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 (OSRAM) | 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 (OSRAM) |
| EP (2) | EP3342767B1 (OSRAM) |
| JP (1) | JP5603343B2 (OSRAM) |
| KR (1) | KR101707247B1 (OSRAM) |
| CN (1) | CN102292321B (OSRAM) |
| AU (1) | AU2009325117C1 (OSRAM) |
| BR (1) | BRPI0921369B8 (OSRAM) |
| CA (1) | CA2744124C (OSRAM) |
| EA (1) | EA022799B1 (OSRAM) |
| IL (1) | IL212966A (OSRAM) |
| MX (1) | MX2011005577A (OSRAM) |
| NZ (1) | NZ593002A (OSRAM) |
| SG (1) | SG171413A1 (OSRAM) |
| WO (1) | WO2010068242A1 (OSRAM) |
| ZA (1) | ZA201103813B (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220031743A (ko) | 2008-03-18 | 2022-03-11 | 아레나 파마슈티칼스, 인크. | 프로스타시클린 （ｐｇｉ２） 수용체와 관련된 장애의 치료에 유용한 상기 수용체의 조절제 |
| BRPI0921369B8 (pt) | 2008-11-26 | 2021-05-25 | Arena Pharm Inc | composto modulador do receptor de prostaciclina (pgi2), sua composição, sua composição farmacêutica, seus usos, bem como processos para a preparação das referidas composições |
| ES2548882T3 (es) | 2008-12-08 | 2015-10-21 | Arena Pharmaceuticals, Inc. | Moduladores del receptor de prostaciclina (PGl2) útiles para el tratamiento de trastornos relacionados con los mismos |
| JP6438199B2 (ja) | 2011-09-30 | 2018-12-12 | 三菱ケミカル株式会社 | 重合性無機粒子分散剤、該重合性無機粒子分散剤を含む無機有機複合粒子、および無機有機樹脂複合材 |
| EP2763987B1 (en) | 2011-10-06 | 2018-07-18 | Bayer CropScience AG | Heterocyclylpyri(mi)dinylpyrazole as fungicidals |
| UA114410C2 (uk) | 2011-10-06 | 2017-06-12 | Байєр Інтеллектуал Проперті Гмбх | Гетероциклілпіри(mi)динілпіразол |
| NZ731751A (en) | 2014-10-23 | 2023-07-28 | Arena Pharm Inc | Method of treating conditions related to the pgi2 receptor |
| AU2017357759A1 (en) | 2016-11-10 | 2019-06-06 | Arena Pharmaceuticals, Inc. | Methods of treating PAH with combinations of ralinepag and other agents |
| KR102432505B1 (ko) | 2017-03-01 | 2022-08-12 | 아레나 파마슈티칼스, 인크. | Pgi2-수용체 효능제를 포함하는 조성물 및 그의 제조 방법 |
| US11299475B2 (en) | 2018-02-07 | 2022-04-12 | Medshine Discovery Inc. | Prostacyclin receptor agonist |
| WO2019222764A1 (en) | 2018-05-16 | 2019-11-21 | 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 |
| CA3267079A1 (en) | 2022-09-09 | 2024-03-14 | Innovo Therapeutics, Inc. | CK1α AND DOUBLE CK1α/GSPT1 DEGRADATION COMPOUNDS |
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 |
| CA2036192A1 (en) | 1990-02-13 | 1991-08-14 | Nicholas Meanwell | 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 |
| EP1046631A1 (en) | 1999-04-19 | 2000-10-25 | Rolic AG | Liquid crystalline compounds |
| GB9908934D0 (en) * | 1999-04-19 | 1999-06-16 | 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 |
| US20030144350A1 (en) * | 2001-07-20 | 2003-07-31 | Adipogenix, Inc. | Fat accumulation-modulation compounds |
| EP1431267A4 (en) * | 2001-08-09 | 2004-12-22 | Ono Pharmaceutical Co | COMPOUNDS DERIVED FROM CARBOXYLIC ACID AND MEDICAMENTS COMPRISING SUCH COMPOUNDS AS ACTIVE INGREDIENT |
| TW200307539A (en) * | 2002-02-01 | 2003-12-16 | Bristol Myers Squibb Co | Cycloalkyl inhibitors of potassium channel function |
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| CN101723891A (zh) * | 2003-02-10 | 2010-06-09 | 沃泰克斯药物股份有限公司 | 通过使n-芳基氨基甲酸酯与卤代杂芳基反应制备n-杂芳基-n-芳基胺的方法和类似方法 |
| 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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- 2009-11-24 BR BRPI0921369A patent/BRPI0921369B8/pt active IP Right Grant
- 2009-11-24 EP EP17183750.3A patent/EP3342767B1/en active Active
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- 2009-11-24 CN CN200980155333.9A patent/CN102292321B/zh active Active
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