JP2015524412A5 - - Google Patents
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- 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
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- 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 (https=) | 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 (https=) |
| EP (1) | EP2875021B1 (https=) |
| JP (1) | JP6215324B2 (https=) |
| KR (1) | KR20150038185A (https=) |
| CN (1) | CN104640857B (https=) |
| AU (1) | AU2013292580B2 (https=) |
| CA (1) | CA2878469A1 (https=) |
| ES (1) | ES2647585T3 (https=) |
| IL (1) | IL236688B (https=) |
| IN (1) | IN2015DN00099A (https=) |
| MX (1) | MX2015000794A (https=) |
| WO (1) | WO2014015054A1 (https=) |
| ZA (1) | ZA201500150B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015048819A1 (en) | 2013-09-30 | 2015-04-02 | 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 |
| WO2016154369A1 (en) * | 2015-03-26 | 2016-09-29 | Merck Sharp & Dohme Corp. | Composition and methods for treating chronic kidney disease |
| SG11201805387RA (en) * | 2015-12-30 | 2018-07-30 | Univ Saint Louis | Meta-azacyclic amino benzoic acid derivatives as pan integrin antagonists |
| EP3509590A4 (en) | 2016-09-07 | 2020-12-02 | Pliant Therapeutics, Inc. | N-ACYL AMINO ACID COMPOUNDS AND METHODS OF USE |
| US11306084B2 (en) * | 2016-12-29 | 2022-04-19 | Saint Louis University | Integrin antagonists |
| MX394210B (es) * | 2017-02-28 | 2025-03-04 | Morphic Therapeutic Inc | INHIBIDORES DE INTEGRINA AVß6. |
| MA52117A (fr) | 2017-02-28 | 2022-04-06 | Morphic Therapeutic Inc | Inhibiteurs de l'intégrine (alpha-v) (bêta-6) |
| 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 |
| FI3761980T3 (fi) * | 2018-03-07 | 2024-02-21 | Pliant Therapeutics Inc | Aminohappoyhdisteitä ja käyttömenetelmiä |
| WO2020047208A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| WO2020047239A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | INHIBITING αV β6 INTEGRIN |
| SI3844162T1 (sl) | 2018-08-29 | 2025-06-30 | Morphic Therapeutic, Inc. | Zaviralci integrina alfa v beta6 |
| CN114173803A (zh) * | 2019-04-08 | 2022-03-11 | 普利安特治疗公司 | 氨基酸化合物的剂型和方案 |
| 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 |
| KR20230011967A (ko) | 2020-05-14 | 2023-01-25 | 유비이 가부시키가이샤 | 1,4,5,6-테트라하이드로피리미딘-2-아민 유도체 |
| WO2023085396A1 (ja) * | 2021-11-12 | 2023-05-19 | Ｕｂｅ株式会社 | アルポート症候群を治療または予防するための医薬組成物 |
| EP4733297A1 (en) * | 2023-06-22 | 2026-04-29 | Antibody Therapeutics, Inc. | Integrin-inhibiting small molecule compound |
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 |
| IL123164A (en) | 1995-08-30 | 2001-03-19 | Searle & Co | Meta-guanidine urea thiourea or azacyclic amino benzoic acid derivatives and pharmaceutical compositions containing them |
| US6013651A (en) | 1995-08-30 | 2000-01-11 | G. D. Searle & Co. | Meta-azacyclic amino benzoic acid compounds and derivatives thereof |
| DE69710319T2 (de) | 1996-03-29 | 2002-08-14 | G.D. SEARLE & CO., CHICAGO | Para-substituierte phenylpropansäure derivate als integrin-antagonisten |
| DK0894084T3 (da) | 1996-03-29 | 2002-10-14 | Searle & Co | Kanelsyrederivater og deres anvendelse som integrinantagonister |
| DE69706407T2 (de) | 1996-03-29 | 2002-05-29 | G.D. Searle & Co., Chicago | META-SUBSTITUIERTE PHENYLENDERIVATE UND IHRE VERWENDUNG ALS ALPHAvBETA3 INTERGRIN-ANTAGONISTEN ODER INHIBITOREN |
| EP0912495B1 (en) | 1996-07-12 | 2001-11-21 | G.D. SEARLE & CO. | Asymetric 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. |
| ZA991105B (en) | 1998-03-04 | 2000-02-11 | Searle & Co | Synthesis of chiral beta-amino acids. |
| ZA994406B (en) | 1998-03-04 | 2000-02-11 | Searle & Co | Meta-azacyclic amino benzoic acid and derivatives thereof. |
| US6372719B1 (en) | 1998-03-04 | 2002-04-16 | Jay Cunningham | ανβ3 integrin antagonists in combination with chemotherapeutic agents |
| KR20010042614A (ko) | 1998-04-10 | 2001-05-25 | 윌리암스 로저 에이 | 비트로넥틴 길항제로서 복소환식 글리실 베타-알라닌 유도체 |
| AU2592600A (en) | 1998-12-23 | 2000-07-31 | G.D. Searle & Co. | Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| US7119098B2 (en) | 2000-06-15 | 2006-10-10 | Pharmacia Corporation | Heteroarylakanoic acids as intergrin receptor antagonists |
| US20020072500A1 (en) * | 2000-09-27 | 2002-06-13 | Thomas Rogers | Hydroxy acid integrin antagonists |
| JP2006514050A (ja) * | 2002-12-20 | 2006-04-27 | ファルマシア・コーポレーション | インテグリン受容体アンタゴニスト誘導体としてのβ−アミノ酸化合物のＲ異性体 |
| ATE399542T1 (de) | 2003-10-01 | 2008-07-15 | 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 |
| US8614221B2 (en) | 2009-03-11 | 2013-12-24 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| AR077975A1 (es) | 2009-08-28 | 2011-10-05 | Irm Llc | Derivados de pirazol pirimidina y composiciones como inhibidores de cinasa de proteina |
| JP5862669B2 (ja) | 2010-08-26 | 2016-02-16 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン産生のオキサジアゾール阻害剤 |
-
2013
- 2013-07-17 WO PCT/US2013/050917 patent/WO2014015054A1/en not_active Ceased
- 2013-07-17 IN IN99DEN2015 patent/IN2015DN00099A/en unknown
- 2013-07-17 CN CN201380048418.3A patent/CN104640857B/zh not_active Expired - Fee Related
- 2013-07-17 EP EP13742135.0A patent/EP2875021B1/en not_active Not-in-force
- 2013-07-17 CA CA2878469A patent/CA2878469A1/en not_active Abandoned
- 2013-07-17 JP JP2015523227A patent/JP6215324B2/ja active Active
- 2013-07-17 US US13/944,599 patent/US9085606B2/en active Active
- 2013-07-17 KR KR20157004419A patent/KR20150038185A/ko not_active Ceased
- 2013-07-17 ES ES13742135.0T patent/ES2647585T3/es active Active
- 2013-07-17 MX MX2015000794A patent/MX2015000794A/es unknown
- 2013-07-17 AU AU2013292580A patent/AU2013292580B2/en not_active Ceased
-
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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