- Thermally induced and transition metal catalyzed aza-Claisen rearrangement of 2-cyclopropylideneethyl imidates: A new entry to 1-aminocyclopropanecarboxylic acids
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(2-Cyclopropylideneethyl) acetimidates underwent thermally induced or palladium (II) catalyzed azaClaisen rearrangement into 1-ethenylcyclopropyl acetamides, providing convenient precursors to 1-amino cyclopropanecarboxylic acids (ACCs). Due to the regioselectivity of the nucleophilic substitution of the π 1,1-dimethylene allyl palladium complexes by soft nucleophiles, the palladium (0) catalysis was apparently non effective.
- Estieu, Karine
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- PRODUCTION METHOD FOR 1-AMINO CYCLOPROPANE CARBOXYLIC ACID NONHYDRATE
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1-Aminocyclopropanecarboxylic acid non-hydrate can be obtained by treating 1-aminocyclopropanecarboxylic acid hydrochloride with a tertiary amine in the presence of a C3-C4 alcohol and water, keeping the reaction mixture at 50° C. or below, collecting the precipitated crystal of 1-aminocyclopropanecarboxylic acid 0.5 hydrate by filtration, and contacting the obtained crystal with a C1-C2 alcohol.
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Paragraph 0050-0052
(2021/05/14)
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- PRODUCTION METHOD FOR 1-AMINO CYCLOPROPANE CARBOXYLIC ACID NONHYDRATE
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1-Aminocyclopropanecarboxylic acid non-hydrate can be obtained by treating 1-aminocyclopropanecarboxylic acid hydrochloride with a tertiary amine in the presence of a C3-C4 alcohol and water, keeping the reaction mixture at 50° C. or below, collecting the precipitated crystal of 1-aminocyclopropanecarboxylic acid 0.5 hydrate by filtration, and heating the obtained crystal to 80 to 245° C.
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Paragraph 0042
(2020/04/10)
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- Preparation method of 1-amino-cyclopropanecarboxylic acid
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The invention discloses a preparation method of 1-amino-cyclopropanecarboxylic acid. The method includes: adopting nitroacetonitrile as the starting material, carrying out cyclization and hydrolysis reaction with 1, 2-dibromoethane under the action of potassium carbonate and the phase transfer catalyst tetrabutylammonium bromide to obtain 1-nitro-cyclopropanecarboxylic acid, and then carrying outnitro reduction reaction under the action of a palladium carbon catalyst and hydrogen to obtain 1-amino-cyclopropanecarboxylic acid. The method provided by the invention adopts the new starting material, achieves one-pot two-step reaction of cyclization and hydrolysis, has the advantages of short reaction step, high yield, high product purity and low cost, and is suitable for industrial application.
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Paragraph 0012; 0014; 0016; 0018
(2018/03/26)
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- A 1-amino-cyclopropane-1-carboxylic acid simple synthesis process
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The invention relates to a synthesis process of 1-aminocyclopropane-1-carboxylic acid. According to the process, the 1-aminocyclopropane-1-carboxylic acid is synthesized from nitro acetate and 1,2-dihalo ethane through the reaction of alkylated cyclization, nitro reduction and carboxyl hydrolysis, and a high-content and high-purity product is obtained through carrying out separation, purification and crystallization after the reaction is ended. In the aspects of reagents and raw and auxiliary materials used during the reaction, both environment-friendliness and efficiency are taken into account. The process disclosed by the invention has the advantages of high atom economical efficiency, simple equipment and environment-friendly production procedure and has very large economic and social benefits.
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Paragraph 0023; 0024
(2017/02/24)
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- A α-cycloalanine on the preparation method
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The invention relates to a method for synthesizing alpha-cycloalanine. The method comprises the steps of performing esterification on glycine serving as a raw material, synthesizing esterified product from the former step with p-benzene sulfonyl chloride, performing alkylation reaction on the synthesized product from the former step and 1,2-dibromoethane, and finally hydrolyzing to obtain a product. The method has the advantages of low process pollution, high yield, good purity, low cost and the like, is simple to operate and is a process suitable for industrialized production.
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Paragraph 0015; 0026-0028
(2017/04/29)
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- NOVEL COMPOUND HAVING ABILITY TO INHIBIT 11B-HSD1 ENZYME OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, METHOD FOR PRODUCING SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
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The present invention relates to a novel compound or a pharmaceutically acceptable salt thereof inhibiting 11β-HSD1 enzyme activity, a preparation method of the same, and a pharmaceutical composition comprising the same as an active ingredient. Since the compound of the present invention selectively inhibits the activity of 11β-HSD1 (11β-Hydroxysteroid dehydrogenase type 1), the compound of the invention can be effectively used as a therapeutic agent for the treatment of diseases caused by the over-activation of 11β-HSD1 such as non-insulin dependent type II diabetes, insulin resistance, obesity, lipid disorder, metabolic syndrome, and other diseases or condition mediated by the excessive activity of glucocorticoid.
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Paragraph 0458-0460
(2015/08/04)
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- A COMPOUND FOR INHIBITING 11B-HYDROXY STEROID DEHYDROGENASE 1, AND A PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
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Disclosed are a novel compound or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition including the same for inhibiting human 11-β-hydroxy steroid dehydrogenase type 1 (11β-HSD1). The disclosed compound and the pharmaceutical composition including the same for inhibiting human 11-β-hydroxy steroid dehydrogenase type 1 (11β-HSD1) are excellent in activity and solubility, and is more efficient in formulation and transfer.
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Paragraph 0347-0348
(2014/08/06)
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- A COMPOUND FOR INHIBITING 11BETA-HYDROXY STEROID DEHYDROGENASE 1, AND A PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
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Disclosed are a novel compound or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition including the same for inhibiting human 11-beta-hydroxy steroid dehydrogenase type 1 (11beta-HSD1). The disclosed compound and the pharmaceutical composition including the same for inhibiting human 11-beta-hydroxy steroid dehydrogenase type 1 (11beta-HSD1) are excellent in activity and solubility, and is more efficient in formulation and transfer.
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Paragraph 632-634
(2013/03/26)
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- New quinazolinone alkaloids within rare amino acid residue from coral-associated fungus, aspergillus versicolor LCJ-5-4
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Cottoquinazoline D (3), a new alkaloid with a 1-aminocyclopropane-1- carboxylic acid residue rarely discovered in nature, was isolated and identified together with two new quinazolinone alkaloids, cottoquinazolines B (1) and C (2), from coral-associated fungus Aspergillus versicolor LCJ-5-4. Their structures including absolute configurations were elucidated based on spectroscopic methods, X-ray single crystal diffraction analysis, and chemical methods. A possible biogenetic pathway for them was proposed.(Figure Presented)
- Zhuang, Yibin,Teng, Xiancun,Wang, Yi,Liu, Peipei,Li, Guoqiang,Zhu, Weiming
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supporting information; experimental part
p. 1130 - 1133
(2011/05/16)
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- PEPTIDES AND PEPTIDOMIMETIC COMPOUNDS, THE MANUFACTURING THEREOF AS WELL AS THEIR USE FOR PREPARING A THERAPEUTICALLY AND/OR PREVENTIVELY ACTIVE PHARMACEUTICAL COMPOSITION
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Peptides, peptidomimetics and derivatives thereof of the general formula I: H2N-GHRPX1-β-X4X5X6X7X8X9X10-X11 (I), in which X1-X10 denote one of the 20 genetically coded amino acids, wherein X8, X9 and X10 may also denote a single chemical bond;X11 denotes OR1 in which R1 equals hydrogen or (C1-C10) alkyl NR2R3 with R2 and R3 are equal or different and denote hydrogen, (C1-C10) alkyl, or a residue —W-PEG5-60K, in which the PEG residue is attached via a suitable spacer W to the N-atom, ora residue NH—Y-Z-PEG5-60K, in whichY denotes a chemical bond or a genetically coded amino acids from the group S, C, K or R andZ denotes a spacer, via which a polyethylene glycol (PEG)-residue can be attached, and their physiologically acceptable salts, andβ denotes an amino acid, or a peptidomimetic element, which induces a bend or turn in the peptide backbone.
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- ALPHA KETOAMIDE COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS
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The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.
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Page/Page column 59
(2008/06/13)
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- Purification and production methods of 1-aminocyclopropanecarboxylic acid
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A method purifies 1-aminocyclopropanecarboxylic acid by subjecting a crude 1-aminocyclopropanecarboxylic acid to crystallization with a solvent mixture containing an organic acid having one to five carbon atoms and a poor solvent for 1-aminocyclopropanecarboxylic acid, which poor solvent is miscible with the organic acid. In the method, the solvent mixture may further contain water. Purification may be carried out by mixing the crude 1-aminocyclopropanecarboxylic acid with the organic acid having one to five carbon atoms, removing insoluble matter by filtration, and adding the poor solvent with or without water to the filtrate to thereby crystallize 1-aminocyclopropanecarboxylic acid.
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Page/Page column 3; 4
(2008/06/13)
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- ALPHA KETOAMIDE COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS
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The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.
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Page/Page column 69-70
(2010/11/24)
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- Convenient synthesis and isolation of 1-aminocyclopropane-1-carboxylic acid (ACC) and N-protected ACC derivatives
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A convenient route to 1-aminocyclopropane-1-carboxylic acid (1, ACC) and N-protected derivatives was developed. This route utilizes a bisalkylation of an O-benzyl glycine derived imine followed by global deprotection via hydrogenation. Direct isolation of ACC from a non-aqueous stream or efficient conversion to N-protected derivatives in a single flask is described.
- Allwein, Shawn P.,Secord, Elizabeth A.,Martins, Andrew,Mitten, Jeffrey V.,Nelson, Todd D.,Kress, Michael H.,Dolling, Ulf H.
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p. 2489 - 2492
(2007/10/03)
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- Lactone-containing compounds, polymers, resist compositions, and patterning method
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A novel lactone-containing compound is provided as well as a polymer comprising units of the compound. The polymer is used as a base resin to formulate a resist composition having a high sensitivity, resolution and etching resistance.
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- Partial agonists of the strychnine insensitive glycine modulatory site of the N-methyl-D-aspartate receptor complex as neuropsychopharmacological agents
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A method is disclosed for the treatment of neuropsychopharmacological disorders which are associated with or result from excessive activation of the N-methyl-D-aspartate receptor complex, which method comprises administering an effective neuropsychopharmacological disorder-treating amount of a compound possessing partial agonist properties for the strychnine insensitive glycine modulatory sites of N-methyl-D-aspartate receptors. Exemplary of partial agonists which are useful in the method of the invention are 1-aminocyclopropanecarboxylic acid, and associated derivates thereof. Novel injectable pharmaceutical compositions are also disclosed.
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- A novel synthesis of 1-aminocyclopropane-1-carboxylic acid (ACC)
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A novel synthetic route of 1-aminocyclopropane-1-carboxylic acid (ACC) has been built via cyclopropanedicarboxylic acid monohydrazide II in moderation to good yield.
- Zhu, Xuxiang,Gan, Ping
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p. 3159 - 3162
(2007/10/03)
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- Process for the preparation of 1-aminocyclopropanecarboxylic acid hydrochloride
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The present invention relates to a novel process for preparing 1-aminocyclopropanecarboxylic acid hydrochloride (ACC*HCl) of the formula STR1 ACC*HCl is prepared from a cyclopropane-1,1-dicarboxylic acid diester via an 1-aminocarbonylcyclopropanecarboxylic acid ester intermediate and an alkali metal salt or alkaline earth metal salt of 1-aminocarbonylcyclopropanecarboxylic acid. The process represents a simplification and gives improved product yields.
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- Palladium (O) catalyzed tandem alkylation and SN′ cyclization of 1,4-dichlorobut-2-ene by the N-(diphenylmethylene)acetonitrile. a stereoselective synthesis of 1-aminocyclopropanecarboxylic acids
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Racemic coronamic acid has been prepared with 100% diastereoselectivity from one pot palladium (O) catalyzed alkylation and SN′ cyclization of 1,4-dichlorobut-2-ene by the benzophenone Schiff base of aminoacetonitrile.
- Gaucher, Anne
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p. 2979 - 2982
(2007/10/02)
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- New α,β-Didehydroamino Acid Derivatives as Precursors in the Synthesis of 1-Aminocyclopropanecarboxylic Acids
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The reaction of N-(diphenylmethylene)didehydroalanine methyl ester and N-didehydroalanine methyl ester with diazoalkanes or ylides gives the corresponding cyclopropane derivatives in high yields.The cis/trans ratio of these compounds was dependent on substrate, reagent and reaction temperature.From stereochemically homogeneous compounds the corresponding 1-aminocyclopropanecarboxylic acids were easily obtained by acid hydrolysis.
- Cativiela, Carlos,Diaz-de-Villegas, Maria D.,Jimenez, Ana I.
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p. 9157 - 9166
(2007/10/02)
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- Spiro compound
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The present invention relates to spiro compounds of general formula I: STR1 wherein the substituents are herein below defined. The present invention relates to antibacterial spiro compounds which are of value as drugs for humans, veterinary drugs or drugs for use in fish culture or as preservatives, and to antibacterial compositions containing one or more of the same compounds as active ingredients.
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- 1-Aminocyclopropane-1-carboxylic acid derivatives: A new, general synthesis and NMDA receptor complex binding affinity study
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A new synthesis of 1-aminocyclopropane-1-carboxylic acid and of its (E)- and (Z)-2-substituted analogues (R = CH3;i-Pr;C6H5) has been performed by means of the 'diazo-addition' method, starting from N-(diphenylmethylene)-2,3-dehydro-1-amino-1-carboxylate precursors. The (E)- and (Z)-2-phenyl and the (Z)-2-methylcyclopropaneamino acids have been obtained with high diastereospecificity. All the cyclopropaneamino acids prepared were tested for their affinity for some glutamate receptors and resulted inactive, wich the exception of compounds (E)-1b and (Z)-1c which showed a shallow displacement of [H]-glycine binding.
- Spadoni,Balsamini,Bedini,Mugnaini
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p. 1663 - 1674
(2007/10/02)
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- Regioselective palladium (0) catalyzed azidation and amination of 1-alkenylcyclopropyl esters: A new route to 2,3-methanoamino acids
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Palladium (0) catalyzed azidation of 1-alkenylcyclopropyl esters provides regioselectively 1-azido-1-alkenyl cyclopropanes, convenient precursors of 2,3-methanoamino acids. On the other hand, amination occurred exclusively on the less substituted allylic end, providing strained 2-cyclopropylideneethylamine derivatives.
- Aufranc,Ollivier,Stolle,Bremer,Es-Sayed,De Meijere,Salaun
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p. 4193 - 4196
(2007/10/02)
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- Treatment of mood disorders with functional antagonists of the glycine/NMDA receptor complex
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A method is disclosed for the treatment of mood disorders, including major depression, by administering an effective mood disorder treating amount of a compound possessing functional antagonist properties for the N-methyl-D-aspartate receptor complex.
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- A new and convenient synthesis of 1-aminocyclopropanecarboxylic acid from cyclopropanone acetal
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Cyclopropanone acetal 2a undergoes the one-pot Strecker synthesis under sonication to provide the amino nitrile 8, which after hydrolysis and catalytic hydrogenolysis, gives 1-aminocyclopropanecarboxylic acid (ACC, 1) in good overall yield.
- Fadel
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p. 6265 - 6274
(2007/10/02)
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- A CONVENIENT AND EFFICIENT SYNTHESIS OF 1-AMINOCYCLOPROPANECARBOXYLIC ACID (ACC)
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A straightforward synthesis of 1-aminocyclopropanecarboxylic acid (ACC) has been developed.The key step in the synthesis is the thermal conversion of 1-t-butoxycarbonylcyclopropanecarboxylic acid to ACC.
- Wheeler, Thomas N.,Ray, John A.
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p. 141 - 150
(2007/10/02)
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- A Simple Synthesis of 1-Aminocyclopropane-1-carboxylic Acid
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Conversion of N-carbobenzyloxy-L-glutamic acid α-methylester (Z-L-glu(OH)OCH3, 1) into the bromo derivative 2 and subsequent γ-elimination by the use of sodium hydride leads to the fully protected synthon 3 in good yields.Deprotection by sodium hydroxide and hydrogenolysis yields almost quantitively the key substance 5.
- Strazewski, Peter,Tamm, Christoph
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p. 298 - 299
(2007/10/02)
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- Regioselectivity in the Catalytic Hydrogenolysis of 1-Amino-1-cyclopropanecarboxylic Acid and Its Methyl Ester
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The title compounds were hydrogenolyzed over Pd-C.The ring-bond cleavage in the hydrogenolysis of the acid in water or methanol occurred at both the C1-C2 bond and the C2-C3 bond in nearly equal proportion, whereas the C1-C2 bond was cleaved mainly in the presence of ammonia and the C2-C3 bond was cleaved mainly in acetic acid.Selective hydrogenolysis of the C1-C2 bond of ester occurred in hexane or methanol, whereas the C2-C3 bond was hydrogenolyzed mainly in acetic acid.The role of the amino group is discussed.
- Isogai, Koji,Sakai, Jun-ichi,Yamauchi, Keiji,Watanabe, Katsuya
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p. 2839 - 2842
(2007/10/02)
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- FACILE SYNTHESIS OF D,L-PHOSPHINOTHRICIN FROM METHYL 4-BROMO-2-PHTHALIMIDOBUTYRATE
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Synthetic versatility of the title bromide is illustrated by simple preparations of D,L-phosphinothricin, D,L-2-amino-4-phosphonobutyric acid, and aminocyclopropanecarboxylic acid.
- Logusch, E. W.
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p. 5935 - 5938
(2007/10/02)
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- Regulating plant growth with novel 1-amino-cyclopropanecarboxylic acid metal complexes
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1-Amino-cyclopropanecarboxylic acid metal complexes of the formula STR1 in which R is a hydrogen atom or a radical of the formula --CO--R1, R1 is a hydrogen atom or an alkyl or phenyl radical, and M is a transition metal atom which can assume the coordination number 4 which possess plant growth regulating activity.
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- Stereochemical studies on the reactions catalyzed by the PLP-dependent enzyme 1-aminocyclopropane-1-carboxylate deaminase
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The stereochemical course of 1-aminocyclopropane-1-carboxylate deaminase which catalyzes the fragmentation of the cyclopropane substrate to alpha -ketobutyrate and ammonia has been unraveled with the help of substrates stereospecifically labeled with deuterium and/or tritium, and this has afforded important information about the process occurring at the active site during enzymatic conversion.
- Liu,Auchus,Walsh
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p. 5335 - 5348
(2007/10/07)
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- Process for the preparation of 1-amino-cyclopropane-carboxylic acid compounds
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A process for the preparation of 1-amino-cyclopropane-carboxylic acid or a derivative thereof of the general formula STR1 in which R1 represents hydrogen or alkyl and R2 represents hydrogen or a radical --CO--R3, wherein R3 represents hydrogen, alkyl, aryl or alkoxy, in which a 2-cycloamino-4-methylthio-butanoic acid ester ( acyl-methionine ester ) of the general formula STR2 in which R3 has the meaning indicated above and R4 represents alkyl, is reacted successively with dimethyl sulphate and an alkali metal alcoholate, if appropriate in the presence of a diluent, at a temperature between 80° C. and 150° C., the product is then optionally saponified with aqueous alkali metal hydroxide or alkaline-earth metal hydroxide at a temperature between 70° C. and 150° C., the reaction mixture thereby obtained is acidified with concentrated hydrochloric acid at a temperature between 0° C. and 30° C., and the hydrochloride formed is then treated, in methanolic solution, with propylene oxide at a temperature between -5° C. and +20° C.
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- SYNTHESIS OF 1-AZIDOCYCLOPROPANECARBOXYLATES FROM 2-AZIDO-2-ALKENOATES
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Addition of diazomethane to 2-azido-2-alkenoates followed by pyrolysis of the resulting pyrazoline derivatives affords the title compounds.
- Hiyama, Tamejiro,Kai, Mariko
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p. 2103 - 2104
(2007/10/02)
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- Process for preparing 1-aminocyclopropane-1-carboxylic acid
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An improved process for preparing 1-aminocyclopropane-1-carboxylic acid, which acid is a plant growth regulator.
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