NO790628L - Analogifremgangsmaate for fremstilling av farmakologisk aktive penicillinderivater - Google Patents
Analogifremgangsmaate for fremstilling av farmakologisk aktive penicillinderivaterInfo
- Publication number
- NO790628L NO790628L NO790628A NO790628A NO790628L NO 790628 L NO790628 L NO 790628L NO 790628 A NO790628 A NO 790628A NO 790628 A NO790628 A NO 790628A NO 790628 L NO790628 L NO 790628L
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- sodium
- ureido
- mol
- carbon atoms
- Prior art date
Links
- 150000002960 penicillins Chemical class 0.000 title claims description 179
- 238000002360 preparation method Methods 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 18
- 230000000144 pharmacologic effect Effects 0.000 title claims description 3
- 229930182555 Penicillin Natural products 0.000 claims description 189
- 229940049954 penicillin Drugs 0.000 claims description 165
- -1 phenyl- Chemical group 0.000 claims description 151
- 125000004432 carbon atom Chemical group C* 0.000 claims description 113
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 57
- 239000002904 solvent Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 150000003230 pyrimidines Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 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 14
- 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 13
- 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 claims description 13
- AVWRKZWQTYIKIY-UHFFFAOYSA-N ureidocarboxylic acid Natural products NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 633
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 565
- 229940056360 penicillin g Drugs 0.000 description 217
- 159000000000 sodium salts Chemical class 0.000 description 216
- 238000002329 infrared spectrum Methods 0.000 description 209
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 206
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 203
- 239000011734 sodium Substances 0.000 description 169
- 229910052708 sodium Inorganic materials 0.000 description 169
- 239000007795 chemical reaction product Substances 0.000 description 166
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 145
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 134
- 229960004920 amoxicillin trihydrate Drugs 0.000 description 133
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 105
- 239000000243 solution Substances 0.000 description 76
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 67
- 239000000203 mixture Substances 0.000 description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- 238000001816 cooling Methods 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 44
- 229910001868 water Inorganic materials 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 33
- 229960003311 ampicillin trihydrate Drugs 0.000 description 30
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000008346 aqueous phase Substances 0.000 description 25
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical group [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 24
- KLOHDWPABZXLGI-YWUHCJSESA-M ampicillin sodium Chemical compound [Na+].C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C([O-])=O)(C)C)=CC=CC=C1 KLOHDWPABZXLGI-YWUHCJSESA-M 0.000 description 24
- 229960001931 ampicillin sodium Drugs 0.000 description 22
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 21
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 238000012545 processing Methods 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 229960003022 amoxicillin Drugs 0.000 description 12
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 208000015181 infectious disease Diseases 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 241000588724 Escherichia coli Species 0.000 description 10
- 229960002457 epicillin Drugs 0.000 description 10
- 210000002837 heart atrium Anatomy 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 9
- RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical group CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000012265 solid product Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 241000589516 Pseudomonas Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000588748 Klebsiella Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 5
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 5
- 230000007306 turnover Effects 0.000 description 5
- ZHQPCZZUXLSAAB-UHFFFAOYSA-N 2-methylsulfanyl-5-nitro-1h-pyrimidin-6-one Chemical class CSC1=NC=C([N+]([O-])=O)C(O)=N1 ZHQPCZZUXLSAAB-UHFFFAOYSA-N 0.000 description 4
- ODTSVZNFALAYCF-UHFFFAOYSA-N 5-amino-2-anilino-1h-pyrimidin-6-one Chemical compound N1=C(O)C(N)=CN=C1NC1=CC=CC=C1 ODTSVZNFALAYCF-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 229960000723 ampicillin Drugs 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
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- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 3
- SJHPCNCNNSSLPL-UHFFFAOYSA-N 4-(ethoxymethylene)-2-phenyloxazol-5-one Chemical compound O1C(=O)C(=COCC)N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-UHFFFAOYSA-N 0.000 description 3
- QTLUUBYEZOZIHU-UHFFFAOYSA-N 5-amino-2-cyclopropyl-1h-pyrimidin-6-one Chemical compound N1=C(O)C(N)=CN=C1C1CC1 QTLUUBYEZOZIHU-UHFFFAOYSA-N 0.000 description 3
- RGGUVJDYKCOPIW-UHFFFAOYSA-N 5-amino-2-methoxy-1h-pyrimidin-6-one Chemical compound COC1=NC=C(N)C(O)=N1 RGGUVJDYKCOPIW-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000005005 aminopyrimidines Chemical class 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000006884 silylation reaction Methods 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782808153 DE2808153A1 (de) | 1978-02-25 | 1978-02-25 | Neue penicilline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE19782851270 DE2851270A1 (de) | 1978-11-27 | 1978-11-27 | Neue penicilline, ihre salze, verfahren zu ihrer herstellung, ihre verwendung und diese verbindungen enthaltende arzneimittel |
| DE19782851226 DE2851226A1 (de) | 1978-11-27 | 1978-11-27 | Neue penicilline, ihre salze, verfahren zu ihrer herstellung, ihre verwendung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO790628L true NO790628L (no) | 1979-08-28 |
Family
ID=27187467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO790628A NO790628L (no) | 1978-02-25 | 1979-02-23 | Analogifremgangsmaate for fremstilling av farmakologisk aktive penicillinderivater |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4241056A (es) |
| EP (1) | EP0003814B1 (es) |
| JP (1) | JPS6058237B2 (es) |
| AT (1) | AT364459B (es) |
| AU (1) | AU522042B2 (es) |
| CA (1) | CA1132539A (es) |
| DE (1) | DE2961571D1 (es) |
| DK (1) | DK77479A (es) |
| ES (1) | ES477520A1 (es) |
| FI (1) | FI68237C (es) |
| GR (1) | GR66677B (es) |
| HU (1) | HU180997B (es) |
| IE (1) | IE48323B1 (es) |
| IL (1) | IL56731A (es) |
| NO (1) | NO790628L (es) |
| NZ (1) | NZ189754A (es) |
| PT (1) | PT69279A (es) |
| YU (1) | YU44979A (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2910190A1 (de) * | 1979-03-15 | 1980-10-02 | Thomae Gmbh Dr K | Neue penicilline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE2928344A1 (de) * | 1979-07-13 | 1981-02-05 | Thomae Gmbh Dr K | Neue lactame, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3028451A1 (de) * | 1980-07-26 | 1982-04-08 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue lactame, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB2086226A (en) * | 1980-10-15 | 1982-05-12 | Beecham Group Ltd | Compositions containing penicillins |
| DE3039243A1 (de) * | 1980-10-17 | 1982-05-27 | Dr. Karl Thomae Gmbh, 7950 Biberach | Antibiotisch wirksame arzneimittelkombination |
| GR78166B (es) * | 1981-05-04 | 1984-09-26 | Chinoin Gyogyszer Es Vegyeszet | |
| EP0067612A1 (en) * | 1981-06-12 | 1982-12-22 | Beecham Group Plc | Penicillin derivatives |
| EP0067610A1 (en) * | 1981-06-16 | 1982-12-22 | Beecham Group Plc | Penicillins, a process for their preparation and compositions containing them |
| DE3134776A1 (de) * | 1981-09-02 | 1983-03-10 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue 6(alpha)-methoxy-penicilline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0091755A1 (en) * | 1982-04-03 | 1983-10-19 | Beecham Group Plc | Penicillin derivatives, a process for their preparation and compositions containing them |
| US4772704A (en) * | 1983-09-21 | 1988-09-20 | Bristol-Myers Company | 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity |
| US4789063A (en) * | 1986-10-30 | 1988-12-06 | International Container Systems, Inc. | Spacer tray for packaging containers |
| DK158598C (da) * | 1988-07-07 | 1990-11-19 | Pharma Vinci As | Penicillinpraeparat til rektal administration |
| GB8909560D0 (en) * | 1989-04-26 | 1989-06-14 | Smith Kline French Lab | Chemical compounds |
| US5290933A (en) * | 1989-04-26 | 1994-03-01 | Smithkline & French Laboratories Limited | Phenylpyrimidone derivatives |
| GB8909558D0 (en) * | 1989-04-26 | 1989-06-14 | Smith Kline French Lab | Chemical compounds |
| JP2006508997A (ja) * | 2002-11-28 | 2006-03-16 | シエーリング アクチエンゲゼルシャフト | Ｃｈｋ−、Ｐｄｋ−およびＡｋｔ−阻害性ピリミジン、それらの製造および薬剤としての使用 |
| US10335374B2 (en) * | 2014-12-04 | 2019-07-02 | University System of Georgia, Valdosta State University | Tablet composition for anti-tuberculosis antibiotics |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3634405A (en) * | 1969-08-01 | 1972-01-11 | Bristol Myers Co | Synthetic penicillins |
| FR2288521A1 (fr) * | 1974-10-25 | 1976-05-21 | Merck Patent Gmbh | Nouvelles penicillines et procede pour leur preparation |
| DE2450668A1 (de) * | 1974-10-25 | 1976-04-29 | Merck Patent Gmbh | Ureidobenzylpenicilline und verfahren zu ihrer herstellung |
| NZ184434A (en) * | 1976-06-30 | 1979-03-28 | Dainippon Pharmaceutical Co | Penicillins with a substituted p-hydroxy-benzyl side-chain, and injectable pharmaceutical compositions |
| US4038271A (en) * | 1976-11-08 | 1977-07-26 | E. R. Squibb & Sons, Inc. | [[[(2,4-Dioxo-1-imidazolidinyl)amino]-carbonyl]amino]acetylpenicillin derivatives |
-
1979
- 1979-02-07 ES ES477520A patent/ES477520A1/es not_active Expired
- 1979-02-19 EP EP79100468A patent/EP0003814B1/de not_active Expired
- 1979-02-19 DE DE7979100468T patent/DE2961571D1/de not_active Expired
- 1979-02-19 GR GR58406A patent/GR66677B/el unknown
- 1979-02-20 AT AT0128279A patent/AT364459B/de not_active IP Right Cessation
- 1979-02-21 US US06/013,006 patent/US4241056A/en not_active Ceased
- 1979-02-22 YU YU00449/79A patent/YU44979A/xx unknown
- 1979-02-22 DK DK77479A patent/DK77479A/da not_active Application Discontinuation
- 1979-02-23 HU HU79TO1096A patent/HU180997B/hu unknown
- 1979-02-23 NZ NZ189754A patent/NZ189754A/en unknown
- 1979-02-23 IL IL56731A patent/IL56731A/xx unknown
- 1979-02-23 PT PT69279A patent/PT69279A/pt unknown
- 1979-02-23 NO NO790628A patent/NO790628L/no unknown
- 1979-02-23 FI FI790614A patent/FI68237C/fi not_active IP Right Cessation
- 1979-02-23 AU AU44559/79A patent/AU522042B2/en not_active Ceased
- 1979-02-26 CA CA322,301A patent/CA1132539A/en not_active Expired
- 1979-02-26 JP JP54021790A patent/JPS6058237B2/ja not_active Expired
- 1979-08-08 IE IE686/79A patent/IE48323B1/en unknown
-
1982
- 1982-09-21 US US06/420,804 patent/USRE31926E/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54122291A (en) | 1979-09-21 |
| NZ189754A (en) | 1984-10-19 |
| US4241056A (en) | 1980-12-23 |
| GR66677B (es) | 1981-04-08 |
| IE790686L (en) | 1979-08-25 |
| EP0003814A2 (de) | 1979-09-05 |
| PT69279A (de) | 1979-03-01 |
| FI68237C (fi) | 1985-08-12 |
| CA1132539A (en) | 1982-09-28 |
| IE48323B1 (en) | 1984-12-12 |
| FI68237B (fi) | 1985-04-30 |
| EP0003814B1 (de) | 1981-12-16 |
| JPS6058237B2 (ja) | 1985-12-19 |
| ATA128279A (de) | 1981-03-15 |
| USRE31926E (en) | 1985-06-25 |
| IL56731A0 (en) | 1979-05-31 |
| IL56731A (en) | 1982-04-30 |
| AT364459B (de) | 1981-10-27 |
| FI790614A (fi) | 1979-08-26 |
| DE2961571D1 (en) | 1982-02-11 |
| AU4455979A (en) | 1979-09-20 |
| ES477520A1 (es) | 1979-06-01 |
| HU180997B (en) | 1983-05-30 |
| YU44979A (en) | 1983-01-21 |
| DK77479A (da) | 1979-08-26 |
| AU522042B2 (en) | 1982-05-13 |
| EP0003814A3 (en) | 1979-10-17 |
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