IP Library › Granted Patent US 9,150,578
Granted Patent B2
US 9,150,578 · App. 13/746,411 · Granted Oct 6, 2015

5,8-dihydro-6

Inventor: Matthias Treu (Vienna, AT)
Assignee: Boehringer Ingelheim International GmbH
C07D487/04C07D487/14
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,150,578
App. No.
13/746,411
Granted
Oct 6, 2015
Kind
B2
Abstract

The present invention encompasses compounds of general formula (I) wherein the groups R 1 to R 6 , A, B, C, n, p, q and r are defined as in claim 1 , which are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation, pharmaceutical preparations which contain compounds of this kind and their use as medicaments.

Claims (190)

1. A compound of the formula (I)

wherein

R 1 denotes C 1-4 alkyl;

R 2 denotes hydrogen or C 1-4 alkyl;

R 3 denotes hydrogen or C 1-4 alkyl;

n denotes 0 or 1;

ring A is phenyl or 5-6 membered heteroaryl;

each R 4 is independently of one another selected from among halogen, C 1-4 alkoxy, C 1-4 alkyl and —CN;

p denotes 0, 1 or 2;

ring B is a 5-membered heteroaryl;

each R 5 independently is R b1 or a group, optionally substituted by one or more, identical or different R b1 and/or R c1 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b1 is independently selected from among —OR c1 , —NR c1 R c1 , halogen, —CN, —C(O)R c1 , —C(O)OR c1 , —C(O)NR c1 R c1 , —S(O) 2 R c1 , S(O) 2 NR c1 R c1 , —NHC(O)R c1 and —N(C 1-4 alkyl)C(O)R c1 ;

each R c1 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d1 and/or R e1 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d1 is independently selected from among —OR e1 , —NR e1 R e1 halogen, —CN, —C(O)R e1 , —C(O)OR e1 , —C(O)NR e1 R e1 , —S(O) 2 R e1 , —S(O) 2 NR e1 R e1 , — NHC(O)R e1 and —N(C 1-4 alkyl)C(O)R e1 ;

each R e1 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f1 and/or R g1 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f1 is independently selected from among —OR g1 , —NR g1 R g1 , halogen, —CN, —C(O)R g1 , —C(O)OR g1 , —C(O)NR g1 R g1 , —S(O) 2 R g1 , —S(O) 2 NR g1 R g1 , — NHC(O)R g1 and —N(C 1-4 alkyl)C(O)R g1 ;

each R g1 independently of one another denotes hydrogen or C 1-6 alkyl;

q denotes 0, 1 or 2;

ring C is phenyl or 5-6 membered heteroaryl;

each R 6 independently is R b2 or a group, optionally substituted by one or more, identical or different R b2 and/or R c2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b2 is independently selected from among —OR c2 , —NR c2 R c2 , halogen, —CN, —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 , —S(O) 2 R c2 , —S(O) 2 NR c2 R c2 , — NHC(O)R c2 and —N(C 1-4 alkyl)C(O)R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 , —NR e2 R e2 , halogen, —CN, —C(O)R e2 , —C(O)OR e2 , —C(O)NR e2 R e2 , —S(O) 2 R e2 , —S(O) 2 NR e2 R e2 , — NHC(O)R e2 and —N(C 1-4 alkyl)C(O)R e2 ;

each R e2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f2 and/or R g2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f2 is independently selected from among —OR g2 , —NR g2 R g2 , halogen, —CN, —C(O)R g2 , —C(O)OR g2 , —C(O)NR g2 R g2 , —S(O) 2 R g2 , —S(O) 2 NR g2 R g2 , — NHC(O)R g2 and —N(C 1-4 alkyl)C(O)R g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2;

or a tautomer or salt thereof.

2. A compound according to claim 1 , wherein

ring C is phenyl;

each R 6 independently is R b2 or a group, optionally substituted by one or more, identical or different R b2 and/or R c2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b2 is independently selected from among —OR c2 , —NR c2 R c2 , halogen, —CN, —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 , —S(O) 2 R c2 , —S(O) 2 NR c2 R c2 , — NHC(O)R c2 and —N(C 1-4 alkyl)C(O)R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 , —NR e2 R e2 , halogen, —CN, —C(O)R e2 , —C(O)OR e2 , —C(O)NR e2 R e2 , —S(O) 2 R e2 , —S(O) 2 NR e2 R e2 , — NHC(O)R e2 and —N(C 1-4 alkyl)C(O)R e2 ;

each R e2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f2 and/or R g2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f2 is independently selected from among —OR g2 , —NR g2 R g2 , halogen, —CN, —C(O)R g2 , —C(O)OR g2 , —C(O)NR g2 R g2 , —S(O) 2 R g2 , —S(O) 2 NR g2 R g2 , — NHC(O)R g2 and —N(C 1-4 alkyl)C(O)R g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2.

3. A compound according to claim 1 , wherein

ring C is phenyl;

each R 6 independently is R b2 or a group, optionally substituted by one or more, identical or different R b2 and/or R c2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b2 is independently selected from among —OR c2 , —NR c2 R c2 , halogen, —CN, —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 , —S(O) 2 R c2 , —S(O) 2 NR c2 R c2 , —NHC(O)R c2 and —N(C 1-4 alkyl)C(O)R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 , —NR e2 R e2 , halogen, —CN, —C(O)R e2 , —C(O)OR e2 , —C(O)NR e2 R e2 , —S(O) 2 R e2 , —S(O) 2 NR e2 R e2 , — NHC(O)R e2 and —N(C 1-4 alkyl)C(O)R e2 ;

each R e2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f2 and/or R g2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f2 is independently selected from among —OR g2 , —NR g2 R g2 , halogen, —CN, —C(O)R g2 , —C(O)OR g2 , —C(O)NR g2 R g2 , —S(O) 2 R g2 , —S(O) 2 NR g2 R g2 , — NHC(O)R g2 and —N(C 1-4 alkyl)C(O)R g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2.

4. A compound according to claim 1 , wherein

ring C is phenyl;

each R 6 independently is R b2 or 3-7 membered heterocyclyl, the heterocyclyl optionally substituted by one or more, identical or different R b2 and/or R c2 ;

each R b2 is independently selected from among —OR c2 , —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 and —S(O) 2 NR c2 R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 and —NR e2 R e2 ;

each R e2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f2 and/or R g2 , selected from among C 1-6 alkyl and 3-7 membered heterocyclyl;

each R f2 is —OR g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2.

5. A compound according to claim 1 , wherein

ring C is phenyl;

each R 6 independently is —C(O)NR c2 R c2 , —C(O)R c2 or —OR c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 and —NR e2 R e2 ;

each R e2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f2 and/or R g2 , selected from among C 1-6 alkyl and 3-7 membered heterocyclyl;

each R f2 is —OR g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2.

6. A compound according to claim 1 , wherein

r is 2.

7. A compound according to claim 1 , wherein

ring C is 5-6 membered heteroaryl;

each R 6 independently is R b2 or a group, optionally substituted by one or more, identical or different R b2 and/or R c2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b2 is independently selected from among —OR c2 , —NR c2 R c2 , halogen, —CN, —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 , —S(O) 2 R c2 , —S(O) 2 NR c2 R c2 , —NHC(O)R c2 and —N(C 1-4 alkyl)C(O)R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 , —NR e2 R e2 , halogen, —CN, —C(O)R e2 , —C(O)OR e2 , —C(O)NR e2 R e2 , —S(O) 2 R e2 , —S(O) 2 NR e2 R e2 , — NHC(O)R e2 and —N(C 1-4 alkyl)C(O)R e2 ;

each R e2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f2 and/or R g2 , selected from among C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 4-6 cycloalkenyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f2 is independently selected from among —OR g2 , —NR g2 R g2 , halogen, —CN, —C(O)R g2 , —C(O)OR g2 , —C(O)NR g2 R g2 , —S(O) 2 R g2 , —S(O) 2 NR g2 R g2 , — NHC(O)R g2 and —N(C 1-4 alkyl)C(O)R g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2.

8. A compound according to claim 7 , wherein

ring C is 5-6 membered heteroaryl;

each R 6 independently is R b2 or a group, optionally substituted by one or more, identical or different R b2 and/or R c2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b2 is independently selected from among —OR c2 , —NR c2 R c2 , halogen, —CN, —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 , —S(O) 2 R c2 , —S(O) 2 NR c2 R c2 , —NHC(O)R c2 and —N(C 1-4 alkyl)C(O)R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 , —NR e2 R e2 , halogen, —CN, —C(O)R e2 , —C(O)OR e2 , —C(O)NR e2 R e2 , —S(O) 2 R e2 , —S(O) 2 NR e2 R e2 , — NHC(O)R e2 and —N(C 1-4 alkyl)C(O)R e2 ;

each R e2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f2 and/or R g2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f2 is independently selected from among —OR g2 , —NR g2 R g2 , halogen, —CN, —C(O)R g2 , —C(O)OR g2 , —C(O)NR g2 R g2 , —S(O) 2 R g2 , —S(O) 2 NR g2 R g2 , — NHC(O)R g2 and —N(C 1-4 alkyl)C(O)R g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2.

9. A compound according to claim 8 , wherein

ring C is pyrazolyl;

each R 6 independently is R b2 or a group, optionally substituted by one or more, identical or different R b2 and/or R c2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b2 is independently selected from among —OR c2 , —NR c2 R c2 , halogen, —CN, —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 , —S(O) 2 R c2 , —S(O) 2 NR c2 R c2 , —NHC(O)R c2 and —N(C 1-4 alkyl)C(O)R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 , —NR e2 R e2 , halogen, —CN, —C(O)R e2 , —C(O)OR e2 , —C(O)NR e2 R e2 , —S(O) 2 R e2 , —S(O) 2 NR e2 R e2 , —NHC(O)R e2 and —N(C 1-4 alkyl)C(O)R e2 ;

each R e2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f2 and/or R g2 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f2 is independently selected from among —OR g2 , —NR g2 R g2 , halogen, —CN, —C(O)R g2 , —C(O)OR g2 , —C(O)NR g2 R g2 , —S(O) 2 R g2 , —S(O) 2 NR g2 R g2 , —NHC(O)R g2 and —N(C 1-4 alkyl)C(O)R g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2.

10. A compound according to claim 9 , wherein

ring C is pyrazolyl;

each R 6 independently is a group, optionally substituted by one or more, identical or different R b2 and/or R c2 , selected from among C 1-6 alkyl and 3-7 membered heterocyclyl;

each R b2 is independently selected from among —OR c2 , —NR c2 R c2 , —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 , S(O) 2 R c2 and —S(O) 2 NR c2 R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 and —NR e2 R e2 ;

each R e2 independently of one another denotes hydrogen or C 1-6 alkyl optionally substituted by one or more, identical or different R f2 and/or R g2 ;

each R f2 is —OR g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl;

r denotes 0, 1 or 2.

11. A compound according to claim 10 , wherein

r is 1.

12. A compound according to claim 10 , wherein

r is 1 and ring C and R 6 altogether is

R 6 independently is a group, optionally substituted by one or more, identical or different R b2 and/or R c2 , selected from among C 1-6 alkyl and 3-7 membered heterocyclyl;

each R b2 is independently selected from among —OR c2 , —NR c2 R c2 , —C(O)R c2 , —C(O)OR c2 , —C(O)NR c2 R c2 , —S(O) 2 R c2 and —S(O) 2 NR c2 R c2 ;

each R c2 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d2 and/or R e2 , selected from among C 1-6 alkyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d2 is independently selected from among —OR e2 and —NR e2 R e2 ;

each R e2 independently of one another denotes hydrogen or C 1-6 alkyl optionally substituted by one or more, identical or different R f2 and/or R g2 ;

each R f2 is —OR g2 ;

each R g2 independently of one another denotes hydrogen or C 1-6 alkyl.

13. A compound according to claim 12 , wherein

r is 1 and ring C and R 6 altogether is

R 6 independently is selected from among C 1-4 alkyl, hydroxy-C 2-4 alkyl, C 1-4 alkoxy-C 2-4 alkyl and (C 1-4 alkyl) 2 N—C 2-4 alkyl.

14. A compound according to claim 12 , wherein

r is 1 and ring C and R 6 altogether is selected from among

15. A compound according to claim 1 , wherein

ring B is a 5-membered heteroaryl;

each R 5 independently is R b1 or a group, optionally substituted by one or more, identical or different R b1 and/or R c1 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b1 is independently selected from among —OR c1 , —NR c1 R c1 , halogen, —CN, —C(O)R c1 , —C(O)OR c1 , —C(O)NR c1 R c1 , —S(O) 2 R c1 , —S(O) 2 NR c1 R c1 , —NHC(O)R c1 and —N(C 1-4 alkyl)C(O)R c1 ;

each R c1 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d1 and/or R e1 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d1 is independently selected from among —OR e1 , —NR e1 R e1 , halogen, —CN, —C(O)R e1 , —C(O)OR e1 , —C(O)NR e1 R e1 , —S(O) 2 R e1 , —S(O) 2 NR e1 R e1 , —NHC(O)R e1 and —N(C 1-4 alkyl)C(O)R e1 ;

each R e1 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f1 and/or R g1 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f1 is independently selected from among —OR g1 , —NR g1 R g1 , halogen, —CN, —C(O)R g1 , —C(O)OR g1 , —C(O)NR g1 R g1 , —S(O) 2 R g1 , —S(O) 2 NR g1 R g1 , —NHC(O)R g1 and —N(C 1-4 alkyl)C(O)R g1 ;

each R g1 independently of one another denotes hydrogen or C 1-6 alkyl;

q denotes 0, 1 or 2.

16. A compound according to claim 15 , wherein

ring B is pyrazolyl;

each R 5 independently is R b1 or a group, optionally substituted by one or more, identical or different R b1 and/or R c1 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R b1 is independently selected from among —OR c1 , —NR c1 R c1 , halogen, —CN, —C(O)R c1 , —C(O)OR c1 , —C(O)NR c1 R c1 , —S(O) 2 R c1 , —S(O) 2 NR c1 R c1 , —NHC(O)R c1 and —N(C 1-4 alkyl)C(O)R c1 ;

each R c1 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d1 and/or R e1 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R d1 is independently selected from among —OR e1 , —NR e1 R e1 , halogen, —CN, —C(O)R e1 , —C(O)OR e1 , —C(O)NR e1 R e1 , —S(O) 2 R e1 , —S(O) 2 NR e1 R e1 , —NHC(O)R e1 and —N(C 1-4 alkyl)C(O)R e1 ;

each R e1 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R f1 and/or R g1 , selected from among C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl and 3-7 membered heterocyclyl;

each R f1 is independently selected from among —OR g1 , —NR g1 R g1 , halogen, —CN, —C(O)R g1 , —C(O)OR g1 , —C(O)NR g1 R g1 , —S(O) 2 R g1 , —S(O) 2 NR g1 R g1 , —NHC(O)R g1 and —N(C 1-4 alkyl)C(O)R g1 ;

each R g1 independently of one another denotes hydrogen or C 1-6 alkyl;

q denotes 0, 1 or 2.

17. A compound according to claim 16 , wherein

ring B is pyrazolyl;

each R 5 independently is a group, optionally substituted by one or more, identical or different R b1 and/or R c1 , selected from among C 1-6 alkyl and 3-7 membered heterocyclyl;

each R b1 is independently selected from among —OR c1 , —NR c1 R c1 , halogen, —C(O)OR c1 and —C(O)NR c1 R c1 ;

each R c1 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d1 and/or R e1 , selected from among C 1-6 alkyl, phenyl and 3-7 membered heterocyclyl;

each R d1 is independently selected from among —OR e1 and —NR e1 R e1 ;

each R e1 independently of one another denotes hydrogen or C 1-6 alkyl optionally substituted by one or more, identical or different R f1 and/or R g1 ;

each R f1 is —OR g1 ;

each R g1 independently of one another denotes hydrogen or C 1-6 alkyl;

q denotes 0, 1 or 2.

18. A compound according to claim 17 , wherein

q is 1.

19. A compound according to claim 17 , wherein

q is 1 and ring B and R 5 altogether is

R 5 is a group, optionally substituted by one or more, identical or different R b1 and/or R c1 , selected from among C 1-6 alkyl and 3-7 membered heterocyclyl;

each R b1 is independently selected from among —OR c1 , —NR c1 R c1 , halogen, —C(O)OR c1 and —C(O)NR c1 R c1 ;

each R c1 independently of one another denotes hydrogen or a group, optionally substituted by one or more, identical or different R d1 and/or R e1 , selected from among C 1-6 alkyl, phenyl and 3-7 membered heterocyclyl;

each R d1 is independently selected from among —OR e1 and —NR e1 R e1 ;

each R e1 independently of one another denotes hydrogen or C 1-6 alkyl optionally substituted by one or more, identical or different R f1 and/or R g1 ;

each R f1 is —OR g1 ;

each R g1 independently of one another denotes hydrogen or C 1-6 alkyl.

20. A compound according to claim 19 , wherein

q is 1 and ring B and R 5 altogether is

R 5 independently is selected from among C 1-4 alkyl, hydroxy-C 2-4 alkyl, C 1-4 alkoxy-C 2-4 alkyl and (C 1-4 alkyl) 2 N—C 2-4 alkyl.

21. A compound according to claim 19 , wherein

q is 1 and ring B and R 5 altogether is selected from among

22. A compound according to claim 1 , wherein

R 1 is methyl.

23. A compound according to claim 1 , wherein

R 2 and R 3 both denote hydrogen.

24. A compound according to claim 1 , wherein

R 2 is hydrogen and R 3 is C 1-4 alkyl.

25. A compound according to claim 1 , wherein

R 2 is hydrogen and R 3 is methyl.

26. A compound according to claim 1 , wherein

ring A is phenyl or pyridyl;

each R 4 is independently of one another selected from among halogen, C 1-4 alkoxy, C 1-4 alkyl and —CN;

p denotes 0, 1 or 2.

27. A compound according claim 26 , wherein

ring A is phenyl or pyridyl;

p is 0.

28. A compound according to claim 1 selected from the group consisting of

or a tautomer or salt thereof.

29. A pharmaceutically acceptable salt of a compound according to one of claim 1 to 28 .

30. A pharmaceutical preparation containing as active substance a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient or carrier.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 19, 2015
From: TREU, MATTHIAS
To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Reel/Frame 036363/0381 →
Priority Claims (1)
EP 12152193 · Jan 23, 2012 · regional
Continuity (1)
Related Publication 20130190305A1 · Jul 25, 2013