NO750788L - - Google Patents

Info

Publication number

NO750788L

NO750788L NO750788A NO750788A NO750788L NO 750788 L NO750788 L NO 750788L NO 750788 A NO750788 A NO 750788A NO 750788 A NO750788 A NO 750788A NO 750788 L NO750788 L NO 750788L

Authority

NO

Norway

Prior art keywords

group

acid

penicillanic acid

penicillin

pharmaceutically acceptable

Prior art date

1971-11-01

Links

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• Global Dossier
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• 238000002360 preparation method Methods 0.000 claims description 38
• 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 34
• 229930182555 Penicillin Natural products 0.000 claims description 30
• 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 20
• -1 pivaloyloxymethyl Chemical group 0.000 claims description 20
• 150000001875 compounds Chemical class 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 238000000034 method Methods 0.000 claims description 15
• 229940049954 penicillin Drugs 0.000 claims description 15
• 229930186147 Cephalosporin Natural products 0.000 claims description 13
• 229940124587 cephalosporin Drugs 0.000 claims description 13
• 150000001780 cephalosporins Chemical class 0.000 claims description 13
• 230000000844 anti-bacterial effect Effects 0.000 claims description 11
• 150000003839 salts Chemical class 0.000 claims description 6
• 230000002195 synergetic effect Effects 0.000 claims description 6
• 125000004185 ester group Chemical group 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 238000001727 in vivo Methods 0.000 claims description 5
• 208000035473 Communicable disease Diseases 0.000 claims description 4
• 150000001768 cations Chemical class 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
• 239000000203 mixture Substances 0.000 claims description 4
• NONJJLVGHLVQQM-JHXYUMNGSA-N phenethicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(C)OC1=CC=CC=C1 NONJJLVGHLVQQM-JHXYUMNGSA-N 0.000 claims description 4
• 229930195708 Penicillin V Natural products 0.000 claims description 3
• 229960000603 cefalotin Drugs 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 235000019371 penicillin G benzathine Nutrition 0.000 claims description 3
• 229940056360 penicillin g Drugs 0.000 claims description 3
• 229940056367 penicillin v Drugs 0.000 claims description 3
• BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• 125000003118 aryl group Chemical group 0.000 claims description 2
• 229960003237 betaine Drugs 0.000 claims description 2
• 125000002619 bicyclic group Chemical group 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 150000007524 organic acids Chemical group 0.000 claims description 2
• 229960004894 pheneticillin Drugs 0.000 claims description 2
• 229960003672 propicillin Drugs 0.000 claims description 2
• 201000010099 disease Diseases 0.000 claims 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
• MLYYVTUWGNIJIB-FFFFSGIJSA-N (6r)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-FFFFSGIJSA-N 0.000 claims 1
• YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims 1
• VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 claims 1
• GPXLMGHLHQJAGZ-JTDSTZFVSA-N nafcillin Chemical compound C1=CC=CC2=C(C(=O)N[C@@H]3C(N4[C@H](C(C)(C)S[C@@H]43)C(O)=O)=O)C(OCC)=CC=C21 GPXLMGHLHQJAGZ-JTDSTZFVSA-N 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 150000002960 penicillins Chemical class 0.000 description 17
• 230000000694 effects Effects 0.000 description 14
• 238000000338 in vitro Methods 0.000 description 11
• 241000894006 Bacteria Species 0.000 description 5
• 238000013207 serial dilution Methods 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 238000002474 experimental method Methods 0.000 description 3
• 235000002639 sodium chloride Nutrition 0.000 description 3
• 241000588724 Escherichia coli Species 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• 239000004480 active ingredient Substances 0.000 description 2
• 125000003368 amide group Chemical group 0.000 description 2
• 239000003708 ampul Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 230000001580 bacterial effect Effects 0.000 description 2
• XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• 238000011534 incubation Methods 0.000 description 2
• 238000011081 inoculation Methods 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 244000005700 microbiome Species 0.000 description 2
• 239000000825 pharmaceutical preparation Substances 0.000 description 2
• 125000005936 piperidyl group Chemical group 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000000243 solution Substances 0.000 description 2
• 238000002560 therapeutic procedure Methods 0.000 description 2
• PRPXIJHMIZZUNC-KPMSDPLLSA-N (6R)-8-oxo-3-(pyridin-2-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)CC2=NC=CC=C2)C(=O)O)C1=O PRPXIJHMIZZUNC-KPMSDPLLSA-N 0.000 description 1
• BWWVAEOLVKTZFQ-NTZNESFSSA-N Amdinocillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)=CN1CCCCCC1 BWWVAEOLVKTZFQ-NTZNESFSSA-N 0.000 description 1
• 208000035143 Bacterial infection Diseases 0.000 description 1
• 241000305071 Enterobacterales Species 0.000 description 1
• 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 1
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
• 240000008881 Oenanthe javanica Species 0.000 description 1
• 241000588769 Proteus <enterobacteria> Species 0.000 description 1
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 208000022362 bacterial infectious disease Diseases 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 231100000517 death Toxicity 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 231100000053 low toxicity Toxicity 0.000 description 1
• 229940127285 new chemical entity Drugs 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1