Back to results
US 6,191,171 B1Granted
Para-aminomethylaryl carboxamide derivatives
AssigneeMerck & Co., Inc.
InventorsStephen E. DeLaszlo, William K. Hagmann
Life of this patent
Estimating the term…
Abstract
para-Aminomethylaryl carboxamides of Formula I are antagonists of VLA-4 and/or α4β7, and as such are useful in the inhibition or prevention of cell adhesion and cell-adhesion mediated pathologies. These compounds may be formulated into pharmaceutical compositions and are suitable for use in the treatment of asthma, allergies, inflammation, multiple sclerosis, and other inflammatory and autoimmune disorders.
Claims14
A compound of formula Ia:
- wherein
- X is
- 1) a bond, or
- 2) C(R7)(R8);
- L is
- 1) —S(O)2;
- R1 is
- 1) Cy, or
- 2) Cy-C1-10alkyl,
- wherein alkyl is optionally substituted with one to four substituents independently selected from Ra;
- and Cy is optionally substituted with one to four substituents independently selected from Rb;
- or
- R1-L is
- 4-[N′-(2-methylphenyl)ureido]phenylacetyl;
- R2 is
- 1) H or
- 2) C1-5alkyl;
- R4 is
- 1) H or
- 2) C1-5alkyl;
- R5 is
- 1) C1-10alkyl,
- 2) Cy-(Cy1)p,
- 3) Cy-(Cy1)p-C1-10alkyl,
- wherein alkyl is optionally substituted with one to four substituents independently selected from Ra;
- and Cy and Cy1 are optionally substituted with one to four substituents independently selected from Rb;
- R7 is
- 1) hydrogen, or
- 2) C1-3alkyl;
- R8 is
- 1) hydrogen;
- Ra is
- 1) —CF3;
- 2) —ORd,
- 3) —NO2,
- 4) halogen
- 5) —S(O)mRd,
- 6) —CRd(N—ORe),
- 7) —S(O)2ORd,
- 8) —S(O)mNRdRe,
- 9) —NRdRe,
- 10) —O(CRfRg)nNRdRe,
- 11) —C(O)Rd,
- 12) —CO2Rd,
- 13) —CO2(CRfRg)nCONRdRe,
- 14) —OC(O)Rd,
- 15) —CN,
- 16) —C(O)NRdRe,
- 17) —NRdC(O)Re,
- 18) —OC(O)NRdRe,
- 19) —NRdC(O)ORe, or
- 20) —NRdC(O)NRdRe;
- Rb is
- 1) a group selected from Ra,
- 2) C1-10 alkyl,
- 3) C2-10 alkenyl,
- 4) C2-10 alkynyl,
- 5) Cy, or
- 6) Cy-C1-10 alkyl,
- wherein alkyl, alkenyl, alkynyl, and Cy are optionally substituted with a group independently selected from Rc;
- substituted with a group independently selected from Rc;
- Rc is
- 1) halogen,
- 2) amino,
- 3) carboxy,
- 4) C1-4alkyl,
- 5) C1-4alkoxy,
- 6) aryl,
- 7) aryl C1-4alkyl, or
- 8) aryloxy;
- Rd and Re are independently selected from the group consisting of
- 1) hydrogen,
- 2) C1-10alkyl,
- 3) C2-10alkenyl,
- 4) C2-10alkynyl,
- 5) Cy, and
- 6) Cy C1-10alkyl,
- wherein alkyl, alkenyl, alkynyl and Cy is optionally substituted with one to four substituents independently selected from Rc;
- Rf and Rg are independently selected from hydrogen, C1-10alkyl, Cy and Cy C1-10alkyl;
- Rba is
- 1) halogen,
- 2) C1-3alkyl, or
- 3) C1-3alkoxy;
- Cy and Cy1 are independently cycloalkyl or aryl;
- m 0, 1 or 2;
- n integer from 1 to 10;
- p is 0 or 1;
- or
- a pharmaceutically acceptable salt thereof.
86 more elements
A compound selected from the group consisting of:
- wherein R2 = Rb = R4 = H Ex R1—L R5 X 18 benzoyl 4-biphenylmethyl — 19 phenylacetyl 4-biphenylmethyl — 20 3,5-(diCl)-benzoyl 4-biphenylmethyl — 21 n-Bu—SO2 4-biphenylmethyl —.
Dependencies are inferred from the claim text.