EA030393B1 - МОДУЛЯТОРЫ ROR ГАММА (RORγ) - Google Patents
МОДУЛЯТОРЫ ROR ГАММА (RORγ) Download PDFInfo
- Publication number
- EA030393B1 EA030393B1 EA201691173A EA201691173A EA030393B1 EA 030393 B1 EA030393 B1 EA 030393B1 EA 201691173 A EA201691173 A EA 201691173A EA 201691173 A EA201691173 A EA 201691173A EA 030393 B1 EA030393 B1 EA 030393B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- phenyl
- acetamide
- hexafluoro
- hydroxypropan
- cyclopropylmethyl
- Prior art date
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- 108091008773 RAR-related orphan receptors γ Proteins 0.000 title abstract 3
- -1 hydroxy, methoxy Chemical group 0.000 claims abstract description 218
- 150000001875 compounds Chemical class 0.000 claims abstract description 154
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 125
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 230000001404 mediated effect Effects 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- HBGYOKOCPHASLN-UHFFFAOYSA-N n-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 HBGYOKOCPHASLN-UHFFFAOYSA-N 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000013256 coordination polymer Substances 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000004437 phosphorous atom Chemical group 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 6
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 235000008957 cocaer Nutrition 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- XKRHYAABBAYGBK-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)C(C(F)(F)F)(C)O Chemical compound C(C)(=O)NC1=CC=C(C=C1)C(C(F)(F)F)(C)O XKRHYAABBAYGBK-UHFFFAOYSA-N 0.000 claims description 2
- BVBXPLJKIFYSMP-UHFFFAOYSA-N N-[5-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methoxyphenyl]acetamide Chemical compound C(C)(=O)NC1=C(C=C(C(=C1)F)C(C(F)(F)F)(C(F)(F)F)O)OC BVBXPLJKIFYSMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- APDWVBKPQBQCPP-UHFFFAOYSA-N n-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2,6-dimethylphenyl]acetamide Chemical compound CC(=O)NC1=C(C)C=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1C APDWVBKPQBQCPP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- QJVUSPXVNQEGKC-UHFFFAOYSA-N C(C)(=O)NC1=C(C=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O)C Chemical compound C(C)(=O)NC1=C(C=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O)C QJVUSPXVNQEGKC-UHFFFAOYSA-N 0.000 claims 2
- KVSAXZUHZNSKNA-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O)C Chemical compound C(C)(=O)NC1=CC(=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O)C KVSAXZUHZNSKNA-UHFFFAOYSA-N 0.000 claims 2
- JKKJSVNDZAHPOK-UHFFFAOYSA-N N-[3-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]acetamide Chemical compound C(C)(=O)NC1=CC(=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O)F JKKJSVNDZAHPOK-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 240000006890 Erythroxylum coca Species 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229910052760 oxygen Chemical group 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
- 210000004027 cell Anatomy 0.000 description 43
- 239000011541 reaction mixture Substances 0.000 description 42
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 40
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
- 230000002829 reductive effect Effects 0.000 description 36
- 239000000047 product Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000000034 method Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 235000019341 magnesium sulphate Nutrition 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 21
- 239000012267 brine Substances 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- 238000010828 elution Methods 0.000 description 18
- 229960003424 phenylacetic acid Drugs 0.000 description 18
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- 239000007787 solid Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 108060001084 Luciferase Proteins 0.000 description 9
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- TZEJXCIGVMTMDY-UHFFFAOYSA-N 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical class NC1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 TZEJXCIGVMTMDY-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
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| EP3122721A4 (en) * | 2014-03-27 | 2018-01-10 | Piramal Enterprises Limited | Ror-gamma modulators and uses thereof |
| MX2016013518A (es) * | 2014-04-16 | 2017-01-23 | Glenmark Pharmaceuticals Sa | Compuestos de aril y heteroaril eter como moduladores de ror gamma. |
| JOP20200117A1 (ar) | 2014-10-30 | 2017-06-16 | Janssen Pharmaceutica Nv | كحولات ثلاثي فلوروميثيل كمُعدلات للمستقبل النووي جاما تي المرتبط بحمض الريتيونَويك ROR?t |
| RS58250B1 (sr) | 2014-10-30 | 2019-03-29 | Janssen Pharmaceutica Nv | Tiazoli kao modulatori roryt |
| SMT201900706T1 (it) | 2014-10-30 | 2020-01-14 | Janssen Pharmaceutica Nv | Tiazoli sostituiti con ammide come modulatori di rorgammat |
| CN107614062A (zh) | 2015-03-12 | 2018-01-19 | 加利福尼亚大学董事会 | 用RORγ抑制剂治疗癌症的方法 |
| MX394388B (es) | 2015-05-15 | 2025-03-21 | Aurigene Discovery Tech Ltd | Compuestos de tetrahidroquinolinona sustituidos como moduladores de ror gamma |
| WO2016193894A1 (en) * | 2015-05-29 | 2016-12-08 | Glenmark Pharmaceuticals S.A. | Treatment of respiratory disorders using ror- gamma inhibitors |
| EP3101005A1 (en) * | 2015-06-05 | 2016-12-07 | Lead Pharma Cel Models IP B.V. | Ror gamma (rory) modulators |
| EP3101008A1 (en) | 2015-06-05 | 2016-12-07 | Lead Pharma Cel Models IP B.V. | Ror gamma (rory) modulators |
| WO2017010399A1 (ja) * | 2015-07-10 | 2017-01-19 | 塩野義製薬株式会社 | ＲＯＲγｔ阻害作用を有する化合物およびそれらを含有する医薬組成物 |
| CN109071516B (zh) | 2015-12-15 | 2021-08-31 | 阿斯利康(瑞典)有限公司 | 新颖的化合物 |
| 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 |
| TW201815388A (zh) * | 2016-07-14 | 2018-05-01 | 印度商卡迪拉保健有限公司 | 作為ＲＯＲγ調節劑之新穎化合物 |
| BR112019000603A2 (pt) | 2016-07-14 | 2019-04-30 | Cadila Healthcare Limited | composto, composição farmacêutica, método para o tratamento de doenças e uso do composto |
| AR110481A1 (es) * | 2016-12-05 | 2019-04-03 | Lead Pharma Holding Bv | MODULADORES DE ROR g (RORg) |
| WO2018116285A1 (en) * | 2016-12-23 | 2018-06-28 | Glenmark Pharmaceuticals S.A. | Substituted morpholine derivatives as ror gamma modulators |
| WO2018229155A1 (en) | 2017-06-14 | 2018-12-20 | Astrazeneca Ab | 2,3-dihydroisoindole-1-carboxamides useful as ror-gamma modulators |
| US10975037B2 (en) | 2018-06-18 | 2021-04-13 | Janssen Pharmaceutica Nv | Phenyl substituted pyrazoles as modulators of RORγt |
| JP2021527660A (ja) | 2018-06-18 | 2021-10-14 | ヤンセン ファーマシューティカ エヌ．ベー． | ＲＯＲγｔのモジュレータとしてのフェニル及びピリジニル置換イミダゾール |
| ES2928246T3 (es) | 2018-06-18 | 2022-11-16 | Janssen Pharmaceutica Nv | 6-aminopiridin-3-il pirazoles como moduladores de RORyt |
| CN112292373A (zh) | 2018-06-18 | 2021-01-29 | 詹森药业有限公司 | 作为RORγt的调节剂的吡啶基吡唑类 |
| EP3921038A1 (en) | 2019-02-06 | 2021-12-15 | Dice Alpha, Inc. | Il-17a modulators and uses thereof |
| WO2021055376A1 (en) | 2019-09-16 | 2021-03-25 | Dice Alpha, Inc. | Il-17a modulators and uses thereof |
| CN112759541B (zh) * | 2019-10-21 | 2023-03-17 | 复旦大学 | 类吲哚衍生物及其用途 |
| TW202136238A (zh) * | 2020-01-06 | 2021-10-01 | 大陸商廣東東陽光藥業有限公司 | RORγt抑制劑及其製備方法和用途 |
| CN113072521B (zh) * | 2020-01-06 | 2024-04-05 | 广东东阳光药业股份有限公司 | RORγt抑制剂及其在药物中的应用 |
| CN114075139B (zh) * | 2020-08-14 | 2025-09-26 | 广东东阳光药业股份有限公司 | 五元杂芳环类化合物及其在药物中的应用 |
| WO2025157313A1 (zh) * | 2024-01-26 | 2025-07-31 | 上海医药集团股份有限公司 | 一种乙磺酰苯基乙酰胺类化合物的晶型、其制备方法及应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2011115892A1 (en) * | 2010-03-15 | 2011-09-22 | Griffin Patrick R | Modulators of the retinoic acid receptor-related orphan receptors |
| WO2013029338A1 (en) * | 2011-09-01 | 2013-03-07 | Glaxo Group Limited | Novel compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2012027965A1 (en) * | 2010-09-01 | 2012-03-08 | Glaxo Group Limited | Novel compounds |
| AU2013331493A1 (en) * | 2012-10-16 | 2015-04-09 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORyt |
| WO2013171729A2 (en) | 2013-01-08 | 2013-11-21 | Glenmark Pharmaceuticals S.A. | Aryl and heteroaryl amide compounds as rorgamat modulator |
| RU2015141592A (ru) * | 2013-03-15 | 2017-04-21 | Ф. Хоффманн-Ля Рош Аг | АРИЛ-СУЛЬФАМИДЫ И СУЛЬФАМАТЫ В КАЧЕСТВЕ МОДУЛЯТОРОВ RORc |
| EP2781217A1 (en) * | 2013-03-18 | 2014-09-24 | ETH Zurich | ROR gamma modulators |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011115892A1 (en) * | 2010-03-15 | 2011-09-22 | Griffin Patrick R | Modulators of the retinoic acid receptor-related orphan receptors |
| WO2013029338A1 (en) * | 2011-09-01 | 2013-03-07 | Glaxo Group Limited | Novel compounds |
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