CA1057301A - P.isobutyl-hydratropic acid ester with p.acetamido phenol and process for its preparation - Google Patents
P.isobutyl-hydratropic acid ester with p.acetamido phenol and process for its preparationInfo
- Publication number
- CA1057301A CA1057301A CA226,905A CA226905A CA1057301A CA 1057301 A CA1057301 A CA 1057301A CA 226905 A CA226905 A CA 226905A CA 1057301 A CA1057301 A CA 1057301A
- Authority
- CA
- Canada
- Prior art keywords
- isobutyl
- hydratropic acid
- process according
- acetylaminophenol
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 8
- ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 title 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims abstract description 11
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- CJAJEJACWJJIJR-UHFFFAOYSA-N 2-(4-acetamidophenyl)-2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(C=C1)C(C)(C2=CC=C(C=C2)NC(=O)C)C(=O)O CJAJEJACWJJIJR-UHFFFAOYSA-N 0.000 claims abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 2
- 229910006124 SOCl2 Inorganic materials 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 2
- 208000025747 Rheumatic disease Diseases 0.000 abstract description 2
- 206010022000 influenza Diseases 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- RESWMGUDQRRARI-UHFFFAOYSA-N (4-acetamidophenyl) 2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C(=O)OC1=CC=C(NC(C)=O)C=C1 RESWMGUDQRRARI-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- -1 for example POC13 Chemical compound 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT51002/74A IT1045533B (it) | 1974-05-15 | 1974-05-15 | P.isobutil idratropato di 4 acetamido fenile e procedimento per la sua prefarazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057301A true CA1057301A (en) | 1979-06-26 |
Family
ID=11274212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,905A Expired CA1057301A (en) | 1974-05-15 | 1975-05-14 | P.isobutyl-hydratropic acid ester with p.acetamido phenol and process for its preparation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4016197A (enExample) |
| JP (1) | JPS50154218A (enExample) |
| CA (1) | CA1057301A (enExample) |
| DE (1) | DE2521040C3 (enExample) |
| ES (1) | ES437647A1 (enExample) |
| FR (1) | FR2270859B1 (enExample) |
| IT (1) | IT1045533B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4049700A (en) * | 1976-06-17 | 1977-09-20 | The Upjohn Company | Ibuprofen p-hydroxyphenylurea ester |
| IT1064751B (it) * | 1976-07-09 | 1985-02-25 | Acraf | P. isobutil idratropato di guaiacolo |
| GB1594226A (en) * | 1977-11-03 | 1981-07-30 | Sterwin Ag | Pharmacologically-active esters processes for their preparation and pharmaceutical compositions incorporating the pharmacologically-active esters |
| CN102863350B (zh) * | 2011-07-06 | 2015-06-17 | 中国科学院大连化学物理研究所 | 非甾体抗炎镇痛协同前药及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3481972A (en) * | 1966-09-28 | 1969-12-02 | Dow Chemical Co | Substituted hydroxyethyl acid hydrazides |
-
1974
- 1974-05-15 IT IT51002/74A patent/IT1045533B/it active
-
1975
- 1975-05-01 US US05/573,410 patent/US4016197A/en not_active Expired - Lifetime
- 1975-05-01 JP JP50053767A patent/JPS50154218A/ja active Pending
- 1975-05-12 DE DE2521040A patent/DE2521040C3/de not_active Expired
- 1975-05-12 FR FR7514733A patent/FR2270859B1/fr not_active Expired
- 1975-05-13 ES ES437647A patent/ES437647A1/es not_active Expired
- 1975-05-14 CA CA226,905A patent/CA1057301A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES437647A1 (es) | 1977-01-16 |
| DE2521040B2 (de) | 1980-12-18 |
| FR2270859B1 (enExample) | 1978-10-06 |
| IT1045533B (it) | 1980-05-10 |
| US4016197A (en) | 1977-04-05 |
| FR2270859A1 (enExample) | 1975-12-12 |
| DE2521040C3 (de) | 1982-02-04 |
| JPS50154218A (enExample) | 1975-12-12 |
| DE2521040A1 (de) | 1975-11-27 |
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