IE36917B1 - Tetrahydrocarbazoles - Google Patents

Tetrahydrocarbazoles

Info

Publication number
IE36917B1
IE36917B1 IE1134/72A IE113472A IE36917B1 IE 36917 B1 IE36917 B1 IE 36917B1 IE 1134/72 A IE1134/72 A IE 1134/72A IE 113472 A IE113472 A IE 113472A IE 36917 B1 IE36917 B1 IE 36917B1
Authority
IE
Ireland
Prior art keywords
prepared
reacting
difluoro
compound
acid
Prior art date
Application number
IE1134/72A
Other versions
IE36917L (en
Original Assignee
Sterling Drug Inc
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
Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc
Priority to IE123/75A priority Critical patent/IE36918B1/en
Publication of IE36917L publication Critical patent/IE36917L/en
Publication of IE36917B1 publication Critical patent/IE36917B1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
    • A01N45/02—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring having three carbocyclic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

1373311 3 - Amino - 1,2,3,4 - tetrahydrocarbazoles STERLING DRUG Inc 14 Aug 1972 [16 Aug 1971] 37854/72 Heading C2C Novel compounds I in which R is hydrogen or methyl and Q n is 6,7-difluoro or 6,8-difluoro and their acid addition salts are prepared by (1) reacting a phenylhydrazine II in which Q<SP>1</SP> n is a 3,4-difluoro or 2,4-difluorogroup with a 4-(NHR)-cyclohexanone in the presence of an acid, (2) reacting a compound VI in which Y is halogen or the group Z-SO 2 -O- in which Z is an organic radical with an amine HN(R)CH 3 or (3) reducing a compound IX preferably using lithium aluminium hydride. d and l isomers of 3-dimethylamino-6,8-difluoro- 1,2,3,4-tetrahydro-carbazole are isolated. Compounds VI are prepared from the corresponding 3-hydroxy compound by reaction with a sulphonyl chloride (Z-SO 2 -Cl) or hydrogen halide. The 3-hydroxy compound is prepared by hydrolysis of or the corresponding benzoyloxyester which is prepared by reacting 2,4-fluoro or 3,4-fluoro phenyl hydrazine with 4-benzoyloxycyclohexanone. Compound IX is prepared by reacting a 2,4-fluoro or 3,4-difluoro phenyl hydrazine with 4-(R-N-CHO)-cyclohexanone which is prepared by oxidation of N-(4-formyloxy - cyclohexyl) - N - (R) - formamide in acetone with chromic acid/sulphuric acid in water. The formamide is prepared by reacting 4-(NHR)- cyclohexanol with formic acid. Compounds I have anti-psychotic properties and form with an adjuvant or diluent a pharmaceutical composition which may be administered orally or parenterally. [GB1373311A]
IE1134/72A 1971-08-16 1972-08-15 Tetrahydrocarbazoles IE36917B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
IE123/75A IE36918B1 (en) 1971-08-16 1972-08-15 Tetrahydrocarbazoles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US17220671A 1971-08-16 1971-08-16

Publications (2)

Publication Number Publication Date
IE36917L IE36917L (en) 1973-02-16
IE36917B1 true IE36917B1 (en) 1977-03-30

Family

ID=22626762

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1134/72A IE36917B1 (en) 1971-08-16 1972-08-15 Tetrahydrocarbazoles

Country Status (17)

Country Link
JP (1) JPS4829768A (en)
AR (3) AR194129A1 (en)
AT (3) AT323733B (en)
AU (1) AU475251B2 (en)
BE (1) BE787537A (en)
CA (1) CA965794A (en)
CH (3) CH554333A (en)
DE (1) DE2240211A1 (en)
DK (1) DK137897B (en)
ES (1) ES405865A1 (en)
FR (1) FR2150781B1 (en)
GB (1) GB1373311A (en)
IE (1) IE36917B1 (en)
IL (1) IL40122A (en)
NL (1) NL7211102A (en)
SE (1) SE386438B (en)
ZA (1) ZA725557B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5131269B1 (en) * 1971-07-20 1976-09-06
JPS60233208A (en) * 1984-05-01 1985-11-19 松岡　良市 Production of artificial turf constitution
US5100891A (en) * 1991-01-18 1992-03-31 Hoechst-Roussel Pharmaceuticals Inc. Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[B]indoles and related compounds
GB9113802D0 (en) * 1991-06-26 1991-08-14 Smithkline Beecham Plc Medicaments
DE10026646A1 (en) * 2000-05-29 2001-12-06 Merck Patent Gmbh Process for the production of indoles

Also Published As

Publication number Publication date
FR2150781B1 (en) 1976-04-16
BE787537A (en) 1973-02-14
CA965794A (en) 1975-04-08
ES405865A1 (en) 1975-08-01
AR194129A1 (en) 1973-06-22
DK137897C (en) 1978-10-30
AR201107A1 (en) 1975-02-14
CH554334A (en) 1974-09-30
FR2150781A1 (en) 1973-04-13
JPS4829768A (en) 1973-04-19
AT323734B (en) 1975-07-25
IE36917L (en) 1973-02-16
GB1373311A (en) 1974-11-06
CH554332A (en) 1974-09-30
AT323733B (en) 1975-07-25
AR197724A1 (en) 1974-04-30
IL40122A0 (en) 1972-10-29
AU475251B2 (en) 1976-08-19
NL7211102A (en) 1973-02-20
AT317200B (en) 1974-08-12
ZA725557B (en) 1973-05-30
CH554333A (en) 1974-09-30
DK137897B (en) 1978-05-29
IL40122A (en) 1975-03-13
ATA808374A (en) 1975-02-15
AU4559772A (en) 1974-02-21
SE386438B (en) 1976-08-09
DE2240211A1 (en) 1973-02-22

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