CS199667B2 - Method of producing 2-/4-/3-thenoyl/phenyl/propionic acid - Google Patents
Method of producing 2-/4-/3-thenoyl/phenyl/propionic acid Download PDFInfo
- Publication number
- CS199667B2 CS199667B2 CS771807A CS180777A CS199667B2 CS 199667 B2 CS199667 B2 CS 199667B2 CS 771807 A CS771807 A CS 771807A CS 180777 A CS180777 A CS 180777A CS 199667 B2 CS199667 B2 CS 199667B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- thenoyl
- phenyl
- propionic acid
- ethyl
- temperature
- Prior art date
Links
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims abstract description 9
- 235000019260 propionic acid Nutrition 0.000 title claims abstract description 4
- 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 title claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- -1 3-thenoyl Chemical group 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 abstract description 2
- 230000002744 anti-aggregatory effect Effects 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 210000001772 blood platelet Anatomy 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 abstract 1
- CICCQWCEJQLFAF-UHFFFAOYSA-N 2-[4-(thiophene-3-carbonyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CSC=C1 CICCQWCEJQLFAF-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- REGOCDRDNZNRMC-UHFFFAOYSA-N 3-ethoxy-2-methyl-3-oxopropanoic acid Chemical compound CCOC(=O)C(C)C(O)=O REGOCDRDNZNRMC-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 206010053567 Coagulopathies Diseases 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229960000212 aminophenazone Drugs 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 230000035602 clotting Effects 0.000 description 2
- 229920001436 collagen Polymers 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
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 2
- JESGWURRAFBBPR-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-thiophen-3-ylethanone Chemical compound C1=CC(F)=CC=C1C(=O)CC1=CSC=C1 JESGWURRAFBBPR-UHFFFAOYSA-N 0.000 description 1
- MFSJSVNVUDQHLV-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1.OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 MFSJSVNVUDQHLV-UHFFFAOYSA-N 0.000 description 1
- BNZPXQWIYCIDMF-UHFFFAOYSA-N 4-[dimethylamino(phenyl)methyl]-5-methylpyrazol-3-one Chemical compound CN(C)C(C=1C(N=NC=1C)=O)C1=CC=CC=C1 BNZPXQWIYCIDMF-UHFFFAOYSA-N 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000008533 pain sensitivity Effects 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- XXPDBLUZJRXNNZ-UHFFFAOYSA-N promethazine hydrochloride Chemical compound Cl.C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 XXPDBLUZJRXNNZ-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7608470A FR2345148A1 (fr) | 1976-03-24 | 1976-03-24 | Nouvel acide propionique substitue, preparation et application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199667B2 true CS199667B2 (en) | 1980-07-31 |
Family
ID=9170850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS771807A CS199667B2 (en) | 1976-03-24 | 1977-03-18 | Method of producing 2-/4-/3-thenoyl/phenyl/propionic acid |
Country Status (26)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2030131B (en) * | 1978-09-12 | 1982-12-22 | Taiyo Pharma Ind | Process for producing 2-(4-(2-thienyl-carbonyl) phenyl) propionic acid |
| EP0046337A3 (en) * | 1980-08-20 | 1982-09-15 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
| GB2181728B (en) * | 1985-10-21 | 1990-01-24 | Indian Drugs & Pharma | 4-(3-thienyl)phenylalkanoic acids and derivatives and process for their preparation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1007643A (en) * | 1972-10-24 | 1977-03-29 | Janssen Pharmaceutica Naamloze Vennootschap | Aroyl-substituted phenylacetic acid derivatives |
-
1976
- 1976-03-24 FR FR7608470A patent/FR2345148A1/fr active Granted
-
1977
- 1977-03-11 YU YU00653/77A patent/YU65377A/xx unknown
- 1977-03-15 AT AT176577A patent/AT358026B/de not_active IP Right Cessation
- 1977-03-15 BE BE175792A patent/BE852463A/xx not_active IP Right Cessation
- 1977-03-17 DE DE19772711585 patent/DE2711585A1/de not_active Withdrawn
- 1977-03-18 CS CS771807A patent/CS199667B2/cs unknown
- 1977-03-21 IT IT7721461A patent/IT1115272B/it active
- 1977-03-21 CA CA274,355A patent/CA1102343A/en not_active Expired
- 1977-03-22 IL IL51720A patent/IL51720A0/xx unknown
- 1977-03-22 ZA ZA00771724A patent/ZA771724B/xx unknown
- 1977-03-22 CH CH359977A patent/CH597220A5/xx not_active IP Right Cessation
- 1977-03-23 ES ES457112A patent/ES457112A1/es not_active Expired
- 1977-03-23 GB GB12327/77A patent/GB1517688A/en not_active Expired
- 1977-03-23 HU HU77LI310A patent/HU176990B/hu unknown
- 1977-03-23 NO NO771033A patent/NO771033L/no unknown
- 1977-03-23 IE IE616/77A patent/IE44660B1/en unknown
- 1977-03-23 AU AU23518/77A patent/AU2351877A/en not_active Expired
- 1977-03-23 SU SU772462808A patent/SU657748A3/ru active
- 1977-03-23 DK DK128077A patent/DK128077A/da not_active Application Discontinuation
- 1977-03-23 SE SE7703317A patent/SE7703317L/xx unknown
- 1977-03-23 MX MX775559U patent/MX4565E/es unknown
- 1977-03-24 DD DD7700198055A patent/DD128778A5/xx unknown
- 1977-03-24 JP JP3164377A patent/JPS52139057A/ja active Pending
- 1977-03-24 NL NL7703215A patent/NL7703215A/xx not_active Application Discontinuation
- 1977-03-24 AR AR266969A patent/AR212262A1/es active
- 1977-03-28 OA OA56120A patent/OA06109A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2345148A1 (fr) | 1977-10-21 |
| NL7703215A (nl) | 1977-09-27 |
| ES457112A1 (es) | 1978-03-01 |
| ZA771724B (en) | 1978-02-22 |
| AU2351877A (en) | 1978-09-28 |
| GB1517688A (en) | 1978-07-12 |
| DD128778A5 (de) | 1977-12-07 |
| YU65377A (en) | 1983-01-21 |
| IE44660L (en) | 1977-09-24 |
| CH597220A5 (enrdf_load_stackoverflow) | 1978-03-31 |
| AT358026B (de) | 1980-08-11 |
| OA06109A (fr) | 1981-06-30 |
| AR212262A1 (es) | 1978-06-15 |
| DE2711585A1 (de) | 1977-09-29 |
| SU657748A3 (ru) | 1979-04-15 |
| FR2345148B1 (enrdf_load_stackoverflow) | 1978-10-20 |
| IT1115272B (it) | 1986-02-03 |
| DK128077A (da) | 1977-09-25 |
| MX4565E (es) | 1982-06-17 |
| IL51720A0 (en) | 1977-05-31 |
| CA1102343A (en) | 1981-06-02 |
| IE44660B1 (en) | 1982-02-10 |
| ATA176577A (de) | 1980-01-15 |
| NO771033L (no) | 1977-09-27 |
| BE852463A (fr) | 1977-09-15 |
| HU176990B (hu) | 1981-06-28 |
| JPS52139057A (en) | 1977-11-19 |
| SE7703317L (sv) | 1977-09-25 |
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