159752-10-0

Basic information

• Product Name: MK-677
• Synonyms: MK-677;2-Amino-N-[(1R)-2-[1,2-dihydro-1-(methylsulfonyl)spiro[3H-indole-3,4'-piperidin]-1'-yl]-2-oxo-1-[(phenylmethoxy)methyl]ethyl]-2-methylpropanamide methanesulfonate;(R)-1'-(2-Methylalanyl-O-benzyl-D-seryl)-1-(Methylsulfonyl)-1,2-dihydrospiro[indole-3,4'-piperidine] Mesylate;Crescendo;IbutaMoren Mesylate(MK-677);MK-667;N-[1(R)-1,2-Dihydro-1-methanesulfonylspiro-3H-indole-3,4′-piperidin)-1′-yl]carbonyl-2-(phenylmethoxy)-ethyl-2-amino-2-methylpropanamide methanesulfonate;IBUTAMORIN
• CAS NO: 159752-10-0
• Molecular Formula: C27H36N4O5S.CH4O3S
• Molecular Weight: 624.776
• EINECS: 1308068-626-2
• Product Categories: SARMs(Selective androgen receptor modulator)
• Mol File: 159752-10-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 868.9 °C at 760 mmHg
• Flash Point: 479.3 °C
• Appearance: white to beige/
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble5mg/mL, clear
• CAS DataBase Reference: MK-677(CAS DataBase Reference)
• NIST Chemistry Reference: MK-677(159752-10-0)
• EPA Substance Registry System: MK-677(159752-10-0)

Safety Data

• WGK Germany: 3
• RTECS: TX1404490
• Hazardous Substances Data: 159752-10-0(Hazardous Substances Data)

Usage

Benefits

The benefits of MK-677 include muscle-building, a reduction in muscle wasting, better bone density, improved sleep, and anti-aging properties. It may also have nootropic effects and it can be beneficial in treating growth hormone deficiencies. Read on for a more in-depth look at these benefits.

Uses

Growth hormone releasing factor.MK-677 is a potent, non-peptide ghrelin receptor agonist.

Biochem/physiol Actions

It is also known as ibutamoren mesylate. MK-677 is a mimic of growth hormone (GH)-releasing peptide and is orally active.

Upstream product

• 6751-75-3 2-bromoresorcinol 
• 178261-41-1 1-(methylsulfonyl)spiro[indoline-3,4’-piperidine] 
• 159634-89-6 (R)-3-Benzyloxy-2-(2-tert-butoxycarbonylamino-2-methyl-propionylamino)-propionic Acid 
• 34259-90-0 1-benzoyl-4-nitromethyl-piperidin-4-ol 
• 180465-66-1 C₂₈H₃₇N₃O₆S 
• 180465-67-2 C₂₃H₂₉N₃O₄S 
• 167484-18-6 benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate 
• 184289-85-8 benzyl spiro[indole-3,4'-piperidine]-1'-carboxylate 
• 100-63-0 phenylhydrazine 
• 10314-99-5 benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate 
• 138163-08-3 N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde 
• 10314-98-4 1-benzyloxycarbonylpiperidine-4-carboxylic acid 
• 100-39-0 benzyl bromide 
• 47173-80-8 N-Boc-D-serine(Bzl)-OH 

Relevant articles and documents

Domino Aryne Annulation via a Nucleophilic-Ene Process

1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.

A facile synthesis of the spiroindoline-based growth hormone secretagogue, MK-677

A facile and improved route for the synthesis of the orally active spiroindoline-based growth hormone secretagogue, MK-677 was described. The key step adopted the Fischer indole/reduction strategy. The preparation of the key intermediates N-protected piperidine carboxaldehyde 5 and the N-Boc-O-benzyl-d-serine (2) are also optimized.

Polymorphic forms of a growth hormone secretagogue

This invention is concerned with polymorphic forms of the compound N-?1(R)-?(1,2-dihydro-1-methanesulfonylspiro?3H-indole-3,4'-piperdin!-1'-yl)carbonyl!-2-(phenylmethyloxy)ethyl!-2-amino-2-methylpropanamide methanesulfonate which is a growth hormone secretagogue that is useful in food animals to promote their growth thereby rendering the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, and to treat medical conditions which are improved by the anabolic effects of growth hormone. The instant polymorphic forms have advantages over the other known forms of N-?1(R)-?(1,2-dihydro-1-methanesulfonylspiro?3H-indole-3,4'-piperdin!-1'-yl)carbonyl!-2-(phenylmethyloxy)-ethyl!-2-amino-2-methylpropanamide methanesulfonate in terms of thermodynamic stability and suitability for inclusion in pharmaceutical formulations. The present invention is also concerned with processes for preparing these polymorphic forms, pharmaceutical formulations comprising these polymorphic forms as active ingredients and the use of the polymorphic form of the compound and their formulations in the treatment of certain disorders.

Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677

The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48% overall yield from isonipecotic acid 3.

Spiro piperidines and homologs which promote release of growth hormone

There are disclosed certain novel compounds identified as spiro piperidines and homologs which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such spiro compounds as the active ingredient thereof are also disclosed.