| US 7,572,922 B2 | ||
| Substituted pyrazoles, compositions containing such compounds and methods of use | ||
| Emma Parmee, Scotch Plains, N.J. (US); Subharekha Raghavan, Teaneck, N.J. (US); Teresa Beeson, Pasadena, Calif. (US); and Dong-Ming Shen, Edison, N.J. (US) | ||
| Assigned to Merck & Co., Inc., Rahway, N.J. (US) | ||
| Appl. No. 10/543,290 PCT Filed Jan. 23, 2004, PCT No. PCT/US2004/001927 § 371(c)(1), (2), (4) Date Jul. 25, 2005, PCT Pub. No. WO2004/069158, PCT Pub. Date Aug. 19, 2004. |
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| Claims priority of provisional application 60/442828, filed on Jan. 27, 2003. | ||
| Prior Publication US 2006/0084681 A1, Apr. 20, 2006 | ||
| Int. Cl. C07D 257/00 (2006.01); C07D 231/10 (2006.01); A01N 43/64 (2006.01); A01N 43/56 (2006.01) | ||
| U.S. Cl. 548—377.1 [548/251; 514/381; 514/406] | 16 Claims |
1. A compound represented by formula I:
 R′ is selected from the group consisting of:
(a) C1-10alkyl optionally substituted with: (1) 1-5 halo groups up to a perhaloalkyl group; (2) 1 oxo group; (3) 1-2 OH groups; (4)
1-2 C1-10alkoxy groups, each optionally substituted with: up to five halo or a perhaloalkoxy, 1 OH or C2R8 group; (5) 1 C2R8 or S(O)pR7; (6) 1-2 Arl, Tetcy or HAR groups, each optionally substituted as follows: (i) 1-5 halo groups, (ii) 1 OH, CO2R8, CN, S(O)pR7, NO2 or C(O)NR9R10 group, (iii) 1-2 C1-10alkyl or alkoxy groups, each optionally substituted with: 1-5 halo, up to perhaloalkyl, and 1-2 OH or CO2R8 groups; and (iv) 1-2 phenyl rings, each of which is optionally substituted as follows: 1-3 C1-10alkyl or alkoxy groups, each being further optionally substituted with 1-5 halo up to perhalo, or 1-2 hydroxy or CO2R8 groups; (7) —NR8—C(O)—NR9R10; (8) —NR8—CO2R11; (9) —NR8—C(O)R11; (10) —NR9R10 ; (11) —NR8SO2R11 ; NR9R10; (13) —C(O)NR9R10 and (14) —OC(O)—NR9R10;
(b) Aryl optionally substituted as follows: (1) 1-3 C1-10alkyl, C2-10alkenyl or C2-10alkynyl groups optionally substituted with 1-5 halo groups, 1-2 OH, phenyl, CO2R8, CN or S(O)pR7 groups; (2) 1-3 C1-10alkoxy groups, the alkyl portion of which is optionally substituted with 1-5 halo groups, 1-2 OH, phenyl, CO2R8, CN or S(O)pR7 groups; (3) 1-2 Aryl, HAR or Hetcy groups, each optionally substituted as follows: (i) 1-3 halo groups; (ii) 1-2 C1-10alkyl, C2-10alkenyl or C2-10aykynyl groups each optionally substituted with 1-5 halo groups, 1-2 OH, phenyl, CO2R11, CN or S(O)pR7 groups; (iii) 1-2 C1-10alkoxy groups the alkyl portion of which being optionally substituted with 1-5 halo groups, 1-2 OH, phenyl, CO2R11, CN or S(O)pR7 groups; and (iv) 1-2 CO2R11, S(O)pR7, CN, NR9R10, NO2 or OH groups;
said Aryl being further optionally substituted on carbon by a group selected from the group consisting of; (4) 1-5 halo groups;
(5) 1-2 OH groups; (6) 1 S(O)pR7, NO2 or CN group; (7) 1-2 CO2R8; (8) —NR8—C(O)NR9R10; (9) —NR8—CO2R11; (10) —NR8—C(O)R11; (11) —NR9R10; (12) —NR8SO2R11; (13) —SO2—NR910; (14) —C(O)NR9R10 and (15) —OC(O)—NR9R10;
R2 is H or RI as defined above;
R3 and R4 are H or C1-10alkyl;
R5 represents H or F;
R6 represents H, OH, F or C1-3alkyl, or R5 and R6 are taken in combination and represent oxo;
R7 represents a member selected from the group consisting of: C1-10alkyl, Aryl or Ar-C1-10alkyl,
R8 is H, C1-10alkyl, optionally substituted with phenyl, OH, OC1-6alkyl, CO2H, CO2C1-6alkyl and 1-3 halo groups;
R9 is H or C1-10alkyl;
R10 is H or is independently selected from: (a) C1-10alkyl, optionally substituted with OH, OC1-6alkyl, CO2H, CO2C1-6alkyl, and 1-3 halo groups; (b) Aryl or Ar-C1-6alkyl, each optionally substituted with 1-5 halos and 1-3 members selected from the group consisting of: CN, OH, C1-10alkyl and OC1-10 alkyl, said alkyl and alkoxy being further optionally substituted with 1-5 halo groups up to perhalo; (c) Hetcy or Hetcy-C1-6alkyl, optionally substituted with 1-5 halo groups and 1-3 groups selected from: oxo, C1-10alkyl and OC1-10alkyl, said alkyl and alkoxy being further optionally substituted with 1-5 halo groups up to perhalo; and (d) HAR or HAR-C1-6alkyl, optionally substituted with 1-5 halo groups and 1-3 groups selected from: C1-10alkyl and OC1-10 alkyl, said alkyl and alkoxy being further optionally substituted with 1-5 halo groups up to perhalo;
R11 is independently selected from the group consisting of: (a) C1-10alkyl, optionally substituted with OH, OC1-6alkyl, CO2H, CO2C1-6alkyl, and 1-3 halo groups; (b) Aryl or Ar-1-6alkyl, each optionally substituted with 1-5 halos and 1-3 members selected from the group consisting of: CN, OH, C1-10alkyl and OC1-10 alkyl, said alkyl and alkoxy being further optionally substituted with 1-5 halo groups up to perhalo; (c) Hetcy or Hetcy-C1-6alkyl, optionally substituted with 1-5 halo groups and 1-3 groups selected from: oxo, C1-10alkyl and OC1-10 alkyl, said alkyl and alkoxy being further optionally substituted with 1-5 halo groups up to perhalo; and (d) HAR or HAR-C1-6alkyl, optionally substituted with 1-5 halo groups and 1-3 groups selected from: C1-10alkyl and OC1-10alkyl, said alkyl and alkoxy being further optionally substituted with 1-5 halo groups up to perhalo;
m is an integer sclectcd from 0, 1 and 2;
n is an integer selected from 0 to 6;
p is an integer selected from 0, 1 and 2, and
when at least one of m and n is other than 0, Z is selected from C2R8, 5-tetrazolyl and 5-(2-oxo-1,3,4-oxadiazolyl), and when both m and n are 0, Z is selected from 5-tetrazolyl and 5-(2-oxo-1,3,4-oxadiazolyl).
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