SU974936A3 - Способ получени производных пенама - Google Patents

Способ получени производных пенама Download PDF

Info

Publication number: SU974936A3
Authority: SU; USSR - Soviet Union
Prior art keywords: solution; chloroform; triphenylmethylamino; mol; dimethyl
Prior art date: 1973-10-17

Application number

SU782377452A

Other languages

English (en)

Russian (ru)

Inventor

Эрнест Барт Вэйн

Original Assignee

Пфайзер Инк (Фирма)

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.)

1973-10-17

Filing date

1978-06-28

Publication date

1982-11-15

1978-06-28 Application filed by Пфайзер Инк (Фирма) filed Critical Пфайзер Инк (Фирма)

1982-11-15 Application granted granted Critical

1982-11-15 Publication of SU974936A3 publication Critical patent/SU974936A3/ru

Links

238000000034 method Methods 0.000 title claims description 15
-1 2 - methyl - 1,3,4 - thiadiazolyl Chemical group 0.000 claims abstract description 136
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
239000000203 mixture Substances 0.000 claims abstract description 13
238000006243 chemical reaction Methods 0.000 claims abstract description 12
JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 6
150000001540 azides Chemical class 0.000 claims abstract description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 5
150000008064 anhydrides Chemical class 0.000 claims abstract description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 222
239000000243 solution Substances 0.000 claims description 132
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 60
239000006260 foam Substances 0.000 claims description 56
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 40
238000003756 stirring Methods 0.000 claims description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 25
238000010521 absorption reaction Methods 0.000 claims description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 19
239000011541 reaction mixture Substances 0.000 claims description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 16
238000001816 cooling Methods 0.000 claims description 14
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 14
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 claims description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
239000012267 brine Substances 0.000 claims description 12
239000000047 product Substances 0.000 claims description 12
239000000741 silica gel Substances 0.000 claims description 12
229910002027 silica gel Inorganic materials 0.000 claims description 12
ZMMRLWFGWQVVJD-UHFFFAOYSA-O (n,n-dimethylcarbamimidoyl)-dimethylazanium;azide Chemical compound [N-]=[N+]=[N-].CN(C)C(N)=[N+](C)C ZMMRLWFGWQVVJD-UHFFFAOYSA-O 0.000 claims description 11
150000001408 amides Chemical class 0.000 claims description 11
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 11
235000019341 magnesium sulphate Nutrition 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
239000012043 crude product Substances 0.000 claims description 8
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims description 8
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 7
239000008346 aqueous phase Substances 0.000 claims description 7
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 7
229910052938 sodium sulfate Inorganic materials 0.000 claims description 7
235000011152 sodium sulphate Nutrition 0.000 claims description 7
239000000725 suspension Substances 0.000 claims description 7
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 6
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims description 6
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 5
238000002329 infrared spectrum Methods 0.000 claims description 5
150000003952 β-lactams Chemical class 0.000 claims description 5
RQJDUEKERVZLLU-UHFFFAOYSA-N 4-Hydroxybenzylamine Chemical compound NCC1=CC=C(O)C=C1 RQJDUEKERVZLLU-UHFFFAOYSA-N 0.000 claims description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
239000012346 acetyl chloride Substances 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
238000004587 chromatography analysis Methods 0.000 claims description 4
239000012259 ether extract Substances 0.000 claims description 4
239000002244 precipitate Substances 0.000 claims description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
239000012535 impurity Substances 0.000 claims description 3
239000012071 phase Substances 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
238000001228 spectrum Methods 0.000 claims description 3
150000003536 tetrazoles Chemical class 0.000 claims description 3
YSEAGSCGERFGBL-UHFFFAOYSA-N (5-methylfuran-2-yl)methanamine Chemical compound CC1=CC=C(CN)O1 YSEAGSCGERFGBL-UHFFFAOYSA-N 0.000 claims description 2
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims description 2
XUCBSKXFZJQNKI-SDMSXHDGSA-N C1[C@@H]2N(C1=O)CC(S2)C(=O)N Chemical compound C1[C@@H]2N(C1=O)CC(S2)C(=O)N XUCBSKXFZJQNKI-SDMSXHDGSA-N 0.000 claims description 2
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
241000400611 Eucalyptus deanei Species 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 claims description 2
239000003463 adsorbent Substances 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
235000019270 ammonium chloride Nutrition 0.000 claims description 2
229940000635 beta-alanine Drugs 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
229940061627 chloromethyl methyl ether Drugs 0.000 claims description 2
239000003480 eluent Substances 0.000 claims description 2
VMVZGGPZNHFGKS-UHFFFAOYSA-N ethyl n-(oxomethylidene)carbamate Chemical compound CCOC(=O)N=C=O VMVZGGPZNHFGKS-UHFFFAOYSA-N 0.000 claims description 2
239000000706 filtrate Substances 0.000 claims description 2
XPGRZDJXVKFLHQ-UHFFFAOYSA-N hydron;methyl 3-aminopropanoate;chloride Chemical compound Cl.COC(=O)CCN XPGRZDJXVKFLHQ-UHFFFAOYSA-N 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
239000012074 organic phase Substances 0.000 claims description 2
239000003208 petroleum Substances 0.000 claims description 2
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
239000011780 sodium chloride Substances 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
238000007614 solvation Methods 0.000 claims description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
235000011121 sodium hydroxide Nutrition 0.000 claims 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
239000011259 mixed solution Substances 0.000 claims 2
VHOYFVFTYVTOBQ-SDMSXHDGSA-N (5r)-3-(2h-tetrazol-5-yl)-4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical compound S([C@@H]1CC(N1C1)=O)C1C=1N=NNN=1 VHOYFVFTYVTOBQ-SDMSXHDGSA-N 0.000 claims 1
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 claims 1
ZVELTWGXFULASK-UHFFFAOYSA-N C(CCCC)Cl.[P] Chemical compound C(CCCC)Cl.[P] ZVELTWGXFULASK-UHFFFAOYSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
102000020897 Formins Human genes 0.000 claims 1
108091022623 Formins Proteins 0.000 claims 1
244000215747 Pachyrhizus erosus Species 0.000 claims 1
241000845082 Panama Species 0.000 claims 1
AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical group C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 claims 1
239000000284 extract Substances 0.000 claims 1
JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 claims 1
125000006289 hydroxybenzyl group Chemical group 0.000 claims 1
230000004941 influx Effects 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
239000011777 magnesium Substances 0.000 claims 1
SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
238000001226 reprecipitation Methods 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
125000003831 tetrazolyl group Chemical group 0.000 abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
125000002252 acyl group Chemical group 0.000 abstract 2
125000004423 acyloxy group Chemical group 0.000 abstract 2
125000003282 alkyl amino group Chemical group 0.000 abstract 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
125000002541 furyl group Chemical group 0.000 abstract 2
125000002883 imidazolyl group Chemical group 0.000 abstract 2
125000001786 isothiazolyl group Chemical group 0.000 abstract 2
125000003226 pyrazolyl group Chemical group 0.000 abstract 2
125000004076 pyridyl group Chemical group 0.000 abstract 2
125000000714 pyrimidinyl group Chemical group 0.000 abstract 2
125000000335 thiazolyl group Chemical group 0.000 abstract 2
125000001425 triazolyl group Chemical group 0.000 abstract 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000006710 (C2-C12) alkenyl group Chemical group 0.000 abstract 1
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 abstract 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 1
125000005042 acyloxymethyl group Chemical group 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
239000003242 anti bacterial agent Substances 0.000 abstract 1
125000001246 bromo group Chemical group Br* 0.000 abstract 1
150000001718 carbodiimides Chemical class 0.000 abstract 1
150000001782 cephems Chemical class 0.000 abstract 1
239000012320 chlorinating reagent Substances 0.000 abstract 1
125000004093 cyano group Chemical group *C#N 0.000 abstract 1
125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 abstract 1
239000003937 drug carrier Substances 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
239000006052 feed supplement Substances 0.000 abstract 1
125000001153 fluoro group Chemical group F* 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
125000005633 phthalidyl group Chemical group 0.000 abstract 1
239000002243 precursor Substances 0.000 abstract 1
125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
125000001544 thienyl group Chemical group 0.000 abstract 1
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 3
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
JDOJFXVTTCGROH-UHFFFAOYSA-N (4-phenylmethoxyphenyl)methanamine Chemical compound C1=CC(CN)=CC=C1OCC1=CC=CC=C1 JDOJFXVTTCGROH-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
GMAWQTHVIIUMFA-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenoxy)acetyl]-n-(2-sulfanylethyl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)NCCS)CCN1C(=O)COC1=CC=C(Cl)C=C1Cl GMAWQTHVIIUMFA-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000002959 penams Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000001665 trituration Methods 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- 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
- 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)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (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)
Agricultural Chemicals And Associated Chemicals (AREA)

SU782377452A 1973-10-17 1978-06-28 Способ получени производных пенама SU974936A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US40709773A	1973-10-17	1973-10-17

Publications (1)

Publication Number	Publication Date
SU974936A3 true SU974936A3 (ru)	1982-11-15

Family

ID=23610572

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782377452A SU974936A3 (ru)	1973-10-17	1978-06-28	Способ получени производных пенама

Country Status (22)

Country	Link
JP (3)	JPS50121293A (fr)
AR (2)	AR209283A1 (fr)
BE (1)	BE821164A (fr)
CA (1)	CA1064019A (fr)
DD (1)	DD114266A5 (fr)
DE (1)	DE2449834A1 (fr)
DK (1)	DK542174A (fr)
ES (4)	ES431069A1 (fr)
FR (1)	FR2257298B1 (fr)
GB (4)	GB1481810A (fr)
IE (1)	IE40745B1 (fr)
IL (1)	IL45849A0 (fr)
LU (1)	LU71128A1 (fr)
MW (2)	MW4074A1 (fr)
NL (1)	NL7413643A (fr)
NO (1)	NO743667L (fr)
OA (1)	OA04935A (fr)
PL (1)	PL95747B1 (fr)
SE (2)	SE429342B (fr)
SU (1)	SU974936A3 (fr)
ZA (1)	ZA746544B (fr)
ZM (1)	ZM16174A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20140039202A (ko) *	2011-04-28	2014-04-01	시오노기세야쿠 가부시키가이샤	카테콜 또는 의사 카테콜 구조를 갖는 신규 세펨 화합물
WO2013002215A1 (fr) *	2011-06-27	2013-01-03	塩野義製薬株式会社	Composé de céphème comportant un groupe pyridinium

1974
- 1974-10-07 SE SE7412602A patent/SE429342B/xx unknown
- 1974-10-11 NO NO743667A patent/NO743667L/no unknown
- 1974-10-14 GB GB22873/76A patent/GB1481810A/en not_active Expired
- 1974-10-14 GB GB22872/76A patent/GB1481809A/en not_active Expired
- 1974-10-14 GB GB44350/74A patent/GB1481807A/en not_active Expired
- 1974-10-14 IE IE2113/74A patent/IE40745B1/xx unknown
- 1974-10-14 IL IL45849A patent/IL45849A0/xx unknown
- 1974-10-14 GB GB22871/76A patent/GB1481808A/en not_active Expired
- 1974-10-15 ZA ZA00746544A patent/ZA746544B/xx unknown
- 1974-10-15 MW MW40/74A patent/MW4074A1/xx unknown
- 1974-10-15 MW MW41/74A patent/MW4174A1/xx unknown
- 1974-10-16 DE DE19742449834 patent/DE2449834A1/de not_active Ceased
- 1974-10-16 DD DD181737A patent/DD114266A5/xx unknown
- 1974-10-16 CA CA211,504A patent/CA1064019A/fr not_active Expired
- 1974-10-16 AR AR256116A patent/AR209283A1/es active
- 1974-10-16 ES ES431069A patent/ES431069A1/es not_active Expired
- 1974-10-16 DK DK542174A patent/DK542174A/da not_active Application Discontinuation
- 1974-10-17 BE BE1006235A patent/BE821164A/fr unknown
- 1974-10-17 FR FR7435015A patent/FR2257298B1/fr not_active Expired
- 1974-10-17 NL NL7413643A patent/NL7413643A/xx not_active Application Discontinuation
- 1974-10-17 PL PL1974174893A patent/PL95747B1/pl unknown
- 1974-10-17 JP JP49118743A patent/JPS50121293A/ja active Pending
- 1974-10-17 LU LU71128A patent/LU71128A1/xx unknown
- 1974-10-18 OA OA55326A patent/OA04935A/fr unknown
- 1974-11-04 ZM ZM161/74A patent/ZM16174A1/xx unknown
1975
- 1975-08-18 AR AR260031A patent/AR213726A1/es active
1976
- 1976-08-02 ES ES450398A patent/ES450398A1/es not_active Expired
- 1976-08-02 ES ES450397A patent/ES450397A1/es not_active Expired
- 1976-08-02 ES ES450399A patent/ES450399A1/es not_active Expired
1977
- 1977-09-23 SE SE7710697A patent/SE7710697L/xx not_active Application Discontinuation
1978
- 1978-06-28 SU SU782377452A patent/SU974936A3/ru active
1982
- 1982-01-20 JP JP57007361A patent/JPS5822480B2/ja not_active Expired
1983
- 1983-01-17 JP JP58005766A patent/JPS58131988A/ja active Pending

Also Published As

Publication number	Publication date
IE40745L (en)	1975-04-17
PL95747B1 (pl)	1977-11-30
ZA746544B (en)	1975-10-29
JPS57145882A (en)	1982-09-09
OA04935A (fr)	1980-10-31
SE429342B (sv)	1983-08-29
DK542174A (fr)	1975-06-16
AR213726A1 (es)	1979-03-15
ES450397A1 (es)	1977-08-16
JPS50121293A (fr)	1975-09-23
GB1481809A (en)	1977-08-03
IE40745B1 (en)	1979-08-15
JPS58131988A (ja)	1983-08-06
GB1481808A (en)	1977-08-03
FR2257298B1 (fr)	1978-06-30
NL7413643A (nl)	1975-04-21
MW4074A1 (en)	1976-01-14
CA1064019A (fr)	1979-10-09
AU7442574A (en)	1976-04-29
NO743667L (fr)	1975-05-12
MW4174A1 (en)	1976-06-09
SE7710697L (sv)	1977-09-23
DD114266A5 (fr)	1975-07-20
FR2257298A1 (fr)	1975-08-08
DE2449834A1 (de)	1975-04-30
ES431069A1 (es)	1977-02-01
SE7412602L (fr)	1975-04-18
AR209283A1 (es)	1977-04-15
LU71128A1 (fr)	1975-06-24
BE821164A (fr)	1975-04-17
GB1481810A (en)	1977-08-03
IL45849A0 (en)	1974-12-31
ES450398A1 (es)	1977-09-01
GB1481807A (en)	1977-08-03
ZM16174A1 (en)	1975-06-23
ES450399A1 (es)	1977-08-16
JPS5822480B2 (ja)	1983-05-09

Publication	Publication Date	Title
EP0005889B1 (fr)	1982-06-16	Procédé de préparation de dérivés de bêta-lactame, les nouveaux dérivés ainsi obtenus et compositions pharmaceutiques les contenant
SE461913B (sv)	1990-04-09	Nya beta-laktamasinhibitor-foereningar vilka aer mellanprodukter vid frammstaellning av antibiotiskt verksamma beta-laktamasfoereningar
DE2751624A1 (de)	1978-06-01	1-carba-2-penem-3-carbonsaeure
DE2355209A1 (de)	1974-05-16	Neue antibiotica
DE3039504A1 (de)	1981-04-30	Derivate von 6 -hydroxyalkylpenicillansaeuren als (beta)-lactamase-inhibitoren, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel
DD270712A5 (de)	1989-08-09	Verfahren zur herstellung von (hydrocarbyl)-3-cephem-derivaten
SK278845B6 (sk)	1998-03-04	D-2-aminoacyl-3-(z)-propenylcefalosporínové derivá
SU1487814A3 (ru)	1989-06-15	СПОСОБ ПОЛУЧЕНИЯ 7-АМИНО-З-[3(4-КАРБАМОИЛ-1-ПИРИДИНИО)-1-ПРОПЕН1-ИЛ]-3-ЦЕФЕМ-4-КАРБОКСИЛАТА ч.
DE2512670A1 (de)	1975-09-25	Verfahren zur herstellung von 7betaacylamino-7alpha-alkoxy-cephalosporinen oder 6beta-acylamino-6alpha-alkoxypenicillinen
DE3345093A1 (de)	1984-06-14	7-carboxymethoxyphenylacetamido-3-cephem-derivate, verfahren zu deren herstellung und antibakterielle arzneimittel, welche diese enthalten
DE2461526A1 (de)	1975-07-10	Penicilline, verfahren zu ihrer herstellung und arzneimittel
DE2730377A1 (de)	1978-01-19	7-beta-(2-oxyimino-2-arylacetamido)- cephalosporine
JPS6124396B2 (fr)	1986-06-10
DE2740280A1 (de)	1978-03-09	7-acylamino-8-oxo-3-oxa-1-azabicyclo eckige klammer auf 4.2.0 eckige klammer zu octan-2-carbonsaeure-derivate
NO770703L (no)	1977-09-06	Fremgangsm}te for fremstilling av cefalosporiner
DE3008316A1 (de)	1980-09-25	Penicillansaeure-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel
DE2158330A1 (de)	1972-06-08	Cephalosporansäureverbindungen und diese Verbindungen enthaltende Arzneimittel
DE2611270C2 (de)	1982-12-30	Cephalosporin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung
DE69614102T2 (de)	2002-03-21	Pyrazol[1,5-a]pyrimidin derivate
SU727147A3 (ru)	1980-04-05	Способ получени цефалоспоринов
US4051129A (en)	1977-09-27	Process for preparing 7-methoxycephalosporin compounds
DE2747350A1 (de)	1978-04-27	Clavulansaeureanaloge, deren salze und ester und verfahren zu deren herstellung
PL90581B1 (en)	1977-01-31	6-(methyleneamino)-penicillanic acid derivs[FR2073338A1]
US4687769A (en)	1987-08-18	3-(3,3,3-trifluoropropenyl) cephalosporins
CH637135A5 (en)	1983-07-15	Cephalosporin derivatives and a process for their preparation