NO121048B - - Google Patents

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Info

Publication number: NO121048B
Authority: NO; Norway
Prior art keywords: general formula; ether; solvent; phenylacetic acid; methyl
Prior art date: 1966-10-07

Application number

NO17002567A

Other languages

English (en)

Norwegian (no)

Inventor

K Fitzi

R Pfister

Original Assignee

Geigy Ag J R

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.)

1966-10-07

Filing date

1967-10-06

Publication date

1971-01-11

1967-10-06 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1971-01-11 Publication of NO121048B publication Critical patent/NO121048B/no

Links

RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
-1 o-nitro- phenylacetic acid ester Chemical class 0.000 claims description 4
150000004792 aryl magnesium halides Chemical class 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011877 solvent mixture Substances 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000000243 solution Substances 0.000 description 8
241000700159 Rattus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
210000002683 foot Anatomy 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
230000008961 swelling Effects 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
230000001741 anti-phlogistic effect Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
QMBFJLTXYWWQIQ-UHFFFAOYSA-N 2-[2-(2,3-dimethylanilino)phenyl]acetic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)CC(O)=O)=C1C QMBFJLTXYWWQIQ-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000700198 Cavia Species 0.000 description 1
206010015150 Erythema Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
SWMFAAPTSMVULA-UHFFFAOYSA-N methyl 2-(2-nitrophenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1[N+]([O-])=O SWMFAAPTSMVULA-UHFFFAOYSA-N 0.000 description 1
HGYGJANXKMHORB-UHFFFAOYSA-N methyl 2-[2-(2,3-dimethylanilino)phenyl]acetate Chemical compound COC(CC1=C(C=CC=C1)NC1=C(C(=CC=C1)C)C)=O HGYGJANXKMHORB-UHFFFAOYSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
GETTZEONDQJALK-UHFFFAOYSA-N trifluorotoluene Substances FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids

Landscapes

Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO17002567A 1966-10-07 1967-10-06 NO121048B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1451866A CH466256A (de)	1966-10-07	1966-10-07	Verfahren zur Herstellung von neuen substituierten Phenylessigsäureestern

Publications (1)

Publication Number	Publication Date
NO121048B true NO121048B (de)	1971-01-11

Family

ID=4401499

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO17002567A NO121048B (de)	1966-10-07	1967-10-06

Country Status (9)

Country	Link
AT (1)	AT276358B (de)
BE (1)	BE704821A (de)
CH (1)	CH466256A (de)
DK (1)	DK120027B (de)
ES (1)	ES345832A1 (de)
GB (1)	GB1202377A (de)
GR (1)	GR37761B (de)
NL (2)	NL6713631A (de)
NO (1)	NO121048B (de)

0
- NL NL133741D patent/NL133741C/xx active
1966
- 1966-10-07 CH CH1451866A patent/CH466256A/de unknown
1967
- 1967-10-06 GR GR670137761A patent/GR37761B/el unknown
- 1967-10-06 AT AT910367A patent/AT276358B/de active
- 1967-10-06 BE BE704821D patent/BE704821A/xx unknown
- 1967-10-06 NO NO17002567A patent/NO121048B/no unknown
- 1967-10-06 ES ES345832A patent/ES345832A1/es not_active Expired
- 1967-10-06 NL NL6713631A patent/NL6713631A/xx unknown
- 1967-10-06 GB GB4570267A patent/GB1202377A/en not_active Expired
- 1967-10-06 DK DK497967A patent/DK120027B/da unknown

Also Published As

Publication number	Publication date
NL6713631A (de)	1968-04-08
AT276358B (de)	1969-11-25
ES345832A1 (es)	1968-11-16
CH466256A (de)	1968-12-15
DK120027B (da)	1971-03-29
BE704821A (de)	1968-04-08
GR37761B (el)	1969-07-12
GB1202377A (en)	1970-08-19
NL133741C (de)

Publication	Publication Date	Title
DE2814556C2 (de)	1987-03-12	Substituierte Phenylessigsäurederivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DE2822848A1 (de)	1978-11-30	Mevalonolacton-derivate und verfahren zu deren herstellung
NO170023B (no)	1992-05-25	Analogifremgangsmaate for fremstilling av nye terapeutisk aktive alfa-glucosidaseinhibitorer
DE2353357C2 (de)	1982-04-01	Aroylsubstituierte Phenylessigsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate
CA1053257A (en)	1979-04-24	Anti-inflammatory and analgesic stilbene derivatives
Gilman et al.	1944	The Metalation of 10-Phenylphenothiazine and of 10-Ethylphenothiazine1
US4337353A (en)	1982-06-29	Novel carboxylic acids, benzoyl phenyl alkanoic acids and use thereof
Izzo	1963	The Preparation of 1-Aryl-1, 2-cyclopropanedicarboximides. An Application of Dimethylsulfoxonium Methylide
Burnett et al.	1958	Improved Preparation of 1-Iodo-2, 4-dinitrobenzene
US1969828A (en)	1934-08-14	Sedative compounds
US3651084A (en)	1972-03-21	Substituted phenylalkanoic acids
US3754090A (en)	1973-08-21	Pharmaceutical compositions and methods for substituted phenethyl alcohols and their esters
US3042714A (en)	1962-07-03	4-aryl, 4-alkaryl-5-oxohexanoic acid
US3631069A (en)	1971-12-28	Substituted phenethyl alcohols and their esters
DE2322932A1 (de)	1973-11-22	Verfahren zur herstellung von 2-(6methoxy-2-naphthyl)-propionsaeure
US2338064A (en)	1943-12-28	Derivatives of 2,4-oxazolidinedione
US2895927A (en)	1959-07-21	Synthesis of thyronine compounds
US3257471A (en)	1966-06-21	Ddt derivatives
NO121502B (de)	1971-03-08
NO742801L (de)	1975-03-17
DE2720321A1 (de)	1977-12-01	Neue benzofuran- und benzoxepinderivate
CA1085422A (en)	1980-09-09	Basic benzyloxyalkyl derivatives
DE2343606A1 (de)	1974-03-07	Neue aliphatische aryloxysaeuren
DE2803544A1 (de)	1979-08-02	Neue benzofuran- und benzoxepinderivate
AT276371B (de)	1969-11-25	Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen