NL8204089A - Nieuwe van 3-amino 2-oxo-azetidine 1-sulfonzuur afgeleide verbindingen, hun bereiding, hun toepassing als geneesmiddelen, de samenstellingen die ze bevatten en de verkregen nieuwe tussenprodukten. - Google Patents
Nieuwe van 3-amino 2-oxo-azetidine 1-sulfonzuur afgeleide verbindingen, hun bereiding, hun toepassing als geneesmiddelen, de samenstellingen die ze bevatten en de verkregen nieuwe tussenprodukten. Download PDFInfo
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- NL8204089A NL8204089A NL8204089A NL8204089A NL8204089A NL 8204089 A NL8204089 A NL 8204089A NL 8204089 A NL8204089 A NL 8204089A NL 8204089 A NL8204089 A NL 8204089A NL 8204089 A NL8204089 A NL 8204089A
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- 150000001875 compounds Chemical class 0.000 title claims description 211
- 238000002360 preparation method Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 title description 59
- NSRVGDULUQOEBX-UHFFFAOYSA-N 3-amino-2-oxoazetidine-1-sulfonic acid Chemical compound NC1CN(S(O)(=O)=O)C1=O NSRVGDULUQOEBX-UHFFFAOYSA-N 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
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- 125000006239 protecting group Chemical group 0.000 claims description 36
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000003277 amino group Chemical group 0.000 claims description 22
- CDFGMYLBUSYTKQ-UHFFFAOYSA-N 2-oxoazetidine-1-sulfonic acid Chemical compound OS(=O)(=O)N1CCC1=O CDFGMYLBUSYTKQ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
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- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
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- KHUNFTAJVUPPCY-UHFFFAOYSA-N azetidine-1-sulfonic acid Chemical compound OS(=O)(=O)N1CCC1 KHUNFTAJVUPPCY-UHFFFAOYSA-N 0.000 claims 1
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- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 14
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 12
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- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- RCTFHBWTYQOVGJ-UHFFFAOYSA-N chloroform;dichloromethane Chemical compound ClCCl.ClC(Cl)Cl RCTFHBWTYQOVGJ-UHFFFAOYSA-N 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- ZBHDTYQJAQDBIH-UHFFFAOYSA-N fluoroacetyl chloride Chemical compound FCC(Cl)=O ZBHDTYQJAQDBIH-UHFFFAOYSA-N 0.000 description 1
- 238000005242 forging Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- JFLRBGOBOJWPHI-UHFFFAOYSA-N pyridin-1-ium-1-sulfonate Chemical compound [O-]S(=O)(=O)[N+]1=CC=CC=C1 JFLRBGOBOJWPHI-UHFFFAOYSA-N 0.000 description 1
- KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 206010039447 salmonellosis Diseases 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- BLSRNVDCHVKXSO-UHFFFAOYSA-M sodium;2-ethylbutanoate Chemical compound [Na+].CCC(CC)C([O-])=O BLSRNVDCHVKXSO-UHFFFAOYSA-M 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
- C07D205/085—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 nitrogen atom directly attached in position 3
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8119946 | 1981-10-23 | ||
| FR8119946A FR2515182B1 (fr) | 1981-10-23 | 1981-10-23 | Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine 1-sulfamique, leur procede de preparation, leur application comme medicaments et les produits intermediaires necessaires a leur preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8204089A true NL8204089A (nl) | 1983-05-16 |
Family
ID=9263337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8204089A NL8204089A (nl) | 1981-10-23 | 1982-10-22 | Nieuwe van 3-amino 2-oxo-azetidine 1-sulfonzuur afgeleide verbindingen, hun bereiding, hun toepassing als geneesmiddelen, de samenstellingen die ze bevatten en de verkregen nieuwe tussenprodukten. |
Country Status (12)
| Country | Link |
|---|---|
| JP (2) | JPS58135883A (en, 2012) |
| AT (1) | AT382150B (en, 2012) |
| BE (1) | BE894785A (en, 2012) |
| CA (1) | CA1201439A (en, 2012) |
| CH (1) | CH655317A5 (en, 2012) |
| DE (1) | DE3239157C2 (en, 2012) |
| FR (1) | FR2515182B1 (en, 2012) |
| GB (1) | GB2111482B (en, 2012) |
| IT (1) | IT1157233B (en, 2012) |
| LU (1) | LU84434A1 (en, 2012) |
| NL (1) | NL8204089A (en, 2012) |
| SE (2) | SE461655B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982001873A1 (en) * | 1980-12-05 | 1982-06-10 | Takeda Chemical Industries Ltd | 1-sulfo-2-oxoazetidine derivatives and process for their preparation |
| MX7096E (es) * | 1980-12-05 | 1987-06-19 | Takeda Chemical Industries Ltd | Metodo para preparacion de derivados de 2-oxoazetidina |
| US4673739A (en) * | 1980-12-05 | 1987-06-16 | Takeda Chemical Industries, Ltd. | 4-carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production |
| US4675397A (en) * | 1980-12-05 | 1987-06-23 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
| US4572801A (en) * | 1981-04-30 | 1986-02-25 | Takeda Chemical Industries, Ltd. | 4-Carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production |
| FR2558467B2 (fr) * | 1981-10-23 | 1987-03-20 | Roussel Uclaf | Nouveau produit derive de l'acide 3-amino 2-oxo azetidine 1-sulfamique, son procede de preparation, son application comme medicament et un produit intermediaire necessaire a sa preparation |
| US4443374A (en) * | 1982-02-01 | 1984-04-17 | E. R. Squibb & Sons, Inc. | Process for preparing (3S)-3-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]-acetyl]amino]-2-oxo-1-azetidinesulfonic acid, and 4-substituted derivatives |
| JPS59175490A (ja) * | 1983-03-24 | 1984-10-04 | Banyu Pharmaceut Co Ltd | ２−オキソ−１−アゼチジンスルホン酸誘導体 |
| JPS58208288A (ja) * | 1982-05-31 | 1983-12-03 | Banyu Pharmaceut Co Ltd | ２−オキソ−１−アゼチジンスルホン酸誘導体 |
| DE3377061D1 (en) * | 1982-06-03 | 1988-07-21 | Hoffmann La Roche | Process for the preparation of 1-sulfo-2-oxoazetidine derivatives |
| DE3372768D1 (de) * | 1982-06-03 | 1987-09-03 | Hoffmann La Roche | 1-sulfo-2-oxoazetidine derivatives |
| JPS5982359A (ja) * | 1982-11-02 | 1984-05-12 | Kanegafuchi Chem Ind Co Ltd | ４（Ｒ）配位光学活性β−ラクタム化合物の製法 |
| EP0117053A1 (en) * | 1983-02-10 | 1984-08-29 | Ajinomoto Co., Inc. | Azetidinone derivatives |
| JPS59231086A (ja) * | 1983-06-15 | 1984-12-25 | Teikoku Hormone Mfg Co Ltd | ４−メトキシエチル−２−アゼチジノン−１−スルホン酸誘導体 |
| US4501697A (en) * | 1983-06-17 | 1985-02-26 | E. R. Squibb & Sons, Inc. | 4-[[(Amidomethyl)oxy]methyl]-2-oxo-1-azetidinesulfonic acid salts |
| JPS6097978A (ja) * | 1983-10-31 | 1985-05-31 | Otsuka Chem Co Ltd | ３−アシルアミノ−４−メチル−２−アゼチジノン−１−スルホン酸誘導体，その製造方法および該誘導体を含有する薬剤 |
| JPS60202882A (ja) * | 1984-03-27 | 1985-10-14 | Teikoku Hormone Mfg Co Ltd | 新規な２−アゼチジノン−１−スルホン酸誘導体 |
| US4837318A (en) * | 1985-05-09 | 1989-06-06 | The Upjohn Company | Carbonate substituted monobactams as antibiotics |
| JPS62502825A (ja) * | 1985-05-09 | 1987-11-12 | ジ・アップジョン・カンパニ− | 抗生物質としてのカ−ボネ−ト置換モノバクタム |
| DE19642530A1 (de) * | 1996-10-15 | 1998-04-16 | Bayer Ag | Halogenalkoximinoessigsäureamide |
| US6677028B1 (en) | 1999-09-10 | 2004-01-13 | 3M Innovative Properties Company | Retroreflective articles having multilayer films and methods of manufacturing same |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK194776A (da) * | 1975-05-05 | 1976-11-06 | Smithkline Corp | Antibakterielle midler og mellemprodukter dertil |
| US4166816A (en) * | 1975-05-05 | 1979-09-04 | Smithkline Corporation | Methods and intermediates for preparing cis-4-oxoazetidine intermediates |
| FR2361885A1 (fr) * | 1975-09-03 | 1978-03-17 | Smithkline Corp | Analogues de la penicilline, leurs intermediaires et procedes pour leur obtention |
| US4103086A (en) | 1975-10-29 | 1978-07-25 | Smithkline Corporation | 8-Oxo-4-thia-1-azabicyclo (4.2.0)-oct-2-ene derivatives |
| US4085100A (en) * | 1976-11-01 | 1978-04-18 | Smithkline Corporation | Intermediate for dephthaloylation of azetidinone compounds |
| US4144333A (en) * | 1976-11-15 | 1979-03-13 | Smithkline Corporation | Monocyclic beta-lactams with antibacterial activity |
| US4218459A (en) | 1977-12-28 | 1980-08-19 | Merck & Co., Inc. | 6-Amido-1-carba-2-penem-3-carboxylic acid |
| US4218463A (en) | 1977-12-28 | 1980-08-19 | Merck & Co., Inc. | 3-Substituted thio-6-amido-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| EP0005507A1 (de) * | 1978-05-18 | 1979-11-28 | Ciba-Geigy Ag | Fragmentierungsverfahren von 3-(2-Hydroxyimino-acetylamino)-2-oxo-azetidin-Verbindungen und die erhaltenen Verbindungen |
| DE3069587D1 (en) * | 1979-06-08 | 1984-12-13 | Takeda Chemical Industries Ltd | 1-sulpho-2-oxoazetidine derivatives, their production and pharmaceutical compositions thereof |
| NZ205240A (en) * | 1980-02-07 | 1984-07-31 | Squibb & Sons Inc | Sulphonamide derivatives,being starting materials for producing beta-lactams |
| WO1982001873A1 (en) * | 1980-12-05 | 1982-06-10 | Takeda Chemical Industries Ltd | 1-sulfo-2-oxoazetidine derivatives and process for their preparation |
| JPS58189176A (ja) | 1982-04-30 | 1983-11-04 | Takeda Chem Ind Ltd | １−スルホ−２−アゼチジノン誘導体およびその製造法 |
| JPS57131758A (en) * | 1980-12-05 | 1982-08-14 | Takeda Chem Ind Ltd | 1-sulfo-2-oxoazetidine derivative, its preparation and use |
| JPS58210061A (ja) | 1982-05-31 | 1983-12-07 | Takeda Chem Ind Ltd | １−スルホ−２−オキソアゼチジン誘導体、その製造法および用途 |
| DE3274981D1 (en) * | 1981-10-05 | 1987-02-12 | Squibb & Sons Inc | 4-ether derivatives of 2-azetidinone-1-sulfonic acids |
| AU564150B2 (en) * | 1982-04-30 | 1987-08-06 | Takeda Chemical Industries Ltd. | 1-sulfo-2-azetidinone derivatives |
| JPS59175490A (ja) * | 1983-03-24 | 1984-10-04 | Banyu Pharmaceut Co Ltd | ２−オキソ−１−アゼチジンスルホン酸誘導体 |
| HU189290B (en) * | 1982-05-31 | 1986-06-30 | Banyu Pharmaceutical Co Ltd,Jp | Process for preparing new 2-oxo-1-azetidine-sulphonic acid derivatives and pharmaceutically acceptable salts thereof, further pharmaceutical compositions containing such derivatives as active substances |
| JPS58208288A (ja) * | 1982-05-31 | 1983-12-03 | Banyu Pharmaceut Co Ltd | ２−オキソ−１−アゼチジンスルホン酸誘導体 |
-
1981
- 1981-10-23 FR FR8119946A patent/FR2515182B1/fr not_active Expired
-
1982
- 1982-10-15 SE SE8205870A patent/SE461655B/sv not_active IP Right Cessation
- 1982-10-22 CA CA000413983A patent/CA1201439A/fr not_active Expired
- 1982-10-22 LU LU84434A patent/LU84434A1/fr unknown
- 1982-10-22 NL NL8204089A patent/NL8204089A/nl not_active Application Discontinuation
- 1982-10-22 DE DE3239157A patent/DE3239157C2/de not_active Expired - Fee Related
- 1982-10-22 BE BE0/209311A patent/BE894785A/fr not_active IP Right Cessation
- 1982-10-22 CH CH6166/82A patent/CH655317A5/fr not_active IP Right Cessation
- 1982-10-22 JP JP57184814A patent/JPS58135883A/ja active Granted
- 1982-10-22 IT IT49341/82A patent/IT1157233B/it active
- 1982-10-25 GB GB08230366A patent/GB2111482B/en not_active Expired
- 1982-10-25 AT AT0391182A patent/AT382150B/de not_active IP Right Cessation
-
1987
- 1987-06-04 SE SE8702330A patent/SE500849C2/sv unknown
-
1991
- 1991-04-26 JP JP3122828A patent/JPH0730018B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3239157A1 (de) | 1983-05-05 |
| IT8249341A0 (it) | 1982-10-22 |
| JPH04234844A (ja) | 1992-08-24 |
| SE8205870D0 (sv) | 1982-10-15 |
| LU84434A1 (fr) | 1983-06-13 |
| SE461655B (sv) | 1990-03-12 |
| JPH0471073B2 (en, 2012) | 1992-11-12 |
| SE8205870L (sv) | 1983-04-24 |
| GB2111482B (en) | 1985-11-06 |
| JPH0730018B2 (ja) | 1995-04-05 |
| CA1201439A (fr) | 1986-03-04 |
| CH655317A5 (fr) | 1986-04-15 |
| DE3239157C2 (de) | 1994-04-28 |
| FR2515182B1 (fr) | 1986-05-09 |
| FR2515182A1 (fr) | 1983-04-29 |
| ATA391182A (de) | 1986-06-15 |
| IT1157233B (it) | 1987-02-11 |
| JPS58135883A (ja) | 1983-08-12 |
| AT382150B (de) | 1987-01-12 |
| SE500849C2 (sv) | 1994-09-19 |
| SE8702330D0 (sv) | 1987-06-04 |
| BE894785A (fr) | 1983-04-22 |
| SE8702330L (sv) | 1987-06-04 |
| GB2111482A (en) | 1983-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |