Compositions useful as inhibitors of protein kinases
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Accused Products
Abstract
The present invention relates to compounds useful as inhibitors of protein kinases. The invention also provides processes for preparing the compounds, pharmaceutically acceptable compositions comprising the compounds, and methods of using the compounds and compositions in the treatment of various disease, conditions, or disorders.
24 Citations
63 Claims
-
1. A compound of formula I:
- View Dependent Claims (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 57, 58)
-
3. The compound of claim 1 or claim 2, wherein R1 and R2, taken together with the carbon atoms to which they are bound form an optionally substituted 5-membered heteroaryl ring selected from one of the following groups:
-
4. The compound of claim 1 or claim 2, wherein R1 and R2, taken together with the carbon atoms to which they are bound form an optionally substituted 5-membered heteroaryl ring selected from thiophenyl (iv-1, iv-2, and xviii).
-
5. The compound of claim 1 or claim 2, wherein each occurrence of WRy, when present, is independently halogen, CN, NO2, —
- N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, or —
S(O)2N(R′
)2, or an optionally substituted group selected from C1-4alkyl, aryl, heteroaryl.
- N(R′
-
6. The compound of claim 1 or claim 2, wherein —
- WRy groups are each independently F, Cl, Br, I, Me, Et, —
CN, —
OMe, —
SMe, —
NMe2, —
NEt2, —
COOMe, —
COOH, —
OH, —
SO2NH2, —
CON(CH3)2, —
CO(optionally substituted N-piperazinyl), —
CO(N-morpholinyl), —
CO(N-piperidinyl), —
CH2N(Me)2, —
CH2N(Et)2, or an optionally substituted group selected from C1-4alkoxy, phenyl, phenyloxy, benzyl, benzyloxy, pyridyl, pyrimidinyl, thiophene, N-morpholinyl, N-piperidinyl, N-piperazinyl, or furanyl.
- WRy groups are each independently F, Cl, Br, I, Me, Et, —
-
7. The compound of claim 1 or claim 2, wherein —
- WRy groups are each independently CF3, F, Cl, Br, I, Me, Et, —
CN, —
OMe, —
SMe, —
NMe2, —
NEt2, —
COOMe, —
COOH, —
OH, —
SO2NH2, —
CON(CH3)2, —
CO(optionally substituted N-piperazinyl, —
CO(N-morpholinyl), —
CO(N-piperidinyl), —
CO(pyrrolidinyl), —
CO(N(H)pyrrolidinyl), —
CH2N(Me)2, —
CH2N(Et)2 or an optionally substituted group selected from C1-4alkoxy, phenyl, phenyloxy, benzyl, benzyloxy, pyridyl, pyrimidinyl, thiophene, N-morpholinyl, N-piperidinyl, N-piperazinyl, furanyl, pyrrolidinyl, or N(H)pyrrolidinyl.
- WRy groups are each independently CF3, F, Cl, Br, I, Me, Et, —
-
8. The compound of claim 1 or claim 2, wherein m is 1 and WRy is an optionally substituted aryl or heteroaryl group, wherein substituents for the optionally substituted aryl or heteroaryl group are independently selected from —
- VRV;
wherein V is a bond or is a C1-C6 alkylidene chain wherein up to two non-adjacent methylene units of V are independently optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and
each occurrence of RV is independently selected from R′
, halogen, NO2, or CN, or -QRX is ═
O, ═
S, or ═
NR′
.
- VRV;
-
9. The compound of claim 1 or claim 2, wherein m is 1 and WRy is —
- CH2N(R′
)2, —
N(R′
)2, or —
CON(R′
)2.
- CH2N(R′
-
10. The compound of claim 1 or claim 2, wherein T groups, when present are —
- CH2—
, —
CH2CH2, —
CO—
, or —
SO2—
.
- CH2—
-
11. The compound of claim 1 or claim 2, wherein T groups, when present are —
- C(H)(CH3)—
, —
C(H)(CH3)CH2—
, —
CH2C(H)(CH3)—
, or —
CH2CH2CH2—
.
- C(H)(CH3)—
-
12. The compound of claim 1 or claim 2, wherein n is 0 and T is absent.
-
13. The compound of claim 1 or claim 2, wherein T is absent (n=0) or T is —
- CO—
.
- CO—
-
14. The compound of claim 1 or claim 2, wherein Cy1 is selected from one of the following groups:
-
15. The compound of claim 1 or claim 2, wherein Cy1 is selected from:
-
16. The compound of claim 1 or claim 2, wherein Cy1 is selected from:
-
17. The compound of claim 1 or claim 2, wherein Cy1 is phenyl (a), and compounds have the formula I-A:
-
18. The compound of claim 1 or claim 2, wherein QRX groups, when present, are each independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, aryl, aralkyl, —
- N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, —
SO2R′
, NR′
SO2R′
, or —
SO2N(R′
)2.
- N(R′
-
19. The compound of claim 1 or claim 2, wherein QRX groups, when present are each independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, —
- CF3, aryl, heteroaryl, aralkyl, —
N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, —
SO2R′
, NR′
SO2R′
, SO2N═
R′
, or —
SO2N(R′
)2.
- CF3, aryl, heteroaryl, aralkyl, —
-
20. The compound of claim 1 or claim 2, wherein QRX groups are each independently Cl, Br, F, CF3, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, NO2, —
- OH, —
SO2NH2, SO2CH3, NH2, SO2NHCH3, NHSO2CH3, or an optionally substituted group selected from C1-4alkoxy, phenyl, phenyloxy, benzyl, or benzyloxy.
- OH, —
-
41. The compound of claim 1 or claim 2, wherein X is —
- (CH2)3— and
compounds have the general formula VII;
- (CH2)3— and
-
42. The compound of claim 41, wherein Cy1 is selected from any one of a through mm depicted above (including certain subsets b-i, c-i, b-ii, b-iii, c-ii c-iii, g-i, ll, o-i or mm).
-
43. The compound of claim 41, wherein Cy1 is option ally substituted phenyl, and compounds have formula VII-A:
-
44. The compound of claim 41, wherein R1 and R2, taken together with the carbon atoms to which they are bound form an optionally substituted 5-membered heteroaryl ring selected from thiophenyl (iv-1, iv-2, and xviii), and compounds have one of the formulae X-G, X-H, or X-I:
-
45. The compound of claim 44, wherein Cy1 is phenyl, optionally and independently substituted with k occurrences of QRX, wherein k is 0-3.
-
46. The compound of claim 45, wherein n is 0, or n is 1 and T is CH2 —
- CH2CH2—
, —
CO—
or —
SO2—
; and
each occurrence of QRXis independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, aryl, aralkyl, —
N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, —
SO2R′
, NR′
SO2R′
, or —
SO2N(R′
)2.
- CH2CH2—
-
47. The compound of claim 44, wherein m is 0-3;
- and each occurrence of WRy is independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, aryl, heteroaryl, —
N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, or —
S(O)2N(R′
)2.
- and each occurrence of WRy is independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, aryl, heteroaryl, —
-
48. The compound of claim 44, wherein m is 1 and WRy is an aryl or heteroaryl group optionally substituted with one or more occurrences of —
- VRV;
wherein V is a bond or is a C1-C6 alkylidene chain wherein up to two non-adjacent methylene units of V are independently optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and
each occurrence of RV is independently selected from R′
, halogen, NO2, or CN, or -QRX is ═
O, ═
S, or ═
NR′
.
- VRV;
-
49. The compound of claim 44, wherein m is 1 and WRy is a phenyl, pyridyl, pyrimidinyl, thiophenyl, or furanyl group optionally substituted with one or more occurrences of —
- VRV;
wherein V is a bond or is a C1-C6 alkylidene chain wherein up to two non-adjacent methylene units of V are independently optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and
each occurrence of RV is independently selected from R′
, halogen, NO2, or CN, or -QRX is ═
O, ═
S, or ═
NR′
.
- VRV;
-
50. The compound of claim 44, wherein m is 1, W is —
- CH2—
, a bond, or —
CO—
, and Ry is —
N(R′
)2 and compounds have the formula X-H-ii below;
- CH2—
-
51. The compound of claim 44, wherein one occurrence of WRy is an optionally substituted aryl or heteroaryl group, denoted by Ar1 in formula X-H-i below, wherein m is 1-5:
-
52. The compound of claim 51, wherein Ar1 is a phenyl, pyridyl, pyrimidinyl, thiophenyl, or furanyl group optionally substituted with one or more occurrences of —
- VRV;
wherein V is a bond or is a C1-C6 alkylidene chain wherein up to two non-adjacent methylene units of V are independently optionally replaced by CO, C2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and
each occurrence of RV is independently selected from R′
, halogen, NO2, or CN, or -QRX is ═
O, ═
S, or ═
NR′
.
- VRV;
-
53. The compound of claim 44, wherein n is 0, or n is 1 and T is CH2, —
- CH2CH2, —
CO—
or —
SO2.
- CH2CH2, —
-
54. The compound of claim 45, wherein n is 0, or n is 1 and T is CH2, —
- CH2CH2—
, —
CO—
or —
SO2—
; and
each occurrence of QRX is independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, aryl, aralkyl, —
N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, —
SO2R′
, NR′
SO2R′
, or —
SO2N(R′
)2.
- CH2CH2—
-
57. The compound of claim 1, wherein the compound is selected from:
-
58. The compound of claim 1 or claim 2, wherein the compound is selected from:
-
3. The compound of claim 1 or claim 2, wherein R1 and R2, taken together with the carbon atoms to which they are bound form an optionally substituted 5-membered heteroaryl ring selected from one of the following groups:
-
2. A compound of formula I:
- View Dependent Claims (21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 55, 56, 63)
-
21. The compound of claim 2, wherein X is —
- CH═
CH—
, —
S—
CH2—
, —
CH2—
S—
, —
CH2—
O—
, or —
O—
CH2—
, and the compounds have one of the structures IV, V, VI, VII, VIII, or IX;
- CH═
-
22. The compound of claim 21 wherein Cy1 is optionally substituted phenyl, and compounds have one of formulae IV-A through IX-A:
-
23. The compound of claim 21, wherein R1 and R2, taken together with the carbon atoms to which they are bound form an optionally substituted 5-membered heteroaryl ring selected from thiophenyl (iv-1, iv-2, and xviii).
-
24. The compound of claim 21, wherein R1 and R2, taken together with the carbon atoms to which they are bound form an optionally substituted 5-membered aryl or heteroaryl ring selected from thiophenyl (iv-1, iv-2, and xviii), and compounds have one of the formulas IV-G, IV-H, or IV-I:
-
25. The compound of claim 21, wherein R1 and R2, taken together with the carbon atoms to which they are bound form an optionally substituted 5-membered aryl or heteroaryl ring selected from thiophenyl (iv-1, iv-2, and xviii) and compounds have one of the formulas V-G, V-H, or V-I:
-
26. The compound of claim 21, wherein R1 and R2, taken together with the carbon atoms to which they are bound form an optionally substituted 5-membered heteroaryl ring selected from thiophenyl (iv-1, iv-2, and xviii)-and compounds have one of the formulas IX-G, IX-H, or IX-I:
-
27. The compound of claim 21, wherein Cy1 is phenyl, optionally substituted with 0-3 occurrences of QRX.
-
28. The compound of claim 27, wherein n is 0, or n is 1 and T is CH2, —
- CH2CH2—
, —
CO—
or —
SO2—
;
k is 0-3; and
each occurrence of QRX is independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, aryl, aralkyl, —
N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, —
SO2R′
, NR′
SO2R′
, or —
SO2N(R′
)2.
- CH2CH2—
-
29. The compound of claim 28, wherein m is 0-3 and each occurrence of WRy is independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, aryl, heteroaryl, —
- N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, or —
S(O)2N(R′
)2.
- N(R′
-
30. The compound of claim 28, wherein —
- WRy groups are each independently CF3, F, Cl, Br, I, Me, Et, —
CN, —
OMe, —
SMe, —
NMe2, —
NEt2, —
COOMe, —
COOH, —
OH, —
SO2NH2, —
CON(CH3)2, —
CO(optionally substituted N-piperazinyl), —
CO(N-morpholinyl), —
CO(N-piperidinyl), —
CO(pyrrolidinyl), —
CO(N(H)pyrrolidinyl), —
CH2N(Me)2, —
CH2N(Et)2, or an optionally substituted group selected from C1-4alkoxy, phenyl, phenyloxy, benzyl, benzyloxy, pyridyl, pyrimidinyl, thiophene, N-morpholinyl, N-piperidinyl, N-piperazinyl, furanyl, pyrrolidinyl, or N(H)pyrrolidinyl.
- WRy groups are each independently CF3, F, Cl, Br, I, Me, Et, —
-
31. The compound of claim 29, wherein one occurrence of WRy is an optionally substituted aryl or heteroaryl group, denoted by Ar1 in one of formulae IV-H-i, V-H-i, or IX-H-i below:
-
32. The compound of claim 31, wherein m is 1 and Ar1 is a phenyl, pyridyl, pyrimidinyl, thiophenyl, or furanyl group optionally substituted with one or more occurrences of —
- VRV;
wherein V is a bond or is a C1-C6 alkylidene chain wherein up to two non-adjacent methylene units of V are independently optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and
each occurrence of RV is independently selected from R′
, halogen, NO2, or CN, or -QRX is ═
O, ═
S, or ═
NR′
.
- VRV;
-
33. The compound of claim 29, wherein one occurrence of WRy is —
- CH2N(R′
)2, and compounds have one of formulae IV-H-ii, V-H-ii, or IX-H-ii below, wherein m is 1-3;
- CH2N(R′
-
34. The compound of claim 29, wherein one occurrence of WRy is —
- N(R′
)2, and compounds have one of formulae IV-H-iii, V-H-iii, or IX-H-iii below, wherein m is 1-3;
- N(R′
-
35. The compound of claim 29, wherein one occurrence of WRy is —
- CON(R′
)2 and compounds have one of the formulae IV-H-iv, V-H-iv,-or IX-H-iv below, wherein m is 1-3;
- CON(R′
-
36. The compound of claim 33, 34, or 35, wherein —
- CH2N(R′
)2 is —
CH2N(CH2)3, —
CH2N(CH2CH3)2, —
CH2(optionally substituted N-piperazinyl), —
CH2(optionally substituted N-piperidinyl), or —
CH2(optionally substituted N-morpholinyl);
—
N(R′
)2 is —
N(CH2)3, —
N(CH2CH3)2, -optionally substituted N-piperazinyl, optionally substituted N-piperidinyl, or -optionally substituted N-morpholinyl; and
—
CON(R′
)2 is —
CON(CH2)3, —
CON(CH2CH3)2, —
CO(optionally substituted N-piperazinyl), —
CO(optionally substituted N-piperidinyl), or —
CO(optionally substituted N-morpholinyl).
- CH2N(R′
-
37. The compound of claim 33, 34, or 35, wherein —
- CH2N(R′
)2 is —
CH2N(CH2)3, —
CH2N(CH2CH3)2, —
CH2(optionally substituted N-piperazinyl), —
CH2(optionally substituted N-piperidinyl), or —
CH2(optionally substituted N-morpholinyl);
—
N(R′
)2 is —
N(CH2)3, —
N(CH2CH3)2, -optionally substituted N-piperazinyl, optionally substituted N-piperidinyl, or -optionally substituted N-morpholinyl; and
—
CON(R′
)2 is —
CON(CH2)3, —
CON(CH2CH3)2, —
CO(optionally substituted N-piperazinyl), —
CO(optionally substituted N-piperidinyl), —
CO(optionally substituted N-morpholinyl), —
CO(optionally substituted pyrrolidinyl), —
CO(N(H)optionally substituted pyrrolidinyl), optionally substituted pyrrolidinyl, or —
N(H)(optionally substituted pyrrolidinyl).
- CH2N(R′
-
38. The compound of claim 21, wherein n is 0, or n is 1 and T is CH2, —
- CH2CH2—
, —
CO—
or —
SO2.
- CH2CH2—
-
39. The compound of claim 21, wherein n is 0, or n is 1 and T is —
- C(H)(CH3)—
, —
C(H)(CH3)CH2—
, —
CH2C(H)(CH3)—
, or —
CH2CH2CH2—
.
- C(H)(CH3)—
-
40. The compound of claim 22, wherein n is 0, or n is 1 and T is CH2, —
- CH2CH2—
, —
CO—
or —
SO2—
;
k is 0-3 and each occurrence of QRX is independently halogen, CN, NO2, or an optionally substituted group selected from C1-4alkyl, aryl, aralkyl, —
N(R′
)2, —
CH2N(R′
)2, —
OR′
, —
CH2OR′
, —
SR′
, —
CH2SR′
, —
COOR′
, —
NRCOR′
, —
CON(R′
)2, —
SO2R′
, NR′
SO2R′
, or —
SO2N(R′
)2.
- CH2CH2—
-
55. The compound of claim 22, wherein X is —
- CH═
CH—
.
- CH═
-
56. The compound of claim 55 wherein R1 and R2, taken together with the carbon atoms to which they are bound, form an optionally substituted thieno ring.
-
63. The compound of claim 30, wherein —
- WRy groups are each independently F, Cl, Br, I, Me, Et, —
CN, —
OMe, —
SMe, —
NMe2, —
NEt2, —
COOMe, —
COOH, —
OH, —
SO2NH2, —
CON(CH3)2, —
CO(optionally substituted N-piperazinyl), —
CO(N-morpholinyl), —
CO(N-piperidinyl), —
CH2N(Me)2, —
CH2N(Et)2, or an optionally substituted group selected from C1-4alkoxy, phenyl, phenyloxy, benzyl, benzyloxy, pyridyl, pyrimidinyl, thiophene, N-morpholinyl, N-piperidinyl, N-piperazinyl, or furanyl.
- WRy groups are each independently F, Cl, Br, I, Me, Et, —
-
21. The compound of claim 2, wherein X is —
-
59. A composition comprising a compound of formula I:
- View Dependent Claims (60, 61, 62)
-
60. The composition of claim 59, wherein the compound is present in a therapeutically effective amount.
-
61. The composition of claim 59, wherein the compound is present in an amount to detectably inhibit GSK-3, SYK, Aurora-2, CDK-2, JAK-3, and/or Tec family (e.g., Tec, Btk, Itk/Emt/Tsk, Bmx, Txk/Rlk) protein kinase activity.
-
62. The composition of claim 59, further comprising an additional therapeutic agent selected from a chemotherapeutic or anti-proliferative agent, an anti-inflammatory agent, an immunomodulatory or immunosuppressive agent, a neurotrophic factor, an agent for treating cardiovascular disease, an agent for treating destructive bone disorders, an agent for treating liver disease, an anti-viral agent an agent for treating blood disorders, an agent for treating diabetes, or an agent for treating immunodeficiency disorders.
-
60. The composition of claim 59, wherein the compound is present in a therapeutically effective amount.
Specification
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Current AssigneeVertex Pharmaceuticals Incorporated
-
Original AssigneeVertex Pharmaceuticals Incorporated
-
InventorsMoon, Young-Choon, Jimenez, Juan-Miguel, Gao, Huai, Green, Jeremy, Knegtel, Ronald, Pierard, Francoise, Brenchley, Guy
-
Primary Examiner(s)Wilson; James O
-
Assistant Examiner(s)Leeser; Erich A
-
Application NumberUS10/965,695Publication NumberTime in Patent Office2,014 DaysField of Search514/267, 544/250US Class Current514/267CPC Class CodesA61K 31/496 Non-condensed piperazines c...A61P 1/04 for ulcers, gastritis or re...A61P 1/16 for liver or gallbladder di...A61P 11/02 Nasal agents, e.g. deconges...A61P 11/06 AntiasthmaticsA61P 11/08 BronchodilatorsA61P 13/12 of the kidneysA61P 17/00 Drugs for dermatological di...A61P 17/06 AntipsoriaticsA61P 17/14 for baldness or alopeciaA61P 19/00 Drugs for skeletal disordersA61P 19/02 for joint disorders, e.g. a...A61P 19/08 for bone diseases, e.g. rac...A61P 19/10 for osteoporosisA61P 25/00 Drugs for disorders of the ...A61P 25/14 for treating abnormal movem...A61P 25/16 Anti-Parkinson drugsA61P 25/18 Antipsychotics, i.e. neurol...A61P 25/28 for treating neurodegenerat...A61P 29/00 Non-central analgesic, anti...A61P 3/10 : for hyperglycaemia, e.g. an...A61P 31/12 : AntiviralsA61P 31/18 : for HIVA61P 31/22 : for herpes virusesA61P 35/00 : Antineoplastic agentsA61P 35/02 : specific for leukemiaA61P 37/00 : Drugs for immunological or ...A61P 37/02 : ImmunomodulatorsA61P 37/06 : Immunosuppressants, e.g. dr...A61P 37/08 : Antiallergic agents antiast...A61P 43/00 : Drugs for specific purposes...A61P 7/00 : Drugs for disorders of the ...A61P 9/00 : Drugs for disorders of the ...A61P 9/10 : for treating ischaemic or a...C07D 239/70 : condensed with carbocyclic ...C07D 239/84 : Nitrogen atomsC07D 333/22 : Radicals substituted by dou...C07D 333/38 : Carbon atoms having three b...C07D 333/54 : with only hydrogen atoms, h...C07D 333/70 : attached in position 2C07D 471/04 : Ortho-condensed systemsC07D 487/04 : Ortho-condensed systemsC07D 495/04 : Ortho-condensed systemsC07D 495/14 : Ortho-condensed systemsC07D 513/04 : Ortho-condensed systems