SU589922A3 - Способ получени карбаматов - Google Patents
Способ получени карбаматовInfo
- Publication number
- SU589922A3 SU589922A3 SU721821346A SU1821346A SU589922A3 SU 589922 A3 SU589922 A3 SU 589922A3 SU 721821346 A SU721821346 A SU 721821346A SU 1821346 A SU1821346 A SU 1821346A SU 589922 A3 SU589922 A3 SU 589922A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- ethyl acetate
- solution
- chloride
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 5
- 150000004657 carbamic acid derivatives Chemical class 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- -1 acyl carbon Chemical compound 0.000 claims 8
- 239000012948 isocyanate Substances 0.000 claims 7
- 150000002513 isocyanates Chemical class 0.000 claims 7
- 239000010410 layer Substances 0.000 claims 7
- 239000000243 solution Substances 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- 229960000583 acetic acid Drugs 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000012044 organic layer Substances 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 2
- QPLJYAKLSCXZSF-UHFFFAOYSA-N 2,2,2-trichloroethyl carbamate Chemical compound NC(=O)OCC(Cl)(Cl)Cl QPLJYAKLSCXZSF-UHFFFAOYSA-N 0.000 claims 2
- IPAQMPGKZBVNFG-UHFFFAOYSA-N 2,2,2-trichloroethyl n-(oxomethylidene)carbamate Chemical compound ClC(Cl)(Cl)COC(=O)N=C=O IPAQMPGKZBVNFG-UHFFFAOYSA-N 0.000 claims 2
- UUPZTFTUZUQRQT-UHFFFAOYSA-N 2-thiophen-2-ylacetamide Chemical class NC(=O)CC1=CC=CS1 UUPZTFTUZUQRQT-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 239000005909 Kieselgur Substances 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 239000012362 glacial acetic acid Substances 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- 239000012047 saturated solution Substances 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 claims 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 claims 1
- CVIJTVPSUNZYMA-UHFFFAOYSA-N 2,2,2-tribromoethyl carbonochloridate Chemical compound ClC(=O)OCC(Br)(Br)Br CVIJTVPSUNZYMA-UHFFFAOYSA-N 0.000 claims 1
- CMGWBMWNLQZVOA-UHFFFAOYSA-N 2,2,2-tribromoethyl n-(oxomethylidene)carbamate Chemical compound BrC(Br)(Br)COC(=O)N=C=O CMGWBMWNLQZVOA-UHFFFAOYSA-N 0.000 claims 1
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 229910052770 Uranium Inorganic materials 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000005083 Zinc sulfide Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003729 cation exchange resin Substances 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 229920001429 chelating resin Polymers 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 125000006003 dichloroethyl group Chemical group 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000008363 phosphate buffer Substances 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17494971A | 1971-08-25 | 1971-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU589922A3 true SU589922A3 (ru) | 1978-01-25 |
Family
ID=22638189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU721821346A SU589922A3 (ru) | 1971-08-25 | 1972-08-16 | Способ получени карбаматов |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5418275B2 (enExample) |
| AT (1) | AT326816B (enExample) |
| CA (1) | CA1010021A (enExample) |
| CH (1) | CH593924A5 (enExample) |
| CS (1) | CS193015B2 (enExample) |
| DD (2) | DD110261A5 (enExample) |
| ES (1) | ES405967A1 (enExample) |
| HU (2) | HU165406B (enExample) |
| NL (1) | NL7210941A (enExample) |
| PL (1) | PL89700B1 (enExample) |
| SU (1) | SU589922A3 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3905963A (en) * | 1972-01-25 | 1975-09-16 | Lilly Co Eli | Process for preparing primary 3-carbamoyloxymethyl cephalosporins |
| JPS5417517B2 (enExample) * | 1974-04-09 | 1979-06-30 | ||
| JPS5162101A (ja) * | 1974-11-28 | 1976-05-29 | Chuji Saito | Tarensoshikisaishubaketsuto nyoru kaiteikobutsusaishuhikiageyo baketsuto oyobi roopuno junkanokurikiko |
| JPS6286293A (ja) * | 1985-10-12 | 1987-04-20 | 益田 善雄 | クラスト鉱床等の連続採取装置 |
-
1972
- 1972-08-10 CH CH1186572A patent/CH593924A5/de not_active IP Right Cessation
- 1972-08-10 NL NL7210941A patent/NL7210941A/xx not_active Application Discontinuation
- 1972-08-15 CA CA149,784A patent/CA1010021A/en not_active Expired
- 1972-08-16 PL PL1972157311A patent/PL89700B1/pl unknown
- 1972-08-16 SU SU721821346A patent/SU589922A3/ru active
- 1972-08-18 ES ES405967A patent/ES405967A1/es not_active Expired
- 1972-08-22 CS CS725794A patent/CS193015B2/cs unknown
- 1972-08-23 AT AT727572A patent/AT326816B/de not_active IP Right Cessation
- 1972-08-24 HU HUME1531A patent/HU165406B/hu unknown
- 1972-08-24 HU HUME1694A patent/HU167805B/hu unknown
- 1972-08-24 DD DD175238*A patent/DD110261A5/xx unknown
- 1972-08-24 DD DD165227A patent/DD102143A5/xx unknown
- 1972-08-25 JP JP8468972A patent/JPS5418275B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES405967A1 (es) | 1977-04-01 |
| ATA727572A (de) | 1975-03-15 |
| PL89700B1 (enExample) | 1976-12-31 |
| DD110261A5 (enExample) | 1974-12-12 |
| CS193015B2 (en) | 1979-09-17 |
| HU165406B (enExample) | 1974-08-28 |
| HU167805B (enExample) | 1975-12-25 |
| JPS5418275B2 (enExample) | 1979-07-06 |
| CH593924A5 (en) | 1977-12-30 |
| CA1010021A (en) | 1977-05-10 |
| JPS4832829A (enExample) | 1973-05-02 |
| NL7210941A (enExample) | 1973-02-27 |
| DD102143A5 (enExample) | 1973-12-05 |
| AT326816B (de) | 1975-12-29 |
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