IE37780L - Indeno-pyran and indenothiopyran alkylamines - Google Patents

Indeno-pyran and indenothiopyran alkylamines

Info

Publication number
IE37780L
IE37780L IE94973A IE94973A IE37780L IE 37780 L IE37780 L IE 37780L IE 94973 A IE94973 A IE 94973A IE 94973 A IE94973 A IE 94973A IE 37780 L IE37780 L IE 37780L
Authority
IE
Ireland
Prior art keywords
alk
general formula
hydrogen atom
compound
indenopyran
Prior art date
Application number
IE94973A
Other versions
IE37780B1 (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)
  • Pyrane Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (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 true IE37780L (en) 1974-04-12
IE37780B1 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
AU5698973A (en) 1974-12-19
GB1414363A (en) 1975-11-19
IE37780B1 (en) 1977-10-12
JPS4970973A (en) 1974-07-09
AU474112B2 (en) 1976-07-15
FR2202690B1 (en) 1978-07-28
DE2331899A1 (en) 1974-04-18
FR2202690A1 (en) 1974-05-10

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