IE34016B1 - New omikron-anilino-phenylethyl alcohols, the production thereof and compositions containing same - Google Patents
New omikron-anilino-phenylethyl alcohols, the production thereof and compositions containing sameInfo
- Publication number
- IE34016B1 IE34016B1 IE212/70A IE21270A IE34016B1 IE 34016 B1 IE34016 B1 IE 34016B1 IE 212/70 A IE212/70 A IE 212/70A IE 21270 A IE21270 A IE 21270A IE 34016 B1 IE34016 B1 IE 34016B1
- Authority
- IE
- Ireland
- Prior art keywords
- yield
- phenyl
- anilino
- prepared
- chloride
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- -1 o-anilino-phenyl Chemical group 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- 238000007142 ring opening reaction Methods 0.000 abstract 2
- ASLOGUFDOLPIMN-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)indole-2,3-dione 1H-indole-2,3-dione Chemical compound C1(=C(C=CC=C1C)C)N1C(C(C2=CC=CC=C12)=O)=O.N1C(C(C2=CC=CC=C12)=O)=O ASLOGUFDOLPIMN-UHFFFAOYSA-N 0.000 abstract 1
- SQIUEWNROMQRQY-UHFFFAOYSA-N 2,6-dimethyl-n-phenylaniline Chemical group CC1=CC=CC(C)=C1NC1=CC=CC=C1 SQIUEWNROMQRQY-UHFFFAOYSA-N 0.000 abstract 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 abstract 1
- ZKYWDEUSHBRHBI-UHFFFAOYSA-N 2-(2,6-dimethylanilino)benzoic acid Chemical compound CC1=CC=CC(C)=C1NC1=CC=CC=C1C(O)=O ZKYWDEUSHBRHBI-UHFFFAOYSA-N 0.000 abstract 1
- NJFCAWNKWPIBAG-UHFFFAOYSA-N 2-(2-anilinophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1NC1=CC=CC=C1 NJFCAWNKWPIBAG-UHFFFAOYSA-N 0.000 abstract 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- XVAIDCNLVLTVFM-UHFFFAOYSA-N methacetin Chemical compound COC1=CC=C(NC(C)=O)C=C1 XVAIDCNLVLTVFM-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 230000002829 reductive effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
Abstract
1304622 Ortho-anilino-phenethyl alcohols CIBA-GEIGY AG 19 Feb 1970 [20 Feb 1969] 7912/70 Heading C2C Novel compounds of the Formula I wherein R 1 , R 2 and R 3 are independently hydrogen, chlorine, fluorine, bromine, methyl or ethyl and R 1 may additionally be trifluoromethyl and R 4 is hydrogen, chlorine, fluorine, bromine, methyl or methoxy may be prepared by reducing the corresponding o-anilino-phenyl acetic acid or an ester thereof or hydrolysing the corresponding N-acylated compound. The corresponding o-anilino-phenyl acetric acid may be formed by reductive ring opening of an N-phenyl substituted indole-2,3-dione or hydrolytic ring opening of an N-phenylsubstituted-2-indolinone, in which, when present, a substituent corresponding to the R 4 position in I is converted from hydroxy to methoxy. N - Phenyl - 2,61 - dichloroaceto - o - toluidide may be prepared by acetylation of 6-chloro-otoluidine to yield 6<SP>1</SP> - chloroaceto - o - toluidine followed by treatment with bromobenzene in the presence of copper and base to yield 6-chloro-N- phenyl-aceto-o-toluidide which is reacted with chloroacetyl chloride to yield the required compound. Similarly 2 - chloro - N - (2,6 - dichlorophenyl).aceto-p-anisidide may be prepared by reaction of 2<SP>1</SP>,6<SP>1</SP>-dichloroacetanilide with pbromoanisole in the presence of copper and base to yield .N-(2,6-dichlorophenyl)-p-anisidine which is reacted with chloroacetyl chloride to yield the required compound. The intermediate indole-2,3-dione 1-(2,6- xylyl) - indole - 2,3 - dione may be prepared by reaction of o-chlorobenzoic acid with 2,6- xylidine in the presence of base to yield N- (2,6-xylyl)-anthranilic acid which is decarboxylate to yield N-phenyl-2,6-xylidine which with oxalyl chloride yields N.phenyl-2<SP>1</SP>, 6<SP>1</SP>-dimethyl'- oxaniloyl chloride which may be cyclized in the presence of aluminium chloride to the required compound. Pharmaceutical compositions of compounds I show antiphlogistic, analgesic and antipyretic activity when administered orally, parenterally, rectally or topically with the usual excipients.
[GB1304622A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH256169A CH506480A (en) | 1969-02-20 | 1969-02-20 | Process for the production of new, substituted o-anilino-phenethyl alcohols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34016L IE34016L (en) | 1970-08-20 |
| IE34016B1 true IE34016B1 (en) | 1975-01-08 |
Family
ID=4236570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE212/70A IE34016B1 (en) | 1969-02-20 | 1970-02-19 | New omikron-anilino-phenylethyl alcohols, the production thereof and compositions containing same |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5010295B1 (en) |
| AT (1) | AT298465B (en) |
| BE (1) | BE746191A (en) |
| BG (2) | BG17292A3 (en) |
| CA (1) | CA918175A (en) |
| CH (1) | CH506480A (en) |
| CS (2) | CS154657B2 (en) |
| DE (1) | DE2007700C2 (en) |
| DK (1) | DK125241B (en) |
| ES (1) | ES376699A1 (en) |
| FI (1) | FI52571C (en) |
| FR (1) | FR2034558B1 (en) |
| GB (1) | GB1304622A (en) |
| IE (1) | IE34016B1 (en) |
| IL (1) | IL33932A (en) |
| NL (1) | NL168497C (en) |
| NO (1) | NO126572B (en) |
| PL (1) | PL80869B1 (en) |
| SE (1) | SE366540B (en) |
| YU (2) | YU34026B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5254489A (en) * | 1975-10-30 | 1977-05-02 | Kusano Kagaku Kikai Seisakushi | Method of collecting small amoungs of liquid reagent |
| US4496590A (en) * | 1983-04-18 | 1985-01-29 | Sterling Drug Inc. | Benzyl alcohol derivatives, their preparation and use |
| DK335086A (en) * | 1985-08-05 | 1987-02-06 | Michele Testa | CHEMICAL COMPOSITIONS AND PHARMACEUTICAL PREPARATIONS FOR TOPICAL USE CONTAINING AT LEAST ONE OF THE CHEMICAL COMPOSITIONS IN A THERAPEUTIC ACTIVITY |
| CN116217416A (en) * | 2022-12-31 | 2023-06-06 | 黄淮学院 | A kind of preparation method of benzimidazole drug intermediate 3-nitro-4-ethylaminobenzyl alcohol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL133740C (en) * | 1965-04-08 |
-
1969
- 1969-02-20 CH CH256169A patent/CH506480A/en not_active IP Right Cessation
-
1970
- 1970-02-13 SE SE01853/70A patent/SE366540B/xx unknown
- 1970-02-13 DK DK71570AA patent/DK125241B/en not_active IP Right Cessation
- 1970-02-13 FI FI700402A patent/FI52571C/en active
- 1970-02-13 NO NO513/70A patent/NO126572B/no unknown
- 1970-02-13 NL NLAANVRAGE7002097,A patent/NL168497C/en not_active IP Right Cessation
- 1970-02-18 YU YU390/70A patent/YU34026B/en unknown
- 1970-02-19 BE BE746191D patent/BE746191A/en not_active IP Right Cessation
- 1970-02-19 ES ES376699A patent/ES376699A1/en not_active Expired
- 1970-02-19 BG BG014015A patent/BG17292A3/en unknown
- 1970-02-19 IL IL33932A patent/IL33932A/en unknown
- 1970-02-19 CS CS793472*1A patent/CS154657B2/cs unknown
- 1970-02-19 BG BG017648A patent/BG16736A3/en unknown
- 1970-02-19 DE DE2007700A patent/DE2007700C2/en not_active Expired
- 1970-02-19 FR FR707005945A patent/FR2034558B1/fr not_active Expired
- 1970-02-19 CA CA075274A patent/CA918175A/en not_active Expired
- 1970-02-19 JP JP45013881A patent/JPS5010295B1/ja active Pending
- 1970-02-19 AT AT151070A patent/AT298465B/en not_active IP Right Cessation
- 1970-02-19 GB GB791270A patent/GB1304622A/en not_active Expired
- 1970-02-19 CS CS115770A patent/CS154656B2/cs unknown
- 1970-02-19 IE IE212/70A patent/IE34016B1/en unknown
- 1970-02-19 PL PL1970138890A patent/PL80869B1/pl unknown
-
1977
- 1977-05-20 YU YU1267/77A patent/YU34027B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS154657B2 (en) | 1974-04-30 |
| SE366540B (en) | 1974-04-29 |
| JPS5010295B1 (en) | 1975-04-19 |
| DE2007700A1 (en) | 1970-11-19 |
| NL168497C (en) | 1982-04-16 |
| NL168497B (en) | 1981-11-16 |
| FI52571B (en) | 1977-06-30 |
| IE34016L (en) | 1970-08-20 |
| FI52571C (en) | 1977-10-10 |
| FR2034558A1 (en) | 1970-12-11 |
| CS154656B2 (en) | 1974-04-30 |
| YU39070A (en) | 1978-05-15 |
| BG16736A3 (en) | 1973-02-15 |
| YU34026B (en) | 1978-10-31 |
| DE2007700C2 (en) | 1983-04-28 |
| CA918175A (en) | 1973-01-02 |
| BG17292A3 (en) | 1973-07-25 |
| IL33932A0 (en) | 1970-04-20 |
| DK125241B (en) | 1973-01-22 |
| YU126777A (en) | 1978-05-15 |
| NO126572B (en) | 1973-02-26 |
| IL33932A (en) | 1973-05-31 |
| AT298465B (en) | 1972-05-10 |
| CH506480A (en) | 1971-04-30 |
| ES376699A1 (en) | 1972-07-01 |
| PL80869B1 (en) | 1975-08-30 |
| BE746191A (en) | 1970-08-19 |
| GB1304622A (en) | 1973-01-24 |
| YU34027B (en) | 1978-10-31 |
| NL7002097A (en) | 1970-08-24 |
| FR2034558B1 (en) | 1973-07-13 |
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