Preparation of tetrahydroisoquinoline and tetrahydrobenzoazepine derivatives for use as GPR120 modulators.

Jane Brown; Stephen Connolly; Steffen V. F. Hansen; Gavin Milne; Bharat Shimpukade; Don Smyth; Gerard Thomas; Trond Ulven; Matjaz Brvar; Aaron. Rigby

Preparation of tetrahydroisoquinoline and tetrahydrobenzoazepine derivatives for use as GPR120 modulators.

Jane Brown (Inventor), Stephen Connolly (Inventor), Steffen V. F. Hansen (Inventor), Gavin Milne (Inventor), Bharat Shimpukade (Inventor), Don Smyth (Inventor), Gerard Thomas (Inventor), Trond Ulven (Inventor), Matjaz Brvar (Inventor), Aaron. Rigby (Inventor)

Abstract

Title compds. I [A = CO2H, CH2OH, tetrazolyl, etc.; E and L independently = (un)substituted alkyl, alkoxy, cycloalkyl, etc.; G = (un)substituted aryl, heteroaryl, or fused aryl or heteroaryl ring; J = C(R1)2, O, NR1, or S; M = aryl, heteroaryl, or cycloalkyl; X = absent, O, S, or C(R1)2; Y = absent, O, or C(R1)2; Z = absent or C(R1)2; X and Y, Y and Z, or X and Z may be combined to form an (un)substituted cycloalkyl ring; each R1 independently = H, D, halo, or (un)substituted alkyl; n = 1 or 2; with provisions], and their pharmaceutically acceptable salts, are prepd. and disclosed as GPR120 modulators. Thus, e.g., II was prepd. by a multistep procedure (prepn. given). I were evaluated in human GPR120-B arrestin 2 bio-luminescence resonance energy transfer (BRET) agonist assays, e.g., II demonstrated a pEC50 value of 7.4. [on SciFinder(R)]

Original language	English
Patent number	WO2018172727A1
Country/Territory	Denmark
Publication status	Published - 27 Sept 2018

Keywords

tetrahydrobenzoazepine prepn GPR120 modulator
tetrahydroisoquinoline prepn GPR120 modulator

Cite this

@misc{edf537ffabd14d1293a588621ab4c78e,

title = "Preparation of tetrahydroisoquinoline and tetrahydrobenzoazepine derivatives for use as GPR120 modulators.",

abstract = "Title compds. I [A = CO2H, CH2OH, tetrazolyl, etc.; E and L independently = (un)substituted alkyl, alkoxy, cycloalkyl, etc.; G = (un)substituted aryl, heteroaryl, or fused aryl or heteroaryl ring; J = C(R1)2, O, NR1, or S; M = aryl, heteroaryl, or cycloalkyl; X = absent, O, S, or C(R1)2; Y = absent, O, or C(R1)2; Z = absent or C(R1)2; X and Y, Y and Z, or X and Z may be combined to form an (un)substituted cycloalkyl ring; each R1 independently = H, D, halo, or (un)substituted alkyl; n = 1 or 2; with provisions], and their pharmaceutically acceptable salts, are prepd. and disclosed as GPR120 modulators. Thus, e.g., II was prepd. by a multistep procedure (prepn. given). I were evaluated in human GPR120-B arrestin 2 bio-luminescence resonance energy transfer (BRET) agonist assays, e.g., II demonstrated a pEC50 value of 7.4. [on SciFinder(R)]",

keywords = "tetrahydrobenzoazepine prepn GPR120 modulator, tetrahydroisoquinoline prepn GPR120 modulator",

author = "Jane Brown and Stephen Connolly and Hansen, {Steffen V. F.} and Gavin Milne and Bharat Shimpukade and Don Smyth and Gerard Thomas and Trond Ulven and Matjaz Brvar and Aaron. Rigby",

year = "2018",

month = sep,

day = "27",

language = "English",

publisher = "Caldan Therapeutics Limited, UK .",

type = "Patent",

note = "WO2018172727A1",

}

TY - PAT

T1 - Preparation of tetrahydroisoquinoline and tetrahydrobenzoazepine derivatives for use as GPR120 modulators.

AU - Brown, Jane

AU - Connolly, Stephen

AU - Hansen, Steffen V. F.

AU - Milne, Gavin

AU - Shimpukade, Bharat

AU - Smyth, Don

AU - Thomas, Gerard

AU - Ulven, Trond

AU - Brvar, Matjaz

AU - Rigby, Aaron.

PY - 2018/9/27

Y1 - 2018/9/27

N2 - Title compds. I [A = CO2H, CH2OH, tetrazolyl, etc.; E and L independently = (un)substituted alkyl, alkoxy, cycloalkyl, etc.; G = (un)substituted aryl, heteroaryl, or fused aryl or heteroaryl ring; J = C(R1)2, O, NR1, or S; M = aryl, heteroaryl, or cycloalkyl; X = absent, O, S, or C(R1)2; Y = absent, O, or C(R1)2; Z = absent or C(R1)2; X and Y, Y and Z, or X and Z may be combined to form an (un)substituted cycloalkyl ring; each R1 independently = H, D, halo, or (un)substituted alkyl; n = 1 or 2; with provisions], and their pharmaceutically acceptable salts, are prepd. and disclosed as GPR120 modulators. Thus, e.g., II was prepd. by a multistep procedure (prepn. given). I were evaluated in human GPR120-B arrestin 2 bio-luminescence resonance energy transfer (BRET) agonist assays, e.g., II demonstrated a pEC50 value of 7.4. [on SciFinder(R)]

AB - Title compds. I [A = CO2H, CH2OH, tetrazolyl, etc.; E and L independently = (un)substituted alkyl, alkoxy, cycloalkyl, etc.; G = (un)substituted aryl, heteroaryl, or fused aryl or heteroaryl ring; J = C(R1)2, O, NR1, or S; M = aryl, heteroaryl, or cycloalkyl; X = absent, O, S, or C(R1)2; Y = absent, O, or C(R1)2; Z = absent or C(R1)2; X and Y, Y and Z, or X and Z may be combined to form an (un)substituted cycloalkyl ring; each R1 independently = H, D, halo, or (un)substituted alkyl; n = 1 or 2; with provisions], and their pharmaceutically acceptable salts, are prepd. and disclosed as GPR120 modulators. Thus, e.g., II was prepd. by a multistep procedure (prepn. given). I were evaluated in human GPR120-B arrestin 2 bio-luminescence resonance energy transfer (BRET) agonist assays, e.g., II demonstrated a pEC50 value of 7.4. [on SciFinder(R)]

KW - tetrahydrobenzoazepine prepn GPR120 modulator

KW - tetrahydroisoquinoline prepn GPR120 modulator

M3 - Patent

M1 - WO2018172727A1

PB - Caldan Therapeutics Limited, UK .

ER -

Preparation of tetrahydroisoquinoline and tetrahydrobenzoazepine derivatives for use as GPR120 modulators.

Abstract

Keywords

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