FI82250C - Foerfarande foer framstaellning av terapeutiskt aktiva 6-(1-hydroxietyl)-2-azacykloalkyl(alkylen)tio- 2-penem-3-karboxylsyrafoereningarna. - Google Patents

Foerfarande foer framstaellning av terapeutiskt aktiva 6-(1-hydroxietyl)-2-azacykloalkyl(alkylen)tio- 2-penem-3-karboxylsyrafoereningarna. Download PDF

Info

Publication number: FI82250C
Authority: FI; Finland
Prior art keywords: methyl; formula; solution; compound; alkylene
Prior art date: 1983-10-14

Application number

FI844023A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI844023L (fi

FI844023A0 (fi

FI82250B (fi

Inventor

Ernest Seiichi Hamanaka

Original Assignee

Pfizer

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.)

1983-10-14

Filing date

1984-10-12

Publication date

1991-02-11

1984-10-12 Application filed by Pfizer filed Critical Pfizer

1984-10-12 Publication of FI844023A0 publication Critical patent/FI844023A0/fi

1985-04-15 Publication of FI844023L publication Critical patent/FI844023L/fi

1990-10-31 Application granted granted Critical

1990-10-31 Publication of FI82250B publication Critical patent/FI82250B/fi

1991-02-11 Publication of FI82250C publication Critical patent/FI82250C/fi

Links

238000002360 preparation method Methods 0.000 title claims description 45
238000000034 method Methods 0.000 title claims description 27
125000002947 alkylene group Chemical group 0.000 title claims description 18
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 123
-1 carboxylic acid compound Chemical class 0.000 claims description 52
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 1
239000000243 solution Substances 0.000 description 102
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
238000005481 NMR spectroscopy Methods 0.000 description 25
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
239000000460 chlorine Substances 0.000 description 22
239000000203 mixture Substances 0.000 description 22
229920006395 saturated elastomer Polymers 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 16
239000011780 sodium chloride Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
239000007787 solid Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
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 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
239000011734 sodium Substances 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 9
238000002329 infrared spectrum Methods 0.000 description 9
239000007858 starting material Substances 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000002835 absorbance Methods 0.000 description 7
230000000844 anti-bacterial effect Effects 0.000 description 7
239000003826 tablet Substances 0.000 description 7
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229960001701 chloroform Drugs 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical class [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000007327 hydrogenolysis reaction Methods 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
244000005700 microbiome Species 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
150000003573 thiols Chemical class 0.000 description 4
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 4
JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
241000588914 Enterobacter Species 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
241000588748 Klebsiella Species 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
241000588771 Morganella <proteobacterium> Species 0.000 description 3
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
QYAMLDMULGSPEW-SCSAIBSYSA-N S1C(Br)(Br)CN2C(=O)C[C@H]21 Chemical compound S1C(Br)(Br)CN2C(=O)C[C@H]21 QYAMLDMULGSPEW-SCSAIBSYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001412 amines Chemical group 0.000 description 3
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
239000006260 foam Substances 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 3
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003462 sulfoxides Chemical class 0.000 description 3
DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 3
239000012989 trithiocarbonate Substances 0.000 description 3
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
IOGISYQVOGVIEU-UHFFFAOYSA-N 4-hydroxypyrrolidin-2-one Chemical compound OC1CNC(=O)C1 IOGISYQVOGVIEU-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
BNBZWXGPZCJUEK-GPYLVKOQSA-N CCCC[C@@H](CO[SiH](C)C)[C@@H]1[C@@H]2N(C1=O)C(=C(S2)S(=O)CC)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-] Chemical compound CCCC[C@@H](CO[SiH](C)C)[C@@H]1[C@@H]2N(C1=O)C(=C(S2)S(=O)CC)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-] BNBZWXGPZCJUEK-GPYLVKOQSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
241000588768 Providencia Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000008272 agar Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
KZHCQYYXHVVEPK-UHFFFAOYSA-M ethanethioate;tetrabutylazanium Chemical compound CC([O-])=S.CCCC[N+](CCCC)(CCCC)CCCC KZHCQYYXHVVEPK-UHFFFAOYSA-M 0.000 description 2
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical class CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000008101 lactose Substances 0.000 description 2
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000000746 purification Methods 0.000 description 2
125000000719 pyrrolidinyl group Chemical group 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
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125000004665 trialkylsilyl group Chemical group 0.000 description 2
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
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XZXRYNVWWTZADH-UHFFFAOYSA-N (2-oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1NC(=O)OC1 XZXRYNVWWTZADH-UHFFFAOYSA-N 0.000 description 1
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MKWSXSIIWQQWFB-UHFFFAOYSA-N (2-oxopyrrolidin-3-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1C(=O)NCC1 MKWSXSIIWQQWFB-UHFFFAOYSA-N 0.000 description 1
JESMSJZDKNVWNX-UHFFFAOYSA-N (4-nitrophenyl)methyl 2,2-dihydroxyacetate Chemical compound OC(O)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 JESMSJZDKNVWNX-UHFFFAOYSA-N 0.000 description 1
HKQZCKKTMKXNPZ-UHFFFAOYSA-N (5-oxopyrrolidin-3-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1CC(=O)NC1 HKQZCKKTMKXNPZ-UHFFFAOYSA-N 0.000 description 1
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125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
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RYKLZUPYJFFNRR-UHFFFAOYSA-N 3-hydroxypiperidin-2-one Chemical compound OC1CCCNC1=O RYKLZUPYJFFNRR-UHFFFAOYSA-N 0.000 description 1
HDACDDSPBQTVCH-UHFFFAOYSA-N 3-hydroxypyrrolidine-1-carbaldehyde Chemical compound OC1CCN(C=O)C1 HDACDDSPBQTVCH-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
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SVYGWEOKLACROM-UHFFFAOYSA-N C1CC(CN(C1)C=O)CC2=CC=C(C=C2)S(=O)(=O)O Chemical compound C1CC(CN(C1)C=O)CC2=CC=C(C=C2)S(=O)(=O)O SVYGWEOKLACROM-UHFFFAOYSA-N 0.000 description 1
QMYDWMPNVBDQDN-AIDRMFRGSA-N CCCCC[C@@H](CO[SiH3])[C@@H]1[C@@H]2N(C1=O)C(=C(S2)S(=O)CC)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-] Chemical compound CCCCC[C@@H](CO[SiH3])[C@@H]1[C@@H]2N(C1=O)C(=C(S2)S(=O)CC)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-] QMYDWMPNVBDQDN-AIDRMFRGSA-N 0.000 description 1
GFPMKPZCSNHRDO-YMTYPPQLSA-N CCCCC[SiH2]O[C@H](C)[C@@H]1[C@@H]2N(C1=O)C(=C(S2)CC)C(=S)OCC3=CC=C(C=C3)[N+](=O)[O-] Chemical compound CCCCC[SiH2]O[C@H](C)[C@@H]1[C@@H]2N(C1=O)C(=C(S2)CC)C(=S)OCC3=CC=C(C=C3)[N+](=O)[O-] GFPMKPZCSNHRDO-YMTYPPQLSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
AUMXSPLHHVLZCJ-UHFFFAOYSA-N CN1CC(COC1=O)CC2=CC=C(C=C2)S(=O)(=O)O Chemical compound CN1CC(COC1=O)CC2=CC=C(C=C2)S(=O)(=O)O AUMXSPLHHVLZCJ-UHFFFAOYSA-N 0.000 description 1
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
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239000005977 Ethylene Substances 0.000 description 1
241000606768 Haemophilus influenzae Species 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
241000607720 Serratia Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
JSWAHRJBQMEUQL-UHFFFAOYSA-N [3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate Chemical compound CC(=O)OC1NC(=O)C1CCO[Si](C)(C)C(C)(C)C JSWAHRJBQMEUQL-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
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150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
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239000003242 anti bacterial agent Substances 0.000 description 1
229940126573 antibacterial therapeutic Drugs 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
QTTOHHKREBRZNF-UHFFFAOYSA-N azetidin-1-yl 2-oxoacetate Chemical compound O=CC(=O)ON1CCC1 QTTOHHKREBRZNF-UHFFFAOYSA-N 0.000 description 1
125000005604 azodicarboxylate group Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
125000006358 carbonyl ethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
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229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
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238000006482 condensation reaction Methods 0.000 description 1
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239000012153 distilled water Substances 0.000 description 1
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238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
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238000002523 gelfiltration Methods 0.000 description 1
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244000000058 gram-negative pathogen Species 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
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238000001802 infusion Methods 0.000 description 1
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230000002401 inhibitory effect Effects 0.000 description 1
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238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
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ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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235000019359 magnesium stearate Nutrition 0.000 description 1
CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
125000006502 nitrobenzyl group Chemical group 0.000 description 1
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AKHJQEDIHGNACJ-UHFFFAOYSA-N o-(1-formylpiperidin-3-yl) ethanethioate Chemical compound CC(=S)OC1CCCN(C=O)C1 AKHJQEDIHGNACJ-UHFFFAOYSA-N 0.000 description 1
YYNRMDWIGKJCAI-UHFFFAOYSA-N o-(1-methyl-2-oxopiperidin-3-yl) ethanethioate Chemical compound CN1CCCC(OC(C)=S)C1=O YYNRMDWIGKJCAI-UHFFFAOYSA-N 0.000 description 1
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OKWCCYNFBHTTIA-UHFFFAOYSA-N o-(2-oxopyrrolidin-3-yl) ethanethioate Chemical compound CC(=S)OC1CCNC1=O OKWCCYNFBHTTIA-UHFFFAOYSA-N 0.000 description 1
YVPDOVNLHWIAAE-UHFFFAOYSA-N o-[(2-oxo-1,3-oxazolidin-4-yl)methyl] ethanethioate Chemical compound CC(=S)OCC1COC(=O)N1 YVPDOVNLHWIAAE-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
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CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000002217 penem group Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
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239000003495 polar organic solvent Substances 0.000 description 1
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
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125000006239 protecting group Chemical group 0.000 description 1
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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
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 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
230000003595 spectral effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
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239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
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235000012222 talc Nutrition 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
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230000017105 transposition Effects 0.000 description 1
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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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

FI844023A 1983-10-14 1984-10-12 Foerfarande foer framstaellning av terapeutiskt aktiva 6-(1-hydroxietyl)-2-azacykloalkyl(alkylen)tio- 2-penem-3-karboxylsyrafoereningarna. FI82250C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US54231083A	1983-10-14	1983-10-14
US54231083		1983-10-14

Publications (4)

Publication Number	Publication Date
FI844023A0 FI844023A0 (fi)	1984-10-12
FI844023L FI844023L (fi)	1985-04-15
FI82250B FI82250B (fi)	1990-10-31
FI82250C true FI82250C (fi)	1991-02-11

Family

ID=24163252

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI844023A FI82250C (fi)	1983-10-14	1984-10-12	Foerfarande foer framstaellning av terapeutiskt aktiva 6-(1-hydroxietyl)-2-azacykloalkyl(alkylen)tio- 2-penem-3-karboxylsyrafoereningarna.

Country Status (14)

Country	Link
JP (1)	JPS60120881A (es)
KR (1)	KR870000525B1 (es)
DD (1)	DD223453A5 (es)
EG (1)	EG16589A (es)
ES (1)	ES8602012A1 (es)
FI (1)	FI82250C (es)
HU (1)	HU194248B (es)
NO (1)	NO167573C (es)
PH (1)	PH20520A (es)
PL (1)	PL150059B1 (es)
PT (1)	PT79346B (es)
SU (1)	SU1340590A3 (es)
YU (1)	YU44241B (es)
ZA (1)	ZA847982B (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2660243B2 (ja) *	1985-08-08	1997-10-08	株式会社半導体エネルギー研究所	半導体装置作製方法
JPS6247116A (ja) *	1985-08-26	1987-02-28	Semiconductor Energy Lab Co Ltd	半導体装置製造装置
JPS6251210A (ja) *	1985-08-30	1987-03-05	Semiconductor Energy Lab Co Ltd	半導体装置作製方法
JPS6252924A (ja) *	1985-09-01	1987-03-07	Semiconductor Energy Lab Co Ltd	半導体装置作製方法
JPH0696580B2 (ja) *	1985-09-17	1994-11-30	三共株式会社	ペネム−３−カルボン酸誘導体
JPS6269608A (ja) *	1985-09-24	1987-03-30	Semiconductor Energy Lab Co Ltd	半導体装置作製方法
JP2006001841A (ja) *	2004-06-15	2006-01-05	Sumitomo Chemical Co Ltd	含窒素へテロ環化合物の製造方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57176988A (en) *	1981-04-09	1982-10-30	Sankyo Co Ltd	Penam-3-carboxylic acid derivative and its preparation
JPS57200392A (en) *	1981-06-03	1982-12-08	Sankyo Co Ltd	Penem-3-carboxylic acid derivative and its preparation
EP0110280B1 (en) *	1982-11-29	1994-10-12	Schering Corporation	Process for the production of penem compounds
US4614738A (en) *	1983-03-25	1986-09-30	Schering Corporation	2-(N-heterocycloaliphaticthio)penems

1984
- 1984-10-10 YU YU1735/84A patent/YU44241B/xx unknown
- 1984-10-11 ES ES536687A patent/ES8602012A1/es not_active Expired
- 1984-10-11 PT PT79346A patent/PT79346B/pt not_active IP Right Cessation
- 1984-10-12 SU SU843804830A patent/SU1340590A3/ru active
- 1984-10-12 NO NO844090A patent/NO167573C/no unknown
- 1984-10-12 FI FI844023A patent/FI82250C/fi not_active IP Right Cessation
- 1984-10-12 HU HU843830A patent/HU194248B/hu not_active IP Right Cessation
- 1984-10-12 DD DD84268285A patent/DD223453A5/de not_active IP Right Cessation
- 1984-10-12 ZA ZA847982A patent/ZA847982B/xx unknown
- 1984-10-12 PH PH31330A patent/PH20520A/en unknown
- 1984-10-13 EG EG628/84A patent/EG16589A/xx active
- 1984-10-13 KR KR1019840006347A patent/KR870000525B1/ko not_active Expired
- 1984-10-15 JP JP59216022A patent/JPS60120881A/ja active Pending
- 1984-10-15 PL PL1984250031A patent/PL150059B1/pl unknown

Also Published As

Publication number	Publication date
HUT35264A (en)	1985-06-28
ES536687A0 (es)	1985-11-16
NO167573B (no)	1991-08-12
PH20520A (en)	1987-01-30
DD223453A5 (de)	1985-06-12
YU173584A (en)	1987-02-28
NO844090L (no)	1985-04-15
PL250031A1 (en)	1985-07-02
FI844023L (fi)	1985-04-15
JPS60120881A (ja)	1985-06-28
NO167573C (no)	1991-11-20
ES8602012A1 (es)	1985-11-16
PL150059B1 (en)	1990-04-30
ZA847982B (en)	1986-05-28
FI844023A0 (fi)	1984-10-12
KR850002987A (ko)	1985-05-28
KR870000525B1 (ko)	1987-03-14
SU1340590A3 (ru)	1987-09-23
YU44241B (en)	1990-04-30
FI82250B (fi)	1990-10-31
PT79346B (en)	1986-11-20
HU194248B (en)	1988-01-28
PT79346A (en)	1984-11-01
EG16589A (en)	1989-03-30

Publication	Publication Date	Title
FI83419B (fi)	1991-03-28	Foerfarande foer framstaellning av som laekemedel anvaendbara 1,2,6-substituerad karbapen-2-em-3-karboxylsyra.
US4619924A (en)	1986-10-28	2-alkylthiopenem derivatives
US5459260A (en)	1995-10-17	Tricyclic or tetracyclic carbapenem compounds, their production and use
FI82250C (fi)	1991-02-11	Foerfarande foer framstaellning av terapeutiskt aktiva 6-(1-hydroxietyl)-2-azacykloalkyl(alkylen)tio- 2-penem-3-karboxylsyrafoereningarna.
EP0130025B1 (en)	1987-07-08	2-alkylthiopenem derivatives
US4772597A (en)	1988-09-20	2-azacycloalkylthiopenem derivatives
AU593874B2 (en)	1990-02-22	2-heterocyclylthio penems
US4614737A (en)	1986-09-30	2-dioxacycloalkylthiopenem derivatives
CA2111974C (en)	2001-07-24	Carbapenem derivatives
FI81355B (fi)	1990-06-29	Foerfarande foer framstaellning av antibakteriella 2-dioxacykloalkyltiopenemderivat.
EP0132101A1 (en)	1985-01-23	2-Heterocycloalkylthiopenem derivatives
FI81584C (fi)	1990-11-12	Foerfarande foer framstaellning av antibakteriella 6-alfa-hydroxietyl-2-substituerad-2-penem-3-karboxylsyror.
KR0128513B1 (ko)	1998-04-04	신규한 항균성 페넴 유도체와 그의 제조방법
PL150254B1 (es)	1990-05-31
JPH0529356B2 (es)	1993-04-30
JP3003002B2 (ja)	2000-01-24	三環性カルバペネム化合物
KR100231498B1 (ko)	1999-11-15	베타메틸 카르바페넴 유도체 및 그의 제조 방법
NO842882L (no)	1985-01-15	Fremgangsmaate for fremstilling av antibakterielle 2-heterocykloalkyltiopenem-derivater

Legal Events

Date	Code	Title	Description
1994-05-13	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: PFIZER INC.