- Rapid and Effective Reaction of 2-Methylpyridin-N-oxides with Triphosgene via a [3,3]-Sigmatropic Rearrangement: Mechanism and Applications
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A facile and effective synthesis of 2-chloromethylpyridines was developed by a one-pot reaction of 2-alkylpyridin-N-oxides and triphosgene at room temperature. As starting materials, N-oxides of 2-alkylpyridine derivatives, including 2-alkylpyridines, 2-methyl quinolines, and phenanthroline, can react rapidly with triphosgene in the presence of triethylamine, affording 2-chloromethylpyridines in good to excellent yields (52-95%). Using the 2-methylquinoline substrate for the mechanistic study, it has been well demonstrated that the chlorination reaction undergoes a [3,3]-sigmatropic rearrangement, which can be observed as a reversible process by monitoring the intermediates. Moreover, the chlorination reaction can be used to construct a rapid and sensitive fluorescent probe for the detection of phosgene.
- Li, Hao,Nie, Fang-Yuan,Song, Qin-Hua,Xia, Hong-Cheng
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supporting information
p. 8308 - 8318
(2021/06/28)
-
- N -Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N -chlorosuccinimide
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The direct chlorination of C-H bonds has received considerable attention in recent years. In this work, a metal-free protocol for hydrocarbon C-H bond chlorination with commercially available N-chlorosuccinimide (NCS) catalyzed by N-hydroxyphthalimide (NHPI) with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) functioning as an external radical initiator is presented. Aliphatic and benzylic substituents and also heteroaromatic ones were found to be well tolerated. Both the experiments and theoretical analysis indicate that the reaction goes through a process wherein NHPI functions as a catalyst rather than as an initiator. On the other hand, the hydrogen abstraction of the C-H bond conducted by a PINO species rather than the highly reactive N-centered radicals rationalizes the high chemoselectivity of the monochlorination obtained by this protocol as the latter is reactive towards the C(sp3)-H bonds of the monochlorides. The present results could hold promise for further development of a nitroxy-radical system for the highly selective functionalization of the aliphatic and benzylic hydrocarbon C-H.
- Li, Zi-Hao,Fiser, Béla,Jiang, Biao-Lin,Li, Jian-Wei,Xu, Bao-Hua,Zhang, Suo-Jiang
-
supporting information
p. 3403 - 3408
(2019/04/01)
-
- Copper(II) catalyzed heterobenzylic C(sp3)-H activation: Two efficient halogenation methodologies towards heterobenzyl halides
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Two practical and simple synthetic methodologies towards various heterobenzyl halides were developed. A series of 2-halomethylquinolines were readily prepared by the one-pot reaction of 2-methylquinolines with CuX (X = I, Br, Cl) and TBHP in CH3CN. A large variety of heterobenzyl iodides, including 2-iodomethylquinolines, 2-iodomethylquinoxalines, 2-iodiomethylbenzooxazole, and 2-iodiomethylbenzothiazole, were efficiently synthesized by one-pot reaction of 2-methylheterocycles with iodine in the presence of CuSO4·5H2O in CH3CN.
- Bi, Wen Zhu,Qu, Chen,Chen, Xiao Lan,Wei, Sheng Kai,Qu, Ling Bo,Liu, Shu Yun,Sun, Kai,Zhao, Yu Fen
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p. 1908 - 1917
(2018/03/13)
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- NOVEL INHIBITOR COMPOUNDS OF PHOSPHODIESTERASE TYPE 10A
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The present invention relates to compounds of the formula (I), the N-oxides, tautomers, the prodrugs and the pharmaceutically acceptable salts thereof. In formula I the variables Het, A, X, Y, Z, R1, R2, R3, R4, R5 and Q are as defined in the claims. The compounds of the formula I, the N-oxides, tautomers, the prodrugs and the pharmaceutically acceptable salts thereof are inhibitors of phosphodiesterase type 10A. Thus, the invention also relates to the use of the compounds of the formula I, the N-oxides, tautomers, the prodrugs and the pharmaceutically acceptable salts thereof for the manufacture of a medicament and which thus are suitable for treating or controlling of medical disorders selected from neurological disorders and psychiatric disorders, for ameliorating the symptoms associated with such disorders and for reducing the risk of such disorders.
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Page/Page column 72
(2014/09/29)
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- Microwave-assisted α-halogenation of 2-methylquinolines with tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane)
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A simple and efficient methodology permitting the halogenation of 2-methylquinolines into 2-(chloromethyl)quinolines or 2-(bromomethyl)quinolines in the tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane) system has been developed for the first time. The halogenation can be rapidly completed with good to excellent yields and high selectivity under microwave irradiation.
- Xie, Yuanyuan,Li, Lehuan
-
supporting information
p. 3892 - 3895
(2014/07/08)
-
- NOVEL INHIBITOR COMPOUNDS OF PHOSPHODIESTERASE TYPE 10A
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The present invention relates to novel carboxamide compounds, pharmaceutical compositions containing them, and their use in therapy. The compounds possess valuable therapeutic properties and are particularly suitable for treating or controlling medical disorders selected from neurological disorders and psychiatric disorders, for ameliorating the symptoms associated with such disorders and for reducing the risk of such disorders
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- Synthesis of new chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives via asymmetric hydrogenation of substituted quinolines
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The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee.
- Maj, Anna M.,Suisse, Isabelle,Hardouin, Christophe,Agbossou-Niedercorn, Francine
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p. 9322 - 9328
(2013/10/01)
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- BICYCLIC HETEROARYL COMPOUNDS AS PDE10 INHIBITORS
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The invention pertains to tricyclic heteraaryi compounds that serve as effective phosphodiesterase (PDE) inhibitors. The invention also relates to compounds which are selective inhibitors of PDE 10. The invention further relates to pharmaceutical compositions comprising such compounds; and the use of such compounds in methods for treating certain central nervous system (CNS) or other disorders. The invention relates also to methods for treating neurodegenerative and psychiatric disorders, for example psychosis and disorders comprising deficient cognition as a symptom.
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Page/Page column 19
(2009/07/18)
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- Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: New room temperature blue emitters
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A series of five 2-heteroarylcyanoximes such as: α-oximino-(2- benzimidazolyl)acetonitrile (HBIHCO), α-oximino-(N-methy-l-2- benzimidazolyl)acetonitrile (HBIMCO), α-oximino-(2-benzoxazolyl) acetonitrile (HBOCO), α-oximino-(2-benzothiazolyl)acetonitrile (HBTCO) and α-oximino-(2-quinolyl)acetonitrile (HQCO) and their monovalent thallium(i) complexes were synthesized and characterized using spectroscopic methods (1H, 13C NMR, IR, UV-visible, mass-spectrometry) and X-ray analysis. The HBIMCO (as monohydrate) adopts planar trans-anti configuration in the solid state. The crystal structure of "HBOCO" revealed the presence of nitroso anion a, BOCO-, and protonated oxime cation b, H2BOCO+, that form a H-bonded dimer in the unit cell. Both molecules adopt planar structures, but different configurations: cis-anti in the molecule a, and trans-anti for b. This is the first reported case of a zwitterionic pair in oximes and the coexistence of the two geometrical cis/trans isomers in the same crystal. All 2-heteroarylcyanoximes form yellow anions upon deprotonation, which exhibit significant negative solvatochromism in solution. Heterogeneous reactions between hot aqueous solutions of Tl 2CO3 and solid protonated 2-heteroarylcyanoximes HL afford yellow TlL. The crystal structure of Tl(BTCO) shows the formation of centrosymmetrical dimers, which connect with each other to form a double-stranded one-dimensional coordination polymer. The oxygen atom of the oxime group acts as a bridge between the three different Tl(i) centers. The anion is non-planar and adopts a trans-anti configuration in the complex. The polymeric motif in the complex represents a ladder-type structure. Staggered π-π interactions between benzothiazolyl groups provide additional stabilization of the structure. Both organic ligands and their Tl(i) complexes exhibit strong room temperature blue emission in the solid state.
- Ilkun, Olesya T.,Archibald, Stephen J.,Barnes, Charles L.,Gerasimchuk, Nikolay,Biagioni, Richard,Silchenko, Svitlana,Gerasimchuk, Olga A.,Nemykin, Victor N.
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supporting information; scheme or table
p. 5715 - 5729
(2009/02/07)
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- Therapeutic uses of tri-aryl acid derivatives
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The use of triaryl acid derivatives of formula (I) and their pharmaceutical compositions as PPAR ligand receptor binders. The PPAR ligand receptor binders of this invention are useful as agonists or antagonists of the PPAR receptor.
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Page/Page column 215
(2010/10/20)
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- Fused imidazole derivatives for improving oral bioavailability of pharmaceutical agents
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This invention concerns the use of compounds of formula the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein the dotted line is an optional bond; n is 1 or 2; R1is hydrogen; halo; formyl; C1-4alkyl optionally substituted with hydroxy, C1-4alkyloxy, C1-4alkylcarbonyloxy, imidazolyl, thiazolyl or oxazolyl; or a radical of formula —X—COOR5, —X—CONR6R7or —X—COR10wherein —X—is a direct bond, C1-4alkanediyl or C2-6alkenediyl; R5is hydrogen, C1-12alkyl, Ar, Het, C1-6alkyl substituted with C1-4alkyloxy, aryl or heteroaryl; R6and R7each independently are hydrogen or C1-4alkyl; R2is hydrogen, halo, C1-4alkyl, hydroxyC1-4alkyl, C1-4alkyloxycarbonyl, carboxyl, formyl or phenyl; R3is hydrogen, C1-4alkyl or C1-4alkyloxy; R4is hydrogen, halo, C1-4alkyl, C1-4alkyloxy or haloC1-4alkyl; Z is —CH2—, —CH2—CH2—, —CH═CH—, —CHOH—CH2—, —O—CH2—, 13 C(═O)—CH2—or —C(═NOH)—CH2—; —A—B—is a bivalent radical; A1is a direct bond, optionally substituted C1-6alkanediyl, C1-6alkanediyl-oxy-C1-6alkanediyl, carbonyl, C1-6alkanediylcarbonyl, optionally substituted C1-6alkanediyloxy; A2is a direct bond or C1-6alkanediyl; and Q is aryl; for the manufacture of a medicine for improving the bioavailability of a second pharmaceutical agent which is co-administered orally to a warm-blooded animal.
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- A simple, regioselective synthesis of 1,4-bis(tert-butoxycarbonylmethyl)-tetraazacyclododecane
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A convenient synthetic route to 1,4-bis(tert-butoxycarbonylmethyl)tetraazacyclododecane (cyclen) (1) with high yield and excellent regioselectivity is described. Compound 1 reacted with a range of functionalized alkyl halides under two reaction conditions to give mono-N-alkylated 1,4-bis(tert-butoxycarbonylmethyl)tetraazacyclododecane (2-9) in good yield.
- Li, Cong,Wong, Wing-Tak
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p. 2956 - 2959
(2007/10/03)
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- Fluorescent monomers
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Fluorescent monomers are described and claimed.
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- Fused imidazole derivatives as multidrug resistance modulators
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This invention concerns the compounds of formula the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein the dotted line is an optional bond; n is1or2; R1is hydrogen; halo; formyl; C1-4alkyl optionally substituted with hydroxy, C1-4alkyloxy, C1-4alkylcarbonyloxy, imidazolyl, thiazolyl or oxazolyl; or a radical of formula —X—COOR5, —X—CONR6R7or —X—COR10wherein —X— is a direct bond, C1-4alkanediyl or C2-6alkenediyl; R5is hydrogen, C1-12alkyl, Ar, Het, C1-6alkyl substituted with C1-4alkyloxy, aryl or heteroaryl; R6and R7each independently are hydrogen or C1-4alkyl; R2is hydrogen, halo, C1-4alkyl, hydroxyC1-4alkyl, C1-4alkyloxycarbonyl, carboxyl, formyl or phenyl; R3is hydrogen, C1-4alkyl or C1-4alkyloxy; R4is hydrogen, halo, C1-4alkyl, C1-4alkyloxy or haloC1-4alkyl; Z is —CH2—, —CH2—CH2—, —CH═CH—, —CHOH—CH2—, —O—CH2—, —C(═O)—CH2— or —C(═NOH)—CH2—; —A—B— is a bivalent radical; A1is a direct bond, optionally substituted C1-6alkanediyl, C1-6alkanediyl-oxy-C1-6alkanediyl, carbonyl, C1-6alkanediylcarbonyl, optionally substituted C1-6alkanediyloxy; A2is a direct bond or C1-6alkanediyl; and Q is aryl. Processes for preparing said products, formulations comprising said products and their use as a medicine are disclosed, in particular for inhibiting or reversing the effects of multidrug resistance.
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- Efficient pyridinylmethyl functionalization: Synthesis of 10,10-bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an acetylcholine release enhancing agent
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2-Fluoro-4-methylpyridine (3) is efficiently functionalized by chlorination, hydrolysis and methane-sulfonylation into the novel alkylating agent 7. This mesylate is used for the bisalkylation of anthrone under carefully defined conditions to prepare the cognition enhancer drug candidate 1. This process proceeds in up to 37% overall yield and is adaptable for large scale synthesis.
- Pesti,Huhn,Yin,Xing,Fortunak,Earl
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p. 7718 - 7722
(2007/10/03)
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- Bis-heteroarylylmethoxyphenyl ketone derivatives as inhibitors of leukotriene biosynthesis
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Compounds having the formula STR1 or a pharmaceutically acceptable salt thereof wherein W is selected from the group consisting of optionally substituted quinolyl, optionally substituted benzothiazolyl, optionally substituted benzoxazolyl, optionally substituted benzimidazolyl, optionally substituted quinoxalyl, optionally substituted pyridyl, optionally substituted pyrimidyl, and optionally substituted thiazolyl; R1 and R2 are one or more groups independently selected from hydrogen, alkyl, halolalkyl, alkoxy, and halogen; Z is selected from the group consisting of N--OH, N--O--A--COM, CH--COM, and CH--CH=N--0--A--COM wherein A is selected from the group consisting of alkylene, alkenylene, cycloalkylene, and optionally substituted alkylphenyl wherein the alkyl portion is of one to six carbon atoms, and M is selected from the group consisting of a pharmaceutically acceptable, metabolically clearable group, --OR3, and --NR4 R5, inhibit leukotriene biosynthesis and are useful in the treatment of allergic and inflammatory disease states. Also disclosed are leukotriene biosynthesis inhibiting compositions and a method of inhibiting leukotriene biosynthesis.
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- Nickel(0)-catalyzed couplings of vinyl- alanes and -zirconocenes with chloromethylated heteroaromatics: A route to E-allylated heterocycles
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Treatment of selected chloromethylated heteroaromatics, including pyridines, thiophenes, and furans, with vinyl alanes or vinyl zirconocenes in the presence of Ni(O) results in E-allylated products in good yields.
- Lipshutz, Bruce H.,Kim, Sung-Kyu,Mollard, Paul,Blomgren, Peter A.,Stevens, Kirk L.
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p. 6999 - 7012
(2007/10/03)
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- Triazolylated teritiary amine compound or salt thereof
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A triazolylated tertiary amine compound represented by general formula (I) or a salt thereof, having an aromatase inhibitory activity and being useful for preventing and treating breast cancer, mastopathy, endometriosis, prostatomergaly, etc., wherein A represents a single bond, lower alkylene or carbonyl; B represents lower alkyl, aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; D represents aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; and E represents 4H-1,2,4-triazolyl, 1H-1,2,4-triazolyl or 1H-1,2,3-triazolyl.
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- A convergent synthesis of an LTD4 antagonist, RG12525
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An efficient, convergent synthesis of an LTD4 antagonist, RG12525 (1) has been achieved through the alkylation of the (2-quinolinylmethoxy)phenol (2) with either a triphenylmethyl protected tetrazole synthon (4a) or with a tetrahydropyranyl derivative (4b). Preparation of synthons 4a and 4b, as well as novel preparation of 2 is described.
- Sledeski, Adam W.,O'Brien, Michael K.,Truesdale, Larry K.
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p. 1129 - 1132
(2007/10/03)
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- Optionally substituted pyrido[2,3-d]pyridine-2,4(1H,3H)-diones and pyrido[2,]pyrimidine-2(1H,3H)-ones
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The present invention relates to optionally substituted pyrido[2,3-d]pyrimidine-2,4(1H,3H)-diones or optionally substituted pyrido[2,3-d]pyrimidine-2(1H,3H)-ones, i.e., compounds of Formula I: STR1 wherein: Y is --CH2 -- or --C(O)--; R1 is hydrogen or --(CH2)n --R7, wherein: R7 is aryl or heteroaryl, and n is 1 or 2, provided that when Y is --C(O)--, R7 is heteroaryl; and R2, R3, R4, R5 and R6 are hydrogen, or one is selected from lower alkyl, halo, carboxy, methoxycarbonyl, carbamoyl, methylcarbamoyl, di-methylcarbamoyl, methylcarbonyl, methylthio, methylsulfinyl, methylsulfonyl, hydroxymethyl, amino, trifluoromethyl, cyano or nitro; or R2, R3, R4 and R5 are independently selected from hydrogen, lower alkyl, nitro, chloro, fluoro, methoxycarbonyl or methylcarbonyl, provided at least one is hydrogen, and R6 is hydrogen; or a pharmaceutically acceptable ester, ether or salt thereof.
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-
- Quinolinoxy phenylsulphonamides
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New phenylsulphonamide of the formula in which STR1 R1 represents a pyridyl, quinolyl or isoquinolyl radical which is unsubstituted or substituted by halogen, alkyl, cycloalkyl, alkoxy, cyano, nitro, halogenoalkyl, halogenoalkoxy, alkoxycarbonyl or alkylsulphonyl, R2 represents hydrogen, cyano, nitro, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or alkoxycarbonyl, R3 represents an aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, halogenoalkyl, halogenoalkoxy, alkyl, alkoxy, alkylthio, alkylsulphonyl, cyano, nitro or alkoxycarbonyl, the substituents being identical or different, or represents pentafluorophenyl or represents a straight-chain, branched or cyclic alkyl which is unsubstituted or substituted by halogen, aryl, aryloxy, cyano, alkoxycarbonyl, alkoxy, alkylthio or trifluoromethyl, and X represents an --O--, --A--B-- or --B--A-- group where A denotes --O--, STR2 and B denotes --CH2 -- or STR3 where R1 does not represent a pyridyl radical when x represents an --O-- group, and salts thereof are prepared by reacting appropriate amines with sulphonyl halides. The substituted phenylsulphonamides can be employed as active compounds for inhibiting enzymatic reactions and for inhibiting thrombocyte aggregations.
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- 4(3H)-quinazolinone derivatives and pharmaceutical compositions
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4(3H)-Quinazolinone derivatives of formula (I) are provided. STR1 wherein R1 is a hydrogen atom, a C1 -C6 alkyl group, an aryl group, a substituted aryl group, or an aralkyl group; R2 is a C1 -C6 alkylamino group, a phenyl group, a substituted phenyl group, or a 5- or 6-membered heterocyclic group containing one or more N, O or S as a hetero atom or atoms, said heterocyclic group optionally being substituted or fused with a benzene ring; n is 1 or 2; or R2 represents a geranyl group or a dipyridylmethyl group together with the group --(CH2)n --; and X is a hydrogen atom, a C1 -C6 alkyl group or a halogen atom, and pharmaceutically acceptable acid addition salts thereof. They are useful as antiulcer agents.
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- Side chain chlorination process of heterocycles
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A novel method of chlorinating the alkyl side chains of a nitrogen containing heterocyclic comprising reacting an alkyl substituted heterocycle with trichloroisocyanuric acid at temperatures of 20° to 200° C. to obtain the same in high yields.
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- Side Chain Chlorinations of N-Heterocyclic Compounds by Trichloroisocyanuric Acid (TCC)
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N-Heterocyclic compounds such as 2-methylpyridines, 2-methylquinoline, and 2-methylquinoxaline react with trichloroisocyanuric acid (TCC) without the addition of an initiator to provide the corresponding chloromethyl derivatives in good yields.
- Jeromin, Guenter E.,Orth, Winfried,Rapp, Bernd,Weiss, Wolfgang
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p. 649 - 652
(2007/10/02)
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- SYNTHESIS OF CYANO OXIMES BASED ON AZOLES AND AZINES AND THE EFFECT OF THEIR PROTON-ACCEPTING CHRACTERISTICS ON THE STABILITY OF THE COMPLEXES OF THE LIGANDS WITH THE Fe(II) ION
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In the series of ligand systems based on ?-deficient azoles and azines with a hydroxyiminocyanomethyl complexing group at the α position to the pyridine-type nitrogen atom the basicity of the heterocyclic nitrogen atom decreases during benzannelation.A comparative assesment was made of the complexing capacity of cyano oximes and the stability of their chelate compounds with the Fe(II) ion.
- Chernov'yants, M. S.,Gus'kova, T. V.,Chernoivanova, T. M.,Bagdasarov, K. N.,Tsupak, E. B.
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p. 1993 - 1997
(2007/10/02)
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- Studies on 1,3-Benzoxazines. II. New Rearrangement Modes in the Reaction of 4-Chloro-2,2-dimethyl-2H-1,3-benzoxazine with Substituted Pyridine N-Oxides
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New rearrangement modes in the reaction of 4-chloro-2,2-dimethyl-2H-1,3-benzoxazine (1) with various α- and/or γ-substituted pyridine N-oxides are described.The benzoxazine moiety was introduced into the side chain and/or β-position of the pyridine ring, in addition to the α-position.Possible mechanism of the reactions are discussed.Keywords - 1,3-benzoxazine; picoline N-oxide; lutidine N-oxide; imidoyl chloride; rearrangement.
- Wachi, Kazuyuki,Terada, Atsusuke
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p. 3020 - 3028
(2007/10/02)
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- Synthesis and Spectroscopic Studies of some Quinolylmethylphosphonates
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Monoethyl esters of 2-quinolylmethylphosphonic acid (3) and 8-quinolylmethylphosphonic acid (6) have been prepared.The corresponding diethyl esters 1 and 4, and sodium salts of monoesters 2 and 5, respectively, have also been isolated.The properties of the monethyl esters of 8- and 2-quinolylmethylphosphonic acid are very different.While the former was isolated as the hydrochloride, the latter did not form such a salt.Molecular weight determination indicated a dimer structure of the monoester 3, and spectroscopic measurements confirmed the association presumably owing to the hydrogen bonding between the P=O and P-OH groups.
- Jagodic, V.,Bozic, B.,Tusek-Bozic, Lj.,Herak, M. J.
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p. 685 - 688
(2007/10/02)
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- 2-Alkoxy(and 2-alkoxyalkyl)-2-heterocyclic-thioacetamides for inhibiting gastric acid secretion
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The compounds are 2-alkoxy(and 2-alkoxyalkyl)-2-heterocyclic-thioacetamides which are inhibitors of gastric acid secretion.
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- 2-Alkoxy(and 2-amino)-3-amino-2-heterocyclic-thiopropanamides
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The compounds are 2-alkoxy(and 2-amino)-3-amino-2-heterocyclic-thiopropanamides, for example 2-methoxy-N-methyl-3-morpholino-2-(2-pyridyl)thiopropanamide, which are inhibitors of gastric acid secretion.
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