SK33397A3 - 4-thia-1-azabicyclo £3,2,0| heptane-3-imino-2-isopropylidene-7- -oxo-analogues of beta-lactames, preparation method thereof and their use - Google Patents

4-thia-1-azabicyclo £3,2,0| heptane-3-imino-2-isopropylidene-7- -oxo-analogues of beta-lactames, preparation method thereof and their use Download PDF

Info

Publication number: SK33397A3
Authority: SK; Slovakia
Prior art keywords: thia; hydrogen; heptane; azabicyclo; beta
Prior art date: 1996-03-21

Application number

SK333-97A

Other languages

English (en)

Slovak (sk)

Inventor

Jure J Herak

Original Assignee

Pliva Pharm & Chem Works

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.)

1996-03-21

Filing date

1997-03-14

Publication date

1997-10-08

1997-03-14 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

1997-10-08 Publication of SK33397A3 publication Critical patent/SK33397A3/sk

Links

238000002360 preparation method Methods 0.000 title claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
239000001257 hydrogen Substances 0.000 claims abstract description 33
150000002431 hydrogen Chemical class 0.000 claims abstract description 20
229910052736 halogen Inorganic materials 0.000 claims abstract description 17
150000002367 halogens Chemical class 0.000 claims abstract description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
239000000543 intermediate Substances 0.000 claims abstract description 6
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims abstract description 6
150000003952 β-lactams Chemical class 0.000 claims description 19
-1 3,4-dimethyl isoxazol-5-yl Chemical group 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 6
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 claims description 4
239000003960 organic solvent Substances 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
230000002195 synergetic effect Effects 0.000 claims description 3
125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
229910052801 chlorine Inorganic materials 0.000 claims 2
239000000460 chlorine Substances 0.000 claims 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
230000000845 anti-microbial effect Effects 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
LNIYKUHGYBVGLW-UHFFFAOYSA-N triethyl phosphite;triphenylphosphane Chemical compound CCOP(OCC)OCC.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 LNIYKUHGYBVGLW-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 11
239000013543 active substance Substances 0.000 abstract 1
238000011203 antimicrobial therapy Methods 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
230000008707 rearrangement Effects 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 6
239000012044 organic layer Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
MXIKYXJYNPMBMM-XTAIUZINSA-N (2s,4r,5r)-2-benzyl-6,6-dibromo-3,3-dimethyl-4,7-dioxo-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide Chemical compound C([C@]1(N2[C@@H](C(C2=O)(Br)Br)[S@](=O)C1(C)C)C(N)=O)C1=CC=CC=C1 MXIKYXJYNPMBMM-XTAIUZINSA-N 0.000 description 4
VJWKKIXBFNJUTJ-XHDPSFHLSA-N (5r,6s)-3-benzylimino-6-bromo-2-propan-2-ylidene-4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical compound S([C@H]1N(C([C@@H]1Br)=O)C1=C(C)C)C1=NCC1=CC=CC=C1 VJWKKIXBFNJUTJ-XHDPSFHLSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229930182555 Penicillin Natural products 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000003782 beta lactam antibiotic agent Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002132 β-lactam antibiotic Substances 0.000 description 4
229940124586 β-lactam antibiotics Drugs 0.000 description 4
BYDOGQKHDYKYAS-GTXICJSNSA-N (2s,4s,5r,6s)-2-benzyl-6-bromo-3,3-dimethyl-4,7-dioxo-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide Chemical compound C([C@]1(N2C(=O)[C@H](Br)[C@H]2[S@@](=O)C1(C)C)C(N)=O)C1=CC=CC=C1 BYDOGQKHDYKYAS-GTXICJSNSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000002960 penicillins Chemical class 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
RXSDPSQQCKMNRT-XLXLTHPISA-N (2S,4R,5R,6S)-N-benzyl-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide Chemical compound O=C([C@H]1C([S@]([C@H]2N1C([C@@H]2Br)=O)=O)(C)C)NCC1=CC=CC=C1 RXSDPSQQCKMNRT-XLXLTHPISA-N 0.000 description 2
QVPZWLBJIFOUQS-CYBMUJFWSA-N (5r)-3-benzylimino-2-propan-2-ylidene-4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical compound S([C@H]1N(C(C1)=O)C1=C(C)C)C1=NCC1=CC=CC=C1 QVPZWLBJIFOUQS-CYBMUJFWSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000003018 phosphorus compounds Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
OLAGSZKFDCBODI-BHVCSQLQSA-N (2S,4R,5R)-N-benzyl-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide Chemical compound O=C([C@H]1C([S@]([C@H]2N1C(C2)=O)=O)(C)C)NCC1=CC=CC=C1 OLAGSZKFDCBODI-BHVCSQLQSA-N 0.000 description 1
FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
YGOAWQXJVXSSGU-UHFFFAOYSA-N 4-oxo-4$l^{4}-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical compound C1CS(=O)C2N1C(=O)C2 YGOAWQXJVXSSGU-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
206010034432 Performance fear Diseases 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
229960000723 ampicillin Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000003857 carboxamides Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam group Chemical group S1CCN2[C@H]1CC2=O WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 1
HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
239000008096 xylene Substances 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

Landscapes

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

SK333-97A 1996-03-21 1997-03-14 4-thia-1-azabicyclo £3,2,0| heptane-3-imino-2-isopropylidene-7- -oxo-analogues of beta-lactames, preparation method thereof and their use SK33397A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HR960131A HRP960131A2 (en)	1996-03-21	1996-03-21	4-thia-1-azabicyclo(3.2.0)heptane-3-imino-2-isopropylidene-7-oxo analogons of beta-lactams, processes for their preparation and use thereof

Publications (1)

Publication Number	Publication Date
SK33397A3 true SK33397A3 (en)	1997-10-08

Family

ID=10946374

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK333-97A SK33397A3 (en)	1996-03-21	1997-03-14	4-thia-1-azabicyclo £3,2,0\| heptane-3-imino-2-isopropylidene-7- -oxo-analogues of beta-lactames, preparation method thereof and their use

Country Status (13)

Country	Link
US (1)	US5856475A (bs)
EP (1)	EP0796857A1 (bs)
JP (1)	JPH107678A (bs)
CN (1)	CN1171403A (bs)
BA (1)	BA96175A (bs)
BG (1)	BG62654B1 (bs)
CA (1)	CA2199859A1 (bs)
CZ (1)	CZ83597A3 (bs)
HR (1)	HRP960131A2 (bs)
HU (1)	HUP9700628A3 (bs)
PL (1)	PL319024A1 (bs)
SI (1)	SI9700067A (bs)
SK (1)	SK33397A3 (bs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HRP980026A2 (en) *	1998-01-20	1999-10-31	Pliva Pharm & Chem Works	1-izothiazolydinone derivatives of azetidine-2-ones, processes for the preparation and use thereof
JP7344846B2 (ja)	2020-06-23	2023-09-14	株式会社アマダ	レーザ加工システム及び加工パレットへの液体塗布方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3879408A (en) *	1972-09-08	1975-04-22	American Home Prod	Process for preparing anhydropenicillins

1996
- 1996-03-21 HR HR960131A patent/HRP960131A2/hr not_active Application Discontinuation
1997
- 1997-03-12 CA CA002199859A patent/CA2199859A1/en not_active Abandoned
- 1997-03-14 EP EP97104391A patent/EP0796857A1/en not_active Withdrawn
- 1997-03-14 SK SK333-97A patent/SK33397A3/sk unknown
- 1997-03-14 JP JP9061299A patent/JPH107678A/ja active Pending
- 1997-03-18 PL PL97319024A patent/PL319024A1/xx unknown
- 1997-03-19 CZ CZ97835A patent/CZ83597A3/cs unknown
- 1997-03-20 CN CN97109644A patent/CN1171403A/zh active Pending
- 1997-03-21 HU HU9700628A patent/HUP9700628A3/hu unknown
- 1997-03-21 US US08/828,267 patent/US5856475A/en not_active Expired - Fee Related
- 1997-03-21 SI SI9700067A patent/SI9700067A/sl unknown
- 1997-03-21 BG BG101346A patent/BG62654B1/bg unknown
- 1997-05-03 BA BA960175A patent/BA96175A/bs unknown

Also Published As

Publication number	Publication date
JPH107678A (ja)	1998-01-13
SI9700067A (en)	1997-10-31
BG62654B1 (bg)	2000-04-28
HRP960131A2 (en)	1998-04-30
BA96175A (bs)	2000-11-06
HU9700628D0 (en)	1997-05-28
HUP9700628A2 (en)	1997-11-28
HUP9700628A3 (en)	1998-01-28
BG101346A (en)	1998-03-31
PL319024A1 (en)	1997-09-29
CA2199859A1 (en)	1997-09-21
US5856475A (en)	1999-01-05
EP0796857A1 (en)	1997-09-24
CN1171403A (zh)	1998-01-28
CZ83597A3 (en)	1997-10-15

Publication	Publication Date	Title
EP0592677A1 (en)	1994-04-20	Beta-LACTAM COMPOUND AND CEPHEM COMPOUND, AND PRODUCTION THEREOF
CS219291B2 (en)	1983-03-25	Method of making the new derivatives of the 6 beta-hydroxyalcylpeniciline acid
MC1921A1 (fr)	1989-04-06	Derives acyles
JPH0196181A (ja)	1989-04-14	２−オキソ−１−［［（置換スルホニル）アミノ］カルボニル］アゼチジン類
EP0966471A1 (en)	1999-12-29	2-beta-substituted-6-alkylidene penicillanic acid derivatives as beta-lactamase inhibitors
US20080009634A1 (en)	2008-01-10	Process for synthesizing beta-lactamase inhibitor intermediates
SK33397A3 (en)	1997-10-08	4-thia-1-azabicyclo £3,2,0\| heptane-3-imino-2-isopropylidene-7- -oxo-analogues of beta-lactames, preparation method thereof and their use
KR840000865B1 (ko)	1984-06-20	β-락탐-함유 항균제의 제조방법
SE458609B (sv)	1989-04-17	7-acyl-3-karbamoyloxi-3-metyl-cefam-foereningar samt foerfarande foer framstaellning daerav
Huang et al.	2003	Stereospecific synthesis of azeto [2, 1‐d]‐[1, 5] benzothiazepin/diazepin‐1‐ones
JP3742829B2 (ja)	2006-02-08	デアセチルセファロスポラン酸のカルバモイル化方法
NO814372L (no)	1982-06-23	Analogifremgangsmaate for fremstilling av antibakterielle cefalosporinderivater
JPH0516433B2 (bs)	1993-03-04
SK278953B6 (sk)	1998-05-06	4-oxo-azetidín-2-sulfónové kyseliny a ich soli, sp
JP2009525964A (ja)	2009-07-16	６，７−ジヒドロ−５Ｈ−イミダゾ［１，２−ａ］イミダゾール−３−スルホン酸アミドの合成
DE69024114T2 (de)	1996-05-09	Verfahren zur Herstellung von Penemen
DE69622099T2 (de)	2003-02-13	Verfahren zur herstellung eines beta-lactamderivates
EP0930313A1 (en)	1999-07-21	1-isothiazolidinone derivatives of azetidine-2-one, process for the preperation thereof and the use thereof
Stephen	1995	Synthesis and biological activity of new C-6 and C-7 substituted vinyloxyimino-penicillins and-cephalosporins
DE69216126T2 (de)	1997-04-10	Allenyl-Beta-Lactam-Verbindungen und Verfahren zu deren Herstellung
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