GB1050737A - - Google Patents
Info
- Publication number
- GB1050737A GB1050737A GB1050737DA GB1050737A GB 1050737 A GB1050737 A GB 1050737A GB 1050737D A GB1050737D A GB 1050737DA GB 1050737 A GB1050737 A GB 1050737A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aryl
- alkyl
- hydrogen
- indole
- acetic acid
- 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.)
- Active
Links
- -1 alkenyl radical Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003617 indole-3-acetic acid Substances 0.000 abstract 1
- 150000002475 indoles Chemical class 0.000 abstract 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical group CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 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
- C07D209/10—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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
- C07D209/12—Radicals substituted by oxygen atoms
-
- 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
-
- 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
-
- 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
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,050,737. Indole derivatives. MERCK & CO. Inc. Jan. 29, 1964 [Feb. 1, 1963], No. 2068/66. Divided out of 1,050,728. Heading C2C. Indole-3-acetic acid derivatives of the formula wherein R 1 is an aryl, heterocyclic aryl or substituted aryl or heterocyclic aryl group, e.g. pchlorophenyls, R 2 is a hydrogen atom or a C 1-5 alkyl, C 2-5 alkenyl, aryl, aralkyl, alkaryl or substituted alkyl or aryl radical, R 3 is hydrogen or a C 1-5 alkyl or C 2-5 alkenyl radical and R 5 is a hydrogen or halogen atom or a C 1-5 alkyl, C 1-5 alkoxy, e.g. CH 3 O, haloalkyl, nitro, amino, substituted amino, cyano, aminomethyl, alkylsubstituted amino methyl, mercapto, dialkysulphamoyl or benzyl mercapto radical, are made by reacting the corresponding 1-unsub stituted compound with at least two equivalents of sodium hydride in an inert solvent, cooling the mixture below room temperature, adding the acyl halide of a carboxylic acid of the formula R 1 COOH to form the mixed anhydride of the acid R 2 COOH and the 1-R.CO-indole-3- acetic acid and agitating this in a dilute aqueous hydrogen halide at a temperature below ambient. The exemplified product is 1-p-chlorobenzoyl - 2 - methyl - 5 - methoxyindole - 3 - acetic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25564263A | 1963-02-01 | 1963-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1050737A true GB1050737A (en) |
Family
ID=22969254
Family Applications (13)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1050731D Active GB1050731A (en) | 1963-02-01 | ||
| GB1050729D Active GB1050729A (en) | 1963-02-01 | ||
| GB1050740D Active GB1050740A (en) | 1963-02-01 | ||
| GB1050739D Active GB1050739A (en) | 1963-02-01 | ||
| GB1050730D Active GB1050730A (en) | 1963-02-01 | ||
| GB1050736D Active GB1050736A (en) | 1963-02-01 | ||
| GB1050728D Active GB1050728A (en) | 1963-02-01 | ||
| GB1050737D Active GB1050737A (en) | 1963-02-01 | ||
| GB1050732D Active GB1050732A (en) | 1963-02-01 | ||
| GB1050733D Active GB1050733A (en) | 1963-02-01 | ||
| GB1050735D Active GB1050735A (en) | 1963-02-01 | ||
| GB1050734D Active GB1050734A (en) | 1963-02-01 | ||
| GB1050738D Active GB1050738A (en) | 1963-02-01 |
Family Applications Before (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1050731D Active GB1050731A (en) | 1963-02-01 | ||
| GB1050729D Active GB1050729A (en) | 1963-02-01 | ||
| GB1050740D Active GB1050740A (en) | 1963-02-01 | ||
| GB1050739D Active GB1050739A (en) | 1963-02-01 | ||
| GB1050730D Active GB1050730A (en) | 1963-02-01 | ||
| GB1050736D Active GB1050736A (en) | 1963-02-01 | ||
| GB1050728D Active GB1050728A (en) | 1963-02-01 |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1050732D Active GB1050732A (en) | 1963-02-01 | ||
| GB1050733D Active GB1050733A (en) | 1963-02-01 | ||
| GB1050735D Active GB1050735A (en) | 1963-02-01 | ||
| GB1050734D Active GB1050734A (en) | 1963-02-01 | ||
| GB1050738D Active GB1050738A (en) | 1963-02-01 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT277992B (en) |
| BE (1) | BE643268A (en) |
| BR (1) | BR6456479D0 (en) |
| CH (16) | CH457437A (en) |
| DE (16) | DE1695492A1 (en) |
| DK (11) | DK109334C (en) |
| FI (9) | FI46955C (en) |
| FR (1) | FR1559559A (en) |
| GB (13) | GB1050738A (en) |
| NL (1) | NL6400813A (en) |
| SE (12) | SE317975B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU163233B (en) * | 1970-07-31 | 1973-07-28 | ||
| ATE79741T1 (en) * | 1988-06-21 | 1992-09-15 | Rauter Vita Zahnfabrik | DISPERSED CERAMIC COMPOUND. |
| GB9518994D0 (en) * | 1995-09-16 | 1995-11-15 | Agrevo Uk Ltd | Fungicides |
-
0
- GB GB1050731D patent/GB1050731A/en active Active
- GB GB1050729D patent/GB1050729A/en active Active
- GB GB1050740D patent/GB1050740A/en active Active
- GB GB1050739D patent/GB1050739A/en active Active
- GB GB1050730D patent/GB1050730A/en active Active
- GB GB1050736D patent/GB1050736A/en active Active
- GB GB1050728D patent/GB1050728A/en active Active
- GB GB1050737D patent/GB1050737A/en active Active
- GB GB1050732D patent/GB1050732A/en active Active
- GB GB1050733D patent/GB1050733A/en active Active
- GB GB1050735D patent/GB1050735A/en active Active
- GB GB1050734D patent/GB1050734A/en active Active
- GB GB1050738D patent/GB1050738A/en active Active
-
1964
- 1964-01-14 DE DE19641695492 patent/DE1695492A1/en active Pending
- 1964-01-24 DE DE19641770116 patent/DE1770116A1/en active Pending
- 1964-01-24 DE DE19641695490 patent/DE1695490A1/en active Pending
- 1964-01-24 DE DE19641695484 patent/DE1695484A1/en active Pending
- 1964-01-24 DE DE19641695491 patent/DE1695491A1/en active Pending
- 1964-01-24 DE DE19641695493 patent/DE1695493A1/en active Pending
- 1964-01-24 DE DE19641695487 patent/DE1695487A1/en active Pending
- 1964-01-24 DE DE19641470059D patent/DE1470059B1/en active Pending
- 1964-01-24 DE DE19641770134 patent/DE1770134A1/en active Pending
- 1964-01-24 DE DE19641793561 patent/DE1793561A1/en active Pending
- 1964-01-24 DE DE19641695486 patent/DE1695486A1/en active Pending
- 1964-01-24 DE DE19641695489 patent/DE1695489A1/en active Pending
- 1964-01-24 DE DE19641770802 patent/DE1770802A1/en active Pending
- 1964-01-24 DE DE19641695488 patent/DE1695488A1/en active Pending
- 1964-01-24 DE DE19641695485 patent/DE1695485A1/en active Pending
- 1964-01-24 DE DE19641770132 patent/DE1770132A1/en active Pending
- 1964-01-28 BR BR15647964A patent/BR6456479D0/en unknown
- 1964-01-28 AT AT01821/67A patent/AT277992B/en not_active IP Right Cessation
- 1964-01-29 FI FI16964A patent/FI46955C/en active
- 1964-01-31 NL NL6400813A patent/NL6400813A/xx unknown
- 1964-01-31 DK DK598765A patent/DK109334C/en active
- 1964-01-31 CH CH236668A patent/CH457437A/en unknown
- 1964-01-31 CH CH236168A patent/CH464202A/en unknown
- 1964-01-31 DK DK598265A patent/DK109562C/en active
- 1964-01-31 BE BE643268D patent/BE643268A/xx unknown
- 1964-01-31 CH CH1674568A patent/CH466289A/en unknown
- 1964-01-31 CH CH1674768A patent/CH466290A/en unknown
- 1964-01-31 CH CH235868A patent/CH457434A/en unknown
- 1964-01-31 FR FR1559559D patent/FR1559559A/fr not_active Expired
- 1964-01-31 CH CH236368A patent/CH457436A/en unknown
- 1964-01-31 CH CH419468A patent/CH466284A/en unknown
- 1964-01-31 SE SE88967A patent/SE317975B/xx unknown
- 1964-01-31 DK DK48964A patent/DK112238B/en unknown
- 1964-01-31 CH CH490368A patent/CH466287A/en unknown
- 1964-01-31 CH CH236068A patent/CH457435A/en unknown
- 1964-01-31 CH CH490268A patent/CH466286A/en unknown
- 1964-01-31 CH CH236468A patent/CH466283A/en unknown
- 1964-01-31 DK DK598565A patent/DK109514C/en active
- 1964-01-31 CH CH236268A patent/CH557815A/en not_active IP Right Cessation
- 1964-01-31 SE SE89267A patent/SE302463B/xx unknown
- 1964-01-31 CH CH1674468A patent/CH466288A/en unknown
- 1964-01-31 CH CH444166A patent/CH466285A/en unknown
- 1964-01-31 CH CH236568A patent/CH464203A/en unknown
- 1964-01-31 SE SE123764A patent/SE307948B/xx unknown
-
1965
- 1965-11-22 DK DK598365A patent/DK113501B/en unknown
- 1965-11-22 DK DK598465A patent/DK111751B/en unknown
- 1965-11-22 DK DK598865A patent/DK112313B/en unknown
- 1965-11-22 DK DK598665A patent/DK112239B/en unknown
- 1965-11-22 DK DK598965A patent/DK112314B/en unknown
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1966
- 1966-02-23 DK DK93266A patent/DK112446B/en unknown
- 1966-02-23 DK DK93366A patent/DK112447B/en unknown
-
1967
- 1967-01-20 SE SE895/67A patent/SE320069B/xx unknown
- 1967-01-20 SE SE896/67A patent/SE320666B/xx unknown
- 1967-01-20 SE SE890/67A patent/SE307133B/xx unknown
- 1967-01-20 SE SE88667A patent/SE302130B/en unknown
- 1967-01-20 SE SE891/67A patent/SE304995B/xx unknown
- 1967-01-20 SE SE88867A patent/SE302132B/en unknown
- 1967-01-20 SE SE89367A patent/SE302133B/en unknown
- 1967-01-20 SE SE894/67A patent/SE320367B/xx unknown
- 1967-01-31 SE SE88767A patent/SE302131B/xx unknown
- 1967-02-23 CH CH115364A patent/CH489495A/en not_active IP Right Cessation
-
1970
- 1970-09-21 FI FI257570A patent/FI47101C/en active
- 1970-09-21 FI FI257070A patent/FI47097B/fi active
- 1970-09-21 FI FI256870A patent/FI47096C/en active
- 1970-09-21 FI FI257470A patent/FI47100C/en active
- 1970-09-21 FI FI257270A patent/FI47099C/en active
- 1970-09-21 FI FI257370A patent/FI47185C/en active
- 1970-09-21 FI FI257170A patent/FI47098C/en active
- 1970-09-21 FI FI702570A patent/FI47097C/en active
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