DK153324B - Analogifremgangsmaade til fremstilling af o-substituerede 7beta-acylamino-3-cephem-3-ol-4-carboxylsyre-forbindelser eller salte deraf - Google Patents
Analogifremgangsmaade til fremstilling af o-substituerede 7beta-acylamino-3-cephem-3-ol-4-carboxylsyre-forbindelser eller salte deraf Download PDFInfo
- Publication number
- DK153324B DK153324B DK358873AA DK358873A DK153324B DK 153324 B DK153324 B DK 153324B DK 358873A A DK358873A A DK 358873AA DK 358873 A DK358873 A DK 358873A DK 153324 B DK153324 B DK 153324B
- Authority
- DK
- Denmark
- Prior art keywords
- cephem
- carboxylic acid
- acid
- amino
- group
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title claims description 13
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- 239000001257 hydrogen Substances 0.000 claims description 16
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
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- RASPLVISAYEZCJ-UEKVPHQBSA-N (6r,7r)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)OC)C(O)=O)=CC=CC=C1 RASPLVISAYEZCJ-UEKVPHQBSA-N 0.000 claims 2
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- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Substances Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 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
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- HEZHYQDYRPUXNJ-UHFFFAOYSA-L potassium dithionite Chemical compound [K+].[K+].[O-]S(=O)S([O-])=O HEZHYQDYRPUXNJ-UHFFFAOYSA-L 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 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
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005797 stannylation reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 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
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000005866 tritylation reaction Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- 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
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/59—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with hetero atoms directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK12978A DK12978A (da) | 1972-06-29 | 1978-01-11 | 3-substituerede 7beta-amino-3-cephem-4-carboxylsyre-forbindelser |
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH978872A CH587268A5 (en) | 1972-06-29 | 1972-06-29 | Substd carboxylic acid derivs - broad spectrum antibiotics and inters |
| CH978872 | 1972-06-29 | ||
| CH1219572 | 1972-08-17 | ||
| CH1219572 | 1972-08-17 | ||
| CH1872272A CH605987A5 (en) | 1972-12-22 | 1972-12-22 | Substd carboxylic acid derivs |
| CH1872272 | 1972-12-22 | ||
| CH265573 | 1973-02-23 | ||
| CH265573A CH605988A5 (en) | 1973-02-23 | 1973-02-23 | Substd 7-beta-amino ceph-3-em-3-ol 4-carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK153324B true DK153324B (da) | 1988-07-04 |
Family
ID=27428472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK358873AA DK153324B (da) | 1972-06-29 | 1973-06-28 | Analogifremgangsmaade til fremstilling af o-substituerede 7beta-acylamino-3-cephem-3-ol-4-carboxylsyre-forbindelser eller salte deraf |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US4073902A (xx) |
| JP (3) | JPS5933599B2 (xx) |
| AR (6) | AR206201A1 (xx) |
| AT (5) | AT329745B (xx) |
| BE (1) | BE801597A (xx) |
| BG (1) | BG24954A3 (xx) |
| CA (1) | CA1110230A (xx) |
| DD (3) | DD106187A5 (xx) |
| DE (1) | DE2331133C2 (xx) |
| DK (1) | DK153324B (xx) |
| FI (3) | FI59602C (xx) |
| FR (1) | FR2190418B1 (xx) |
| GB (1) | GB1435111A (xx) |
| HK (1) | HK73778A (xx) |
| HU (3) | HU168017B (xx) |
| IE (1) | IE37767B1 (xx) |
| IL (1) | IL42506A (xx) |
| LU (3) | LU67891A1 (xx) |
| MY (1) | MY7900008A (xx) |
| NL (3) | NL7309136A (xx) |
| NO (3) | NO145240C (xx) |
| PH (1) | PH18567A (xx) |
| PL (1) | PL91608B1 (xx) |
| RO (4) | RO73345A (xx) |
| SE (5) | SE417099B (xx) |
| YU (8) | YU39910B (xx) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK153157B (da) * | 1973-02-23 | 1988-06-20 | Lilly Co Eli | Analogifremgangsmaade til fremstilling af 7-alfa-aminoacyl-3-halogen-cephalosporinderivater eller farmaceutisk acceptable syreadditionssalte deraf |
| DK157027B (da) * | 1975-02-20 | 1989-10-30 | Ciba Geigy Ag | Fremgangsmaade til fremstilling af 7beta-amino-3-cephem-3-o1-4-carboxylsyreforbindelser eller salte deraf |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU498131B2 (en) * | 1974-02-26 | 1979-02-15 | Ciba-Geigy Ag | Production of cephems by cyclization |
| US4301278A (en) * | 1974-02-26 | 1981-11-17 | Ciba-Geigy Corporation | Process for the manufacture of enol derivatives |
| US3928334A (en) * | 1974-06-06 | 1975-12-23 | Bristol Myers Co | Process for the production of cefamandole |
| US4045435A (en) * | 1974-10-09 | 1977-08-30 | Eli Lilly And Company | Preparation of cephalosporin ethers |
| 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 |
| CH622802A5 (xx) * | 1975-08-20 | 1981-04-30 | Ciba Geigy Ag | |
| PH17188A (en) * | 1977-03-14 | 1984-06-14 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and their pharmaceutical compositions and method of use |
| US4604386A (en) * | 1984-07-09 | 1986-08-05 | Eli Lilly And Company | 3-(alkynylalkyloxy) cephalosporins |
| IL78634A0 (en) | 1985-04-30 | 1986-08-31 | Lilly Co Eli | 7-substituted bicyclic pyrazolidinones |
| DE3851449T2 (de) * | 1987-02-27 | 1995-03-16 | Banyu Pharma Co Ltd | Cephalosporinderivate, Verfahren zu ihrer Herstellung und antibakterielle Mittel. |
| JP2676763B2 (ja) * | 1987-02-27 | 1997-11-17 | 萬有製薬株式会社 | セファロスポリン誘導体 |
| JPS63255800A (ja) * | 1987-04-14 | 1988-10-24 | 礒井 誠二郎 | 警報装置 |
| AU618029B2 (en) * | 1987-11-02 | 1991-12-12 | Imperial Chemical Industries Plc | Polypeptide compounds |
| GB8813356D0 (en) * | 1988-06-06 | 1988-07-13 | Ici Plc | Polypeptide compounds |
| DK0521827T3 (da) | 1991-07-03 | 1996-11-11 | Ciba Geigy Ag | Farmakologisk virksomme hydrazinderivater og fremgangsmåde til deres fremstilling |
| GB9115203D0 (en) * | 1991-07-15 | 1991-08-28 | Biochemie Gmbh | Improvements in or relating to beta lactam production |
| AU3817300A (en) * | 1999-04-01 | 2000-08-01 | Dsm N.V. | Agglomerates by crystallisation |
| US6627556B1 (en) | 2002-04-24 | 2003-09-30 | Lsi Logic Corporation | Method of chemically altering a silicon surface and associated electrical devices |
| CN102268023B (zh) * | 2011-08-15 | 2013-04-17 | 南京丰融化学技术有限公司 | 头孢类衍生物cxd的晶型 |
| CN115160097B (zh) * | 2022-07-22 | 2024-05-28 | 温州大学 | 一种硫代乙酸还原n-o键合成酰胺的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK157320B (da) * | 1970-06-16 | 1989-12-11 | Merck & Co Inc | Analogifremgangsmaade til fremstilling af 3-carbamoyloxy-methyl-7alfa-methoxy-7beta-(2-thienylacetamido)-3-cephem-4-carboxylsyre eller salte deraf |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1308822A (en) * | 1970-04-14 | 1973-03-07 | Beecham Group Ltd | 4-isopropylidene-3-oxocephams |
| IL37879A (en) * | 1970-10-27 | 1974-12-31 | Ciba Geigy Ag | 3-unsubstituted cephalosporin derivatives,process for their manufacture and compositions containing them |
| US3704297A (en) * | 1971-03-05 | 1972-11-28 | American Home Prod | 7 - (1,4 - cyclohexadienylacylamido)cephalosporanic acids and related compounds |
| US3741962A (en) * | 1971-05-21 | 1973-06-26 | Squibb & Sons Inc | Alpha-thioureidocephalosporanic acid compounds |
| US3846417A (en) * | 1972-06-23 | 1974-11-05 | Squibb & Sons Inc | 1,4-cyclohexadienyl imidazolidinyl cephalosporanic acids and derivatives thereof |
| US3917587A (en) * | 1972-11-28 | 1975-11-04 | Lilly Co Eli | Cephalosporin ethers |
| US3917588A (en) * | 1972-11-28 | 1975-11-04 | Lilly Co Eli | {60 -Aminoacyl cephalosporin ethers |
| US3907786A (en) * | 1973-09-04 | 1975-09-23 | Bristol Myers Co | 7-{8 {60 -(2-aminomethyl-1,4-cyclohexadienyl)acetamido{9 -3-heterocyclic-thiomethyl-3-cephem-4-carboxylic acids and salts |
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1973
- 1973-01-01 AR AR248828A patent/AR206201A1/es active
- 1973-05-30 FI FI1751/73A patent/FI59602C/fi active
- 1973-05-30 FI FI1750/73A patent/FI59601C/fi active
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- 1973-06-14 RO RO7300860064A patent/RO63761A/ro unknown
- 1973-06-14 RO RO7386374A patent/RO64419A/ro unknown
- 1973-06-14 RO RO7375138A patent/RO64226A/ro unknown
- 1973-06-15 IL IL42506A patent/IL42506A/xx unknown
- 1973-06-19 DE DE2331133A patent/DE2331133C2/de not_active Expired
- 1973-06-26 FR FR7323235A patent/FR2190418B1/fr not_active Expired
- 1973-06-27 LU LU67891A patent/LU67891A1/xx unknown
- 1973-06-27 GB GB3053773A patent/GB1435111A/en not_active Expired
- 1973-06-27 LU LU67888A patent/LU67888A1/xx unknown
- 1973-06-27 LU LU67887A patent/LU67887A1/xx unknown
- 1973-06-27 BG BG024001A patent/BG24954A3/xx unknown
- 1973-06-28 AT AT569673A patent/AT329745B/de not_active IP Right Cessation
- 1973-06-28 NO NO2681/73A patent/NO145240C/no unknown
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- 1973-06-28 DD DD171906A patent/DD106187A5/xx unknown
- 1973-06-28 DD DD171903A patent/DD106184A5/xx unknown
- 1973-06-28 AT AT57675*7A patent/AT329762B/de not_active IP Right Cessation
- 1973-06-28 DD DD171905A patent/DD107470A5/xx unknown
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- 1973-06-28 CA CA175,100A patent/CA1110230A/en not_active Expired
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- 1973-06-28 DK DK358873AA patent/DK153324B/da not_active Application Discontinuation
- 1973-06-28 HU HUCI1393A patent/HU167726B/hu unknown
- 1973-06-28 BE BE132845A patent/BE801597A/xx not_active IP Right Cessation
- 1973-06-29 YU YU1793/73A patent/YU39910B/xx unknown
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- 1973-06-29 PL PL1973163719A patent/PL91608B1/pl unknown
- 1973-06-29 AR AR248826A patent/AR212576A1/es active
- 1973-06-29 NL NL7309137A patent/NL7309137A/xx not_active Application Discontinuation
- 1973-06-29 AR AR248827A patent/AR212317A1/es active
- 1973-06-29 JP JP48074355A patent/JPS5933599B2/ja not_active Expired
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- 1973-06-29 YU YU1795/73A patent/YU39911B/xx unknown
- 1973-06-29 JP JP48074354A patent/JPS5933598B2/ja not_active Expired
- 1973-06-29 NL NL7309139A patent/NL7309139A/xx not_active Application Discontinuation
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1975
- 1975-09-30 AR AR264921A patent/AR212028A1/es active
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1976
- 1976-02-13 US US05/657,908 patent/US4073902A/en not_active Expired - Lifetime
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1978
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1979
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1980
- 1980-11-03 YU YU02807/80A patent/YU280780A/xx unknown
- 1980-11-06 YU YU02842/80A patent/YU284280A/xx unknown
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1981
- 1981-09-16 YU YU02236/81A patent/YU223681A/xx unknown
- 1981-09-16 YU YU02238/81A patent/YU223881A/xx unknown
- 1981-09-16 YU YU02237/81A patent/YU223781A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK157320B (da) * | 1970-06-16 | 1989-12-11 | Merck & Co Inc | Analogifremgangsmaade til fremstilling af 3-carbamoyloxy-methyl-7alfa-methoxy-7beta-(2-thienylacetamido)-3-cephem-4-carboxylsyre eller salte deraf |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK153157B (da) * | 1973-02-23 | 1988-06-20 | Lilly Co Eli | Analogifremgangsmaade til fremstilling af 7-alfa-aminoacyl-3-halogen-cephalosporinderivater eller farmaceutisk acceptable syreadditionssalte deraf |
| DK157027B (da) * | 1975-02-20 | 1989-10-30 | Ciba Geigy Ag | Fremgangsmaade til fremstilling af 7beta-amino-3-cephem-3-o1-4-carboxylsyreforbindelser eller salte deraf |
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