JP2012509936A5 - - Google Patents
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- JP2012509936A5 JP2012509936A5 JP2011538598A JP2011538598A JP2012509936A5 JP 2012509936 A5 JP2012509936 A5 JP 2012509936A5 JP 2011538598 A JP2011538598 A JP 2011538598A JP 2011538598 A JP2011538598 A JP 2011538598A JP 2012509936 A5 JP2012509936 A5 JP 2012509936A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- methoxy
- cyclohexyl
- pyrazol
- phenyl
- 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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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 1734
- -1 Ano Chemical group 0.000 claims description 710
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 582
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 582
- 150000001875 compounds Chemical class 0.000 claims description 111
- 125000003118 aryl group Chemical group 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 61
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 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 description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 42
- 239000012453 solvate Substances 0.000 claims description 42
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 40
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 35
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 30
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 30
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 30
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 30
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 27
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 17
- 150000004677 hydrates Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
- 102000009079 Epoprostenol Receptors Human genes 0.000 claims description 15
- 108010073099 Epoprostenol Receptors Proteins 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 208000014777 Pulmonary venoocclusive disease Diseases 0.000 claims description 14
- 150000003857 carboxamides Chemical class 0.000 claims description 13
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 12
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 12
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 12
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- 208000035478 Interatrial communication Diseases 0.000 claims description 10
- 208000031467 Pulmonary capillary hemangiomatosis Diseases 0.000 claims description 10
- 206010063837 Reperfusion injury Diseases 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 208000001910 Ventricular Heart Septal Defects Diseases 0.000 claims description 10
- 208000006673 asthma Diseases 0.000 claims description 10
- 208000013914 atrial heart septal defect Diseases 0.000 claims description 10
- 206010003664 atrial septal defect Diseases 0.000 claims description 10
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 10
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 10
- 208000037803 restenosis Diseases 0.000 claims description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
- 201000003130 ventricular septal defect Diseases 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims description 5
- 206010003178 Arterial thrombosis Diseases 0.000 claims description 5
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 5
- 201000002829 CREST Syndrome Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000029147 Collagen-vascular disease Diseases 0.000 claims description 5
- 208000002330 Congenital Heart Defects Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 5
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 5
- 206010012667 Diabetic glaucoma Diseases 0.000 claims description 5
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
- 208000031886 HIV Infections Diseases 0.000 claims description 5
- 208000037357 HIV infectious disease Diseases 0.000 claims description 5
- 208000031953 Hereditary hemorrhagic telangiectasia Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000020875 Idiopathic pulmonary arterial hypertension Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 208000021068 Pulmonary arterial hypertension associated with portal hypertension Diseases 0.000 claims description 5
- 206010039710 Scleroderma Diseases 0.000 claims description 5
- 206010040047 Sepsis Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 208000001106 Takayasu Arteritis Diseases 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 5
- 206010052779 Transplant rejections Diseases 0.000 claims description 5
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 230000002159 abnormal effect Effects 0.000 claims description 5
- 206010000496 acne Diseases 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 5
- 230000007214 atherothrombosis Effects 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 208000028831 congenital heart disease Diseases 0.000 claims description 5
- 208000029078 coronary artery disease Diseases 0.000 claims description 5
- 201000001981 dermatomyositis Diseases 0.000 claims description 5
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 230000037406 food intake Effects 0.000 claims description 5
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 230000004410 intraocular pressure Effects 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 208000003278 patent ductus arteriosus Diseases 0.000 claims description 5
- 208000005987 polymyositis Diseases 0.000 claims description 5
- 238000010911 splenectomy Methods 0.000 claims description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- 239000003053 toxin Substances 0.000 claims description 5
- 231100000765 toxin Toxicity 0.000 claims description 5
- 108700012359 toxins Proteins 0.000 claims description 5
- 210000003462 vein Anatomy 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
- 230000002490 cerebral effect Effects 0.000 claims description 4
- 230000000302 ischemic effect Effects 0.000 claims description 4
- 230000001052 transient effect Effects 0.000 claims description 4
- GLAMVSLFXKZMDJ-UHFFFAOYSA-N 2-[[4-[[5-(2-hydroxyethylsulfanyl)-3,4-diphenylpyrazol-1-yl]methyl]cyclohexyl]methoxy]acetic acid Chemical compound OCCSC1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NN1CC1CCC(COCC(O)=O)CC1 GLAMVSLFXKZMDJ-UHFFFAOYSA-N 0.000 claims description 3
- ZMROZIDRJCRQLR-UHFFFAOYSA-N 2-[[4-[[5-methylsulfanyl-4-(5-methylthiophen-2-yl)-3-phenylpyrazol-1-yl]methyl]cyclohexyl]methoxy]acetic acid Chemical compound C=1C=CC=CC=1C1=NN(CC2CCC(COCC(O)=O)CC2)C(SC)=C1C1=CC=C(C)S1 ZMROZIDRJCRQLR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- KAHKWAPEWNQHDG-UHFFFAOYSA-N 2-[[4-[[4-(5-fluoropyridin-3-yl)-5-methylsulfanyl-3-phenylpyrazol-1-yl]methyl]cyclohexyl]methoxy]acetic acid Chemical compound CSC1=C(C=2C=C(F)C=NC=2)C(C=2C=CC=CC=2)=NN1CC1CCC(COCC(O)=O)CC1 KAHKWAPEWNQHDG-UHFFFAOYSA-N 0.000 claims description 2
- LQLBVRMQYUIDPG-UHFFFAOYSA-N 2-[[4-[[5-(2-hydroxyethylsulfanyl)-4-(3-methoxyphenyl)-3-phenylpyrazol-1-yl]methyl]cyclohexyl]methoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=NN(CC3CCC(COCC(O)=O)CC3)C=2SCCO)C=2C=CC=CC=2)=C1 LQLBVRMQYUIDPG-UHFFFAOYSA-N 0.000 claims description 2
- DVZKKBXNFCNCGU-UHFFFAOYSA-N 2-[[4-[[5-(cyanomethylsulfanyl)-3,4-diphenylpyrazol-1-yl]methyl]cyclohexyl]methoxy]acetic acid Chemical compound C1CC(COCC(=O)O)CCC1CN1C(SCC#N)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N1 DVZKKBXNFCNCGU-UHFFFAOYSA-N 0.000 claims description 2
- RWHCRCWTCOAPSA-UHFFFAOYSA-N 2-[[4-[[5-ethylsulfanyl-4-(2-fluoro-3-methoxyphenyl)-3-phenylpyrazol-1-yl]methyl]cyclohexyl]methoxy]acetic acid Chemical compound CCSC1=C(C=2C(=C(OC)C=CC=2)F)C(C=2C=CC=CC=2)=NN1CC1CCC(COCC(O)=O)CC1 RWHCRCWTCOAPSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 36
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 24
- 208000020193 Pulmonary artery hypoplasia Diseases 0.000 claims 24
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 23
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 claims 1
- 208000032109 Transient ischaemic attack Diseases 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- XSTBCICLDQSQIQ-UHFFFAOYSA-N indeno[2,1-c]pyrazole Chemical compound C1=CC=C2C3=CN=NC3=CC2=C1 XSTBCICLDQSQIQ-UHFFFAOYSA-N 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 claims 1
- 201000010875 transient cerebral ischemia Diseases 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 47
- 125000004414 alkyl thio group Chemical group 0.000 description 36
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 24
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 125000003944 tolyl group Chemical group 0.000 description 5
- 210000003492 pulmonary vein Anatomy 0.000 description 3
- 0 *c1c(*)[n](C[C@]2CC[C@@](COCC(O)=O)CC2)nc1* Chemical compound *c1c(*)[n](C[C@]2CC[C@@](COCC(O)=O)CC2)nc1* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20039308P | 2008-11-26 | 2008-11-26 | |
| US61/200,393 | 2008-11-26 | ||
| PCT/US2009/006251 WO2010068242A1 (en) | 2008-11-26 | 2009-11-24 | Pyrazolyl substituted carbonic acid derivatives as modulators of the prostacyclin (pgi2) receptor useful for the treatment of disorders related thereto |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012509936A JP2012509936A (ja) | 2012-04-26 |
| JP2012509936A5 true JP2012509936A5 (enExample) | 2012-12-27 |
| JP5603343B2 JP5603343B2 (ja) | 2014-10-08 |
Family
ID=41718771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011538598A Active JP5603343B2 (ja) | 2008-11-26 | 2009-11-24 | 関連する障害を処置するために有用なプロスタサイクリン（ｐｇｉ２）受容体モジュレーターとしてのピラゾリル置換炭酸誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (6) | US20110224262A1 (enExample) |
| EP (2) | EP2367797A1 (enExample) |
| JP (1) | JP5603343B2 (enExample) |
| KR (1) | KR101707247B1 (enExample) |
| CN (1) | CN102292321B (enExample) |
| AU (1) | AU2009325117C1 (enExample) |
| BR (1) | BRPI0921369B8 (enExample) |
| CA (1) | CA2744124C (enExample) |
| EA (1) | EA022799B1 (enExample) |
| IL (1) | IL212966A (enExample) |
| MX (1) | MX2011005577A (enExample) |
| NZ (1) | NZ593002A (enExample) |
| SG (1) | SG171413A1 (enExample) |
| WO (1) | WO2010068242A1 (enExample) |
| ZA (1) | ZA201103813B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104262267B9 (zh) * | 2008-03-18 | 2019-04-12 | 艾尼纳制药公司 | 用于治疗前列环素(pgi2)受体相关病症的pgi2受体调节剂 |
| US20110224262A1 (en) | 2008-11-26 | 2011-09-15 | Arena Pharmaceuticals, Inc. | Pyrazolyl substituted carbonic acid derivatives as modulators of the prostacyclin (pgi2) receptor useful for the treatment of disorders related thereto |
| PL2370413T3 (pl) | 2008-12-08 | 2016-01-29 | Arena Pharm Inc | Modulatory receptora prostacykliny (PGI2) użyteczne w leczeniu zaburzeń z nimi związanych |
| TWI576371B (zh) | 2011-09-30 | 2017-04-01 | 日本化成股份有限公司 | 聚合性無機粒子分散劑，含有該聚合性無機粒子分散劑之無機有機複合粒子及無機有機樹脂複合材 |
| CA2851142A1 (en) | 2011-10-06 | 2013-04-11 | Bayer Intellectual Property Gmbh | Heterocyclylpyri (mi) dinylpyrazole as fungicidals |
| WO2013050434A1 (en) | 2011-10-06 | 2013-04-11 | Bayer Intellectual Property Gmbh | Heterocyclylpyri(mi)dinylpyrazole |
| EA201790905A1 (ru) | 2014-10-23 | 2017-09-29 | Арена Фармасьютикалз, Инк. | Способ лечения состояний, связанных с рецептором pgi2 |
| KR20230021186A (ko) | 2016-11-10 | 2023-02-13 | 아레나 파마슈티칼스, 인크. | 라리네팍 및 다른 제제의 조합에 의한 pah의 치료 방법 |
| CN110582271B (zh) | 2017-03-01 | 2022-06-14 | 阿瑞那制药公司 | 包含pgi2受体激动剂的组合物及其制备方法 |
| CN111699175B (zh) | 2018-02-07 | 2022-03-29 | 南京明德新药研发有限公司 | 前列环素受体受体激动剂 |
| EP3796902A1 (en) | 2018-05-16 | 2021-03-31 | Arena Pharmaceuticals, Inc. | Compositions comprising pgi2-receptor agonists and processes for the preparation thereof |
| WO2023158634A1 (en) | 2022-02-15 | 2023-08-24 | United Therapeutics Corporation | Crystalline prostacyclin (ip) receptor agonist and uses thereof |
| KR20250099113A (ko) | 2022-09-09 | 2025-07-01 | 이노보 테라퓨틱스 인코포레이티드 | CK1α 및 DUAL CK1α/GSPT1 분해 화합물 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1021451A (en) | 1911-04-22 | 1912-03-26 | James F Craven | Receptacle for containing and discharging semisolid and pasty substances. |
| DE2945530A1 (de) | 1979-11-10 | 1981-06-04 | Chemische Werke Hüls AG, 4370 Marl | Harnstoffe mit cyclischen substituenten, ihre herstellung und verwendung als herbizide |
| JPH03160438A (ja) | 1989-11-20 | 1991-07-10 | Konica Corp | ハロゲン化銀カラー写真感光材料 |
| EP0442448A3 (en) | 1990-02-13 | 1992-08-12 | Bristol-Myers Squibb Company | Heterocyclic carboxylic acids and esters |
| CA2085844A1 (en) * | 1991-12-27 | 1993-06-28 | Nobuyuki Hamanaka | Fused benzeneoxyacetic acid derivatives |
| JPH06329598A (ja) | 1993-05-19 | 1994-11-29 | Daicel Chem Ind Ltd | エステルの製造方法 |
| DE4318889A1 (de) | 1993-06-07 | 1994-12-08 | Bayer Ag | Verfahren zur Herstellung von organischen Carbamaten |
| JP3160438B2 (ja) | 1993-09-29 | 2001-04-25 | 株式会社東芝 | 交通流予測装置 |
| JPH11269138A (ja) | 1998-03-20 | 1999-10-05 | Mitsubishi Paper Mills Ltd | 有機塩基発生剤 |
| GB9908934D0 (en) * | 1999-04-19 | 1999-06-16 | Rolic Ag | Liquid crystalline compounds |
| EP1046631A1 (en) | 1999-04-19 | 2000-10-25 | Rolic AG | Liquid crystalline compounds |
| US20040048844A1 (en) * | 1999-10-20 | 2004-03-11 | Bristol-Myers Squibb Pharma Company | Acylsemicarbazides as cyclin dependent kinase inhibitors useful as anti-cancer and anti-proliferative agents |
| WO2002055484A1 (en) | 2001-01-12 | 2002-07-18 | Takeda Chemical Industries, Ltd. | Biaryl compound, process for producing the same, and agent |
| WO2003007888A2 (en) * | 2001-07-20 | 2003-01-30 | Adipogenix, Inc. | Fat accumulation-modulating compounds |
| PL368129A1 (en) * | 2001-08-09 | 2005-03-21 | Ono Pharmaceutical Co, Ltd. | Carboxylic acid derivative compounds and drugs comprising these compounds as the active ingredient |
| TW200307539A (en) * | 2002-02-01 | 2003-12-16 | Bristol Myers Squibb Co | Cycloalkyl inhibitors of potassium channel function |
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| JP4675318B2 (ja) * | 2003-02-10 | 2011-04-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｎ−アリールカルバミン酸エステルとハロ−ヘテロアリールとを反応させることによるｎ−ヘテロアリール−ｎ−アリール−アミンの調製のためのプロセスおよび類似のプロセス |
| JP4402413B2 (ja) | 2003-09-29 | 2010-01-20 | 財団法人２１あおもり産業総合支援センター | Ｕ字型化合物およびこれを含む液晶組成物 |
| DE102004006785A1 (de) | 2004-02-11 | 2005-09-08 | Mayr, Herbert, Prof. Dr. | Verfahren zur CC-Bindungsknüpfung zwischen elektrophilen Substraten und TT-Verbindungen in neutralen bis basischen wässrigen oder alkoholischen Lösungsmitteln ohne den Einsatz einer Lewis- oder Protonensäure |
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| JP2007161867A (ja) | 2005-12-14 | 2007-06-28 | Toyo Ink Mfg Co Ltd | インキ組成物 |
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| JP7343478B2 (ja) | 2017-08-07 | 2023-09-12 | アレーナ ファーマシューティカルズ，インク． | 処置の方法 |
-
2009
- 2009-11-24 US US13/131,203 patent/US20110224262A1/en not_active Abandoned
- 2009-11-24 JP JP2011538598A patent/JP5603343B2/ja active Active
- 2009-11-24 MX MX2011005577A patent/MX2011005577A/es active IP Right Grant
- 2009-11-24 EP EP09768563A patent/EP2367797A1/en not_active Withdrawn
- 2009-11-24 BR BRPI0921369A patent/BRPI0921369B8/pt active IP Right Grant
- 2009-11-24 WO PCT/US2009/006251 patent/WO2010068242A1/en not_active Ceased
- 2009-11-24 AU AU2009325117A patent/AU2009325117C1/en active Active
- 2009-11-24 CA CA2744124A patent/CA2744124C/en active Active
- 2009-11-24 EA EA201100846A patent/EA022799B1/ru not_active IP Right Cessation
- 2009-11-24 EP EP17183750.3A patent/EP3342767B1/en active Active
- 2009-11-24 CN CN200980155333.9A patent/CN102292321B/zh active Active
- 2009-11-24 SG SG2011037926A patent/SG171413A1/en unknown
- 2009-11-24 NZ NZ593002A patent/NZ593002A/xx unknown
- 2009-11-24 KR KR1020117014566A patent/KR101707247B1/ko active Active
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2011
- 2011-05-17 IL IL212966A patent/IL212966A/en active IP Right Grant
- 2011-05-24 ZA ZA2011/03813A patent/ZA201103813B/en unknown
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2013
- 2013-07-03 US US13/934,439 patent/US9012478B2/en active Active
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2015
- 2015-03-16 US US14/659,293 patent/US9663500B2/en active Active
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- 2017-04-13 US US15/486,600 patent/US10214518B2/en active Active
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2018
- 2018-11-06 US US16/181,457 patent/US10689372B2/en active Active
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2020
- 2020-04-30 US US16/863,625 patent/US11098034B2/en active Active
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