USPatentGranted
B2Multiheteroaryl compounds as inhibitors of H-PGDS and their use for treating prostaglandin D2 mediated diseases
Granted 28 May 2013 · 2 office actions
Assignee: CAYMAN CHEMICAL COMPANY, INC.
Law firm: Law firm · Log in to unlock
Attorney: Attorney · Log in to unlock
Inventors: Pil Heui Lee, Kirk Lang Olson, Stephen Douglas Barrett, Gregory W. Endres +2 · Examiner: Ebenezer O Sackey
Application
12/564,582
filed 22 Sep 2009
Publication
US 20100075990
published 25 Mar 2010
Patent· this page
US 8,450,326
granted 28 May 2013
57
Claims
1 independent
86
File wrapper
transactions
2029
20-year term
term adjustment not held
none
Litigation
checked
9
Classifications
C07D239/02, A61K31/44
87
Citations
87 cites · 0 cited by
Life of the patent
13 dated events⤢ drag to zoom
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Abstract
Multiheteroaryl compounds, their preparation, pharmaceutical compositions comprising these compounds, and their pharmaceutical use in the prevention and treatment of prostaglandin D 2 mediated diseases and conditions that may be modulated by the inhibition of hematopoietic prostaglandin D synthase (H-PGDS).
Claims
57 · 1 independent · depth 857 granted claims
›1.independentA compound of Formula (I):+56
›2.↳ 1A compound of claim 1, wherein the compound according to Formula (I) comprises a compound according to Formula (III):d2+22
›3.↳ 2A compound of claim 2, wherein the compound according to Formula (III) comprises a compound according to Formula (IV):d3
›4.↳ 2A compound of claim 2, wherein the compound according to Formula (III) comprises a compound according to Formula (V):d3+20
›5.↳ 4A compound of claim 4, wherein Y3 is N.d4+9
›6.↳ 5A compound of claim 5, wherein:neach X1, X3, X4, and X5 is hydrogen;X2 is hydrogen or fluoro;each R6 is independently hydrogen, methyl, or trifluorome…d5+8
›7.↳ 6A compound of claim 6, wherein:nZ1 is phenyl, 2-pyridyl, 3-pyridyl, or 4-pyridyl; andwherein said phenyl or pyridyl rings of Z1 are optionally substit…d6+3
›8.↳ 7A compound of claim 7, wherein:nZ1 is phenyl; andwherein said phenyl ring of Z1 is substituted with one or two of any one or combination of the follow…d7+1
›9.↳ 8A compound of claim 8, wherein said phenyl ring of Z1 is substituted with one or two of any one or combination of the following: halo or methoxy.d8
›10.↳ 7A compound of claim 7, wherein Z1 is 2-pyridyl, 3-pyridyl, or 4-pyridyl.d7
›11.↳ 6A compound of claim 6, wherein Z1 is piperidin-4-yl, piperidin-3-yl, piperidin-3(R)-yl, piperidin-3(S)-yl, piperidin-2-yl, piperidin-2(R)-yl, piperidi…d6+3
›12.↳ 11A compound of claim 11, wherein:nq is 0 or 1;Q is (C1-C4)-alkyl, —CH2CF3, (C3-C6)-cycloalkyl, phenyl, C(O)R3, CO2R3, C(O)NHR5, a five- to six-member…d7+2
›13.↳ 12A compound of claim 12, whereinnq is 1; andQ is (C1-C4)-alkyl, —CH2CF3, (C3-C6)-cycloalkyl, phenyl, a five- to six-membered heterocycle, or a five- …d8
›14.↳ 12A compound of claim 12, wherein q is 0.d8
›15.↳ 4A compound of claim 4, or a pharmaceutically acceptable salt thereof, wherein Y3 is CH.d4+9
›16.↳ 15A compound of claim 15, or a pharmaceutically acceptable salt thereof, wherein:neach X1, X3, X4, and X5 is hydrogen;X2 is hydrogen or fluoro;R6 is hyd…d5+8
›17.↳ 16A compound of claim 16, or a pharmaceutically acceptable salt thereof, wherein:nZ1 is phenyl, 2-pyridyl, 3-pyridyl, or 4-pyridyl; andsaid phenyl or py…d6+3
›18.↳ 17A compound of claim 17, wherein:nZ1 is phenyl; andsaid phenyl ring of Z1 is substituted with one or two of any one or combination of the following: ha…d7+1
›19.↳ 18A compound of claim 18, wherein said phenyl ring of Z1 is substituted with one or two of any one or combination of the following: halo or methoxy.d8
›20.↳ 17A compound of claim 17, wherein Z1 is 2-pyridyl, 3-pyridyl, or 4-pyridyl.d7
›21.↳ 16A compound of claim 16, wherein Z1 is piperidin-4-yl, piperidin-3-yl, piperidin-3(R)-yl, piperidin-3(S)-yl, piperidin-2-yl, piperidin-2(R)-yl, piperid…d6+3
›22.↳ 21A compound of claim 21, wherein:nq is 0 or 1;Q is (C1-C4)-alkyl, —CH2CF3, (C3-C6)-cycloalkyl, phenyl, C(O)R3, CO2R3, C(O)NHR5, a five- to six-member…d7+2
›23.↳ 22A compound of claim 22, wherein:nq is 1; andQ is (C1-C4)-alkyl, —CH2CF3, (C3-C6)-cycloalkyl, phenyl, a five- to six-membered heterocycle, or a five-…d8
›24.↳ 22A compound of claim 22, wherein:nq is 0;Q is hydrogen, (C1-C6)-alkyl, (CH2)pCF3, (C3-C6)- alkenyl, (C3-C6)-alkynyl, (C3-C6)-cycloalkyl, (C6-C14)-aryl,…d8
›25.↳ 1A compound of claim 1, wherein the compound according to Formula (I) comprises a compound according to Formula (VI):d2+4
›26.↳ 25A compound of claim 25, wherein the compound according to Formula (VI) comprises a compound according to Formula (VII):d3
›27.↳ 25A compound of claim 25, wherein the compound according to Formula (VI) comprises a compound according to Formula (VIII):d3+2
›28.↳ 27A compound of claim 27, wherein Y3 is N and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›29.↳ 27A compound of claim 27, wherein Y3 is CH and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›30.↳ 1A compound of claim 1, wherein the compound according to Formula (I) comprises a compound according to Formula (IX):d2+6
›31.↳ 30A compound of claim 30, wherein the compound according to Formula (IX) comprises a compound according to Formula (X):d3+2
›32.↳ 31A compound of claim 31, wherein Y3 is N and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›33.↳ 31A compound of claim 31, wherein Y3 is CH and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›34.↳ 30A compound of claim 30, wherein the compound according to Formula (IX) comprises a compound according to Formula (XI):d3+2
›35.↳ 34A compound of claim 34, wherein Y3 is N and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›36.↳ 34A compound of claim 34, wherein Y3 is CH and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›37.↳ 1A compound of claim 1, wherein the compound according to Formula (I) comprises a compound according to Formula (XII):d2+6
›38.↳ 37A compound of claim 37, wherein the compound according to Formula (XII) comprises a compound according to Formula (XIII)d3+2
›39.↳ 38A compound of claim 38, wherein Y3 is N and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›40.↳ 38A compound of claim 38, wherein Y3 is CH and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›41.↳ 37A compound of claim 37, wherein the compound according to Formula (XII) comprises a compound according to Formula (XIV):d3+2
›42.↳ 41A compound of claim 41, wherein Y3 is N and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›43.↳ 41A compound of claim 41, wherein Y3 is CH and each R6 is independently hydrogen, methyl, or trifluoromethyl.d4
›44.↳ 1A compound of claim 1, wherein the compound according to Formula (I) comprises a compound according to Formula (XV):d2+6
›45.↳ 44A compound of claim 44, wherein the compound according to Formula (XV) comprises a compound according to Formula (XVI):d3+2
›46.↳ 45A compound of claim 45, wherein Y3 is N and R6 is hydrogen, methyl, or trifluoromethyl.d4
›47.↳ 45A compound of claim 45, wherein Y3 is CH and R6 is hydrogen, methyl, or trifluoromethyl.d4
›48.↳ 44A compound of claim 44, wherein the compound according to Formula (XV) comprises a compound according to Formula (XVII):d3+2
›49.↳ 48A compound of claim 48, wherein Y3 is N and R6 is hydrogen or methyl.d4
›50.↳ 48A compound of claim 48, wherein Y3 is CH and R6 is hydrogen or methyl.d4
›51.↳ 1A compound of claim 1, wherein the compound according to Formula (I) comprises a compound according to Formula (XVIII):d2+3
›52.↳ 51A compound of claim 51, wherein the compound according to Formula (XVIII) comprises a compound according to Formula (XIX):d3+2
›53.↳ 52A compound of claim 52, wherein Y3 is N.d4
›54.↳ 52A compound of claim 52, wherein Y3 is CH.d4
›55.↳ 1A pharmaceutical composition comprising a compound of claim 1.d2
›56.↳ 1A method of treating a disease or condition mediated at least in part by prostaglandin D2 produced by H-PGDS, in a subject in need of such treatment, …d2
›57.↳ 1A pharmaceutical composition comprising a compound of claim 1 and a second pharmacologically active compound.d2
Classifications
9 codesIPC · International Patent Classification
Section A — Human necessities
- A61K31/44
Section C — Chemistry; metallurgy
- C07D239/02
- C07D239/42
- C07D401/04
USPC · US Patent Classification
514/256544/333544/335546/272.7514/340
Claim changes
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Pendency
3.7 y
1,344 days filing → grant
Office actions
1
after a restriction
Responses
2
2 RCE
Examiner
Ebenezer O Sackey
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Citations: 87 back · 0 forward
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2 priority documentsPriority
22 Sep 2008
earliest claimed
›Priority documents — 2
| Type | Document | Date |
|---|---|---|
| provisional | US 61098942 | 22 Sep 2008 |
| related publication | US 20100075990 A1 | 25 Mar 2010 |
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