CH581106A5 - 1-oxo-2-p-carboxymethylphenyl isoindolines - having analgetic and anti-inflammatory activity - Google Patents

1-oxo-2-p-carboxymethylphenyl isoindolines - having analgetic and anti-inflammatory activity

Info

Publication number: CH581106A5
Authority: CH; Switzerland
Prior art keywords: phenyl; oxo; isoindoline; methyl; compounds
Prior art date: 1971-11-22

Application number

CH1701872A

Other languages

German (de)

English (en)

Original Assignee

Erba Carlo Spa

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.)

1971-11-22

Filing date

1972-11-22

Publication date

1976-10-29

1972-11-22 Application filed by Erba Carlo Spa filed Critical Erba Carlo Spa

1976-10-29 Publication of CH581106A5 publication Critical patent/CH581106A5/de

Links

GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims description 10
230000000202 analgesic effect Effects 0.000 title description 4
230000003110 anti-inflammatory effect Effects 0.000 title description 4
238000006243 chemical reaction Methods 0.000 claims abstract description 8
238000000034 method Methods 0.000 claims abstract description 8
238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
150000001735 carboxylic acids Chemical class 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 2
238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract description 9
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract description 8
229910019020 PtO2 Inorganic materials 0.000 abstract description 4
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 4
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
125000000217 alkyl group Chemical group 0.000 abstract 3
YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical compound NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 abstract 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
235000019439 ethyl acetate Nutrition 0.000 abstract 1
230000007062 hydrolysis Effects 0.000 abstract 1
238000006460 hydrolysis reaction Methods 0.000 abstract 1
ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 abstract 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
-1 p- (benzylidene) -amino-phenyl-acetonitrile Chemical compound 0.000 description 8
238000010992 reflux Methods 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000002904 solvent Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
229910006124 SOCl2 Inorganic materials 0.000 description 3
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
YAVXGZPCODWPJL-UHFFFAOYSA-N 2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1N1C(=O)C2=CC=CC=C2C1 YAVXGZPCODWPJL-UHFFFAOYSA-N 0.000 description 2
DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229940049953 phenylacetate Drugs 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
DVCHUURKGBKKME-UHFFFAOYSA-N 2-[4-(benzylamino)phenyl]acetonitrile Chemical compound C1=CC(CC#N)=CC=C1NCC1=CC=CC=C1 DVCHUURKGBKKME-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000005219 aminonitrile group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
YOOKIEIXJFYJSO-UHFFFAOYSA-N ethyl 2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1N1C(=O)C2=CC=CC=C2C1 YOOKIEIXJFYJSO-UHFFFAOYSA-N 0.000 description 1
STWRUFUDZZDORZ-UHFFFAOYSA-N ethyl 2-[4-(benzylamino)phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1NCC1=CC=CC=C1 STWRUFUDZZDORZ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
FTIZYGAOMCFUIA-UHFFFAOYSA-N methyl 2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1N1C(=O)C2=CC=CC=C2C1 FTIZYGAOMCFUIA-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000725 suspension Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)

CH1701872A 1971-11-22 1972-11-22 1-oxo-2-p-carboxymethylphenyl isoindolines - having analgetic and anti-inflammatory activity CH581106A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT3143471		1971-11-22

Publications (1)

Publication Number	Publication Date
CH581106A5 true CH581106A5 (en)	1976-10-29

Family

ID=11233629

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1701872A CH581106A5 (en)	1971-11-22	1972-11-22	1-oxo-2-p-carboxymethylphenyl isoindolines - having analgetic and anti-inflammatory activity
CH353676A CH581107A5 (cs)	1971-11-22	1972-11-22

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH353676A CH581107A5 (cs)	1971-11-22	1972-11-22

Country Status (8)

Country	Link
JP (1)	JPS5936616B2 (cs)
AT (1)	AT325604B (cs)
CA (1)	CA994785A (cs)
CH (2)	CH581106A5 (cs)
FI (1)	FI53702C (cs)
HU (1)	HU168756B (cs)
NL (1)	NL7215830A (cs)
SE (1)	SE387113B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8110681B2 (en) *	2006-03-17	2012-02-07	The United States Of America As Represented By The Secretary, Department Of Health And Human Services	Compounds for the treatment of spinal muscular atrophy and other uses

1972
- 1972-11-15 FI FI3197/72A patent/FI53702C/fi active
- 1972-11-21 SE SE1509972A patent/SE387113B/xx unknown
- 1972-11-21 HU HUEA000115 patent/HU168756B/hu unknown
- 1972-11-21 CA CA157,062A patent/CA994785A/en not_active Expired
- 1972-11-21 AT AT988772A patent/AT325604B/de not_active IP Right Cessation
- 1972-11-22 JP JP11673172A patent/JPS5936616B2/ja not_active Expired
- 1972-11-22 CH CH1701872A patent/CH581106A5/de not_active IP Right Cessation
- 1972-11-22 CH CH353676A patent/CH581107A5/xx not_active IP Right Cessation
- 1972-11-22 NL NL7215830A patent/NL7215830A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
NL7215830A (cs)	1973-05-24
CA994785A (en)	1976-08-10
CH581107A5 (cs)	1976-10-29
FI53702C (fi)	1978-07-10
SE387113B (sv)	1976-08-30
FI53702B (cs)	1978-03-31
HU168756B (cs)	1976-07-28
JPS4857965A (cs)	1973-08-14
JPS5936616B2 (ja)	1984-09-05
ATA988772A (de)	1975-01-15
AT325604B (de)	1975-10-27

Legal Events

Date	Code	Title	Description
1993-01-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE1720019B2 (de)	1978-01-19	1-benzyl-2-aminoacetyl-pyrrol-derivate, deren salze und verfahren zu ihrer herstellung
DE1618465B2 (de)	1978-09-28	Phenylessigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
AT391866B (de)	1990-12-10	Verfahren zur herstellung neuer s-triazolo (1,5-a) pyrimidine
DE2347015C2 (de)	1985-12-12	Neue Pyrazolyloxyessigsäurederivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel
CH619206A5 (cs)	1980-09-15
CH581106A5 (en)	1976-10-29	1-oxo-2-p-carboxymethylphenyl isoindolines - having analgetic and anti-inflammatory activity
EP0158312B1 (de)	1990-09-12	1-[Cyclohexyl]-3,4-di-[hydro]-isochinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE1695188C3 (de)	1980-12-11	Verfahren zur Herstellung von l-Alkyl^-chlor^-dihydro-S-phenyl-IH-1,4-benzodiazepinen
AT354432B (de)	1980-01-10	Verfahren zur herstellung von 3-indolylessig- saeuren
CH496714A (de)	1970-09-30	Verfahren zur Herstellung von Derivaten des 1,3,4,5-Tetrahydrobenzodiazepins
DE2625163A1 (de)	1976-12-30	Alpha-chlorcarbonsaeuren und verfahren zu ihrer herstellung
AT376417B (de)	1984-11-26	Verfahren zur herstellung von phenylaethanolaminen und ihren salzen
DE1643265C3 (de)	1978-08-31	Kernsubstituierte 2-Aminomethylbenzhydrole, Verfahren zu deren Herstellung und Arzneimittel auf der Basis dieser Verbindungen
AT343649B (de)	1978-06-12	Verfahren zur herstellung neuer substituierter, gegebenenfalls veresterter oder amidierter benzocycloalkenylcarbonsauren
AT269864B (de)	1969-04-10	Verfahren zur Herstellung von neuen Pyrrylaminoketonderivaten und ihren Salzen
AT282629B (de)	1970-07-10	Verfahren zur herstellung neuer zimtsaeureamide
AT228197B (de)	1963-07-10	Verfahren zur Herstellung von neuen Pyrazolon-Derivaten
AT343106B (de)	1978-05-10	Verfahren zur herstellung von neuen aminoalkylestern von indanylcarbonsauren
DE2637596A1 (de)	1977-03-03	3-(5-aryl-2-furyl)-3-hydroxypropionsaeuren und deren aethylester
AT299167B (de)	1972-06-12	Verfahren zur Herstellung der neuen α-[p-(1-Cyclohexenyl)-phenyl]-propionsäure
AT254857B (de)	1967-06-12	Verfahren zur Herstellung von neuen Naphthalinverbindungen
AT343648B (de)	1978-06-12	Verfahren zur herstellung neuer substituierter, gegebenenfalls veresterter oder amidierter benzocycloalkenylcarbonsauren
DE2613838A1 (de)	1976-10-07	Verfahren zum erzeugen der eckige klammer auf o-(2,6-dichloranilino)- phenyl eckige klammer zu -essigsaeure und von salzen derselben
AT337681B (de)	1977-07-11	Verfahren zur herstellung von neuen benzocycloalkencarbonsauren und deren derivaten
AT283365B (de)	1970-08-10	Verfahren zur Herstellung neuer Zimtsäureamide