JP2016535097A5 - - Google Patents
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- Publication number
- JP2016535097A5 JP2016535097A5 JP2016551052A JP2016551052A JP2016535097A5 JP 2016535097 A5 JP2016535097 A5 JP 2016535097A5 JP 2016551052 A JP2016551052 A JP 2016551052A JP 2016551052 A JP2016551052 A JP 2016551052A JP 2016535097 A5 JP2016535097 A5 JP 2016535097A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- fluoro
- indol
- indole
- alkyl
- 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.)
- Pending
Links
- -1 carboxy, amino Chemical group 0.000 claims 50
- 229910052736 halogen Inorganic materials 0.000 claims 46
- 150000002367 halogens Chemical class 0.000 claims 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 43
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 125000004043 oxo group Chemical group O=* 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 239000011780 sodium chloride Substances 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 150000001336 alkenes Chemical class 0.000 claims 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 9
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N 2-Pyrrolidone Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N Azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N THP Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical group [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 229940113083 morpholine Drugs 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 2
- TXQAZWIBPGKHOX-UHFFFAOYSA-N 1H-indol-3-amine Chemical compound C1=CC=C2C(N)=CNC2=C1 TXQAZWIBPGKHOX-UHFFFAOYSA-N 0.000 claims 1
- ZXAZWXJOKVUXST-UHFFFAOYSA-N 3'-methyl-N-(3'-methylspiro[1,3-dithiolane-2,4'-6,7-dihydro-5H-1-benzofuran]-2'-carbonyl)-N-(2-morpholin-4-ylethyl)spiro[1,3-dithiolane-2,4'-6,7-dihydro-5H-1-benzofuran]-2'-carboxamide Chemical compound C1=2C(C)=C(C(=O)N(CCN3CCOCC3)C(=O)C3=C(C=4C5(SCCS5)CCCC=4O3)C)OC=2CCCC21SCCS2 ZXAZWXJOKVUXST-UHFFFAOYSA-N 0.000 claims 1
- YYFFEPUCAKVRJX-UHFFFAOYSA-N 6-fluoro-1H-indole Chemical compound FC1=CC=C2C=CNC2=C1 YYFFEPUCAKVRJX-UHFFFAOYSA-N 0.000 claims 1
- 206010001897 Alzheimer's disease Diseases 0.000 claims 1
- IIMSGVQGXKBDPG-UHFFFAOYSA-N CC(=O)N1CC(C1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 Chemical compound CC(=O)N1CC(C1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 IIMSGVQGXKBDPG-UHFFFAOYSA-N 0.000 claims 1
- GRXOMNRODRJLBJ-UHFFFAOYSA-N CN(C)C(=O)Cn1cc(cn1)-c1c[nH]c2cc(F)ccc12 Chemical compound CN(C)C(=O)Cn1cc(cn1)-c1c[nH]c2cc(F)ccc12 GRXOMNRODRJLBJ-UHFFFAOYSA-N 0.000 claims 1
- NAOSAFXZAVILCY-UHFFFAOYSA-N CNC(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 Chemical compound CNC(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 NAOSAFXZAVILCY-UHFFFAOYSA-N 0.000 claims 1
- SISYFCWHNNDGTN-UHFFFAOYSA-N COC1=CC=C(C=C1)N1N=CC(=C1)C1=CNC2=CC=CC=C12 Chemical compound COC1=CC=C(C=C1)N1N=CC(=C1)C1=CNC2=CC=CC=C12 SISYFCWHNNDGTN-UHFFFAOYSA-N 0.000 claims 1
- NUDIHFHPQOUZNB-UHFFFAOYSA-N COCC(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 Chemical compound COCC(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 NUDIHFHPQOUZNB-UHFFFAOYSA-N 0.000 claims 1
- NBPWFYAZPCFOSD-UHFFFAOYSA-N COCCS(=O)(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 Chemical compound COCCS(=O)(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 NBPWFYAZPCFOSD-UHFFFAOYSA-N 0.000 claims 1
- AEVFEIKEJIOXPZ-UHFFFAOYSA-N Fc1ccc2c(c[nH]c2c1)-c1cnn(CC2CNC2)c1 Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(CC2CNC2)c1 AEVFEIKEJIOXPZ-UHFFFAOYSA-N 0.000 claims 1
- MAGPDBMSRVAGBS-UHFFFAOYSA-N Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)-c1cccnc1 Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)-c1cccnc1 MAGPDBMSRVAGBS-UHFFFAOYSA-N 0.000 claims 1
- QYGLYXKNZBRWME-UHFFFAOYSA-N Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)-c1cccnn1 Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)-c1cccnn1 QYGLYXKNZBRWME-UHFFFAOYSA-N 0.000 claims 1
- RURXZTRISPSIKX-UHFFFAOYSA-N Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)C1CCN(CC1)C(=O)C=C Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)C1CCN(CC1)C(=O)C=C RURXZTRISPSIKX-UHFFFAOYSA-N 0.000 claims 1
- STCVAWGKRPLXNH-UHFFFAOYSA-N Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)C1CCNCC1 Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)C1CCNCC1 STCVAWGKRPLXNH-UHFFFAOYSA-N 0.000 claims 1
- 201000001971 Huntington's disease Diseases 0.000 claims 1
- 229940090034 Ibu Drugs 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- XMXGWSFXXJAABK-UHFFFAOYSA-N NC(=O)C(O)Cn1cc(cn1)-c1c[nH]c2cc(F)ccc12 Chemical compound NC(=O)C(O)Cn1cc(cn1)-c1c[nH]c2cc(F)ccc12 XMXGWSFXXJAABK-UHFFFAOYSA-N 0.000 claims 1
- LAESKFXZAPUKGC-FQEVSTJZSA-N N[C@H](C(=O)N1CCC(CC1)N1N=CC(=C1)C1=CNC2=CC(=CC=C12)F)C(C)C Chemical compound N[C@H](C(=O)N1CCC(CC1)N1N=CC(=C1)C1=CNC2=CC(=CC=C12)F)C(C)C LAESKFXZAPUKGC-FQEVSTJZSA-N 0.000 claims 1
- 206010053643 Neurodegenerative disease Diseases 0.000 claims 1
- TUGZIYDQIOFSDC-UHFFFAOYSA-N OCCN1CCC(Cn2cc(cn2)-c2c[nH]c3cc(F)ccc23)CC1 Chemical compound OCCN1CCC(Cn2cc(cn2)-c2c[nH]c3cc(F)ccc23)CC1 TUGZIYDQIOFSDC-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 101710019691 Olfr1 Proteins 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N Propanamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 claims 1
- 102100014437 TDO2 Human genes 0.000 claims 1
- 101710006302 TDO2 Proteins 0.000 claims 1
- 206010047461 Viral infection Diseases 0.000 claims 1
- 208000001756 Virus Disease Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000000240 adjuvant Effects 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 230000001684 chronic Effects 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000017613 viral reproduction Effects 0.000 claims 1
- 0 **(C=C1)=*=C1[n](c(N)c1-c2c[n]c3c2cc(*)c(I)c3)nc1N Chemical compound **(C=C1)=*=C1[n](c(N)c1-c2c[n]c3c2cc(*)c(I)c3)nc1N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13192224 | 2013-11-08 | ||
| EP13192224.7 | 2013-11-08 | ||
| US14/076,016 US9126984B2 (en) | 2013-11-08 | 2013-11-08 | 4-(indol-3-yl)-pyrazole derivatives, pharmaceutical compositions and methods for use |
| US14/076,016 | 2013-11-08 | ||
| BE2014/0845 | 2014-11-03 | ||
| BE201400845 | 2014-11-03 | ||
| PCT/EP2014/074099 WO2015067782A1 (en) | 2013-11-08 | 2014-11-07 | 4-(indol-3-yl)-pyrazole derivatives, pharmaceutical compositions and methods for use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016535097A JP2016535097A (ja) | 2016-11-10 |
| JP2016535097A5 true JP2016535097A5 (ru) | 2017-09-14 |
Family
ID=53040940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016551052A Pending JP2016535097A (ja) | 2013-11-08 | 2014-11-07 | ４−（インドール−３−イル）−ピラゾール誘導体、医薬組成物および使用のための方法 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP3066090A1 (ru) |
| JP (1) | JP2016535097A (ru) |
| CA (1) | CA2929650C (ru) |
| WO (1) | WO2015067782A1 (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI695831B (zh) | 2014-09-13 | 2020-06-11 | 香港商南北兄弟藥業投資有限公司 | Ｃｒｔｈ２拮抗劑化合物及其用途 |
| MX2018013235A (es) * | 2016-04-29 | 2019-02-13 | Bayer Pharma AG | Forma polimorfa de n-{6-(2-hidroxipropan-2-il)-2-[2-(metilsulfonil )etil]-2h-indazol-5-il}-6-(trifluorometil)piridin-2-carboxamida. |
| EP3269714A1 (en) | 2016-07-13 | 2018-01-17 | Netherlands Translational Research Center B.V. | Inhibitors of tryptophan 2,3-dioxygenase |
| WO2018054365A1 (en) | 2016-09-24 | 2018-03-29 | Beigene, Ltd. | NOVEL 5 or 8-SUBSTITUTED IMIDAZO [1, 5-a] PYRIDINES AS SELECTIVE INHIBITORS OF INDOLEAMINE AND/OR TRYPTOPHANE 2, 3-DIOXYGENASES |
| WO2023235809A1 (en) * | 2022-06-02 | 2023-12-07 | Eli Lilly And Company | Cgas inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2862647B1 (fr) * | 2003-11-25 | 2008-07-04 | Aventis Pharma Sa | Derives de pyrazolyle, procede de preparation et intermediaires de ce procede a titre de medicaments et de compositions pharmaceutiques les renfermant |
| GB0516156D0 (en) * | 2005-08-05 | 2005-09-14 | Eisai London Res Lab Ltd | JNK inhibitors |
| US20110159017A1 (en) | 2008-04-11 | 2011-06-30 | Ludwig Institute For Cancer Research Ltd. | Trytophan catabolism in cancer treatment and diagnosis |
| CA2772371A1 (en) | 2009-05-27 | 2010-12-02 | F. Hoffmann-La Roche Ag | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| WO2011045224A1 (de) | 2009-10-12 | 2011-04-21 | Bayer Cropscience Ag | 1- (pyrid-3-yl) -pyrazole und 1- (pyrimid-5-yl) -pyrazole als schädlingsbekämpfungsmittel |
| CA2803802A1 (en) * | 2010-06-23 | 2011-12-29 | Vertex Pharmaceuticals Incorporated | Pyrrolo- pyrazine derivatives useful as inhibitors of atr kinase |
-
2014
- 2014-11-07 EP EP14796082.7A patent/EP3066090A1/en not_active Withdrawn
- 2014-11-07 CA CA2929650A patent/CA2929650C/en not_active Expired - Fee Related
- 2014-11-07 JP JP2016551052A patent/JP2016535097A/ja active Pending
- 2014-11-07 WO PCT/EP2014/074099 patent/WO2015067782A1/en active Application Filing
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