179686-45-4

Usage

Uses

Used in Pharmaceutical Development:
(+/-)-N-ALPHA-BOC-AMINO-EPSILON-CAPROLACTAM is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its Boc-protected amino group allows for the controlled formation of amide bonds, which are crucial in the construction of peptide-based drugs and other bioactive molecules.
Used in Agrochemical Synthesis:
In the agrochemical industry, (+/-)-N-ALPHA-BOC-AMINO-EPSILON-CAPROLACTAM serves as a building block for the development of novel agrochemicals with improved properties, such as enhanced stability, selectivity, and bioavailability. Its use in this field contributes to the creation of more effective and environmentally friendly pesticides and other agricultural chemicals.
Used in Advanced Material Production:
(+/-)-N-ALPHA-BOC-AMINO-EPSILON-CAPROLACTAM is utilized as a precursor in the synthesis of advanced materials with unique properties, such as high thermal stability, mechanical strength, and chemical resistance. These materials find applications in various industries, including aerospace, automotive, and electronics.
Used in Organic Synthesis:
As a versatile intermediate in organic chemistry, (+/-)-N-ALPHA-BOC-AMINO-EPSILON-CAPROLACTAM is employed in the synthesis of a wide range of organic compounds, including complex natural products, pharmaceutical agents, and specialty chemicals. Its Boc-protected amino group facilitates the formation of amide bonds and other functional groups, enabling the efficient construction of diverse molecular architectures.

InChI:InChI=1/C11H20N2O3/c1-11(2,3)16-10(15)13-8-6-4-5-7-12-9(8)14/h8H,4-7H2,1-3H3,(H,12,14)(H,13,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 29426-64-0 (R)-α-amino-ε-caprolactam hydrochloride 
• 28957-33-7 (R)-3-amino-azepan-2-one 
• 34619-03-9 tert-butyldicarbonate 
• 17929-90-7 3-aminoazepan-2-one 

Downstream Products

• 393842-94-9 1-(1-benzyloxycarbonylmethyl)-3-(S)-t-butoxycarbonylaminoperhydroazepin-2-one 
• 635754-76-6 (RS)-1-phenyl-2-oxo-3-(tert-butoxycarbonylamino)-azepine 
• 186550-62-9 [1-(3-cyanobenzyl)-2-oxoazepan-3(S)-yl]carbamic acid tert-butyl ester 
• 17929-90-7 3-aminoazepan-2-one 

Relevant academic research and scientific papers

Diphenylsilane as a coupling reagent for amide bond formation

A simple procedure for amide bond formation using diphenylsilane as a coupling reagent is described. This methodology enables the direct coupling of carboxylic acids with primary and secondary amines, releasing only hydrogen and a siloxane as by-products. Only one equivalent of each partner is needed, providing a more sustainable amidation method producing minimal wastes. This methodology was also extended to the synthesis of peptides and lactams by addition of Hünig's base (DIPEA) and 4-dimethylaminopyridine (DMAP).

Substituted Pyrrololactams via Ring Expansion of Spiro-2H-pyrroles from Intermolecular Alkyne-Isocyanide Click Reactions

The facile synthesis of 6- to 8-membered pyrrololactams has been developed using a ring expansion of spiro-2H-pyrroles, the products of intermolecular alkyne-isocyanide click reactions. The key to successful ring expansion of spiro-2H-pyrroles to pyrrololactams is the enforced orbital overlap between the internal alkene and the amide carbonyl group through the conformationally locked bicyclic structures. The newly disclosed α-isocyano lactams, substrates for click reactions, should find their utility in the synthesis of pharmaceutically important heterocyclic compounds.

Serine protease inhibitors

The invention relates to a compound having the formula (I): R1SO2—B—X—Z—C(O)—Y, B is a bond, an amino acid of the formula —NR—CH[(CH2)pC(O)OH]—C(O)— or an ester derivative thereof wherein p is 1, 2, or 3, Gly, D-1-Piq, D-3-Piq, D-1-Tiq, D-3-Tiq, D-Atc, Aic, or a L- or D-amino acid having a hydrophobic, basic or neutral side chain; X is an amino acid with a hydrophobic side chain, glutamine, serine, theronine, a cyclic amino acid optionally containing an additional heteroatom selected from N, O or S, and optionally substituted with (1-6C)alkyl, (1-6C)alkoxy, benzyloxy or oxo, or X is 2-amino-isobutyric acid, —NR2—CH2—C(O)— or the fragment (I) or (II), wherein n is 2, 3, or 4, W is CH or N and R3is H, (1-6C)alkyl or phenyl which groups may optionally be substituted with hydroxy, (1-6C)alkoxy, COOH, COO(1-6C)alkyl, CONH2, or halogen; Z is lysine or 4-aminocyclohexylglycine. The compounds of the invention have anticoagulant activity and can be used in treating or preventing thrombin-related diseases. The variable R1and Y are defined in claim 1.

Thrombin inhibitors having a lactam at P3

The present invention provides compounds having a lactam ring at P3 and at P1 have a six-membered heterocyclic ring having two ring nitrogen ring atoms and the remainder of the ring atoms carbon atoms. These compounds have biological activity as active and potent inhibitors of thrombin. Their pharmaceutically acceptable salts, pharmaceutical compositions thereof and methods of using these compounds and pharmaceutical compositions comprising these compounds as therapeutic agents for treatment of disease states in mammals which are characterized by abnormal thrombosis are also described.

Parallel liquid synthesis of N,N′-disubstituted 3-amino azepin-2-ones as potent and specific farnesyl transferase inhibitors

A rapid structure-activity study was performed by parallel liquid synthesis on N,N′-disubstitution of 3-amino azepin-2-one to afford potent and specific farnesyl transferase inhibitors with low nM enzymatic and cellular activities. The activities of the selected compounds were validated in vivo, and compounds 41a and 44a presented significant antitumour activity.

Serine protease inhibitors

Serine protease inhibitors, prodrugs thereof and pharmaceutically acceptable salts thereof are disclosed. The serine protease inhibitors exhibit anticoagulant activity and are useful for treating or preventing thrombin related diseases.

Serine protease inhibitors

The invention relates to a cornound having formula (I), wherein A, B, X, Y and r are as defined in the description, or a prodrug thereof or a pharnnaceutically acceptable salt thereof. The compounds of the invention have anticoagulant activity and can be used in treating or preventing thrombin-related diseases.

THROMBIN INHIBITORS

The invention relates to non-slow-binding thrombin inhibitors of the formula: A-B-C-Lys-D wherein A is H, 2-hydroxy-3-cyclohexyl-propionyl-, R1, R1—O—CO—, R1—SO2—, —(CHR2)nCOOR3, or an N-protecting group, wherein R1 is selected from -(1-6C)alkylene-COOH, (1-12C)alkenyl, (6-14C)aryl, (7-15C)aralkyl and (8-16C)aralkenyl, the group of which may be substituted with (1-6C)alkyl, (2-12C)alkoxy, hydroxy, or halogen; R2 is H or has the same meaning as R1, R3 is selected from H, (112C)alkyl, (2-12C)alkenyl, (6-14C)aryl, (7-15C)aralkyl and (8-16C)aralkenyl, the aryl group of which may be substituted with (1-6C)alkyl, (2-12C)alkoxy, hydroxy or halogen; n is an integer of 1 to 3; B is a bond, L-Asp or an derivative thereof, Leu,norLeu, -n(benzyl)—CH2—CO—, -N(2-indane)—CH2—CO—, D-1Piq, D-Tiq, Atc or a D-amino acid having a hydrophobic aromatic side chain; C is Azt, Pro, Pec, norLeu(cyclo)Gly, an amino acid of one of the formulae -N[(3-8C)cycloalkyl]—CH—CO—or -N(benzyl)—CH2—CO —, D is selected from COOH, tetrazole, oxazole,thiazole and benzothiazole, or A znd C have the aforesaid meaning, B is D-(3-8C) cycloalkylalanine, and D is tetrazole, oxazole, thiazole or benzothiazole; or a prodrug thereof; or a pharmaceutically acceptable salt thereof; with the exception of the compound Me-D-Phe-Pro-Lys-COOH. The compounds can be used as antithrombotic agents.

SUBSTITUTED (SULFINIC ACID, SULFONIC ACID, SULFONYLAMINO OR SULFINYLAMINO) N-[(AMINOIMINOMETHYL)PHENYLALKYL]-AZAHETEROCYCLYLAMIDE COMPOUNDS

The compounds of formula I exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More especially, they are Factor Xa inhibitors. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, which are for treating a patient suffering from, or subject to, conditions which can be ameliorated by the administration of an inhibitor of Factor Xa.