FI59103C - Mellanprodukter till anvaendning vid framstaellning av alfa-aminopenicillinestrar - Google Patents
Mellanprodukter till anvaendning vid framstaellning av alfa-aminopenicillinestrar Download PDFInfo
- Publication number
- FI59103C FI59103C FI791386A FI791386A FI59103C FI 59103 C FI59103 C FI 59103C FI 791386 A FI791386 A FI 791386A FI 791386 A FI791386 A FI 791386A FI 59103 C FI59103 C FI 59103C
- Authority
- FI
- Finland
- Prior art keywords
- penicillanate
- ester
- tai
- sodium
- moolia
- Prior art date
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- 150000002148 esters Chemical class 0.000 claims description 40
- 239000000460 chlorine Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 claims 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 109
- -1 tetrahydrofurania Chemical compound 0.000 description 67
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- 239000000047 product Substances 0.000 description 41
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 39
- 229940093499 ethyl acetate Drugs 0.000 description 37
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 229910001868 water Inorganic materials 0.000 description 37
- 238000010521 absorption reaction Methods 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 32
- 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 31
- 229910052708 sodium Inorganic materials 0.000 description 31
- 239000011734 sodium Substances 0.000 description 31
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- 239000003054 catalyst Substances 0.000 description 20
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- 230000012010 growth Effects 0.000 description 18
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 15
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910000564 Raney nickel Inorganic materials 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 125000004185 ester group Chemical group 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 239000000284 extract Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
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- 238000003756 stirring Methods 0.000 description 8
- 239000007868 Raney catalyst Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- CGKKDGMMKSOGLM-UHFFFAOYSA-N 1-chloroethyl acetate Chemical compound CC(Cl)OC(C)=O CGKKDGMMKSOGLM-UHFFFAOYSA-N 0.000 description 6
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
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- 230000002378 acidificating effect Effects 0.000 description 6
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- 230000003197 catalytic effect Effects 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
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- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
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- BYRRPYMBVHTVKO-UHFFFAOYSA-N [Na].[Ti] Chemical compound [Na].[Ti] BYRRPYMBVHTVKO-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 229910000573 alkali metal alloy Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 210000003423 ankle Anatomy 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 229960001212 bacterial vaccine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CVASMYWHWRNWOX-UHFFFAOYSA-N chloro methyl carbonate Chemical compound COC(=O)OCl CVASMYWHWRNWOX-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- RTFGZMKXMSDULM-UHFFFAOYSA-N chloromethyl ethyl carbonate Chemical compound CCOC(=O)OCCl RTFGZMKXMSDULM-UHFFFAOYSA-N 0.000 description 1
- JHYNXXBAHWPABC-UHFFFAOYSA-N chloromethyl propan-2-yl carbonate Chemical compound CC(C)OC(=O)OCCl JHYNXXBAHWPABC-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N delta-valerolactam Natural products O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 description 1
- 238000010932 ethanolysis reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate 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
- 230000004060 metabolic process Effects 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N methanediimine Chemical compound N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic 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
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical group ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 150000003954 δ-lactams Chemical class 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
-
- 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)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (4)
- 43 591 03
- 1. Välituote a-amincpenisilliiniestereiden ja niiden farmaseuttisesti hyväksyttävien happoadditiosuolojen valmistamiseksi, joilla on kaava /s\ /CH3 R - CH - CO - NH - CH - CH C I I I Pch3 , NH2 0=C — N -CH - COO - R jossa R on 2-7 hiiliatomia sisältävä alkyyli tai fenyyliryhmä, joka voi olla substituoitu halogeenilla, kuten kloorilla tai fluorilla, ja jossa R^ on CH- O • J "4 - CH - O - C - R tai R5 O I M A -CH-O-C-O-R 4 5 jossa R tarkoittaa 1-4 hiiliatomia sisältävää alkyyliä ja R on H, -CH^ tai -C^H^, tunnettu siitä, että sillä on kaava /CH3 R - CH - CONH - CH - CH C I I I I^ch3 N3 0=C — N - CH - COO - RX jossa R ja R^ tarkoittavat samaa kuin yllä.
- 2. Patenttivaatimuksen 1 mukainen välituote, tunnettu siitä, että R on fenyyli, ja R* on ryhmä R^ O I n a -CH-O-C-O-R, 5 4 jossa R on metyyli- ja R on etyyliryhmä.
- 1. Mellanprodukt för framställning av a-aminopenicillinest-rar med formeln
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1268870 | 1970-09-17 | ||
| SE7012688A SE374747B (fi) | 1970-09-17 | 1970-09-17 | |
| SE7015720A SE380806B (sv) | 1970-11-20 | 1970-11-20 | Forfarande for framstellning av nya estrar av alfa-aminopenicilliner |
| SE1572070 | 1970-11-20 | ||
| FI258071 | 1971-09-15 | ||
| FI2580/71A FI55203C (fi) | 1970-09-17 | 1971-09-15 | Analogifoerfarande foer framstaellning av estrar av alfa-aminopenicilliner |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI791386A7 FI791386A7 (fi) | 1979-04-27 |
| FI59103B FI59103B (fi) | 1981-02-27 |
| FI59103C true FI59103C (fi) | 1981-06-10 |
Family
ID=26655897
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2580/71A FI55203C (fi) | 1970-09-17 | 1971-09-15 | Analogifoerfarande foer framstaellning av estrar av alfa-aminopenicilliner |
| FI3814/74A FI59600C (fi) | 1970-09-17 | 1974-12-31 | Mellanprodukt foer framstaellning av alfa-aminopenicillinestrar |
| FI773032A FI57951C (fi) | 1970-09-17 | 1977-10-13 | Mellanprodukter till anvaendning vid framstaellning av estrar av alfa-aminopenicilliner |
| FI791386A FI59103C (fi) | 1970-09-17 | 1979-04-27 | Mellanprodukter till anvaendning vid framstaellning av alfa-aminopenicillinestrar |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2580/71A FI55203C (fi) | 1970-09-17 | 1971-09-15 | Analogifoerfarande foer framstaellning av estrar av alfa-aminopenicilliner |
| FI3814/74A FI59600C (fi) | 1970-09-17 | 1974-12-31 | Mellanprodukt foer framstaellning av alfa-aminopenicillinestrar |
| FI773032A FI57951C (fi) | 1970-09-17 | 1977-10-13 | Mellanprodukter till anvaendning vid framstaellning av estrar av alfa-aminopenicilliner |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US3873521A (fi) |
| JP (2) | JPS5317597B1 (fi) |
| AR (2) | AR201730A1 (fi) |
| AT (2) | AT309681B (fi) |
| BE (1) | BE772723A (fi) |
| BR (1) | BR7106116D0 (fi) |
| CA (2) | CA960211A (fi) |
| CH (5) | CH577513A5 (fi) |
| CS (2) | CS187312B2 (fi) |
| DD (1) | DD94815A5 (fi) |
| DK (6) | DK132759C (fi) |
| ES (3) | ES395145A1 (fi) |
| FI (4) | FI55203C (fi) |
| FR (1) | FR2106578B1 (fi) |
| GB (1) | GB1363506A (fi) |
| HU (1) | HU165868B (fi) |
| IE (1) | IE35642B1 (fi) |
| IT (1) | IT1049876B (fi) |
| NL (3) | NL164860C (fi) |
| NO (4) | NO140931C (fi) |
| SU (2) | SU553936A3 (fi) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1425933A (en) * | 1972-03-13 | 1976-02-25 | Astra Laekemedel Ab | Cephalosporins |
| US4089963A (en) * | 1972-03-13 | 1978-05-16 | Astra Pharmaceutical Products, Inc. | Esters of amidinopenicillanic acids, pharmaceutical preparations and method for treating infectious diseases |
| GB1426869A (en) * | 1972-03-13 | 1976-03-03 | Astra Laekemedel Ab | Penicillins |
| GB1437088A (en) * | 1972-05-25 | 1976-05-26 | Beecham Group Ltd | Esters of penicillins and cephalosporins |
| NL7401782A (fi) * | 1973-02-14 | 1974-08-16 | ||
| GB1550359A (en) * | 1975-08-07 | 1979-08-15 | Beecham Group Ltd | Antibiotic compositions for oral administration |
| US4247461A (en) * | 1979-11-16 | 1981-01-27 | Bristol-Myers Company | Esterification process using methoxymethyl-P-toluenesulfonate |
| US4340539A (en) * | 1980-01-21 | 1982-07-20 | Bristol-Myers Company | Derivatives of 6-bromo penicillanic acid |
| CA1212105A (en) | 1980-04-30 | 1986-09-30 | Shoji Ikeda | Ampicillin esters and production thereof |
| FR2482587A1 (fr) * | 1980-05-14 | 1981-11-20 | Poudres & Explosifs Ste Nale | Procede de synthese de chloroformiates a-chlores et nouveaux chloroformiates a-chlores |
| US4321253A (en) * | 1980-08-22 | 1982-03-23 | Beatty Morgan L | Suspension of microencapsulated bacampicillin acid addition salt for oral, especially pediatric, administration |
| US4479947A (en) * | 1981-07-13 | 1984-10-30 | Merck & Co., Inc. | Oral absorption enhancement of carboxylic acid pharmaceuticals using (5-alkyl-2-oxo-1,3-dioxolen-4-yl)methyl ester group |
| CA1202617A (en) * | 1982-03-19 | 1986-04-01 | Norman B. Jones | Bacampicillin napsylate |
| IT1190897B (it) * | 1982-06-29 | 1988-02-24 | Opos Biochimica Srl | Procedimento per la preparazione dell'estere 1-etossicarbonilossietilico dell'acido 6-(d(-)-alfa aminoalfa fenilacetamido)-penicillanico |
| FR2532933B1 (fr) * | 1982-06-29 | 1987-11-13 | Astra Laekemedel Ab | Perfectionnements apportes a la preparation d'antibiotiques |
| GB2123821B (en) * | 1982-06-29 | 1987-04-23 | Astra Laekemedel Ab | At-halogeno diethyl carbonates and their use in the preparation of antibiotics |
| IL68992A (en) * | 1982-06-29 | 1991-06-10 | Astra Laekemedel Ab | Alpha-bromo diethyl carbonate and process for the preparation of ethoxycarbonyloxy esters of penicillanic acids |
| JPS5927900A (ja) * | 1982-08-09 | 1984-02-14 | Wakunaga Seiyaku Kk | 固定化オリゴヌクレオチド |
| US4426391A (en) | 1982-09-15 | 1984-01-17 | Merck & Co., Inc. | [(Alkoxycarbonyl)oxy]alkyl esters of methyldopa |
| US4606865A (en) * | 1982-09-20 | 1986-08-19 | Astra Lakemedel Aktiebolag | Methods for the preparation of α-bromodiethylcarbonate |
| DK149079C (da) * | 1982-10-06 | 1986-06-23 | Novo Industri As | Fremgangsmaade til fremstilling af et immobiliseret enzympraeparat |
| IL67637A0 (en) * | 1983-01-07 | 1983-05-15 | Orvet Bv | Preparation of 1'-ethoxycarbonyl-oxyethyl esters of penicillins and novel intermediates |
| IL67177A (en) * | 1982-11-04 | 1985-08-30 | Orvet Bv | 1-bromoethyl ethyl carbonate,methods for its preparation and 1-bromoethylchloroformate and 1-bromoethylbromoformate obtained as intermediates |
| IL67445A (en) * | 1982-12-09 | 1985-11-29 | Teva Pharma | Ethoxycarbonyloxy ethyl esters of non-steroidal anti-inflammatory carboxylic acids |
| FR2551058B1 (fr) * | 1983-08-26 | 1986-09-26 | Poudres & Explosifs Ste Nale | Procede de preparation de chloroformiates a-chlores |
| SE8405611D0 (sv) * | 1984-11-09 | 1984-11-09 | Astra Laekemedel Ab | Process for stabilization of bacampicillin hydrochloride |
| US4855455A (en) * | 1988-01-22 | 1989-08-08 | W. R. Grace & Co.-Conn. | Preparation of amino acid derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1021654A (fr) * | 1949-07-07 | 1953-02-23 | Lphivens Kemiske Fabrik Ved A | Procédé de production d'éthers-sels aminés de pénicilline et de composés qui s'y rattachent |
| GB1241844A (en) * | 1968-08-23 | 1971-08-04 | Beecham Group Ltd | Penicillins |
| US3697507A (en) * | 1968-09-26 | 1972-10-10 | Leo Pharm Prod Ltd | Esters of {60 -aminobenzylpenicillin |
| US3660575A (en) * | 1968-09-26 | 1972-05-02 | Leo Pharm Prod Ltd | Esters of alpha-aminobenzylpenicillin in dosage unit form |
-
1971
- 1971-09-07 US US178426A patent/US3873521A/en not_active Expired - Lifetime
- 1971-09-14 AT AT795771A patent/AT309681B/de not_active IP Right Cessation
- 1971-09-14 FR FR7133107A patent/FR2106578B1/fr not_active Expired
- 1971-09-14 SU SU1696133A patent/SU553936A3/ru active
- 1971-09-14 AT AT537872A patent/AT311557B/de not_active IP Right Cessation
- 1971-09-15 FI FI2580/71A patent/FI55203C/fi active
- 1971-09-15 IT IT28678/71A patent/IT1049876B/it active
- 1971-09-15 IE IE1167/71A patent/IE35642B1/xx unknown
- 1971-09-15 CA CA122,881A patent/CA960211A/en not_active Expired
- 1971-09-15 GB GB4309071A patent/GB1363506A/en not_active Expired
- 1971-09-16 DK DK453871A patent/DK132759C/da not_active IP Right Cessation
- 1971-09-16 CH CH859975A patent/CH577513A5/xx not_active IP Right Cessation
- 1971-09-16 CS CS716617A patent/CS187312B2/cs unknown
- 1971-09-16 CH CH860075A patent/CH589654A5/xx not_active IP Right Cessation
- 1971-09-16 CH CH1362371A patent/CH583239A5/xx not_active IP Right Cessation
- 1971-09-16 HU HUAA684A patent/HU165868B/hu unknown
- 1971-09-16 ES ES195145A patent/ES395145A1/es not_active Expired
- 1971-09-16 BR BR6116/71A patent/BR7106116D0/pt unknown
- 1971-09-16 CS CS71442A patent/CS187316B2/cs unknown
- 1971-09-16 NO NO3449/71A patent/NO140931C/no unknown
- 1971-09-17 DD DD157795A patent/DD94815A5/xx unknown
- 1971-09-17 JP JP7184971A patent/JPS5317597B1/ja active Pending
- 1971-09-17 BE BE772723A patent/BE772723A/xx not_active IP Right Cessation
- 1971-09-17 NL NL7112789.A patent/NL164860C/xx not_active IP Right Cessation
-
1972
- 1972-01-31 NO NO236/72A patent/NO140930C/no unknown
- 1972-04-12 AR AR241427A patent/AR201730A1/es active
- 1972-04-14 ES ES401745A patent/ES401745A1/es not_active Expired
-
1973
- 1973-03-08 US US05/339,364 patent/US3939270A/en not_active Expired - Lifetime
- 1973-03-27 SU SU731899287A patent/SU1153830A3/ru active
- 1973-10-25 CA CA184,183A patent/CA1008447A/en not_active Expired
-
1974
- 1974-09-27 DK DK509674A patent/DK150200C/da not_active IP Right Cessation
- 1974-09-27 DK DK509774A patent/DK509774A/da unknown
- 1974-12-19 NO NO74744606A patent/NO142670C/no unknown
- 1974-12-31 FI FI3814/74A patent/FI59600C/fi active
-
1975
- 1975-01-08 ES ES433637A patent/ES433637A1/es not_active Expired
- 1975-04-08 AR AR258235A patent/AR210991A1/es active
- 1975-06-24 JP JP7921675A patent/JPS5537996B2/ja not_active Expired
- 1975-08-20 DK DK375975A patent/DK375975A/da unknown
-
1976
- 1976-04-20 CH CH493776A patent/CH613207A5/xx not_active IP Right Cessation
-
1977
- 1977-09-21 CH CH1155377A patent/CH602745A5/xx not_active IP Right Cessation
- 1977-10-13 FI FI773032A patent/FI57951C/fi not_active IP Right Cessation
-
1978
- 1978-01-31 NL NL7801086A patent/NL7801086A/xx active Search and Examination
- 1978-12-08 NO NO784144A patent/NO142671C/no unknown
-
1979
- 1979-04-27 FI FI791386A patent/FI59103C/fi not_active IP Right Cessation
-
1980
- 1980-03-17 NL NLAANVRAGE8001563,A patent/NL171160C/xx not_active IP Right Cessation
- 1980-03-27 DK DK133380A patent/DK150201C/da not_active IP Right Cessation
-
1982
- 1982-04-07 DK DK163482A patent/DK158519C/da not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: ASTRA LAEKEMEDEL AB |