SU1424737A3 - Способ получени производных карбапенема - Google Patents

Способ получени производных карбапенема Download PDF

Info

Publication number: SU1424737A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mmol; water; mixture; solution; hept
Prior art date: 1983-12-01

Application number

SU843711600A

Other languages

English (en)

Russian (ru)

Inventor

Декстрейз Пьер

Original Assignee

Бристоль-Мейерз Компани (Фирма)

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.)

1983-12-01

Filing date

1984-03-07

Publication date

1988-09-15

1984-03-07 Application filed by Бристоль-Мейерз Компани (Фирма) filed Critical Бристоль-Мейерз Компани (Фирма)

1988-09-15 Application granted granted Critical

1988-09-15 Publication of SU1424737A3 publication Critical patent/SU1424737A3/ru

Links

238000000034 method Methods 0.000 title claims abstract description 25
YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title description 3
239000003960 organic solvent Substances 0.000 claims abstract description 25
239000005977 Ethylene Substances 0.000 claims abstract description 7
150000003573 thiols Chemical class 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 claims abstract 2
-1 keto ester Chemical class 0.000 claims description 60
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 57
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 22
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 21
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical class C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
GLUUGHFHXGJENI-UHFFFAOYSA-O hydron piperazine Chemical compound [H+].C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-O 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
229930194542 Keto Natural products 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 47
238000002360 preparation method Methods 0.000 abstract description 15
229940070891 pyridium Drugs 0.000 abstract description 11
QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical group NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 abstract description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 4
230000000844 anti-bacterial effect Effects 0.000 abstract description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 189
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 133
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 131
239000000203 mixture Substances 0.000 description 103
239000000243 solution Substances 0.000 description 92
239000007787 solid Substances 0.000 description 44
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JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 39
239000011541 reaction mixture Substances 0.000 description 39
238000004108 freeze drying Methods 0.000 description 37
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 28
239000003921 oil Substances 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
238000010828 elution Methods 0.000 description 26
239000000843 powder Substances 0.000 description 26
239000000047 product Substances 0.000 description 26
239000007864 aqueous solution Substances 0.000 description 25
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 22
239000010410 layer Substances 0.000 description 21
238000004587 chromatography analysis Methods 0.000 description 20
239000012299 nitrogen atmosphere Substances 0.000 description 20
239000012071 phase Substances 0.000 description 20
238000004366 reverse phase liquid chromatography Methods 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 18
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 18
239000008346 aqueous phase Substances 0.000 description 17
239000000463 material Substances 0.000 description 16
238000005984 hydrogenation reaction Methods 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 14
239000008363 phosphate buffer Substances 0.000 description 14
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 14
NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 13
HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
239000006188 syrup Substances 0.000 description 12
235000020357 syrup Nutrition 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
229910019142 PO4 Inorganic materials 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
238000001914 filtration Methods 0.000 description 9
BLTAPEIEHGWKKN-UHFFFAOYSA-N methanesulfonate;pyridin-1-ium Chemical compound CS(O)(=O)=O.C1=CC=NC=C1 BLTAPEIEHGWKKN-UHFFFAOYSA-N 0.000 description 9
239000010452 phosphate Substances 0.000 description 9
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 8
ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 8
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 7
239000000872 buffer Substances 0.000 description 7
ACWVAOJPKNFQCU-UHFFFAOYSA-N diphenyl hydrogen phosphate 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O.C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ACWVAOJPKNFQCU-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 7
239000008057 potassium phosphate buffer Substances 0.000 description 7
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
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PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
238000005406 washing Methods 0.000 description 5
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
AULOGPOZBOCNSX-UHFFFAOYSA-N 3-methylsulfanylpyridine Chemical compound CSC1=CC=CN=C1 AULOGPOZBOCNSX-UHFFFAOYSA-N 0.000 description 4
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 4
LVIPRKRYIVPTPB-UHFFFAOYSA-N Cl.CCCCC=C(C)C(O)=O Chemical compound Cl.CCCCC=C(C)C(O)=O LVIPRKRYIVPTPB-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000003756 stirring Methods 0.000 description 4
BSKHPKMHTQYZBB-UHFFFAOYSA-O 2-methylpyridin-1-ium Chemical compound CC1=CC=CC=[NH+]1 BSKHPKMHTQYZBB-UHFFFAOYSA-O 0.000 description 3
FKNQCJSGGFJEIZ-UHFFFAOYSA-O 4-methylpyridin-1-ium Chemical compound CC1=CC=[NH+]C=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-O 0.000 description 3
XCHSSZMKKXPBAI-UHFFFAOYSA-N 4-methylsulfanylpyridine Chemical compound CSC1=CC=NC=C1 XCHSSZMKKXPBAI-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
YWVYZMVYXAVAKS-UHFFFAOYSA-N pyridin-1-ium;trifluoromethanesulfonate Chemical compound C1=CC=[NH+]C=C1.[O-]S(=O)(=O)C(F)(F)F YWVYZMVYXAVAKS-UHFFFAOYSA-N 0.000 description 3
JNJFONBBNLVENC-UHFFFAOYSA-N 1h-imidazole;trifluoromethanesulfonic acid Chemical compound C1=CNC=N1.OS(=O)(=O)C(F)(F)F JNJFONBBNLVENC-UHFFFAOYSA-N 0.000 description 2
HIADZSOBMPSUGZ-UHFFFAOYSA-N 3-methoxypyridin-1-ium;chloride Chemical compound [Cl-].COC1=CC=C[NH+]=C1 HIADZSOBMPSUGZ-UHFFFAOYSA-N 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
KDTVWEHAAISPNW-UHFFFAOYSA-N 4-methylthiomorpholine Chemical compound CN1CCSCC1 KDTVWEHAAISPNW-UHFFFAOYSA-N 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
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 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
239000012971 dimethylpiperazine Substances 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
229910001386 lithium phosphate Inorganic materials 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000002780 morpholines Chemical class 0.000 description 2
XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 2
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 2
239000003643 water by type Substances 0.000 description 2
ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
LKIVEIAXFZBGMO-UHFFFAOYSA-N 1-methyl-2-methylsulfanylimidazole Chemical compound CSC1=NC=CN1C LKIVEIAXFZBGMO-UHFFFAOYSA-N 0.000 description 1
LTKMTXLIAZLQHS-UHFFFAOYSA-N 1-methylpyridine Chemical compound CN1C=CC=C=C1 LTKMTXLIAZLQHS-UHFFFAOYSA-N 0.000 description 1
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IHMXVSZXHFTOFN-UHFFFAOYSA-N 2-ethyloxolane Chemical compound CCC1CCCO1 IHMXVSZXHFTOFN-UHFFFAOYSA-N 0.000 description 1
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101100223892 Escherichia coli sulI gene Proteins 0.000 description 1
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
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150000001412 amines Chemical class 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical group OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
YYHQARSEKICSFC-UHFFFAOYSA-N diphenyl phosphate 4-methylthiomorpholin-4-ium Chemical compound C[NH+]1CCSCC1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 YYHQARSEKICSFC-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
ILVUABTVETXVMV-UHFFFAOYSA-N hydron;bromide;iodide Chemical compound Br.I ILVUABTVETXVMV-UHFFFAOYSA-N 0.000 description 1
230000003993 interaction Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
GXWXBVSXQWXEHX-UHFFFAOYSA-N methanesulfonic acid;2-methylpyridine Chemical compound CS([O-])(=O)=O.CC1=CC=CC=[NH+]1 GXWXBVSXQWXEHX-UHFFFAOYSA-N 0.000 description 1
QISWLEJRWWFHLF-UHFFFAOYSA-N methanesulfonic acid;4-methylpyridine Chemical compound CS([O-])(=O)=O.CC1=CC=[NH+]C=C1 QISWLEJRWWFHLF-UHFFFAOYSA-N 0.000 description 1
OVXDLDSWRLLUJT-UHFFFAOYSA-N morpholine;trifluoromethanesulfonic acid Chemical compound C1COCC[NH2+]1.[O-]S(=O)(=O)C(F)(F)F OVXDLDSWRLLUJT-UHFFFAOYSA-N 0.000 description 1
229960003753 nitric oxide Drugs 0.000 description 1
235000019391 nitrogen oxide Nutrition 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
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 1
239000011591 potassium Substances 0.000 description 1
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
239000011241 protective layer Substances 0.000 description 1
238000009738 saturating Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
229960003986 tuaminoheptane Drugs 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU843711600A 1983-12-01 1984-03-07 Способ получени производных карбапенема SU1424737A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US55729583A	1983-12-01	1983-12-01

Publications (1)

Publication Number	Publication Date
SU1424737A3 true SU1424737A3 (ru)	1988-09-15

Family

ID=24224831

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU843711600A SU1424737A3 (ru)	1983-12-01	1984-03-07	Способ получени производных карбапенема

Country Status (2)

Country	Link
CS (1)	CS250658B2 (cs)
SU (1)	SU1424737A3 (cs)

1984
- 1984-03-07 SU SU843711600A patent/SU1424737A3/ru active
- 1984-03-08 CS CS166984A patent/CS250658B2/cs unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Патент DE № 331253 3, кл. С 07 D 499/00, 1983. *

Also Published As

Publication number	Publication date
CS250658B2 (cs)	1987-05-14

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