CA1175847A - Dicarboxylates d'acetyl-azetidinones - Google Patents

Dicarboxylates d'acetyl-azetidinones

Info

Publication number: CA1175847A
Authority: CA; Canada
Prior art keywords: process according; formula; group; diethyl; compounds
Prior art date: 1982-01-05
Legal status (The legal status 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 status listed.): Expired

Application number

CA000393595A

Other languages

English (en)

Inventor

Karoly Lempert

Gyula Hornyak

Gabor Doleschall

Kalman Harsanyi

Zsuzsanna Visky

Gizella Barta

Gyula Simig

Jozsef Fetter

Jozsef Nyitrai

Karoly Zauer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Richter Gedeon Vegyeszeti Gyar Nyrt

Original Assignee

Richter Gedeon Vegyeszeti Gyar RT

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.)

1982-01-05

Filing date

1982-01-05

Publication date

1984-10-09

1982-01-05 Application filed by Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT

1982-01-05 Priority to CA000393595A priority Critical patent/CA1175847A/fr

1984-10-09 Application granted granted Critical

1984-10-09 Publication of CA1175847A publication Critical patent/CA1175847A/fr

Status Expired legal-status Critical Current

Links

MCMNBVBMYDSDIN-UHFFFAOYSA-N 1-acetylazetidin-2-one Chemical class CC(=O)N1CCC1=O MCMNBVBMYDSDIN-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 45
239000000203 mixture Substances 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims abstract description 10
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
150000001340 alkali metals Chemical class 0.000 claims abstract description 9
239000011541 reaction mixture Substances 0.000 claims abstract description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052794 bromium Inorganic materials 0.000 claims abstract description 8
125000006239 protecting group Chemical group 0.000 claims abstract description 8
150000001412 amines Chemical class 0.000 claims abstract description 6
150000001408 amides Chemical class 0.000 claims abstract description 5
239000000376 reactant Substances 0.000 claims abstract description 5
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims abstract description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
238000000034 method Methods 0.000 claims description 32
-1 2,4-dimethoxy-benzyl group Chemical group 0.000 claims description 16
239000007858 starting material Substances 0.000 claims description 15
239000000126 substance Substances 0.000 claims description 15
239000000047 product Substances 0.000 claims description 10
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
238000001816 cooling Methods 0.000 claims description 8
239000011630 iodine Substances 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
NHKVBPRGGXQNHS-UHFFFAOYSA-N diethyl 2-[(2,4-dimethoxyphenyl)methylamino]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)NCC1=CC=C(OC)C=C1OC NHKVBPRGGXQNHS-UHFFFAOYSA-N 0.000 claims description 3
XUQMFHLTFVJATG-UHFFFAOYSA-N diethyl 3-acetyl-1-benzyl-4-oxoazetidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)C(C(C)=O)C(=O)N1CC1=CC=CC=C1 XUQMFHLTFVJATG-UHFFFAOYSA-N 0.000 claims description 3
XQTNCHRNGXXKJR-UHFFFAOYSA-N diethyl 3-acetyl-4-oxo-1-phenylazetidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)C(C(C)=O)C(=O)N1C1=CC=CC=C1 XQTNCHRNGXXKJR-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 2
HVHMRTNBJYCLFK-UHFFFAOYSA-N diethyl 2-(benzylamino)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)NCC1=CC=CC=C1 HVHMRTNBJYCLFK-UHFFFAOYSA-N 0.000 claims description 2
MQFMPCGPHYGYCD-UHFFFAOYSA-N diethyl 3-acetyl-1-[(2,4-dimethoxyphenyl)methyl]-4-oxoazetidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)C(C(C)=O)C(=O)N1CC1=CC=C(OC)C=C1OC MQFMPCGPHYGYCD-UHFFFAOYSA-N 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
ANPIEVXKLTYCNX-UHFFFAOYSA-N diethyl 3-acetyl-1-(4-methoxyphenyl)-4-oxoazetidine-2,2-dicarboxylate Chemical compound C(C)(=O)C1C(N(C1=O)C1=CC=C(C=C1)OC)(C(=O)OCC)C(=O)OCC ANPIEVXKLTYCNX-UHFFFAOYSA-N 0.000 claims 2
239000007795 chemical reaction product Substances 0.000 claims 1
RUEYBBPBTGHLNO-UHFFFAOYSA-N diethyl 2-anilinopropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)NC1=CC=CC=C1 RUEYBBPBTGHLNO-UHFFFAOYSA-N 0.000 claims 1
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 abstract description 9
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 abstract description 9
230000015572 biosynthetic process Effects 0.000 abstract description 5
238000003786 synthesis reaction Methods 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract description 4
150000002391 heterocyclic compounds Chemical class 0.000 abstract description 3
230000000141 anti-hypoxic effect Effects 0.000 abstract description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
235000013350 formula milk Nutrition 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
229910052739 hydrogen Inorganic materials 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 13
101150041968 CDC13 gene Proteins 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
238000002329 infrared spectrum Methods 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
238000001228 spectrum Methods 0.000 description 10
239000012362 glacial acetic acid Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
229940074995 bromine Drugs 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000005457 ice water Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
GLNMMBFXBXDHEE-UHFFFAOYSA-N diethyl 3-hydroxy-1-(4-methoxyphenyl)-3-methyl-5-oxopyrrolidine-2,2-dicarboxylate Chemical compound COC1=CC=C(C=C1)N1C(C(CC1=O)(C)O)(C(=O)OCC)C(=O)OCC GLNMMBFXBXDHEE-UHFFFAOYSA-N 0.000 description 2
OQOCWBYDQIDGOY-UHFFFAOYSA-N diethyl 3-hydroxy-3-methyl-5-oxo-1-phenylpyrrolidine-2,2-dicarboxylate Chemical compound O=C1CC(O)(C)C(C(=O)OCC)(C(=O)OCC)N1C1=CC=CC=C1 OQOCWBYDQIDGOY-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
229940086542 triethylamine Drugs 0.000 description 2
238000001665 trituration Methods 0.000 description 2
JYJYVGOIXPFHNB-UHFFFAOYSA-N 2-anilinopropanedioic acid Chemical compound OC(=O)C(C(O)=O)NC1=CC=CC=C1 JYJYVGOIXPFHNB-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
IXVBREAMHDMEIF-UHFFFAOYSA-N diethyl 2-[benzyl-[(2,4-dimethoxyphenyl)methyl]amino]propanedioate Chemical compound C=1C=C(OC)C=C(OC)C=1CN(C(C(=O)OCC)C(=O)OCC)CC1=CC=CC=C1 IXVBREAMHDMEIF-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
ISAPGELEXPYRBC-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydro-3ah-di[1,3]dioxolo[5,4-a:5',4'-d]pyran-5-carboxamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)C1C2OC(C)(C)OC2C2OC(C)(C)OC2O1 ISAPGELEXPYRBC-UHFFFAOYSA-N 0.000 description 1
NUNNRGRUURRZRA-UHFFFAOYSA-N n-[(2,4-dimethoxyphenyl)methyl]-1-phenylmethanamine Chemical compound COC1=CC(OC)=CC=C1CNCC1=CC=CC=C1 NUNNRGRUURRZRA-UHFFFAOYSA-N 0.000 description 1
GGKNHMJBXGNDRV-UHFFFAOYSA-N n-[(2,4-dimethoxyphenyl)methyl]-1-phenylmethanamine;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC=C1CNCC1=CC=CC=C1 GGKNHMJBXGNDRV-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
RAAGBAJWHBQWGY-UHFFFAOYSA-N pyrrolidine-2,2-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCN1 RAAGBAJWHBQWGY-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA000393595A 1982-01-05 1982-01-05 Dicarboxylates d'acetyl-azetidinones Expired CA1175847A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000393595A CA1175847A (fr)	1982-01-05	1982-01-05	Dicarboxylates d'acetyl-azetidinones

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000393595A CA1175847A (fr)	1982-01-05	1982-01-05	Dicarboxylates d'acetyl-azetidinones

Publications (1)

Publication Number	Publication Date
CA1175847A true CA1175847A (fr)	1984-10-09

Family

ID=4121753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000393595A Expired CA1175847A (fr)	1982-01-05	1982-01-05	Dicarboxylates d'acetyl-azetidinones

Country Status (1)

Country	Link
CA (1)	CA1175847A (fr)

1982
- 1982-01-05 CA CA000393595A patent/CA1175847A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-10-10	MKEC	Expiry (correction)
2002-01-05	MKEX	Expiry

Publication	Publication Date	Title
KR850000886B1 (ko)	1985-06-26	삼-치환 이미다졸 유도체의 제조방법
KR880001426B1 (ko)	1988-08-08	세팔로스포린 제조용 중간체의 제조방법
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US4435322A (en)	1984-03-06	Heterocyclic compounds containing an alkoxycarbonyl and a substituted methyl group
FI81339C (fi)	1990-10-10	Foerfarande foer framstaellning av pyrrolidinoderivat, mellanprodukt och dess framstaellningsfoerfarande.
CA1140544A (fr)	1983-02-01	4-carbamoyl imidazolium-5-olates, produits anti-tumeurs et immunodepresseurs, composition pharmaceutique qui en renferme, et preparation
JPS63192753A (ja)	1988-08-10	テトラヒドロキノリン誘導体の光学分割法
SU591149A3 (ru)	1978-01-30	Способ получени производных триазолоизохинолина
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EP0105763B1 (fr)	1988-01-20	Composés indoliques, leur préparation et compositions pharmaceutiques les contenant
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US4432901A (en)	1984-02-21	Beta-lactam compounds containing a C-acetal group and process for their preparation
EP0040332B1 (fr)	1986-09-17	Lactames antihypertensifs
US4927968A (en)	1990-05-22	Chemical intermediates and process
US4958030A (en)	1990-09-18	Process for the preparation of 3-phenylpyrrole derivatives
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SU561513A3 (ru)	1977-06-05	Способ получени производных пиперазина или их солей
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