171-75-5

Basic information

• Product Name: SPIRO[INDOLINE-3,4'-PIPERIDINE]
• Synonyms: 1,2-DIHYDRO-1'H-SPIRO[INDOLE-3,4'-PIPERIDINE];SPIRO[INDOLINE-3,4'-PIPERIDINE];1,2-Dihydrospiro[3H-indole-3,4'-piperidine];1,2-dihydrospiro[indole-3,4'-piperidine];Spiro[3H-indole-3,4'-piperidine], 1,2-dihydro-;1,2-Dihydrospiro[3H-indole-3,4'-piperidine] 2HCl
• CAS NO: 171-75-5
• Molecular Formula: C₁₂H₁₆N₂
• Molecular Weight: 188.272
• Mol File: 171-75-5.mol

Chemical Properties

• Melting Point: 140-142℃
• Appearance: /
• Density: 1.13
• Storage Temp.: 2-8°C
• CAS DataBase Reference: SPIRO[INDOLINE-3,4'-PIPERIDINE](CAS DataBase Reference)
• NIST Chemistry Reference: SPIRO[INDOLINE-3,4'-PIPERIDINE](171-75-5)
• EPA Substance Registry System: SPIRO[INDOLINE-3,4'-PIPERIDINE](171-75-5)

Safety Data

• Hazardous Substances Data: 171-75-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
SPIRO[INDOLINE-3,4'-PIPERIDINE] is used as a key intermediate compound for the synthesis of spiro-indanone derivatives. These derivatives have been found to act as antagonists of the human CCR5 receptor, which plays a crucial role in the entry of HIV-1 virus into human cells. By blocking this receptor, spiro-indanone derivatives can potentially serve as effective anti-HIV-1 agents, offering a new approach to combat the HIV-1 virus and its associated complications.

Upstream product

• 326-62-5 2-fluorophenyl acetonitrile 
• 55-86-7 mechlorethamine hydrochloride 
• 167484-18-6 benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate 
• 100-63-0 phenylhydrazine 
• 138163-08-3 N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde 
• 726198-18-1 4-cyano-4-(2-fluorophenyl)-1-N-(tert-butyloxycarbonyl)piperidine 
• 252002-43-0 4-cyano-4-(2-fluorophenyl)piperidine 

Downstream Products

• 167484-18-6 benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate 
• 958007-08-4 tert-butyl [2-({[6-(1,2-dihydro-1'H-spiro[indole-3.4'-piperidin]-1'-yl)pyridine-3-yl]carbonyl}amino)-4-(2-thienyl)phenyl]carbamate 
• 1093955-94-2 (1S)-1-{1-[(2E)-3-(3,5-difluorophenyl)-2-propenoyl]-4-piperidinyl}-2-(1,2-dihydro-1'H-spiro[indole-3,4'-piperidin]-1'-yl)ethanol 
• 870072-74-5 1,2-dihydro-1-(2-nitrophenyl)-spiro[3H-indole-3,4'-piperidine]-1'-carboxylic acid phenylmethyl ester 
• 870072-22-3 1-(2-(spiro[indoline-3,4′-piperidine]-1-yl)phenyl)-3-(4-(trifluoromethoxy)phenyl)urea 
• 870072-29-0 1-(2-(1'-benzylspiro[indoline-3,4'-piperidine]-1-yl)phenyl)-3-(4-(trifluoromethoxy)phenyl)urea 

Relevant articles and documents

SUBSTITUTED HETEROCYCLIC DERIVATIVES AS GPR AGONISTS AND USES THEREOF

The present invention generally relates to substituted heterocyclic derivatives (the compounds of Formula (I)), processes for their preparation, pharmaceutical compositions containing said compounds, their use as G-protein coupled receptor (GPR) agonists, particularly as GPR40 agonists and methods of using these compounds in the treatment of GPR40 mediated diseases or conditions such as Type 2 diabetes, obesity, dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

Conformationally constrained ortho- Anilino diaryl ureas: Discovery of 1-(2-(1′-Neopentylspiro[indoline-3,4′-piperidine]-1-yl)phenyl) -3-(4-(trifluoromethoxy)phenyl)urea, a potent, selective, and bioavailable P2Y1 antagonist

Preclinical antithrombotic efficacy and bleeding models have demonstrated that P2Y1 antagonists are efficacious as antiplatelet agents and may offer a safety advantage over P2Y12 antagonists in terms of reduced bleeding liabilities. In this article, we describe the structural modification of the tert-butyl phenoxy portion of lead compound 1 and the subsequent discovery of a novel series of conformationally constrained ortho-anilino diaryl ureas. In particular, spiropiperidine indoline-substituted diaryl ureas are described as potent, orally bioavailable small-molecule P2Y1 antagonists with improved activity in functional assays and improved oral bioavailability in rats. Homology modeling and rat PK/PD studies on benchmark compound 3l will also be presented. Compound 3l was our first P2Y1 antagonist to demonstrate a robust oral antithrombotic effect with mild bleeding liability in the rat thrombosis and hemostasis models.

SPIROINDOLINES AS MODULATORS OF CHEMOKINE RECEPTORS

The present invention relates to a compound of the following formula: where R1-R6, R10, Y, n, m, p, and q are as defined herein. Compounds and compositions of the present invention are useful for the treatment of diseases

INDOL-3-YL-CARBONYL-SPIRO-PIPERIDINE DERIVATIVES AS V1A RECEPTOR ANTAGONISTS

The invention relates to indol-3-yl-carbonyl-spiro-piperidine derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the spiro-piperidine head group A and the residues R1, R2 and R3 are as defined herein. The invention further relates to pharmaceutical compositions containing such compounds, methods for preparing the compounds and pharmaceutical compositions, and their use in the treatment of dysmenorrhea, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, obsessive compulsive disorder, anxious and depressive disorders.

N-linked heterocyclic antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions

The present invention provides novel ureas containing N-aryl or N-heteroaryl substituted heterocycles of Formula (I): or a stereoisomer, tautomer, pharmaceutically acceptable salt or solvate form thereof, wherein the variables A, B, D and W are as defined herein. These compounds are selective inhibitors of the human P2Y1 receptor which can be used as medicaments.

Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions

The present invention provides novel ureas containing N-aryl or N-heteroaryl substituted heterocycles and analogues thereof, which are selective inhibitors of the human P2Y1 receptor. The invention also provides for various pharmaceutical compositions of the same and methods for treating diseases responsive to modulation of P2Y1 receptor activity.

A convenient synthesis of 1′-H-spiro-(indoline-3,4′-piperidine) and its derivatives

A simple synthetic route has been developed to prepare 1′-H- spiro(indoline-3,4′-piperidine) (1d). Dialkylation of 2- fluorophenylacetonitrile with N-(tert-butyloxycarbonyl)-bis(2-chloroethyl)amine (5) gave 6. Deprotection of Boc followed by cyclization resulted 1d in 67% overall yield. Selective Boc or Cbz protection of 1′-N gave 1a or 1b with 90 and 85% yield, respectively. Thus, in a five-step procedure, 1a and 1b were synthesized from commercially available reagents in over 50% overall yield. All 3 compounds (1a, 1b and 1d) can be utilized as templates to synthesize compounds for GPCR targets.