FI67703C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla (4-hydroxi-5-pyrimidinyl)-ureidobensylpenicilliner - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla (4-hydroxi-5-pyrimidinyl)-ureidobensylpenicilliner Download PDFInfo
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- FI67703C FI67703C FI800786A FI800786A FI67703C FI 67703 C FI67703 C FI 67703C FI 800786 A FI800786 A FI 800786A FI 800786 A FI800786 A FI 800786A FI 67703 C FI67703 C FI 67703C
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- Finland
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- group
- hydroxy
- general formula
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- formula
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- 230000000144 pharmacologic effect Effects 0.000 title description 2
- -1 p-hydroxy-phenyl Chemical group 0.000 claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 7
- 150000007530 organic bases Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 229930182555 Penicillin Natural products 0.000 claims description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- 229940049954 penicillin Drugs 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- 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 13
- 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
- AVWRKZWQTYIKIY-UHFFFAOYSA-N ureidocarboxylic acid Natural products NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 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 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003230 pyrimidines Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 239000007853 buffer solution Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 125000004185 ester group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 101100519284 Cercospora nicotianae PDX1 gene Proteins 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 101100277598 Sorghum bicolor DES3 gene Proteins 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 101150073238 sor1 gene Proteins 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 108
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 87
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 159000000000 sodium salts Chemical class 0.000 description 36
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 35
- 238000002329 infrared spectrum Methods 0.000 description 35
- 150000002960 penicillins Chemical class 0.000 description 32
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 29
- 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 27
- 239000007858 starting material Substances 0.000 description 27
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 16
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- 239000002585 base Substances 0.000 description 14
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 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 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000003389 potentiating effect Effects 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 238000004458 analytical method Methods 0.000 description 4
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- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- YSAKDBBGOXMJSW-UHFFFAOYSA-N NC=1C(=NC(=NC1)N(C)C(=O)OCC)O.N1=CN=CC=C1 Chemical compound NC=1C(=NC(=NC1)N(C)C(=O)OCC)O.N1=CN=CC=C1 YSAKDBBGOXMJSW-UHFFFAOYSA-N 0.000 description 1
- FKISQUDKWUHTBU-UHFFFAOYSA-N NC=1C(=NC(=NC1)NCC(C)C#N)O.NC=1C(=NC(=NC1)NCCSC)O.NC=1C(=NC(=NC1)NCCSCC)O Chemical compound NC=1C(=NC(=NC1)NCC(C)C#N)O.NC=1C(=NC(=NC1)NCCSC)O.NC=1C(=NC(=NC1)NCCSCC)O FKISQUDKWUHTBU-UHFFFAOYSA-N 0.000 description 1
- JDSLKONBGXRKRK-UHFFFAOYSA-N NC=1C(=NC(=NC1)NCCCC(=O)N)O.NC=1C(=NC(=NC1)NCCC(=O)C)O.NC=1C(=NC(=NC1)NC1CCC(CC1)O)O Chemical compound NC=1C(=NC(=NC1)NCCCC(=O)N)O.NC=1C(=NC(=NC1)NCCC(=O)C)O.NC=1C(=NC(=NC1)NC1CCC(CC1)O)O JDSLKONBGXRKRK-UHFFFAOYSA-N 0.000 description 1
- IYIOAKYXEZSFJD-UHFFFAOYSA-N NC=1C(=NC(=NC1)NCCNC(C)=O)O.NC=1C(=NC(=NC1)NCCCS(=O)(=O)N)O Chemical compound NC=1C(=NC(=NC1)NCCNC(C)=O)O.NC=1C(=NC(=NC1)NCCCS(=O)(=O)N)O IYIOAKYXEZSFJD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 208000032536 Pseudomonas Infections Diseases 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229960003311 ampicillin trihydrate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 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 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001714 carbamic acid halides Chemical class 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- OUVDSJRBIAHMFT-UHFFFAOYSA-N carbamoylcarbamoyl n-carbamoylcarbamate Chemical compound NC(=O)NC(=O)OC(=O)NC(N)=O OUVDSJRBIAHMFT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000001271 cephalosporin group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 206010014665 endocarditis Diseases 0.000 description 1
- UANIHYVTNQLZIY-UHFFFAOYSA-N ethyl 2-[(5-amino-6-oxo-1H-pyrimidin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC=C(N)C(=O)N1 UANIHYVTNQLZIY-UHFFFAOYSA-N 0.000 description 1
- LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- SIGPWCVHTYIKME-UHFFFAOYSA-N hexamethanol Chemical compound OC.OC.OC.OC.OC.OC SIGPWCVHTYIKME-UHFFFAOYSA-N 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
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical class [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000007981 phosphate-citrate buffer Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012927 reference suspension Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate 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
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
- 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792910190 DE2910190A1 (de) | 1979-03-15 | 1979-03-15 | Neue penicilline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE2910190 | 1979-03-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI800786A FI800786A (fi) | 1980-09-16 |
| FI67703B FI67703B (fi) | 1985-01-31 |
| FI67703C true FI67703C (fi) | 1985-05-10 |
Family
ID=6065482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI800786A FI67703C (fi) | 1979-03-15 | 1980-03-13 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla (4-hydroxi-5-pyrimidinyl)-ureidobensylpenicilliner |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4289775A (fr) |
| EP (1) | EP0016374B1 (fr) |
| JP (1) | JPS55124789A (fr) |
| AT (1) | ATE731T1 (fr) |
| AU (1) | AU536154B2 (fr) |
| CA (1) | CA1138434A (fr) |
| DE (2) | DE2910190A1 (fr) |
| DK (1) | DK110480A (fr) |
| ES (2) | ES8103097A1 (fr) |
| FI (1) | FI67703C (fr) |
| GR (1) | GR74000B (fr) |
| IL (1) | IL59614A (fr) |
| NO (1) | NO800755L (fr) |
| NZ (1) | NZ193127A (fr) |
| PH (1) | PH15821A (fr) |
| PT (1) | PT70956B (fr) |
| ZA (1) | ZA801499B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3042440A1 (de) * | 1980-11-11 | 1982-06-24 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue penicilline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0053693A1 (fr) * | 1980-12-05 | 1982-06-16 | Dr. Karl Thomae GmbH | Pénicillines, leurs sels, procédé de préparation et les compositions pharmaceutiques les contenant |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1040166A (en) * | 1964-07-29 | 1966-08-24 | Beecham Group Ltd | Penicillins |
| US3308023A (en) * | 1964-08-20 | 1967-03-07 | American Home Prod | Therapeutic compositions containing 6-[d-2-(d-2-amino-2-phenylacetamido)-2-phenylacetamido]penicillanic acid |
| FR2288521A1 (fr) * | 1974-10-25 | 1976-05-21 | Merck Patent Gmbh | Nouvelles penicillines et procede pour leur preparation |
| US4038271A (en) * | 1976-11-08 | 1977-07-26 | E. R. Squibb & Sons, Inc. | [[[(2,4-Dioxo-1-imidazolidinyl)amino]-carbonyl]amino]acetylpenicillin derivatives |
| ES477520A1 (es) * | 1978-02-25 | 1979-06-01 | Thomae Gmbh Dr K | Procedimiento para la preparacion de nuevas penicilinas. |
-
1979
- 1979-03-15 DE DE19792910190 patent/DE2910190A1/de not_active Withdrawn
-
1980
- 1980-02-14 ES ES488573A patent/ES8103097A1/es not_active Expired
- 1980-02-20 GR GR61244A patent/GR74000B/el unknown
- 1980-03-05 DE DE8080101107T patent/DE3060217D1/de not_active Expired
- 1980-03-05 AT AT80101107T patent/ATE731T1/de not_active IP Right Cessation
- 1980-03-05 EP EP80101107A patent/EP0016374B1/fr not_active Expired
- 1980-03-13 FI FI800786A patent/FI67703C/fi not_active IP Right Cessation
- 1980-03-13 JP JP3212680A patent/JPS55124789A/ja active Pending
- 1980-03-14 NO NO800755A patent/NO800755L/no unknown
- 1980-03-14 CA CA000347735A patent/CA1138434A/fr not_active Expired
- 1980-03-14 DK DK110480A patent/DK110480A/da not_active Application Discontinuation
- 1980-03-14 ZA ZA00801499A patent/ZA801499B/xx unknown
- 1980-03-14 IL IL59614A patent/IL59614A/xx unknown
- 1980-03-14 NZ NZ193127A patent/NZ193127A/xx unknown
- 1980-03-14 PT PT70956A patent/PT70956B/pt unknown
- 1980-03-14 AU AU56450/80A patent/AU536154B2/en not_active Ceased
- 1980-05-14 US US06/149,839 patent/US4289775A/en not_active Expired - Lifetime
- 1980-05-29 PH PH24084A patent/PH15821A/en unknown
- 1980-10-08 ES ES495716A patent/ES495716A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3060217D1 (en) | 1982-04-01 |
| ES8106529A1 (es) | 1981-06-16 |
| DE2910190A1 (de) | 1980-10-02 |
| ES495716A0 (es) | 1981-06-16 |
| EP0016374A1 (fr) | 1980-10-01 |
| GR74000B (fr) | 1984-06-06 |
| IL59614A0 (en) | 1980-06-30 |
| FI67703B (fi) | 1985-01-31 |
| EP0016374B1 (fr) | 1982-03-03 |
| FI800786A (fi) | 1980-09-16 |
| US4289775A (en) | 1981-09-15 |
| AU5645080A (en) | 1980-09-18 |
| PH15821A (en) | 1983-04-08 |
| CA1138434A (fr) | 1982-12-28 |
| NO800755L (no) | 1980-09-16 |
| IL59614A (en) | 1983-02-23 |
| DK110480A (da) | 1980-09-16 |
| PT70956A (de) | 1980-04-01 |
| ATE731T1 (de) | 1982-03-15 |
| NZ193127A (en) | 1982-09-07 |
| ES488573A0 (es) | 1981-02-16 |
| ES8103097A1 (es) | 1981-02-16 |
| JPS55124789A (en) | 1980-09-26 |
| AU536154B2 (en) | 1984-04-19 |
| PT70956B (de) | 1981-06-25 |
| ZA801499B (en) | 1981-11-25 |
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| FI67703C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla (4-hydroxi-5-pyrimidinyl)-ureidobensylpenicilliner | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DR. KARL THOMAE GESELLSCHAFT MIT |