DE1670031A1 - Verfahren und Zwischenprodukte zur Herstellung von Indolderivaten - Google Patents
Verfahren und Zwischenprodukte zur Herstellung von IndolderivatenInfo
- Publication number
- DE1670031A1 DE1670031A1 DE19681670031 DE1670031A DE1670031A1 DE 1670031 A1 DE1670031 A1 DE 1670031A1 DE 19681670031 DE19681670031 DE 19681670031 DE 1670031 A DE1670031 A DE 1670031A DE 1670031 A1 DE1670031 A1 DE 1670031A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- hydrogen
- alkyl
- indole
- groups
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 229940054051 antipsychotic indole derivative Drugs 0.000 title claims description 4
- 150000002475 indoles Chemical class 0.000 title claims description 4
- 239000000543 intermediate Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical class C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical class C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 2
- 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
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical class C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- 102100033070 Histone acetyltransferase KAT6B Human genes 0.000 description 1
- 101100019690 Homo sapiens KAT6B gene Proteins 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 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 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 |
|---|---|
| DE1670031A1 true DE1670031A1 (de) | 1971-02-25 |
Family
ID=9871139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681670031 Pending DE1670031A1 (de) | 1967-02-28 | 1968-02-26 | Verfahren und Zwischenprodukte zur Herstellung von Indolderivaten |
Country Status (11)
-
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 SE SE244668A patent/SE333732B/xx unknown
- 1968-02-26 NL NL6802698A patent/NL6802698A/xx unknown
- 1968-02-26 BE BE711306D patent/BE711306A/xx unknown
- 1968-02-26 DE DE19681670031 patent/DE1670031A1/de active Pending
- 1968-02-27 CH CH278968A patent/CH507237A/de not_active IP Right Cessation
- 1968-02-27 AT AT188568A patent/AT285597B/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 AT01410/69A patent/AT287689B/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 (enrdf_load_stackoverflow) | 1970-01-26 |
| AT285597B (de) | 1970-11-10 |
| GB1200483A (en) | 1970-07-29 |
| NL6802698A (enrdf_load_stackoverflow) | 1968-08-29 |
| NO123386B (enrdf_load_stackoverflow) | 1971-11-08 |
| ES351012A1 (es) | 1969-05-16 |
| CH507237A (de) | 1971-05-15 |
| IL29502A (en) | 1971-10-20 |
| AT287689B (de) | 1971-02-10 |
| FR1555227A (enrdf_load_stackoverflow) | 1969-01-24 |
| BE711306A (enrdf_load_stackoverflow) | 1968-07-01 |
| SE333732B (enrdf_load_stackoverflow) | 1971-03-29 |
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