SU727147A3 - Способ получени цефалоспоринов - Google Patents
Способ получени цефалоспоринов Download PDFInfo
- Publication number
- SU727147A3 SU727147A3 SU752133714A SU2133714A SU727147A3 SU 727147 A3 SU727147 A3 SU 727147A3 SU 752133714 A SU752133714 A SU 752133714A SU 2133714 A SU2133714 A SU 2133714A SU 727147 A3 SU727147 A3 SU 727147A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- alkyl
- formula
- residue
- inorganic
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract description 11
- 229930186147 Cephalosporin Natural products 0.000 title abstract description 7
- 229940124587 cephalosporin Drugs 0.000 title abstract description 7
- 150000001780 cephalosporins Chemical class 0.000 title abstract description 7
- -1 cyanomethyl Chemical group 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 239000002585 base Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 150000007529 inorganic bases Chemical class 0.000 abstract description 3
- 150000007530 organic bases Chemical class 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 abstract 1
- 229910004298 SiO 2 Inorganic materials 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- VPEWBHUCZWYJGM-UHFFFAOYSA-N amino-(2-azidoacetyl)oxycarbamic acid Chemical compound C(C(=O)ON(C(=O)O)N)N=[N+]=[N-] VPEWBHUCZWYJGM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052809 inorganic oxide Inorganic materials 0.000 abstract 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 7
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- BWVJONPOFKRJPP-FQNRMIAFSA-N methyl (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@H]2SCC(C)=C(N2C1=O)C(=O)OC)NC(=O)COC1=CC=CC=C1 BWVJONPOFKRJPP-FQNRMIAFSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 description 4
- NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (ne)-n-methoxycarbonyliminocarbamate Chemical compound COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003952 β-lactams Chemical class 0.000 description 2
- 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 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Document Processing Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23070/74A IT1043958B (it) | 1974-05-22 | 1974-05-22 | Procedimento per la preparazione di cefalosporine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU727147A3 true SU727147A3 (ru) | 1980-04-05 |
Family
ID=11203454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752133714A SU727147A3 (ru) | 1974-05-22 | 1975-05-21 | Способ получени цефалоспоринов |
Country Status (16)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1472866A (en) | 1974-06-12 | 1977-05-11 | Farmaceutici Italia | Cephalosporins and intermediates therefor |
| GB1576219A (en) | 1976-12-31 | 1980-10-01 | Connlab Holdings Ltd | Thiazoleneazetidinone derivatives |
| NL7806860A (nl) * | 1977-07-05 | 1979-01-09 | Farmaceutici Italia | Werkwijze voor het bereiden van met nocardicine verwan- te azetidinonen. |
| US4482491A (en) * | 1981-05-01 | 1984-11-13 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Thiazolinoazetidinone derivatives and process for the preparation of the same |
| EP0088488B1 (en) * | 1982-01-22 | 1986-10-01 | Beecham Group Plc | Antibacterial agents, their preparation and use |
-
1974
- 1974-05-22 IT IT23070/74A patent/IT1043958B/it active
-
1975
- 1975-05-16 AT AT376875A patent/AT340047B/de not_active IP Right Cessation
- 1975-05-16 NL NLAANVRAGE7505800,A patent/NL170286C/xx not_active IP Right Cessation
- 1975-05-17 DE DE19752522142 patent/DE2522142A1/de not_active Withdrawn
- 1975-05-20 CA CA227,388A patent/CA1055485A/en not_active Expired
- 1975-05-20 FR FR7515596A patent/FR2279753A1/fr active Granted
- 1975-05-20 SE SE7505751A patent/SE7505751L/xx unknown
- 1975-05-20 ZA ZA00753244A patent/ZA753244B/xx unknown
- 1975-05-20 DK DK220375A patent/DK220375A/da unknown
- 1975-05-20 HU HU75SO00001145A patent/HU171357B/hu unknown
- 1975-05-20 NO NO751781A patent/NO751781L/no unknown
- 1975-05-20 GB GB2841076A patent/GB1472870A/en not_active Expired
- 1975-05-20 JP JP50059355A patent/JPS50160291A/ja active Pending
- 1975-05-20 GB GB2141975A patent/GB1472865A/en not_active Expired
- 1975-05-21 BE BE156546A patent/BE829304A/xx not_active IP Right Cessation
- 1975-05-21 ES ES437842A patent/ES437842A1/es not_active Expired
- 1975-05-21 SU SU752133714A patent/SU727147A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA753244B (en) | 1976-05-26 |
| AU8131975A (en) | 1976-11-25 |
| HU171357B (hu) | 1977-12-28 |
| NL170286B (nl) | 1982-05-17 |
| IT1043958B (it) | 1980-02-29 |
| JPS50160291A (enrdf_load_stackoverflow) | 1975-12-25 |
| AT340047B (de) | 1977-11-25 |
| NL7505800A (nl) | 1975-11-25 |
| FR2279753A1 (fr) | 1976-02-20 |
| DK220375A (da) | 1975-11-23 |
| GB1472865A (en) | 1977-05-11 |
| GB1472870A (en) | 1977-05-11 |
| DE2522142A1 (de) | 1975-12-11 |
| SE7505751L (sv) | 1975-11-24 |
| BE829304A (fr) | 1975-11-21 |
| NL170286C (nl) | 1982-10-18 |
| CA1055485A (en) | 1979-05-29 |
| FR2279753B1 (enrdf_load_stackoverflow) | 1979-03-16 |
| NO751781L (enrdf_load_stackoverflow) | 1975-11-25 |
| ES437842A1 (es) | 1977-01-01 |
| ATA376875A (de) | 1977-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4504658A (en) | Epimerization of malonic acid esters | |
| CS245753B2 (en) | Production method of 7 beta-acylamido-3-cefem-4-carboxyle acids | |
| US3966717A (en) | 7-β-Acylamido-3-carbamoyloxymethylceph-3-em-4-carboxylic acids and salts thereof | |
| EP0005889A1 (en) | Process for the preparation of beta-lactam derivatives, the novel derivatives so obtainable and pharmaceutical compositions containing them | |
| CS195262B2 (en) | Method of producing novel penicillin and cephalosporin derivatives | |
| JP2003506425A (ja) | ナプロキセンのニトロキシアルキルエステルの製造法 | |
| SU676166A3 (ru) | Способ получени цефалоспоринов или их солей | |
| SU727147A3 (ru) | Способ получени цефалоспоринов | |
| US4147863A (en) | 7-D-(-)-mandelamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylic acid | |
| US4935508A (en) | Process for cephem prodrug esters | |
| US5639877A (en) | Intermediates in the synthesis of cephalosporins | |
| US4036835A (en) | Process for preparing cephalosporins | |
| US4584371A (en) | Catalytic process for preparing 3-ester-methyl cephalosporins from desacetyl-7-aminocephalosporanic acid | |
| US4067866A (en) | Process for preparing cephalosporins and certain novel 2β-thiohydrazo-azetidinones as intermediates | |
| KR870000528B1 (ko) | 3-아지도 세팔로스포린의 제조방법 | |
| NO752034L (enrdf_load_stackoverflow) | ||
| US4555578A (en) | Mercaptotetrazolylalkanohydroxamic acids, salts and ester thereof | |
| US4556513A (en) | Process for the production of antibiotic 1-oxadethiacephalosporins, and intermediate | |
| US3936443A (en) | Penicillin antibiotics | |
| EP0635509A2 (en) | Novel cephalosporin antibiotics and processes for preparation thereof | |
| US3991046A (en) | Penicillin antibiotics | |
| KR790001503B1 (ko) | △3-세팔로스포린 에스테르의 제조방법 | |
| EP0081824B1 (en) | Processes for the production of antibiotic 1-oxadethiacephalosporins | |
| US3988325A (en) | 7-Carboxy or 2,2,2-trichloroethoxy carbonyl- cephalosporins | |
| US4115646A (en) | Process for preparing 7-aminocephalosporanic acid derivatives |