CH686516A5 - 1-Beta-Methyl-2-thiolin-carbapenem-derivate. - Google Patents
1-Beta-Methyl-2-thiolin-carbapenem-derivate. Download PDFInfo
- Publication number
- CH686516A5 CH686516A5 CH176094A CH176094A CH686516A5 CH 686516 A5 CH686516 A5 CH 686516A5 CH 176094 A CH176094 A CH 176094A CH 176094 A CH176094 A CH 176094A CH 686516 A5 CH686516 A5 CH 686516A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- amino
- methyl
- carbapenem
- pyrr
- Prior art date
Links
- 239000003242 anti bacterial agent Substances 0.000 title description 3
- 229940088710 antibiotic agent Drugs 0.000 title description 3
- RQZQXIDILVWGOQ-HACHORDNSA-N (5S)-4-methyl-3-pyrrolidin-3-ylsulfanyl-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical compound N1CC(CC1)SC=1C([C@H]2N(C=1)C(C2)=O)C RQZQXIDILVWGOQ-HACHORDNSA-N 0.000 title 1
- -1 2-hydroxyethylamino, 3-hydroxypropylamino Chemical group 0.000 claims abstract description 94
- 150000001768 cations Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 238000002360 preparation method Methods 0.000 claims description 40
- 238000004519 manufacturing process Methods 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 150000003573 thiols Chemical class 0.000 claims description 5
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000007993 MOPS buffer Substances 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical group C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 claims 6
- 125000000129 anionic group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000008055 phosphate buffer solution Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000001450 anions Chemical class 0.000 abstract description 5
- 229940041011 carbapenems Drugs 0.000 abstract 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 151
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 28
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 28
- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical compound C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 5
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 5
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 101150116596 dhp-1 gene Proteins 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- GFXKPZGNSSQMFN-UHFFFAOYSA-N 2-methyl-3,7-dioxoheptanoic acid Chemical compound OC(=O)C(C)C(=O)CCCC=O GFXKPZGNSSQMFN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- DHSUYTOATWAVLW-WFVMDLQDSA-N cilastatin Chemical compound CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSC[C@H](N)C(O)=O)C(O)=O DHSUYTOATWAVLW-WFVMDLQDSA-N 0.000 description 2
- 229960004912 cilastatin Drugs 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- GGTLBEKHGWEAMM-WFASDCNBSA-N (4-nitrophenyl)methyl (2S,4S)-2-carbamoyl-2-(2-hydroxyethyl)-4-sulfanylpyrrolidine-1-carboxylate Chemical compound OCC[C@@]1(N(C[C@H](C1)S)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=O)N GGTLBEKHGWEAMM-WFASDCNBSA-N 0.000 description 1
- JUKCAGWFVURWLH-KEYYUXOJSA-N (4-nitrophenyl)methyl (2S,4S)-2-carbamoyl-2-[(2R)-2-hydroxybutyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound O[C@@H](C[C@@]1(N(C[C@H](C1)S)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=O)N)CC JUKCAGWFVURWLH-KEYYUXOJSA-N 0.000 description 1
- FPSAUHCUHHJTOF-HICWGWBUSA-N (4-nitrophenyl)methyl (2S,4S)-2-carbamoyl-2-[(2R)-2-hydroxypropyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound O[C@@H](C[C@@]1(N(C[C@H](C1)S)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=O)N)C FPSAUHCUHHJTOF-HICWGWBUSA-N 0.000 description 1
- FPSAUHCUHHJTOF-NKFCBESUSA-N (4-nitrophenyl)methyl (2S,4S)-2-carbamoyl-2-[(2S)-2-hydroxypropyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound O[C@H](C[C@@]1(N(C[C@H](C1)S)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=O)N)C FPSAUHCUHHJTOF-NKFCBESUSA-N 0.000 description 1
- DMTOKBBUPPNBFC-GJZGRUSLSA-N (4-nitrophenyl)methyl (2s,4s)-2-[bis(2-hydroxyethyl)carbamoyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound OCCN(CCO)C(=O)[C@@H]1C[C@H](S)CN1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 DMTOKBBUPPNBFC-GJZGRUSLSA-N 0.000 description 1
- NHIKLMSHQTWMLC-STQMWFEESA-N (4-nitrophenyl)methyl (2s,4s)-4-sulfanyl-2-(1,3-thiazole-2-carbonyl)pyrrolidine-1-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)N1[C@H](C(=O)C=2SC=CN=2)C[C@H](S)C1 NHIKLMSHQTWMLC-STQMWFEESA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- YKMONJZIUAOVEM-WDSKDSINSA-N 1beta-methylcarbapenem Chemical class C[C@H]1C=CN2C(=O)C[C@@H]12 YKMONJZIUAOVEM-WDSKDSINSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BKJXEZGPZLLYHX-UHFFFAOYSA-N 3,4-dihydro-2h-pyrrole-5-carbaldehyde Chemical compound O=CC1=NCCC1 BKJXEZGPZLLYHX-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms 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 3
- C07D477/20—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR930010878 | 1993-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH686516A5 true CH686516A5 (de) | 1996-04-15 |
Family
ID=19357425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH176094A CH686516A5 (de) | 1993-06-15 | 1994-06-03 | 1-Beta-Methyl-2-thiolin-carbapenem-derivate. |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH686516A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| TW (1) | TW252981B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101498989B (zh) * | 2008-01-28 | 2011-04-20 | 磐石国际股份有限公司 | 整合型装置显示单一磁盘驱动器代号的方法 |
-
1993
- 1993-10-30 TW TW82109093A patent/TW252981B/zh active
-
1994
- 1994-06-03 CH CH176094A patent/CH686516A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TW252981B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |