- SUBSTITUTED TRIAZINONES AS THYROID HORMONE RECEPTOR AGONISTS
-
The application relates to a compound of Formula (I') or (I), or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, or tautomer thereof, which modulates the activity of thyroid hormone receptors, a pharmaceutical composition comprising a compound of Formula (I') or (I), and a method of treating or preventing a disease or disorder regulated by thyroid hormone.
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Paragraph 00269-00270
(2021/07/24)
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- TERTIARY AMINE COMPOUND OR IMINE COMPOUND-POLYMER CONJUGATE AND PRODUCTION METHOD THEREFOR
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Provided is a compound obtained by conjugating a tertiary amine compound or imine compound, which is useful as a drug, with a polymer, in which a structure D+ having a quaternary ammonium salt or iminium salt formed from a tertiary amine compound or imine compound D and a polymer residue Poly having a carboxy group are bonded to each other via a structure —C(R1)(R2)OC(O)ANHC(═O)—.
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Paragraph 0134-0136
(2020/05/29)
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- Discovery of Selective Inhibitors of Endoplasmic Reticulum Aminopeptidase 1
-
ERAP1 is an endoplasmic reticulum-resident zinc aminopeptidase that plays an important role in the immune system by trimming peptides for loading onto major histocompatibility complex proteins. Here, we report discovery of the first inhibitors selective for ERAP1 over its paralogues ERAP2 and IRAP. Compound 1 (N-(N-(2-(1H-indol-3-yl)ethyl)carbamimidoyl)-2,5-difluorobenzenesulfonamide) and compound 2 (1-(1-(4-acetylpiperazine-1-carbonyl)cyclohexyl)-3-(p-tolyl)urea) are competitive inhibitors of ERAP1 aminopeptidase activity. Compound 3 (4-methoxy-3-(N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)sulfamoyl)benzoic acid) allosterically activates ERAP1's hydrolysis of fluorogenic and chromogenic amino acid substrates but competitively inhibits its activity toward a nonamer peptide representative of physiological substrates. Compounds 2 and 3 inhibit antigen presentation in a cellular assay. Compound 3 displays higher potency for an ERAP1 variant associated with increased risk of autoimmune disease. These inhibitors provide mechanistic insights into the determinants of specificity for ERAP1, ERAP2, and IRAP and offer a new therapeutic approach of specifically inhibiting ERAP1 activity in vivo.
- Maben, Zachary,Arya, Richa,Rane, Digamber,An, W. Frank,Metkar, Shailesh,Hickey, Marc,Bender, Samantha,Ali, Akbar,Nguyen, Tina T.,Evnouchidou, Irini,Schilling, Roger,Stratikos, Efstratios,Golden, Jennifer,Stern, Lawrence J.
-
p. 103 - 121
(2020/02/20)
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- NLRP3 inflammasome inhibitor and preparation method and application thereof
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The invention relates to a class of 1, 2, 3, 5, 6, 7 hexahydrosymmetric indacene compounds containing one or more substituents., pharmaceutically acceptable salts, esters or hydrates thereof, a preparation method thereof, a pharmaceutical composition containing the compounds, and an application of the compounds as a novel NLRP3 inflammasome inhibitor in preparation of drugs for preventing and/or treating diseases related to NLRP3 inflammasome.
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Paragraph 0098-0099
(2020/11/12)
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- Amine compound for inhibiting SSAO/VAP-1 and application thereof in medicines
-
The present invention relates to an amine compound for inhibiting SSAO/VAP-1 and application thereof in medicines. In particular, the present invention relates to an amine compound for inhibiting a semicarbazide-sensitive oxidase (SSAO) and/or vascular adhesion protein-1 (VAP-1) inhibitor, or a pharmaceutically acceptable salt thereof, a stereoisomer or an/a E/Z isomer, further relates to a pharmaceutical composition containing the amine compound. The invention further relates to the application of the amine compound and the pharmaceutical composition in manufacture of the medicines for treatment of inflammation, inflammation-related diseases and immune diseases.
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Paragraph 0373; 0374; 0375; 0376
(2018/09/08)
-
- A 4, 7 - diaza spiro [2.5] octane -7 - formic acid tert-butyl synthetic method
-
The invention belongs to the technical field of chemical synthesis of N-heterocycle-containing drug intermediates, and particularly relates to a synthesis method of tert-butyl 4,7-diazaspiro[2.5]octyl-7-formate. By using diethyl malonate as a raw material, cyclization reaction, Hofmann reaction, hydrolysis reaction, acylation reaction for recyclization, reduction reaction and the like are performed to conveniently synthesize the target compound product. The method has the advantages of simple synthesis technique, cheap and accessible raw materials, mild reaction conditions, high controllability, low cost and high yield, and is convenient to operate.
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Paragraph 0033; 0041; 0042; 0060
(2019/01/08)
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- NOVEL SUBSTITUTED AMIDES OF TRITERPENE DERIVATIVES AS HIV INHIBITORS
-
The present invention relates to compounds of novel substituted amides of triteripene derivatives of formula (I); or pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable hydrates, tautomers, stereoisomers, prodrugs, compositions or combination thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, X, Y, Z1, Z2, Z3 and formula (II) are as defined herein. The present invention also relates to,, and pharmaceutical compositions comprising compounds of formula (I) useful for the treatment of viral diseases and particularly HIV mediated diseases.
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Page/Page column 30; 31
(2017/02/28)
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- C-3 NOVEL TRITERPENONE WITH C-28 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS
-
Formula (I) The invention relates to C-3 novel triterpenone with C-28 reverse amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
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Page/Page column 46; 47
(2016/11/21)
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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
-
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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- 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
-
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 0088; 0089
(2015/05/06)
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- Synthesis of 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles via the cyclopropyliminium rearrangement of substituted 2-cyclopropylbenzimidazoles
-
2-Cyclopropylbenzimidazole derivatives with various substituents in the small ring undergo cyclopropyliminium rearrangement into 2,3- dihydropyrrolobenzimidazoles substituted at positions 1, 2 or 3. The substrates containing a functional group in position 1 of the cyclopropane ring form products substituted at position 3. Substituents at position 2 in most cases lead to the formation of a mixture of isomers. The reaction can be directed to yield one of the isomers predominantly by varying the solvent polarity.
- Salikov, Rinat F.,Platonov, Dmitry N.,Frumkin, Aleksandr E.,Lipilin, Dmitry L.,Tomilov, Yury V.
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supporting information
p. 3495 - 3505
(2013/04/23)
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- HYDANTOIN DERIVATIVES USEFUL AS KV3 INHIBITORS
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The invention provides compounds of formula (I): Said compounds being inhibitors of Kv3 channels and of use in the prophylaxis or treatment of related disorders.
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-
Paragraph 0693-0695
(2013/10/22)
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- HYDANTOIN DERIVATIVES USEFUL AS KV3 INHIBITORS
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The invention provides compounds of formula (I): Said compounds being inhibitors of Kv3 channels and of use in the prophylaxis or treatment of related disorders.
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Page/Page column 95
(2012/06/30)
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- IMIDAZOLIDINEDIONE DERIVATIVES
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The invention provides a compound of formula (Ia), and pharmaceutically acceptable salts thereof. The invention also provides use of the compounds or salts as modulators of Kv3.1 and/or Kv3.2, and in the treatment of diseases or disorders where a modulator of Kv3.1 and/or Kv3.2 is required, such as depression and mood disorders, hearing disorders, schizopherenea, substance abuse disorders, sleep disorders or epilepsy.
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Page/Page column 80
(2011/06/26)
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- Titanium-catalyzed cyclopropanation of Boc-protected cyanohydrins: A short access to aminocyclopropanecarboxylic acid derivatives
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The preparation of protected 1-aminocyclopropanecarboxylic acid was performed from readily available and inexpensive starting materials, using titanium-catalyzed cyclopropanation as the key step. As an extension of this methodology, a diastereoselective synthesis of the cis-2-vinyl-substituted analogue is presented. Georg Thieme Verlag Stuttgart.
- Pearson-Long, Morwenna S.M.,Beauseigneur, Alice,Karoyan, Philippe,Szymoniak, Jan,Bertus, Philippe
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experimental part
p. 3410 - 3414
(2010/11/19)
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- ALPHA-UNSUBSTITUTED ARYLMETHYL PIPERAZINE PYRAZOLO[1,5-A] PYRIMIDINE AMIDE DERIVATIVES
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Methods of preventing, treating or delaying the onset of HIV in a subject by administering to the subject novel pharmaceutically active arylmethyl pyrazolo[1,5-α ]pyrimidine amide derivatives, or pharmaceutical compositions containing the same are described. Additionally, compounds of novel pharmaceutically active arylmethyl piperazine pyrazolo[l,5-α]pyrimidine amide derivatives and their use for the manufacture of specific medicaments are described.
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Page/Page column 180
(2008/12/08)
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- Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders
-
The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.
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Page/Page column 50
(2010/11/26)
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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 70
(2010/11/24)
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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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- Synthesis of spirocyclopropanated analogues of iprodione
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Methyl 1-(tert-butoxycarbonylamino)cyclopropanecarboxylate (9) was converted into the spirocyclopropanated five-membered ring analogue 7a of Iprodione (1) in five steps with an overall yield of 28%. The spirocyclopropanated five-membered ring analogue 8a was prepared from tert-butyl N-[1-(hydroxymethyl)cyclopropyl]carbamate (10) in five steps with an overall yield of 19%. En route to the spirocyclopropanated six-membered ring analogues of Iprodione (1), the oxalic acid diamides 5b and 6b could be obtained starting from 9 or 10 in 33 or 19% yield, respectively. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
- Brackmann, Farina,Es-Sayed, Mazen,De Meijere, Armin
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p. 2250 - 2258
(2007/10/03)
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- Convenient synthesis and isolation of 1-aminocyclopropane-1-carboxylic acid (ACC) and N-protected ACC derivatives
-
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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- Ti(II)-mediated conversion of α-heterosubstituted (O, N, S) nitriles to functionalized cyclopropylamines. Effect of chelation on the cyclopropanation step
-
α-Alkoxy, amino-, and thio nitriles undergo a Ti(II)-mediated coupling with Grignard reagents to afford heterofunctionalized cyclopropylamines. A chelation effect appears to be generally responsible for the spontaneous contraction of the intermediate azatitanacycle leading to cyclopropane. By using the described reaction, 1-aminocyclopropanecarboxylic acids were prepared in four steps, in good overall yields, from the readily available benzyloxyacetonitrile.
- Bertus, Philippe,Szymoniak, Jan
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p. 3965 - 3968
(2007/10/03)
-
- Cyclopropyl building blocks for organic synthesis, 58(+): A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzylcarboxamides
-
Our recently reported titanium-mediated transformation of N,N-dialkylcarboxamides to cyclopropylamines has been applied to N,N-dibenzyl-2-benzyloxyacetamide using a variety of alkylmagnesium bromides to yield 1-(benzyloxymethyl)-1-(dibenzylamino)cyclopropane (15a, 48percent) and 2-substituted analogs 15b-f (33-48percent). These have been transformed in just a few steps into N-Boc-protected methyl esters of 1-aminocyclopropanecarboxylic acid (1, 29percent overall), coronamic acid (2, 35percent) and norcoronamic acid (21percent), 2,3-methanoglutamic acid (21g, 19percent) and 2,3-methanoornithine (211, 12percent). Similarly, the corresponding derivatives of 3,4-methano-γ-aminobutyric acid (26, 23percent) and 4-spirocyclopropane-γ-butyrolactam (32, 44percent) have been synthesized.
- Kordes, Markus,Winsel, Harald,De Meijere, Armin
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p. 3235 - 3245
(2007/10/03)
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- N-AROYLAMINO ACID AMIDES AS ENDOTHELIN INHIBITORS
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The present invention relates to the compounds of formula (I) STR1 wherein R is carboxy, esterified carboxy, carbamoyl, N-(alkyl or aryl)-carbamoyl, cyano, 5-tetrazolyl or CONH--SO 2--R 4 ; R. sub.1 is hydrogen, lower alkyl, aryl-lower alkyl or cycloalkyl-lower alkyl; R 2 is hydrogen or lower alkyl, or R 1 and R 2 represent lower alkylene to form together with the carbon and nitrogen atoms to which they are attached an azacycloalkane ring; R 3 is heterocyclic or carbocyclic (aryl or biaryl)-lower alkyl; Y is lower alkylidenyl, 3-to 10-membered cycloalkylidenyl which may be substituted by oxo, alkylenedioxy, hydroxy, acyloxy, lower alkoxy; or Y is 5-to 10-membered cycloalkylidenyl fused to a saturated or unsaturated carbocyclic 5-or 6-membered ring; or Y is 5-to 8-membered oxacycloalkylidenyl, 5-to 8-membered (thia-, oxothia-or dioxothia-) cycloalkylidenyl, or 5-to 8-membered azacycloalkylidenyl optionally N-substituted by lower alkyl or aryl-lower alkyl; R 4 represents hydrogen, lower alkyl, carbocyclic aryl, heterocyclic aryl, cycloalkyl, (carbocyclic aryl, heterocyclic aryl, cycloalkyl, hydroxy, acyloxy, or lower alkoxy)-lower alkyl, lower alkyl substituted by carboxyl, by esterified carboxyl or by amidated carboxyl; Ar represents carbocyclic or heterocyclic aryl; and pharmaceutically acceptable salts thereof; which are useful as endothelin inhibitors in mammals.
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-
-
- An efficient and high yield method for the N-tert-butoxycarbonyl protection of sterically hindered amino acids
-
An important method for the N-tert-butoxycarbonyl protection of the amino functionality of α-alkylated prolines and other sterically hindered α,α-disubstituted amino acids has been developed in which the lipophilic base tetramethylammonium hydroxide is used to solubilize the otherwise insoluble zwitterionic amino acid in acetonitrile, thereby obviating the need for an aqueous medium.
- Khalil, Ehab M.,Subasinghe, Nalin L.,Johnson, Rodney L.
-
p. 3441 - 3444
(2007/10/03)
-
- Ethylene biosynthesis. 12. Analog approach to the active site topography of the ethylene-forming enzyme. Novel hydroxamate inhibitors
-
In order to understand both the substrate specificity and active site topography of the ethylene-forming enzyme (EFE), a number of analogs of its substrate, 1-aminocyclopropanecarboxylic acid, have been prepared and studied as inhibitors. Because of the dependence of EFE activity on iron, hydroxamic acids, a functional group known to bind iron tightly, derived from several small carboxylic/amino acids were studied along with the parent amino acids. The activity of these materials was assayed in vitro against the purified EFE from apple fruit. The varying potency of the amino acid hydroxamates suggests that they do not act simply by binding to iron and removing it from the enzyme. The order of their potency was consistent with the idea that binding reflects both metal chelation and hydrophobic interactions in the active site. The most potent inhibitor, ACC-hydroxamate, has about 1 μM K(i).
- Pirrung,Cao,Chen
-
p. 5790 - 5794
(2007/10/03)
-
- Latent inhibitors part 10. The inhibition of carboxypeptidase A by tetrapeptide analogues based on 1-aminocyclopropane carboxylic acid
-
In order to test the phenomenon of substrate activation of irreversible inhibition of carboxypeptidase A, extended inhibitors were designed. The synthesis of two N-protected tetrapeptide analogues containing C-terminal sulphones and 1-aminocyclopropane carboxylic acid and one similar N-unprotected tetrapeptide with C-terminal phenylalanine is described. The compounds were evaluated as inhibitors of carboxypeptidase a. The tetrapeptide sulphones exhibited time-dependent inhibition following the unusual 'substrate activated' pattern of related dipeptides but the phenylalanine containing dipeptide behaved as a mixed non-competitive inhibitor. A molecular modelling evaluation of the potential of aminocyclopropane carboxylic acid derivatives to act as irreversible inhibitors of peptidases was undertaken in an attempt to identify the properties of such compounds that lead to the unusual kinetic properties. A mechanism for the inhibition reactions of dipeptide and tetrapeptide analogues is proposed.
- Husbands,Suckling,Suckling
-
p. 9729 - 9742
(2007/10/02)
-
- Spiro compound
-
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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-
-
- Regioselective palladium (0) catalyzed azidation and amination of 1-alkenylcyclopropyl esters: A new route to 2,3-methanoamino acids
-
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
-
p. 4193 - 4196
(2007/10/02)
-
- A New Synthesis of Coprine and O-Ethylcoprine
-
Coprine (1), a toxine of the mushroom Coprinus atramentarius, was synthesized starting from the 2-amino- and 1-carboxy-protected L-glutamic acids 4 and 12.Compound 4 was first decarboxylated by radical chain reaction to bromide 5 which underwent ring closure to cyclopropanecarboxylate 6 on treatment with NaH (Scheme 1).Subsequent oxidative electrolysis of 7 to form tert-butyl N-(1-ethoxycyclopropyl)carbamate (8) and acidic hydrolysis yielded the 1-aminocyclopropanol hydrochloride (9).Selective cleavage of the amino-protecting group of 8(-> 10 or 11), coupling of the corresponding amine 13 with L-glutamic acid 12, and acidic hydrolysis of the resulting L-glutamine derivative 17 yielded O-ethylcoprine (3) and coprine (1).
- Kienzler, Thomas,Strazewski, Peter,Tamm, Christoph
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p. 1078 - 1084
(2007/10/02)
-
- Reaction of Cyclopropanamines with Hypochlorite
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Ethylene was formed in 65percent yield when 1-(1-piperidino)cyclopropanol 6, was treated with hypochlorite.This observation raised the possibility that 1-aminocyclopropanecarboxylic acids (ACCs) could yield ethylene by a mechanism that involves (1) decarboxylation to a 1-aminocyclopropanol, followed by (2) a fragmentation of the carbinolamine to ethylene induced by a hypochlorite equivalent.Although this mechanism could be ruled out only for 1e, no evidence could be found for it in the reactions of other ACCs, 1a-f, with hypochlorite.The fact that 1b-cis-2,3-d2 yieldedonly ethylene-cis-1,2-d2 is consistent with either the mechanism described above or a nitrenium ion mechanism.In the reaction of cyclopropanamines with neutral hypochlorite, ethylene is not the major product.From the primary and secondary amino acids 1a-c, a 3-hydroxypropanenitrile or propanamide, 2a-c, probably the product of a nucleophilic ring-opening step followed by decarboxylation, is formed.Similar products are formed from other cyclopropanamines: 2a from 1g, 2d from 1h, 2e and 2f from 1i, and lactone 5 from 1j.
- Vaidyanathan, Ganesan,Wilson, Joseph W.
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p. 1815 - 1820
(2007/10/02)
-
- L-aminodicarboxylic acid esters
-
Sweeteners of the formula: STR1 and food-acceptable salts thereof, where the substituents are disclosed herein.
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-
-
- A CONVENIENT AND EFFICIENT SYNTHESIS OF 1-AMINOCYCLOPROPANECARBOXYLIC ACID (ACC)
-
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.
-
p. 141 - 150
(2007/10/02)
-
- A New Synthesis of Racemic Coronamic Acid and Other Cyclopropyl Amino Acids
-
A new method, in which various diazocompounds are added to a dehydro alanine derivative, allows the synthesis of coronamic acid and several other cyclopropyl amino acids.
- Suzuki, M.,Gooch, E. E.,Stammer, C. H.
-
p. 3839 - 3840
(2007/10/02)
-