SU1308198A3 - Способ получени 7-амино-3-замещенной метил- @ -цефем-4-карбоновой кислоты или ее кислотно-аддитивных солей - Google Patents
Способ получени 7-амино-3-замещенной метил- @ -цефем-4-карбоновой кислоты или ее кислотно-аддитивных солей Download PDFInfo
- Publication number
- SU1308198A3 SU1308198A3 SU823520352A SU3520352A SU1308198A3 SU 1308198 A3 SU1308198 A3 SU 1308198A3 SU 823520352 A SU823520352 A SU 823520352A SU 3520352 A SU3520352 A SU 3520352A SU 1308198 A3 SU1308198 A3 SU 1308198A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- chj
- chjch
- methyl
- abc
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 14
- 239000000654 additive Substances 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- -1 carbamoyloxy Chemical group 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000003536 tetrazoles Chemical class 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 238000000354 decomposition reaction Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 150000001782 cephems Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 22
- 229940093499 ethyl acetate Drugs 0.000 claims 7
- 235000019439 ethyl acetate Nutrition 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 235000006408 oxalic acid Nutrition 0.000 claims 5
- 239000000047 product Substances 0.000 claims 5
- 229960001866 silicon dioxide Drugs 0.000 claims 5
- 239000002841 Lewis acid Substances 0.000 claims 4
- 150000007517 lewis acids Chemical class 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 238000004440 column chromatography Methods 0.000 claims 2
- 239000012043 crude product Substances 0.000 claims 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 claims 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 1
- 244000298903 Basella rubra Species 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 240000007124 Brassica oleracea Species 0.000 claims 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims 1
- 235000012905 Brassica oleracea var viridis Nutrition 0.000 claims 1
- 101100325856 Caenorhabditis elegans bed-3 gene Proteins 0.000 claims 1
- 101100190847 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PMP3 gene Proteins 0.000 claims 1
- 241000256856 Vespidae Species 0.000 claims 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 claims 1
- DCWRLHBFXAWEKA-UHFFFAOYSA-N [F].OS(O)(=O)=O Chemical compound [F].OS(O)(=O)=O DCWRLHBFXAWEKA-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 claims 1
- 229940089960 chloroacetate Drugs 0.000 claims 1
- 229960005215 dichloroacetic acid Drugs 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- YWJCOIAVEXSQGJ-HNHGDDPOSA-N (6R)-4-methyl-4-(5-methyltetrazol-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1=NN=NN1C1(S[C@H]2N(C(=C1)C(=O)O)C(C2)=O)C YWJCOIAVEXSQGJ-HNHGDDPOSA-N 0.000 description 1
- FZDRVLJSDYQRPO-HWZXHQHMSA-N (6r)-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C)S[C@@H]2CC(=O)N21 FZDRVLJSDYQRPO-HWZXHQHMSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- XZGLNCKSNVGDNX-UHFFFAOYSA-N 5-methyl-2h-tetrazole Chemical compound CC=1N=NNN=1 XZGLNCKSNVGDNX-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07D501/14—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
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
-
- 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
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
-
- 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
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/48—Methylene radicals, substituted by hetero rings
- C07D501/56—Methylene radicals, substituted by hetero rings with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55132253A JPS5758689A (en) | 1980-09-25 | 1980-09-25 | Novel preparation of 7-substituted or unsubstituted amino-3-substituted methylcephem carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1308198A3 true SU1308198A3 (ru) | 1987-04-30 |
Family
ID=15076944
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823520352A SU1308198A3 (ru) | 1980-09-25 | 1982-12-09 | Способ получени 7-амино-3-замещенной метил- @ -цефем-4-карбоновой кислоты или ее кислотно-аддитивных солей |
| SU823521951A SU1318144A3 (ru) | 1980-09-25 | 1982-12-09 | Способ получени производных цефалоспорина или их солей |
| SU833635254A SU1350166A1 (ru) | 1980-09-25 | 1983-08-24 | 7-Амино-3-замещенный метил- @ -цефем-4-карбонова кислота в качестве промежуточных продуктов в синтезе 7-ациламидоцефалоспоринов,про вл ющих антибактериальные свойства |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823521951A SU1318144A3 (ru) | 1980-09-25 | 1982-12-09 | Способ получени производных цефалоспорина или их солей |
| SU833635254A SU1350166A1 (ru) | 1980-09-25 | 1983-08-24 | 7-Амино-3-замещенный метил- @ -цефем-4-карбонова кислота в качестве промежуточных продуктов в синтезе 7-ациламидоцефалоспоринов,про вл ющих антибактериальные свойства |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5758689A (cg-RX-API-DMAC7.html) |
| AU (2) | AU558669B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE890499A (cg-RX-API-DMAC7.html) |
| CS (1) | CS236493B2 (cg-RX-API-DMAC7.html) |
| GB (2) | GB8333402D0 (cg-RX-API-DMAC7.html) |
| HU (1) | HU188021B (cg-RX-API-DMAC7.html) |
| MX (1) | MX9046A (cg-RX-API-DMAC7.html) |
| PL (1) | PL137674B1 (cg-RX-API-DMAC7.html) |
| SU (3) | SU1308198A3 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA816576B (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4847373A (en) * | 1987-02-26 | 1989-07-11 | Bristol-Myers Company | Production of 3-allyl- and 3-butenyl-3-cephems |
| JPH0390112U (cg-RX-API-DMAC7.html) * | 1989-12-29 | 1991-09-13 |
-
1980
- 1980-09-25 JP JP55132253A patent/JPS5758689A/ja active Granted
-
1981
- 1981-09-22 ZA ZA816576A patent/ZA816576B/xx unknown
- 1981-09-23 PL PL1981238228A patent/PL137674B1/pl unknown
- 1981-09-24 HU HU831798A patent/HU188021B/hu unknown
- 1981-09-25 BE BE0/206067A patent/BE890499A/fr not_active IP Right Cessation
-
1982
- 1982-10-22 CS CS827531A patent/CS236493B2/cs unknown
- 1982-12-09 SU SU823520352A patent/SU1308198A3/ru active
- 1982-12-09 SU SU823521951A patent/SU1318144A3/ru active
-
1983
- 1983-08-24 SU SU833635254A patent/SU1350166A1/ru active
- 1983-12-15 GB GB838333402A patent/GB8333402D0/en active Pending
- 1983-12-15 GB GB838333401A patent/GB8333401D0/en active Pending
-
1985
- 1985-11-13 AU AU49863/85A patent/AU558669B2/en not_active Expired
- 1985-11-13 AU AU49860/85A patent/AU558586B2/en not_active Expired
-
1986
- 1986-03-19 MX MX904686A patent/MX9046A/es unknown
Non-Patent Citations (1)
| Title |
|---|
| Патент СССР № 953983, кл. С 07 D 501/36, 1978. * |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA816576B (en) | 1982-09-29 |
| AU558669B2 (en) | 1987-02-05 |
| GB8333402D0 (en) | 1984-01-25 |
| BE890499A (fr) | 1982-03-25 |
| AU558586B2 (en) | 1987-02-05 |
| JPS5758689A (en) | 1982-04-08 |
| JPS6210512B2 (cg-RX-API-DMAC7.html) | 1987-03-06 |
| SU1350166A1 (ru) | 1987-11-07 |
| MX9046A (es) | 1994-02-28 |
| HU188021B (en) | 1986-03-28 |
| GB8333401D0 (en) | 1984-01-25 |
| PL137674B1 (en) | 1986-07-31 |
| AU4986085A (en) | 1986-03-20 |
| CS236493B2 (en) | 1985-05-15 |
| PL238228A1 (en) | 1983-05-23 |
| AU4986385A (en) | 1986-03-20 |
| SU1318144A3 (ru) | 1987-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MC1921A1 (fr) | Derives acyles | |
| FR2511377A1 (fr) | Nouvelles cephalosporines, et leurs sels | |
| HU183230B (en) | Process for producing syn-7-square bracket-2-bracket-2-amino-4-thiazolyl-bracket closed-2-methoxy-imino-square bracket closed-acetamido-3-acetoxy-methyl-3-cepheme-4-carboxylic acid solvates | |
| CA1060432A (en) | 7 .alpha. METHOXYCEPHALOSPORIN DERIVATIVES | |
| DE69214784T2 (de) | Verfahren zur herstellung von cephalosporinzwischenverbindungen | |
| US3932393A (en) | 3-Methylenecephalosporins and process for production thereof | |
| US4048311A (en) | 7-Acyl-3-(sulfonic acid and sulfamoyl substituted tetrazolyl thiomethyl)cephalosporins | |
| FR2538391A1 (fr) | Fluoromethylthiooxacephalosporines et compositions anti-bacteriennes les renfermant | |
| SU1308198A3 (ru) | Способ получени 7-амино-3-замещенной метил- @ -цефем-4-карбоновой кислоты или ее кислотно-аддитивных солей | |
| US3954745A (en) | Process for preparing cefazolin | |
| KR20020068518A (ko) | 페니실린 결정 및 그 제조 방법 | |
| SU454741A3 (ru) | Способ получени сульфоксидов пенициллина | |
| EP0018546B1 (en) | Process for the production of phenylglycyl chloride hydrochlorides | |
| JPS6133833B2 (cg-RX-API-DMAC7.html) | ||
| EP0047014B1 (en) | Novel thioesters and process for the preparation of the same | |
| US3663563A (en) | Esters of 6-aminopenicillanic acid | |
| JPS596308B2 (ja) | テトラゾ−ルチオ−ル誘導体 | |
| US4126745A (en) | 7-Methoxycephalosporin derivatives | |
| JPS6123198B2 (cg-RX-API-DMAC7.html) | ||
| DE2264753C3 (de) | Penicillansäureverbindungen und Verfahren zu deren Herstellung | |
| DE2810803C2 (de) | Verfahren zur Herstellung von Cephalosporinestern | |
| SU543353A3 (ru) | Способ получени производных 7-монохлорацетамидо-3-дезацетоксицефалоспорановой кислоты | |
| JPH0613528B2 (ja) | セフエム化合物のメトキシ化法 | |
| JP2661810B2 (ja) | ７−アミノ−３−クロロメチル−３−セフェム誘導体の製法 | |
| KR790001503B1 (ko) | △3-세팔로스포린 에스테르의 제조방법 |