170367-68-7

Usage

Uses

Used in Pharmaceutical Industry:
Carbamic acid, [(1R)-2-cyano-1-methylethyl]-, 1,1-dimethylethyl ester (9CI) is used as an intermediate in the synthesis of various biologically active compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Synthesis of Immunosuppressive Agents:
Carbamic acid, [(1R)-2-cyano-1-methylethyl]-, 1,1-dimethylethyl ester (9CI) is used as an intermediate for the synthesis of spermidine analogs of 15-deoxyspergualin, which possess immunosuppressive activities. These analogs can be employed in the treatment of autoimmune diseases and transplantation medicine to prevent organ rejection.
Used in Synthesis of HIV-1 Inhibitors:
Carbamic acid, [(1R)-2-cyano-1-methylethyl]-, 1,1-dimethylethyl ester (9CI) is also utilized in the preparation of pyridin-2-ylmethylaminopiperidin-1-ylbutyl amide CCR5 antagonists. These antagonists serve as inhibitors of M-tropic (R5) HIV-1 replication, playing a crucial role in the development of antiretroviral drugs for the treatment of HIV/AIDS.

Upstream product

• 773837-37-9 sodium cyanide 
• 126301-16-4 (2R)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 194156-55-3 tert-butyl 1-cyanopropan-2-ylcarbamate 
• 352705-03-4 (2R)-2-[(tert-butoxycarbonyl)amino]propyl 4-methylbenzene-1-sulfonate 
• 79069-13-9 (R)-2-tertbutoxycarbonylamino-1-propanol 
• 143-33-9 sodium cyanide 

Downstream Products

• 170367-69-8 (3-amino-1(R)-methylpropyl)carbamic acid, 1,1-dimethylethyl ester 
• 875680-89-0 (R)-N¹-(o-nitrophenylsulfonyl)-N³-(tert-butyloxycarbonyl)-1,3-diaminobutane 
• 875680-91-4 (R)-N¹-phthaloyl-N⁵-(o-nitrophenylsulfonyl)-N⁸-(tert-butyloxycarbonyl)-1,8-diamino-5-azanonane 
• 932032-30-9 (R)-N⁵-(o-nitrophenylsulfonyl)-N⁸-(tert-butyloxycarbonyl)-8-amino-5-aza-1-iodononane 
• 932032-31-0 (R)-N¹²-(tert-butyloxycarbonyl)-N⁹-(o-nitrophenylsulfonyl)-1,12-diamino-4,9-diazatridecane 
• 170367-70-1 [1(R)-methyl-3-[(phenylmethyl)amino]propyl]carbamic acid, 1,1-dimethylethyl ester 
• 170367-71-2 3-[(3-cyanopropyl)(phenylmethyl)amino-1(R)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester 
• 170367-72-3 3-[(4-aminobutyl)(phenylmethyl)amino-1(R)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester 
• 252353-69-8 [3-[[4-(2,4-dioxo-3-oxazolidinyl)butyl](phynylmethyl)amino]-1-methylpropyl]carbamic acid, 1,1-dimethylethyl ester (R) 
• 170367-76-7 2,2,6-trimethyl-4,15-dioxo-9-(phenylmethyl)-3,16-dioxa-5,9,14-triazaoxadecan-18-oic acid (R) 
• 170367-82-5 [21-[[(1,1-dimethylethoxy)carbonyl]amino]-1,25,25-trimethyl-10,12,23-trioxo-4-(phenylmethyl)-24-oxa-4,9,13,20,22-pentaaza-21-hexacosen-1-yl]carbamic acid, 1,1-dimethylethyl ester (R) 
• 170367-78-9 [4-[[3-[[(1,1-dimethylethoxy)carbonyl]amino]butyl](phenylmethyl)amino]butyl]carbamic acid, 11-[[(1,1-dimethylethoxy)carbonyl]amino]-15,15-dimethyl-2,13-dioxo-14-oxa-3,4,12-triaza-11-hexadecen-1-yl ester (R) 
• 6078-06-4 (R)-methyl 3-aminobutanoate hydrochloride 
• 159991-23-8 (R)-3-((tert-butoxycarbonyl)amino)butanoic acid 

Relevant academic research and scientific papers

Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium

A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3-hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo-aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β-aminonitriles, structural analogues of β-hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α- aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation.

BICYCLIC PYRIMIDONE COMPOUNDS AS INHIBITORS OF LP-PLA2

The present invention relates to novel pyrimido[1,6-a]pyrimidin-6(2H)-one compounds that inhibit Lp-PLA2 activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases associated with the activity of Lp-PLA2, for example atherosclerosis, Alzheimer's disease.

Practical convergent laboratory-scale synthesis of a CCR5 receptor antagonist

An efficient laboratory-scale synthesis has been developed for the selective CCR5 antagonist 1. The convergent route has a longest linear sequence of nine steps (15 steps overall), and has overall yields of 18-25%. The route has enabled the preparation of 550 g of 1.

Design and synthesis of pyridin-2-ylmethylaminopiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication

A series of CCR5 antagonists were optimized for potent inhibition of R5 HIV-1 replication in peripheral blood mononuclear cells. Compounds that met acceptable ADME criteria, selectivity, human plasma protein binding, potency shift in the presence of α-glycoprotein were evaluated in rat and dog pharmacokinetics.

3-SUBSTITUTED 1,2,3-TRIAZIN-4-ONE'S AND 3-SUBSTITUTED 1,3-PYRIMIDINONE'S FOR ENHANCING GLUTAMATERGIC SYNAPTIC RESPONSES

This invention relates to compounds, pharmaceutical compositions and methods for use in the prevention and treatment of cerebral insufficiency, including enhancement of receptor functioning in synapses in brain networks responsible for basic and higher order behaviors. These brain networks, which are involved in regulation of breathing, and cognitive abilities related to memory impairment, such as is observed in a variety of dementias, in imbalances in neuronal activity between different brain regions, as is suggested in disorders such as Parkinson''s disease, schizophrenia, respiratory depression, sleep apneas, attention deficit hyperactivity disorder and affective or mood disorders, and in disorders wherein a deficiency in neurotrophic factors is implicated, as well as in disorders of respiration such as overdose of an alcohol, an opiate, an opioid, a barbiturate, an anesthetic, or a nerve toxin, or where the respiratory depression results form a medical condition such as central sleep apnea, stroke- induced central sleep apnea, obstructive sleep apnea, congenital hypoventilation syndrome, obesity hypoventilation syndrome, sudden infant death syndrome, Rett syndrome, spinal cord injury, traumatic brain injury, Cheney-Stokes respiration, Ondines curse, Prader-Willi''s syndrome and drowning. In a particular aspect, the invention relates to compounds useful for treatment of such conditions, and methods of using these compounds for such treatment.

POLYCYCLIC CARBAMOYLPYRIDONE DERIVATIVE HAVING HIV INTEGRASE INHIBITORY ACTIVITY

The present invention is to provide a novel compound (I), having the anti-virus activity, particularly the HIV integrase inhibitory activity, and a drug containing the same, particularly an anti-HIV drug, as well as a process and an intermediate thereof. Compound (I) wherein Z1 is NR4; R1 is hydrogen or lower alkyl; X is a single bond, a hetero atom group selected from O, S, SO, SO2 and NH, or lower alkylene or lower alkenylene in which the hetero atom group may intervene; R2 is optionally substituted aryl; R3 is hydrogen, a halogen, hydroxy, optionally substituted lower alkyl etc; and R4 and Z2 part taken together forms a ring, to form a polycyclic compound, including e.g., a tricyclic or tetracyclic compound.

Structure - Immunosuppressive activity relationships of new analogues of 15-deoxyspergualin. 2. Structural modifications of the spermidine moiety

A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine 'D' region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene α to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60c which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

15-deoxyspergualin analogs, their method of preparation and their use in therapeutics

The present invention relates, by way of novel industrial products, to compounds which are structurally related to 15-deoxyspergualin and which have the formula STR1 in which: A is a single bond, a group --CH2 --, a group --CH2 O--, a group --CH2 NH--, a group --CH(OH)--, a group --CHF-- or a group --CH(OCH3)--, and n is equal to 6 or 8, and their addition salts. These novel compounds are useful especially as immunosuppressants. The invention further relates to the method of preparing said compounds.