IE37780L - Indeno-pyran and indenothiopyran alkylamines - Google Patents
Indeno-pyran and indenothiopyran alkylaminesInfo
- 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
Links
- -1 indenothiopyran alkylamines Chemical class 0.000 title abstract 2
- UCHFDMKGRKDMAZ-UHFFFAOYSA-N indeno[2,1-b]pyran Chemical compound C1=COC2=CC3=CC=CC=C3C2=C1 UCHFDMKGRKDMAZ-UHFFFAOYSA-N 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002469 indenes Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- 229910052727 yttrium Inorganic materials 0.000 abstract 1
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]
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) |
-
1973
- 1973-06-11 IE IE94973A patent/IE37780B1/en unknown
- 1973-06-15 AU AU56989/73A patent/AU474112B2/en not_active Expired
- 1973-06-22 DE DE19732331899 patent/DE2331899A1/en active Pending
- 1973-06-29 FR FR7323948A patent/FR2202690B1/fr not_active Expired
- 1973-07-02 GB GB3135173A patent/GB1414363A/en not_active Expired
- 1973-07-11 JP JP7884873A patent/JPS4970973A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4970973A (en) | 1974-07-09 |
| AU5698973A (en) | 1974-12-19 |
| FR2202690B1 (en) | 1978-07-28 |
| DE2331899A1 (en) | 1974-04-18 |
| AU474112B2 (en) | 1976-07-15 |
| GB1414363A (en) | 1975-11-19 |
| FR2202690A1 (en) | 1974-05-10 |
| IE37780B1 (en) | 1977-10-12 |
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