SK18822000A3 - Bifenylsulfónamidy ako duálne antagonisty angiotenzínového a endotelínového receptora - Google Patents

Bifenylsulfónamidy ako duálne antagonisty angiotenzínového a endotelínového receptora Download PDF

Info

Publication number: SK18822000A3
Authority: SK; Slovakia
Prior art keywords: methyl; dimethyl; biphenyl; isoxazolyl; oxo
Prior art date: 1998-07-06

Application number

SK1882-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Natesan Murugesan

John E. Tellew

John E. Macor

Zhengxiang Gu

Original Assignee

Bristol-Myers Squibb Company

Priority date (The priority date 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 date listed.)

1998-07-06

Filing date

1999-07-01

Publication date

2001-12-03

1999-07-01 Application filed by Bristol-Myers Squibb Company filed Critical Bristol-Myers Squibb Company

2001-12-03 Publication of SK18822000A3 publication Critical patent/SK18822000A3/sk

Links

SBXDENYROQKXBE-UHFFFAOYSA-N 2-phenylbenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 SBXDENYROQKXBE-UHFFFAOYSA-N 0.000 title claims abstract description 62
229940118365 Endothelin receptor antagonist Drugs 0.000 title claims abstract description 6
239000002308 endothelin receptor antagonist Substances 0.000 title claims abstract description 5
102000015427 Angiotensins Human genes 0.000 title claims description 4
230000009977 dual effect Effects 0.000 title claims description 4
108010064733 Angiotensins Proteins 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 417
238000000034 method Methods 0.000 claims abstract description 59
238000011282 treatment Methods 0.000 claims abstract description 29
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
201000010099 disease Diseases 0.000 claims abstract description 12
206010020772 Hypertension Diseases 0.000 claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
-1 cyano, hydroxy Chemical group 0.000 claims description 656
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 648
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 240
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 221
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 217
229940124530 sulfonamide Drugs 0.000 claims description 163
235000010290 biphenyl Nutrition 0.000 claims description 107
125000000217 alkyl group Chemical group 0.000 claims description 106
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 102
239000001257 hydrogen Substances 0.000 claims description 69
229910052739 hydrogen Inorganic materials 0.000 claims description 69
125000000753 cycloalkyl group Chemical group 0.000 claims description 66
239000004305 biphenyl Substances 0.000 claims description 62
150000002431 hydrogen Chemical class 0.000 claims description 55
125000003545 alkoxy group Chemical group 0.000 claims description 40
229910052736 halogen Inorganic materials 0.000 claims description 40
150000002367 halogens Chemical class 0.000 claims description 40
229910052757 nitrogen Inorganic materials 0.000 claims description 40
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 34
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 30
125000000623 heterocyclic group Chemical group 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 26
239000000460 chlorine Substances 0.000 claims description 26
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
125000001188 haloalkyl group Chemical group 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 19
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 16
229950006323 angiotensin ii Drugs 0.000 claims description 14
230000001419 dependent effect Effects 0.000 claims description 14
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 13
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 12
125000001072 heteroaryl group Chemical group 0.000 claims description 12
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
238000005859 coupling reaction Methods 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 11
102000005862 Angiotensin II Human genes 0.000 claims description 10
101800000733 Angiotensin-2 Proteins 0.000 claims description 10
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims description 10
230000008878 coupling Effects 0.000 claims description 10
238000010168 coupling process Methods 0.000 claims description 10
ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims description 10
125000000842 isoxazolyl group Chemical group 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
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 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
108050009340 Endothelin Proteins 0.000 claims description 7
102000002045 Endothelin Human genes 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 7
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 7
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
230000003213 activating effect Effects 0.000 claims description 5
239000005557 antagonist Substances 0.000 claims description 5
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 5
239000004327 boric acid Substances 0.000 claims description 5
238000006268 reductive amination reaction Methods 0.000 claims description 5
125000003831 tetrazolyl group Chemical group 0.000 claims description 5
125000001425 triazolyl group Chemical group 0.000 claims description 5
229960004295 valine Drugs 0.000 claims description 5
125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
102000005962 receptors Human genes 0.000 claims description 4
108020003175 receptors Proteins 0.000 claims description 4
102000010180 Endothelin receptor Human genes 0.000 claims description 3
108050001739 Endothelin receptor Proteins 0.000 claims description 3
206010019280 Heart failures Diseases 0.000 claims description 3
206010028980 Neoplasm Diseases 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
230000001434 glomerular Effects 0.000 claims description 3
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
108050000824 Angiotensin II receptor Proteins 0.000 claims description 2
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
208000037487 Endotoxemia Diseases 0.000 claims description 2
208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 claims description 2
208000019695 Migraine disease Diseases 0.000 claims description 2
238000006751 Mitsunobu reaction Methods 0.000 claims description 2
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 2
208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims description 2
230000001154 acute effect Effects 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
230000010261 cell growth Effects 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
210000003904 glomerular cell Anatomy 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
210000003584 mesangial cell Anatomy 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
206010027599 migraine Diseases 0.000 claims description 2
125000002524 organometallic group Chemical group 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
201000008312 primary pulmonary hypertension Diseases 0.000 claims description 2
208000002815 pulmonary hypertension Diseases 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 10
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 8
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 5
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims 4
BVMPUMOVVHLNNM-UHFFFAOYSA-N CCCC1=NC=C(C(=O)NC)N1 Chemical compound CCCC1=NC=C(C(=O)NC)N1 BVMPUMOVVHLNNM-UHFFFAOYSA-N 0.000 claims 3
238000002623 insulin potentiation therapy Methods 0.000 claims 3
150000004702 methyl esters Chemical class 0.000 claims 3
IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 3
239000004474 valine Substances 0.000 claims 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 claims 2
KFAWBGWQMXOFHN-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylic acid Chemical compound CCC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C KFAWBGWQMXOFHN-UHFFFAOYSA-N 0.000 claims 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims 2
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
VJPHAMJNGICSLT-UHFFFAOYSA-N n-methylcyclohexanecarboxamide Chemical compound CNC(=O)C1CCCCC1 VJPHAMJNGICSLT-UHFFFAOYSA-N 0.000 claims 2
229910052754 neon Inorganic materials 0.000 claims 2
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims 2
125000006002 1,1-difluoroethyl group Chemical group 0.000 claims 1
HUCFUMWLYMWWHX-UHFFFAOYSA-N 1-(2-ethoxyethyl)-2-phenylbenzene Chemical compound CCOCCC1=CC=CC=C1C1=CC=CC=C1 HUCFUMWLYMWWHX-UHFFFAOYSA-N 0.000 claims 1
IUQJWQFIHVXYIY-UHFFFAOYSA-N 1-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-1,3,3-trimethylurea Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)N(C)C)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 IUQJWQFIHVXYIY-UHFFFAOYSA-N 0.000 claims 1
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 1
DFIFVMZOFMQSAG-UHFFFAOYSA-N 1-tert-butyl-3-methylurea Chemical compound CNC(=O)NC(C)(C)C DFIFVMZOFMQSAG-UHFFFAOYSA-N 0.000 claims 1
VVQNAFBGAWCMLU-UHFFFAOYSA-N 1h-benzimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1N=CN2 VVQNAFBGAWCMLU-UHFFFAOYSA-N 0.000 claims 1
KMLXIQFZZZWADQ-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-methylacetamide Chemical compound CNC(=O)CC1=CC=CC=C1F KMLXIQFZZZWADQ-UHFFFAOYSA-N 0.000 claims 1
YWPABLWXCWUIIT-UHFFFAOYSA-N 2-(2-phenylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C1=CC=CC=C1 YWPABLWXCWUIIT-UHFFFAOYSA-N 0.000 claims 1
SOCXXLMIWNNNRI-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-formylphenyl]-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O=C1N(CC=2C=C(C=O)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C(CCCC)=NC21CCCC2 SOCXXLMIWNNNRI-UHFFFAOYSA-N 0.000 claims 1
JMCQGPBILKTSCM-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenyl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)-N-methylbenzenesulfonamide Chemical compound CN(S(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2(C1=O)CCCC2)CCCC)C2=C(C(=NO2)C)C JMCQGPBILKTSCM-UHFFFAOYSA-N 0.000 claims 1
HDRDIUYQWRKIFA-UHFFFAOYSA-N 2-[4-[(5-acetyl-4-chloro-2-propylimidazol-1-yl)methyl]phenyl]-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CCCC1=NC(Cl)=C(C(C)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=C1 HDRDIUYQWRKIFA-UHFFFAOYSA-N 0.000 claims 1
MYLVIZOINRBDHQ-UHFFFAOYSA-N 2-[4-[(5-acetyl-4-chloro-2-propylimidazol-1-yl)methyl]phenyl]-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound CCCC1=NC(Cl)=C(C(C)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 MYLVIZOINRBDHQ-UHFFFAOYSA-N 0.000 claims 1
ZBTYPUFFEQGRMY-UHFFFAOYSA-N 2-[5-[[1-(3,4-dimethyl-1,2-oxazol-5-yl)-3-methoxy-2,6-dimethyl-2H-pyridin-4-yl]oxymethyl]-2-phenylphenyl]propan-2-ol Chemical compound CC1=NOC(=C1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)C(C)(C)O)OC)C ZBTYPUFFEQGRMY-UHFFFAOYSA-N 0.000 claims 1
UAWDIKMZFDCXTF-UHFFFAOYSA-N 2-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl-propylamino]-n-methylpyridine-3-carboxamide Chemical compound N=1C=CC=C(C(=O)NC)C=1N(CCC)CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C UAWDIKMZFDCXTF-UHFFFAOYSA-N 0.000 claims 1
HHFRYVABFZFNOV-UHFFFAOYSA-N 2-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl-propylamino]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1N(CCC)CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C HHFRYVABFZFNOV-UHFFFAOYSA-N 0.000 claims 1
IKCHHLCRTPLOAT-UHFFFAOYSA-N 2-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl-propylamino]-n-methylpyridine-3-carboxamide Chemical compound N=1C=CC=C(C(=O)NC)C=1N(CCC)CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C IKCHHLCRTPLOAT-UHFFFAOYSA-N 0.000 claims 1
OKCRUZOIERYSRO-UHFFFAOYSA-N 2-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl-propylamino]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1N(CCC)CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C OKCRUZOIERYSRO-UHFFFAOYSA-N 0.000 claims 1
KSOOVOZETWHNBV-UHFFFAOYSA-N 2-butyl-5-chloro-3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]imidazole-4-carboxamide Chemical compound CCCCC1=NC(Cl)=C(C(N)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=C1 KSOOVOZETWHNBV-UHFFFAOYSA-N 0.000 claims 1
UQZPGHOJMQTOHB-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-ethylethanamine Chemical compound ClCCN(CC)CCCl UQZPGHOJMQTOHB-UHFFFAOYSA-N 0.000 claims 1
VMJFQIFIWGEWTI-UHFFFAOYSA-N 2-ethoxy-n-methylacetamide Chemical compound CCOCC(=O)NC VMJFQIFIWGEWTI-UHFFFAOYSA-N 0.000 claims 1
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 claims 1
CEHAQIOELBVSCR-UHFFFAOYSA-N 3,4-dimethyl-5-[2-methyl-4-[(4-phenylphenyl)methoxy]-2H-quinolin-1-yl]-1,2-oxazole Chemical compound CC1=NOC(=C1C)N1C(C=C(C2=CC=CC=C12)OCC1=CC=C(C=C1)C1=CC=CC=C1)C CEHAQIOELBVSCR-UHFFFAOYSA-N 0.000 claims 1
KVPZXQZKQUXLKE-UHFFFAOYSA-N 3,4-dimethyl-5-[4-[(4-phenylphenyl)methoxy]-2-propyl-2H-quinolin-1-yl]-1,2-oxazole Chemical compound CC1=NOC(=C1C)N1C(C=C(C2=CC=CC=C12)OCC1=CC=C(C=C1)C1=CC=CC=C1)CCC KVPZXQZKQUXLKE-UHFFFAOYSA-N 0.000 claims 1
UKSZVUZCXBMFSI-UHFFFAOYSA-N 3-[2-ethyl-4-[(4-phenylphenyl)methoxy]-2H-quinolin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC=1C)N1C(C=C(C2=CC=CC=C12)OCC1=CC=C(C=C1)C1=CC=CC=C1)CC UKSZVUZCXBMFSI-UHFFFAOYSA-N 0.000 claims 1
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KSRWGFLROQLABM-UHFFFAOYSA-N 5-chloro-3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-n,n-dimethyl-2-propylimidazole-4-carboxamide Chemical compound CCCC1=NC(Cl)=C(C(=O)N(C)C)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 KSRWGFLROQLABM-UHFFFAOYSA-N 0.000 claims 1
208000009304 Acute Kidney Injury Diseases 0.000 claims 1
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LQVXSNNAFNGRAH-QHCPKHFHSA-N BMS-754807 Chemical compound C([C@@]1(C)C(=O)NC=2C=NC(F)=CC=2)CCN1C(=NN1C=CC=C11)N=C1NC(=NN1)C=C1C1CC1 LQVXSNNAFNGRAH-QHCPKHFHSA-N 0.000 claims 1
JMLNSGPIDMRXBH-UHFFFAOYSA-N C(#N)C1=C(C=CC(=C1)CN1C(N(C=2C1=NC(=CC2C)C)C2=NOC(=C2C)C)CC)C2=CC=CC=C2 Chemical compound C(#N)C1=C(C=CC(=C1)CN1C(N(C=2C1=NC(=CC2C)C)C2=NOC(=C2C)C)CC)C2=CC=CC=C2 JMLNSGPIDMRXBH-UHFFFAOYSA-N 0.000 claims 1
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FOUMEFIGHWVIHA-UHFFFAOYSA-N CC=1C(=NOC1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)C(C)O)OC)C Chemical compound CC=1C(=NOC1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)C(C)O)OC)C FOUMEFIGHWVIHA-UHFFFAOYSA-N 0.000 claims 1
208000010228 Erectile Dysfunction Diseases 0.000 claims 1
206010057671 Female sexual dysfunction Diseases 0.000 claims 1
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206010057672 Male sexual dysfunction Diseases 0.000 claims 1
LFNFSTUGVCIHMP-UHFFFAOYSA-N N-[[5-[(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)methyl]-2-phenylphenyl]methyl]-3,4-dimethyl-N-(2,2,2-trifluoroethyl)-1,2-oxazol-5-amine Chemical compound CC1=NOC(=C1C)N(CC(F)(F)F)CC1=C(C=CC(=C1)CN1C(=NC=2C1=NC(=CC2C)C)CC)C2=CC=CC=C2 LFNFSTUGVCIHMP-UHFFFAOYSA-N 0.000 claims 1
ZYVXHFWBYUDDBM-UHFFFAOYSA-N N-methylnicotinamide Chemical compound CNC(=O)C1=CC=CN=C1 ZYVXHFWBYUDDBM-UHFFFAOYSA-N 0.000 claims 1
208000033626 Renal failure acute Diseases 0.000 claims 1
201000011040 acute kidney failure Diseases 0.000 claims 1
208000012998 acute renal failure Diseases 0.000 claims 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
150000001450 anions Chemical class 0.000 claims 1
208000006673 asthma Diseases 0.000 claims 1
125000003943 azolyl group Chemical group 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
150000003857 carboxamides Chemical class 0.000 claims 1
208000020832 chronic kidney disease Diseases 0.000 claims 1
208000022831 chronic renal failure syndrome Diseases 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
201000001881 impotence Diseases 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
208000028867 ischemia Diseases 0.000 claims 1
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GVWNBDVESBUDMO-UHFFFAOYSA-N methyl 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylate Chemical compound CCOC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C GVWNBDVESBUDMO-UHFFFAOYSA-N 0.000 claims 1
ISWGXOAQVXWQGY-UHFFFAOYSA-N methyl 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylate Chemical compound CCC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C ISWGXOAQVXWQGY-UHFFFAOYSA-N 0.000 claims 1
XZMWDKAPFHAOTO-UHFFFAOYSA-N methyl 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylate Chemical compound CCOC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C XZMWDKAPFHAOTO-UHFFFAOYSA-N 0.000 claims 1
RMZNWYKHMAIJSL-UHFFFAOYSA-N methyl 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylate Chemical compound CCC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C RMZNWYKHMAIJSL-UHFFFAOYSA-N 0.000 claims 1
XLCKUSNCRBAKDZ-UHFFFAOYSA-N methyl 5-chloro-3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-propylimidazole-4-carboxylate Chemical compound CCCC1=NC(Cl)=C(C(=O)OC)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=C1 XLCKUSNCRBAKDZ-UHFFFAOYSA-N 0.000 claims 1
ZEKHOXWSBSVRSS-UHFFFAOYSA-N methyl 5-chloro-3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-propylimidazole-4-carboxylate Chemical compound CCCC1=NC(Cl)=C(C(=O)OC)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 ZEKHOXWSBSVRSS-UHFFFAOYSA-N 0.000 claims 1
IXHFNEAFAWRVCF-UHFFFAOYSA-N n,2-dimethylpropanamide Chemical compound CNC(=O)C(C)C IXHFNEAFAWRVCF-UHFFFAOYSA-N 0.000 claims 1
LCBUKYAWTHUQAL-UHFFFAOYSA-N n-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]-2-phenylacetamide Chemical compound O=C1N(CC=2C=C(NC(=O)CC=3C=CC=CC=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 LCBUKYAWTHUQAL-UHFFFAOYSA-N 0.000 claims 1
WTRFAYFYRSWSBW-UHFFFAOYSA-N n-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]-3,3-dimethylbutanamide Chemical compound O=C1N(CC=2C=C(NC(=O)CC(C)(C)C)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 WTRFAYFYRSWSBW-UHFFFAOYSA-N 0.000 claims 1
MCUZSXMMBJTAAW-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-(3-fluorophenyl)-n-methylacetamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)CC=3C=C(F)C=CC=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 MCUZSXMMBJTAAW-UHFFFAOYSA-N 0.000 claims 1
LVOJCGUTVDKPLD-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-cyclohexyl-n-methylacetamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)CC3CCCCC3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 LVOJCGUTVDKPLD-UHFFFAOYSA-N 0.000 claims 1
TYSUXAPAFSSWNW-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-cyclopentyl-n-methylacetamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)CC3CCCC3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 TYSUXAPAFSSWNW-UHFFFAOYSA-N 0.000 claims 1
KERPNCCAMLATDY-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-3,5-difluoro-n-methylbenzamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)C=3C=C(F)C=C(F)C=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 KERPNCCAMLATDY-UHFFFAOYSA-N 0.000 claims 1
ADEWVTXTJJORKM-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-n-methyl-2-phenylacetamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)CC=3C=CC=CC=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 ADEWVTXTJJORKM-UHFFFAOYSA-N 0.000 claims 1
DLGRLUQYDBSOAS-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-n-methylcyclohexanecarboxamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)C3CCCCC3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 DLGRLUQYDBSOAS-UHFFFAOYSA-N 0.000 claims 1
DGFFEHWPTWDMAM-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-n-methylpyridine-2-carboxamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)C=3N=CC=CC=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 DGFFEHWPTWDMAM-UHFFFAOYSA-N 0.000 claims 1
AVRKFDAPHLNONL-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-n-methylthiadiazole-4-carboxamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)C=3N=NSC=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 AVRKFDAPHLNONL-UHFFFAOYSA-N 0.000 claims 1
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OLLZXQIFCRIRMH-UHFFFAOYSA-N n-methylbutanamide Chemical compound CCCC(=O)NC OLLZXQIFCRIRMH-UHFFFAOYSA-N 0.000 claims 1
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QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 claims 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
206010038464 renal hypertension Diseases 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
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238000007429 general method Methods 0.000 description 62
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 42
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239000002585 base Substances 0.000 description 37
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HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 22
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 21
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239000010410 layer Substances 0.000 description 21
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 18
239000012267 brine Substances 0.000 description 18
239000012044 organic layer Substances 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
239000003638 chemical reducing agent Substances 0.000 description 13
150000005232 imidazopyridines Chemical class 0.000 description 13
125000006239 protecting group Chemical group 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
125000001246 bromo group Chemical group Br* 0.000 description 12
229940079593 drug Drugs 0.000 description 12
239000003814 drug Substances 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 11
238000010511 deprotection reaction Methods 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 11
239000012071 phase Substances 0.000 description 11
238000002953 preparative HPLC Methods 0.000 description 11
229910000029 sodium carbonate Inorganic materials 0.000 description 11
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
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125000002346 iodo group Chemical group I* 0.000 description 10
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 10
230000009467 reduction Effects 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
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239000012321 sodium triacetoxyborohydride Substances 0.000 description 10
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PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Substances BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 9
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
239000012043 crude product Substances 0.000 description 9
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150000003217 pyrazoles Chemical class 0.000 description 9
150000003230 pyrimidines Chemical class 0.000 description 9
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
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125000005842 heteroatom Chemical group 0.000 description 8
239000007800 oxidant agent Substances 0.000 description 8
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
150000003222 pyridines Chemical class 0.000 description 8
230000002441 reversible effect Effects 0.000 description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
150000003934 aromatic aldehydes Chemical class 0.000 description 7
238000004108 freeze drying Methods 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
229910052744 lithium Inorganic materials 0.000 description 7
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235000019198 oils Nutrition 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
150000003141 primary amines Chemical class 0.000 description 7
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
229930186657 Lat Natural products 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
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238000005804 alkylation reaction Methods 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
238000003556 assay Methods 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 6
238000000605 extraction Methods 0.000 description 6
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
150000003951 lactams Chemical class 0.000 description 6
239000003446 ligand Substances 0.000 description 6
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 6
239000002480 mineral oil Substances 0.000 description 6
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239000002808 molecular sieve Substances 0.000 description 6
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
238000006069 Suzuki reaction reaction Methods 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
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229910052794 bromium Inorganic materials 0.000 description 5
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238000012512 characterization method Methods 0.000 description 5
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239000006185 dispersion Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
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235000019341 magnesium sulphate Nutrition 0.000 description 5
229910000403 monosodium phosphate Inorganic materials 0.000 description 5
235000019799 monosodium phosphate Nutrition 0.000 description 5
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000011135 tin Substances 0.000 description 5
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BWSDNRQVTFZQQD-AYVHNPTNSA-N phosphoramidon Chemical compound O([P@@](O)(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC=1[C]2C=CC=CC2=NC=1)C(O)=O)[C@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]1O BWSDNRQVTFZQQD-AYVHNPTNSA-N 0.000 description 1
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DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
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GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
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UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications

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- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
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SK1882-2000A 1998-07-06 1999-07-01 Bifenylsulfónamidy ako duálne antagonisty angiotenzínového a endotelínového receptora SK18822000A3 (sk)

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US9184798P	1998-07-06	1998-07-06
PCT/US1999/015063 WO2000001389A1 (en)	1998-07-06	1999-07-01	Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists

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Families Citing this family (231)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6541498B2 (en)	1993-05-20	2003-04-01	Texas Biotechnology	Benzenesulfonamides and the use thereof to modulate the activity of endothelin
BR9911621A (pt) *	1998-07-06	2001-10-16	Bristol Myers Squibb Co	Bifenil sulfonamidas como antagonista duplos de receptor de angiotensina endotelina
MY125533A (en)	1999-12-06	2006-08-30	Bristol Myers Squibb Co	Heterocyclic dihydropyrimidine compounds
EP1741713A3 (en) *	1999-12-15	2009-09-09	Bristol-Myers Squibb Company	Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists
WO2001049289A1 (en) *	1999-12-31	2001-07-12	Texas Biotechnology Corporation	Pharmaceutical and veterinary uses of endothelin antagonists
US6271228B1 (en) *	2000-04-28	2001-08-07	Pfizer Inc.	Blood pressure stabilization during hemodialysis
US7622503B2 (en)	2000-08-24	2009-11-24	University Of Tennessee Research Foundation	Selective androgen receptor modulators and methods of use thereof
AU2002226365A1 (en) *	2000-12-01	2002-06-11	Novartis Ag	Combinations of an angiotensin receptor antagonist and an anti-hypertensive drug or a statin, for the treatment of sexual dysfunction
HRP20080382A2 (en)	2001-09-21	2008-12-31	Bristol-Myers Squibb Company A Delaware (Usa) Corporation	LACTAM-CONTAINING COMPOUNDS AND DERIVATIVES THEREOF AS FACTOR Xa INHIBITORS
US7238671B2 (en)	2001-10-18	2007-07-03	Bristol-Myers Squibb Company	Human glucagon-like-peptide-1 mimics and their use in the treatment of diabetes and related conditions
AU2002348469B2 (en)	2001-10-18	2008-03-13	Bristol-Myers Squibb Company	Human glucagon-like-peptide-1 mimics and their use in the treatment of diabetes and related conditions
US8853266B2 (en)	2001-12-06	2014-10-07	University Of Tennessee Research Foundation	Selective androgen receptor modulators for treating diabetes
US6831102B2 (en)	2001-12-07	2004-12-14	Bristol-Myers Squibb Company	Phenyl naphthol ligands for thyroid hormone receptor
TWI328007B (en) *	2002-01-16	2010-08-01	Astrazeneca Ab	Novel compounds
TW200307539A (en)	2002-02-01	2003-12-16	Bristol Myers Squibb Co	Cycloalkyl inhibitors of potassium channel function
US7435824B2 (en)	2002-04-19	2008-10-14	Bristol-Myers Squibb Company	Prodrugs of potassium channel inhibitors
TW200403058A (en)	2002-04-19	2004-03-01	Bristol Myers Squibb Co	Heterocyclo inhibitors of potassium channel function
US7405234B2 (en)	2002-05-17	2008-07-29	Bristol-Myers Squibb Company	Bicyclic modulators of androgen receptor function
US7057046B2 (en)	2002-05-20	2006-06-06	Bristol-Myers Squibb Company	Lactam glycogen phosphorylase inhibitors and method of use
MY139563A (en)	2002-09-04	2009-10-30	Bristol Myers Squibb Co	Heterocyclic aromatic compounds useful as growth hormone secretagogues
ATE469645T1 (de)	2002-10-23	2010-06-15	Bristol Myers Squibb Co	Auf glycinnitril basierende hemmer der dipeptidylpeptidase iv
US7098235B2 (en)	2002-11-14	2006-08-29	Bristol-Myers Squibb Co.	Triglyceride and triglyceride-like prodrugs of glycogen phosphorylase inhibiting compounds
AU2003302084A1 (en)	2002-11-15	2004-06-15	Bristol-Myers Squibb Company	Open chain prolyl urea-related modulators of androgen receptor function
TW200504021A (en)	2003-01-24	2005-02-01	Bristol Myers Squibb Co	Substituted anilide ligands for the thyroid receptor
US7557143B2 (en)	2003-04-18	2009-07-07	Bristol-Myers Squibb Company	Thyroid receptor ligands
US6846836B2 (en)	2003-04-18	2005-01-25	Bristol-Myers Squibb Company	N-substituted phenylurea inhibitors of mitochondrial F1F0 ATP hydrolase
US6995183B2 (en)	2003-08-01	2006-02-07	Bristol Myers Squibb Company	Adamantylglycine-based inhibitors of dipeptidyl peptidase IV and methods
US7820702B2 (en)	2004-02-04	2010-10-26	Bristol-Myers Squibb Company	Sulfonylpyrrolidine modulators of androgen receptor function and method
US7378426B2 (en)	2004-03-01	2008-05-27	Bristol-Myers Squibb Company	Fused heterotricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3
US7625923B2 (en)	2004-03-04	2009-12-01	Bristol-Myers Squibb Company	Bicyclic modulators of androgen receptor function
US7696241B2 (en)	2004-03-04	2010-04-13	Bristol-Myers Squibb Company	Bicyclic compounds as modulators of androgen receptor function and method
US7772232B2 (en)	2004-04-15	2010-08-10	Bristol-Myers Squibb Company	Quinazolinyl compounds as inhibitors of potassium channel function
US7550499B2 (en)	2004-05-12	2009-06-23	Bristol-Myers Squibb Company	Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions
US9884038B2 (en)	2004-06-07	2018-02-06	University Of Tennessee Research Foundation	Selective androgen receptor modulator and methods of use thereof
US9889110B2 (en)	2004-06-07	2018-02-13	University Of Tennessee Research Foundation	Selective androgen receptor modulator for treating hormone-related conditions
TW200611704A (en)	2004-07-02	2006-04-16	Bristol Myers Squibb Co	Human glucagon-like-peptide-1 modulators and their use in the treatment of diabetes and related conditions
US7534763B2 (en)	2004-07-02	2009-05-19	Bristol-Myers Squibb Company	Sustained release GLP-1 receptor modulators
US7145040B2 (en)	2004-07-02	2006-12-05	Bristol-Myers Squibb Co.	Process for the preparation of amino acids useful in the preparation of peptide receptor modulators
US7572805B2 (en)	2004-07-14	2009-08-11	Bristol-Myers Squibb Company	Pyrrolo(oxo)isoquinolines as 5HT ligands
AR051446A1 (es)	2004-09-23	2007-01-17	Bristol Myers Squibb Co	Glucosidos de c-arilo como inhibidores selectivos de transportadores de glucosa (sglt2)
US7754755B2 (en)	2004-09-23	2010-07-13	Bristol-Myers Squibb Company	Inhibitors of 15-lipoxygenase
US7429611B2 (en)	2004-09-23	2008-09-30	Bristol-Myers Squibb Company	Indole inhibitors of 15-lipoxygenase
US7517991B2 (en)	2004-10-12	2009-04-14	Bristol-Myers Squibb Company	N-sulfonylpiperidine cannabinoid receptor 1 antagonists
US8143425B2 (en)	2004-10-12	2012-03-27	Bristol-Myers Squibb Company	Heterocyclic aromatic compounds useful as growth hormone secretagogues
AU2005299693B2 (en)	2004-10-26	2012-07-05	Janssen Pharmaceutica, N.V.	Factor Xa compounds
US7635699B2 (en)	2004-12-29	2009-12-22	Bristol-Myers Squibb Company	Azolopyrimidine-based inhibitors of dipeptidyl peptidase IV and methods
US7589088B2 (en)	2004-12-29	2009-09-15	Bristol-Myers Squibb Company	Pyrimidine-based inhibitors of dipeptidyl peptidase IV and methods
WO2006076597A1 (en)	2005-01-12	2006-07-20	Bristol-Myers Squibb Company	Bicyclic heterocycles as cannabinoid receptor modulators
US7314882B2 (en)	2005-01-12	2008-01-01	Bristol-Myers Squibb Company	Bicyclic heterocycles as cannabinoid receptor modulators
WO2006076568A2 (en)	2005-01-12	2006-07-20	Bristol-Myers Squibb Company	Thiazolopyridines as cannabinoid receptor modulators
CN101137412B (zh)	2005-01-13	2012-11-07	布里斯托尔-迈尔斯·斯奎布公司	用作凝血因子XIa抑制剂的取代的二芳基化合物
WO2006078697A1 (en)	2005-01-18	2006-07-27	Bristol-Myers Squibb Company	Bicyclic heterocycles as cannabinoid receptor modulators
US7645778B2 (en)	2005-01-19	2010-01-12	Bristol-Myers Squibb Company	Heteroaryl compounds as P2Y1 receptor inhibitors
DE602006004964D1 (de)	2005-02-10	2009-03-12	Bristol Myers Squibb Co	Dihydrochinazolinone als 5ht-modulatoren
EP2527337A1 (en)	2005-04-14	2012-11-28	Bristol-Myers Squibb Company	Inhibitors of 11-beta hydroxysteroid dehydrogenase type I
US7521557B2 (en)	2005-05-20	2009-04-21	Bristol-Myers Squibb Company	Pyrrolopyridine-based inhibitors of dipeptidyl peptidase IV and methods
US7632837B2 (en)	2005-06-17	2009-12-15	Bristol-Myers Squibb Company	Bicyclic heterocycles as cannabinoid-1 receptor modulators
US7317012B2 (en)	2005-06-17	2008-01-08	Bristol-Myers Squibb Company	Bicyclic heterocycles as cannabinoind-1 receptor modulators
US7629342B2 (en)	2005-06-17	2009-12-08	Bristol-Myers Squibb Company	Azabicyclic heterocycles as cannabinoid receptor modulators
US7452892B2 (en)	2005-06-17	2008-11-18	Bristol-Myers Squibb Company	Triazolopyrimidine cannabinoid receptor 1 antagonists
TW200726765A (en)	2005-06-17	2007-07-16	Bristol Myers Squibb Co	Triazolopyridine cannabinoid receptor 1 antagonists
WO2007002634A1 (en)	2005-06-27	2007-01-04	Bristol-Myers Squibb Company	Carbocycle and heterocycle antagonists of p2y1 receptor useful in the treatment of thrombotic conditions
AR056867A1 (es)	2005-06-27	2007-10-31	Bristol Myers Squibb Co	Antagonistas heterociclicos n- enlazados del receptor de p2y1 utiles en el tratamiento de condiciones tromboticas. composiciones farmaceuticas.
WO2007002584A1 (en)	2005-06-27	2007-01-04	Bristol-Myers Squibb Company	Linear urea mimics antagonists of p2y1 receptor useful in the treatment of thrombotic conditions
WO2007002635A2 (en)	2005-06-27	2007-01-04	Bristol-Myers Squibb Company	C-linked cyclic antagonists of p2y1 receptor useful in the treatment of thrombotic conditions
WO2007005967A2 (en) *	2005-07-05	2007-01-11	Teva Pharmaceutical Industries Ltd.	Process for preparing valsartan
EP1757290A1 (en)	2005-08-16	2007-02-28	Zentaris GmbH	Novel triazole derivatives as ghrelin analogue ligands of growth hormone secretagogue receptors
US7534804B2 (en)	2005-08-24	2009-05-19	Bristol-Myers Squibb Company	Benzoxazole inhibitors of 15-lipoxygenase
US7795436B2 (en)	2005-08-24	2010-09-14	Bristol-Myers Squibb Company	Substituted tricyclic heterocycles as serotonin receptor agonists and antagonists
JP2009506119A (ja)	2005-08-31	2009-02-12	ユニバーシティオブテネシーリサーチファウンデーション	選択的アンドロゲン受容体モジュレーターを用いる腎疾患、熱傷、創傷および脊髄損傷の処置
AR056155A1 (es)	2005-10-26	2007-09-19	Bristol Myers Squibb Co	Antagonistas del receptor 1 de la hormona de concentracion de melanina no basica
EP1943215A2 (en)	2005-10-31	2008-07-16	Brystol-Myers Squibb Company	Pyrrolidinyl beta-amino amide-based inhibitors of dipeptidyl peptidase iv and methods
US7553836B2 (en)	2006-02-06	2009-06-30	Bristol-Myers Squibb Company	Melanin concentrating hormone receptor-1 antagonists
MX2008011227A (es) *	2006-03-03	2009-02-10	Torrent Pharmaceuticals Ltd	Receptores antagonistas de accion nueva y doble en los receptores at1 y eta.
WO2007109456A2 (en) *	2006-03-16	2007-09-27	Pharmacopeia, Inc.	Substituted biphenyl isoxazole sulfonamides as dual angiotensin endothelin receptor antagonists
EP2021014A1 (en)	2006-05-26	2009-02-11	Brystol-Myers Squibb Company	Sustained release glp-1 receptor modulators
US7919598B2 (en)	2006-06-28	2011-04-05	Bristol-Myers Squibb Company	Crystal structures of SGLT2 inhibitors and processes for preparing same
EP3147278B1 (en)	2006-07-12	2020-02-12	University of Tennessee Research Foundation	Compound for treating breast cancer and progestin-dependent conditions
US7727978B2 (en)	2006-08-24	2010-06-01	Bristol-Myers Squibb Company	Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors
AU2007303056A1 (en)	2006-10-05	2008-04-10	Gilead Palo Alto, Inc.	Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl CoA desaturase inhibitors
US7960569B2 (en)	2006-10-17	2011-06-14	Bristol-Myers Squibb Company	Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions
US9604931B2 (en)	2007-01-22	2017-03-28	Gtx, Inc.	Nuclear receptor binding agents
JP5484914B2 (ja)	2007-01-22	2014-05-07	ジーティーエックス・インコーポレイテッド	核内受容体結合剤
US9623021B2 (en)	2007-01-22	2017-04-18	Gtx, Inc.	Nuclear receptor binding agents
TW200838501A (en) *	2007-02-02	2008-10-01	Theravance Inc	Dual-acting antihypertensive agents
TW200904405A (en)	2007-03-22	2009-02-01	Bristol Myers Squibb Co	Pharmaceutical formulations containing an SGLT2 inhibitor
US20080255161A1 (en) *	2007-04-11	2008-10-16	Dmitry Koltun	3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS
CN101687873A (zh)	2007-04-17	2010-03-31	百时美施贵宝公司	具有稠合杂环的11β-羟基类固醇Ⅰ型脱氢酶抑制剂
PE20090696A1 (es)	2007-04-20	2009-06-20	Bristol Myers Squibb Co	Formas cristalinas de saxagliptina y procesos para preparar las mismas
KR20100015886A (ko)	2007-04-23	2010-02-12	사노피-아벤티스	Ｐ2ｙ12 길항제로서의 퀴놀린-카복스아미드 유도체
TWI448284B (zh)	2007-04-24	2014-08-11	Theravance Inc	雙效抗高血壓劑
WO2008137435A1 (en)	2007-05-04	2008-11-13	Bristol-Myers Squibb Company	[6,6] and [6,7]-bicyclic gpr119 g protein-coupled receptor agonists
EP2152707B1 (en)	2007-05-04	2012-06-20	Bristol-Myers Squibb Company	[6,5]-bicyclic gpr119 g protein-coupled receptor agonists
TWI406850B (zh)	2007-06-05	2013-09-01	Theravance Inc	雙效苯并咪唑抗高血壓劑
US20090011994A1 (en)	2007-07-06	2009-01-08	Bristol-Myers Squibb Company	Non-basic melanin concentrating hormone receptor-1 antagonists and methods
HRP20110806T1 (hr)	2007-07-17	2011-11-30	Bristol-Myers Squibb Company	Agonisti piridon gpr119 g protein-vezanih receptora
CN101808995A (zh)	2007-07-27	2010-08-18	百时美施贵宝公司	新颖的葡糖激酶激活剂及其使用方法
WO2009035543A1 (en)	2007-09-07	2009-03-19	Theravance, Inc.	Dual-acting antihypertensive agents
US7968603B2 (en)	2007-09-11	2011-06-28	University Of Tennessee Research Foundation	Solid forms of selective androgen receptor modulators
WO2009038974A1 (en)	2007-09-20	2009-03-26	Irm Llc	Compounds and compositions as modulators of gpr119 activity
WO2009076288A1 (en)	2007-12-11	2009-06-18	Theravance, Inc.	Dual-acting benzoimidazole derivative and their use as antihypertensive agents
JP5504171B2 (ja)	2007-12-26	2014-05-28	サノフイ	Ｐ２ｙ１２アンタゴニストとしてのヘテロサイクリックピラゾール−カルボキサミド
EP2103602A1 (en)	2008-03-17	2009-09-23	AEterna Zentaris GmbH	Novel 1,2,4-triazole derivatives and process of manufacturing thereof
US7989484B2 (en)	2008-04-29	2011-08-02	Theravance, Inc.	Dual-acting antihypertensive agents
EP2300435A2 (en)	2008-05-19	2011-03-30	Schering Corporation	Heterocyclic compounds as factor ixa inhibitors
PE20091928A1 (es)	2008-05-29	2009-12-31	Bristol Myers Squibb Co	Tienopirimidinas hidroxisustituidas como antagonistas de receptor-1 de hormona concentradora de melanina no basicos
WO2009155448A1 (en) *	2008-06-20	2009-12-23	Ligand Pharmaceuticals Inc.	Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists
TW201006821A (en)	2008-07-16	2010-02-16	Bristol Myers Squibb Co	Pyridone and pyridazone analogues as GPR119 modulators
EP2334651A2 (en)	2008-07-24	2011-06-22	Theravance, Inc.	Dual-acting antihypertensive agents
US20100160322A1 (en)	2008-12-04	2010-06-24	Abbott Laboratories	Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases
US8557983B2 (en)	2008-12-04	2013-10-15	Abbvie Inc.	Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases
US8586754B2 (en)	2008-12-05	2013-11-19	Abbvie Inc.	BCL-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases
US8563735B2 (en)	2008-12-05	2013-10-22	Abbvie Inc.	Bcl-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases
AU2010225747A1 (en) *	2009-03-17	2011-11-10	Daiichi Sankyo Company,Limited	Amide derivative
JP2012522015A (ja)	2009-03-27	2012-09-20	ブリストル−マイヤーズスクイブカンパニー	Ｄｐｐ−ｉｖ阻害剤を用いて主要有害心血管事象を予防する方法
WO2010114801A1 (en)	2009-03-31	2010-10-07	Ligand Pharmaceuticals Inc.	Oral formulations of diphenylsulfonamide endothelin and angiotensin ii receptor agonists to treat elevated blood pressure and diabetic nephropathy
US9034875B2 (en)	2009-05-26	2015-05-19	Abbvie Inc.	Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases
US8546399B2 (en)	2009-05-26	2013-10-01	Abbvie Inc.	Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases
MY155645A (en) *	2009-05-26	2015-11-13	Abbvie Bahamas Ltd	Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases
US20220315555A1 (en)	2009-05-26	2022-10-06	Abbvie Inc.	Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases
SMT202000093T1 (it)	2009-06-16	2020-03-13	Pfizer	Forme di dosaggio di apixaban
EP2451782B1 (en)	2009-07-07	2016-11-09	Theravance Biopharma R&D IP, LLC	Dual-acting pyrazole antihypertensive agents
ES2441419T3 (es)	2009-07-22	2014-02-04	Theravance, Inc.	Agentes antihipertensivos de doble acción basados en oxazol
WO2011014520A2 (en)	2009-07-29	2011-02-03	Irm Llc	Compounds and compositions as modulators of gpr119 activity
WO2011017296A1 (en)	2009-08-04	2011-02-10	Schering Corporation	4, 5, 6-trisubstituted pyrimidine derivatives as factor ixa inhibitors
WO2011044001A1 (en)	2009-10-09	2011-04-14	Irm Llc	Compounds and compositions as modulators of gpr119 activity
WO2011060255A1 (en)	2009-11-13	2011-05-19	Bristol-Myers Squibb Company	Reduced mass metformin formulations
HRP20181347T1 (hr)	2009-11-13	2018-10-19	Astrazeneca Ab	Formulacije dvoslojne tablete
SI2498759T1 (sl)	2009-11-13	2018-12-31	Astrazeneca Ab	Formulacije tablet s takojšnjim sproščanjem
CN101891735B (zh) *	2009-11-25	2012-07-18	北京理工大学	联苯磺胺异噁唑类化合物、合成方法及用途
CN101921265B (zh) *	2009-11-25	2012-07-04	北京理工大学	联苯酰胺四唑类化合物、合成方法及用途
US8394858B2 (en)	2009-12-03	2013-03-12	Novartis Ag	Cyclohexane derivatives and uses thereof
WO2011090929A1 (en)	2010-01-19	2011-07-28	Theravance, Inc.	Dual-acting thiophene, pyrrole, thiazole and furan antihypertensive agents
TWI562775B (en)	2010-03-02	2016-12-21	Lexicon Pharmaceuticals Inc	Methods of using inhibitors of sodium-glucose cotransporters 1 and 2
CN102933576A (zh)	2010-04-08	2013-02-13	百时美施贵宝公司	作为gpr119调节剂的嘧啶基哌啶基氧基吡啶酮类似物
JP2013523894A (ja)	2010-04-14	2013-06-17	ブリストル−マイヤーズスクイブカンパニー	新規グルコキナーゼアクチベーターおよびその使用方法
WO2011140161A1 (en)	2010-05-06	2011-11-10	Bristol-Myers Squibb Company	Benzofuranyl analogues as gpr119 modulators
BR112012028445A2 (pt)	2010-05-06	2016-07-19	Bristol Myers Squibb Co	compostos de heteroarila bicíclica como moduladores de gpr119
US8697739B2 (en)	2010-07-29	2014-04-15	Novartis Ag	Bicyclic acetyl-CoA carboxylase inhibitors and uses thereof
EP2431035A1 (en)	2010-09-16	2012-03-21	Æterna Zentaris GmbH	Novel Triazole Derivatives with Improved Receptor Activity and Bioavailability Properties as Ghrelin Antagonists of Growth Hormone Secretagogue Receptors
UA113500C2 (xx)	2010-10-29	2017-02-10		Одержані екструзією розплаву тверді дисперсії, що містять індукуючий апоптоз засіб
KR102095698B1 (ko)	2010-10-29	2020-04-01	애브비 인코포레이티드	아폽토시스―유도제를 포함하는 고체 분산체
CA2817629C (en)	2010-11-23	2019-08-13	Abbvie Inc.	Salts and crystalline forms of an apoptosis-inducing agent
NZ708508A (en)	2010-11-23	2016-06-24	Abbvie Bahamas Ltd	Methods of treatment using selective bcl-2 inhibitors
PH12013501345A1 (en)	2010-12-23	2022-10-24	Purdue Pharma Lp	Tamper resistant solid oral dosage forms
TWI631963B (zh)	2011-01-05	2018-08-11	雷西肯製藥股份有限公司	包含鈉－葡萄糖共同輸送體１與２之抑制劑的組合物與應用方法
UA108713C2 (xx)	2011-11-11	2015-05-25		2-тіопіримідинони
KR20140137404A (ko)	2012-04-06	2014-12-02	화이자 인코포레이티드	디아실글리세롤 아실트랜스퍼라제 2 억제제
US9174965B2 (en)	2012-05-16	2015-11-03	Bristol-Myers Squibb Company	Pyrimidinylpiperidinyloxypyridone analogues as GPR119 modulators
HRP20180815T8 (hr)	2012-06-11	2019-02-08	Bristol-Myers Squibb Company	Prolijekovi fosforamidne kiseline 5-[5-fenil-4-(piridin-2-ilmetilamino)hinazolin-2-il]piridin-3-sulfonamida
US10987334B2 (en)	2012-07-13	2021-04-27	University Of Tennessee Research Foundation	Method of treating ER mutant expressing breast cancers with selective androgen receptor modulators (SARMs)
KR102122941B1 (ko)	2012-07-13	2020-06-15	지티엑스, 인코포레이티드	선택적 안드로겐 수용체 조절자(sarms)를 이용한 안드로겐 수용체(ar) 양성 유방암의 치료 방법
US10258596B2 (en)	2012-07-13	2019-04-16	Gtx, Inc.	Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS)
US9969683B2 (en)	2012-07-13	2018-05-15	Gtx, Inc.	Method of treating estrogen receptor (ER)-positive breast cancers with selective androgen receptor modulator (SARMS)
US10314807B2 (en)	2012-07-13	2019-06-11	Gtx, Inc.	Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS)
US9622992B2 (en)	2012-07-13	2017-04-18	Gtx, Inc.	Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs)
US9744149B2 (en)	2012-07-13	2017-08-29	Gtx, Inc.	Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs)
LT6043B (lt)	2012-08-27	2014-06-25	Uab "Mibarsas"	Organinės trąšos sapropelio pagrindu ir jų gamybos būdas
US9586900B2 (en)	2012-09-05	2017-03-07	Bristol-Myers Squibb Company	Pyrrolone or pyrrolidinone melanin concentrating hormone receptor-1 antagonists
EP2892897A1 (en)	2012-09-05	2015-07-15	Bristol-Myers Squibb Company	Pyrrolone or pyrrolidinone melanin concentrating hormone receptor-1 antagonists
WO2014052619A1 (en)	2012-09-27	2014-04-03	Irm Llc	Piperidine derivatives and compositions as modulators of gpr119 activity
EP3489226B1 (en)	2012-11-20	2021-02-17	Lexicon Pharmaceuticals, Inc.	Inhibitors of sodium glucose cotransporter 1
WO2014143606A1 (en)	2013-03-11	2014-09-18	Bristol-Myers Squibb Company	Pyrrolotriazines as potassium ion channel inhibitors
US9242966B2 (en)	2013-03-11	2016-01-26	Bristol-Myers Squibb Company	Phthalazines as potassium ion channel inhibitors
US9050345B2 (en)	2013-03-11	2015-06-09	Bristol-Myers Squibb Company	Pyrrolotriazines as potassium ion channel inhibitors
JP6386527B2 (ja)	2013-03-11	2018-09-05	ブリストル−マイヤーズスクイブカンパニーＢｒｉｓｔｏｌ−ＭｙｅｒｓＳｑｕｉｂｂＣｏｍｐａｎｙ	カリウムイオンチャネル阻害剤としてのピロロピリダジン
JP2016516691A (ja)	2013-03-11	2016-06-09	ブリストル−マイヤーズスクイブカンパニーＢｒｉｓｔｏｌ−ＭｙｅｒｓＳｑｕｉｂｂＣｏｍｐａｎｙ	カリウムイオンチャネル阻害剤としてのイソキノリン
US20140275082A1 (en)	2013-03-14	2014-09-18	Abbvie Inc.	Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases
KR102230461B1 (ko)	2013-03-15	2021-03-22	유니버시티 오브 써던 캘리포니아	엔지오텐신-관련 질환들의 치료를 위한 방법들, 화합물들 및 조성물들
JP6348582B2 (ja)	2013-10-09	2018-06-27	ファイザー・インク	プロスタグランジンｅｐ３受容体の拮抗薬
WO2015061272A1 (en)	2013-10-22	2015-04-30	Bristol-Myers Squibb Company	Isotopically labeled triazolopyridine 11-beta hydroxysteroid dehydrogenase type i inhibitors
MA39753B1 (fr)	2014-03-17	2018-10-31	Pfizer	Inhibiteurs de diacylglycérol acyltransférase pour le traitement de troubles métaboliques ou analogues
AP2016009514A0 (en)	2014-04-04	2016-10-31	Pfizer	Bicyclic-fused heteroaryl or aryl compounds and their use as irak4 inhibitors
EP3131897B8 (en)	2014-04-16	2022-08-03	Merck Sharp & Dohme LLC	Factor ixa inhibitors
SG11201609050UA (en)	2014-05-30	2016-12-29	Pfizer	Carbonitrile derivatives as selective androgen receptor modulators
WO2016103097A1 (en)	2014-12-22	2016-06-30	Pfizer Inc.	Antagonists of prostaglandin ep3 receptor
CN104761548B (zh) *	2015-04-27	2017-09-12	梯尔希（南京）药物研发有限公司	一种稳定同位素标记的二苯基磺酰胺类药物的制备方法
MX382097B (es)	2015-05-05	2025-03-13	Pfizer	1-(2-aminoetil)-6-(2-(2-hidroxietoxi)-5-metilfenil)-2-tioxo-2,3-dihidropirimidin-4(1h)-ona, y el uso del mismo para tratar afecciones cardiovasculares.
JP2018516254A (ja)	2015-05-29	2018-06-21	ファイザー・インク	バニン１酵素の阻害薬としての新規なヘテロ環化合物
HUE051898T2 (hu)	2015-06-17	2021-03-29	Pfizer	Triciklusos vegyületek és alkalmazásuk foszfodiészteráz inhibitorokként
WO2016203335A1 (en)	2015-06-18	2016-12-22	Pfizer Inc.	Novel pyrido[2,3-b]pyrazinones as bet-family bromodomain inhibitors
BR112018002071A2 (pt)	2015-08-13	2018-09-18	Pfizer	compostos heteroarílicos ou arílicos fundidos bicíclicos
LT3341367T (lt)	2015-08-27	2021-04-26	Pfizer Inc.	Biciklinis sulietas heteroarilas arba arilo junginiai kaip irak4 moduliatoriai
WO2017037567A1 (en)	2015-09-03	2017-03-09	Pfizer Inc.	Regulators of frataxin
CN105481844A (zh) *	2015-12-08	2016-04-13	梁彦云	一种治疗高血压的药物组合物
PT3397631T (pt)	2015-12-29	2021-05-28	Pfizer	3-azabiciclo[3.1.0]hexanos substituídos como inibidores de cetoexocinase
CN106188115A (zh) *	2016-07-13	2016-12-07	北京理工大学	廉价高效合成2‑二羟硼基‑n‑二甲异噁唑基‑n‑甲氧乙氧甲基苯磺酰胺的新方法
MX2019000536A (es)	2016-07-14	2019-04-01	Pfizer	Nuevas pirimidinas carboxamidas como inhibidores de enzima vanina-1.
MA45714A (fr)	2016-07-22	2019-05-29	Bristol Myers Squibb Co	Activateurs de glucokinase et leurs procédés d'utilisation
AR109179A1 (es)	2016-08-19	2018-11-07	Pfizer	Inhibidores de diacilglicerol aciltransferasa 2
CN117017985A (zh)	2016-10-13	2023-11-10	特拉维尔治疗公司	用于治疗肾脏疾病或病症的联苯磺酰胺化合物
US10703723B2 (en)	2017-03-09	2020-07-07	Truly Translational Sweden Ab	Prodrugs of sulfasalazine, pharmaceutical compositions thereof and their use in the treatment of autoimmune disease
US11883405B2 (en)	2017-05-31	2024-01-30	Amplio Pharma Ab	Pharmaceutical composition comprising a combination of methotrexate and novobiocin, and the use of said composition in therapy
EP3488868B1 (en)	2017-11-23	2023-09-13	medac Gesellschaft für klinische Spezialpräparate mbH	Pharmaceutical composition for oral administration containing sulfasalazine and / or a sulfasalazine organic salt, production process and use
EP3489222A1 (en)	2017-11-23	2019-05-29	medac Gesellschaft für klinische Spezialpräparate mbH	Sulfasalazine salts, production processes and uses
US11752173B2 (en)	2017-12-19	2023-09-12	Beijing Jiyuan Biological Technology Co., Ltd.	FGF21 and GLP1 double gene-modified mesenchymal stem cell and use in treating a metabolic disease
WO2019133445A1 (en)	2017-12-28	2019-07-04	Inception Ibd, Inc.	Aminothiazoles as inhibitors of vanin-1
PE20210644A1 (es)	2018-07-19	2021-03-23	Astrazeneca Ab	METODOS DE TRATAMIENTO DE HFpEF EMPLEANDO DAPAGLIFLOZINA Y COMPOSICIONES QUE COMPRENDEN LA MISMA
AU2019329884B2 (en)	2018-08-31	2022-01-27	Pfizer Inc.	Combinations for treatment of NASH/NAFLD and related diseases
CN113039176A (zh)	2018-09-26	2021-06-25	莱西肯医药有限公司	N-(1-((2-(二甲基氨基)乙基)氨基)-2-甲基-1-氧代丙-2-基)-4-(4-(2-甲基-5-((2s,3r,4r,5s,6r)-3,4,5-三羟基-6-(甲硫基)四氢-2h-吡喃-2-基)苯甲基)苯基)丁酰胺的结晶形式及其合成方法
JP7524167B2 (ja)	2018-10-04	2024-07-29	トラビアセラピューティクス，インコーポレイテッド	Ｉｖ型コラーゲン疾患の処置のためのビフェニルスルホンアミド化合物
WO2020102575A1 (en)	2018-11-16	2020-05-22	Inception Ibd, Inc.	Heterocyclic aminothiazoles and uses thereof
CN113874019A (zh)	2019-05-20	2021-12-31	辉瑞大药厂	用于治疗nash/nafld及相关疾病的包含作为glp-1r激动剂的苯并二氧杂环戊烯的组合
WO2020261144A1 (en)	2019-06-28	2020-12-30	Pfizer Inc.	5-(thiophen-2-yl)-1h-tetrazole derivatives as bckdk inhibitors useful for treating various diseases
TW202115086A (zh)	2019-06-28	2021-04-16	美商輝瑞大藥廠	Bckdk抑制劑
TWI771766B (zh)	2019-10-04	2022-07-21	美商輝瑞股份有限公司	二醯基甘油醯基轉移酶２抑制劑
EP4458834A3 (en)	2020-02-07	2025-01-15	Gasherbrum Bio, Inc.	Heterocyclic glp-1 agonists
JP2022058085A (ja)	2020-02-24	2022-04-11	ファイザー・インク	ジアシルグリセロールアシルトランスフェラーゼ２阻害剤とアセチル－ＣｏＡカルボキシラーゼ阻害剤との組合せ
ES2994968T3 (en)	2020-06-09	2025-02-04	Pfizer	Spiro compounds as melanocortin 4 receptor antagonists and uses thereof
US20220023252A1 (en)	2020-07-27	2022-01-27	Astrazeneca Ab	Methods of treating chronic kidney disease with dapagliflozin
WO2022266370A1 (en)	2021-06-17	2022-12-22	Aria Pharmaceuticals, Inc.	Sparsentan for treating idiopathic pulmonary fibrosis
WO2023275715A1 (en)	2021-06-30	2023-01-05	Pfizer Inc.	Metabolites of selective androgen receptor modulators
WO2023026180A1 (en)	2021-08-26	2023-03-02	Pfizer Inc.	Amorphous form of (s)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-n-(tetrahydrofuran-3- yl)pyrimidine-5-carboxamide
MX2024002411A (es) *	2021-08-26	2024-04-05	Shanghai Hansoh Biomedical Co Ltd	Antagonista biológico que contiene anillos aromáticos, y método para su preparación y su uso.
CN118119617A (zh) *	2021-10-21	2024-05-31	年衍药业（上海）有限公司	一种双重拮抗剂及其用途
AU2022403203A1 (en)	2021-12-01	2024-05-02	Pfizer Inc.	3-phenyl-1-benzothiophene-2-carboxylic acid derivatives as branched-chain alpha keto acid dehydrogenase kinase inhibitors for the treatment of diabetes, kidney diseases, nash and heart failure
JP2024544021A (ja)	2021-12-06	2024-11-26	ファイザー・インク	メラノコルチン４受容体アンタゴニストおよびそれらの使用
US20250108065A1 (en)	2022-01-26	2025-04-03	Astrazeneca Ab	Methods of treating prediabetes or reducing the risk of developing type 2 diabetes with dapagliflozin
WO2023169456A1 (en)	2022-03-09	2023-09-14	Gasherbrum Bio , Inc.	Heterocyclic glp-1 agonists
JP2025513071A (ja)	2022-04-14	2025-04-22	ガシャーブラム・バイオ・インコーポレイテッド	ヘテロ環式ｇｌｐ－１アゴニスト
WO2023224963A1 (en) *	2022-05-16	2023-11-23	Aria Pharmaceuticals, Inc.	Dual-acting angiotensin and endothelin receptor antagonists
AU2023358062A1 (en)	2022-10-07	2025-03-20	Pfizer Inc.	Hsd17b13 inhibitors and/or degraders
US20240182468A1 (en)	2022-10-18	2024-06-06	Pfizer Inc.	Compounds for the activation of ampk
IL319392A (en)	2022-10-18	2025-05-01	Pfizer	Pectin-like phospholipase domain-containing protein 3 (PNPLA3) modification preparations
CN115745983A (zh) *	2022-11-23	2023-03-07	深圳信立泰药业股份有限公司	一种血管紧张肽和内皮肽受体拮抗剂及其应用
TW202435857A (zh)	2022-12-15	2024-09-16	美商迦舒布魯姆生物有限公司	具有glp-1促效劑活性之化合物之鹽及固體形式
AU2023393326A1 (en)	2022-12-16	2025-06-19	Pfizer Inc.	3-fluoro-4-hydroxybenzmide-containing inhibitors and/or degraders and uses thereof
TW202448876A (zh) *	2023-02-24	2024-12-16	大陸商江蘇豪森藥業集團有限公司	含芳環類衍生物拮抗劑的鹽、其製備方法和應用
WO2024214038A1 (en)	2023-04-14	2024-10-17	Pfizer Inc.	Glucose-dependent insulinotropic polypeptide receptor antagonists and uses thereof
WO2025099566A1 (en)	2023-11-08	2025-05-15	Pfizer Inc.	A crystalline form of 6-fluoro-3-(2,4,5-trifluoro-3-methoxyphenyl)-1-benzothiophene-2-carboxylic acid
LT7101B (lt)	2024-01-16	2024-10-25	Steponavičius Petras	Organinės trąšos sapropelio pagrindu ir jų gamybos būdas, panaudojant susmulkintus šiaudus, aukštapelkines durpes ir hidrogelį

Family Cites Families (41)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4880804A (en) *	1988-01-07	1989-11-14	E. I. Du Pont De Nemours And Company	Angiotensin II receptor blocking benzimidazoles
IL94390A (en) *	1989-05-30	1996-03-31	Merck & Co Inc	The 6-membered trans-nitrogen-containing heterocycles are compressed with imidazo and pharmaceutical preparations containing them
CA2020073A1 (en) *	1989-07-03	1991-01-04	Eric E. Allen	Substituted quinazolinones as angiotensin ii antagonists
US5240928A (en) *	1989-07-03	1993-08-31	Merck & Co., Inc.	Substituted quinazolinones as angiotensin II antagonists
EP0517812A4 (en)	1990-02-13	1995-10-18	Merck & Co Inc	Angiotensin ii antagonists incorporating a substituted benzyl element
DE122010000024I1 (de) *	1990-02-19	2010-07-08	Novartis Ag	Acylverbindungen
SU1724657A1 (ru)	1990-02-26	1992-04-07	Научно-Производственный Кооператив "Охрана Природы"	Способ приготовлени сапропелевого удобрени
FR2681067B1 (fr)	1991-09-10	1993-12-17	Elf Sanofi	Derives heterocycliques n-substitues, leur preparation, les compositions pharmaceutiques en contenant.
US5250548A (en) *	1990-09-10	1993-10-05	Abbott Laboratories	Angiotensin II receptor antagonists
IL99246A0 (en) *	1990-09-10	1992-07-15	Abbott Lab	Angiotensin ii receptor antagonists and pharmaceutical compositions containing them
CA2057089A1 (en)	1990-12-07	1992-06-08	Eric E. Allen	Substituted pyrazolopyrimidines and imidazopyridazines as angiotensin ii antagonists
TW274551B (es)	1991-04-16	1996-04-21	Takeda Pharm Industry Co Ltd
CA2079982A1 (en) *	1991-10-07	1993-04-08	Stephen E. De Laszlo	Substituted pyrazino (2,3-d)-pyrimidinones as angiotensin ii antagonists
US5674883A (en) *	1992-02-07	1997-10-07	Roussel Uclaf	Derivatives of pyridone, their preparation process, the new intermediates obtained, their use as medicaments and the pharmaceutical compositions containing them
WO1993017681A1 (en)	1992-03-02	1993-09-16	Abbott Laboratories	Angiotensin ii receptor antagonists
GB2264710A (en) *	1992-03-04	1993-09-08	Merck & Co Inc	Quinoline and azaquinoline angiotensin ii antagonists incorporating a substituted biphenyl element
DE4208304A1 (de) *	1992-03-16	1993-09-23	Merck Patent Gmbh	2-oxochinolinderivate
US5514696A (en) *	1992-05-06	1996-05-07	Bristol-Myers Squibb Co.	Phenyl sulfonamide endothelin antagonists
DE4300912A1 (de)	1993-01-15	1994-07-21	Merck Patent Gmbh	Chinazolinderivate
US5256658A (en)	1993-01-15	1993-10-26	Ortho Pharmaceutical Corporation	Angiotensin II inhibitors
EP0863143A1 (en)	1993-03-24	1998-09-09	American Home Products Corporation	Intermediates useful in the production of pyridopyrimidone angiotensin AII antagonists
DE4320432A1 (de)	1993-06-21	1994-12-22	Bayer Ag	Substituierte Mono- und Bipyridylmethylderivate
ZA945190B (en)	1993-07-30	1995-02-24	Kotobuki Seiyaku Co Ltd	Carboxymethylidenecycloheptimidazole derivatives method or manufacturing the same and therapeutic agents containing these compounds
US5674879A (en)	1993-09-24	1997-10-07	G.D. Searle & Co.	Compositions including and methods of using conformationally restricted angiotensin II antagonist
US5438136A (en)	1993-11-02	1995-08-01	Merck & Co., Inc.	Benzo-fused macrocycles promote release of growth hormone
RU2041866C1 (ru)	1994-01-20	1995-08-20	Акционерное предприятие "Сапропель-Неро"	Способ добычи и получения сапропелевого удобрения
US5612359A (en) *	1994-08-26	1997-03-18	Bristol-Myers Squibb Company	Substituted biphenyl isoxazole sulfonamides
FR2725987B1 (fr)	1994-10-19	1997-01-10	Sanofi Sa	Procede pour la preparation d'un derive de tetrazole sous deux formes cristallines et nouvelle forme cristalline de ce derive
IL116916A (en) *	1995-02-06	2000-09-28	Bristol Myers Squibb Co	Substituted biphenyl sulfonamide derivatives and pharmaceutical compositions containing the same
US5760038A (en) *	1995-02-06	1998-06-02	Bristol-Myers Squibb Company	Substituted biphenyl sulfonamide endothelin antagonists
EA007107B1 (ru) *	1995-04-04	2006-06-30	Инсизив Фармасьютикэлз Инк.	Тиенил- и дифенилсульфонамиды и их производные, модулирующие активность эндотелина
GB9512697D0 (en) *	1995-06-22	1995-08-23	Zeneca Ltd	Heterocyclic compounds
US5846990A (en) *	1995-07-24	1998-12-08	Bristol-Myers Squibb Co.	Substituted biphenyl isoxazole sulfonamides
CN1211183A (zh)	1996-02-20	1999-03-17	布里斯托尔-迈尔斯斯奎布公司	联苯基异噁唑磺酰胺的制备方法
WO1997033886A1 (en) *	1996-03-12	1997-09-18	Bristol-Myers Squibb Company	Substituted biphenyl isoxazole sulfonamides
US5939446A (en) *	1996-04-09	1999-08-17	Bristol-Myers Squibb Co.	Heteroaryl substituted phenyl isoxazole sulfonamide endothelin antagonists
IT1283620B1 (it)	1996-04-19	1998-04-22	Luso Farmaco Inst	"pirimidin-4-oni n-3 sostituiti ad attivita' aii antagonista"
JPH09291078A (ja)	1996-04-25	1997-11-11	Kyorin Pharmaceut Co Ltd	オルトメトキシフェニルピペラジニルアルコキシアリール基を有する新規イミダゾール誘導体及びその製造法
TW536540B (en)	1997-01-30	2003-06-11	Bristol Myers Squibb Co	Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe
US5846985A (en) *	1997-03-05	1998-12-08	Bristol-Myers Squibb Co.	Substituted biphenyl isoxazole sulfonamides
BR9911621A (pt) *	1998-07-06	2001-10-16	Bristol Myers Squibb Co	Bifenil sulfonamidas como antagonista duplos de receptor de angiotensina endotelina

1999
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- 1999-07-01 WO PCT/US1999/015063 patent/WO2000001389A1/en active Application Filing
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2001
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Also Published As

Publication number	Publication date
NO20010062D0 (no)	2001-01-05
BG65404B1 (bg)	2008-06-30
CN1149196C (zh)	2004-05-12
LT4854B (lt)	2001-11-26
JP2002519380A (ja)	2002-07-02
JP2010209096A (ja)	2010-09-24
ZA200006772B (en)	2002-02-20
AU5088899A (en)	2000-01-24
PT1094816E (pt)	2009-03-10
CZ200172A3 (cs)	2001-08-15
EE200100006A (et)	2002-06-17
HUP0104634A2 (en)	2002-10-28
PL203771B1 (pl)	2009-11-30
CN1308536A (zh)	2001-08-15
WO2000001389A1 (en)	2000-01-13
DE69940063D1 (de)	2009-01-22
LT2001004A (en)	2001-07-25
EP1094816A1 (en)	2001-05-02
CA2336714A1 (en)	2000-01-13
GEP20033114B (en)	2003-11-25
IL140622A0 (en)	2002-02-10
HUP0104634A3 (en)	2002-11-28
LV12639A (lv)	2001-04-20
ES2318899T3 (es)	2009-05-01
ID26984A (id)	2001-02-22
LT2000123A (lt)	2001-07-25
TR200100149T2 (tr)	2001-10-22
ATE416772T1 (de)	2008-12-15
RU2001103044A (ru)	2003-08-10
PL346443A1 (en)	2002-02-11
EP2002837A1 (en)	2008-12-17
PL201048B1 (pl)	2009-03-31
KR20010083092A (ko)	2001-08-31
LT4864B (lt)	2001-11-26
BG105205A (en)	2001-09-28
EP1094816B1 (en)	2008-12-10
NO20010062L (no)	2001-03-05
NZ508118A (en)	2003-07-25
DK1094816T3 (da)	2009-04-06
AU767456B2 (en)	2003-11-13
LV12639B (lv)	2001-09-20
EP1094816A4 (en)	2001-12-19
BR9911621A (pt)	2001-10-16

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