DK169623B1 - 2-Pyridyl-penem-forbindelser og salte deraf, fremgangsmåde til deres fremstilling samt farmaceutiske præparater indeholdende disse forbindelser - Google Patents

2-Pyridyl-penem-forbindelser og salte deraf, fremgangsmåde til deres fremstilling samt farmaceutiske præparater indeholdende disse forbindelser Download PDF

Info

Publication number: DK169623B1
Authority: DK; Denmark
Prior art keywords: group; pyridyl; penem; compounds; compound
Prior art date: 1986-05-06

Application number

DK228687A

Other languages

Danish (da)

English (en)

Other versions

DK228687D0 (da

DK228687A (da

Inventor

Marc Lang

Original Assignee

Ciba Geigy Ag

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.)

1986-05-06

Filing date

1987-05-05

Publication date

1994-12-27

1987-05-05 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1987-05-05 Publication of DK228687D0 publication Critical patent/DK228687D0/da

1987-11-07 Publication of DK228687A publication Critical patent/DK228687A/da

1994-12-27 Application granted granted Critical

1994-12-27 Publication of DK169623B1 publication Critical patent/DK169623B1/da

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 130
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238000000034 method Methods 0.000 title claims abstract description 22
230000008569 process Effects 0.000 title claims abstract description 9
238000002360 preparation method Methods 0.000 title claims description 13
CWFAMVUHPHYDIO-SNVBAGLBSA-N (5r)-3-pyridin-2-yl-4-thia-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class S([C@@H]1CC(N1C=1)=O)C=1C1=CC=CC=N1 CWFAMVUHPHYDIO-SNVBAGLBSA-N 0.000 title claims description 5
239000000825 pharmaceutical preparation Substances 0.000 title description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 54
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125000000217 alkyl group Chemical group 0.000 claims abstract description 27
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 23
-1 aminolavalkylthio Chemical group 0.000 claims description 212
239000002253 acid Substances 0.000 claims description 22
125000003277 amino group Chemical group 0.000 claims description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
125000000524 functional group Chemical group 0.000 claims description 11
230000004962 physiological condition Effects 0.000 claims description 10
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150000002148 esters Chemical group 0.000 claims description 9
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 7
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125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000011574 phosphorus Substances 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
BFYPGIMLKFZWEI-UTMSNSNXSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-pyridin-3-yl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical group S([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C1=CC=CN=C1 BFYPGIMLKFZWEI-UTMSNSNXSA-N 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 3
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150000001768 cations Chemical class 0.000 claims description 3
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125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
PGJFRMGIRXBTID-XYZUUMPBSA-N (5r,6s)-3-(6-aminopyridin-3-yl)-6-[(1r)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical group S([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C1=CC=C(N)N=C1 PGJFRMGIRXBTID-XYZUUMPBSA-N 0.000 claims 1
WYJQBZUHDURGNF-BZTNIEFMSA-N (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-(6-methylpyridin-3-yl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical group S([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1C1=CC=C(C)N=C1 WYJQBZUHDURGNF-BZTNIEFMSA-N 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
SFIPPEJRUGDKRJ-OTDPEBBPSA-N acetyloxymethyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-pyridin-3-yl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical group S([C@@H]1[C@H](C(N1C=1C(=O)OCOC(C)=O)=O)[C@H](O)C)C=1C1=CC=CN=C1 SFIPPEJRUGDKRJ-OTDPEBBPSA-N 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
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239000011593 sulfur Substances 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 abstract description 5
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239000000243 solution Substances 0.000 description 22
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238000006243 chemical reaction Methods 0.000 description 19
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239000007858 starting material Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 14
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150000001340 alkali metals Chemical class 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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241000191967 Staphylococcus aureus Species 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 7
239000003480 eluent Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
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SQTLHDANMOBRDP-ADOANMRESA-M [Na+].N1=CC(=CC=C1)C=1S[C@H]2N(C=1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O Chemical compound [Na+].N1=CC(=CC=C1)C=1S[C@H]2N(C=1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O SQTLHDANMOBRDP-ADOANMRESA-M 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
208000015181 infectious disease Diseases 0.000 description 6
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
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FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
239000002904 solvent Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
239000013543 active substance Substances 0.000 description 5
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
PHGLYQGVAGLHTN-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetic acid Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)O)C1=CC=CC=C1 PHGLYQGVAGLHTN-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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238000003776 cleavage reaction Methods 0.000 description 3
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DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 3
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
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239000011668 ascorbic acid Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000003939 benzylamines Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical group [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
TYDNJWBMRMCVEU-HMIRJHDYSA-L disodium (5R)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C1[C@@H]2N(C1=O)C(=CS2)C(=O)[O-].C1[C@@H]2N(C1=O)C(=CS2)C(=O)[O-].[Na+].[Na+] TYDNJWBMRMCVEU-HMIRJHDYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
239000012374 esterification agent Substances 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229960002050 hydrofluoric acid Drugs 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003951 lactams Chemical group 0.000 description 1
150000002596 lactones Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910001416 lithium ion Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960003085 meticillin Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000007344 nucleophilic reaction Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
HNOLIWBAJVIBOU-UHFFFAOYSA-N prop-2-enyl 2-chloro-2-oxoacetate Chemical compound ClC(=O)C(=O)OCC=C HNOLIWBAJVIBOU-UHFFFAOYSA-N 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229940054334 silver cation Drugs 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 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
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
239000008137 solubility enhancer Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
238000010257 thawing Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 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
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Cephalosporin Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)

DK228687A 1986-05-06 1987-05-05 2-Pyridyl-penem-forbindelser og salte deraf, fremgangsmåde til deres fremstilling samt farmaceutiske præparater indeholdende disse forbindelser DK169623B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH184686		1986-05-06
CH184686		1986-05-06

Publications (3)

Publication Number	Publication Date
DK228687D0 DK228687D0 (da)	1987-05-05
DK228687A DK228687A (da)	1987-11-07
DK169623B1 true DK169623B1 (da)	1994-12-27

Family

ID=4219979

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK228687A DK169623B1 (da)	1986-05-06	1987-05-05	2-Pyridyl-penem-forbindelser og salte deraf, fremgangsmåde til deres fremstilling samt farmaceutiske præparater indeholdende disse forbindelser

Country Status (14)

Country	Link
US (1)	US4826832A (fr)
EP (1)	EP0246187B1 (fr)
JP (1)	JPS62263183A (fr)
AT (1)	ATE72438T1 (fr)
AU (1)	AU603795B2 (fr)
CA (1)	CA1293502C (fr)
DE (1)	DE3776590D1 (fr)
DK (1)	DK169623B1 (fr)
ES (1)	ES2038207T3 (fr)
GR (1)	GR3003735T3 (fr)
IE (1)	IE59714B1 (fr)
NZ (1)	NZ220195A (fr)
PT (1)	PT84819B (fr)
ZA (1)	ZA873198B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0003960B1 (fr) *	1978-02-02	1983-06-29	Ciba-Geigy Ag	Composés thia-aza substitués en position 6, leur préparation et compositions pharmaceutiques les contenant
EP0215739B1 (fr) *	1985-09-11	1993-09-01	Ciba-Geigy Ag	Synthèse de dérivés de bêta-lactame
GB8716679D0 (en) *	1987-07-15	1987-08-19	Erba Farmitalia	Penem derivatives
EP0462521A1 (fr) *	1990-06-19	1991-12-27	Takeda Chemical Industries, Ltd.	Pénème cristallin, sa préparation et son utilisation
US5492903A (en) *	1990-06-19	1996-02-20	Takeda Chemical Industries Ltd.	Crystalline esters of (+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]he
EP0499274A1 (fr) *	1991-02-15	1992-08-19	Takeda Chemical Industries, Ltd.	Pénème cristallin, sa production et son application
CA2110184C (fr) *	1991-06-06	2003-04-15	J. Stuart Cumming	Lentille intraoculaire avec plaque de fixation haptique
EP0597401A3 (fr) *	1992-11-11	1995-07-26	Takeda Chemical Industries Ltd	Préparation de pénèmes.
US20040202714A1 (en) *	1999-10-12	2004-10-14	Daiichi Suntory Pharma Co., Ltd.	Oral pharmaceutical composition
DE60008497T2 (de) *	1999-10-12	2004-12-02	Daiichi Suntory Pharma Co., Ltd.	Arzneimittel zur oralen verabreichung

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4168314A (en) *	1977-11-17	1979-09-18	Merck & Co., Inc.	6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid
EP0003960B1 (fr) *	1978-02-02	1983-06-29	Ciba-Geigy Ag	Composés thia-aza substitués en position 6, leur préparation et compositions pharmaceutiques les contenant
US4272437A (en) *	1978-12-18	1981-06-09	Bristol-Myers Company	Antibacterial agents, and 4-thio azetidinone intermediates
IL58576A (en) *	1978-12-18	1985-12-31	Bristol Myers Co	2-substituted and 2,6-disubstituted penem compounds,their preparation and pharmaceutical compositions containing them
JPS5625110A (en) *	1978-12-18	1981-03-10	Bristol Myers Co	Antibacterial
US4386030A (en) *	1979-12-31	1983-05-31	Merck & Co., Inc.	Process for preparing 6-(1'-hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acid
DE3277696D1 (en) *	1981-07-15	1987-12-23	Sumitomo Pharma	Carboxylic beta-lactam compounds and the preparation thereof
NZ201471A (en) *	1981-08-10	1985-09-13	Merck & Co Inc	Antibacterial compositions containing penems and dipeptidase inhibitors
EP0109362A1 (fr) *	1982-11-16	1984-05-23	Ciba-Geigy Ag	Composés hétérocycliques, procédé pour leur préparation, compositions pharmaceutiques les contenant et leur application
US4540580A (en) *	1982-11-16	1985-09-10	Schering Corporation	2-[(1'R)-1'-Aminoalkyl]penems
DE3366926D1 (en) *	1982-11-16	1986-11-20	Schering Corp	Penems, pharmaceutical compositions containing them, process for preparing them
EP0148128A3 (fr) *	1983-12-30	1985-08-07	Ciba-Geigy Ag	Dérivés de pénème optiquement actifs
GB8416652D0 (en) *	1984-06-29	1984-08-01	Erba Farmitalia	Penem derivatives
US4617300A (en) *	1984-09-21	1986-10-14	Schering Corporation	2(N-heterocyclyl) penems
EP0199675A1 (fr) *	1985-04-17	1986-10-29	Ciba-Geigy Ag	Dérivés d'hétérocyclylpénème

1987
- 1987-04-27 US US07/042,768 patent/US4826832A/en not_active Expired - Lifetime
- 1987-04-30 ES ES198787810278T patent/ES2038207T3/es not_active Expired - Lifetime
- 1987-04-30 AT AT87810278T patent/ATE72438T1/de not_active IP Right Cessation
- 1987-04-30 EP EP87810278A patent/EP0246187B1/fr not_active Expired - Lifetime
- 1987-04-30 DE DE8787810278T patent/DE3776590D1/de not_active Expired - Lifetime
- 1987-05-01 JP JP62106454A patent/JPS62263183A/ja active Granted
- 1987-05-04 CA CA000536310A patent/CA1293502C/fr not_active Expired - Lifetime
- 1987-05-04 PT PT84819A patent/PT84819B/pt unknown
- 1987-05-05 AU AU72512/87A patent/AU603795B2/en not_active Expired
- 1987-05-05 DK DK228687A patent/DK169623B1/da not_active IP Right Cessation
- 1987-05-05 NZ NZ220195A patent/NZ220195A/xx unknown
- 1987-05-05 ZA ZA873198A patent/ZA873198B/xx unknown
- 1987-05-11 IE IE118287A patent/IE59714B1/en not_active IP Right Cessation
1992
- 1992-02-06 GR GR910402104T patent/GR3003735T3/el unknown

Also Published As

Publication number	Publication date
JPH0339514B2 (fr)	1991-06-14
IE871182L (en)	1987-11-06
IE59714B1 (en)	1994-03-23
PT84819A (en)	1987-06-01
AU603795B2 (en)	1990-11-29
GR3003735T3 (fr)	1993-03-16
DE3776590D1 (de)	1992-03-19
NZ220195A (en)	1989-01-06
ATE72438T1 (de)	1992-02-15
EP0246187B1 (fr)	1992-02-05
US4826832A (en)	1989-05-02
AU7251287A (en)	1987-11-12
ES2038207T3 (es)	1993-07-16
CA1293502C (fr)	1991-12-24
ZA873198B (en)	1987-12-30
EP0246187A3 (en)	1988-03-16
PT84819B (pt)	1989-12-29
DK228687D0 (da)	1987-05-05
DK228687A (da)	1987-11-07
JPS62263183A (ja)	1987-11-16
EP0246187A2 (fr)	1987-11-19

Legal Events

Date	Code	Title
1990-06-11	ATS	Application withdrawn
1994-12-27	B1	Patent granted (law 1993)
2007-05-21	PUP	Patent expired

Publication	Publication Date	Title
US4552873A (en)	1985-11-12	Carbapenem compounds, and compositions containing them
EP0176064A1 (fr)	1986-04-02	Intermédiaires pour la préparation de dérivés de 7-oxo-4-thia-1-aza-[3,2,0]heptane et de 7-oxo-4-thia-1-aza[3,2,0]hept-2-éne
EP0451764A1 (fr)	1991-10-16	Composés de carbapénème
AU603795B2 (en)	1990-11-29	Pyridine compounds
DK170341B1 (da)	1995-08-07	Penem-derivater, fremgangsmåde til fremstilling heraf og farmaceutiske og veterinære præparater indeholdende disse forbindelser
FI89490B (fi)	1993-06-30	Foerfarande foer framstaellning av 2-metoximetyl-penemderivat
FI89714B (fi)	1993-07-30	Foerfarande foer framstaellning av terapeutiskt verkande 2-penem-3-karboxylsyraderivat
NO834189L (no)	1984-05-18	Fremgangsmaate til fremstilling av 6-hydroksy-laverealkyl-penem-forbindelser
KR100530478B1 (ko)	2005-11-23	카르바페넴 화합물, 이의 용도 및 이의 중간체 화합물
US4656165A (en)	1987-04-07	Aminomethyl penem compounds
JPH03120280A (ja)	1991-05-22	ハロメチルカルバペネム化合物の製法
NO841789L (no)	1984-11-07	Fremgangsmaate til fremstilling av aminolaverealkylpenem-forbindelse
NO834191L (no)	1984-05-18	Fremgangsmaate til fremstilling av heterocykliske forbindelser
EP0199675A1 (fr)	1986-10-29	Dérivés d'hétérocyclylpénème
NO841788L (no)	1984-11-07	Heterocyklyl-lavalkyl-penem-forbindelser, fremgangsmaate til deres fremstilling, farmasoeytiske preparater, inneholdende disse forbindelser og anvendelse av sistnevnte
US4540580A (en)	1985-09-10	2-[(1'R)-1'-Aminoalkyl]penems
FI81584B (fi)	1990-07-31	Foerfarande foer framstaellning av antibakteriella 6-alfa-hydroxietyl-2-substituerad-2-penem-3-karboxylsyror.
DD260070A5 (de)	1988-09-14	Verfahren zur herstellung von aminoacyloxymethyl-verbindungen
NO853142L (no)	1986-02-10	Nye aminoalkylpenem-fobindelser.
NO845277L (no)	1985-07-01	Fremgangsmaate til fremstilling av nye optisk aktive penemforbindelser.
KR100246950B1 (ko)	2000-05-01	신규 카바페넴계 항생제 및 그의 제조방법
KR100246951B1 (ko)	2000-05-01	신규 카바페넴계 항생제 및 그의 제조방법
EP0275233A1 (fr)	1988-07-20	Dérivés de 2-hétérocyclylalkyl-2-pénème
NO824067L (no)	1983-06-06	Aminobutylforbindelser.
EP0597401A2 (fr)	1994-05-18	Préparation de pénèmes