149771-43-7Relevant articles and documents
An improved and scalable process for 3,8-diazabicyclo[3.2.1]octane analogues
Huang, Long Jiang,Teng, Da Wei
, p. 523 - 526 (2011)
An improved and scalable process for substituted 3,8-diazabicyclo[3.2.1] octane was developed. N-Benzyl-2,5-dicarbethoxy-pyrrolidine 2 was reduced to N-benzyl-2,5-dihydroxymethylpyrrolidine 9 and subsequently debenzylated to afford N-Boc-2,5-dihydroxymeth
Phenyl-diazabicyclo derivative and application thereof
-
Paragraph 0228; 0230; 0231, (2018/11/22)
The invention discloses a phenyl-diazabicyclo derivative and application thereof, as well as pharmaceutical compositions containing such compounds, which are used for inhibiting serotonin reuptaking.The invention also relates to methods of preparing such
Pyruvate kinase activators for use in therapy
-
Page/Page column 178-179, (2016/08/29)
Described herein are methods for using compounds that activate pyruvate kinase.
NOVEL SUBSTITUTED DIAZABICYCLO DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
-
Page/Page column 16, (2008/06/13)
This invention relates to novel substituted diazabicyclo derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions
3,8-Diazabicyclo[3.2.1]octanes and their use in the treatment of cardiac arrhythmias
-
, (2008/06/13)
There is provided compounds of formula (I), wherein R1, R2 and Ra to Rb have meanings given in the description, which are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and v
N-benzenesulfonyl L-proline compounds as bradykinin antagonists
-
Page 12, (2010/01/31)
This invention provides a compound of the formula (I): or the pharmaceutically acceptable salts thereof wherein X1 and X2 are halo; R1 andR2 are independently hydrogen or C1-4 alkyl; R3 and R4 are each hydrogen or halo; andR5 is(a) -C3-9 diazacycloalkyl optionally substituted with C5-11 azabicycloalkyl;(b) -C3-9 azacycloalkyl-NH-(C5-11 azabicycloalkyl optionally substituted with C1-4 alkyl);(c) -NH-C1-3 alkyl-C(O)-C5-11 diazabicycloalkyl;(d) -NH-C1-3 alkyl-C(O)-NH-C5-11 azabicycloalkyl, the C5-11 azabicycloalkyl being optionally substituted with C1-4 alkyl;(e) -C3-9 azacycloalkyl optionally substituted with C3-9 azacycloalkyl; or(f) -NH-C1-5 alkyl-NH-C(O)-C4-9 cycloalkyl-NH2. These compounds are useful for the treatment of medical conditions mediated by bradykinin such as inflammation, allergic rhinitis, pain, etc. This invention also provides a pharmaceutical composition comprising the above compound.
Tandem cyclisation and [2,3]-Stevens rearrangement to 2-substituted pyrrolidines
Smith, Stephen C,Bentley, Philip D
, p. 899 - 902 (2007/10/03)
Reaction of N-methylallylamine with diethyl meso-2,5-dibromoadipate in DMF at ambient temperature in the presence of potassium carbonate led directly to the two diastereomers of diethyl 2-allyl-N-methylpyrrolidine-2,5-dicarboxylate. The reaction proceeds via a [2,3]-sigmatropic Stevens rearrangement, which occurred spontaneously under the reaction conditions. This gave a higher yield under milder conditions than the traditional Stevens reaction of diethyl N-allylpyrrolidine-2,5-dicarboxylate with iodomethane. The sequence was a key step in the synthesis of a series of analogues of the alkaloid stemofoline.
N-benzenesulfonyl l-proline compounds as bradykinin antagonists
-
, (2008/06/13)
This invention provides a compound of the formula (I): or the pharmaceutically acceptable salts thereof wherein X1 and X2 are halo; R1 and R2 are independently hydrogen or C1-4 alkyl; R3 and R4 are each hydrogen or halo; and R5 is (a) —C3-9 diazacycloalkyl optionally substituted with C5-11 azabicycloalkyl; (b) —C3-9 azacycloalkyl-NH—(C5-11 azabicycloalkyl optionally substituted with C1-4 alkyl); (c) —NH—C1-3 alkyl-C(O)—C5-11 diazabicycloalkyl; (d) —NH—C1-3 alkyl-C(O)—NH—C5-11 azabicycloalkyl, the C5-11 azabicycloalkyl being optionally substituted with C1-4 alkyl; (e) —C3-9 azacycloalkyl optionally substituted with C3-9 azacycloalkyl; or (f) —NH—C1-5 alkyl-NH—C(O)—C4-9 cycloalkyl-NH2. These compounds are useful for the treatment of medical conditions mediated by bradykinin such as inflammation, allergic rhinitis, pain, etc. This invention also provides a pharmaceutical composition comprising the above compound.
Mono- and disubstituted-3,8-diazabicyclo[3.2.1]octane derivatives as analgesics structurally related to epibatidine: Synthesis, activity, and modeling
Barlocco, Daniela,Cignarella, Giorgio,Tondi, Donatella,Vianello, Paola,Villa, Stefania,Bartolini, Alessandro,Ghelardini, Carla,Galeotti, Nicoletta,Anderson, David J.,Kuntzweiler, Theresa A.,Colombo, Diego,Toma, Lucio
, p. 674 - 681 (2007/10/03)
A series of 3,8-diazabicyclo[3.2.1]octanes substituted either at the 3 position compounds 1) or at the 8 position (compounds 2) by a chlorinated heteroaryl ring were synthesized, as potential analogues of the potent natural analgesic epibatidine. When tested in the hot plate assay, the majority of the compounds showed significant effects, the most interesting being the 3-(6-chloro-3-pyridazinyl)-3,8-diazabicyclo[3.2.1]octane (la). At a subcutaneous dose of 1 mg/kg, 1a induced a significant increase in the pain threshold, its action lasting for about 45 min. 1a also demonstrated good protection at a dose of 5 mg/kg in the mouse abdominal constriction test, while at 20 mg/kg it completely prevented the constrictions in the animals. Administration of naloxone (1 mg/kg ip) did not antagonize its antinociception while mecamylamine (2 mg/kg ip) did, thus suggesting the involvement of the nicotinic system in its action. Binding studies confirmed high affinity for the αβ2 nAChR subtype (K(i) = 4.1±0.21 nM). nAChR functional activity studies on three different cell lines showed that 1a was devoid of any activity at the neuromuscular junction. Finally, due to the analogy in their pharmacological profile with that of epibatidine, compounds were compared from a structural and conformational point of view through theoretical calculations and high-field 1H NMR spectroscopy. Results indicate that all of them present one conformation similar to that of epibatidine.
Synthesis and μ-opioid receptor affinity of a new series of nitro substituted 3,8-diazabicyclo[3.2.1]octane derivatives
Barlocco,Cignarella,Vianello,Villa,Pinna,Fadda,Fratta
, p. 557 - 562 (2007/10/03)
A new series of analogues (1c-j; 2c-i) of the previously reported analgesic 3,8-diazabicyclo[3.2.1]octanes (1a,b; 2a,b) was synthesized and tested for their affinity towards μ-opioid receptors. Modifications were introduced either at the cinnamyl or the acyl side chains. The majority of the new compounds, with the exception of 1c,j and 2c, showed K(i) values better or comparable with those of the models.
