IE37060L - Indole derivatives - Google Patents

Indole derivatives

Info

Publication number
IE37060L
IE37060L IE1773A IE1773A IE37060L IE 37060 L IE37060 L IE 37060L IE 1773 A IE1773 A IE 1773A IE 1773 A IE1773 A IE 1773A IE 37060 L IE37060 L IE 37060L
Authority
IE
Ireland
Prior art keywords
alkyl
alk
lower alkyl
formula
group
Prior art date
Application number
IE1773A
Other versions
IE37060B1 (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 US00217627A external-priority patent/US3852285A/en
Priority claimed from US297130A external-priority patent/US3904617A/en
Application filed by Ayerst Mckenna & Harrison filed Critical Ayerst Mckenna & Harrison
Publication of IE37060L publication Critical patent/IE37060L/en
Publication of IE37060B1 publication Critical patent/IE37060B1/en

Links

Classifications

    • 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)
  • Indole Compounds (AREA)

Abstract

1391234 Indole derivatives AYERST Mc- KENNA & HARRISON Ltd 15 Jan 1973 [13 Jan 1972 12 Oot 1972] 2005/73 Heading C2C The invention comprises compounds of the general Formula I in which R<SP>1</SP> is lower alkyl or lower cycloalkyl; R<SP>2</SP> , R<SP>3</SP> , R<SP>4</SP> and R<SP>5</SP> are the same or different and are hydrogen or lower alkyl; R<SP>6</SP> is hydrogen, lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, nitro or halo; R<SP>7</SP> is hydrogen, lower alkyl, lower alkenyl, propargyl, phenyl (lower) alkyl or a radical of formula -AlkNR<SP>8</SP>R<SP>9</SP> in which Alk is an alkylene group of formula 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> in which are hydrogen or lower alkyl and R<SP>8</SP> and R<SP>9</SP> are hydrogen or lower alkyl or together with the nitrogen atom to which they are joined form a 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1- piperazinyl, 4-(lower alkyl) piperazinyl or 4- [hydroxy (lower)alkyl]-1-piperazinyl; X is O or S; and Y is lower alkyl, phenyl(lower)alkyl or a group -AlkNR<SP>8</SP>R<SP>9</SP> as defined above in which Alk may also be CR<SP>10</SP>R<SP>11</SP>; with the proviso that at least one of R<SP>7</SP> and Y is -Alk-NR<SP>8</SP>R<SP>9</SP>; and the corresponding acid addition salts thereof. The lower alkyl groups referred to are those with 1-6 carbon atoms, the "lower" alkenyl radicals contain 2-6 carbon atoms the phenyl, (lower) alkyl groups are those in which the alkyl group contains 1-4 carbon atoms and the lower cycloalkyi radicals contain 3-6 carbon atoms. The compounds of the invention may be made by reacting a compound of Formula II in which X<SP>1</SP> is hydroxy mercapto, -S-SO 3 Na or S-SO 3 4 with a compound of formula R<SP>1</SP>COZ in which Z is (a) C00R<SP>19</SP> or Alk<SP>1</SP>COOR<SP>19</SP> in which R<SP>19</SP> is hydrogen or lower alkyl and Alk<SP>1</SP> 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>or in which R<SP>10</SP>-R<SP>13</SP> are H or alkyl; (b) CONR<SP>8</SP>R<SP>9</SP> or Alk<SP>1</SP>CONR<SP>8</SP>R<SP>9</SP>; (c) CH 2 OCOR<SP>20</SP> or in which R<SP>20</SP> is H or lower alkyl; (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>, 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> in which C<SP>10</SP>-C<SP>16</SP> are H or alkyl and L is halo; (e) AlkNR<SP>8</SP>COR<SP>21</SP> in which AlkR<SP>8</SP> are as defined above and R<SP>21</SP> is H or C 1 -C 5 alkyl; (f) AlkNO 2 (g) lower alkyl or phenyl (lower) alkyl or (h) AIkNR<SP>8</SP>R<SP>9</SP> to give a compound of Formula VII In the case when Z is Alk-NR<SP>8</SP>R<SP>9</SP> the product is the desired product of Formula I; when Z is one of the other groups the compound may be converted to one of the desired products as follows: (a) when Z is COOB<SP>19</SP> or Alk<SP>1</SP>COOR<SP>19</SP>: by hydrolysis of the group Z to the free acid, amidation and reduction and if desired N- alkylation of the indole nitrogen to give compounds in which Y is -AlkNR<SP>8</SP>R<SP>9</SP>; (b) when Z is CONR<SP>8</SP>R<SP>5</SP> or Alk<SP>1</SP>-CONR<SP>8</SP>R<SP>9</SP> by reduction and if desired N-alkylation &C of the indole ring; (c) when Z is CH 2 OCOR<SP>20</SP> or Alk'CH 2 OCOR<SP>20</SP> by hydrolysis to give the corresponding alcohol which is oxidized to the corresponding aldehyde; the aldehyde is reacted with an amine of formula NHR<SP>8</SP>R<SP>9</SP>; the nitrogen in the indole ring may then be substituted as required; (d) when Z is Alk<SP>2</SP>L by treatment with an excess of an amine HNR<SP>8</SP>R<SP>9</SP>; when Z is AIkNR<SP>8</SP>COR<SP>21</SP> by reduction with a complex metal hydride; (f) when Z is Alk-NO 2 by reduction with a complex metal hydride; (g) when Z is lower alkyl or phenyl (lower) alkyl by treatment with an amino (lower) alkyl halide which introduces the group-(Alk)NR<SP>8</SP>R<SP>9</SP> on to the indole nitrogen atom. In cases when R<SP>7</SP> is not a group -Alk-NR<SP>8</SP>R<SP>9</SP> the group R<SP>7</SP> may be introduced into the nitrogen atom of the indole ring at any stage in the process. A very large number examples of preparation of the compounds of the invention and of intermediates therefor are given. The products of the invention are stated to have valuable pharmacological properties. [GB1391234A]
IE1773A 1972-01-13 1973-01-05 Indole derivatives IE37060B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US00217627A US3852285A (en) 1972-01-13 1972-01-13 Pyrano- and thiopyranoindole derivatives
US297130A US3904617A (en) 1972-10-12 1972-10-12 Process for preparing new heterocyclic derivatives

Publications (2)

Publication Number Publication Date
IE37060L true IE37060L (en) 1973-07-13
IE37060B1 IE37060B1 (en) 1977-04-27

Family

ID=26912101

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1773A IE37060B1 (en) 1972-01-13 1973-01-05 Indole derivatives

Country Status (7)

Country Link
CA (1) CA978526A (en)
DE (1) DE2301525A1 (en)
FR (1) FR2181671B1 (en)
GB (1) GB1391234A (en)
HK (1) HK22578A (en)
IE (1) IE37060B1 (en)
MY (1) MY7800240A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4118394A (en) * 1976-10-18 1978-10-03 Ayerst, Mckenna & Harrison Limited Pyrano- and thiopyranoindole derivatives
JPS557201A (en) * 1978-05-23 1980-01-19 Shionogi & Co Ltd Derivative of tetrahydrothiopyrano(2,3-b)indole
JPS56120686A (en) * 1980-02-27 1981-09-22 Shionogi & Co Ltd Tetrahydrothiopyrano 3,2-b indole derivative

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3142678A (en) * 1962-01-09 1964-07-28 American Home Prod Amino substituted penthienoindoles

Also Published As

Publication number Publication date
IE37060B1 (en) 1977-04-27
DE2301525A1 (en) 1973-07-19
HK22578A (en) 1978-05-05
CA978526A (en) 1975-11-25
MY7800240A (en) 1978-12-31
FR2181671B1 (en) 1976-07-02
GB1391234A (en) 1975-04-16
FR2181671A1 (en) 1973-12-07

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