HRP960131A2 - 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 - Google Patents

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 Download PDF

Info

Publication number: HRP960131A2
Authority: HR; Croatia
Prior art keywords: hydrogen; compound according; bromine; thia; azabicyclo
Prior art date: 1996-03-21

Application number

HR960131A

Other languages

English (en)

Croatian (hr)

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

1996-03-21

Publication date

1998-04-30

1996-03-21 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

1996-03-21 Priority to HR960131A priority Critical patent/HRP960131A2/hr

1997-03-12 Priority to CA002199859A priority patent/CA2199859A1/en

1997-03-14 Priority to JP9061299A priority patent/JPH107678A/ja

1997-03-14 Priority to SK333-97A priority patent/SK33397A3/sk

1997-03-14 Priority to EP97104391A priority patent/EP0796857A1/en

1997-03-18 Priority to PL97319024A priority patent/PL319024A1/xx

1997-03-19 Priority to CZ97835A priority patent/CZ83597A3/cs

1997-03-20 Priority to CN97109644A priority patent/CN1171403A/zh

1997-03-21 Priority to BG101346A priority patent/BG62654B1/bg

1997-03-21 Priority to HU9700628A priority patent/HUP9700628A3/hu

1997-03-21 Priority to SI9700067A priority patent/SI9700067A/sl

1997-03-21 Priority to US08/828,267 priority patent/US5856475A/en

1997-05-03 Priority to BA960175A priority patent/BA96175A/bs

1998-04-30 Publication of HRP960131A2 publication Critical patent/HRP960131A2/hr

Links

238000002360 preparation method Methods 0.000 title claims description 11
150000003952 β-lactams Chemical class 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 20
229910052736 halogen Chemical group 0.000 claims description 14
150000002367 halogens Chemical group 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
-1 5-methyl-isoxazol-3-yl Chemical group 0.000 claims description 7
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 7
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 7
239000000543 intermediate Substances 0.000 claims description 4
150000003018 phosphorus compounds Chemical class 0.000 claims description 4
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical group C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 2
230000002195 synergetic effect Effects 0.000 claims description 2
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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
229910052794 bromium Inorganic materials 0.000 claims 8
125000001246 bromo group Chemical group Br* 0.000 claims 8
150000002431 hydrogen Chemical group 0.000 claims 6
229910052801 chlorine Inorganic materials 0.000 claims 3
239000000460 chlorine Substances 0.000 claims 3
125000001309 chloro group Chemical group Cl* 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
239000002253 acid Substances 0.000 claims 1
230000000845 anti-microbial effect Effects 0.000 claims 1
239000000010 aprotic solvent Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000005543 phthalimide group Chemical group 0.000 claims 1
230000000717 retained effect Effects 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
229930182555 Penicillin Natural products 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
230000008707 rearrangement Effects 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000002960 penicillins Chemical class 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
MXIKYXJYNPMBMM-XTAIUZINSA-N (2s,4r,5r)-2-benzyl-6,6-dibromo-3,3-dimethyl-4,7-dioxo-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide Chemical compound C([C@]1(N2[C@@H](C(C2=O)(Br)Br)[S@](=O)C1(C)C)C(N)=O)C1=CC=CC=C1 MXIKYXJYNPMBMM-XTAIUZINSA-N 0.000 description 3
BYDOGQKHDYKYAS-UMDUXBMUSA-N (2s,4r,5r,6s)-2-benzyl-6-bromo-3,3-dimethyl-4,7-dioxo-4$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-UMDUXBMUSA-N 0.000 description 3
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 3
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 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
239000003782 beta lactam antibiotic agent Substances 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
239000000203 mixture Substances 0.000 description 3
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 description 3
239000000047 product Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002132 β-lactam antibiotic Substances 0.000 description 3
229940124586 β-lactam antibiotics Drugs 0.000 description 3
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 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
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 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group 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
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
102220079670 rs759826252 Human genes 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
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 1
YTPQQILLXVWTQL-RKFVTTHHSA-N (2s,4r,5r)-2-benzyl-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[C@H]2[S@](=O)C1(C)C)C(N)=O)C1=CC=CC=C1 YTPQQILLXVWTQL-RKFVTTHHSA-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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 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
239000007864 aqueous solution Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229940041011 carbapenems Drugs 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000005192 partition Methods 0.000 description 1
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam group Chemical group S1CCN2[C@H]1CC2=O WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 1
150000002961 penems Chemical class 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
239000007858 starting material Substances 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
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)

HR960131A 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 HRP960131A2 (en)

Priority Applications (13)

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
CA002199859A CA2199859A1 (en)	1996-03-21	1997-03-12	4-thia-1-azabicyclo/3.2.0/heptane-3-imino-2-isopropylidene-7-oxo analogons of beta-lactams, processes for their preparation and the use thereof
JP9061299A JPH107678A (ja)	1996-03-21	1997-03-14	３−イミノ−２−イソプロピリデン−７−オキソ−４−チア−１−アザビシクロ［３．２．０］ヘプタン化合物及びその製造方法
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
EP97104391A EP0796857A1 (en)	1996-03-21	1997-03-14	4-thia-1-azabicyclo(3.2.0)heptane-3-imino-2-isopropylidene-7-oxo analogons of beta-lactams, processes for their preparation and the use thereof
PL97319024A PL319024A1 (en)	1996-03-21	1997-03-18	4-thia-1-azabicyclo(3.2.0) heptane-3-imino-2-isopropylideno-7-ketoanalgones of beta-lactames, method of obtaining them and their application
CZ97835A CZ83597A3 (en)	1996-03-21	1997-03-19	4-thia-1-azabicyclo(3,2,0(heptane-3-imino-2-isopropyliden-7-oxo derivatives of beta lactams, process of their preparation and use
CN97109644A CN1171403A (zh)	1996-03-21	1997-03-20	β－内酰胺的4－硫杂－1－氮杂双环[3.3.0]庚烷－3－亚氨基－2－异亚丙基－7－氧代类似物、它们的制备方法及应用
BG101346A BG62654B1 (bg)	1996-03-21	1997-03-21	4-тиа-1-азабицикло[3.2.0]хептан-3-имино-2-изопропилиден-7-оксо, аналозина бета-лактами, методи за тяхното получаване и използването им
HU9700628A HUP9700628A3 (en)	1996-03-21	1997-03-21	4-thia-1-aza-bicyclo[3.2.0]heptan-3-imino-2-izopropiliden-7-oxo-beta-lactame derivatives, process for producing them and use of them
SI9700067A SI9700067A (en)	1996-03-21	1997-03-21	4-thia-1-azabicyclo /3.2.0./heptane-3-imino-2-isopropylidene-7-oxo analogons of beta-lactams, processes for their preparation and the use thereof
US08/828,267 US5856475A (en)	1996-03-21	1997-03-21	4-thia-1-azabicyclo/3.2.0/Heptane-3-Imino-2-isopropylidene-7-oxo-analogons of beta-lactams, processes for their preparation and the use thereof
BA960175A BA96175A (bs)	1996-03-21	1997-05-03	4-Tia-1-azabiciklo¬3.2.0.¾heptan-3- imino-2-izopropiliden-7-okso analogoni beta-laktama postupci priprave i upotreba

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
HRP960131A2 true HRP960131A2 (en)	1998-04-30

Family

ID=10946374

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
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

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
SK33397A3 (en)	1997-10-08
SI9700067A (en)	1997-10-31
BG62654B1 (bg)	2000-04-28
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

Legal Events

Date	Code	Title
1998-04-30	A1OB	Publication of a patent application
1998-05-02	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2007-01-19	ODBI	Application refused

Publication	Publication Date	Title
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JPH0826040B2 (ja)	1996-03-13	ペネム誘導体
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HU197575B (en)	1989-04-28	Process for production of derivatives of i-substituated 2,3-dihydro-pirasole-o /1,2-a/-pirasole