FR2019185A1 - 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta - Google Patents

4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta

Info

Publication number
FR2019185A1
FR2019185A1 FR6933087A FR6933087A FR2019185A1 FR 2019185 A1 FR2019185 A1 FR 2019185A1 FR 6933087 A FR6933087 A FR 6933087A FR 6933087 A FR6933087 A FR 6933087A FR 2019185 A1 FR2019185 A1 FR 2019185A1
Authority
FR
France
Prior art keywords
alkyl
indole
hydroxymethylindoles
propoxy
hydroxy
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
FR6933087A
Other languages
French (fr)
Other versions
FR2019185B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
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 CH1459168A external-priority patent/CH508624A/en
Priority claimed from CH1046569A external-priority patent/CH536302A/en
Priority claimed from CH1083769A external-priority patent/CH513853A/en
Priority claimed from CH1126669A external-priority patent/CH533110A/en
Priority claimed from CH1177869A external-priority patent/CH513855A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of FR2019185A1 publication Critical patent/FR2019185A1/en
Application granted granted Critical
Publication of FR2019185B1 publication Critical patent/FR2019185B1/fr
Granted legal-status Critical Current

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
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

4-(2-Hydroxy-3-amino-propoxy)-indole-2-carboxylic acids and esters and 2-hydroxymethylindoles as betadrenergic agents and intermediates M3A. Are new compounds of formulae (Ia) and Ib) and their salts. (where R1=opt. branched 1-5C alkyl, cyclo alkyl, 8-10C-phenylalkyl or 1-adamantyl; R2=H or 1-5C alkyl). They are prepared by (a) reacting an appropriate 3-halo-2-hydroxypropoxy indole or an epoxypropoxy indole with R1NH2, (b) hydrogenolysis of the N-benzyl derivs. of (Ia) or (Ib), (c) reduction of the Schiffs base derived from (Ia or Ib where R1=H) with a ketone R3COR4 (where R3 and R4=lower alkyl) with simultaneous reduction of COOR to -CH2OH (d) reduction of (Ia) to (Ib) and (e) hydrolysis of (Ia, R2=alkyl) to the free acid or esterification of (Ia E2-H). Compounds (II), useful as intermediates where R'2 = 1-5 alkyl are prepared by reacting 2-benzyloxy-6-nitro-toluene with an oxalic acid ester and reductively cyclising the product. Prefd. compounds are (Ia) and (Ib) R1=iso-P2 and R2=H, Me or Et, R1=tert-Bu and R2=H or Et, R1=tert pentyl and R2=Et, R1=cyclopropyl, and R2=Et; (Ib) R1=sec-Bu, 3-pentyl, adamantyl and Me; and (II) R'2=Me and Et.
FR6933087A 1968-09-30 1969-09-29 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta Granted FR2019185A1 (en)

Applications Claiming Priority (13)

Application Number Priority Date Filing Date Title
CH1459168A CH508624A (en) 1968-09-30 1968-09-30 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta
CH413169 1969-03-19
CH1040169 1969-07-08
CH1046569A CH536302A (en) 1968-09-30 1969-07-09 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta
CH1083769A CH513853A (en) 1969-07-16 1969-07-16 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta
CH1117969 1969-07-22
CH1126669A CH533110A (en) 1969-07-23 1969-07-23 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta
CH1126469 1969-07-23
CH1126569 1969-07-23
CH1165569 1969-07-31
CH1177869A CH513855A (en) 1969-08-04 1969-08-04 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta
CH1177969 1969-08-04
CH1184469 1969-08-05

Publications (2)

Publication Number Publication Date
FR2019185A1 true FR2019185A1 (en) 1970-06-26
FR2019185B1 FR2019185B1 (en) 1973-01-12

Family

ID=27583940

Family Applications (1)

Application Number Title Priority Date Filing Date
FR6933087A Granted FR2019185A1 (en) 1968-09-30 1969-09-29 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta

Country Status (1)

Country Link
FR (1) FR2019185A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2085732A1 (en) * 1970-03-24 1971-12-31 Sandoz Sa
FR2108098A1 (en) * 1970-09-30 1972-05-12 Sandoz Sa
FR2398058A1 (en) * 1977-07-21 1979-02-16 Sandoz Sa NEW DERIVATIVES OF INDOLE, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE693518A (en) * 1966-02-01 1967-08-01

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE693518A (en) * 1966-02-01 1967-08-01

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2085732A1 (en) * 1970-03-24 1971-12-31 Sandoz Sa
FR2108098A1 (en) * 1970-09-30 1972-05-12 Sandoz Sa
FR2398058A1 (en) * 1977-07-21 1979-02-16 Sandoz Sa NEW DERIVATIVES OF INDOLE, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Also Published As

Publication number Publication date
FR2019185B1 (en) 1973-01-12

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