NO123386B - - Google Patents
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- Publication number
- NO123386B NO123386B NO70868A NO70868A NO123386B NO 123386 B NO123386 B NO 123386B NO 70868 A NO70868 A NO 70868A NO 70868 A NO70868 A NO 70868A NO 123386 B NO123386 B NO 123386B
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- carbon atoms
- indole
- formula
- hydroxyl
- Prior art date
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- -1 amino, hydroxyl Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
- HHVVFSZNIUHMEJ-UHFFFAOYSA-N 2-(1-benzoyl-5-methoxy-2-methylindol-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=CC=C1 HHVVFSZNIUHMEJ-UHFFFAOYSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical class C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939467A GB1200483A (en) | 1967-02-28 | 1967-02-28 | Method and intermediates for producing indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123386B true NO123386B (nl) | 1971-11-08 |
Family
ID=9871139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO70868A NO123386B (nl) | 1967-02-28 | 1968-02-27 |
Country Status (11)
| Country | Link |
|---|---|
| AT (2) | AT287689B (nl) |
| BE (1) | BE711306A (nl) |
| CH (1) | CH507237A (nl) |
| DE (1) | DE1670031A1 (nl) |
| ES (1) | ES351012A1 (nl) |
| FR (2) | FR1555227A (nl) |
| GB (1) | GB1200483A (nl) |
| IL (1) | IL29502A (nl) |
| NL (1) | NL6802698A (nl) |
| NO (1) | NO123386B (nl) |
| SE (1) | SE333732B (nl) |
-
1967
- 1967-02-28 GB GB939467A patent/GB1200483A/en not_active Expired
-
1968
- 1968-02-20 IL IL2950268A patent/IL29502A/xx unknown
- 1968-02-26 BE BE711306D patent/BE711306A/xx unknown
- 1968-02-26 NL NL6802698A patent/NL6802698A/xx unknown
- 1968-02-26 DE DE19681670031 patent/DE1670031A1/de active Pending
- 1968-02-26 SE SE244668A patent/SE333732B/xx unknown
- 1968-02-27 AT AT01410/69A patent/AT287689B/de not_active IP Right Cessation
- 1968-02-27 CH CH278968A patent/CH507237A/de not_active IP Right Cessation
- 1968-02-27 NO NO70868A patent/NO123386B/no unknown
- 1968-02-27 ES ES351012A patent/ES351012A1/es not_active Expired
- 1968-02-27 AT AT188568A patent/AT285597B/de not_active IP Right Cessation
- 1968-02-28 FR FR141585A patent/FR1555227A/fr not_active Expired
- 1968-05-28 FR FR153144A patent/FR7620M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR7620M (nl) | 1970-01-26 |
| FR1555227A (nl) | 1969-01-24 |
| AT285597B (de) | 1970-11-10 |
| SE333732B (nl) | 1971-03-29 |
| IL29502A (en) | 1971-10-20 |
| DE1670031A1 (de) | 1971-02-25 |
| GB1200483A (en) | 1970-07-29 |
| CH507237A (de) | 1971-05-15 |
| ES351012A1 (es) | 1969-05-16 |
| BE711306A (nl) | 1968-07-01 |
| NL6802698A (nl) | 1968-08-29 |
| AT287689B (de) | 1971-02-10 |
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