CA1077960A - Derives d'acides phenylpropioniques - Google Patents

Derives d'acides phenylpropioniques

Info

Publication number: CA1077960A
Authority: CA; Canada
Prior art keywords: acid; reaction; ibuprofen; yield; production
Prior art date: 1977-08-08
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

Application number

CA284,475A

Other languages

English (en)

Inventor

Norio Tokutake

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shionogi and Co Ltd

Original Assignee

Shionogi and Co Ltd

Priority date (The priority date 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 date listed.)

1977-08-08

Filing date

1977-08-08

Publication date

1980-05-20

1977-08-08 Application filed by Shionogi and Co Ltd filed Critical Shionogi and Co Ltd

1977-08-08 Priority to CA284,475A priority Critical patent/CA1077960A/fr

1980-05-20 Application granted granted Critical

1980-05-20 Publication of CA1077960A publication Critical patent/CA1077960A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 7
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 title 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 19
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 16
239000004310 lactic acid Substances 0.000 claims abstract description 10
235000014655 lactic acid Nutrition 0.000 claims abstract description 10
239000003377 acid catalyst Substances 0.000 claims abstract description 7
KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 claims abstract description 6
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 9
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
238000005727 Friedel-Crafts reaction Methods 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 3
QXYOROBKCZWFKK-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyloxypropanoic acid Chemical compound OC(=O)C(C)OS(=O)(=O)C1=CC=C(C)C=C1 QXYOROBKCZWFKK-UHFFFAOYSA-N 0.000 claims description 3
MFUGBGHURFYBPS-UHFFFAOYSA-N 2-(benzenesulfonyloxy)propanoic acid Chemical compound OC(=O)C(C)OS(=O)(=O)C1=CC=CC=C1 MFUGBGHURFYBPS-UHFFFAOYSA-N 0.000 claims description 2
LFMBKSRGQHUJKP-UHFFFAOYSA-N 2-methylsulfonyloxypropanoic acid Chemical compound OC(=O)C(C)OS(C)(=O)=O LFMBKSRGQHUJKP-UHFFFAOYSA-N 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
229960001680 ibuprofen Drugs 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
229960000443 hydrochloric acid Drugs 0.000 description 2
239000002994 raw material Substances 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
PKQKHWNHCKNYSW-UHFFFAOYSA-N (+-)-2-(4'-isobutylphenyl)propionitrile Chemical compound CC(C)CC1=CC=C(C(C)C#N)C=C1 PKQKHWNHCKNYSW-UHFFFAOYSA-N 0.000 description 1
RVQOLTBRWHPYTM-UHFFFAOYSA-N 1-(chloromethyl)-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(CCl)C=C1 RVQOLTBRWHPYTM-UHFFFAOYSA-N 0.000 description 1
KEAGRYYGYWZVPC-UHFFFAOYSA-N 1-[4-(2-methylpropyl)phenyl]ethanone Chemical compound CC(C)CC1=CC=C(C(C)=O)C=C1 KEAGRYYGYWZVPC-UHFFFAOYSA-N 0.000 description 1
TUZRJGVLAFMQEK-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1.CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 TUZRJGVLAFMQEK-UHFFFAOYSA-N 0.000 description 1
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
-1 4-isobutylphenyl magnesium Chemical compound 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003356 anti-rheumatic effect Effects 0.000 description 1
239000003435 antirheumatic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
208000037516 chromosome inversion disease Diseases 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000007789 gas Substances 0.000 description 1
OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 1
229950009183 ibufenac Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
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 description 1
230000008707 rearrangement Effects 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA284,475A 1977-08-08 1977-08-08 Derives d'acides phenylpropioniques Expired CA1077960A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA284,475A CA1077960A (fr)	1977-08-08	1977-08-08	Derives d'acides phenylpropioniques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA284,475A CA1077960A (fr)	1977-08-08	1977-08-08	Derives d'acides phenylpropioniques

Publications (1)

Publication Number	Publication Date
CA1077960A true CA1077960A (fr)	1980-05-20

Family

ID=4109307

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA284,475A Expired CA1077960A (fr)	1977-08-08	1977-08-08	Derives d'acides phenylpropioniques

Country Status (1)

Country	Link
CA (1)	CA1077960A (fr)

1977
- 1977-08-08 CA CA284,475A patent/CA1077960A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-05-20	MKEX	Expiry

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