CH373042A - Verfahren zur Herstellung von neuen Isoindolinderivaten - Google Patents

Verfahren zur Herstellung von neuen Isoindolinderivaten

Info

Publication number: CH373042A
Authority: CH; Switzerland
Prior art keywords: group; molecular weight; low molecular; weight alkyl; formula
Prior art date: 1959-02-27

Application number

CH7015659A

Other languages

German (de)

English (en)

Inventor

Wilfried Dr Graf

Erich Dr Schmid

Willy Dr Stoll

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.)

1959-02-27

Filing date

1959-02-27

Publication date

1963-11-15

1959-02-27 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1959-02-27 Priority to CH7015659A priority Critical patent/CH373042A/de

1959-03-25 Priority to DK110159A priority patent/DK108575C/da

1959-04-16 Priority to ES0248698A priority patent/ES248698A1/es

1959-04-16 Priority to ES0248697A priority patent/ES248697A1/es

1963-11-15 Publication of CH373042A publication Critical patent/CH373042A/de

Links

GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims description 5
238000000034 method Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 3
-1 polymethylene Polymers 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 6
239000000460 chlorine Chemical group 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000007858 starting material Substances 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
JIVPVXMEBJLZRO-UHFFFAOYSA-N chlorthalidone Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
230000029142 excretion Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
229910001415 sodium ion Inorganic materials 0.000 description 2
OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 1
OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
UALKQROXOHJHFG-UHFFFAOYSA-N 1-ethoxy-3-methylbenzene Chemical compound CCOC1=CC=CC(C)=C1 UALKQROXOHJHFG-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
GODRVOJLUXLBQN-UHFFFAOYSA-N 2-chloro-5-(2-ethyl-1-hydroxy-3-oxoisoindol-1-yl)benzenesulfonamide Chemical compound O=C1N(C(C2=CC=CC=C12)(O)C1=CC(=C(C=C1)Cl)S(N)(=O)=O)CC GODRVOJLUXLBQN-UHFFFAOYSA-N 0.000 description 1
VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
GMLYSDVNKBRUSF-UHFFFAOYSA-N CN(C(C1=CC=CC=C11)(C(C=C2)=CC(S(N)(=O)=O)=C2Cl)O)C1=O Chemical compound CN(C(C1=CC=CC=C11)(C(C=C2)=CC(S(N)(=O)=O)=C2Cl)O)C1=O GMLYSDVNKBRUSF-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
JHFBONATAOAZQK-UHFFFAOYSA-N NS(C(C=C(C(C1=CC=CC=C11)(N(C2CCCCC2)C1=O)O)C=C1)=C1Cl)(=O)=O Chemical compound NS(C(C=C(C(C1=CC=CC=C11)(N(C2CCCCC2)C1=O)O)C=C1)=C1Cl)(=O)=O JHFBONATAOAZQK-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000005224 alkoxybenzenes Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
150000005171 halobenzenes Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000005172 methylbenzenes Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Indole Compounds (AREA)

CH7015659A 1959-02-27 1959-02-27 Verfahren zur Herstellung von neuen Isoindolinderivaten CH373042A (de)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CH7015659A CH373042A (de)	1959-02-27	1959-02-27	Verfahren zur Herstellung von neuen Isoindolinderivaten
DK110159A DK108575C (da)	1959-02-27	1959-03-25	Fremgangsmåde til fremstilling af isoindolinderivater.
ES0248698A ES248698A1 (es)	1959-02-27	1959-04-16	Procedimiento para la preparacion de nuevos derivados de isoindolina
ES0248697A ES248697A1 (es)	1959-02-27	1959-04-16	Procedimiento para la preparacion de nuevos derivados de isoindolina

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH7015659A CH373042A (de)	1959-02-27	1959-02-27	Verfahren zur Herstellung von neuen Isoindolinderivaten

Publications (1)

Publication Number	Publication Date
CH373042A true CH373042A (de)	1963-11-15

Family

ID=4530068

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7015659A CH373042A (de)	1959-02-27	1959-02-27	Verfahren zur Herstellung von neuen Isoindolinderivaten

Country Status (3)

Country	Link
CH (1)	CH373042A (da)
DK (1)	DK108575C (da)
ES (2)	ES248697A1 (da)

1959
- 1959-02-27 CH CH7015659A patent/CH373042A/de unknown
- 1959-03-25 DK DK110159A patent/DK108575C/da active
- 1959-04-16 ES ES0248697A patent/ES248697A1/es not_active Expired
- 1959-04-16 ES ES0248698A patent/ES248698A1/es not_active Expired

Also Published As

Publication number	Publication date
ES248697A1 (es)	1959-12-01
ES248698A1 (es)	1959-12-01
DK108575C (da)	1968-01-08

Publication	Publication Date	Title
DE2023425C3 (de)	1979-06-21	Thiazolylessigsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung
CH374699A (de)	1964-01-31	Verfahren zur Herstellung von Disulfamylanilin-Verbindungen
AT211831B (de)	1960-11-10	Verfahren zur Herstellung von neuen Isoindolinderivaten
EP0315138B1 (de)	1993-01-27	Verfahren zur Herstellung von 6-Chorisatosäureanhydrid
DE1768667B2 (de)	1973-08-09	Verfahren zur herstellung von ooder p-dinitrobenzol
CH373041A (de)	1963-11-15	Verfahren zur Herstellung von neuen Isoindolinderivaten
AT234698B (de)	1964-07-10	Verfahren zur Herstellung von 4-Sulfanilamido-2,6-di-nieder-alkoxy-pyrimidinen
AT219039B (de)	1962-01-10	Verfahren zur Herstellung von neuen Isoindolinderivaten
CH373039A (de)	1963-11-15	Verfahren zur Herstellung von neuen Isoindolinderivaten
CH375715A (de)	1964-03-15	Verfahren zur Herstellung von neuen Isoindolinderivaten
CH374671A (de)	1964-01-31	Verfahren zur Herstellung von neuen Isoindolinderivaten
DE2331969C3 (de)	1977-06-08	beta-(3,4,5-Trimethoxyphenyl)-propionltril und Verfahren zu seiner Herstellung
DE2800537C2 (de)	1982-02-18	Verfahren zur Herstellung von 1-Amino-2-alkoxy-5-brom-benzolen
AT206430B (de)	1959-11-25	Verfahren zur Herstellung von Disulfamylanilinverbindungen
AT281856B (de)	1970-06-10	Verfahren zur Herstellung von neuen N1-Benzolsulfonyl-N2-(1,4-thiazano)-harnstoffen
CH374068A (de)	1963-12-31	Verfahren zur Herstellung von neuen Isoindolinderivaten
AT223619B (de)	1962-10-10	Verfahren zur Herstellung von 3,4-Dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
AT203509B (de)	1959-05-25	Verfahren zur Herstellung von neuen, substituierten 3,5-Dioxo-tetrahydro-1,2,6-thiadiazin-1,1-dioxyden
AT206431B (de)	1959-11-25	Verfahren zur Herstellung von Disulfamylanilinverbindungen
DE2011026C (de)	1972-10-26	S-Carboxy-öJ-dimethoxy-1 -thiaisochroman-1,1-dioxide und Verfahren zu ihrer Herstellung
CH372668A (de)	1963-10-31	Verfahren zur Herstellung von neuen Isoindolinen
AT315847B (de)	1974-05-15	Verfahren zur herstellung von 7-chlor-1,3-dihydro-1-methyl-5-phenyl-2h-1,4-benzodiazepin-2-on
CH374070A (de)	1963-12-31	Verfahren zur Herstellung von neuen Isoindolinderivaten
CH374069A (de)	1963-12-31	Verfahren zur Herstellung von neuen Isoindolinderivaten
CH655930A5 (de)	1986-05-30	Verfahren zur herstellung von 3-hydroxybenzdiazepinonen.