NO801813L - Mellomprodukt for fremstilling av tienylpenicilliner - Google Patents
Mellomprodukt for fremstilling av tienylpenicillinerInfo
- Publication number
- NO801813L NO801813L NO801813A NO801813A NO801813L NO 801813 L NO801813 L NO 801813L NO 801813 A NO801813 A NO 801813A NO 801813 A NO801813 A NO 801813A NO 801813 L NO801813 L NO 801813L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- acid
- thienylmalonic acid
- thienylmalonic
- salt
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 3
- GCOOGCQWQFRJEK-UHFFFAOYSA-N 2-thiophen-3-ylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)C=1C=CSC=1 GCOOGCQWQFRJEK-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IXPARDAWKXHMNG-UHFFFAOYSA-N 2-cyano-2-thiophen-3-ylacetic acid Chemical compound OC(=O)C(C#N)C=1C=CSC=1 IXPARDAWKXHMNG-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- -1 3-thienylmalonic acid ester Chemical class 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 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
- 229930182555 Penicillin Natural products 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- ILIKLPKKKHGXPJ-UHFFFAOYSA-M sodium;3-oxo-3-thiophen-3-yloxypropanoate Chemical compound [Na+].[O-]C(=O)CC(=O)OC=1C=CSC=1 ILIKLPKKKHGXPJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- GWZCLMWEJWPFFA-UHFFFAOYSA-N 2-thiophen-3-ylacetonitrile Chemical compound N#CCC=1C=CSC=1 GWZCLMWEJWPFFA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- RCNOGGGBSSVMAS-UHFFFAOYSA-N 2-thiophen-3-ylacetic acid Chemical compound OC(=O)CC=1C=CSC=1 RCNOGGGBSSVMAS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CCLRXHIBLRXYGU-UHFFFAOYSA-N thiophen-3-yl 2-cyanoacetate Chemical compound N#CCC(=O)OC=1C=CSC=1 CCLRXHIBLRXYGU-UHFFFAOYSA-N 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 229960004659 ticarcillin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electrical Control Of Air Or Fuel Supplied To Internal-Combustion Engine (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4987579A | 1979-06-19 | 1979-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO801813L true NO801813L (no) | 1980-12-22 |
Family
ID=21962196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801813A NO801813L (no) | 1979-06-19 | 1980-06-18 | Mellomprodukt for fremstilling av tienylpenicilliner |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0021644B1 (es) |
| JP (1) | JPS567777A (es) |
| KR (1) | KR840001187B1 (es) |
| AR (1) | AR226431A1 (es) |
| AT (1) | ATE21898T1 (es) |
| AU (1) | AU531903B2 (es) |
| CA (1) | CA1135271A (es) |
| DE (1) | DE3071737D1 (es) |
| DK (1) | DK257280A (es) |
| ES (1) | ES492557A0 (es) |
| FI (1) | FI801825A (es) |
| GR (1) | GR68728B (es) |
| HU (1) | HU181548B (es) |
| IL (1) | IL60211A0 (es) |
| NO (1) | NO801813L (es) |
| NZ (1) | NZ193889A (es) |
| ZA (1) | ZA803288B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100453913B1 (ko) * | 2000-12-22 | 2004-10-20 | 재단법인 포항산업과학연구원 | 납계 세라믹스의 무전해 니켈 도금 방법 |
| US8225978B2 (en) | 2007-02-01 | 2012-07-24 | Black & Decker Inc. | Multistage solenoid fastening tool with decreased energy consumption and increased driving force |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513140A (en) * | 1947-11-28 | 1950-06-27 | Indiana University Foundation | 3-thienylacetic acid |
| GB1139164A (en) * | 1966-12-05 | 1969-01-08 | Parke Davis & Co | New heterocyclic acetic acid compounds and methods for their production |
| NZ193888A (en) * | 1979-06-19 | 1982-03-30 | Beecham Group Ltd | Preparation of 3-thienylmalonic acid from a 3-thienylcyano-acetate |
-
1980
- 1980-05-30 NZ NZ193889A patent/NZ193889A/xx unknown
- 1980-05-30 AR AR281245A patent/AR226431A1/es active
- 1980-06-02 IL IL60211A patent/IL60211A0/xx unknown
- 1980-06-03 ZA ZA00803288A patent/ZA803288B/xx unknown
- 1980-06-03 GR GR62120A patent/GR68728B/el unknown
- 1980-06-04 AT AT80301854T patent/ATE21898T1/de active
- 1980-06-04 EP EP80301854A patent/EP0021644B1/en not_active Expired
- 1980-06-04 DE DE8080301854T patent/DE3071737D1/de not_active Expired
- 1980-06-06 FI FI801825A patent/FI801825A/fi not_active Application Discontinuation
- 1980-06-16 DK DK257280A patent/DK257280A/da not_active Application Discontinuation
- 1980-06-17 AU AU59340/80A patent/AU531903B2/en not_active Ceased
- 1980-06-18 KR KR1019800002403A patent/KR840001187B1/ko active
- 1980-06-18 NO NO801813A patent/NO801813L/no unknown
- 1980-06-18 ES ES492557A patent/ES492557A0/es active Granted
- 1980-06-18 CA CA000354263A patent/CA1135271A/en not_active Expired
- 1980-06-18 HU HU801513A patent/HU181548B/hu unknown
- 1980-06-19 JP JP8342180A patent/JPS567777A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NZ193889A (en) | 1982-03-30 |
| IL60211A0 (en) | 1980-09-16 |
| JPS567777A (en) | 1981-01-27 |
| ES8105311A1 (es) | 1981-06-01 |
| DE3071737D1 (en) | 1986-10-09 |
| CA1135271A (en) | 1982-11-09 |
| ZA803288B (en) | 1981-08-26 |
| FI801825A (fi) | 1980-12-20 |
| HU181548B (en) | 1983-10-28 |
| AU5934080A (en) | 1981-01-08 |
| ES492557A0 (es) | 1981-06-01 |
| ATE21898T1 (de) | 1986-09-15 |
| KR840001187B1 (ko) | 1984-08-18 |
| KR830002773A (ko) | 1983-05-30 |
| EP0021644A1 (en) | 1981-01-07 |
| EP0021644B1 (en) | 1986-09-03 |
| AR226431A1 (es) | 1982-07-15 |
| DK257280A (da) | 1980-12-20 |
| AU531903B2 (en) | 1983-09-08 |
| GR68728B (es) | 1982-02-10 |
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