2396751A1 (fr)	1979-02-02
SE7807489L (sv)	1979-01-06

Publication	Publication Date	Title
EP0328000B1 (de)	1995-01-18	Indolocarbazol-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE69526443T2 (de)	2002-12-12	2-silyloxy-tetrahydrothienopyridin, sein salz und verfahren zu seiner herstellung
US4272439A (en)	1981-06-09	6-(Substituted-hydroxymethylene penams)
CA1230333A (en)	1987-12-15	Amidine derivatives of mitomycin a, mitomycin c and porfiromycin having antitumor activity and processes for their production
US4237051A (en)	1980-12-02	Stereospecific production of 6- or 7-carbon-substituted-β-lactams
SE438330B (sv)	1985-04-15	Forfarande for framstellning av azetidinoner
US4060688A (en)	1977-11-29	Cephalosporin intermediates
EP0270076B1 (de)	1991-10-09	Imidazolderivate und ein Verfahren zu deren Herstellung
Crowell et al.	1989	3-Sulfonyl-1-carba-1-dethiacephems
US4316024A (en)	1982-02-16	Dioxo piperazine compounds
US4496484A (en)	1985-01-29	Penicillin derivatives
US4347355A (en)	1982-08-31	Inhibitors of transpeptidase
EP0028936B1 (en)	1984-04-11	4-carbamoylimidazol-5-ol derivatives, their production and pharmaceutical compositions containing them
CH642968A5 (de)	1984-05-15	Cephalosporin-analoge und verfahren zu deren herstellung.
DD285604A5 (de)	1990-12-19	Verfahren zur herstellung von enol-ethern und estern
US4374774A (en)	1983-02-22	Mitomycins
US4665166A (en)	1987-05-12	Process for preparing cephalosporin compounds
US4699981A (en)	1987-10-13	Cephalosporin derivatives
US5241073A (en)	1993-08-31	Process for preparing (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo [1,2-a][1,2,4]triazolium-6-yl)]thio-6-[(R)-1-hydroxyethyl]-1-methyl-carbapenem-3-carboxylate and starting materials thereof
US4228074A (en)	1980-10-14	Azetidinone derivatives
EP0098478B1 (de)	1985-11-06	Verfahren zur Herstellung von 7-Amino-1-dethia-1-oxa-3-hydroymethyl-cephem-4-carbonsäuren
US5498727A (en)	1996-03-12	Preparation of benzindole compounds from naphthalene compounds
Hamamichi et al.	1990	Synthesis of α‐(aminomethylene)‐9‐(methoxymethyl)‐9H‐purine‐6‐acetic acid derivatives
HU180927B (en)	1983-05-30	Process for producing 1k-hydroximino-e-homoe-eburane de rivatives
GB2146996A (en)	1985-05-01	3-azidocephalosporins as intermediates and novel antibacterial agents