Structure of oxmetidine dihydrochloride (SKF 92994)

Prout, Keith; Burns, K.; Watkin, David J.; Durant, G. J.; Brown, Tom

doi:10.1107/s0108270192003548

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“…The four possibilities, the dication, the two tautomeric forms and the disordered mixture of tautomeric forms are best distinguished by their endocyclic ring angles at the N atoms. This is observed in oxmetidine dihydrochloride (Prout, Burns, Watkin, Durant & Brown, 1993). Further, N atoms in peptide-like linkages form --CO--NH--C--angles of about 124 °, very significantly > 120 °.…”

Section: Table 4 Interatomic Distances (~) and Angles (O) Associatedmentioning

confidence: 78%

Structures of histamine H₁-receptor antagonists derived from the cimetidine group of histamine H₂-receptor antagonists

Bannister

Burns²,

Prout³

et al. 1994

Acta Crystallogr Sect B

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The crystal and molecular structures of ten compounds with strong structural resemblances to the cimetidine group of histamine H2-receptor antagonists, but exhibiting selective H1-receptor antagonist activity, (1)-(7), or H1 and H2 activity (8)-(10), have been determined: (1) 2-[4-(5-Bromo-3-methyl-2-pyridyl)butylamino]-5- (6-methyl-3-pyridylmethyl)-4-pyrimidone trihydrobromide (temalastine), C21H27BrN5O3+.3Br-, M(r) = 685.09, triclinic, P1, a = 6.314 (2), b = 11.192 (2), c = 19.441 (5) A, alpha = 102.47 (2), beta = 92.77 (2), gamma = 103.28 (2) degrees, V = 1298.51 A3, Z = 2, Dx = 1.75 g cm-3, mu = 61.6 cm-1, F(000) = 672, R = 2.93% for 3208 independent reflexions. (2) 2-[4-(5-Bromo-3-methyl-2-pyridyl)butylamino]-4-pyrimidone, C14H19BrN4O2, M(r) = 355.23, monoclinic, I2/a, a = 16.359 (3), b = 10.469 (6), c = 18.339 (4) A, beta = 90.90 (2) degrees, V = 3140.49 A3, Z = 8, Dx = 1.503 g cm-3, mu = 26.0 cm-1, F(000) = 1176, R = 4.2% for 1872 independent reflexions. (3) 3-[4-(5-Bromo-3-methyl-2-pyridyl)butylamino]-4- amino-1,2,5-thiadiazole-1-oxide, C12H16BrN5OS, M(r) = 358.26, triclinic, P1, a = 14.295 (2), b = 12.447 (2), c = 9.917 (2) A, alpha = 95.77 (2), beta = 113.86 (2), gamma = 106.91 (1) degrees, V = 1495.18 A3, Z = 4, Dx = 1.59 g cm-3, mu = 50.96 cm-1, F(000) = 728, R = 5.98% for 5674 independent reflexions. (4) 3-[4-(5-Bromo-3-methyl-2-pyridyl)butylamino]-4- benzylamino-1,2,5-thiadiazole-1-oxide, C19H22BrN5OS, M(r) = 448.38, monoclinic, P2(1)/c, a = 36.293 (7), b = 4.826 (2), c = 11.528 (3) A, beta = 96.91 (2) degrees, V = 2004.27 A3, Z = 4, Dx = 1.49 g cm-3, mu = 39.2 cm-1, F(000) = 920, R = 12.1% for 1945 independent reflexions. (5) 2-[3-(N-Benzyl-N-2- pyridylamino)propylamino]-4-pyrimidone, C19H21N5O, M(r) = 335.4, orthorhombic, Pbna, a = 7.082 (1), b = 19.889 (3), c = 24.899 (3) A, V = 3507.16 A3, Z = 8, Dx = 1.27 g cm-3, mu = 6.24 cm-1, F(000) = 1424, R = 4.05% from 2470 independent reflexions. (6) 3-[3-(N-4-Fluorobenzyl-N-2- pyridylamino)propylamino]-4-ethylamino-1,2,5-thiadiazole-1-oxide, C19H23FN6OS, M(r) = 402.5, monoclinic, P2(1)/n, a = 6.686 (2), b = 14.717 (3), c = 20.850 (5) A, beta = 97.83 (2) degrees, V = 2032.47 A3, Z = 4, Dx = 1.32 g cm-3, mu = 16.41 cm-1, F(000) = 848, R = 8.5% from 2484 independent reflexions. (7) 5-(6-Methyl-3-pyridylmethyl)-2-[3-(5,6,7,8-tetrahydro-8- quinolyl)propylamino]-4-pyrimidone, C23H29N5O2, M(r) = 407.5, monoclinic, P2(1)/c, a = 14.966 (2), b = 16.075 (2), c = 9.1608 (9) A, beta = 99.158 (8) degrees, V = 2175.83 A3, Z = 4, Dx = 1.24 g cm-3, mu = 6.19 cm-1; F(000) = 872, R = 5.3% from 2784 independent reflexions. (8) 2-(4-Phenylbutylamino)-5-(3-pyridyl-methyl)-4-pyrimidone, C20H26N4O3, M(r) = 370.5, monoclinic, P2(1)/c, a = 8.040 (4), b = 21.279 (4), c = 11.404 (2) A, beta = 92.08 (5) degrees, V = 1949.68 A3, Z = 4, Dx = 1.26 g cm-3, mu = 0.93 cm-1, F(000) = 792, R = 4.05% from 3816 independent reflexions.(ABSTRACT TRUNCATED AT 400 WORDS)

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Section: Table 4 Interatomic Distances (~) and Angles (O) Associatedmentioning

confidence: 78%

Structures of histamine H₁-receptor antagonists derived from the cimetidine group of histamine H₂-receptor antagonists

Bannister

Burns²,

Prout³

et al. 1994

Acta Crystallogr Sect B

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ChemInform Abstract: Structure of Oxmetidine Dihydrochloride (SKF 92994).

et al. 1993

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structure structure (organic substances) K 9000 -047Structure of Oxmetidine Dihydrochloride (SKF 92994).-Oxmetidine (I) is a highly effective histamine H2 antagonist inhibiting gastric acidity in man. Its structure as dihydrochloride is determined (P1, Z = 2) in order to discuss the kind of hydrogen bonds. -(PROUT, K.; BURNS, K.; WATKIN, D. J.; DURANT, G. J.; BROWN, T. H.; Acta Crystallogr., Sect. C: Cryst.

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Structure of oxmetidine dihydrochloride (SKF 92994)

Cited by 2 publications

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Structures of histamine H₁-receptor antagonists derived from the cimetidine group of histamine H₂-receptor antagonists

Structures of histamine H₁-receptor antagonists derived from the cimetidine group of histamine H₂-receptor antagonists

ChemInform Abstract: Structure of Oxmetidine Dihydrochloride (SKF 92994).

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Structure of oxmetidine dihydrochloride (SKF 92994)

Cited by 2 publications

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Structures of histamine H1-receptor antagonists derived from the cimetidine group of histamine H2-receptor antagonists

Structures of histamine H1-receptor antagonists derived from the cimetidine group of histamine H2-receptor antagonists

ChemInform Abstract: Structure of Oxmetidine Dihydrochloride (SKF 92994).

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Structures of histamine H₁-receptor antagonists derived from the cimetidine group of histamine H₂-receptor antagonists

Structures of histamine H₁-receptor antagonists derived from the cimetidine group of histamine H₂-receptor antagonists