JP2015524412A5 - - Google Patents
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- Publication number
- JP2015524412A5 JP2015524412A5 JP2015523227A JP2015523227A JP2015524412A5 JP 2015524412 A5 JP2015524412 A5 JP 2015524412A5 JP 2015523227 A JP2015523227 A JP 2015523227A JP 2015523227 A JP2015523227 A JP 2015523227A JP 2015524412 A5 JP2015524412 A5 JP 2015524412A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- alkoxy
- present
- hydrogen
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 174
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 68
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 36
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910014033 C-OH Inorganic materials 0.000 claims description 9
- 229910014570 C—OH Inorganic materials 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000002346 iodo group Chemical group I* 0.000 claims description 5
- 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 5
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 56
- 238000000034 method Methods 0.000 description 39
- 201000010099 disease Diseases 0.000 description 28
- 208000035475 disorder Diseases 0.000 description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 206010028980 Neoplasm Diseases 0.000 description 14
- 150000001721 carbon Chemical group 0.000 description 14
- 201000011510 cancer Diseases 0.000 description 10
- 230000037390 scarring Effects 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 206010016654 Fibrosis Diseases 0.000 description 4
- 230000004761 fibrosis Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- -1 9-fluorenylmethyloxycarbonyl Chemical group 0.000 description 3
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- 208000035473 Communicable disease Diseases 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- 0 C*C1(CCOCC1)C#N Chemical compound C*C1(CCOCC1)C#N 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- 208000028506 Familial Exudative Vitreoretinopathies Diseases 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- 208000037147 Hypercalcaemia Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 208000010191 Osteitis Deformans Diseases 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- 208000027868 Paget disease Diseases 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 241000009328 Perro Species 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 description 2
- 206010039710 Scleroderma Diseases 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000033115 angiogenesis Effects 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000009787 cardiac fibrosis Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 208000019425 cirrhosis of liver Diseases 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 201000006902 exudative vitreoretinopathy Diseases 0.000 description 2
- 208000014829 head and neck neoplasm Diseases 0.000 description 2
- 230000000148 hypercalcaemia Effects 0.000 description 2
- 208000030915 hypercalcemia disease Diseases 0.000 description 2
- 208000002780 macular degeneration Diseases 0.000 description 2
- 208000027202 mammary Paget disease Diseases 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 208000028169 periodontal disease Diseases 0.000 description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 description 2
- 201000002793 renal fibrosis Diseases 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 206010005949 Bone cancer Diseases 0.000 description 1
- 208000018084 Bone neoplasm Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- BMAWQIAMODAVER-UHFFFAOYSA-N CC(C(F)(F)F)(c1cc(C(F)(F)F)cc(C(C2)(C2C(O)=O)NC(CNC(c2cc(O)cc(NC(NC3)=NCC3O)c2)=O)=O)c1)O Chemical compound CC(C(F)(F)F)(c1cc(C(F)(F)F)cc(C(C2)(C2C(O)=O)NC(CNC(c2cc(O)cc(NC(NC3)=NCC3O)c2)=O)=O)c1)O BMAWQIAMODAVER-UHFFFAOYSA-N 0.000 description 1
- DNPNUDXUSUMTMG-UHFFFAOYSA-N CNC(NC1)=NCC1O Chemical compound CNC(NC1)=NCC1O DNPNUDXUSUMTMG-UHFFFAOYSA-N 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 206010014733 Endometrial cancer Diseases 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 206010023825 Laryngeal cancer Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- IXWQXGVACPIHDY-QHCPKHFHSA-N N#CC1(CCOCC1)c1cc(Cl)cc([C@H](CC(O)=O)NC(CNC(c2cc(NC(NC3)=NCC3O)cc(O)c2)=O)=O)c1 Chemical compound N#CC1(CCOCC1)c1cc(Cl)cc([C@H](CC(O)=O)NC(CNC(c2cc(NC(NC3)=NCC3O)cc(O)c2)=O)=O)c1 IXWQXGVACPIHDY-QHCPKHFHSA-N 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 206010038934 Retinopathy proliferative Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 206010039580 Scar Diseases 0.000 description 1
- 201000010208 Seminoma Diseases 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 208000000277 Splenic Neoplasms Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000008385 Urogenital Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 201000007455 central nervous system cancer Diseases 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 201000004101 esophageal cancer Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000010175 gallbladder cancer Diseases 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 201000005787 hematologic cancer Diseases 0.000 description 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 206010023841 laryngeal neoplasm Diseases 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 208000026037 malignant tumor of neck Diseases 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000002200 mouth mucosa Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- 208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000006785 proliferative vitreoretinopathy Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 201000002314 small intestine cancer Diseases 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 201000002471 spleen cancer Diseases 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 208000037964 urogenital cancer Diseases 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261673058P | 2012-07-18 | 2012-07-18 | |
| US61/673,058 | 2012-07-18 | ||
| US201361764443P | 2013-02-13 | 2013-02-13 | |
| US61/764,443 | 2013-02-13 | ||
| PCT/US2013/050917 WO2014015054A1 (en) | 2012-07-18 | 2013-07-17 | Beta amino acid derivatives as integrin antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015524412A JP2015524412A (ja) | 2015-08-24 |
| JP2015524412A5 true JP2015524412A5 (OSRAM) | 2016-08-18 |
| JP6215324B2 JP6215324B2 (ja) | 2017-10-18 |
Family
ID=48875802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015523227A Active JP6215324B2 (ja) | 2012-07-18 | 2013-07-17 | インテグリンアンタゴニストとしてのβアミノ酸誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9085606B2 (OSRAM) |
| EP (1) | EP2875021B1 (OSRAM) |
| JP (1) | JP6215324B2 (OSRAM) |
| KR (1) | KR20150038185A (OSRAM) |
| CN (1) | CN104640857B (OSRAM) |
| AU (1) | AU2013292580B2 (OSRAM) |
| CA (1) | CA2878469A1 (OSRAM) |
| ES (1) | ES2647585T3 (OSRAM) |
| IL (1) | IL236688B (OSRAM) |
| IN (1) | IN2015DN00099A (OSRAM) |
| MX (1) | MX2015000794A (OSRAM) |
| WO (1) | WO2014015054A1 (OSRAM) |
| ZA (1) | ZA201500150B (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014324426A1 (en) | 2013-09-30 | 2016-04-21 | The Regents Of The University Of California | Anti-alphavbeta1 integrin compounds and methods |
| WO2016145258A1 (en) * | 2015-03-10 | 2016-09-15 | The Regents Of The University Of California | Anti-alphavbeta1 integrin inhibitors and methods of use |
| US20180110762A1 (en) * | 2015-03-26 | 2018-04-26 | Merck Sharp & Dohme Corp | Compositions Methods for Treating Chronic Kidney Disease |
| RU2729518C2 (ru) * | 2015-12-30 | 2020-08-07 | Сент-Луис Юниверсити | Мета-азациклические производные аминобензойной кислоты в качестве антагонистов пан-интегрина |
| TW201823208A (zh) | 2016-09-07 | 2018-07-01 | 美商普萊恩醫療公司 | N－醯基胺基酸化合物及其使用方法 |
| MX2019007797A (es) * | 2016-12-29 | 2019-10-21 | Univ Saint Louis | Antagonistas de integrinas. |
| EP3589285A4 (en) | 2017-02-28 | 2020-08-12 | Morphic Therapeutic, Inc. | INHIBITORS OF INTEGRIN (ALPHA-V) (BETA-6) |
| CN116283977A (zh) | 2017-02-28 | 2023-06-23 | 莫菲克医疗股份有限公司 | αvβ6整合蛋白的抑制剂 |
| CN109879969B (zh) * | 2017-12-06 | 2024-04-09 | 天士力生物医药股份有限公司 | 一种hm-3融合蛋白及其应用 |
| PE20201502A1 (es) * | 2018-03-07 | 2020-12-29 | Pliant Therapeutics Inc | Compuestos de aminoacidos y metodos de uso |
| SG11202101913PA (en) | 2018-08-29 | 2021-03-30 | Morphic Therapeutic Inc | INHIBITING aV ß6 INTEGRIN |
| US11419869B2 (en) | 2019-04-08 | 2022-08-23 | Pliant Therapeutics, Inc. | Dosage forms and regimens for amino acid compounds |
| CN110974938A (zh) * | 2019-12-02 | 2020-04-10 | 上海长海医院 | 整合素α1β1抑制剂在制备预防或治疗主动脉疾病药物中的应用 |
| JP7661969B2 (ja) * | 2020-05-14 | 2025-04-15 | Ｕｂｅ株式会社 | １，４，５，６－テトラヒドロピリミジン－２－アミン誘導体 |
| EP4431098A4 (en) * | 2021-11-12 | 2025-10-08 | Ube Corp | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OR PREVENTION OF ALPORT SYNDROME |
| WO2024262620A1 (ja) * | 2023-06-22 | 2024-12-26 | 株式会社抗体医学研究所 | インテグリン阻害低分子化合物 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5639765A (en) | 1995-01-17 | 1997-06-17 | G. D. Searle & Co. | Guanidinoalkyl glycine β-amino acids useful for inhibiting bone loss |
| US5602155A (en) | 1995-01-17 | 1997-02-11 | G. D. Searle & Co. | Platelet aggregation inhibitors |
| US5681820A (en) | 1995-05-16 | 1997-10-28 | G. D. Searle & Co. | Guanidinoalkyl glycine β-amino acids useful for inhibiting tumor metastasis |
| US6013651A (en) | 1995-08-30 | 2000-01-11 | G. D. Searle & Co. | Meta-azacyclic amino benzoic acid compounds and derivatives thereof |
| NZ318926A (en) | 1995-08-30 | 1999-04-29 | Searle & Co | Alpha v beta 3 integrin (vitronectin) inhibitors or anatagonists derived from benzoic acid for treating diseases of cell adhesion |
| AU2337097A (en) | 1996-03-29 | 1997-10-22 | G.D. Searle & Co. | Meta-substituted phenylene derivatives and their use as alphavbeta3 integrin antagonists or inhibitors |
| WO1997036860A1 (en) | 1996-03-29 | 1997-10-09 | G.D. Searle & Co. | Cinnamic acid derivatives and their use as integrin antagonists |
| JP2000515493A (ja) | 1996-03-29 | 2000-11-21 | ジー．ディー．サール アンド カンパニー | パラ―置換フェニレン誘導体 |
| EP0912495B1 (en) | 1996-07-12 | 2001-11-21 | G.D. SEARLE & CO. | Asymetric synthesis of chiral beta-amino acids |
| US6372719B1 (en) | 1998-03-04 | 2002-04-16 | Jay Cunningham | ανβ3 integrin antagonists in combination with chemotherapeutic agents |
| ZA994406B (en) | 1998-03-04 | 2000-02-11 | Searle & Co | Meta-azacyclic amino benzoic acid and derivatives thereof. |
| ZA991105B (en) | 1998-03-04 | 2000-02-11 | Searle & Co | Synthesis of chiral beta-amino acids. |
| ZA991107B (en) | 1998-03-04 | 2000-02-14 | Searle & Co | Process for preparing 3-hydroxy-5-[(1,4,5,6-tetrahydro-5-hydroxy-2-pyrimidinyl)amino] benzoic acid. |
| NZ507292A (en) | 1998-04-10 | 2003-12-19 | G | Heterocyclic glycyl beta-alanine derivatives useful as vitronectin antagonists |
| JP2002533404A (ja) | 1998-12-23 | 2002-10-08 | ジー・ディー・サール・アンド・カンパニー | 新生物形成の治療における組合わせ療法としてインテグリン拮抗剤及び放射線治療を使用する方法 |
| WO2001096334A2 (en) | 2000-06-15 | 2001-12-20 | Pharmacia Corporation | Heteroarylalkanoic acids as integrin receptor antagonists |
| US20020072500A1 (en) * | 2000-09-27 | 2002-06-13 | Thomas Rogers | Hydroxy acid integrin antagonists |
| AU2003299600A1 (en) * | 2002-12-20 | 2004-07-29 | Pharmacia Corpration | The r-isomer of beta amino acid compounds as integrin receptor antagonists derivatives |
| DE602004014795D1 (de) | 2003-10-01 | 2008-08-14 | Merck Patent Gmbh | Alfavbeta3 und alfavbeta6 integrin antagonisten als antifibrotische mittel |
| TWI433839B (zh) | 2006-08-11 | 2014-04-11 | Neomed Inst | 新穎的苯并咪唑衍生物290 |
| WO2010010184A1 (en) | 2008-07-25 | 2010-01-28 | Galapagos Nv | [1, 2, 4] triazolo [1, 5-a] pyridines as jak inhibitors |
| EP2406250B1 (en) | 2009-03-11 | 2015-08-12 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| JO3002B1 (ar) | 2009-08-28 | 2016-09-05 | Irm Llc | مركبات و تركيبات كمثبطات كيناز بروتين |
| EP2609092B1 (en) | 2010-08-26 | 2015-04-01 | Boehringer Ingelheim International GmbH | Oxadiazole inhibitors of leukotriene production |
-
2013
- 2013-07-17 MX MX2015000794A patent/MX2015000794A/es unknown
- 2013-07-17 AU AU2013292580A patent/AU2013292580B2/en not_active Ceased
- 2013-07-17 IN IN99DEN2015 patent/IN2015DN00099A/en unknown
- 2013-07-17 ES ES13742135.0T patent/ES2647585T3/es active Active
- 2013-07-17 WO PCT/US2013/050917 patent/WO2014015054A1/en not_active Ceased
- 2013-07-17 CA CA2878469A patent/CA2878469A1/en not_active Abandoned
- 2013-07-17 KR KR20157004419A patent/KR20150038185A/ko not_active Ceased
- 2013-07-17 US US13/944,599 patent/US9085606B2/en active Active
- 2013-07-17 CN CN201380048418.3A patent/CN104640857B/zh not_active Expired - Fee Related
- 2013-07-17 JP JP2015523227A patent/JP6215324B2/ja active Active
- 2013-07-17 EP EP13742135.0A patent/EP2875021B1/en not_active Not-in-force
-
2015
- 2015-01-09 ZA ZA2015/00150A patent/ZA201500150B/en unknown
- 2015-01-12 IL IL236688A patent/IL236688B/en active IP Right Grant
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