HRP980026A2 - 1-izothiazolydinone derivatives of azetidine-2-ones, processes for the preparation and use thereof - Google Patents

1-izothiazolydinone derivatives of azetidine-2-ones, processes for the preparation and use thereof

Info

Publication number: HRP980026A2
Authority: HR; Croatia
Prior art keywords: hydrogen; chlorine; compound according; phch2; bromine
Prior art date: 1998-01-20

Application number

HR980026A

Other languages

English (en)

Croatian (hr)

Inventor

J Jure 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.)

1998-01-20

Filing date

1998-01-20

Publication date

1999-10-31

1998-01-20 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

1998-01-20 Priority to HR980026A priority Critical patent/HRP980026A2/hr

1998-12-25 Priority to JP10370885A priority patent/JPH11255767A/ja

1998-12-29 Priority to CA002256096A priority patent/CA2256096A1/en

1999-01-04 Priority to CZ9919A priority patent/CZ1999A3/cs

1999-01-05 Priority to EP99100069A priority patent/EP0930313A1/en

1999-01-15 Priority to HU9900123A priority patent/HUP9900123A3/hu

1999-01-15 Priority to SK59-99A priority patent/SK5999A3/sk

1999-01-19 Priority to NO990226A priority patent/NO990226L/no

1999-01-19 Priority to CN99100959A priority patent/CN1228430A/zh

1999-01-19 Priority to PL99330906A priority patent/PL330906A1/xx

1999-01-20 Priority to BG103103A priority patent/BG63013B1/bg

1999-10-31 Publication of HRP980026A2 publication Critical patent/HRP980026A2/hr

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 10
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 53
239000001257 hydrogen Substances 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 16
-1 2-phenyl-pyrazol-3-yl Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 6
VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 claims description 6
125000005543 phthalimide group Chemical group 0.000 claims description 6
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000000842 isoxazolyl group Chemical group 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
125000003226 pyrazolyl group Chemical group 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
150000003462 sulfoxides Chemical class 0.000 claims description 4
UEFCKYIRXORTFI-UHFFFAOYSA-N 1,2-thiazolidin-3-one Chemical group O=C1CCSN1 UEFCKYIRXORTFI-UHFFFAOYSA-N 0.000 claims description 3
WWCWNTFURYWCHX-UHFFFAOYSA-N 1,2-thiazolidine 1-oxide Chemical class O=S1CCCN1 WWCWNTFURYWCHX-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
150000003952 β-lactams Chemical class 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
230000026030 halogenation Effects 0.000 claims description 2
238000005658 halogenation reaction Methods 0.000 claims description 2
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 23
239000000460 chlorine Substances 0.000 claims 12
229910052801 chlorine Inorganic materials 0.000 claims 12
125000001309 chloro group Chemical group Cl* 0.000 claims 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
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
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
230000000844 anti-bacterial effect Effects 0.000 claims 1
239000000010 aprotic solvent Substances 0.000 claims 1
125000002393 azetidinyl group Chemical group 0.000 claims 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000001984 thiazolidinyl group Chemical group 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000006260 foam Substances 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
101100208721 Mus musculus Usp5 gene Proteins 0.000 description 9
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
229930182555 Penicillin Natural products 0.000 description 4
239000012043 crude product Substances 0.000 description 4
150000002960 penicillins Chemical class 0.000 description 4
230000008707 rearrangement Effects 0.000 description 4
ZUWRNQXDZVFRGF-JQWIXIFHSA-N (4s)-2-benzyl-4-[(2r)-3,3-dibromo-2-chloro-4-oxoazetidin-1-yl]-5,5-dimethyl-1,1-dioxo-1,2-thiazolidin-3-one Chemical compound N1([C@@H]2C(S(N(CC=3C=CC=CC=3)C2=O)(=O)=O)(C)C)[C@H](Cl)C(Br)(Br)C1=O ZUWRNQXDZVFRGF-JQWIXIFHSA-N 0.000 description 3
CLNDZLBRPTYBPL-JQWIXIFHSA-N (4s)-2-benzyl-4-[(2r)-3,3-dibromo-2-chloro-4-oxoazetidin-1-yl]-5,5-dimethyl-1,2-thiazolidin-3-one Chemical compound CC([C@H](C1=O)N2C(C(Br)(Br)[C@H]2Cl)=O)(C)SN1CC1=CC=CC=C1 CLNDZLBRPTYBPL-JQWIXIFHSA-N 0.000 description 3
QSVSNIULCKLLIT-NEXRNZHYSA-N (4s)-2-benzyl-4-[(2r)-3,3-dibromo-2-chloro-4-oxoazetidin-1-yl]-5,5-dimethyl-1-oxo-1,2-thiazolidin-3-one Chemical compound N1([C@@H]2C(S(N(CC=3C=CC=CC=3)C2=O)=O)(C)C)[C@H](Cl)C(Br)(Br)C1=O QSVSNIULCKLLIT-NEXRNZHYSA-N 0.000 description 3
KGHZYCDDAMUAGN-WOPDTQHZSA-N (4s)-2-benzyl-4-[(2r,3s)-3-bromo-2-chloro-4-oxoazetidin-1-yl]-5,5-dimethyl-1,2-thiazolidin-3-one Chemical compound CC([C@H](C1=O)N2C([C@H](Br)[C@H]2Cl)=O)(C)SN1CC1=CC=CC=C1 KGHZYCDDAMUAGN-WOPDTQHZSA-N 0.000 description 3
ZUWRNQXDZVFRGF-CMPLNLGQSA-N (4s)-2-benzyl-4-[(2s)-3,3-dibromo-2-chloro-4-oxoazetidin-1-yl]-5,5-dimethyl-1,1-dioxo-1,2-thiazolidin-3-one Chemical compound N1([C@@H]2C(S(N(CC=3C=CC=CC=3)C2=O)(=O)=O)(C)C)[C@@H](Cl)C(Br)(Br)C1=O ZUWRNQXDZVFRGF-CMPLNLGQSA-N 0.000 description 3
CLNDZLBRPTYBPL-CMPLNLGQSA-N (4s)-2-benzyl-4-[(2s)-3,3-dibromo-2-chloro-4-oxoazetidin-1-yl]-5,5-dimethyl-1,2-thiazolidin-3-one Chemical compound CC([C@H](C1=O)N2C(C(Br)(Br)[C@@H]2Cl)=O)(C)SN1CC1=CC=CC=C1 CLNDZLBRPTYBPL-CMPLNLGQSA-N 0.000 description 3
QSVSNIULCKLLIT-LPLYKUHDSA-N (4s)-2-benzyl-4-[(2s)-3,3-dibromo-2-chloro-4-oxoazetidin-1-yl]-5,5-dimethyl-1-oxo-1,2-thiazolidin-3-one Chemical compound N1([C@@H]2C(S(N(CC=3C=CC=CC=3)C2=O)=O)(C)C)[C@@H](Cl)C(Br)(Br)C1=O QSVSNIULCKLLIT-LPLYKUHDSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000007832 Na2SO4 Substances 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
239000003782 beta lactam antibiotic agent Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate 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$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide Chemical compound C([C@]1(N2C(=O)[C@H](Br)[C@H]2[S@@](=O)C1(C)C)C(N)=O)C1=CC=CC=C1 BYDOGQKHDYKYAS-GTXICJSNSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$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
ZQSDSRULEVCTPN-VYMLMZJJSA-N (4s)-2-benzyl-4-[(2r,3s)-3-bromo-2-chloro-4-oxoazetidin-1-yl]-5,5-dimethyl-1-oxo-1,2-thiazolidin-3-one Chemical compound N1([C@@H]2C(S(N(CC=3C=CC=CC=3)C2=O)=O)(C)C)[C@H](Cl)[C@@H](Br)C1=O ZQSDSRULEVCTPN-VYMLMZJJSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-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 group 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
230000002378 acidificating effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 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
125000003460 beta-lactamyl group Chemical group 0.000 description 1
229940041011 carbapenems Drugs 0.000 description 1
150000003857 carboxamides Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 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
239000010410 layer Substances 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 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
229940049954 penicillin Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910001487 potassium perchlorate Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
229910001488 sodium perchlorate Inorganic materials 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
230000002195 synergetic effect Effects 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

HR980026A 1998-01-20 1998-01-20 1-izothiazolydinone derivatives of azetidine-2-ones, processes for the preparation and use thereof HRP980026A2 (en)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
HR980026A HRP980026A2 (en)	1998-01-20	1998-01-20	1-izothiazolydinone derivatives of azetidine-2-ones, processes for the preparation and use thereof
JP10370885A JPH11255767A (ja)	1998-01-20	1998-12-25	アゼチジン―２―オンの１―イソチアゾリジノン誘導体及びその製造方法
CA002256096A CA2256096A1 (en)	1998-01-20	1998-12-29	1-isothiazolidinone derivatives of azetidine-2-one, processes for the preparation thereof and use thereof
CZ9919A CZ1999A3 (cs)	1998-01-20	1999-01-04	1-isothiazolidinové deriváty azetidin-2-onu, způsoby jejich přípravy a jejich použití
EP99100069A EP0930313A1 (en)	1998-01-20	1999-01-05	1-isothiazolidinone derivatives of azetidine-2-one, process for the preperation thereof and the use thereof
HU9900123A HUP9900123A3 (en)	1998-01-20	1999-01-15	1-isothiazolidinone derivatives of azetidine-2-one, processes for the preparation thereof and use thereof
SK59-99A SK5999A3 (en)	1998-01-20	1999-01-15	1-isothiazolidinone derivatives of azetidine-2-one, process for the preparation thereof and the use thereof
NO990226A NO990226L (no)	1998-01-20	1999-01-19	1-isotiazolidinon-derivater av azetidin-2-on, fremgangsmåter for fremstilling og anvendelse derav
CN99100959A CN1228430A (zh)	1998-01-20	1999-01-19	氮杂环丁烷－2－酮的1－异噻唑烷酮衍生物及其制备方法和用途
PL99330906A PL330906A1 (en)	1998-01-20	1999-01-19	1-isothiazolydinonic derivatives of azetidin-2-one, method of obtaining them and their applications
BG103103A BG63013B1 (bg)	1998-01-20	1999-01-20	1-изотиазолидинонови производни на азетидин-2-он, методи за тяхното получаване и използването им

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HR980026A HRP980026A2 (en)	1998-01-20	1998-01-20	1-izothiazolydinone derivatives of azetidine-2-ones, processes for the preparation and use thereof

Publications (1)

Publication Number	Publication Date
HRP980026A2 true HRP980026A2 (en)	1999-10-31

Family

ID=10946682

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR980026A HRP980026A2 (en)	1998-01-20	1998-01-20	1-izothiazolydinone derivatives of azetidine-2-ones, processes for the preparation and use thereof

Country Status (11)

Country	Link
EP (1)	EP0930313A1 (cs)
JP (1)	JPH11255767A (cs)
CN (1)	CN1228430A (cs)
BG (1)	BG63013B1 (cs)
CA (1)	CA2256096A1 (cs)
CZ (1)	CZ1999A3 (cs)
HR (1)	HRP980026A2 (cs)
HU (1)	HUP9900123A3 (cs)
NO (1)	NO990226L (cs)
PL (1)	PL330906A1 (cs)
SK (1)	SK5999A3 (cs)

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FR2833842B1 (fr) *	2001-12-21	2004-02-13	Aventis Pharma Sa	Compositions pharmaceutiques a base de derives d'azetidine
WO2016054560A1 (en) *	2014-10-02	2016-04-07	Flatley Discovery Lab	Isoxazole compounds and methods for the treatment of cystic fibrosis
CN108658942B (zh) *	2018-04-28	2020-06-30	中南民族大学	一种基于氧代氮杂环丁烷吡唑羧酸酯化合物及其微波水热法合成方法和应用

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HRP960131A2 (en) *	1996-03-21	1998-04-30	Pliva Pharm & Chem Works	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

1998
- 1998-01-20 HR HR980026A patent/HRP980026A2/hr not_active Application Discontinuation
- 1998-12-25 JP JP10370885A patent/JPH11255767A/ja active Pending
- 1998-12-29 CA CA002256096A patent/CA2256096A1/en not_active Abandoned
1999
- 1999-01-04 CZ CZ9919A patent/CZ1999A3/cs unknown
- 1999-01-05 EP EP99100069A patent/EP0930313A1/en not_active Withdrawn
- 1999-01-15 SK SK59-99A patent/SK5999A3/sk unknown
- 1999-01-15 HU HU9900123A patent/HUP9900123A3/hu unknown
- 1999-01-19 NO NO990226A patent/NO990226L/no not_active Application Discontinuation
- 1999-01-19 CN CN99100959A patent/CN1228430A/zh active Pending
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- 1999-01-20 BG BG103103A patent/BG63013B1/bg unknown

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Publication number	Publication date
BG63013B1 (bg)	2001-01-31
NO990226D0 (no)	1999-01-19
SK5999A3 (en)	2000-04-10
CN1228430A (zh)	1999-09-15
NO990226L (no)	1999-07-21
CA2256096A1 (en)	1999-07-20
BG103103A (en)	1999-09-30
PL330906A1 (en)	1999-08-02
EP0930313A1 (en)	1999-07-21
HUP9900123A3 (en)	1999-11-29
HUP9900123A2 (hu)	1999-09-28
HU9900123D0 (en)	1999-03-29
JPH11255767A (ja)	1999-09-21
CZ1999A3 (cs)	1999-08-11

Legal Events

Date	Code	Title
1999-10-31	A1OB	Publication of a patent application
1999-11-05	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2008-02-07	ODBI	Application refused

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