JP2012524791A - アリールスルホンアミドccr3アンタゴニスト - Google Patents
アリールスルホンアミドccr3アンタゴニスト Download PDFInfo
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- JP2012524791A JP2012524791A JP2012507334A JP2012507334A JP2012524791A JP 2012524791 A JP2012524791 A JP 2012524791A JP 2012507334 A JP2012507334 A JP 2012507334A JP 2012507334 A JP2012507334 A JP 2012507334A JP 2012524791 A JP2012524791 A JP 2012524791A
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- JP
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- Prior art keywords
- alkyl
- optionally substituted
- heterocyclyl
- aryl
- heteroaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000004421 aryl sulphonamide group Chemical group 0.000 title abstract description 7
- NDZYPHLNJZSQJY-QNWVGRARSA-N 1-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-[(1r,2s)-2-[[(3s)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexyl]urea Chemical compound CC1=C(C(=O)C)SC(NC(=O)N[C@H]2[C@@H](CCCC2)CN2C[C@H](CC=3C=CC(F)=CC=3)CCC2)=N1 NDZYPHLNJZSQJY-QNWVGRARSA-N 0.000 title description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 89
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 76
- 201000010099 disease Diseases 0.000 claims abstract description 38
- 208000035475 disorder Diseases 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 38
- 208000024891 symptom Diseases 0.000 claims abstract description 23
- 230000000694 effects Effects 0.000 claims abstract description 13
- 230000001404 mediated effect Effects 0.000 claims abstract description 12
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims abstract 4
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims abstract 4
- -1 chloro, cyano, nitro, methyl Chemical group 0.000 claims description 322
- 125000000217 alkyl group Chemical group 0.000 claims description 196
- 150000001875 compounds Chemical class 0.000 claims description 147
- 125000003118 aryl group Chemical group 0.000 claims description 134
- 125000000623 heterocyclic group Chemical group 0.000 claims description 128
- 125000005843 halogen group Chemical group 0.000 claims description 127
- 125000001072 heteroaryl group Chemical group 0.000 claims description 122
- 239000000203 mixture Substances 0.000 claims description 112
- 125000001424 substituent group Chemical group 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 95
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 87
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 64
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 59
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 42
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 41
- 125000001153 fluoro group Chemical group F* 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 33
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- 125000002541 furyl group Chemical group 0.000 claims description 32
- 125000002757 morpholinyl group Chemical group 0.000 claims description 32
- 229940002612 prodrug Drugs 0.000 claims description 32
- 239000000651 prodrug Substances 0.000 claims description 32
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 31
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 239000012453 solvate Substances 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 25
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 25
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 24
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 24
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 21
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 20
- 208000006673 asthma Diseases 0.000 claims description 19
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 15
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 201000010105 allergic rhinitis Diseases 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 11
- 125000005605 benzo group Chemical group 0.000 claims description 11
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 102000004499 CCR3 Receptors Human genes 0.000 claims description 9
- 108010017316 CCR3 Receptors Proteins 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 239000002775 capsule Substances 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 8
- 201000004681 Psoriasis Diseases 0.000 claims description 8
- 201000008937 atopic dermatitis Diseases 0.000 claims description 8
- 201000004624 Dermatitis Diseases 0.000 claims description 7
- 210000003979 eosinophil Anatomy 0.000 claims description 7
- 125000005412 pyrazyl group Chemical group 0.000 claims description 7
- 208000010668 atopic eczema Diseases 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 206010003557 Asthma exercise induced Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 5
- 208000004657 Exercise-Induced Asthma Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 5
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 5
- 208000024695 exercise-induced bronchoconstriction Diseases 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 201000009961 allergic asthma Diseases 0.000 claims description 4
- 208000010247 contact dermatitis Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010012442 Dermatitis contact Diseases 0.000 claims description 3
- 208000004262 Food Hypersensitivity Diseases 0.000 claims description 3
- 206010016946 Food allergy Diseases 0.000 claims description 3
- 208000019693 Lung disease Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 210000003651 basophil Anatomy 0.000 claims description 3
- 235000020932 food allergy Nutrition 0.000 claims description 3
- 210000003630 histaminocyte Anatomy 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
- YGXPZAIFIGOFMB-UHFFFAOYSA-N 4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine-1-carbaldehyde Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C=O)=C1 YGXPZAIFIGOFMB-UHFFFAOYSA-N 0.000 claims description 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims description 2
- 208000032671 Allergic granulomatous angiitis Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 208000006344 Churg-Strauss Syndrome Diseases 0.000 claims description 2
- 206010010741 Conjunctivitis Diseases 0.000 claims description 2
- 208000018428 Eosinophilic granulomatosis with polyangiitis Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- 208000036284 Rhinitis seasonal Diseases 0.000 claims description 2
- 206010052568 Urticaria chronic Diseases 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000024376 chronic urticaria Diseases 0.000 claims description 2
- 201000001564 eosinophilic gastroenteritis Diseases 0.000 claims description 2
- 206010024378 leukocytosis Diseases 0.000 claims description 2
- 208000008585 mastocytosis Diseases 0.000 claims description 2
- 230000000414 obstructive effect Effects 0.000 claims description 2
- 239000006186 oral dosage form Substances 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
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- 208000016557 Acute basophilic leukemia Diseases 0.000 claims 1
- 206010065563 Eosinophilic bronchitis Diseases 0.000 claims 1
- 239000006207 intravenous dosage form Substances 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 49
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- 101150004010 CXCR3 gene Proteins 0.000 description 41
- 239000004480 active ingredient Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 235000002639 sodium chloride Nutrition 0.000 description 36
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 23
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
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Abstract
【選択図】なし
Description
本出願は、2009年4月22日出願の米国仮出願番号第61/171,780号について優先権を主張する。その開示は、その全体において、引用により本明細書中に取り込まれている。
(分野)
本明細書中に提供されるものは、CCR3活性の調節に有用なアリールスルホンアミド及びその医薬組成物である。また、本明細書中に提供されるものは、CCR3媒介障害、疾患又は状態の1つ以上の症状を治療、予防又は改善するためのそれらの使用の方法である。
本明細書中に提供されるものは、式Iのアリールスルホンアミド:
式中:
R1、R2、R3、R4、R5及びR6は、それぞれ独立に、(a) 水素、ハロ、シアノ、ニトロ又はグアニジン;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリル;又は(c) -C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-OR1a、-OC(O)R1a、-OC(O)OR1a、-OC(O)NR1bR1c、-OC(=NR1a)NR1bR1c、-OS(O)R1a、-OS(O)2R1a、-OS(O)NR1bR1c、-OS(O)2NR1bR1c、-NR1bR1c、-NR1aC(O)R1d、-NR1aC(O)OR1d、-NR1aC(O)NR1bR1c、-NR1aC(=NR1d)NR1bR1c、-NR1aS(O)R1d、-NR1aS(O)2R1d、-NR1aS(O)NR1bR1c、-NR1aS(O)2NR1bR1c、-SR1a、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
R7は、(a) ハロ、シアノ、ニトロ、オキソ、又はグアニジン;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15 アラルキル、ヘテロアリール、又はヘテロシクリル;又は(c) -C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-OR1a、-OC(O)R1a、-OC(O)OR1a、-OC(O)NR1bR1c、-OC(=NR1a)NR1bR1c、-OS(O)R1a、-OS(O)2R1a、-OS(O)NR1bR1c、-OS(O)2NR1bR1c、-NR1bR1c、-NR1aC(O)R1d、-NR1aC(O)OR1d、-NR1aC(O)NR1bR1c、-NR1aC(=NR1d)NR1bR1c、-NR1aS(O)R1d、-NR1aS(O)2R1d、-NR1aS(O)NR1bR1c、-NR1aS(O)2NR1bR1c、-SR1a、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
Xは、O又はSであり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、C(S)NR1aC(O)NR1bR1c、-C(NR1a)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;但し、RYaは-C(O)O-t-ブチルでも-C(O)Hでもないという条件あり;
mは、0〜3の整数であり;
nは、1〜3の整数であり;
pは、0〜4の整数であり;
各R1a、R1b、R1c及びR1dは、独立に、水素、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール又はヘテロシクリルであり;又は、R1b及びR1cの各一対は、それらが結合しているN原子とともに、独立に、ヘテロアリール又はヘテロシクリルを形成し;
各アルキル、アルケニル、アルキニル、シクロアルキル、アリール、アラルキル、ヘテロシクリル及びヘテロアリールは、それぞれ独立に、下記から選択される1つ以上の基によって任意に置換される:(a) シアノ、ハロ及びニトロ;(b) 各々1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換される、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール及びヘテロシクリル;及び(c) -C(O)Ra、-C(O)ORa、-C(O)NRbRc、-C(NRa)NRbRc、-ORa、-OC(O)Ra、-OC(O)ORa、-OC(O)NRbRc、-OC(=NRa)NRbRc、-OS(O)Ra、-OS(O)2Ra、-OS(O)NRbRc、-OS(O)2NRbRc、-NRbRc、-NRaC(O)Rd、-NRaC(O)ORd、-NRaC(O)NRbRc、-NRaC(=NRd)NRbRc、-NRaS(O)Rd、-NRaS(O)2Rd、-NRaS(O)NRbRc、-NRaS(O)2NRbRc、-SRa、-S(O)Ra、-S(O)2Ra、-S(O)NRbRc、及び-S(O)2NRbRc、ここで、各Ra、Rb、Rc及びRdは、独立に、(i) 水素;(ii) 各々1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換される、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール又はヘテロシクリル;又は(iii) Rb及びRcは、それらが結合しているN原子とともに、1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換されるヘテロシクリルを形成し;
各Qは、独立に、(a) シアノ、ハロ及びニトロ;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、及びヘテロシクリル;及び(c) -C(O)Re、-C(O)ORe、-C(O)NRfRg、-C(NRe)NRfRg、-ORe、-OC(O)Re、-OC(O)ORe、-OC(O)NRfRg、-OC(=NRe)NRfRg、-OS(O)Re、-OS(O)2Re、-OS(O)NRfRg、-OS(O)2NRfRg、-NRfRg、-NReC(O)Rh、-NReC(O)ORh、-NReC(O)NRfRg、-NReC(=NRh)NRfRg、-NReS(O)Rh、-NReS(O)2Rh、-NReS(O)NRfRg、-NReS(O)2NRfRg、-SRe、-S(O)Re、-S(O)2Re、-S(O)NRfRg及び-S(O)2NRfRgからなる群から選択され;各Re、Rf、Rg、及びRhは、独立に、(i) 水素;(ii) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリルであり;又は(iii) Rf及びRgは、それらが結合しているN原子とともに、ヘテロシクリルを形成する。
本明細書中に記載される開示の理解を容易にするために、多くの用語を以下に定義する。
本明細書中に提供されるものは、CCR3活性を調節するのに有用なアリールスルホンアミドである。また、本明細書中に提供されるものは、CCR3媒介障害、疾患又は状態の治療のための化合物を含む医薬組成物、並びに該化合物及び組成物の使用方法である。
式中:
R1、R2、R3、R4、R5及びR6は、それぞれ独立に、(a) 水素、ハロ、シアノ、ニトロ又はグアニジン;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリル;又は(c) -C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-OR1a、-OC(O)R1a、-OC(O)OR1a、-OC(O)NR1bR1c、-OC(=NR1a)NR1bR1c、-OS(O)R1a、-OS(O)2R1a、-OS(O)NR1bR1c、-OS(O)2NR1bR1c、-NR1bR1c、-NR1aC(O)R1d、-NR1aC(O)OR1d、-NR1aC(O)NR1bR1c、-NR1aC(=NR1d)NR1bR1c、-NR1aS(O)R1d、-NR1aS(O)2R1d、-NR1aS(O)NR1bR1c、-NR1aS(O)2NR1bR1c、-SR1a、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
R7は、(a) ハロ、シアノ、ニトロ、オキソ、又はグアニジン;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリル;又は(c) -C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-OR1a、-OC(O)R1a、-OC(O)OR1a、-OC(O)NR1bR1c、-OC(=NR1a)NR1bR1c、-OS(O)R1a、-OS(O)2R1a、-OS(O)NR1bR1c、-OS(O)2NR1bR1c、-NR1bR1c、-NR1aC(O)R1d、-NR1aC(O)OR1d、-NR1aC(O)NR1bR1c、-NR1aC(=NR1d)NR1bR1c、-NR1aS(O)R1d、-NR1aS(O)2R1d、-NR1aS(O)NR1bR1c、-NR1aS(O)2NR1bR1c、-SR1a、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
Xは、O又はSであり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1aC(O)NR1bR1c、-C(NR1a)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
mは、0〜3の整数であり;
nは、1〜3の整数であり;
pは、0〜4の整数であり;
各R1a、R1b、R1c及びR1dは、独立に、水素、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール又はヘテロシクリルであり;又は、R1b及びR1cの各一対は、それらが結合しているN原子とともに、独立に、ヘテロアリール又はヘテロシクリルを形成し;
各アルキル、アルケニル、アルキニル、シクロアルキル、アリール、アラルキル、ヘテロシクリル及びヘテロアリールは、それぞれ独立に、下記から選択される1つ以上の基によって任意に置換される:(a)シアノ、ハロ及びニトロ;(b) 各々1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換される、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール及びヘテロシクリル;及び(c) -C(O)Ra、-C(O)ORa、-C(O)NRbRc、-C(NRa)NRbRc、-ORa、-OC(O)Ra、-OC(O)ORa、-OC(O)NRbRc、-OC(=NRa)NRbRc、-OS(O)Ra、-OS(O)2Ra、-OS(O)NRbRc、-OS(O)2NRbRc、-NRbRc、-NRaC(O)Rd、-NRaC(O)ORd、-NRaC(O)NRbRc、-NRaC(=NRd)NRbRc、-NRaS(O)Rd、-NRaS(O)2Rd、-NRaS(O)NRbRc、-NRaS(O)2NRbRc、-SRa、-S(O)Ra、-S(O)2Ra、-S(O)NRbRc、及び-S(O)2NRbRc、ここで、各Ra、Rb、Rc及びRdは、独立に、(i)水素;(ii) 各々1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換される、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール又はヘテロシクリル;又は(iii) Rb及びRcは、それらが結合しているN原子とともに、1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換されるヘテロシクリルを形成し;
各Qは、独立に、(a)シアノ、ハロ及びニトロ;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、及びヘテロシクリル;及び(c) -C(O)Re、-C(O)ORe、-C(O)NRfRg、-C(NRe)NRfRg、-ORe、-OC(O)Re、-OC(O)ORe、-OC(O)NRfRg、-OC(=NRe)NRfRg、-OS(O)Re、-OS(O)2Re、-OS(O)NRfRg、-OS(O)2NRfRg、-NRfRg、-NReC(O)Rh、-NReC(O)ORh、-NReC(O)NRfRg、-NReC(=NRh)NRfRg、-NReS(O)Rh、-NReS(O)2Rh、-NReS(O)NRfRg、-NReS(O)2NRfRg、-SRe、-S(O)Re、-S(O)2Re、-S(O)NRfRg及び-S(O)2NRfRgからなる群から選択され; 各Re、Rf、Rg、及びRhは、独立に、(i) 水素;(ii) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリルであり;又は(iii) Rf及びRgは、それらが結合しているN原子とともに、ヘテロシクリルを形成する。
式中:
R1、R2、R3、R4、R5及びR6は、それぞれ独立に、(a) 水素、ハロ、シアノ、ニトロ又はグアニジン;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリル;又は(c) -C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-OR1a、-OC(O)R1a、-OC(O)OR1a、-OC(O)NR1bR1c、-OC(=NR1a)NR1bR1c、-OS(O)R1a、-OS(O)2R1a、-OS(O)NR1bR1c、-OS(O)2NR1bR1c、-NR1bR1c、-NR1aC(O)R1d、-NR1aC(O)OR1d、-NR1aC(O)NR1bR1c、-NR1aC(=NR1d)NR1bR1c、-NR1aS(O)R1d、-NR1aS(O)2R1d、-NR1aS(O)NR1bR1c、-NR1aS(O)2NR1bR1c、-SR1a、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
R7は、(a) ハロ、シアノ、ニトロ、オキソ、又はグアニジン;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリル;又は(c) -C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-OR1a、-OC(O)R1a、-OC(O)OR1a、-OC(O)NR1bR1c、-OC(=NR1a)NR1bR1c、-OS(O)R1a、-OS(O)2R1a、-OS(O)NR1bR1c、-OS(O)2NR1bR1c、-NR1bR1c、-NR1aC(O)R1d、-NR1aC(O)OR1d、-NR1aC(O)NR1bR1c、-NR1aC(=NR1d)NR1bR1c、-NR1aS(O)R1d、-NR1aS(O)2R1d、-NR1aS(O)NR1bR1c、-NR1aS(O)2NR1bR1c、-SR1a、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
Xは、O又はSであり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;但し、RYaが、-C(O)O-t-ブチルでも-C(O)Hでもないことを条件とし;
mは、0〜3の整数であり;
nは、1〜3の整数であり;
pは、0〜4の整数であり;
各R1a、R1b、R1c及びR1dは、独立に、水素、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール又はヘテロシクリルであり;又は、R1b及びR1cの各一対は、それらが結合しているN原子とともに、独立に、ヘテロアリール又はヘテロシクリルを形成し;
各アルキル、アルケニル、アルキニル、シクロアルキル、アリール、アラルキル、ヘテロシクリル及びヘテロアリールは、それぞれ独立に、下記から選択される1つ以上の基によって任意に置換される:(a)シアノ、ハロ及びニトロ;(b) 各々1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換される、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール及びヘテロシクリル;及び(c) -C(O)Ra、-C(O)ORa、-C(O)NRbRc、-C(NRa)NRbRc、-ORa、-OC(O)Ra、-OC(O)ORa、-OC(O)NRbRc、-OC(=NRa)NRbRc、-OS(O)Ra、-OS(O)2Ra、-OS(O)NRbRc、-OS(O)2NRbRc、-NRbRc、-NRaC(O)Rd、-NRaC(O)ORd、-NRaC(O)NRbRc、-NRaC(=NRd)NRbRc、-NRaS(O)Rd、-NRaS(O)2Rd、-NRaS(O)NRbRc、-NRaS(O)2NRbRc、-SRa、-S(O)Ra、-S(O)2Ra、-S(O)NRbRc、及び-S(O)2NRbRc、ここで、各Ra、Rb、Rc及びRdは、独立に、(i)水素;(ii) 各々1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換される、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール又はヘテロシクリル;又は(iii) Rb及びRcは、それらが結合しているN原子とともに、1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換されるヘテロシクリルを形成し;
各Qは、独立に、(a)シアノ、ハロ及びニトロ;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、及びヘテロシクリル;及び(c) -C(O)Re、-C(O)ORe、-C(O)NRfRg、-C(NRe)NRfRg、-ORe、-OC(O)Re、-OC(O)ORe、-OC(O)NRfRg、-OC(=NRe)NRfRg、-OS(O)Re、-OS(O)2Re、-OS(O)NRfRg、-OS(O)2NRfRg、-NRfRg、-NReC(O)Rh、-NReC(O)ORh、-NReC(O)NRfRg、-NReC(=NRh)NRfRg、-NReS(O)Rh、-NReS(O)2Rh、-NReS(O)NRfRg、-NReS(O)2NRfRg、-SRe、-S(O)Re、-S(O)2Re、-S(O)NRfRg及び-S(O)2NRfRgからなる群から選択され;各Re、Rf、Rg、及びRhは、独立に、(i) 水素;(ii) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリルであり;又は(iii) Rf及びRgは、それらが結合しているN原子とともに、ヘテロシクリルを形成する。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、ハロ又はC1-6アルキルであり;
R6は、シアノ又はニトロであり;
R7は、C1-6アルキルであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0、1、2、3、又は4であり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1aC(O)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)2R1a又は-S(O)2NR1bR1cであり;各R1a及びR1cは、独立に、(a)水素;(b) 独立にシアノ、ハロ、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、ヘテロシクリル、-C(O)Ra、-C(O)ORa、及び-SRaから選択される1、2、又は3つの置換基により任意に置換される、C1-6アルキル、ここで、シクロアルキル、アリール、ヘテロアリール及びヘテロシクリルは、それぞれ、独立にハロ又はC1-6アルキルである1、2、又は3つの置換基により更に任意に置換される;(c) 任意にC6-14アリールにより置換される、C1-6アルケニル;(d) 任意に1又は2つのC1-6アルキルにより置換される、C3-7シクロアルキル;(e) 独立にハロ、ニトロ、シアノ、-ORa、-C(O)Ra及びC1-6アルキルから選択される1、2、又は3つの置換基により任意に置換される、C6-14アリール、ここで、アルキルは、1、2、又は3つのハロにより更に任意に置換される;(f) 独立にハロ又はC1-6アルキルである1つ、2つ又は3つの置換基により任意に置換される、ヘテロアリール;又は(g) ヘテロシクリルであり;R1bは、水素又はC1-6アルキルである。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、ハロ又はC1-6アルキルであり;
R6は、シアノ又はニトロであり;
R7は、C1-6アルキルであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0、1、2、3、又は4であり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1aC(O)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)2R1a又は-S(O)2NR1bR1cであり;各R1a及びR1cは、独立に、(a) 水素;又は(b) 独立にハロ、シアノ、ニトロ、C1-6アルキル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、ヘテロシクリル、-ORa、-SRa、及び-C(O)Raから選択される1又は2つの置換基により任意に置換される、C1-6アルキル、C2-6アルケニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール又はヘテロシクリルであり、ここで、Raは本明細書中に定義されるものであり、アルキル、シクロアルキル、アリール、ヘテロアリール及びヘテロシクリルは、それぞれ、独立にハロ又はC1-6アルキルである1又は2つの置換基により更に任意に置換される;R1bは、水素又はC1-6アルキルである。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、ハロ又はC1-6アルキルであり;
R6は、シアノ又はニトロであり;
R7は、C1-6アルキルであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0、1、2、3、又は4であり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1aC(O)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)2R1a又は-S(O)2NR1bR1cであり;各R1a及びR1cは、独立に、(a) 水素;又は(b) 独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、アセチル、プロピオニル及びエトキシカルボニルから選択される1又は2つの置換基により任意に置換される、C1-6アルキル、C2-6アルケニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール又はヘテロシクリルであり;R1bは、水素又はC1-6アルキルである。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、ハロ又はC1-6アルキルであり;
R6は、シアノ又はニトロであり;
R7は、C1-6アルキルであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0、1、2、3、又は4であり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1aC(O)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)2R1a又は-S(O)2NR1bR1cであり;R1a及びR1cは、それぞれ独立に、(a)水素;(b) 任意にクロロ、シアノ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、プロピオニル、及びエトキシカルボニルから選択される置換基により置換される、C1-6アルキル;(c) 任意にフェニルにより置換される、C2-6アルケニル;(d) C3-7シクロアルキル;(e) 各々独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ及びアセチルから選択される1又は2つの置換基により任意に置換される、C6-14アリール;(f) 任意に1又は2つのメチルにより置換される、ヘテロアリール;又は(g) ヘテロシクリルであり;R1bは、水素又はC1-6アルキルである。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、クロロ又はメチルであり;
R6は、シアノ又はニトロであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0であり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1aC(O)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)2R1a又は-S(O)2NR1bR1cであり;R1a及びR1cは、それぞれ独立に、(a)水素;(b) 各々任意にクロロ、シアノ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、プロピオニル、及びエトキシカルボニルから選択される置換基により置換される、メチル、エチル、プロピル(例えば、n-プロピル又はイソプロピル)、ブチル(例えば、n-ブチル、2-ブチル、イソブチル、又はt-ブチル)、又はペンチル(例えば、n-ペンチル、2-ペンチル、3-ペンチル、2-メチルブチル、3-メチルブチル、1,1-ジメチルプロピル、1,2-ジメチルプロピル、又は2,2-ジメチルプロピル);(c) 各々任意にフェニルにより置換される、エテニル又はアリル;(d) シクロブチル、シクロペンチル又はシクロヘキシル;(e) 各々独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ及びアセチルから選択される1又は2つの置換基により任意に置換される、フェニル;(f) 各々任意に1又は2つのメチルにより任意に置換されるフラニル、チエニル、イソオキサゾリル、ピラゾリル、1,2,3-チアジアゾリル、ピリジニル、ピラジル、ベンゾフラニル、ベンゾ[c][l,2,5]オキサジアゾリル、ベンゾチエニル又はベンゾチアゾリル;又は(g) モルフォリニルであり;R1bは、水素、メチル又はエチルである。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、クロロ又はメチルであり;
R6は、シアノ又はニトロであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0であり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1bC(O)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)2R1a又は-S(O)2NR1bR1cであり;R1a及びR1cは、独立に、水素、メチル、エチル、プロピル(例えば、n-プロピル又はイソプロピル)、ブチル(例えば、n-ブチル、2-ブチル、イソブチル又はt-ブチル)、又はペンチル(例えば、n-ペンチル、2-ペンチル、3-ペンチル、2-メチルブチル、3-メチルブチル、1,1-ジメチルプロピル、1,2-ジメチルプロピル又は2,2-ジメチルプロピル)、クロロエチル、クロロプロピル、クロロブチル、エトキシカルボニルエチル、メチルチオプロピル、シアノメチル、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチルメチル、ベンジル、クロロベンジル、フラニルエムチル(furanylemthyl)、モルフォリニルエチル、プロピオニルエチル、エテニル、アリル、フェニルエテニル、シクロブチル、シクロペンチル、シクロヘキシル、フェニル、クロロフェニル(例えば、2-クロロフェニル、3-クロロフェニル又は4-クロロフェニル)、フルオロフェニル(例えば、2-フルオロフェニル、3-フルオロフェニル又は4-フルオロフェニル)、シアノフェニル(例えば、2-シアノフェニル、3-シアノフェニル又は4-シアノフェニル)、ニトロフェニル(例えば、2-ニトロフェニル、3-ニトロフェニル又は4-ニトロフェニル)、メチルフェニル(例えば、2-メチルフェニル、3-メチルフェニル又は4-メチルフェニル)、トリフルオロメチルフェニル(例えば、2-トリフルオロメチルフェニル、3-トリフルオロメチルフェニル又は4-トリフルオロメチルフェニル)、エチルフェニル(例えば、2-エチルフェニル、3-エチルフェニル又は4-エチルフェニル)、メトキシフェニル(例えば、2-メトキシフェニル、3-メトキシフェニル又は4-メトキシフェニル)、アセチルフェニル(例えば、2-アセチルフェニル、3-アセチルフェニル又は4-アセチルフェニル)、ジクロロフェニル(例えば、2,3-ジクロロフェニル、2,4-ジクロロフェニル、2,5-ジクロロフェニル、2,6-ジクロロフェニル、3,4-ジクロロフェニル又は3,5-ジクロロフェニル)、フラニル(例えば、フラン-2-イル又はフラン-3-イル)、チエニル(例えば、チエン-2-イル又はチエン-3-イル)、メチル-チエニル、イソオキサゾリル、ジメチルピラゾリル、メチル-1,2,3-チアジアゾリル、ピリジニル(例えば、ピリジン-2-イル、ピリジン-3-イル又はピリジン-4-イル)、ピラジル(例えば、2-ピラジル又は3-ピラジル)、ベンゾフラニル、ベンゾ[c][l,2,5]オキサジアゾリル、ベンゾチエニル、ベンゾチアゾリル、又はモルフォリニルであり;各R1bは、独立に、水素、メチル又はエチルである。
R1は、水素であり;
R2は、クロロ又はメチルであり;
R3は、水素であり;
R4は、クロロ又はメチルであり;
R5は、水素であり;
R6は、シアノであり;
Xは、O又はSであり;
mは、1であり;
nは、1であり;
pは、0であり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1aC(O)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)2R1a又は-S(O)2NR1bR1cであり;各R1a及びR1cは、独立に、水素、メチル、エチル、イソプロピル、イソブチル、t-ブチル、1,1-ジメチルプロピル、2,2-ジメチルプロピル、2-クロロエチル、3-クロロプロピル、4-クロロブチル、2-エトキシカルボニルエチル、3-メチルチオプロピル、1-シアノメチル、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチルメチル、ベンジル、3-クロロベンジル、フラン-2-イルエムチル(furan-2-ylemthyl)、2-モルフォリン-4-イルエチル、2-プロピオニルエチル、エテニル、アリル、2-フェニルエテニル、シクロブチル、シクロペンチル、シクロヘキシル、フェニル、2-クロロフェニル、3-クロロフェニル、4-クロロフェニル、2-フルオロフェニル、3-フルオロフェニル、4-フルオロフェニル、4-シアノフェニル、4-ニトロフェニル、2-メチルフェニル、3-メチルフェニル、4-メチルフェニル、4-トリフルオロメチルフェニル、4-エチルフェニル、4-メトキシフェニル、3-アセチルフェニル、3,4-ジクロロフェニル、フラン-2-イル、チエン-2-イル、3-メチル-チエン-2-イル、イソオキサゾール-5-イル、2,5-ジメチルピラゾール-3-イル、4-メチル-1,2,3-チアジアゾール-5-イル、ピリジン-2-イル、2-ピラジル、ベンゾフラン-2-イル、ベンゾ[c][l,2,5]オキサジアゾール-5-イル、ベンゾチエン-2-イル、ベンゾチアゾール-2-イル、又はモルフォリン-4-イルであり;各R1bは、独立に水素、メチル又はエチルである。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、ハロ又はC1-6アルキルであり;
R6は、シアノ又はニトロであり;
R7は、C1-6アルキルであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0、1、2、3、又は4であり;
RYaは、-C(O)R1a、-C(O)NR1bR1c又は-S(O)2R1aであり;R1a及びR1cは、それぞれ独立に、C1-6アルキル;任意に1、2 C1-6アルキルにより置換される、C3-7シクロアルキル;又は任意に1つ以上のハロ又はC1-6アルキルにより置換される、C6-14アリールであり、ここで、アルキルは1、2又は3つのハロにより更に任意に置換される;R1bは、水素である。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、ハロ又はC1-6アルキルであり;
R6は、シアノ又はニトロであり;
R7は、C1-6アルキルであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0、1、2、3、又は4であり;
RYaは、-C(O)R1a、-C(O)NR1bR1c又は-S(O)2R1aであり;R1a及びR1cは、各々独立に、C1-6アルキルであり;任意に2つのメチル基により置換される、C3-7シクロアルキル;又は任意にフルオロ、クロロ、メチル、トリフルオロメチル又はエチルにより置換される、C6-14アリール;R1bは、水素である。
R1、R2、R3、R4及びR5は、それぞれ独立に、水素、クロロ又はメチルであり;
R6は、シアノ又はニトロであり;
Xは、O又はSであり;
mは、0、1又は2であり;
nは、1又は2であり;
pは、0であり;
RYaは、-C(O)R1a、-C(O)NR1bR1c又は-S(O)2R1aであり;R1a及びR1cは、それぞれ独立に、メチル、エチル、プロピル(例えば、n-プロピル又はイソプロピル)、ブチル(例えば、n-ブチル、2-ブチル、イソブチル又はt-ブチル)、ペンチル(例えば、n-ペンチル、2-ペンチル、3-ペンチル、2-メチルブチル、3-メチルブチル、1,1-ジメチルプロピル、1,2-ジメチルプロピル又は2,2-ジメチルプロピル)、シクロブチル、シクロペンチル、シクロヘキシル、ジメチルビシクロ[2.2.1]ヘプチル(例えば、7,7-ジメチルビシクロ[2.2.1]-ヘプチル)、フェニル、フルオロフェニル(例えば、2-フルオロフェニル、3-フルオロフェニル又は4-フルオロフェニル)、クロロフェニル(例えば、2-クロロフェニル、3-クロロフェニル又は4-クロロフェニル)、メチルフェニル(例えば、2-メチルフェニル、3-メチルフェニル又は4-メチルフェニル)、トリフルオロメチルフェニル(例えば、2-トリフルオロメチルフェニル、3-トリフルオロメチルフェニル又は4-トリフルオロメチルフェニル)、又はエチルフェニル(例えば、2-エチルフェニル、3-エチルフェニル又は4-エチルフェニル)であり;R1bは、水素である。
R1は、水素であり;
R2は、クロロ又はメチルであり;
R3は、水素であり;
R4は、クロロ又はメチルであり;
R5は、水素であり;
R6は、シアノであり;
Xは、O又はSであり;
mは、1であり;
nは、1であり;
pは、0であり;
RYaは、-C(O)R1a、-C(O)NR1bR1c又は-S(O)2R1aであり;R1a及びR1cは、それぞれ独立に、メチル、エチル、イソプロピル、イソブチル、t-ブチル、1,1-ジメチルプロピル、2,2-ジメチルプロピル、シクロブチル、シクロペンチル、シクロヘキシル、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、2-クロロフェニル、4-クロロフェニル、2-フルオロフェニル、3-フルオロフェニル、4-フルオロフェニル、2-メチルフェニル、3-メチルフェニル、4-メチルフェニル、4-トリフルオロメチルフェニル、又は4-エチルフェニルであり;R1bは、水素である。
本明細書中に提供される化合物は、当業者に知られている任意の方法により調製、単離、又は得ることができる。例えば、式Iの化合物は、スキーム1に示すように調製することができる。ここで、P1は、水素、又は例えばBoc、Cbz又はFmocなどのアミノ保護基であり;X1は、例えば、クロロ、ブロモ、ヨード、イミダゾール又はカルボキシラートなどの離脱基である。
本明細書中に提供されるものは、本明細書中に提供される化合物、例えば、その鏡像異性体、鏡像異性体の混合物、2以上のジアステレオマーの混合物、互変異性体、若しくは2以上の互変異性体の混合物を含む、活性成分としての式Iの化合物、又はその医薬として許容し得る塩、溶媒和物、水和物、若しくはプロドラッグなどを、医薬として許容し得るビヒクル、担体、希釈剤若しくは賦形剤、又はそれらの混合物と組み合わせて含む医薬組成物である。
経口投与のための本明細書中に提供される医薬組成物は、経口投与のための固体、半固体、又は液体剤形で提供することができる。本明細書中で用いられる、経口投与はまた、頬、舌及び舌下投与を含む。適切な経口剤形は、錠剤、ファストメルト(fastmelt)、咀嚼錠、カプセル、ピル、ストリップ、トローチ、ロゼンジ、パステル、カシェ剤、ペレット、医薬用チューインガム、混合散剤、沸騰又は非沸騰散剤又は顆粒、経口霧、溶液、エマルジョン、懸濁液、ウェーハ、粉砂糖、エリキシル及びシロップを含むが、これらに限定されない。活性成分に加えて、医薬組成物は、結合剤、充填剤、希釈剤、崩壊剤、湿潤剤、潤滑油、流動促進剤、着色剤、色素移動阻害剤、甘味剤、香料、乳化剤、懸濁及び分散剤、防腐剤、溶媒、非水性液体溶液、有機酸及び二酸化炭素の供給源を含むがこれらに限定されない、1以上の医薬として許容し得る担体又は賦形剤を含むことができる。
本明細書中に提供される医薬組成物は、局所又は全身投与のために、注射、注入又は埋め込みによって、非経口的に投与することができる。本明細書で用いられる非経口投与は、静脈、動脈内、腹腔内、鞘内、心室内、尿管内、胸骨内、頭蓋内、筋肉内、滑液嚢内、膀胱内及び皮下投与を含む。
本明細書中に提供される医薬組成物は、局所的に皮膚、開口部又は粘膜に投与することができる。本明細書で用いられる局所投与は、皮(内)、結膜、歯冠内、眼球内、眼、耳、経皮、鼻、膣、尿道、呼吸器官、及び直腸投与を含む。
本明細書中に提供される医薬組成物は、改変放出(modified release)剤形として製剤化することができる。本明細書中で用いられる用語「改変放出」は、同じ経路により投与されるときに、活性成分の放出の速度又は場所が、即時剤形(immediate dosage form)のものと異なる剤形を意味する。改変放出剤形は、遅延、延長、長期、持続、パルス型、制御、促進、急速、標的化、プログラム化放出、及び胃貯留剤形を含むが、これらに制限されない。改変放出剤形の医薬組成物は、マトリックス制御放出デバイス、浸透圧制御放出デバイス、多粒子制御放出デバイス、イオン交換樹脂、腸溶コーティング、多層コーティング、マイクロスフェア、リポソーム、及びそれらの組み合わせを含むが、これらに限定されない、様々な改変放出手段、及び当業者に公知の方法を用いて調製することができる。活性成分の放出速度は、活性成分の粒径及び多形を変化させることにより変更することもできる。
改変放出剤形の本明細書中に提供される医薬組成物は、当業者に公知のマトリックス制御放出デバイスを用いて製造することができる(Takadaらの文献、「制御薬剤送達の百科事典(Encyclopedia of Controlled Drug Delivery)」、Vol. 2, Mathiowitz編集、Wiley、1999年を参照されたい。)。
改変放出剤形の本明細書中に提供される医薬組成物は、一容器系、二容器系、非対称膜技術(AMT)及び押出コア系(extruding core system)(ECS)を含むが、これらに限定されない、浸透圧制御放出デバイスを用いて製造することができる。一般に、このようなデバイスは、少なくとも2つの成分を有する:(a)活性成分を含むコア;及び(b)該コアを封入する、少なくとも1つの送達ポートを有する半透膜である。半透膜は、送達ポートによる押出によって薬剤放出するように、使用の水性環境からコアへの水の流入を制御する。
改変放出剤形の本明細書中に提供される医薬組成物は、直径約10μm〜約3mm、約50μm〜約2.5mm、又は約100μm〜約1mmの多数の粒子、顆粒又はペレットを含む、多粒子制御放出デバイスとして製造することができる。このような多粒子は、湿式又は乾式造粒、押出/スフェロニゼーション(spheronization)、ローラー圧縮、溶融凝固、及びスプレーコーティングシードコア(spray-coating seed cores)によってなどの当業者に公知の方法によって製造することができる。例えば、Multiparticulate Oral Drug Delivery;Marcel Dekker:1994;及びPharmaceutical Pelletization Technology;Marcel Dekker:1989を参照されたい。
本明細書中に提供される医薬組成物は、リポソーム、再封赤血球(resealed erythrocyte-)、及び抗体ベース送達システムを含む、治療される対象の身体の特定組織、レセプター、又は他の領域に標的化されるように製剤化することができる。例を挙げると、下記文献に開示されるものを含むが、これらに制限されない:米国特許第6,316,652号;第6,274,552号;第6,271,359号;第6,253,872号;第6,139,865号;第6,131,570号;第6,120,751号;第6,071,495号;第6,060,082号;第6,048,736号;第6,039,975号;第6,004,534号;第5,985,307号;第5,972,366号;第5,900,252号;第5,840,674号;第5,759,542号;及び第5,709,874号。
一実施態様において、対象に、治療的有効量の本明細書中に提供される化合物、例えば、その鏡像異性体、鏡像異性体の混合物、2以上のジアステレオマーの混合物、互変異性体、若しくは2以上の互変異性体の混合物を含む式Iの化合物;又はその医薬として許容し得る塩、溶媒和物、水和物、若しくはプロドラッグを投与することを含む、対象のCCR3に関連した障害、疾患又は状態の1つ以上の症状を治療、予防又は改善するための方法を提供する。一実施態様において、対象は、哺乳類である。別の実施態様において、対象は、ヒトである。
4-クロロ-3-ニトロベンゾニトリル (12.00 g, 65.75 mmol)のTHF溶液に、炭酸カリウム (45.58 g, 328.70 mmol)及び3,5-ジメチルフェノール (9.658 g, 78.88 mmol)を加えた。反応混合物を17時間還流すると、出発物質が消費された(TLC, ヘキサン中25% EtOAc)。その後、反応混合物を室温に冷却し、炭酸カリウムを濾過し、多量のEtOAcで洗浄した。濾液を飽和炭酸水素ナトリウム溶液、水、及び飽和塩化ナトリウム溶液で順次洗浄し、無水MgSO4で乾燥し、濾過し、真空下で濃縮し、粗生成物を黄色固体として得た。固体をヘキサンで粉末化し、濾過し、化合物21を淡黄色粉末として与えた。(15.022g、85.2% 収率、100% HPLC純度)。
化合物21 (15.00 g, 55.91 mmol)のTHF (250 mL)溶液に、ヒドロ亜硫酸ナトリウム (58.41 g, 335.5 mmol)の水(75 mL)溶液を加えた。反応混合物を、90℃で撹拌した。24時間後に、出発物質が、TLC(ヘキサン中10%EtOAc)によってモニターされるように、消費され、反応混合物を熱から除去した。反応混合物を、生成物が残りの水中に沈殿するまで、真空下で濃縮した。沈殿物を、減圧濾過を介して回収し、水で洗浄した。生成物を真空下、40℃で一晩乾燥し、化合物22を与えた。(12.681g、95.2% 収率、99.9% HPLC純度)。
化合物22(12.00 g, 50.36 mmol)を、室温で、H2O(50.0 mL)及び濃HCl(100 mL)に加えた。その後、反応混合物を氷浴下で撹拌した。H2O(50 mL)中の亜硝酸ナトリウム(10.434 g, 151.1 mmol)を、反応混合物に0℃で滴下して加えた。反応混合物を1時間、氷浴下で撹拌した。別のフラスコにおいて、二酸化硫黄を酢酸(430 mL)を通して45分間バブリングした。その後、塩化銅二水和物(4.305 g, 25.2 mmol)を、この二酸化硫黄飽和溶液に加え、さらに30分間撹拌した。その後、この飽和二酸化硫黄溶液を氷浴下で更に5分間撹拌した。その後、化合物22を含む反応混合物を該塩化銅溶液に滴下して加えた。添加が終了後、溶液をさらに1時間書撹拌し、その後、氷水スラリーにゆっくり注ぎ、1時間撹拌した。その後、得られた沈殿物を濾過し、黄色の固体を水で洗浄し、化合物23を与えた(13.944 g, 86.1% 収率)。
氷-塩水浴下で撹拌されるピペラジン(16.144 g, 186.4 mmol)のCH2Cl2(80 mL)溶液に、化合物23(3.009 g, 9.35 mmol)のCH2Cl2(270 mL)溶液を、2日間にわたって滴下して加えた。その後、反応を74時間撹拌すると、出発物質が消費された(TLC, CH2Cl2中5% MeOH)。反応混合物を、CH2Cl2と水の間に分配した。その後、有機層を飽和塩化ナトリウム溶液で洗浄し、無水MgSO4で乾燥した。その後、有機層を真空下で濃縮し、最小量のCH2Cl2に再溶解し、順相シリカでクロマトグラフィーにかけた(MeOH/CH2Cl2)。所望の生成物を含む画分を組み合わせ、真空下で濃縮し、淡黄色油を生成した。その後、油をCH2Cl2/ジイソプロピルエーテルで粉末化し、真空濾過し、化合物24を白色粉末として与えた(2.032 g, 58.5% 収率, 95.5% HPLC純度)。
化合物24(0.102 g, 0.27 mmol)のCH2Cl2(2 mL)溶液に、プロピオニルクロライド(0.035 g, 0.38 mmol)及びトリエチルアミン(0.039 g, 0.38 mmol)を加えた。反応混合物を室温で20時間撹拌すると、出発物質が消費された(TLC, CH2Cl2中1% MeOH)。反応混合物を真空下で濃縮し、最小量のCH2Cl2に再溶解し、順相シリカでクロマトグラフィーにかけた(MeOH/CH2Cl2)。所望の生成物を含む画分を組み合わせ、真空下で濃縮し、白色粉末を得て、その後、CH2Cl2/ジイソプロピルエーテルで粉末化し、真空濾過し、所望の生成物を粉末として得た。粉末をCH2Cl2に再溶解し、順相シリカで二度目のクロマトグラフィーにかけた(MeOH/CH2Cl2)。所望の生成物を含む画分を組み合わせ、真空下で濃縮し、白色粉末を得た。粉末をジイソプロピルエーテルで粉末化し、真空濾過し、化合物57を得た(0.061g, 52.1% 収率, 96.6% HPLC純度)。
化合物24(0.100 g, 0.27 mmol)のCH2Cl2(3 mL)溶液に、イソプロピルイソシアナート(0.032 g, 0.38 mmol)及びトリエチルアミン(0.039 g, 0.38 mmol)を加えた。反応物を室温で20時間撹拌すると、出発物質が消費された(TLC, CH2Cl2中1%MeOH)。その後、反応混合物を真空下で濃縮し、最小量のCH2Cl2に再溶解し、順相シリカでクロマトグラフィーにかけた(MeOH/CH2Cl2)。所望の生成物を含む画分を組み合わせ、真空下で濃縮し、白色粉末を得て、その後、CH2Cl2/ヘキサンで粉末化し、真空濾過して、粉末を得た。粉末をCH2Cl2に再溶解し、順相シリカで二度目のクロマトグラフィーにかけた(MeOH/ CH2Cl2)。所望の生成物を含む画分を組み合わせ、真空下で濃縮し、白色粉末を得て、その後、ヘキサンで粉末化し、真空濾過して、化合物58を白色粉末として与えた(0.014g, 11.3 % 収率, 99.1% HPLC純度)。
4-(3,5-ジメチルフェノキシ)-3-(4-(4-(トリフルオロメチル)フェニルスルホニル)ピペラジン-1-イルスルホニル)ベンゾニトリル 60の調製
化合物24(0.099 g, 0.27 mmol)のCH2Cl2(3 mL)溶液に、4-(トリフルオロメチル)ベンゼン塩化スルホニル(0.093 g, 0.38 mmol)及びトリエチルアミン(0.039 g, 0.38 mmol)を加えた。反応混合物を18時間撹拌すると、出発物質が消費された(TLC, CH2Cl2中1% MeOH)。その後、反応混合物を真空下で濃縮し、最小量のCH2Cl2に再溶解し、順相シリカでクロマトグラフィーにかけた(MeOH/CH2Cl2)。所望の生成物を含む画分を組み合わせ、真空下で濃縮し、白色固体を得た。固体をジイソプロピルエーテル/ヘキサンで粉末化し、真空濾過し、化合物60を白色粉末として与えた。(0.065g, 42.2% 収率, 95.7% HPLC純度)。
濃HCl (100 mL)の氷浴冷却溶液に、2-クロロ-5-ニトロアニリン(10 g)を部分的に加えた。完全に溶解したときに、亜硝酸ナトリウム(50 mL水中6.0 g)の水溶液を滴下して加え、得られた反応混合物を0℃で1時間撹拌した。その後、上記の得られたジアゾニウムイオン溶液を、二酸化硫黄ガスで予め飽和した、塩化銅二水和物(5 g)の酢酸(500 mL)氷浴冷却混合物に慎重に加えた。得られた反応混合物を1時間、0℃で撹拌した後に、強く撹拌した氷-水スラリーに部分的に慎重に加えた。分離された固体を吸引により回収し、水ですすぎ、真空下で乾燥して、所望の生成物37をクリーム色粉末として得た(8.2 g, 55%)。
化合物37(0.600 g, 2.34 mmol)のDCM(20.00 mL)溶液に、tert-ブチル 1-ピペラジンカルボキシラート(0.566 g, 3.04 mmol)及びTEA(0.422 mL, 3.04 mmol)を加えた。反応を、TLC(ヘキサン中25% EtOAc, Rf = 0.53)でモニターした。反応混合を、出発物質の非存在により示される(TLC)ように、室温で1時間撹拌した後に終了した。水を加え、水層をDCMで2回抽出した。合わせた抽出液を水及び塩水で順次洗浄し、MgSO4で乾燥し、濾過し、真空下で蒸発させて、黄色の固体を与えた。固体を、DCM及びヘキサンで粉末化し、その後、濾過し、化合物38を黄色の固体として得た(0.789 g, 100% HPLC純度, 83% 収率)。
氷浴下で撹拌される2,5-ジクロロフェノール(0.414 g, 2.54 mmol)のTHF(20.00 mL)溶液に、NaH(0.101 g, 2.54 mmol)をゆっくり加えた。添加後、混合物を5分間撹拌した。その後、化合物38(0.790 g, 1.95 mmol)を加え、得られた反応混合物を75℃に一晩加熱した。反応をHPLCでモニターした。しかし、反応は、16時間後に完全でなかった(HPLC)ので、THFを蒸発させ、18-クラウン-6(1.057 g, 4.00 mmol)、DMF(15 mL)、及びK2CO3(0.553 g, 4.00 mmol)を加えた。反応混合物をさらに16時間、100℃に加熱し、その時には、HPLCは、反応が出発物質の非存在によって終了したことを示した。反応混合物を室温に冷却し、水(0.250 mL)を加えた。反応混合物をEtOAcで3回抽出した。合わせた抽出液を1N NaOH、水及び塩水で順次洗浄し、MgSO4で乾燥し、濾過し、真空下で蒸発した。残渣を最小量のDCMに溶解し、ヘキサン中5〜30%EtOAcの勾配を使用するクロマトグラフィーで精製した。純粋な画分を合わせて、真空下で蒸発した。得られた固体を、DCM及びヘキサンで粉末化し、その後、濾過して、化合物39を白/黄色粉末として与えた(0.120 g, 100% HPLC純度, 10.0% 収率)。
化合物39(0.100 g, 0.19 mmol)のDCM(6.00 mL)溶液に、1,4-ジオキサン(0.570 mL)中の1N HClを加えた。反応は、TLC(ヘキサン中25% EtOAc, Rf = 0.0)でモニターした。反応は、出発物質の非存在により示されるように、室温で16時間撹拌した後に終了した。反応混合物を濃縮し、残渣をMeOH(2.00 mL)に再溶解した。その後、Et2O(4.00 mL)を加え、混合物を、沈殿物が形成するまで(10分)、撹拌した。固体を濾過により回収し、化合物40を白色固体として得た(0.080 g, 100% HPLC純度, 83% 収率)。
CCR3レセプター結合アッセイ
細胞をPBSで一度洗浄し、結合バッファー(25mM HEPES pH 7.6、5mM MgCl2、1mM CaCl2、0.5% BSA、0.1% NaN3)に再懸濁した。100mLの細胞懸濁液(2x105細胞/ウェル)及び0.1nM[125I]-標識化ヒトエオタキシン/CCL11(2000Ci/mmol比活性)を、96ウェルU-型ポリプロピレンプレートに混合し、結合反応のために室温で、60分間インキュベートした。その後、細胞懸濁液を濾過プレート(#MAFB、Millipore)に移し、0.5M NaClを含む結合バッファーで3回洗浄し、シンチラント(scintillant)を加え、放射能活性をTopCount(Packard)で計数した。非特異的結合の決定のために、細胞懸濁液及び[125I]-標識化ヒトエオタキシン/CCL11を、500nMの未標識ヒトエオタキシン/CCL11の存在下でインキュベートした。Iinoらの文献, 「カニクイザルのCCケモカインレセプターCCR3の分子クローニング及び機能特性(Molecu1ar cloning and functional characterization of cynomolgus monkey (Macaca fascicularis) CC chemokine receptor, CCR3)」 Cytokine 2002, 19, 276-286を参照されたい。
Claims (47)
- 式Iの化合物:
(式中:
R1、R2、R3、R4、R5及びR6は、それぞれ独立に、(a) 水素、ハロ、シアノ、ニトロ又はグアニジン;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリル;又は(c) -C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-OR1a、-OC(O)R1a、-OC(O)OR1a、-OC(O)NR1bR1c、-OC(=NR1a)NR1bR1c、-OS(O)R1a、-OS(O)2R1a、-OS(O)NR1bR1c、-OS(O)2NR1bR1c、-NR1bR1c、-NR1aC(O)R1d、-NR1aC(O)OR1d、-NR1aC(O)NR1bR1c、-NR1aC(=NR1d)NR1bR1c、-NR1aS(O)R1d、-NR1aS(O)2R1d、-NR1aS(O)NR1bR1c、-NR1aS(O)2NR1bR1c、-SR1a、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
R7は、(a) ハロ、シアノ、ニトロ、オキソ、又はグアニジン;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15 アラルキル、ヘテロアリール、又はヘテロシクリル;又は(c) -C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(NR1a)NR1bR1c、-OR1a、-OC(O)R1a、-OC(O)OR1a、-OC(O)NR1bR1c、-OC(=NR1a)NR1bR1c、-OS(O)R1a、-OS(O)2R1a、-OS(O)NR1bR1c、-OS(O)2NR1bR1c、-NR1bR1c、-NR1aC(O)R1d、-NR1aC(O)OR1d、-NR1aC(O)NR1bR1c、-NR1aC(=NR1d)NR1bR1c、-NR1aS(O)R1d、-NR1aS(O)2R1d、-NR1aS(O)NR1bR1c、-NR1aS(O)2NR1bR1c、-SR1a、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;
Xは、O又はSであり;
RYaは、-C(O)R1a、-C(O)OR1a、-C(O)NR1bR1c、-C(S)NR1bR1c、C(S)NR1aC(O)NR1bR1c、-C(NR1a)NR1bR1c、-C(NNO2)NR1bR1c、-S(O)R1a、-S(O)2R1a、-S(O)NR1bR1c又は-S(O)2NR1bR1cであり;但し、RYaは-C(O)O-t-ブチルでないという条件であり;
mは、0〜3の整数であり;
nは、1〜3の整数であり;
pは、0〜4の整数であり;
各R1a、R1b、R1c及びR1dは、独立に、水素、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール又はヘテロシクリルであり;又は、R1b及びR1cの各一対は、それらが結合しているN原子とともに、独立に、ヘテロアリール又はヘテロシクリルを形成し;
但し、該化合物が、4-(2-(3,5-ジメチルフェノキシ)-5-ニトロフェニルスルホニル)ピペラジン-1-カルバルデヒドでないという条件であり;各アルキル、アルケニル、アルキニル、シクロアルキル、アリール、アラルキル、ヘテロシクリル及びヘテロアリールは、それぞれ独立に、下記から選択される1つ以上の基によって任意に置換される:(a) シアノ、ハロ及びニトロ;(b) 各々1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換される、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール及びヘテロシクリル;及び(c) -C(O)Ra、-C(O)ORa、-C(O)NRbRc、-C(NRa)NRbRc、-ORa、-OC(O)Ra、-OC(O)ORa、-OC(O)NRbRc、-OC(=NRa)NRbRc、-OS(O)Ra、-OS(O)2Ra、-OS(O)NRbRc、-OS(O)2NRbRc、-NRbRc、-NRaC(O)Rd、-NRaC(O)ORd、-NRaC(O)NRbRc、-NRaC(=NRd)NRbRc、-NRaS(O)Rd、-NRaS(O)2Rd、-NRaS(O)NRbRc、-NRaS(O)2NRbRc、-SRa、-S(O)Ra、-S(O)2Ra、-S(O)NRbRc、及び-S(O)2NRbRc、ここで、各Ra、Rb、Rc及びRdは、独立に、(i) 水素;(ii) 各々1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換される、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール又はヘテロシクリル;又は(iii) Rb及びRcは、それらが結合しているN原子とともに、1つ以上、一実施態様において、1つ、2つ、3つ又は4つの置換基Qによって任意に置換されるヘテロシクリルを形成し;
各Qは、独立に、(a) シアノ、ハロ及びニトロ;(b) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、及びヘテロシクリル;及び(c) -C(O)Re、-C(O)ORe、-C(O)NRfRg、-C(NRe)NRfRg、-ORe、-OC(O)Re、-OC(O)ORe、-OC(O)NRfRg、-OC(=NRe)NRfRg、-OS(O)Re、-OS(O)2Re、-OS(O)NRfRg、-OS(O)2NRfRg、-NRfRg、-NReC(O)Rh、-NReC(O)ORh、-NReC(O)NRfRg、-NReC(=NRh)NRfRg、-NReS(O)Rh、-NReS(O)2Rh、-NReS(O)NRfRg、-NReS(O)2NRfRg、-SRe、-S(O)Re、-S(O)2Re、-S(O)NRfRg及び-S(O)2NRfRgからなる群から選択され;各Re、Rf、Rg、及びRhは、独立に、(i) 水素;(ii) C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C3-7シクロアルキル、C6-14アリール、C7-15アラルキル、ヘテロアリール、又はヘテロシクリルであり;又は(iii) Rf及びRgは、それらが結合しているN原子とともに、ヘテロシクリルを形成する。)。 - RYaが、-C(O)R1a、-C(O)NR1bR1c、-C(S)NR1bR1c、-C(S)NR1aC(O)NR1bR1c、-C(NNO2)NR1bR1c、又は-S(O)2R1aである、請求項1記載の化合物。
- R1aが、(a) 水素;(b) 独立にシアノ、ハロ、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、ヘテロシクリル、-C(O)Ra、-C(O)ORa、及び-SRaから選択される1、2又は3つの置換基により任意に置換される、C1-6アルキル、ここで、シクロアルキル、アリール、ヘテロアリール、及びヘテロシクリルは、それぞれ、独立にハロ又はC1-6アルキルである1、2又は3つの置換基により更に任意に置換される;(c) 任意にC6-14アリールにより置換されるC1-6アルケニル;(d) 任意に1又は2つのC1-6アルキルにより置換されるC3-7シクロアルキル;(e) 独立にハロ、ニトロ、シアノ、-ORa、-C(O)Ra及びC1-6アルキルから選択される1、2、又は3つの置換基により任意に置換される、C6-14アリール、ここで、アルキルは、1、2、又は3つのハロにより更に任意に置換される;(f) 独立にハロ又はC1-6アルキルである1、2又は3つの置換基により任意に置換される、ヘテロアリール;又は(g) ヘテロシクリル;である、請求項1又は2記載の化合物。
- R1aが、(a) 水素;又は(b) 独立にハロ、シアノ、ニトロ、C1-6アルキル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、ヘテロシクリル、-ORa、-SRa、及び-C(O)Raから選択される1又は2つの置換基により各々任意に置換される、C1-6アルキル、C2-6アルケニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、又はヘテロシクリルであり、ここで、アルキル、シクロアルキル、アリール、ヘテロアリール及びヘテロシクリルは、それぞれ、独立にハロ又はC1-6アルキルである1又は2つの置換基により更に任意に置換される、請求項1〜3のいずれか1項記載の化合物。
- R1aが、(a) 水素;又は(b) 独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、アセチル、プロピオニル、及びエトキシカルボニルから選択される1又は2つの置換基により各々任意に置換される、C1-6アルキル、C2-6アルケニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、又はヘテロシクリル;である、請求項1〜3のいずれか1項記載の化合物。
- R1aが、(a) 水素;(b) 任意にクロロ、シアノ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、プロピオニル及びエトキシカルボニルから選択される置換基により置換される、C1-6アルキル;(c) 任意にフェニルにより置換されるC2-6アルケニル;(d) C3-7シクロアルキル;(e) 各々独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ、及びアセチルから選択される1又は2つの置換基により任意に置換される、C6-14アリール;(f) 任意に1又は2つのメチルにより置換される、ヘテロアリール;又は(g) ヘテロシクリル;である、請求項4記載の化合物。
- R1aが、(a)水素;(b) 各々任意にクロロ、シアノ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、プロピオニル、及びエトキシカルボニルから選択される置換基により置換される、メチル、エチル、プロピル、ブチル、又はペンチル;(c) 任意にフェニルにより置換される、エテニル又はアリル;(d) シクロブチル、シクロペンチル、又はシクロヘキシル;(e) 各々独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ、及びアセチルから選択される1又は2つの置換基により任意に置換される、フェニル;(f) 各々任意に1又は2つのメチルにより置換される、フラニル、チエニル、イソオキサゾリル、ピラゾリル、1,2,3-チアジアゾリル、ピリジニル、ピラジル、ベンゾフラニル、ベンゾ[c][1,2,5]オキサジアゾリル、ベンゾチエニル、又はベンゾチアゾリル;又は(g) モルフォリニル;である、請求項6記載の化合物。
- R1bが、水素又はC1-6アルキルである、請求項1〜7のいずれか1項記載の化合物。
- R1bが、水素、メチル又はエチルである、請求項8記載の化合物。
- R1cが、(a)水素;(b) 独立にシアノ、ハロ、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、ヘテロシクリル、-C(O)Ra、-C(O)ORa、及び-SRaから選択される1、2又は3つの置換基により任意に置換される、C1-6アルキル、ここで、シクロアルキル、アリール、ヘテロアリール、及びヘテロシクリルは、それぞれ、独立にハロ又はC1-6アルキルである1、2又は3つの置換基により更に任意に置換される; (c) 任意にC6-14アリールにより置換されるC1-6アルケニル;(d) 任意に1又は2つの C1-6アルキルにより置換されるC3-7シクロアルキル;(e) 独立にハロ、ニトロ、シアノ、-ORa、-C(O)Ra、及びC1-6アルキルから選択される1、2又は3つの置換基により任意に置換される、C6-14アリール、ここで、アルキルは1、2又は3つのハロにより更に任意に置換される;(f) 独立にハロ又はC1-6アルキルである1、2又は3つの置換基により任意に置換される、ヘテロアリール;又は(g) ヘテロシクリル;である、請求項1〜9のいずれか1項記載の化合物。
- R1cが、(a)水素;又は(b) 独立にハロ、シアノ、ニトロ、C1-6アルキル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、ヘテロシクリル、-ORa、-SRa、及び-C(O)Raから選択される1又は2つの置換基により各々任意に置換される、C1-6アルキル、C2-6アルケニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、又はヘテロシクリル、ここで、Raは本明細書に定義されるものであり、アルキル、シクロアルキル、アリール、ヘテロアリール、及びヘテロシクリルは、それぞれ、独立にハロ又はC1-6アルキルである1又は2つの置換基により任意に更に置換される;である、請求項1〜9のいずれか1項記載の化合物。
- R1cが、(a)水素;又は(b) 独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、アセチル、プロピオニル、及びエトキシカルボニルから選択される1又は2つの置換基により各々任意に置換される、C1-6アルキル、C2-6アルケニル、C3-7シクロアルキル、C6-14アリール、ヘテロアリール、又はヘテロシクリル;である、請求項10記載の化合物。
- R1cが、(a)水素;(b) 任意にクロロ、シアノ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、プロピオニル及びエトキシカルボニルから選択される置換基により置換される、C1-6アルキル;(c) 任意にフェニルにより置換されるC2-6アルケニル;(d) C3-7シクロアルキル;(e) 各々独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ、及びアセチルから選択される1又は2つの置換基により任意に置換される、C6-14アリール;(f) 任意に1又は2つのメチルにより置換されるヘテロアリール;又は(g) ヘテロシクリル;である、請求項12記載の化合物。
- R1cが、(a) 水素;(b) 各々任意にクロロ、シアノ、エトキシ、メチルチオ、(1S,2S,4R)-7,7-ジメチルビシクロ[2.2.1]-ヘプチル、フェニル、クロロフェニル、フラニル、モルフォリニル、プロピオニル、及びエトキシカルボニルから選択される置換基により置換される、メチル、エチル、プロピル、ブチル、又はペンチル;(c) 各々任意にフェニルにより置換されるエテニル又はアリル;(d) シクロブチル、シクロペンチル、又はシクロヘキシル;(e) 各々独立にフルオロ、クロロ、シアノ、ニトロ、メチル、トリフルオロメチル、エチル、メトキシ、及びアセチルから選択される1又は2つの置換基により任意に置換される、フェニル;(f) 各々任意に1又は2つのメチルにより置換される、フラニル、チエニル、イソオキサゾリル、ピラゾリル、1,2,3-チアジアゾリル、ピリジニル、ピラジル、ベンゾフラニル、ベンゾ[c][l,2,5]オキサジアゾリル、ベンゾチエニル、又はベンゾチアゾリル;又は(g) モルフォリニル;である、請求項12記載の化合物。
- R1、R2、R3、R4及びR5が、それぞれ独立に、水素、ハロ、又はC1-6アルキルである、請求項1〜14のいずれか1項記載の化合物。
- R1、R2、R3、R4及びR5のうちの2つが、ハロ又はC1-6アルキルであり、残りの3つが水素である、請求項15記載の化合物。
- R1、R2、R3、R4及びR5のうちの2つが、クロロ又はメチルであり、残りの3つが水素である、請求項15記載の化合物。
- R1、R3、及びR5が水素であり、R2及びR4がクロロ又はメチルである、請求項17記載の化合物。
- R2及びR4がクロロである、請求項18記載の化合物。
- R2及びR4がメチルである、請求項18記載の化合物。
- R2、R3、及びR5が水素であり、R1及びR4がクロロ又はメチルである、請求項17記載の化合物。
- R1及びR4がクロロである、請求項21記載の化合物。
- R1及びR4がメチルである、請求項21記載の化合物。
- R6がシアノ又はニトロである、請求項1〜23のいずれか1項記載の化合物。
- R7がC1-6アルキルである、請求項1〜24のいずれか1項記載の化合物。
- mが1である、請求項1〜25のいずれか1項記載の化合物。
- nが1又は2である、請求項1〜26のいずれか1項記載の化合物。
- pが0である、請求項1〜27のいずれか1項記載の化合物。
- XがOである、請求項1〜28のいずれか1項記載の化合物。
- XがSである、請求項1〜28のいずれか1項記載の化合物。
- 塩酸塩である、請求項1〜31のいずれか1項記載の化合物。
- 請求項1〜32のいずれか1項記載の化合物、又はその医薬として許容し得る塩、溶媒和物、水和物、立体異性体、又は互変異性体、及び1以上の医薬として許容し得る担体又は賦形剤を含む、医薬組成物。
- 第2の治療薬を更に含む、請求項33記載の医薬組成物。
- 単回用量投与用に製剤化される、請求項33又は34記載の医薬組成物。
- 経口、非経口、静脈内用の剤形として製剤化される、請求項35記載の医薬組成物。
- 前記経口剤形が錠剤又はカプセルである、請求項36記載の医薬組成物。
- 対象に、治療的有効量の請求項1〜32のいずれか1項記載の化合物又は請求項33〜37のいずれか1項記載の医薬組成物を投与することを含む、対象のCCR3媒介障害、疾患又は状態の1つ以上の症状を治療、予防又は改善するための方法。
- 対象に、治療的有効量の請求項1〜32のいずれか1項記載の化合物又は請求項33〜37のいずれか1項記載の医薬組成物を投与することを含む、対象の好酸球関連障害、疾患又は状態の1つ以上の症状を治療、予防又は改善するための方法。
- 対象に、治療的有効量の請求項1〜32のいずれか1項記載の化合物又は請求項33〜37のいずれか1項記載の医薬組成物を投与することを含む、対象の好塩基球関連障害、疾患又は状態の1つ以上の症状を治療、予防又は改善するための方法。
- 対象に、治療的有効量の請求項1〜32のいずれか1項記載の化合物又は請求項33〜37のいずれか1項記載の医薬組成物を投与することを含む、対象の肥満細胞関連障害、疾患又は状態の1つ以上の症状を治療、予防又は改善するための方法。
- 対象に、治療的有効量の請求項1〜32のいずれか1項記載の化合物又は請求項33〜37のいずれか1項記載の医薬組成物を投与することを含む、対象の炎症性疾患の1つ以上の症状を治療、予防又は改善するための方法。
- 前記障害、疾患又は状態が、喘息、アレルギー性喘息、運動誘発喘息、アレルギー性鼻炎、永続的なアレルギー性鼻炎、季節的なアレルギー性鼻炎、アトピー性皮膚炎、接触過敏症、接触性皮膚炎、結膜炎、アレルギー結膜炎、好酸球増加性気管支炎、食物アレルギー、好酸球性胃腸炎、炎症性大腸疾患、潰瘍性大腸炎、クローン病、肥満細胞症、高IgE症候群、全身性エリテマトーデス、乾癬、ざ瘡、多発性硬化症、同種異系移植片拒絶反応、再灌流損傷、慢性閉塞性肺疾患、チャーグ-ストラウス症候群、副鼻腔炎、好塩基球性白血病、慢性じんま疹、好塩基球性白血球増加症、乾癬、湿疹、COPD(慢性閉塞性肺障害)、関節炎、関節リュウマチ、乾癬性関節炎、骨関節炎及び心血管障害からなる群から選択される、請求項38〜42のいずれか1項記載の方法。
- 前記障害、疾患又は状態が、喘息、運動誘発喘息、アレルギー性鼻炎、アトピー性皮膚炎、慢性閉塞性肺疾患又はアレルギー結膜炎である、請求項43記載の方法。
- 前記化合物が、経口、非経口、又は局所投与される、請求項38〜44のいずれか1項記載の方法。
- 前記化合物が、第2の治療薬と併用投与される、請求項38〜45のいずれか1項記載の方法。
- CCR3レセプターを、請求項1〜32のいずれか1項記載の化合物又は請求項33〜37のいずれか1項記載の医薬組成物と接触させることを含む、CCR3活性の調節方法。
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ES2474615T3 (es) | 2009-04-22 | 2014-07-09 | Axikin Pharmaceuticals, Inc. | Antagonistas de CCR3 arilsulfonamidas 2,5-disustituidas |
EP2542542B1 (en) * | 2010-03-02 | 2015-04-22 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide ccr3 antagonists |
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