CA2571421A1

CA2571421A1 - Compounds for immunopotentiation

Compounds for immunopotentiation Download PDF

Info

Publication number: CA2571421A1
Authority: CA; Canada
Prior art keywords: alkyl; antigens; compound; aryl; heterocyclyl
Prior art date: 2004-06-24
Legal status : Abandoned

Application number

CA002571421A

Other languages

English (en)

French (fr)

Inventor

Nicholas Valiante

Feng Xu

Joel B. Silver

Current Assignee

Novartis Vaccines and Diagnostics Inc

Original Assignee

Individual

Priority date

2004-06-24

Filing date

2005-06-24

Publication date

2006-01-05

2005-06-24 Application filed by Individual filed Critical Individual

2006-01-05 Publication of CA2571421A1 publication Critical patent/CA2571421A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 212
230000002434 immunopotentiative effect Effects 0.000 title description 9
238000000034 method Methods 0.000 claims abstract description 146
230000028993 immune response Effects 0.000 claims abstract description 61
-1 -aryl(R)p Chemical group 0.000 claims description 216
125000000217 alkyl group Chemical group 0.000 claims description 177
206010028980 Neoplasm Diseases 0.000 claims description 108
239000003814 drug Substances 0.000 claims description 104
125000000623 heterocyclic group Chemical group 0.000 claims description 89
125000003118 aryl group Chemical group 0.000 claims description 88
201000011510 cancer Diseases 0.000 claims description 84
238000011282 treatment Methods 0.000 claims description 81
229940079593 drug Drugs 0.000 claims description 79
239000003795 chemical substances by application Substances 0.000 claims description 78
125000003545 alkoxy group Chemical group 0.000 claims description 69
229910052736 halogen Inorganic materials 0.000 claims description 43
102000004127 Cytokines Human genes 0.000 claims description 41
108090000695 Cytokines Proteins 0.000 claims description 41
150000002367 halogens Chemical class 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
206010020751 Hypersensitivity Diseases 0.000 claims description 36
230000007815 allergy Effects 0.000 claims description 35
208000036142 Viral infection Diseases 0.000 claims description 24
208000006673 asthma Diseases 0.000 claims description 24
230000009385 viral infection Effects 0.000 claims description 24
210000004369 blood Anatomy 0.000 claims description 23
239000008280 blood Substances 0.000 claims description 23
208000023275 Autoimmune disease Diseases 0.000 claims description 22
230000001965 increasing effect Effects 0.000 claims description 21
230000001939 inductive effect Effects 0.000 claims description 21
238000004519 manufacturing process Methods 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
206010070308 Refractory cancer Diseases 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 10
208000016691 refractory malignant neoplasm Diseases 0.000 claims description 10
102000019034 Chemokines Human genes 0.000 claims description 9
108010012236 Chemokines Proteins 0.000 claims description 9
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239000003102 growth factor Substances 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 3
125000005059 halophenyl group Chemical group 0.000 claims 1
239000002777 nucleoside Chemical class 0.000 abstract description 30
150000003833 nucleoside derivatives Chemical class 0.000 abstract description 28
DQYBRTASHMYDJG-UHFFFAOYSA-N Bisindolylmaleimide Chemical class C1=CC=C2C(C=3C(=O)NC(C=3C=3C4=CC=CC=C4NC=3)=O)=CNC2=C1 DQYBRTASHMYDJG-UHFFFAOYSA-N 0.000 abstract description 22
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 abstract description 20
150000004892 pyridazines Chemical class 0.000 abstract description 19
150000003384 small molecules Chemical class 0.000 abstract description 19
239000005551 L01XE03 - Erlotinib Substances 0.000 abstract description 18
AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 abstract description 18
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UXXQOJXBIDBUAC-UHFFFAOYSA-N tandutinib Chemical compound COC1=CC2=C(N3CCN(CC3)C(=O)NC=3C=CC(OC(C)C)=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 UXXQOJXBIDBUAC-UHFFFAOYSA-N 0.000 abstract description 18
UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 abstract description 18
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XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 abstract description 17
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BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 abstract description 17
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HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical class C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 abstract description 16
150000004777 chromones Chemical class 0.000 abstract description 12
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125000005843 halogen group Chemical group 0.000 description 24
125000001424 substituent group Chemical group 0.000 description 24
150000001720 carbohydrates Chemical class 0.000 description 23
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108060008682 Tumor Necrosis Factor Proteins 0.000 description 22
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125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
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NHFDRBXTEDBWCZ-ZROIWOOFSA-N 3-[2,4-dimethyl-5-[(z)-(2-oxo-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=CC=C3NC\2=O)=C1C NHFDRBXTEDBWCZ-ZROIWOOFSA-N 0.000 description 20
241000725303 Human immunodeficiency virus Species 0.000 description 20
208000035473 Communicable disease Diseases 0.000 description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
125000003282 alkyl amino group Chemical group 0.000 description 18
230000001225 therapeutic effect Effects 0.000 description 18
AXRCEOKUDYDWLF-UHFFFAOYSA-N 3-(1-methyl-3-indolyl)-4-[1-[1-(2-pyridinylmethyl)-4-piperidinyl]-3-indolyl]pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=CC=C11)=CN1C(CC1)CCN1CC1=CC=CC=N1 AXRCEOKUDYDWLF-UHFFFAOYSA-N 0.000 description 17
AKJHMTWEGVYYSE-AIRMAKDCSA-N 4-HPR Chemical compound C=1C=C(O)C=CC=1NC(=O)/C=C(\C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C AKJHMTWEGVYYSE-AIRMAKDCSA-N 0.000 description 17
PLHJCIYEEKOWNM-UHFFFAOYSA-N 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one Chemical compound CN1C=NC=C1C(N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 PLHJCIYEEKOWNM-UHFFFAOYSA-N 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
UIARLYUEJFELEN-LROUJFHJSA-N LSM-1231 Chemical compound C12=C3N4C5=CC=CC=C5C3=C3C(=O)NCC3=C2C2=CC=CC=C2N1[C@]1(C)[C@](CO)(O)C[C@H]4O1 UIARLYUEJFELEN-LROUJFHJSA-N 0.000 description 17
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 17
BIIVYFLTOXDAOV-YVEFUNNKSA-N alvocidib Chemical compound O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O BIIVYFLTOXDAOV-YVEFUNNKSA-N 0.000 description 17
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DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 17
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