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US20140045746A1 - Antidiabetic tricyclic compounds - Google Patents

Antidiabetic tricyclic compoundsDownload PDF

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Publication number
US20140045746A1
US20140045746A1US13/955,282US201313955282AUS2014045746A1US 20140045746 A1US20140045746 A1US 20140045746A1US 201313955282 AUS201313955282 AUS 201313955282AUS 2014045746 A1US2014045746 A1US 2014045746A1
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alkyl
group
unsubstituted
substituted
halogen
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US13/955,282
Inventor
William K. Hagmann
Ravi P. Nargund
Timothy A. Blizzard
Hubert Josien
Purakkattle Biju
Christopher W. Plummer
Qun Dang
Bing Li
Linus S. Lin
Mingxiang Cui
Bin Hu
Jinglai Hao
Zhengxia Chen
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Wuxi Apptec BVI Inc
Merck Sharp and Dohme LLC
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Merck Sharp and Dohme LLC
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Priority claimed from PCT/CN2012/079558external-prioritypatent/WO2014019186A1/en
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Priority to US13/955,282priorityCriticalpatent/US20140045746A1/en
Assigned to MERCK SHARP & DOHME CORPreassignmentMERCK SHARP & DOHME CORPASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: WUXI APPTEC (BVI) INC.
Assigned to WUXI APPTEC (BVI) INC.reassignmentWUXI APPTEC (BVI) INC.ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: WUXI APPTEC (SHANGHAI) CO., LTD.
Assigned to WUXI APPTEC (SHANGHAI) CO., LTD.reassignmentWUXI APPTEC (SHANGHAI) CO., LTD.ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: LIN, LINUS S., CHEN, Zhengxia, CUI, MINGXIANG, HAO, JINGLAI, HU, BIN
Assigned to MERCK SHARP & DOHME CORPreassignmentMERCK SHARP & DOHME CORPASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: JOSIEN, HUBERT, BIJU, PURAKKATTLE, BLIZZARD, TIMOTHY A., HAGMANN, WILLIAM K., LI, BING, NARGUND, RAVI P., PLUMMER, CHRISTOPHER W.
Assigned to MERCK SHARP & DOHME CORPreassignmentMERCK SHARP & DOHME CORPASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: DANG, QUN
Publication of US20140045746A1publicationCriticalpatent/US20140045746A1/en
Assigned to WUXI APPTEC CO., LTDreassignmentWUXI APPTEC CO., LTDASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: CHEN, Zhengxia, HU, BIN, LIN, LINUS S., CUI, MINGXIANG, HAO, JINGLAI
Assigned to MERCK SHARP & DOHME CORP.reassignmentMERCK SHARP & DOHME CORP.ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: WUXI APPTEC CO., LTD
Assigned to MERCK SHARP & DOHME CORP.reassignmentMERCK SHARP & DOHME CORP.ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: WUXI APPTEC (BVI) INC.
Assigned to WUXI APPTEC (BVI) INC.reassignmentWUXI APPTEC (BVI) INC.ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: WUXI APPTEC CO., LTD
Assigned to MERCK SHARP & DOHME CORP.reassignmentMERCK SHARP & DOHME CORP.ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: DANG, QUN, BIJU, PURAKKATTLE, JOSIEN, HUBERT, LI, BING, LI, DERUN, NARGUND, RAVI P., PLUMMER, CHRISTOPHER W., BLIZZARD, TIMOTHY A., HAGMANN, WILLIAM K.
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Abstract

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.
Figure US20140045746A1-20140213-C00001

Description

Claims (31)

Figure US20140045746A1-20140213-C00310
or a pharmaceutically acceptable salt thereof; wherein
X is selected from the group consisting of:
(1) oxygen, and
(2) NH;
T is selected from the group consisting of: CH, N and N-oxide;
U is selected from the group consisting of: CH, N and N-oxide;
V is selected from the group consisting of: CH, N and N-oxide;
provided that one or two of T, U and V is N or N-oxide;
A is selected from the group consisting of:
(1) aryl, and
(2) heteroaryl,
wherein A is unsubstituted or substituted with one to five substituents selected from Ra;
B is selected from the group consisting of:
(1) aryl,
(2) aryl-O—,
(3) C3-6cycloalkyl-,
(4) C3-6cycloalkyl-C1-10-alkyl-,
(5) C3-6cycloalkyl-C1-10alkyl-O—,
(6) C2-5cycloheteroalkyl-,
(7) heteroaryl,
(8) heteroaryl-O—,
(9) aryl-C1-10alkyl-, and
(10) heteroaryl-C1-10alkyl-,
wherein B is unsubstituted or substituted with one to five substituents selected from Rb;
R1is selected from the group consisting of:
(1) halogen,
(2) —ORe,
(3) —CN,
(4) —C1-6alkyl, and
(5) —C3-6cycloalkyl,
wherein each —C1-6alkyl and —C3-6cycloalkyl is unsubstituted or substituted with one to three substituents selected from Ri;
R2is selected from the group consisting of:
(1) hydrogen,
(2) —C1-6alkyl, and
(3) —C3-6cycloalkyl,
wherein each —C1-6alkyl and —C3-6cycloalkyl is unsubstituted or substituted with one to three substituents selected from Rj;
R3is selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) —ORe,
(4) —C1-6alkyl,
(5) —C2-6alkenyl,
(6) —C2-6alkynyl, and
(7) —C3-6cycloalkyl,
wherein each C1-6alkyl, C2-6alkenyl, C2-6alkynyl, and C3-6cycloalkyl is unsubstituted or substituted with one to three substituents selected from RL;
R4is selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) —ORe,
(4) —C1-6alkyl,
(5) —C2-6alkenyl,
(6) —C2-6alkynyl, and
(7) —C3-6cycloalkyl,
wherein each —C1-6alkyl, —C2-6alkenyl, —C2-6alkynyl, and —C3-6cycloalkyl is unsubstituted or substituted with one to three substituents selected from RL;
R5is selected from the group consisting of:
(1) hydrogen,
(2) —C1-3alkyl, and
(3) halogen;
R6is selected from the group consisting of:
(1) hydrogen,
(2) —C1-3alkyl, and
(3) halogen, or
R5and R6can together form oxo;
Rais selected from the group consisting of:
(1) —C1-6alkyl,
(2) halogen,
(3) —ORe,
(4) —NRcS(O)mRe,
(5) —S(O)mRe,
(6) —S(O)mNRcRd,
(7) —NRcRd,
(8) —C(O)Re,
(9) —OC(O)Re,
(10) —CO2Re,
(11) —CN,
(12) —C(O)NRcRd,
(13) —NRcC(O)Re,
(14) —NRcC(O)ORe,
(15) —NRcC(O)NRcRd,
(16) —CF3,
(17) —OCF3,
(18) —OCHF2,
(19) —C3-6cycloalkyl, and
(20) —C2-5cycloheteroalkyl;
Rbis independently selected from the group consisting of:
(1) —C1-10alkyl,
(2) —C2-10alkenyl,
(3) halogen,
(4) —OH,
(5) —OC1-10alkyl,
(6) —OC2-10alkenyl,
(7) —O(CH2)pOC1-10alkyl,
(8) —O(CH2)pC3-6cycloalkyl,
(9) —O(CH2)pC3-6cycloalkyl-C1-10alkyl-,
(10) —O(CH2)pC2-10cycloheteroalkyl,
(11) —O(CH2)pC2-5cycloheteroalkyl-C1-10alkyl-,
(12) —O-aryl,
(13) —O-heteroaryl,
(14) —O-aryl-C1-10alkyl-,
(15) —O-heteroaryl-C1-10alkyl-,
(16) —NRcS(O)mRe,
(17) —S(O)mRe,
(18) —S(O)mNRcRd,
(19) —NRcRd,
(20) —C(O)Re,
(21) —OC(O)Re,
(22) —CO2Re,
(23) —CN,
(24) —C(O)NRcRd,
(25) —NRcC(O)Re,
(26) —NRcC(O)ORe,
(27) —NRcC(O)NRcRd,
(28) —O(CH2)pO—C3-6cycloalkyl,
(29) —O(CH2)pO—C2-10cycloheteroalkyl,
(30) —CF3,
(31) —OCF3,
(32) —OCHF2,
(33) —(CH2)p—C3-6cycloalkyl,
(34) —(CH2)p—C2-10cycloheteroalkyl,
(35) aryl,
(36) heteroaryl,
(37) aryl-C1-10alkyl-, and
(38) heteroaryl-C1-10alkyl-,
wherein each Rbis unsubstituted or substituted with one to five substituents selected from Rk;
Rcand Rdare each independently selected from the group consisting of:
(1) hydrogen,
(2) C1-10alkyl,
(3) C2-10alkenyl,
(4) C3-6cycloalkyl,
(5) C3-6cycloalkyl-C1-10alkyl-,
(6) cycloheteroalkyl,
(7) cycloheteroalkyl-C1-10alkyl-,
(8) aryl,
(9) heteroaryl,
(10) aryl-C1-10alkyl-, and
(11) heteroaryl-C1-10alkyl-, or
Rcand Rdtogether with the atom(s) to which they are attached form a cycloheteroalkyl ring of 4 to 7 members containing 0-2 additional heteroatoms independently selected from oxygen, sulfur and N—Rg, and wherein each Rcand Rdis unsubstituted or substituted with one to three substituents independently selected from Rf;
each Reis independently selected from the group consisting of:
(1) hydrogen,
(2) —C1-10alkyl,
(3) —C2-10alkenyl,
(4) —C3-6cycloalkyl,
(5) —C3-6cycloalkyl-C1-10alkyl-,
(6) —C2-5cycloheteroalkyl,
(7) —C2-5cycloheteroalkyl-C1-10alkyl-,
(8) aryl,
(9) heteroaryl,
(10) aryl-C1-10alkyl-, and
(11) heteroaryl-C1-10-alkyl-,
wherein each Reis unsubstituted or substituted with one to three substituents selected from Rh;
each Rfis selected from the group consisting of:
(1) halogen,
(2) C1-10alkyl,
(3) —OH,
(4) —O—C1-4alkyl,
(5) —S(O)m—C1-4alkyl,
(6) —CN,
(7) —CF3,
(8) —OCHF2, and
(9) —OCF3,
wherein each C1-10alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, halogen, cyano, and —S(O)2CH3;
each Rgis selected from the group consisting of:
(1) hydrogen,
(2) —C(O)Re, and
(3) —C1-10alkyl,
wherein —C1-10alkyl is unsubstituted or substituted with one to five fluorines;
each Rhis selected from the group consisting of:
(1) halogen,
(2) C1-10alkyl,
(3) —OH,
(4) —O—C1-4alkyl,
(5) —S(O)m—C1-4alkyl,
(6) —CN,
(7) —CF3,
(8) —OCHF2, and
(9) —OCF3,
wherein each C1-10alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, halogen, cyano, and —S(O)2CH3;
Riis independently selected from the group consisting of:
(1) —C1-6alkyl,
(2) —ORe,
(3) —NRcS(O)mRe,
(4) halogen,
(5) —S(O)mRe,
(6) —S(O)mNRcRd,
(7) —NRcRd,
(8) —C(O)Re,
(9) —OC(O)Re,
(10) —CO2Re,
(11) —CN,
(12) —C(O)NRcRd,
(13) —NRcC(O)Re,
(14) —NRcC(O)ORe,
(15) —NRcC(O)NRcRd,
(16) —CF3,
(17) —OCF3,
(18) —OCHF2,
(19) —C3-6cycloalkyl, and
(20) —C2-5cycloheteroalkyl;
Rjis independently selected from the group consisting of:
(1) —C1-6alkyl,
(2) —ORe,
(3) —NRcS(O)mRe,
(4) halogen,
(5) —S(O)mRe,
(6) —S(O)mNRcRd,
(7) —NRcRd,
(8) —C(O)Re,
(9) —OC(O)Re,
(10) —CO2Re,
(11) —CN,
(12) —C(O)NRcRd,
(13) —NRcC(O)Re,
(14) —NRcC(O)ORe,
(15) —NRcC(O)NRcRd,
(16) —CF3,
(17) —OCF3,
(18) —OCHF2,
(19) —C3-6cycloalkyl, and
(20) —C2-5cycloheteroalkyl;
each Rkis independently selected from the group consisting of:
(1) halogen,
(2) —C1-10alkyl,
(3) —OH,
(4) oxo,
(5) halogen,
(6) —O—C1-4alkyl,
(7) —SO2—C1-6alkyl,
(8) —C1-6alkyl-SO2C1-6alkyl,
(9) —CN,
(10) —CF3,
(11) —OCHF2,
(12) —OCF3,
(13) —NH2,
(14) —NHSO2C1-6alkyl,
(15) —NHCOC1-6alkyl,
(16) ═N(OCH3),
(17) —P(O)(OH)2, and
(18) —P(O)(OC1-6alkyl)2,
wherein each C1-10alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, —OC1-6alkyl, halogen, cyano, and —S(O)2C1-6alkyl;
RLis selected from the group consisting of:
(1) —C1-6alkyl,
(2) halogen,
(3) —ORe,
(4) —NRcS(O)mRe,
(5) —S(O)mRe,
(6) —S(O)mNRcRd,
(7) —NRcRd,
(8) —C(O)Re,
(9) —OC(O)Re,
(10) —CO2Re,
(11) —CN,
(12) —C(O)NRcRd,
(13) —NRcC(O)Re,
(14) —NRcC(O)ORe,
(15) —NRcC(O)NRcRd,
(16) —CF3,
(17) —OCF3,
(18) —OCHF2,
(19) —C3-6cycloalkyl, and
(20) —C2-5cycloheteroalkyl;
each n is independently selected from: 0, 1, 2, 3 or 4;
each m is independently selected from: 0, 1 or 2; and
each p is independently selected from: 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
21. The compound according toclaim 1 wherein:
n is 1;
X is oxygen;
T is CH;
U is N;
V is CH;
A is selected from the group consisting of: phenyl and pyridine, wherein A is unsubstituted or substituted with one to five substituents selected from Ra;
B is selected from the group consisting of: phenyl, pyridine, pyrimidine, thiazole, benzimidazole, benzthiazole, benzoxazole, and benzisoxazole, wherein B is unsubstituted or substituted with one to five substituents selected from Rb;
R1, R2, R3, R4, R5and R6are hydrogen;
Rais selected from the group consisting of: —C1-6alkyl, halogen, and —CF3;
Rbis independently selected from the group consisting of:
(1) —C1-10alkyl,
(2) halogen,
(3) —OH,
(4) —OC1-10alkyl,
(5) —O(CH2)pOC1-10alkyl,
(6) —O(CH2)pC3-6cycloalkyl,
(7) —O(CH2)pC2-10cycloheteroalkyl,
(8) —O(CH2)pO—C3-6cycloalkyl,
(9) —O(CH2)pO—C2-10cycloheteroalkyl,
(10) —CF3,
(11)
(12) —OCF3,
(13) —OCHF2,
(14) —(CH2)p—C2-10cycloheteroalkyl, and
(15) —S(O)2C1-10alkyl,
wherein each Rbis unsubstituted or substituted with one to five substituents selected from Rk; and each Rkis independently selected from the group consisting of:
(1) —C1-10alkyl,
(2) —O—C1-4alkyl,
(3) —OH,
(4) halogen,
(5) —SO2—C1-6alkyl,
(6) —C1-6alkyl-SO2C1-6alkyl,
(7) —CN,
(8) —NHSO2C1-6alkyl,
(9) ═N(OCH3), and
(10) —P(O)(OC1-6alkyl)2,
wherein each C1-10alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, —OC1-6alkyl, halogen, cyano, and —S(O)2C1-6alkyl;
or a pharmaceutically acceptable salt thereof.
22. The compound according toclaim 1 wherein
n is 1;
X is oxygen;
T is CH;
U is N;
V is CH;
A is phenyl, wherein phenyl is unsubstituted or substituted with one to five substituents selected from Ra;
B is selected from the group consisting of: phenyl and pyridine, wherein B is unsubstituted or substituted with one to five substituents selected from Rb;
R1, R2, R3, R4, R5and R6are hydrogen;
Rais selected from the group consisting of: —C1-6alkyl, halogen, and —CF3;
Rbis independently selected from the group consisting of:
(1) —C1-10alkyl,
(2) halogen,
(3) —OH,
(4) —OC1-10alkyl,
(5) —O(CH2)pC2-10cycloheteroalkyl,
(6) —CF3, and
(7) —(CH2)p—C2-10cycloheteroalkyl,
wherein each Rbis unsubstituted or substituted with one to five substituents selected from Rk; and
each Rkis independently selected from the group consisting of:
(1) —C1-10alkyl,
(2) —OH,
(3) halogen,
(4) —SO2—C1-6alkyl,
(5) —C1-6alkyl-SO2C1-6alkyl, and
(6) —CN,
wherein each C1-10alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, —OC1-6alkyl, halogen, cyano, and —S(O)2C1-6alkyl;
or a pharmaceutically acceptable salt thereof.
30. A pharmaceutical composition comprising
(1) a compound ofclaim 1 or a pharmaceutically acceptable salt thereof;
(2) one or more compounds selected from the group consisting of:
(a) PPAR gamma agonists and partial agonists;
(b) biguanides;
(c) protein tyrosine phosphatase-1B (PTP-1B) inhibitors;
(d) dipeptidyl peptidase IV (DP-IV) inhibitors;
(e) insulin or an insulin mimetic;
(f) sulfonylureas;
(g) α-glucosidase inhibitors;
(h) agents which improve a patient's lipid profile, said agents being selected from the group consisting of (i) HMG-CoA reductase inhibitors, (ii) bile acid sequestrants, (iii) nicotinyl alcohol, nicotinic acid or a salt thereof, (iv) PPARα agonists, (v) cholesterol absorption inhibitors, (vi) acyl CoA:cholesterol acyltransferase (ACAT) inhibitors, (vii) CETP inhibitors, and (viii) phenolic anti-oxidants;
(i) PPARα/γ dual agonists,
(j) PPARδ agonists,
(k) antiobesity compounds,
(l) ileal bile acid transporter inhibitors;
(m) anti-inflammatory agents;
(n) glucagon receptor antagonists;
(o) GLP-1;
(p) GIP-1;
(q) GLP-1 analogs;
(r) HSD-1 inhibitors;
(s) SGLT 1 inhibitors; and
(t) SGLT 2 inhibitors; and
(3) a pharmaceutically acceptable carrier.
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