SU508208A3 - Способ получени тиазолиназетидинонов - Google Patents
Способ получени тиазолиназетидиноновInfo
- Publication number
- SU508208A3 SU508208A3 SU1744415A SU1744415A SU508208A3 SU 508208 A3 SU508208 A3 SU 508208A3 SU 1744415 A SU1744415 A SU 1744415A SU 1744415 A SU1744415 A SU 1744415A SU 508208 A3 SU508208 A3 SU 508208A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- group
- benzene
- ethyl acetate
- solution
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- -1 amine compounds Chemical class 0.000 description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 description 5
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229930182555 Penicillin Natural products 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 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 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229940049954 penicillin Drugs 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 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
- NZPDALOXXLVJNM-UHFFFAOYSA-N N=1CCSC=1COC1=CC=CC=C1 Chemical compound N=1CCSC=1COC1=CC=CC=C1 NZPDALOXXLVJNM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001483078 Phyto Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- FJWLWIRHZOHPIY-UHFFFAOYSA-N potassium;hydroiodide Chemical compound [K].I FJWLWIRHZOHPIY-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11239071A | 1971-02-03 | 1971-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU508208A3 true SU508208A3 (ru) | 1976-03-25 |
Family
ID=22343635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1744415A SU508208A3 (ru) | 1971-02-03 | 1972-02-03 | Способ получени тиазолиназетидинонов |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3681380A (OSRAM) |
| AT (1) | AT312599B (OSRAM) |
| AU (1) | AU3817272A (OSRAM) |
| BE (1) | BE778322A (OSRAM) |
| CA (1) | CA986116A (OSRAM) |
| CH (1) | CH536857A (OSRAM) |
| CS (1) | CS178102B2 (OSRAM) |
| DE (1) | DE2205145A1 (OSRAM) |
| ES (1) | ES399424A1 (OSRAM) |
| FR (1) | FR2124439A1 (OSRAM) |
| GB (1) | GB1374487A (OSRAM) |
| HU (1) | HU164226B (OSRAM) |
| IE (1) | IE35990B1 (OSRAM) |
| IL (1) | IL38613A (OSRAM) |
| NL (1) | NL7201445A (OSRAM) |
| PL (1) | PL85159B1 (OSRAM) |
| SU (1) | SU508208A3 (OSRAM) |
| YU (1) | YU21872A (OSRAM) |
| ZA (1) | ZA72349B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1368231A (en) * | 1970-07-31 | 1974-09-25 | Glaxo Lab Ltd | Thio-substituted azetidinones and thiazolino azetidinones |
| GB1368232A (en) * | 1970-07-31 | 1974-09-25 | Glaxo Lab Ltd | Azetidino-thiazolidine compounds |
| GB1368236A (en) * | 1970-11-03 | 1974-09-25 | Glaxo Lab Ltd | Azetidinone derivatives and their preparation |
| US3880872A (en) * | 1971-09-21 | 1975-04-29 | Lilly Co Eli | Process for preparing thiazoline azetidinones |
| JPS5749555B2 (OSRAM) * | 1973-04-04 | 1982-10-22 | ||
| US4282149A (en) * | 1977-03-21 | 1981-08-04 | Massachusetts Institute Of Technology | Carbon and oxygen analogs of penicillin |
| US4392923A (en) * | 1982-08-09 | 1983-07-12 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing thiazolinozetidinone derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS157621B2 (en) * | 1965-09-10 | 1974-09-16 | Robert B Woodward | Method of 7-amino-3-desacetyloxymethyl-3-formylisocephaelospora acid's derivatives making |
| US3422103A (en) * | 1967-08-11 | 1969-01-14 | Glaxo Lab Ltd | 7(aminophenylacetamido)cephalosporanic acids |
-
1971
- 1971-02-03 US US112390A patent/US3681380A/en not_active Expired - Lifetime
-
1972
- 1972-01-18 IE IE71/72A patent/IE35990B1/xx unknown
- 1972-01-18 ZA ZA720349A patent/ZA72349B/xx unknown
- 1972-01-20 BE BE778322A patent/BE778322A/xx unknown
- 1972-01-21 AU AU38172/72A patent/AU3817272A/en not_active Expired
- 1972-01-23 IL IL38613A patent/IL38613A/en unknown
- 1972-01-24 CA CA133,019A patent/CA986116A/en not_active Expired
- 1972-01-26 GB GB371072A patent/GB1374487A/en not_active Expired
- 1972-01-31 YU YU00218/72A patent/YU21872A/xx unknown
- 1972-02-02 CS CS659A patent/CS178102B2/cs unknown
- 1972-02-02 PL PL1972153241A patent/PL85159B1/pl unknown
- 1972-02-02 HU HUEI405A patent/HU164226B/hu unknown
- 1972-02-02 AT AT82472A patent/AT312599B/de not_active IP Right Cessation
- 1972-02-02 ES ES399424A patent/ES399424A1/es not_active Expired
- 1972-02-03 DE DE19722205145 patent/DE2205145A1/de active Pending
- 1972-02-03 FR FR7203629A patent/FR2124439A1/fr not_active Withdrawn
- 1972-02-03 SU SU1744415A patent/SU508208A3/ru active
- 1972-02-03 CH CH157672A patent/CH536857A/fr not_active IP Right Cessation
- 1972-02-03 NL NL7201445A patent/NL7201445A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT312599B (de) | 1974-01-10 |
| BE778322A (fr) | 1972-07-20 |
| US3681380A (en) | 1972-08-01 |
| IE35990B1 (en) | 1976-07-21 |
| IE35990L (en) | 1972-08-03 |
| GB1374487A (en) | 1974-11-20 |
| CS178102B2 (OSRAM) | 1977-08-31 |
| CH536857A (fr) | 1973-05-15 |
| HU164226B (OSRAM) | 1974-01-28 |
| IL38613A0 (en) | 1972-03-28 |
| ES399424A1 (es) | 1974-10-16 |
| NL7201445A (OSRAM) | 1972-08-07 |
| DE2205145A1 (de) | 1972-10-12 |
| FR2124439A1 (OSRAM) | 1972-09-22 |
| AU3817272A (en) | 1973-07-26 |
| IL38613A (en) | 1976-02-29 |
| ZA72349B (en) | 1973-09-26 |
| PL85159B1 (OSRAM) | 1976-04-30 |
| YU21872A (en) | 1980-03-15 |
| CA986116A (en) | 1976-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI63237B (fi) | Foerfarande foer framstaellning av 3-metyl- och 3-hydroxi-7-amino-1-oxacef-3-em-4-oinsyraderivat vilka aer anvaendbara sommellanprodukter vid framstaellning av antibiotika | |
| Miyano et al. | Asymmetric synthesis of axially dissymmetric 1, 1'-binaphthyls via an intramolecular Ullmann coupling reaction of (R)-and (S)-2, 2'-bis (1-bromo-2-naphthylcarbonyloxy)-1, 1'-binaphthyl. | |
| Just et al. | C-Nucleosides and related compounds. XV. The synthesis of D, L-2′-epi-showdomycin and D, L-showdomycin | |
| SU508208A3 (ru) | Способ получени тиазолиназетидинонов | |
| Ziegler et al. | Synthetic studies on the carbomycins (magnamycins): an exception to the enantioselective synthesis of. beta.-alkyl carboxylic acids via chiral oxazolines | |
| NO784299L (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktivt 4-spectinomycylamin | |
| US3799938A (en) | Certain 4-thia-2,6-diazabicyclo(3.2.0)heptane derivatives | |
| US3714156A (en) | Lactam process | |
| JPS5938955B2 (ja) | Ｏ−置換された７β−アミノ−３−セフエム−３−オ−ル−４−カルボン酸化合物の製法 | |
| SU869558A3 (ru) | Способ получени производных азетидинона | |
| JPH0141152B2 (OSRAM) | ||
| Marthas et al. | Synthesis of α‐hydroxy‐β‐lactams | |
| SU1277897A3 (ru) | Способ получени 1,1-диоксо-6-бром(или-6,6-дибром)пеницилланоилоксиметиловых эфиров 6-(2-азидо-2-фенилацетамидо)пенициллановой кислоты | |
| Boons et al. | Novel polyene cyclisation routes to the acyl tetronic acid ionophore tetronasin (ICI M139603) | |
| SU955861A3 (ru) | Способ получени производных стрептоварицина с | |
| US4088656A (en) | Oxoclavams | |
| US3703512A (en) | Isopropenylmercapto-3-alpha-acylamino-azetidin-4-ones | |
| SU1291587A1 (ru) | Способ получени простагландина @ 2 @ или его аналогов | |
| US3711464A (en) | 1-formyl-2-alpha-(2-acyloxy-2-propylmercapto)-3 alpha-n-acyl-aminoazetidin-4-ones and process for their preparation | |
| Caranti et al. | Anionotropic shift of the 3‐substituent in the reaction of 2‐methoxy‐2, 3‐dihydro‐3‐benzofuranols with boron trifluoride | |
| HU182227B (en) | Process for preparing hexitols containing free carboxyl group | |
| US5128489A (en) | Process for production of optically active 2-(tetrahydropyran-2-yloxy)-1-propanol | |
| US4021425A (en) | Process for producing enone intermediates | |
| JPS6225152B2 (OSRAM) | ||
| US3926965A (en) | Phthalimido derivatives and processes |