ES2669208T3 - Derivados de pirrolidinilsulfona y su uso como moduladores de ROR gamma - Google Patents
Derivados de pirrolidinilsulfona y su uso como moduladores de ROR gamma Download PDFInfo
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- ES2669208T3 ES2669208T3 ES15700613.1T ES15700613T ES2669208T3 ES 2669208 T3 ES2669208 T3 ES 2669208T3 ES 15700613 T ES15700613 T ES 15700613T ES 2669208 T3 ES2669208 T3 ES 2669208T3
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- cr2er2f
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- HMSYOMRFLOKYEK-UHFFFAOYSA-N 1-pyrrolidin-1-ylsulfonylpyrrolidine Chemical class C1CCCN1S(=O)(=O)N1CCCC1 HMSYOMRFLOKYEK-UHFFFAOYSA-N 0.000 title description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 91
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 74
- 239000001257 hydrogen Substances 0.000 claims abstract description 74
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 55
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 55
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 55
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 43
- 125000005843 halogen group Chemical group 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- -1 SO2R2c Chemical group 0.000 claims abstract description 9
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims abstract description 8
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 10
- 208000023275 Autoimmune disease Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
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- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
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- 208000030090 Acute Disease Diseases 0.000 claims 1
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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 102000013691 Interleukin-17 Human genes 0.000 description 11
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- 102000004127 Cytokines Human genes 0.000 description 1
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- 230000003042 antagnostic effect Effects 0.000 description 1
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- 125000004069 aziridinyl group Chemical group 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 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 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
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- 210000002443 helper t lymphocyte Anatomy 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 1
- 229960002751 imiquimod Drugs 0.000 description 1
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- 210000003734 kidney Anatomy 0.000 description 1
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
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- 230000003472 neutralizing effect Effects 0.000 description 1
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- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
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Classifications
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- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
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- C07D493/04—Ortho-condensed systems
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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
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- Hematology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| PCT/US2015/010089 WO2015103509A1 (en) | 2014-01-06 | 2015-01-05 | Pyrrolidinyl sulfone derivatives and their use as ror gamma modulators |
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| US9663469B2 (en) | 2013-09-09 | 2017-05-30 | Bristol-Myers Squibb Company | RORγ modulators |
| US9725443B2 (en) | 2013-09-20 | 2017-08-08 | Bristol-Myers Squibb Company | RORγ modulators |
| US9637455B2 (en) | 2014-01-06 | 2017-05-02 | Bristol-Myers Squibb Company | Heterocyclic sulfone RORγ modulators |
| CN106132931B (zh) | 2014-01-06 | 2019-08-02 | 百时美施贵宝公司 | 碳环砜RORγ调节剂 |
| WO2015103507A1 (en) * | 2014-01-06 | 2015-07-09 | Bristol-Myers Squibb Company | Cyclohexyl sulfone rorϒ modulators |
| JOP20200117A1 (ar) | 2014-10-30 | 2017-06-16 | Janssen Pharmaceutica Nv | كحولات ثلاثي فلوروميثيل كمُعدلات للمستقبل النووي جاما تي المرتبط بحمض الريتيونَويك ROR?t |
| ES2767303T3 (es) | 2014-10-30 | 2020-06-17 | Janssen Pharmaceutica Nv | Tiazoles sustituidos por amida como moduladores de Rorgamma T |
| TR201820513T4 (tr) | 2014-10-30 | 2019-02-21 | Janssen Pharmaceutica Nv | Roryt modülatörleri olarak tiazoller. |
| EA033345B1 (ru) | 2015-05-07 | 2019-09-30 | Бристол-Майерс Сквибб Компани | ТРИЦИКЛИЧЕСКИЕ СУЛЬФОНЫ В КАЧЕСТВЕ МОДУЛЯТОРОВ RORγ |
| WO2017170830A1 (ja) * | 2016-03-31 | 2017-10-05 | 武田薬品工業株式会社 | 複素環化合物 |
| TW201803869A (zh) | 2016-04-27 | 2018-02-01 | 健生藥品公司 | 作為ＲＯＲγＴ調節劑之６－胺基吡啶－３－基噻唑 |
| CN110072848A (zh) * | 2016-10-10 | 2019-07-30 | 百时美施贵宝公司 | 作为γ调节剂的三环砜 |
| JP7083823B2 (ja) * | 2016-10-13 | 2022-06-13 | ブリストル－マイヤーズ スクイブ カンパニー | ＲＯＲγ修飾因子としてのヘテロ環スルホン類 |
| ES2820535T3 (es) * | 2016-11-09 | 2021-04-21 | Bristol Myers Squibb Co | Sulfonas tricíclicas como moduladores de ROR gamma |
| JP2019534301A (ja) * | 2016-11-10 | 2019-11-28 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｒｏｒガンマ調節剤 |
| CN112292183A (zh) | 2018-06-18 | 2021-01-29 | 詹森药业有限公司 | 作为RORγt的调节剂的6-氨基吡啶-3-基吡唑 |
| ES2929140T3 (es) | 2018-06-18 | 2022-11-25 | Janssen Pharmaceutica Nv | Imidazoles sustituidos con fenilo y piridinilo como moduladores de RORgammat |
| JP2021529161A (ja) | 2018-06-18 | 2021-10-28 | ヤンセン ファーマシューティカ エヌ．ベー． | ＲＯＲγｔのモジュレーターとしてのピリジニルピラゾール |
| US10975037B2 (en) | 2018-06-18 | 2021-04-13 | Janssen Pharmaceutica Nv | Phenyl substituted pyrazoles as modulators of RORγt |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| WO2020231713A1 (en) * | 2019-05-13 | 2020-11-19 | Bristol-Myers Squibb Company | AGONISTS OF ROR GAMMAt |
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| US20140243302A1 (en) | 2011-06-27 | 2014-08-28 | Merck Sharp & Dohme Corporation | Bridged bicyclic compounds for the treatment of bacterial infections |
| US20130190356A1 (en) * | 2011-12-22 | 2013-07-25 | Genentech, Inc. | Benzyl sulfonamide derivatives as rorc modulators |
| RU2014149149A (ru) * | 2012-05-08 | 2016-07-10 | Мерк Шарп И Доум Корп. | БИЦИКЛИЧЕСКИЕ СУЛЬФОНОВЫЕ СОЕДИНЕНИЯ ДЛЯ ИНГИБИРОВАНИЯ RORгамма АКТИВНОСТИ И ЛЕЧЕНИЯ ЗАБОЛЕВАНИЯ |
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| WO2014028669A1 (en) * | 2012-08-15 | 2014-02-20 | Biogen Idec Ma Inc. | Novel compounds for modulation of ror-gamma activity |
| US9637455B2 (en) | 2014-01-06 | 2017-05-02 | Bristol-Myers Squibb Company | Heterocyclic sulfone RORγ modulators |
| CN106132931B (zh) | 2014-01-06 | 2019-08-02 | 百时美施贵宝公司 | 碳环砜RORγ调节剂 |
| WO2015103507A1 (en) | 2014-01-06 | 2015-07-09 | Bristol-Myers Squibb Company | Cyclohexyl sulfone rorϒ modulators |
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| EP3092229A1 (en) | 2016-11-16 |
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| US9458171B2 (en) | 2016-10-04 |
| EA030849B1 (ru) | 2018-10-31 |
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