GB1176348A - Indole Derivatives - Google Patents

Indole Derivatives

Info

Publication number
GB1176348A
GB1176348A GB21268/67A GB2126867A GB1176348A GB 1176348 A GB1176348 A GB 1176348A GB 21268/67 A GB21268/67 A GB 21268/67A GB 2126867 A GB2126867 A GB 2126867A GB 1176348 A GB1176348 A GB 1176348A
Authority
GB
United Kingdom
Prior art keywords
acid
acylated
formula
indolyl
jan
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.)
Expired
Application number
GB21268/67A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
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.)
Filing date
Publication date
Priority claimed from JP4272166A external-priority patent/JPS4913781B1/ja
Priority claimed from JP4272366A external-priority patent/JPS4938260B1/ja
Priority claimed from JP322467A external-priority patent/JPS5140068B1/ja
Priority claimed from JP322367A external-priority patent/JPS5138699B1/ja
Priority claimed from JP353067A external-priority patent/JPS5138700B1/ja
Priority claimed from JP396267A external-priority patent/JPS5138701B1/ja
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of GB1176348A publication Critical patent/GB1176348A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • 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
    • 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
    • C30—CRYSTAL GROWTH
    • C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B19/00—Liquid-phase epitaxial-layer growth
    • C30B19/02—Liquid-phase epitaxial-layer growth using molten solvents, e.g. flux
    • C30B19/04—Liquid-phase epitaxial-layer growth using molten solvents, e.g. flux the solvent being a component of the crystal composition
    • C—CHEMISTRY; METALLURGY
    • C30—CRYSTAL GROWTH
    • C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B19/00—Liquid-phase epitaxial-layer growth
    • C30B19/06—Reaction chambers; Boats for supporting the melt; Substrate holders
    • C30B19/061—Tipping system, e.g. by rotation
    • C—CHEMISTRY; METALLURGY
    • C30—CRYSTAL GROWTH
    • C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
    • C30B29/10—Inorganic compounds or compositions
    • C30B29/40—AIIIBV compounds wherein A is B, Al, Ga, In or Tl and B is N, P, As, Sb or Bi
    • C30B29/42—Gallium arsenide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,176,348. 1 - Acyl - 3 - indolyl aliphatic acids and derivatives thereof. SUMITOMO CHEMICAL CO. Ltd. 8 May, 1967 [12 May, 1966; 27 June, 1966; 30 June, 1966 (2); 8 July, 1966 (2); 1 Aug., 1966; 19 Aug., 1966 (2); 15 Dec., 1966; 16 Dec., 1966 (2); 20 Dec., 1966; 6 Jan., 1967 (2); 7 Jan., 1967; 16 Jan., 1967 (2); 17 Jan., 1967 (3); 20 Jan., 1967], No. 21268(67. Heading C2C. Novel 1-acyl-3-indolyl aliphatic acids and derivatives thereof of the formula wherein R<SP>1</SP> is an unsubstituted or C 1-4 alkyl,- C 1-4 alkoxy-, C 1-4 alkylthionitro-, cyano- or halogen-substituted aromatic carbocyclic ring, or an unsubstituted or a methyl-, ethyl- or halogen-substituted 5- or 6-membered heterocyclic ring containing an oxygen, sulphur or nitrogen atom; R<SP>2</SP> and R<SP>3</SP> are independently hydrogen or C 1-3 alkyl; R<SP>4</SP> is hydrogen, or C 2-4 alkoxycarbonyl; R<SP>5</SP> is C 1-4 alkoxy, benzyloxy, tetrahydropyranyloxy, amino, or hydroxy; R<SP>6</SP> is C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio, nitro, C 2-4 alkenyl, C 2-4 alkenyloxy, halogen or hydrogen; A is an unsubstituted or phenyl- or halogen-substituted, saturated or unsaturated, straight or branched hydrocarbon chain having up to 5 carbon atoms; m and p each are 0 or 1 and n is 0 to 3, are prepared by any of the following methods: (a) by heating a keto-aliphatic acid of the formula R<SP>2</SP>COCH 2 (CHR<SP>3</SP>)m.(CH 2 ) n .(CHR<SP>4</SP>)p- COR<SP>5</SP> with a phenylhydrazine of the p. formula R<SP>6</SP>.C 6 H 4 .N(C=NH-A-R<SP>1</SP>).NH 2 or a N<SP>1</SP>- acylated phenylhydrazine of the formula R<SP>6</SP>.- C 6 H 4 .N(CO.A-R<SP>1</SP>).NH 2 or a N<SP>1</SP>-acylatedphenylhydrazone of the formula R<SP>6</SP>C 6 H 4 .N (CO.A-R<SP>1</SP>)N=B wherein B is an aldehyde or a ketone residue; (b) Compounds wherein R<SP>5</SP> is hydroxy may be prepared by the hydrolysis of the corresponding esters, by thermal decomposition of the corresponding tertiary butyl ester, by hydrogenalysis of the corresponding benzyl ester, or by treating the corresponding amide with nitrous acid in an inert solvent; (c) Compounds wherein m=1, n=1, p=0 and R<SP>5</SP> = hydroxy may be made by: (1) heating the corresponding N<SP>1</SP>-acylated phenylhydrazine or N<SP>1</SP>-acylated phenylhydrazone with an acid of the formula R<SP>2</SP>COCH 2 (CHR<SP>3</SP>) m CH(COOH) 2 ; (2) oxidation of the corresponding indole-3- aldehyde or indole-3-alcohol; (3) dehydrogenation of the corresponding 2,3-dihydroindole derivative; (4) ring closure of R<SP>6</SP>C 6 H 4 .- N(CO-A-R<SP>1</SP>).CH(R<SP>2</SP>).CO.CH(R<SP>3</SP>)COOH, and (d) Compounds wherein m=0, p=0, n=1 and R<SP>5</SP> = OH may be made by: (1) ring closure of the appropriately substituted 3-(2<SP>1</SP>-acylaminophenyl)-levulinic acid; (2) heating the corresponding N<SP>1</SP>-acylated-phenylhydrazine or N<SP>1</SP>- acylate phenyl-hydrazone with either acetosuccinic acid or 2-ketoadipic acid; and (3) dehydration of the corresponding 2-hydro-3- hydroxy-indolylacetic acid or derivative thereof, followed by hydrolysis if required. N<SP>1</SP>-acylated-phenylhydrazines are prepared by reacting the corresponding phenylhydrazines or phenylhydrazones in an inert solvent in the presence of a hydrogen halide with a compound Y-CO-A-R<SP>1</SP> wherein Y is halogen, or by acid hydrolysis of the corresponding N<SP>1</SP>- acylated-phenylhydrazones obtained by reacting the phenylhydrazone in a basic solvent or an inert solvent in the presence of a hydrogen halide accepter with Y-CO-A-R<SP>1</SP>. 1 - Phenylacetyl - 2 - methyl - 5 - methoxy - 3 - indolylacetaldehyde is prepared by hydrolysis of the diethyl-acetal obtained by heating N<SP>1</SP>- phenylacetyl - N<SP>1</SP> - (p - methoxyphenyl)- hydrazinehydrochloride with levulinic aldehyde diethylacetal. 2 - (1<SP>1</SP> - Cinnamayl - 2<SP>1</SP>- methyl - 5<SP>1</SP> - methoxy- 3<SP>1</SP> - indolyl) - ethanol and 2 - (1<SP>1</SP> -phenylacetyl- 2<SP>1</SP> - methyl - 5<SP>1</SP>- methoxy - 3<SP>1</SP> - indolyl) - ethanol are made by heating the corresponding N<SP>1</SP>- acylated-phenlhydrazine hydrochloride with 4- oxo-n-pentanol. 4 - {N - (p - methoxyphenyl) - N - cinnamayl}- amino-3-oxovaleric acid is obtained by the hydrolysis of the corresponding t.-butyl ester resulting from the reaction of tert.-butyl-γ- bromo-#-keto-valeriate with N-cinnamoyl-panisidine which is, in turn, prepared from panisidine and cinnamoyl chloride. t. - Butyl - 1 - cinnamoyl - 2 - methyl - 3 - hydroxy - 5 - methoxy - 2,3 - dihydro - 3 - indolyl acetate is made by reacting the corresponding 3-oxo-2,3-dihydro-indole with t.-butyl bromoacetate. Therapeutic compositions having anti-inflammatory, anti-pyretic, and analgesic properties, contain the above novel 1-acetyl-3-indolyl aliphatic acids or derivatives thereof as the active ingredient and at least one or more pharmaceutically acceptable carriers.
GB21268/67A 1966-01-12 1967-05-08 Indole Derivatives Expired GB1176348A (en)

Applications Claiming Priority (28)

Application Number Priority Date Filing Date Title
JP199966 1966-01-12
JP2730166 1966-04-28
JP2730066 1966-04-28
JP2812566 1966-05-02
JP2840066 1966-05-04
JP3030666 1966-05-12
JP4059166 1966-06-21
JP4203966 1966-06-27
JP4272166A JPS4913781B1 (en) 1966-06-30 1966-06-30
JP4272366A JPS4938260B1 (en) 1966-06-30 1966-06-30
JP4472366 1966-07-08
JP4472466 1966-07-08
JP5069166 1966-08-01
JP5467466 1966-08-19
JP5467566 1966-08-19
JP8248066 1966-12-15
JP8265066 1966-12-16
JP8264966 1966-12-16
JP8374866 1966-12-20
JP135167 1967-01-06
JP135267 1967-01-06
JP149967 1967-01-07
JP322467A JPS5140068B1 (en) 1967-01-16 1967-01-16
JP322367A JPS5138699B1 (en) 1967-01-16 1967-01-16
JP353167 1967-01-17
JP353067A JPS5138700B1 (en) 1967-01-17 1967-01-17
JP353267 1967-01-17
JP396267A JPS5138701B1 (en) 1967-01-20 1967-01-20

Publications (1)

Publication Number Publication Date
GB1176348A true GB1176348A (en) 1970-01-01

Family

ID=27586823

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21268/67A Expired GB1176348A (en) 1966-01-12 1967-05-08 Indole Derivatives

Country Status (3)

Country Link
DE (1) DE1695722C3 (en)
GB (1) GB1176348A (en)
NL (1) NL150439B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4603210A (en) * 1983-04-28 1986-07-29 Troponwerke Gmbh & Co. Kg. Preparation process of acemetacin

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4603210A (en) * 1983-04-28 1986-07-29 Troponwerke Gmbh & Co. Kg. Preparation process of acemetacin

Also Published As

Publication number Publication date
DE1695722B2 (en) 1974-05-30
DE1695722C3 (en) 1975-01-16
NL6706666A (en) 1967-11-13
DE1695722A1 (en) 1972-08-10
NL150439B (en) 1976-08-16

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