[go: up one dir, main page]

IE37780B1 - Indeno-pyran and thiopyran derivatives - Google Patents

Indeno-pyran and thiopyran derivatives

Info

Publication number
IE37780B1
IE37780B1 IE94973A IE94973A IE37780B1 IE 37780 B1 IE37780 B1 IE 37780B1 IE 94973 A IE94973 A IE 94973A IE 94973 A IE94973 A IE 94973A IE 37780 B1 IE37780 B1 IE 37780B1
Authority
IE
Ireland
Prior art keywords
alk
general formula
hydrogen atom
compound
indenopyran
Prior art date
Application number
IE94973A
Other versions
IE37780L (en
Original Assignee
Ayerst Mckenna & Harrison
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 US297130A external-priority patent/US3904617A/en
Application filed by Ayerst Mckenna & Harrison filed Critical Ayerst Mckenna & Harrison
Publication of IE37780L publication Critical patent/IE37780L/en
Publication of IE37780B1 publication Critical patent/IE37780B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/38—Alcohols containing six-membered aromatic rings and other rings and having unsaturation outside the aromatic rings
    • 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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyrane Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1414363 Indenopyran- and indenothiopyranalkylamines AYERST McKENNA & HARRISON Ltd 2 July 1973 [12 Oct 1972 (2)] 31351/73 Heading C2C Novel indenopyran- and indenothiopyranalkylamines of the general formula wherein R<SP>1</SP> is a straight chain C 1-6 alkyl or branched chain C 3 or C 4 alkyl group, each of R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> is as R<SP>1</SP> or a hydrogen atom, R<SP>6</SP> is as R<SP>1</SP>, a hydrogen or halogen atom, or a hydroxy, nitro, C 1-4 alkoxy or C 2-6 alkanoyloxy group, R<SP>7</SP> is as R<SP>1</SP> or a hydrogen atom, X is O or S, and Y is -Alk-NR<SP>8</SP>R<SP>9</SP> in which Alk is CR<SP>10</SP>R<SP>11</SP>, CR<SP>10</SP>R<SP>11</SP>CR<SP>12</SP>R<SP>13</SP>, CR<SP>10</SP>R<SP>11</SP>CR<SP>12</SP>R<SP>13</SP>CR<SP>14</SP>- R<SP>15</SP> or CR<SP>10</SP>R<SP>11</SP>CR<SP>12</SP>R<SP>13</SP>CR<SP>14</SP>R<SP>15</SP>CR<SP>16</SP>R<SP>17</SP> (each of R<SP>10</SP>, R<SP>11</SP>, R<SP>12</SP>, R<SP>13</SP>, R<SP>14</SP>, R<SP>15</SP>, R<SP>16</SP> and R<SP>17</SP> is as R<SP>1</SP> or a hydrogen atom) and each of R<SP>8</SP> and R<SP>9</SP> is as R<SP>1</SP> or a hydrogen atom or NR<SP>8</SP>R<SP>9</SP> is pyrrolidino, piperidino, morpholino, piperazino, 4-R<SP>1</SP>-piperazino or 4-(hydroxy-R<SP>1</SP>)-piperazino, and pharmaceutically acceptable acid addition salts thereof are prepared (i) by treating an indene of the general formula wherein X<SP>1</SP> is -OH, -SH, -S-SO 3 Na or -S-SO 3 K, with a compound of the general formula R<SP>1</SP>-CO-Y<SP>1</SP>, wherein Y<SP>1</SP> is (a) -COOR<SP>19</SP> or -Alk<SP>1</SP>-COOR<SP>19</SP>, in which R<SP>19</SP> is as R<SP>1</SP> or a hydrogen atom and Alk<SP>1</SP> is CR<SP>20</SP>R<SP>11</SP>, CR<SP>10</SP>R<SP>11</SP>-CR<SP>12</SP>R<SP>13</SP> or CR<SP>10</SP>R<SP>11</SP>CR<SP>12</SP>R<SP>13</SP>CR<SP>14</SP>R<SP>15</SP>, (b) -CONR<SP>8</SP>R<SP>9</SP> or -Alkl-CONR<SP>8</SP>R<SP>9</SP>, (c) -CH 2 OCOR<SP>20</SP> or -Alk<SP>1</SP>-CH 2 OCOR<SP>20</SP>, in which R<SP>20</SP> is as R<SP>1</SP> or a hydrogen atom, (d) -Alk<SP>2</SP>-L. in which Alk<SP>2</SP> is CR<SP>10</SP>R<SP>11</SP>CHR<SP>12</SP>, CR<SP>10</SP>R<SP>11</SP>CR<SP>12</SP>- R<SP>13</SP>CHR<SP>14</SP> or CR<SP>10</SP>R<SP>11</SP>CR<SP>12</SP>R<SP>13</SP>CR<SP>14</SP>R<SP>15</SP>CHR<SP>16</SP> and L is a halogen atom, (e) -Alk-NR<SP>20</SP>- COR<SP>21</SP>, in which R<SP>21</SP> is a hydrogen atom or C 1-5 alkyl group, (f) -Alk-NO 2 or (g) -Alk- NR<SP>8</SP>R<SP>9</SP>, in the presence of an acid catalyst to form a compound of the general formula and where necessary, transforming this compound (optionally via other compounds of the same general formula) into the desired product by a method known per se. Indenes of the second general formula above wherein X<SP>1</SP> is -SH are prepared by reacting the corresponding compound in which X<SP>1</SP> is -Br with Na 2 S 2 O 3 , heating the resulting thiosulphate (Na salt) with aqueous ethanolic NaOH and reducing the resulting bis-indenylalkyl disulphide with LiAlH 4 . Pharmaceutical compositions having antidepressant activity comprise, as active ingredient, an indenopyran- or indenothiopyranalkyl-amine of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier. [GB1414363A]
IE94973A 1972-10-12 1973-06-11 Indeno-pyran and thiopyran derivatives IE37780B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US29712972A 1972-10-12 1972-10-12
US297130A US3904617A (en) 1972-10-12 1972-10-12 Process for preparing new heterocyclic derivatives

Publications (2)

Publication Number Publication Date
IE37780L IE37780L (en) 1974-04-12
IE37780B1 true IE37780B1 (en) 1977-10-12

Family

ID=26969995

Family Applications (1)

Application Number Title Priority Date Filing Date
IE94973A IE37780B1 (en) 1972-10-12 1973-06-11 Indeno-pyran and thiopyran derivatives

Country Status (6)

Country Link
JP (1) JPS4970973A (en)
AU (1) AU474112B2 (en)
DE (1) DE2331899A1 (en)
FR (1) FR2202690B1 (en)
GB (1) GB1414363A (en)
IE (1) IE37780B1 (en)

Also Published As

Publication number Publication date
GB1414363A (en) 1975-11-19
AU5698973A (en) 1974-12-19
FR2202690A1 (en) 1974-05-10
AU474112B2 (en) 1976-07-15
IE37780L (en) 1974-04-12
DE2331899A1 (en) 1974-04-18
JPS4970973A (en) 1974-07-09
FR2202690B1 (en) 1978-07-28

Similar Documents

Publication Publication Date Title
UA6301A1 (en) Method for producing cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthylamine derivatives or salts thereof
MY103221A (en) Process for the preparation of a thiazepine compound
AU538424B2 (en) Piperazino phenylindane
HUT40101A (en) Process for producing quinolin-carboxylic acid derivatives and pharmaceutical compositions containing them as active agents
HUT37411A (en) Process for the production of 1,5-benzothiazapine-derivatives
ES8703460A1 (en) Aminoacyllabdanes, a process and intermediates for their preparation and their use as medicaments.
ES8802359A1 (en) Derivatives of tetrahydronaphthalene, process and intermediates for their preparation and medicines containing them.
ES8502099A1 (en) Derivatives of dihydrodibenzocycloheptylidene-ethylamine.
MY102081A (en) 1,3-oxazolidine-2-one derivatives and processes for their preparation
IE44742L (en) Indazolyl-(4)-oxy-propanolamines.
IE37780B1 (en) Indeno-pyran and thiopyran derivatives
GB1432660A (en) Piperazine derivatives processes for their preparation and and pharamacueitcal compositions containing them
ES474367A1 (en) New benzo [d] thiazole derivatives, process for their preparation and their therapeutic applications
GB1181469A (en) Novel Benzothiopyrano Indazole Compounds and Means of Producing the Same
DE3665309D1 (en) Novel peptides, compositions containing them and processes for their production
AU7761587A (en) Process
GR860045B (en) Novel piperazine derivatives processes for production thereof and pharmaceutical compositions comprising said compounds as active ingredient
ES470462A1 (en) Imidazole-2-carbamates and process for their production and pharmaceutical compositions containing them.
EP0392015A4 (en) Novel derivatives of physiologically active substance ml-236b and process for their preparation
GB1388146A (en) Hydroxycrotonic acid derivatives
ES468382A1 (en) Diazepine derivatives
MY101746A (en) 1,5-benzothiazepine derivatives, a process for preparing the same, pharmaceutical compositions as well as the use thereof.
ES8506679A2 (en) Piperazine derivative and pharmaceutical composition containing the same
JPS5615291A (en) Oxacephamycin derivative, its preparation, and antibacterial agent consisting mainly of it
GB1179051A (en) Phenethylamino-Propan-2-ones and -Propan-2-Ols