137975-06-5 Usage
Uses
Used in Pharmaceutical Industry:
Mozavaptan is used as a vasopressin V2 receptor antagonist for the treatment of congestive heart failure and hyponatremia. It helps in correcting sodium and water imbalance by blocking the renal V2 receptor, leading to enhanced diuresis and effectively increasing serum sodium concentration.
Used in Treatment of IADHS:
Mozavaptan is used as a vasopressin-receptor antagonist for the treatment of inappropriate antidiuretic hormone secretion syndrome (IADHS), a condition that manifests as hyponatremia. Its selective action on V2 receptors makes it a preferred choice for this specific condition.
Originator
Otsuka (Japan)
Synthesis
The reported synthesis of mozavaptan is shown in
the scheme. Readily available benzazepin-5-one 39
was refluxed with 40% methyl amine methanol solution
in the presence of molecular sieves for 5h followed by the
reduction of the resulting imine with sodium borohydride to
give the monomethyl amine. Reductive alkylation of the
monomethyl amine with formaldehyde in the presence of
sodium cyanoborohydride gave the dimethyl amino benzazepine
40. Removal of the tosyl group was facilitated by
heating 40 in polyphosphoric acid at 150oC for 2 h to give 41 in 97% yield. Reaction of the resulting benzazepine 41 with
p-nitrobenzoyl chloride (42) in the presence of triethylamine
provided amide 43 which was hydrogenated in the presence
of 10% Pd/C in ethanol at room temperature to give aniline
44. Acylation of aniline 44 with 2-methylbenzoylchloride
(45) in the presence of triethylamine gave mozavaptan (VI)
in 54% yield.
Check Digit Verification of cas no
The CAS Registry Mumber 137975-06-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,7,9,7 and 5 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 137975-06:
(8*1)+(7*3)+(6*7)+(5*9)+(4*7)+(3*5)+(2*0)+(1*6)=165
165 % 10 = 5
So 137975-06-5 is a valid CAS Registry Number.
InChI:InChI=1/C27H29N3O2/c1-19-9-4-5-10-22(19)26(31)28-21-16-14-20(15-17-21)27(32)30-18-8-13-24(29(2)3)23-11-6-7-12-25(23)30/h4-7,9-12,14-17,24H,8,13,18H2,1-3H3,(H,28,31)
137975-06-5Relevant academic research and scientific papers
An efficient synthesis of a metabolite of vasopressin V2 receptor antagonist, OPC-31260, by metalloporphyrin-catalyzed demethylation
Kawano, Yoshikazu,Otsubo, Kenji,Matsubara, Jun,Kitano, Kazuyoshi,Ohtani, Tadaaki,Morita, Seiji,Uchida, Minoru
, p. 17 - 20 (2007/10/03)
A secondary amine (3) as a metabolite of the vasopressin V2 receptor antagonist, OPC-31260 (1), was efficiently prepared through selective demethylation of the corresponding N,N-dimethylalkylamine N-oxide (2) with meso-(tetraphenylporphinato)iron(III) chl
Orally active, nonpeptide vasopressin V2 receptor antagonists: A novel series of 1-[4-(benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and related compounds
Ogawa, Hidenori,Yamashita, Hiroshi,Kondo, Kazumi,Yamamura, Yoshitaka,Miyamoto, Hisashi,Kan, Keizo,Kitano, Kazuyoshi,Tanaka, Michinori,Nakaya, Kenji,Nakamura, Shigeki,Mori, Toyoki,Tominaga, Michiaki,Yabuuchi, Youichi
, p. 3547 - 3555 (2007/10/03)
This paper describes a novel series of nonpeptide vasopressin V2 receptor antagonists. It has been demonstrated that the 1-[4- (benzoylamino)benzoyl]-2,3,4,5-1H-benzazepines and 1-[4- (benzoylamino)benzoyl]-2,3,4,5-1H-1,5-benzodiazepines show a high affinity for V2 (and V(1a)) receptors. Among the 1-[4-(benzoylamino)benzoyl]-2,3,4,5- 1H-benzazepine series, compounds with an alkylamino group on the benzazepine ring have been shown to have oral activity. A lipophilic group at the ortho position on the terminal benzoyl ring is important for both high V2 receptor affinity and oral activity. On the basis of these favorable properties, clinical testing of 31b has begun for use as an oral and iv aquaretic agent.
