HRP20100153T1 - Antagonisti kemokin receptora - Google Patents
Antagonisti kemokin receptora Download PDFInfo
- Publication number
- HRP20100153T1 HRP20100153T1 HR20100153T HRP20100153T HRP20100153T1 HR P20100153 T1 HRP20100153 T1 HR P20100153T1 HR 20100153 T HR20100153 T HR 20100153T HR P20100153 T HRP20100153 T HR P20100153T HR P20100153 T1 HRP20100153 T1 HR P20100153T1
- Authority
- HR
- Croatia
- Prior art keywords
- piperidin
- indole
- amide
- carboxylic acid
- ethyl
- Prior art date
Links
- 229940122444 Chemokine receptor antagonist Drugs 0.000 title 1
- 239000002559 chemokine receptor antagonist Substances 0.000 title 1
- -1 C2-C7 alkenoxy Chemical group 0.000 claims abstract 46
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 28
- 125000001424 substituent group Chemical group 0.000 claims abstract 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 24
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract 22
- 150000002367 halogens Chemical class 0.000 claims abstract 22
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 20
- 125000003118 aryl group Chemical group 0.000 claims abstract 19
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract 15
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 14
- 150000002825 nitriles Chemical class 0.000 claims abstract 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 9
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000004429 atom Chemical group 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims 5
- DHBXOVOJDHOGPK-UHFFFAOYSA-N 4-(cyclobutylmethoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OCC1CCC1 DHBXOVOJDHOGPK-UHFFFAOYSA-N 0.000 claims 4
- MGYKIRMKEXMQOH-UHFFFAOYSA-N 4-(2-methylpropoxy)-1h-indole-2-carboxylic acid Chemical compound CC(C)COC1=CC=CC2=C1C=C(C(O)=O)N2 MGYKIRMKEXMQOH-UHFFFAOYSA-N 0.000 claims 3
- RUVKKSCYIJINOW-UHFFFAOYSA-N 4-(furan-3-ylmethoxy)-1h-indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1OCC=1C=COC=1 RUVKKSCYIJINOW-UHFFFAOYSA-N 0.000 claims 3
- 208000030507 AIDS Diseases 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 3
- CTXFGYQKBGANME-AAEUAGOBSA-N (3s,4s)-1-[2-(4-aminopiperidin-1-yl)ethyl]-3-methylpiperidin-4-ol Chemical compound C1C[C@H](O)[C@@H](C)CN1CCN1CCC(N)CC1 CTXFGYQKBGANME-AAEUAGOBSA-N 0.000 claims 2
- NNIUGPNBOPJSQX-NSHDSACASA-N 1-[(2s)-1-(4-aminopiperidin-1-yl)propan-2-yl]piperidin-4-ol Chemical compound C([C@H](C)N1CCC(O)CC1)N1CCC(N)CC1 NNIUGPNBOPJSQX-NSHDSACASA-N 0.000 claims 2
- QCHULMRAPOGNRQ-UHFFFAOYSA-N 4-(3-fluorophenoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OC1=CC=CC(F)=C1 QCHULMRAPOGNRQ-UHFFFAOYSA-N 0.000 claims 2
- BLLFPHHQELRWKO-UHFFFAOYSA-N 4-(4-fluorophenoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OC1=CC=C(F)C=C1 BLLFPHHQELRWKO-UHFFFAOYSA-N 0.000 claims 2
- IZBJQRJUYUATNZ-UHFFFAOYSA-N 4-[(4,6-difluoro-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound FC1=CC(F)=C2C(COC3=C4C=C(NC4=CC=C3)C(=O)O)=COC2=C1 IZBJQRJUYUATNZ-UHFFFAOYSA-N 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- FJFTUVLATJEADG-OBJOEFQTSA-N (3s,4s)-1-[(2s)-1-(4-aminopiperidin-1-yl)propan-2-yl]-3-methylpiperidin-4-ol Chemical compound C([C@H](C)N1C[C@H](C)[C@@H](O)CC1)N1CCC(N)CC1 FJFTUVLATJEADG-OBJOEFQTSA-N 0.000 claims 1
- PBNYMYSMBHJXDB-UHFFFAOYSA-N 1-[2-(4-aminophenyl)ethyl]piperidin-4-ol N-[1-[2-(azepan-1-yl)ethyl]piperidin-4-yl]-4-phenyl-1H-indole-2-carboxamide 4-[4-(trifluoromethyl)phenyl]-1H-indole-2-carboxylic acid Chemical compound NC1=CC=C(CCN(CC2)CCC2O)C=C1.OC(C(NC1=CC=C2)=CC1=C2C1=CC=C(C(F)(F)F)C=C1)=O.O=C(C(NC1=CC=C2)=CC1=C2C1=CC=CC=C1)NC1CCN(CCN2CCCCCC2)CC1 PBNYMYSMBHJXDB-UHFFFAOYSA-N 0.000 claims 1
- KKMVGFXOQKVBAA-XITMACKWSA-N 1-[[(1S,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methyl]piperidin-4-amine dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1C[C@H]1[C@H]2CCCCN2CCC1 KKMVGFXOQKVBAA-XITMACKWSA-N 0.000 claims 1
- NVBRPWXIBLHDQY-UHFFFAOYSA-N 4-(3-methylbutan-2-yloxy)-1h-indole-2-carboxylic acid Chemical compound CC(C)C(C)OC1=CC=CC2=C1C=C(C(O)=O)N2 NVBRPWXIBLHDQY-UHFFFAOYSA-N 0.000 claims 1
- IDCLFENUIDJACO-UHFFFAOYSA-N 4-(3-methylphenoxy)-1h-indole-2-carboxylic acid Chemical compound CC1=CC=CC(OC=2C=3C=C(NC=3C=CC=2)C(O)=O)=C1 IDCLFENUIDJACO-UHFFFAOYSA-N 0.000 claims 1
- XXIRXGQNEUCGCN-UHFFFAOYSA-N 4-(4-ethoxyphenyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 XXIRXGQNEUCGCN-UHFFFAOYSA-N 0.000 claims 1
- ATJSZTHEQAEHLH-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 ATJSZTHEQAEHLH-UHFFFAOYSA-N 0.000 claims 1
- IPCITYBUXQLBOZ-UHFFFAOYSA-N 4-(4-methylphenoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1OC1=CC=CC2=C1C=C(C(O)=O)N2 IPCITYBUXQLBOZ-UHFFFAOYSA-N 0.000 claims 1
- SKUYHVYEULCXMI-UHFFFAOYSA-N 4-(4-methylphenyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 SKUYHVYEULCXMI-UHFFFAOYSA-N 0.000 claims 1
- SCQLSAFCJKMTTA-NRFANRHFSA-N 4-[(4,6-dimethoxy-1-benzofuran-3-yl)methoxy]-n-[1-[(2s)-2-(4-hydroxypiperidin-1-yl)propyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound N1([C@@H](C)CN2CCC(CC2)NC(=O)C=2NC=3C=CC=C(C=3C=2)OCC=2C3=C(OC)C=C(C=C3OC=2)OC)CCC(O)CC1 SCQLSAFCJKMTTA-NRFANRHFSA-N 0.000 claims 1
- CFSCUBAMBADXME-SYZUXVNWSA-N 4-[(4,6-dimethoxy-1-benzofuran-3-yl)methoxy]-n-[1-[(2s)-2-[(3s,4s)-4-hydroxy-3-methylpiperidin-1-yl]propyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound N1([C@@H](C)CN2CCC(CC2)NC(=O)C=2NC=3C=CC=C(C=3C=2)OCC=2C3=C(OC)C=C(C=C3OC=2)OC)CC[C@H](O)[C@@H](C)C1 CFSCUBAMBADXME-SYZUXVNWSA-N 0.000 claims 1
- BPVVVEHBKAJIAJ-UHFFFAOYSA-N 4-[(5,6-dimethyl-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C1=2C=C(C)C(C)=CC=2OC=C1COC1=CC=CC2=C1C=C(C(O)=O)N2 BPVVVEHBKAJIAJ-UHFFFAOYSA-N 0.000 claims 1
- DJKNDDHJSBVDIA-IFUPQEAVSA-N 4-[(5,6-dimethyl-1-benzofuran-3-yl)methoxy]-n-[1-[(2s)-2-(4-hydroxypiperidin-1-yl)propyl]piperidin-4-yl]-1h-indole-2-carboxamide;dihydrochloride Chemical compound Cl.Cl.N1([C@H](CN2CCC(CC2)NC(=O)C=2NC3=CC=CC(OCC=4C5=CC(C)=C(C)C=C5OC=4)=C3C=2)C)CCC(O)CC1 DJKNDDHJSBVDIA-IFUPQEAVSA-N 0.000 claims 1
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- KCDNTDCHRUFYIZ-UHFFFAOYSA-N 4-[(5-chloro-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C1=C(Cl)C=C2C(COC3=C4C=C(NC4=CC=C3)C(=O)O)=COC2=C1 KCDNTDCHRUFYIZ-UHFFFAOYSA-N 0.000 claims 1
- XSAJSTMXDPQZLO-UHFFFAOYSA-N 4-[(5-fluoro-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C1=C(F)C=C2C(COC3=C4C=C(NC4=CC=C3)C(=O)O)=COC2=C1 XSAJSTMXDPQZLO-UHFFFAOYSA-N 0.000 claims 1
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- PXCMIJHGMVYIAN-YVQUGPBKSA-N n-[1-[[(1s,9ar)-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-yl]methyl]piperidin-4-yl]-4-[(4,6-difluoro-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CCN2CCCC[C@@H]2[C@@H]1CN(CC1)CCC1NC(=O)C(N1)=CC2=C1C=CC=C2OCC1=COC2=CC(F)=CC(F)=C21 PXCMIJHGMVYIAN-YVQUGPBKSA-N 0.000 claims 1
- GLIPOZLWHASUIN-OHKLCMIMSA-N n-[1-[[(1s,9ar)-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-yl]methyl]piperidin-4-yl]-4-[(7-fluoro-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CCN2CCCC[C@@H]2[C@@H]1CN(CC1)CCC1NC(=O)C(N1)=CC2=C1C=CC=C2OCC1=COC2=C1C=CC=C2F GLIPOZLWHASUIN-OHKLCMIMSA-N 0.000 claims 1
- ZNYXYGQGAJFGDQ-CUPDENHQSA-N n-[1-[[(1s,9ar)-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-yl]methyl]piperidin-4-yl]-4-[(7-methoxy-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CCN2CCCC[C@@H]2[C@@H]1CN(CC1)CCC1NC(=O)C(N1)=CC2=C1C=CC=C2OCC1=COC2=C1C=CC=C2OC ZNYXYGQGAJFGDQ-CUPDENHQSA-N 0.000 claims 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims 1
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000002451 tumor necrosis factor inhibitor Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
Classifications
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- Hospice & Palliative Care (AREA)
Abstract
Spoj, naznačen time, da je formule (I) ili njegova farmaceutski prihvatljiva sol ili njegov ester: gdje: Z je CR1R2, NR3, O ili S; R je izabran iz skupine koju čine hidroksi, po izboru supstituirana C1-C7 alkoksi, C2-C7 alkenoksi, cikloalkiloksi, ariloksi, heteroariloksi, aril-C1-C7 alkoksi ili heteroaril-C1-C7 alkoksi, po izboru supstituirana C1-C7 alkil ili C2-C7 alkenil, po izboru supstituirana aril, heteroaril ili po izboru supstituirana aril-C1-C7 alkil skupina; R9 predstavlja jedan ili više prstenastih supstituenada izabranih iz skupine koju čine H, hidroksi, po izboru supstituirana C1-C7 alkoksi, C2-C7 alkenoksi, cikloalkiloksi, ariloksi, heteroariloksi, aril-C1-C7 alkoksi ili heteroaril-C1-C7 alkoksi, po izboru supstituirana C1-C7 alkil ili C2-C7 alkenil, po izboru supstituirana aril, heteroaril ili po izboru supstituirana aril-C1-C7 alkil skupina; R1, R2 i R3 su neovisno izabrani iz skupine koju čine H i C1-C7 alkil; X je C3-C18 cikloalkil, heterocikloalkil, aril ili heteroaril od kojih svaki može biti po izboru supstituiran; Q je poveznica od između 1 do 3 atoma u duljinu; Y je C3-C18 cikloalkil, heterocikloalkil, premošteni cikloalkil, premošteni heterocikloalkil, aril, heteroaril, spojeni aril-heterocikloalkil, od kojih su svi neovisno supstituirani po izboru jedanput ili više; izborni supstituend ili supstituendi na R i R9 su neovisno izabrani iz skupine koju čine halogen, hidroksi, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; od kojih su svi, izuzev halogena, neovisno po izboru supstituirani s jednim ili više supstituenada izabranih iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; izborni supstituend ili supstituendi na X su neovisno izabrani iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; od kojih su svi, izuzev halogena, neovisno po izboru supstituirani s jednim ili više supstituenada izabranih iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-niži alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; izborni supstituend ili supstituendi na Y su neovisno izabrani iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18
Claims (10)
1. Spoj, naznačen time, da je formule (I) ili njegova farmaceutski prihvatljiva sol ili njegov ester:
[image]
gdje:
Z je CR1R2, NR3, O ili S;
R je izabran iz skupine koju čine hidroksi, po izboru supstituirana C1-C7 alkoksi, C2-C7 alkenoksi, cikloalkiloksi, ariloksi, heteroariloksi, aril-C1-C7 alkoksi ili heteroaril-C1-C7 alkoksi, po izboru supstituirana C1-C7 alkil ili C2-C7 alkenil, po izboru supstituirana aril, heteroaril ili po izboru supstituirana aril-C1-C7 alkil skupina;
R9 predstavlja jedan ili više prstenastih supstituenada izabranih iz skupine koju čine H, hidroksi, po izboru supstituirana C1-C7 alkoksi, C2-C7 alkenoksi, cikloalkiloksi, ariloksi, heteroariloksi, aril-C1-C7 alkoksi ili heteroaril-C1-C7 alkoksi, po izboru supstituirana C1-C7 alkil ili C2-C7 alkenil, po izboru supstituirana aril, heteroaril ili po izboru supstituirana aril-C1-C7 alkil skupina;
R1, R2 i R3 su neovisno izabrani iz skupine koju čine H i C1-C7 alkil;
X je C3-C18 cikloalkil, heterocikloalkil, aril ili heteroaril od kojih svaki može biti po izboru supstituiran;
Q je poveznica od između 1 do 3 atoma u duljinu;
Y je C3-C18 cikloalkil, heterocikloalkil, premošteni cikloalkil, premošteni heterocikloalkil, aril, heteroaril, spojeni aril-heterocikloalkil, od kojih su svi neovisno supstituirani po izboru jedanput ili više;
izborni supstituend ili supstituendi na R i R9 su neovisno izabrani iz skupine koju čine halogen, hidroksi, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; od kojih su svi, izuzev halogena, neovisno po izboru supstituirani s jednim ili više supstituenada izabranih iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril;
izborni supstituend ili supstituendi na X su neovisno izabrani iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; od kojih su svi, izuzev halogena, neovisno po izboru supstituirani s jednim ili više supstituenada izabranih iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-niži alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril;
izborni supstituend ili supstituendi na Y su neovisno izabrani iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; od kojih su svi, izuzev halogena, neovisno po izboru supstituirani s jednim ili više supstituenada izabranih iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C2-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril.
2. Spoj, naznačen time, da je formule (II) ili njegova farmaceutski prihvatljiva sol ili njegov ester:
[image]
gdje:
Z' je NH, NCH3, CH2, S ili O;
R' je hidroksi, po izboru supstituirana C1-C7 alkoksi, C2-C7 alkeniloksi, cikloalkil-C1-C7 alkiloksi, ariloksi, heteroariloksi, heteroaril-C1-C7 alkiloksi ili aril-C1-C7 alkiloksi, po izboru supstituirana aril, heteroaril ili po izboru supstituirana aril-C1-C7 alkil skupina;
X' je izabran iz skupine koju čine:
[image]
Q' je izabran iz skupine koju čine: -CH2-, -CH2-CH2-, -CH2-CH2-CH2-, -CH(CH3)-CH2-, -CH2-CH(CH3)-, -CH2-NH-, -CH(CH3)-NH-, -CH2-N(CH3)-, -CH2-CH(CH2OH)- ili –CH(CH3)-NH(CH3)-;
Y' je izabran iz skupine koju čine: C3-C18 cikloalkil, heterocikloalkil, premošteni cikloalkil, premošteni heterocikloalkil, aril, heteroaril, spojeni aril-heterocikloalkil, od kojih su svi neovisno po izboru supstituirani jedanput ili više;
izborni supstituend ili supstituendi na R' su neovisno izabrani iz skupine koju čine halogen, hidroksi, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; od kojih su svi, izuzev halogena, neovisno po izboru supstituirani s jednim ili više supstituenada izabranih iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-niži alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril;
izborni supstituend ili supstituendi na Y' su neovisno izabrani iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril; od kojih su svi, izuzev halogena, neovisno po izboru supstituirani s jednim ili više supstituenada izabranih iz skupine koju čine halogen, hidroksil, C1-C7 alkil, mono ili di-C1-C7 alkilamino, aminokarbonil, mono ili di-C1-C7 alkilaminokarbonil, amino, karboksi, C1-C7 alkoksi, C3-C12 cikloalkil, C3-C18 heterocikloalkil, C1-C7 alkilkarbonil, C1-C7 alkoksikarbonil, nitril, aril.
3. Spoj u skladu s bilo kojim od prethodnih zahtjeva, naznačen time, da je izabran iz slijedeće skupine:
4-metoksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-izopropoksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-izopropoksi-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-ciklopropilmetoksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-ciklopropilmetoksi-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-ciklopropilmetoksi-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-ciklopropilmetoksi-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline [1-(2-piperidin-1-il-etil)-piperidin-4-il]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-(RS)-2-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-(4-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-((2S, 6R)-2,8-dimetil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-((R)-3-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-((S)-3-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-((1R, 3S, 5S)-3-hidroksi-8-aza-biciklo[3.2.1]okt-8-il)-etil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline [4-(2-azepan-1-il-etil)-fenil]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline (4-{[metil-(tetrahidro-piran-4-il)-amino]-metil}-cikloheksil)-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline (4-{[metil-(tetrahidro-piran-4-il)-amino]-metil}-fenil)-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline (4-{(R)-1-[metil-(tetrahidro-piran-4-il)-amino]-etil}-fenil)-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[2-(3-(R)-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[2-((1R, 3S, 5S)-3-aza-biciklo[3.2.1]okt-8-il)-etil]-piperidin-4-il}-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(3-metil-butiloksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-ciklopentilmetoksi-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(1,2-dimetil-propoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(2,2-dimetil-propoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(4-metil-pentiloksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(3,3-dimetil-butoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(furan-2-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-benziloksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(4-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(4-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(6-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(6-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(6-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(6-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(6-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(5-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid
4-(5-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(5-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3R, 4R, 5S)-4-hidroksi-3,5-dimetil-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(5-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(5-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(7-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(4,6-difluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(4,6-difluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(4,6-difluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(4,6-difluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(4,6-difluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(7-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(6-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(6-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(6-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(6-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(4-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(4-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(4-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3R, 4R, 5S)-4-hidroksi-3,5-dimetil-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(4-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(7-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(7-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(2-piperidin-1-il-etil)-piperidin-4-il]-amid
4-(7-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(7-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(7-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(7-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(6-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid
4-(6-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(6-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(6-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(6-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(6-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(5-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(5-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il]-amid
4-(4-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid
4-(4-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(4-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(4-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(4-metoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(4,6-dimetoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(4,6-dimetoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(4,6-dimetoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(4,6-dimetoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(4,6-dimetoksi-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(5,6-dimetil-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid dihidroklorid
4-(5,6-dimetil-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(5,6-dimetil-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid dihidroklorid
4-(5,6-dimetil-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(5,6-dimetil-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid dihidroklorid
4-(4-etoksi-fenil)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(4-metoksi-fenil)-1H-indol-2-karboksilne kiseline {1-[(S)-2-(4-hidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-fenoksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-m-toliloksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-m-toliloksi-1H-indol-2-karboksilne kiseline {1-[2-(3-(RS)-hidroksi-piperidin-1-il)-etil]-piperidin-4-il]-amid
4-m-toliloksi-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il]-amid
4-p-toliloksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-p-toliloksi-1H-indol-2-karboksilne kiseline {1-[2-(3-(RS)-hidroksi-piperidin-1-il)-etil]-piperidin-4-il]-amid
4-p-toliloksi-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il]-amid
4-(3-fluoro-fenoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(3-fluoro-fenoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il]-amid
4-(4-fluoro-fenoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(4-fluoro-fenoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il]-amid
4-(3,4-difluoro-fenoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(3,5-difluoro-fenoksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(3,5-difluoro-fenoksi)-1H-indol-2-karboksilne kiseline {1-[2-(3-RS-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(3,5-difluoro-fenoksi)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(6-kloro-piridin-2-iloksi)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline [1-(oktahidro-kinolizin-1-ilmetil)-piperidin-4-il]-amid dihidroklorid
4-izobutoksi-1H-indol-2-karboksilne kiseline [1-(1-metil-piperidin-3-ilmetil)-piperidin-4-il]-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3R, 4R)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4R, 5S)-3,4-dihidroksi-5-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-ciklobutilmetoksi-1H-indol-2-karboksilne kiseline {1-[(R)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3R, 4R)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(2-metil-tiazol-4-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(oktahidro-kinolizin-1-ilmetil)-piperidin-4-il]-amid
4-(benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[2-(3,4-dihidroksi-5-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(5-fluoro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3RS, 4SR)-3,4-dihidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3RS, 4SR)-3,4-dihidroksi-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(9S, 9aS)-1-(oktahidro-pirido[2,1-c][1,4]-oksazin-9-il)-metil]-piperidin-4-il}-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {1-[(8S, 8aS)-1-(heksahidro-pirolo[2,1-c][1,4]-oksazin-8-il)-metil]-piperidin-4-il}-amid
4-(4-metoksi-fenil)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid
4-(4-etoksi-fenil)-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid
4-(6-metoksi-piridin-3-il)-1H-indol-2-karboksilne kiseline {1-[(S)-2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-propil]-piperidin-4-il}-amid
4-(6-metoksi-piridin-3-il)-1H-indol-2-karboksilne kiseline {1-[2-((3S, 4S)-4-hidroksi-3-metil-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-p-toliloksi-1H-indol-2-karboksilne kiseline {1-[(1S, 9aR)-1-(oktahidro-kinolizin-1-il)-metil]-piperidin-4-il}-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-1S-metil-etil)-piperidin-4-il]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-1R-metil-etil)-piperidin-4-il]-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(2S-azepan-1-il-propil)-piperidin-4-il]-amid
4-(furan-3-ilmetoksi)-1H-indol-2-karboksilne kiseline [1-(2R-azepan-1-il-propil)-piperidin-4-il]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-(3,6-dihidro-2H-piridin-1-il)-etil]-piperidin-4-il]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-azepan-1-il)-etil]-piperidin-4-il]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-(3-amino-azepan-1-il)-etil]-piperidin-4-il]-amid
4-izobutoksi-1H-indol-2-karboksilne kiseline {1-[2-(3-fluoro-piperidin-1-il)-etil]-piperidin-4-il]-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline [4-(2-piperidin-1-il-etil)-fenil]-amid
4-(5-kloro-benzofuran-3-ilmetoksi)-1H-indol-2-karboksilne kiseline {4-[2-(4-hidroksi-piperidin-1-il)-etil]-fenil}-amid
4-fenil-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(4-trifluorometil-fenil)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-p-tolil-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-1-il]-amid
4-(4-dimetilamino-fenil)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-benzo[1,2,5]oksadiazol-5-il-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(4-metoksi-fenil)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(3-cijano-fenil)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(4-etoksi-fenil)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-[3-(3-metoksi-propoksi)-fenil]-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(4-trifluorometoksi-fenil)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(2,4-dimetoksi-fenil)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(3,4-dimetoksi-fenil)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-benzo[1,3]dioksol-5-il-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-piridin-4-il-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(6-metoksi-piridin-3-il)-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-(4-etoksi-fenil)-1H-indol-2-karboksilne kiseline [1-(2-piperidin-1-il-etil)-piperidin-4-il]-amid
4-(4-metoksi-fenil)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(4-etoksi-fenil)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(6-metoksi-piridin-3-il)-1H-indol-2-karboksilne kiseline {1-[2-(4-hidroksi-piperidin-1-il)-etil]-piperidin-4-il}-amid
4-(4-metoksi-fenil)-1H-indol-2-karboksilne kiseline {1-[2-(3-hidroksi-8-aza-biciklo[3.2.1]okt-8-il)-etil]-piperidin-4-il}-amid
4-(6-metoksi-piridin-3-il)-1H-indol-2-karboksilne kiseline {1-[2-(3-hidroksi-8-aza-biciklo[3.2.1]okt-8-il)-etil]-piperidin-4-il}-amid
4-hidroksi-1H-indol-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-metoksi-benzo[b]tiofen-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-izobutoksi-benzo[b]tiofen-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid
4-izobutoksi-benzo[b]tiofen-2-karboksilne kiseline [1-(2-piperidin-1-il-etil)-piperidin-4-il]-amid
4-metoksi-benzofuran-2-karboksilne kiseline [1-(2-azepan-1-il-etil)-piperidin-4-il]-amid.
4. Spoj u skladu s bilo kojim od prethodnih zahtjeva, naznačen time, da je za uporabu kao farmaceutik za prevenciju, poboljšanje ili liječenje autoimunog ili upalnog oboljenja ili stanja.
5. Spoj u skladu s bilo kojim od zahtjeva 1 do 3, naznačen time, da je za uporabu kao farmaceutik za prevenciju, poboljšanje ili liječenje HIV infekcije ili AIDS-a.
6. Postupak priprave spoja formule (I), naznačen time, da obuhvaća:
(a) reakciju spoja formule (III)
[image]
gdje R'' je H ili niža alkil skupina, sa spojem formule NH2-X-Q-Y, pri čemu su skupine R, R9, Z, X, Q i Y iste kao što su određene u zahtjevu 1; ili
(b) za pripravu spojeva formule (I) gdje X je piperidin-4-il i Q je –CH2-CH2- te Y je skupina formule –NR7R8 gdje N, R7 i R8 su povezani tako da zajednički određuju heterocikloalkil, premošteni cikloalkil, premošteni heterocikloalkil, heteroaril ili spojeni aril-heterocikloalkil, reakciju spoja formule (IV)
[image]
sa spojem formule NHR7R8 gdje su R7 i R8 isti kao gore određeni te R, R9 i Z su isti kao ranije određeni; ili
(c) za pripravu spojeva formule (I) gdje X je piperidin-4-il i Q je CH2-, reakciju spoja formule (V):
[image]
gdje su R, R9 i Z isti kao gore određeni, sa spojem formule HO-CH2-Y gdje je Y isti kao ranije određen; ili
(d) za pripravu spojeva formule (I) gdje R je po izboru supstituirana aril skupina, odgovarajuće supstituiranje Br skupine u spoju formule (VI) za navedenu supstituiranu aril skupinu:
[image]
gdje su Z, R9, X, Q i Y isti kao ranije određeni;
te dobivanje rezultirajućih spojeva formule (I) u slobodnom obliku ili u obliku soli.
7. Farmaceutski pripravak, naznačen time, da sadrži spoj u skladu sa zahtjevom 1 zajedno s farmaceutski prihvatljivim sredstvom za razrijeđivanje ili podlogom.
8. Uporaba spoja u skladu sa zahtjevom 1, naznačena time, da se koristi u proizvodnji lijeka za uporabu u liječenju autoimunog ili upalnog oboljenja ili stanja.
9. Uporaba spoja u skladu sa zahtjevom 1, naznačena time, da se koristi u proizvodnji lijeka za uporabu u liječenju HIV infekcije ili AIDS-a.
10. Uporaba spoja u skladu sa zahtjevom 1, naznačena time, da se koristi u kombinaciji s jednim ili više sredstava izabranih iz skupine koju čine: metotreksat, anti-TNF sredstvo, anti-IL-1 sredstvo, nukleozidni ili ne-nukleozidni inhibitor reverzne transkriptaze, inhibitor HIV proteaze, inhibitor fuzije ili anti-retrovirusno sredstvo, za proizvodnju lijeka za liječenje upalnog ili autoimunog oboljenja ili stanja ili HIV-a ili AIDS-a.
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GBGB0403038.3A GB0403038D0 (en) | 2004-02-11 | 2004-02-11 | Organic compounds |
PCT/EP2005/001362 WO2005077932A2 (en) | 2004-02-11 | 2005-02-10 | Chemokine receptor antagonists |
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