DD282012A5 - Verfahren zur herstellung von 1-oxapenem-3-carbonsaeure - Google Patents

Verfahren zur herstellung von 1-oxapenem-3-carbonsaeure Download PDF

Info

Publication number: DD282012A5
Authority: DD; German Democratic Republic
Prior art keywords: group; formula; pharmaceutically acceptable; coor; carbon atoms
Prior art date: 1987-07-31

Application number

DD88318411A

Other languages

German (de)

English (en)

Inventor

Hans-Rolf Pfaendler

Wolfram Wendel

Original Assignee

��@��k��

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.)

1987-07-31

Filing date

1988-07-28

Publication date

1990-08-29

1988-07-28 Application filed by ��@��k�� filed Critical ��@��k��

1990-08-29 Publication of DD282012A5 publication Critical patent/DD282012A5/de

Links

239000002253 acid Substances 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims description 37
238000000034 method Methods 0.000 title claims description 35
229910052799 carbon Inorganic materials 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 71
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 20
150000002148 esters Chemical class 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
150000001408 amides Chemical class 0.000 claims abstract description 3
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims abstract 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract 4
-1 Carbamoylthio Chemical group 0.000 claims description 118
125000000217 alkyl group Chemical group 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
239000000460 chlorine Substances 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 17
125000006239 protecting group Chemical group 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
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239000011593 sulfur Substances 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
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125000006413 ring segment Chemical group 0.000 claims description 6
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125000002431 aminoalkoxy group Chemical group 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
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230000002140 halogenating effect Effects 0.000 claims description 2
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239000003242 anti bacterial agent Substances 0.000 abstract description 17
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230000007062 hydrolysis Effects 0.000 abstract description 5
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 57
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238000006243 chemical reaction Methods 0.000 description 55
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238000002329 infrared spectrum Methods 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
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238000002211 ultraviolet spectrum Methods 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000003782 beta lactam antibiotic agent Substances 0.000 description 14
NTSDTZZTKYEUBA-YFKPBYRVSA-N (5S)-7-oxo-6-oxa-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CS[C@@H]2OC(=O)N12 NTSDTZZTKYEUBA-YFKPBYRVSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
229910052708 sodium Inorganic materials 0.000 description 12
239000011734 sodium Substances 0.000 description 12
239000002132 β-lactam antibiotic Substances 0.000 description 12
229940124586 β-lactam antibiotics Drugs 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
239000012442 inert solvent Substances 0.000 description 11
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230000035484 reaction time Effects 0.000 description 11
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229910002027 silica gel Inorganic materials 0.000 description 11
241000894006 Bacteria Species 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
229930182555 Penicillin Natural products 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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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 8
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OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 8
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
239000000126 substance Substances 0.000 description 8
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
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SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 5
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238000011282 treatment Methods 0.000 description 5
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239000000543 intermediate Substances 0.000 description 4
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
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GAWMRGOYPMEYCL-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-(2-tert-butylsulfanyl-3,3-dimethyl-4-oxoazetidin-1-yl)acetate Chemical compound O=C1C(C)(C)C(SC(C)(C)C)N1CC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 GAWMRGOYPMEYCL-UHFFFAOYSA-N 0.000 description 3
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239000003054 catalyst Substances 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 3
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YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
IWPOSDLLFZKGOW-UHFFFAOYSA-N oct-3-enoic acid Chemical compound CCCCC=CCC(O)=O IWPOSDLLFZKGOW-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
239000003973 paint Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
150000002961 penems Chemical class 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 description 1
KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
230000002335 preservative effect Effects 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
229940048914 protamine Drugs 0.000 description 1
239000012264 purified product Substances 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
239000008234 soft water Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
RCZJVHXVCSKDKB-OYKKKHCWSA-N tert-butyl 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-oxoethylidene]amino]oxy-2-methylpropanoate Chemical group N=1C2=CC=CC=C2SC=1SC(=O)\C(=N/OC(C)(C)C(=O)OC(C)(C)C)C1=CSC(N)=N1 RCZJVHXVCSKDKB-OYKKKHCWSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
229940100611 topical cream Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229940100615 topical ointment Drugs 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000001701 trimethoxybenzyl group Chemical group 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000012982 x-ray structure analysis Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD88318411A 1987-07-31 1988-07-28 Verfahren zur herstellung von 1-oxapenem-3-carbonsaeure DD282012A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873725375 DE3725375A1 (de)	1987-07-31	1987-07-31	Stabile oxapenem-3-carbonsaeuren

Publications (1)

Publication Number	Publication Date
DD282012A5 true DD282012A5 (de)	1990-08-29

Family

ID=6332772

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88318411A DD282012A5 (de)	1987-07-31	1988-07-28	Verfahren zur herstellung von 1-oxapenem-3-carbonsaeure

Country Status (20)

Country	Link
US (1)	US5096899A (fr)
EP (1)	EP0301394B1 (fr)
JP (1)	JPH0819135B2 (fr)
KR (1)	KR890002169A (fr)
CN (1)	CN1031533A (fr)
AT (1)	ATE95521T1 (fr)
AU (1)	AU618013B2 (fr)
CA (1)	CA1339450C (fr)
DD (1)	DD282012A5 (fr)
DE (2)	DE3725375A1 (fr)
DK (1)	DK425888A (fr)
ES (1)	ES2060628T3 (fr)
FI (1)	FI883553A (fr)
HU (1)	HU203355B (fr)
IE (1)	IE63026B1 (fr)
IL (1)	IL87254A (fr)
NO (1)	NO883188L (fr)
PH (1)	PH27226A (fr)
PT (1)	PT88118B (fr)
ZA (1)	ZA885571B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3833693A1 (de) *	1988-10-04	1990-04-05	Bayer Ag	Stabile oxapenem-3-carbonsaeuren und ihre verwendung als ss-lactamasehemmer
DE4027928A1 (de) *	1990-09-04	1992-03-05	Bayer Ag	Neue 2-tert.substituierte methyl-oxapenem-3-carbonsaeuren und -ester, verfahren zu ihrer herstellung und ihre verwendung
DE4142423A1 (de) *	1991-12-20	1993-06-24	Pfaendler Hans Rudolf	((ls)-hydroxyalkyl)oxapenem-3-carbonsaeuren und ihre verwendung als betalactamasehemmer
AU9400401A (en) *	2000-10-19	2002-04-29	Amura Ltd	Pharmaceutical compositions containing oxapenem-3-carboxylic acids
EP1199077A1 (fr) *	2000-10-19	2002-04-24	Amura Limited	Compositions pharmaceutiques contenant des acides oxapénème-carboxyliques stabilisées par lyophilisation avec des excipients pharmaceutiques
GB2369358A (en) *	2000-10-19	2002-05-29	Amura Ltd	Oxapenems and pharmaceutical compositions thereof
GB0106428D0 (en) *	2001-03-15	2001-05-02	Amura Ltd	Antibacterial composition
AR039774A1 (es) *	2002-05-01	2005-03-02	Wyeth Corp	6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas
AR039475A1 (es) *	2002-05-01	2005-02-23	Wyeth Corp	6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa
WO2008141764A1 (fr)	2007-05-21	2008-11-27	Hans Rudolf Pfaendler	Composition pharmaceutique active anti-mrsa bactéricide contenant des carbapénèmes
WO2009089380A2 (fr) *	2008-01-08	2009-07-16	The Trustees Of Columbia University In The City Of New York	Procédés pour la régulation médiée par p2ry5 de la pousse de cheveux et des mutants de ceux-ci

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1368236A (en) *	1970-11-03	1974-09-25	Glaxo Lab Ltd	Azetidinone derivatives and their preparation
AU498131B2 (en) *	1974-02-26	1979-02-15	Ciba-Geigy Ag	Production of cephems by cyclization
NZ177159A (en) *	1974-04-20	1978-03-06	Beecham Group Ltd	Clavulanic acid, salts, esters and preparation thereof from streptomyces clavuligerus: pharmaceutical compositions
CA1136132A (fr) *	1975-02-17	1982-11-23	Teruji Tsuji	Cyclisation pour fermer des noyaux cephem et intermediaires ainsi obtenus
US4147864A (en) *	1975-02-20	1979-04-03	Ciba-Geigy Corporation	Process for the manufacture of 7β-amino-3-cephem-3-ol-4 carboxylic acid compounds
US4024152A (en) *	1975-09-19	1977-05-17	Eli Lilly And Company	4-Dithio-3-imido-azetidin-2-ones
GB1529913A (en) *	1976-02-04	1978-10-25	Beecham Group Ltd	Beta-lactam compounds
GB1591438A (en) *	1976-09-09	1981-06-24	Glaxo Lab Ltd	Clavem derivatives
FR2364205A1 (fr) *	1976-09-09	1978-04-07	Glaxo Lab Ltd	Nouvelles betaines monocycliques et leur procede de preparation
GB1593275A (en) *	1976-10-22	1981-07-15	Glaxo Lab Ltd	Clavam derivatives
DK139377A (da) *	1977-03-10	1978-09-11	Beecham Group Ltd	Fremgangsmaade til fremstilling af ethere
US4260627A (en) *	1978-10-24	1981-04-07	Merck & Co., Inc.	1-, 6- And 2-substituted-1-carba-2-penem-3-carboxylic acids
GB2045236A (en) *	1979-03-26	1980-10-29	Hoechst Uk Ltd	Oxapenem derivatives

1987
- 1987-07-31 DE DE19873725375 patent/DE3725375A1/de not_active Withdrawn
1988
- 1988-07-18 NO NO88883188A patent/NO883188L/no unknown
- 1988-07-20 DE DE88111670T patent/DE3884705D1/de not_active Expired - Lifetime
- 1988-07-20 EP EP88111670A patent/EP0301394B1/fr not_active Expired - Lifetime
- 1988-07-20 ES ES88111670T patent/ES2060628T3/es not_active Expired - Lifetime
- 1988-07-20 AT AT88111670T patent/ATE95521T1/de not_active IP Right Cessation
- 1988-07-26 AU AU20040/88A patent/AU618013B2/en not_active Expired
- 1988-07-27 PH PH37299A patent/PH27226A/en unknown
- 1988-07-27 JP JP63185711A patent/JPH0819135B2/ja not_active Expired - Fee Related
- 1988-07-27 PT PT88118A patent/PT88118B/pt not_active IP Right Cessation
- 1988-07-28 IL IL87254A patent/IL87254A/xx not_active IP Right Cessation
- 1988-07-28 DD DD88318411A patent/DD282012A5/de not_active IP Right Cessation
- 1988-07-28 FI FI883553A patent/FI883553A/fi not_active Application Discontinuation
- 1988-07-29 ZA ZA885571A patent/ZA885571B/xx unknown
- 1988-07-29 DK DK425888A patent/DK425888A/da not_active Application Discontinuation
- 1988-07-29 HU HU884042A patent/HU203355B/hu unknown
- 1988-07-29 IE IE234788A patent/IE63026B1/en not_active IP Right Cessation
- 1988-07-29 CA CA000573432A patent/CA1339450C/fr not_active Expired - Fee Related
- 1988-07-30 CN CN88104689A patent/CN1031533A/zh active Pending
- 1988-07-30 KR KR1019880009849A patent/KR890002169A/ko not_active Application Discontinuation
1990
- 1990-08-24 US US07/574,573 patent/US5096899A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DK425888D0 (da)	1988-07-29
US5096899A (en)	1992-03-17
PT88118A (pt)	1989-06-30
PT88118B (pt)	1995-03-01
AU618013B2 (en)	1991-12-12
KR890002169A (ko)	1989-04-08
NO883188L (no)	1989-02-01
DK425888A (da)	1989-02-01
AU2004088A (en)	1989-02-02
HUT48889A (en)	1989-07-28
JPS6442484A (en)	1989-02-14
ATE95521T1 (de)	1993-10-15
EP0301394A1 (fr)	1989-02-01
DE3884705D1 (de)	1993-11-11
IE882347L (en)	1989-01-31
NO883188D0 (no)	1988-07-18
IL87254A0 (en)	1988-12-30
PH27226A (en)	1993-05-04
ES2060628T3 (es)	1994-12-01
JPH0819135B2 (ja)	1996-02-28
DE3725375A1 (de)	1989-02-09
IE63026B1 (en)	1995-03-22
CN1031533A (zh)	1989-03-08
EP0301394B1 (fr)	1993-10-06
ZA885571B (en)	1989-04-26
FI883553A (fi)	1989-02-01
IL87254A (en)	1993-01-31
FI883553A0 (fi)	1988-07-28
CA1339450C (fr)	1997-09-09
HU203355B (en)	1991-07-29

Publication	Publication Date	Title
DD142342A5 (de)	1980-06-18	Verfahren zur herstellung von 6-substituierten thiaazaverbindungen
DE2751624A1 (de)	1978-06-01	1-carba-2-penem-3-carbonsaeure
DD282012A5 (de)	1990-08-29	Verfahren zur herstellung von 1-oxapenem-3-carbonsaeure
EP0247431B1 (fr)	1990-08-01	Antibiotiques du 6-hydroxyméthylcarbapénème substitués, leur procédé de préparation et leur application
EP0362622B1 (fr)	1995-03-29	Utilisation d'acides oxapenem-3-carboxyliques stables pour l'obtention d'un médicament destiné à l'inhibition de beta-lactamase
AT395590B (de)	1993-01-25	2-methoxymethylpenemverbindungen, verfahren zu deren herstellung und sie enthaltende pharmazeutische zusammensetzungen
DD215551A5 (de)	1984-11-14	Verfahren zur herstellung von 6-hydroxyniederalkyl-penem-verbindungen
DE3750842T2 (de)	1995-05-18	Penem-Derivate, ihre Herstellung und Verwendung.
CH640236A5 (en)	1983-12-30	3-(2-Aminoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2 -carboxylic acid and process for its preparation
DE2652679C2 (fr)	1990-03-01
DE2751597A1 (de)	1978-05-24	3-(2-aminoaethylthio)-6-(1-hydroxyaethyl)-7-oxo-1-azabicyclo eckige klammer auf 3.2.0 eckige klammer zu hept-2-en- 2-carbonsaeure
EP0548790B1 (fr)	1996-05-01	Acides (1'S)-hydroxyalkyloxapenem-3-carboxyliques et leur utilisation comme inhibiteurs de la bêta-lactamase
CH661927A5 (de)	1987-08-31	Carbapenem-antibiotika.
DE2336344A1 (de)	1974-03-14	Penicillin- und cephalosporin-rsulfoxide, ihre salze und ester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0268963A1 (fr)	1988-06-01	Antibiotiques du type benzazolylthiocarbapénème
DE3302335A1 (de)	1983-07-28	Ss-lactamverbindungen, ihre herstellung und sie enthaltendes arzneimittel
DE3434504A1 (de)	1985-04-18	Fluoralkylierte carbapenemderivate
EP0201459A1 (fr)	1986-11-12	Dérivés d'acylaminométhyl-pénème, leur préparation et compositions pharmaceutiques les contenant
AT381942B (de)	1986-12-10	Verfahren zur herstellung neuer carbapenem-derivate
AT387574B (de)	1989-02-10	Verfahren zur herstellung neuer carbapenem-derivate
DE3346775A1 (de)	1984-07-05	Oxacephalosporine und verfahren zu ihrer herstellung
DE2820055A1 (de)	1979-11-22	6-(alpha-hydroxyaethyl)-7-oxo-1- azabicyclo eckige klammer auf 3.2.0 eckige klammer zu-hept-2-en-(und heptan)-2-carbonsaeure und deren derivate
EP0082113A1 (fr)	1983-06-22	Dérivés 2-aminobutyl de 2-pénème, procédé de préparation et compositions pharmaceutiques qui les contiennent
CH641459A5 (en)	1984-02-29	3-(2-aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]h ept-2-ene-2-carboxylic acid

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