CA2879341C - 2- (azaindol-2-yl) benzimidazoles as pad4 inhibitors - Google Patents
2- (azaindol-2-yl) benzimidazoles as pad4 inhibitors Download PDFInfo
- Publication number
- CA2879341C CA2879341C CA2879341A CA2879341A CA2879341C CA 2879341 C CA2879341 C CA 2879341C CA 2879341 A CA2879341 A CA 2879341A CA 2879341 A CA2879341 A CA 2879341A CA 2879341 C CA2879341 C CA 2879341C
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- Canada
- Prior art keywords
- pyrrolo
- compound
- formula
- methyl
- pyridin
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title abstract description 17
- VEZJRJGLFIXQHG-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-1h-benzimidazole Chemical class C1=CC=C2NC(C=3NC4=CC=CC=C4N=3)=NC2=C1 VEZJRJGLFIXQHG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 319
- 150000003839 salts Chemical class 0.000 claims abstract description 132
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 88
- 239000001257 hydrogen Substances 0.000 claims abstract description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 48
- 238000011282 treatment Methods 0.000 claims abstract description 42
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 25
- 206010025135 lupus erythematosus Diseases 0.000 claims abstract description 22
- 206010047115 Vasculitis Diseases 0.000 claims abstract description 18
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 17
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 15
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 13
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 13
- 201000011510 cancer Diseases 0.000 claims abstract description 13
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims abstract description 13
- 201000003883 Cystic fibrosis Diseases 0.000 claims abstract description 12
- 208000006673 asthma Diseases 0.000 claims abstract description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 20
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 54
- -1 (R)-(3-aminopiperidin-1-yl)(2-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-methyl-(trifluoromethoxy)-1H-benzo[d]imidazol-5-yl)methanone Chemical compound 0.000 claims description 53
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- PYUZHTRYLVLMAP-UHFFFAOYSA-N (3-aminopiperidin-1-yl)-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCCC(N)C1 PYUZHTRYLVLMAP-UHFFFAOYSA-N 0.000 claims 1
- YEKXWBBPTLBIFX-UHFFFAOYSA-N (3-aminopiperidin-1-yl)-[2-(1-ethylpyrrolo[3,2-c]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CN=CC=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCCC(N)C1 YEKXWBBPTLBIFX-UHFFFAOYSA-N 0.000 claims 1
- DFMWXZVRHCUIDX-MRXNPFEDSA-N [(3r)-3-aminopiperidin-1-yl]-[1-methyl-2-[1-(2,2,2-trifluoroethyl)pyrrolo[2,3-b]pyridin-2-yl]benzimidazol-5-yl]methanone Chemical compound C=1C=C2N(C)C(C=3N(C4=NC=CC=C4C=3)CC(F)(F)F)=NC2=CC=1C(=O)N1CCC[C@@H](N)C1 DFMWXZVRHCUIDX-MRXNPFEDSA-N 0.000 claims 1
- QWCHTDZPCMJADP-MRXNPFEDSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethyl-5-hydroxypyrrolo[2,3-b]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC(O)=CN=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 QWCHTDZPCMJADP-MRXNPFEDSA-N 0.000 claims 1
- CUZDPEBQVSHMAS-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethyl-5-methoxypyrrolo[2,3-b]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC(OC)=CN=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 CUZDPEBQVSHMAS-QGZVFWFLSA-N 0.000 claims 1
- MKKDRCQQVXGTHG-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethyl-5-methoxypyrrolo[2,3-c]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC(OC)=NC=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 MKKDRCQQVXGTHG-QGZVFWFLSA-N 0.000 claims 1
- PYUZHTRYLVLMAP-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 PYUZHTRYLVLMAP-QGZVFWFLSA-N 0.000 claims 1
- FCYWSVRTUOKPKB-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-(2-methoxyethyl)benzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=C(OC)C=2)CCOC)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 FCYWSVRTUOKPKB-LJQANCHMSA-N 0.000 claims 1
- LMJKAUYYQOXVBH-HXUWFJFHSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-(2-methylpropyl)benzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=C(OC)C=2)CC(C)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 LMJKAUYYQOXVBH-HXUWFJFHSA-N 0.000 claims 1
- JCCVZBCVMBEDEN-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=C(OC)C=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 JCCVZBCVMBEDEN-QGZVFWFLSA-N 0.000 claims 1
- PXEKOCDKODNCAO-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-c]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=NC=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 PXEKOCDKODNCAO-QGZVFWFLSA-N 0.000 claims 1
- XLHNIITZJSBCTN-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[2-[1-(2,2-dimethylpropyl)pyrrolo[2,3-b]pyridin-2-yl]-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C=2N=C(C=3N(C4=NC=CC=C4C=3)CC(C)(C)C)N(C)C=2C(OC)=CC=1C(=O)N1CCC[C@@H](N)C1 XLHNIITZJSBCTN-LJQANCHMSA-N 0.000 claims 1
- PZGSGOGBUMTSJY-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[2-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-2-yl]-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C=C2N(C)C(C=3N(C4=NC=CC=C4C=3)CC3CC3)=NC2=CC=1C(=O)N1CCC[C@@H](N)C1 PZGSGOGBUMTSJY-LJQANCHMSA-N 0.000 claims 1
- KNMCDXAIVNPMQX-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[2-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-2-yl]-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound CN1C=2C(OC)=CC(C(=O)N3C[C@H](N)CCC3)=CC=2N=C1C1=CC2=CC=CN=C2N1CC1CC1 KNMCDXAIVNPMQX-LJQANCHMSA-N 0.000 claims 1
- NGVGPCGPMJWOCO-MRXNPFEDSA-N [(3r)-3-aminopiperidin-1-yl]-[7-methoxy-1-methyl-2-[1-(2,2,2-trifluoroethyl)pyrrolo[2,3-b]pyridin-2-yl]benzimidazol-5-yl]methanone Chemical compound C=1C=2N=C(C=3N(C4=NC=CC=C4C=3)CC(F)(F)F)N(C)C=2C(OC)=CC=1C(=O)N1CCC[C@@H](N)C1 NGVGPCGPMJWOCO-MRXNPFEDSA-N 0.000 claims 1
- VXZHYWCKALGSDQ-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[7-methoxy-1-methyl-2-[1-(2-methylpropyl)pyrrolo[2,3-b]pyridin-2-yl]benzimidazol-5-yl]methanone Chemical compound C=1C=2N=C(C=3N(C4=NC=CC=C4C=3)CC(C)C)N(C)C=2C(OC)=CC=1C(=O)N1CCC[C@@H](N)C1 VXZHYWCKALGSDQ-LJQANCHMSA-N 0.000 claims 1
- FQGRLSQSAFNRCE-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[7-methoxy-2-[1-(2-methoxy-2-methylpropyl)pyrrolo[2,3-b]pyridin-2-yl]-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C=2N=C(C=3N(C4=NC=CC=C4C=3)CC(C)(C)OC)N(C)C=2C(OC)=CC=1C(=O)N1CCC[C@@H](N)C1 FQGRLSQSAFNRCE-LJQANCHMSA-N 0.000 claims 1
- JCCVZBCVMBEDEN-KRWDZBQOSA-N [(3s)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=C(OC)C=2)C)=NC1=CC=2C(=O)N1CCC[C@H](N)C1 JCCVZBCVMBEDEN-KRWDZBQOSA-N 0.000 claims 1
- LGMQWHDIEKFXIE-PGRDOPGGSA-N [(3s,4r)-3-amino-4-hydroxypiperidin-1-yl]-[2-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-2-yl]-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C=C2N(C)C(C=3N(C4=NC=CC=C4C=3)CC3CC3)=NC2=CC=1C(=O)N1CC[C@@H](O)[C@@H](N)C1 LGMQWHDIEKFXIE-PGRDOPGGSA-N 0.000 claims 1
- SHBUAYSOPVZNDD-GHTZIAJQSA-N [(3s,4r)-3-amino-4-hydroxypiperidin-1-yl]-[2-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-2-yl]-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound CN1C=2C(OC)=CC(C(=O)N3C[C@H](N)[C@H](O)CC3)=CC=2N=C1C1=CC2=CC=CN=C2N1CC1CC1 SHBUAYSOPVZNDD-GHTZIAJQSA-N 0.000 claims 1
- 102100035731 Protein-arginine deiminase type-4 Human genes 0.000 abstract description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 49
- 101100406797 Arabidopsis thaliana PAD4 gene Proteins 0.000 abstract description 46
- 101150094373 Padi4 gene Proteins 0.000 abstract description 46
- 208000035475 disorder Diseases 0.000 abstract description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 414
- 238000000034 method Methods 0.000 description 177
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
- 239000000243 solution Substances 0.000 description 132
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 120
- 229910001868 water Inorganic materials 0.000 description 118
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 115
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 112
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 61
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 58
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- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 49
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- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 38
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Rheumatology (AREA)
- Pulmonology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| PCT/EP2012/064649 WO2014015905A1 (en) | 2012-07-26 | 2012-07-26 | 2 - (azaindol- 2 -yl) benz imidazoles as pad4 inhibitors |
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| CA2879341A1 CA2879341A1 (en) | 2014-01-30 |
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| AR107030A1 (es) * | 2015-12-09 | 2018-03-14 | Padlock Therapeutics Inc | Inhibidores aza-bencimidazol de pad4 |
| CN109071497B (zh) * | 2016-02-23 | 2021-10-22 | 帕德罗科治疗公司 | Pad4杂芳基抑制剂 |
| CN107188867A (zh) * | 2016-03-14 | 2017-09-22 | 中国科学院天津工业生物技术研究所 | 精氨酸脱亚氨酶4的抑制剂 |
| ES2828623T3 (es) * | 2016-07-27 | 2021-05-27 | Padlock Therapeutics Inc | Inhibidores covalentes de PAD4 |
| KR102502992B1 (ko) * | 2016-09-12 | 2023-02-24 | 패들락 테라퓨틱스, 인코포레이티드 | Pad4의 헤테로아릴 억제제 |
| US11208386B2 (en) | 2016-12-02 | 2021-12-28 | University Of Massachusetts | Inhibitors of protein arginine deiminases (PADs) and methods of preparation and use thereof |
| CN108689946B (zh) * | 2017-04-12 | 2022-10-18 | 中国科学院上海药物研究所 | 2-取代硫基乙酰胺类化合物及其制备方法和应用 |
| DK3684767T3 (da) * | 2017-09-22 | 2024-07-15 | Jubilant Epipad LLC | Heterocykliske forbindelser som pad-inhibitorer |
| AU2018352142B2 (en) * | 2017-10-18 | 2022-08-25 | Jubilant Epipad LLC | Imidazo-pyridine compounds as PAD inhibitors |
| CN111386265A (zh) | 2017-11-06 | 2020-07-07 | 朱比连特普罗德尔有限责任公司 | 作为pd1/pd-l1活化的抑制剂的嘧啶衍生物 |
| SMT202400203T1 (it) | 2017-11-24 | 2024-07-09 | Jubilant Episcribe Llc | Composti eterociclici come inibitori di prmt5 |
| EP3760628A4 (en) * | 2018-02-26 | 2021-10-13 | Nanjing Transthera Biosciences Co., Ltd. | PEPTIDYLARGININE DEIMINASE INHIBITOR AND ITS USES |
| CA3093527A1 (en) | 2018-03-13 | 2019-09-19 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| EP3801499B1 (en) | 2018-06-07 | 2024-02-28 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 |
| EP3833440A1 (en) | 2018-08-08 | 2021-06-16 | Bristol-Myers Squibb Company | Indole and azaindole inhibitors of pad enzymes |
| KR20210042933A (ko) * | 2018-08-08 | 2021-04-20 | 브리스톨-마이어스 스큅 컴퍼니 | Pad 효소의 벤즈이미다졸 억제제 |
| ES2973714T3 (es) * | 2018-08-08 | 2024-06-24 | Bristol Myers Squibb Co | Bencimidazoles sustituidos como inhibidores de PAD4 |
| ES2929200T3 (es) | 2018-08-08 | 2022-11-25 | Bristol Myers Squibb Co | Tienopirroles sustituidos como inhibidores de PAD4 |
| CN109369513B (zh) * | 2018-11-20 | 2020-08-25 | 都创(上海)医药科技有限公司 | 一种fbdd常用分子片段的制备方法 |
| EP3897670A4 (en) | 2018-12-19 | 2022-09-07 | Disarm Therapeutics, Inc. | MRSA1 INHIBITORS IN COMBINATION WITH NEUROPROTECTIVE AGENTS |
| EP3994128A4 (en) * | 2019-07-03 | 2022-12-07 | University of Massachusetts | INHIBITORS OF PROTEIN ARGININE DEIMINASE 1, AND PROCESSES FOR THEIR PREPARATION AND USE |
| TW202115083A (zh) * | 2019-09-27 | 2021-04-16 | 大陸商南京藥捷安康生物科技有限公司 | 肽醯精胺酸脫亞胺酶抑制劑及其用途 |
| EP4100405A1 (en) * | 2020-02-06 | 2022-12-14 | Bristol-Myers Squibb Company | Macrocyclic pad4 inhibitors useful as immunosuppressant |
| TW202140477A (zh) * | 2020-02-12 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 雜環ｐａｄ４抑制劑 |
| CN111265526B (zh) * | 2020-04-09 | 2021-03-19 | 黑龙江中医药大学 | 一种治疗胃癌的药物及其制备方法 |
| EP4143189A1 (en) | 2020-04-30 | 2023-03-08 | Gilead Sciences, Inc. | Macrocyclic inhibitors of peptidylarginine deiminases |
| CA3192236A1 (en) | 2020-09-10 | 2022-03-17 | Tony Lahoutte | Antibody fragment against fap |
| JP7706775B2 (ja) | 2020-09-18 | 2025-07-14 | カルナバイオサイエンス株式会社 | アミン誘導体 |
| EP4267587A2 (en) | 2020-12-22 | 2023-11-01 | Gilead Sciences, Inc. | Inhibitors of peptidylarginine deiminases |
| EP4267562A1 (en) | 2020-12-22 | 2023-11-01 | Gilead Sciences, Inc. | Inhibitors of peptidylarginine deiminases |
| WO2023083365A1 (en) | 2021-11-15 | 2023-05-19 | Qilu Regor Therapeutics Inc. | Pad4 inhibitors and use thereof |
| WO2023203135A1 (en) | 2022-04-22 | 2023-10-26 | Precirix N.V. | Improved radiolabelled antibody |
| JP2025517625A (ja) | 2022-05-02 | 2025-06-10 | プレシリックス・ナームローゼ・ベンノートシヤープ | プレターゲティング |
| WO2023230609A1 (en) * | 2022-05-26 | 2023-11-30 | Celgene Corporation | Heterocyclic pad4 inhibitors |
| WO2024109945A1 (en) * | 2022-11-24 | 2024-05-30 | Helios Huaming Biopharma Co., Ltd. | Selenium containing heterocycle compounds and use thereof |
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- 2012-07-26 SI SI201230769A patent/SI2877467T1/sl unknown
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- 2012-07-26 HR HRP20161530TT patent/HRP20161530T1/hr unknown
- 2012-07-26 KR KR1020157005099A patent/KR101916443B1/ko active Active
- 2012-07-26 WO PCT/EP2012/064649 patent/WO2014015905A1/en not_active Ceased
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