127168-98-3

Basic information

• Product Name: ISOINDOLIN-5-YLMETHANOL
• Synonyms: ISOINDOLIN-5-YLMETHANOL;2,3-dihydro-1H-Isoindole-5-Methanol;5-hydroxymethylisoindoline
• CAS NO: 127168-98-3
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• Mol File: 127168-98-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: ISOINDOLIN-5-YLMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: ISOINDOLIN-5-YLMETHANOL(127168-98-3)
• EPA Substance Registry System: ISOINDOLIN-5-YLMETHANOL(127168-98-3)

Safety Data

• Hazardous Substances Data: 127168-98-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ISOINDOLIN-5-YLMETHANOL is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its presence in this industry is crucial for the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, ISOINDOLIN-5-YLMETHANOL is utilized as a precursor in the production of agrochemicals, aiding in the creation of substances that protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
ISOINDOLIN-5-YLMETHANOL is used as a reagent in organic synthesis for the preparation of a diverse array of organic compounds, including dyes and pigments, which are essential in coloring textiles, plastics, and other materials.
Used in Material Development:
ISOINDOLIN-5-YLMETHANOL is employed in the development of new materials, where its unique properties can be harnessed to create innovative products with enhanced performance characteristics.
Used in Research and Development:
ISOINDOLIN-5-YLMETHANOL is used as a research tool in the exploration of new chemical reactions and processes, furthering scientific understanding and paving the way for future technological breakthroughs.

Upstream product

• 905843-84-7 2,3-dihydro-5-formyl-2-tert-butoxycarbonyl(1H)isoindole 
• 253801-14-8 tert-butyl 5-(hydroxymethyl)-1,3-dihydro-2H-isoindole-2-carboxylate 
• 20896-23-5 methyl 3,4-bis(bromomethyl)benzoate 
• 38404-42-1 methyl 3,4-dimethylbenzoate 
• 127168-94-9 methyl 2,3-dihydro-2-(phenylmethyl)-1H-isoindole-5-carboxylate 
• 127169-16-8 (2-benzyl-2,3-dihydro-1H-isoindol-5-yl)1-methanol 

Downstream Products

• 253801-14-8 tert-butyl 5-(hydroxymethyl)-1,3-dihydro-2H-isoindole-2-carboxylate 
• 439691-87-9 (2-methyl-2,3-dihydro-1H-isoindol-5-yl)-methanol 
• 1019889-84-9 5-hydroxymethyl-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester 
• 854092-28-7 5-{[methyl-(1-phenyl-2-pyrrolidin-1-yl-ethyl)-carbamoyl]-methyl}-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 
• 253801-15-9 5-formyl-1,2-dihydro-isoindole-2-carboxylic acid tertiary butyl ester 

Relevant articles and documents

PHARMACEUTICAL COMPOUNDS

The invention provides a compound for use in medicine, the compound being a compound of the formula (VI0) or a salt, solvate, tautomer or N-oxide thereof: wherein the bicyclic group: is selected from the structures C1, C5 and C6: wherein n is 0, 1, 2 or 3; R1 is hydrogen, hydroxy, or O—Rz; R2a is hydroxy, methoxy or O—Rz; provided that at least one of R1 and R2a is O—Rz; Rz is Lp-Rp1; SO3H; a glucuronide residue; a mono-, di- or tripeptide residue; or Lp is a bond, C═O, (C═O)O, (C═O)NRp1 or S(O)xNRp1; x is 1 or 2; Rp1 is hydrogen or a an optionally substituted C1-25 hydrocarbyl group containing 0, 1 or 2 carbocyclic rings and 0, 1, 2, 3, 4, 5 or 6 carbon-carbon multiple bonds, provided that Rp1 is not hydrogen when Lp is a bond, C═O or (C═O)O; and provided also that O—Rz does not contain an O—O moiety; and excluding compounds wherein R1 is hydroxy and R2a is methoxy; Rp2 and Rp3 are the same or different and each is a group Rp1; and R3, R4a, R8 and R10 are defined in the claims. The compounds of formula (VI0) are pro-drugs of parent compounds wherein R1 and/or R2a are hydroxy, wherein the parent compounds have Hsp90 inhibiting activity.

Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of Cyclin D1-CDK4: Synthesis, biological evaluation and structure-activity relationships. Part 2

The design, synthesis and evaluation of novel thieno[2,3-d]pyrimidin-4-yl hydrazone analogues as cyclin-dependent kinase 4 (CDK4) inhibitor are described. Focusing on the optimization of the heteroaryl moiety at the hydrazone with substituted phenyl group

PHARMACEUTICAL COMBINATIONS

The invention provides combinations comprising (or consisting essentially of) one or more ancillary compound(s) and a compound of the formula (I): or salts, tautomers, solvates and N-oxides thereof; wherein R1 is hydroxy or hydrogen; R2 is hydroxy; methoxy or hydrogen; provided that at least one of R1 and R2 is hydroxy; R3 is selected from hydrogen; halogen; cyano; optionally substituted C1-5 hydrocarbyl and optionally substituted C1- 5 hydrocarbyloxy; R4 is selected from hydrogen; a group -(O)n-R7 where n is 0 or 1 and R7 is an optionally substituted acyclic C1-5 hydrocarbyl group or a monocyclic carbocyclic or heterocyclic group having 3 to 7 ring members; halogen; cyano; hydroxy; amino; and optionally substituted mono- or di-C1-5 hydrocarbyl-amino; or R3 and R4 together form a monocyclic carbocyclic or heterocyclic ring of 5 to 7 ring members; and NR5R6 forms an optionally substituted bicyclic heterocyclic group having 8 to 12 ring members of which up to 5 ring members are heteroatoms selected from oxygen, nitrogen and sulphur. The combinations have activity as Hsp90 inhibitors.

HYDROBENZAMIDE DERIVATIVES AS INHIBITORS OF HSP90

The invention provides an acid addition salt of a compound of the formula (1) Also provided by the invention are processes for preparing the compound of formula (1) and alkyl analogues thereof, novel intermediates for use in the process and methods for preparing the intermediates. The invention also provides new medical uses of compounds of the formula (1) and its ethyl analogue.

PHARMACEUTICAL COMBINATIONS

The invention provides combinations comprising (or consisting essentially of) one or more ancillary compound(s) and a compound of the formula (I): or salts, tautomers, solvates and N-oxides thereof; wherein R1 is hydroxy or hydrogen; R2 is hydroxy; methoxy or hydrogen; provided that at least one of R1 and R2 is hydroxy; R3 is selected from hydrogen; halogen; cyano; optionally substituted C1-5 hydrocarbyl and optionally substituted C1-5 hydrocarbyloxy; R4 is selected from hydrogen; a group -(O)n-R7 where n is 0 or 1 and R7 is an optionally substituted acyclic C1-5 hydrocarbyl group or a monocyclic carbocyclic or heterocyclic group having 3 to 7 ring members; halogen; cyano; hydroxy; amino; and optionally substituted mono- or di-C1-5 hydrocarbyl-amino; or R3 and R4 together form a monocyclic carbocyclic or heterocyclic ring of 5 to 7 ring members; and NR5R6 forms an optionally substituted bicyclic heterocyclic group having 8 to 12 ring members of which up to 5 ring members are heteroatoms selected from oxygen, nitrogen and sulphur. The combinations have activity as Hsp90 and/or glycogen synthase kinase-3 and/or cyclin dependent kinase inhibitors.

PHARMACEUTICAL COMBINATIONS

The invention provides combinations comprising (or consisting essentially of) one or more ancillary compound(s) and a compound of the formula (I): or salts, tautomers, solvates and N-oxides thereof; wherein R1 is hydroxy or hydrogen; R2 is hydroxy; methoxy or hydrogen; provided that at least one of R1 and R2 is hydroxy; R3 is selected from hydrogen; halogen; cyano; optionally substituted C1-5 hydrocarbyl and optionally substituted C1-5 hydrocarbyloxy; R4 is selected from hydrogen; a group -(O)n-R7 where n is 0 or 1 and R7 is an optionally substituted acyclic C1-5 hydrocarbyl group or a monocyclic carbocyclic or heterocyclic group having 3 to 7 ring members; halogen; cyano; hydroxy; amino; and optionally substituted mono- or di-C1-5 hydrocarbyl-amino; or R3 and R4 together form a monocyclic carbocyclic or heterocyclic ring of 5 to 7 ring members; and NR5R6 forms an optionally substituted bicyclic heterocyclic group having 8 to 12 ring members of which up to 5 ring members are heteroatoms selected from oxygen, nitrogen and sulphur. The combinations have activity as Hsp90 and/or glycogen synthase kinase-3 and/or cyclin dependent kinase and/or aurora kinase inhibitors.

PHARMACEUTICAL COMPOUNDS

The invention provides the use of a compound for the manufacture of a medicament for the treatment of pain, wherein the compound is a compound of the formula (Vl): or a salt, solvate, tautomer or N-oxide thereof; wherein the bicydic group: is selected from the structures C1, C5 and C6: wherein n, R1, R2a, R3, R4a, R8 and R10 are as defined in the claims. The invention also provides the use of a compound of the formula (Vl) for the manufacture of a medicament for the prophylaxis or treatment of a fungal, protozoal, viral or parasitic disease state or condition (other than a disease state or condition due to Plasmodium falciparum) or for use in the prophylaxis or treatment of Ewing's sarcoma, atherosclerosis or lupus erythematosus

Synthesis of substituted 5-aminomethyl tetrahydro-isoquinolines and dihydro-isoindoles

The synthesis of ten substituted aminomethylene tetrahydro-isoquinolines is described, proceeding in eight steps from 5-hydroxyisoquinoline via reductive amination of N-Boc tetrahydro-isoquinoline 5-carboxaldehyde. Likewise, reductive amination was used to prepare four substituted dihydro-isoindoles from the corresponding aldehyde. The dihydro-isoindole ring system was conveniently accessed via a 2+2+2 cycloaddition reaction.

AMIDE RESORCINOL COMPOUNDS

The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as HSP-90 inhibitors.

COMPOUND INHIBITING DIPEPTIDYL PEPTIDASE IV

The invention aims to provide a dipeptidyl peptidase IV inhibitor which is satisfactory in respect of activity, stability and safety and has an excellent action as a pharmaceutical agent. The invention is directed to a compound represented by the following general formula or a pharmaceutically acceptable salt thereof: wherein R1 and R2 each represents hydrogen, an optionally substituted C1-6 alkyl group, or -COOR5 whereupon R5 represents hydrogen or an optionally substituted C1-6 alkyl group, or R1 and R2, together with a carbon atom to which they are bound, represent a 3- to 6-membered cycloalkyl group, R3 represents hydrogen or an optionally substituted C6-10 aryl group, R4 represents a hydrogen or a cyano group, D represents -CONR6-, -CO- or -NR6CO-, R6 represents hydrogen or an optionally substituted C1-6 alkyl group, E represents -(CH2)m- whereupon m is an integer of 1 to 3, -CH2OCH2-, or -SCH2-, n is an integer of 0 to 3, and A represents an optionally substituted bicyclic heterocyclic group or bicyclic hydrocarbon group.