JP2020515516A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020515516A5 JP2020515516A5 JP2019537185A JP2019537185A JP2020515516A5 JP 2020515516 A5 JP2020515516 A5 JP 2020515516A5 JP 2019537185 A JP2019537185 A JP 2019537185A JP 2019537185 A JP2019537185 A JP 2019537185A JP 2020515516 A5 JP2020515516 A5 JP 2020515516A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- oxy
- chloro
- cyano
- ethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 408
- 229940124530 sulfonamide Drugs 0.000 claims description 265
- 150000003456 sulfonamides Chemical class 0.000 claims description 262
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 215
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 153
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 140
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 134
- 239000004202 carbamide Substances 0.000 claims description 125
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 124
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 122
- 125000000623 heterocyclic group Chemical group 0.000 claims description 97
- -1 3-aminopiperidine-1-yl Chemical group 0.000 claims description 83
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 83
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 229910052757 nitrogen Inorganic materials 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 38
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 229910052698 phosphorus Inorganic materials 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- 125000003114 inden-1-yl group Chemical group [H]C1=C([H])C([H])(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 15
- YSERCIHBCXZJHY-HKUYNNGSSA-N (1S,2S)-6-chloro-2-(dimethylamino)-1-(2-methylphenoxy)-2,3-dihydro-1H-indene-4-carbonitrile Chemical compound ClC1=CC(=C2C[C@@H]([C@H](C2=C1)OC1=C(C=CC=C1)C)N(C)C)C#N YSERCIHBCXZJHY-HKUYNNGSSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- MGHNDJJPPOAIHK-UHFFFAOYSA-N 1H-inden-1-yl Chemical group C1=CC=C2[CH]C=CC2=C1 MGHNDJJPPOAIHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- MMCSOJGCSIIZFZ-PMACEKPBSA-N ClC1=CC(=C2C[C@@H]([C@H](C2=C1)OC1=CC=C(C=C1)S(=O)(=O)N)N1CCNCC1)C#N Chemical compound ClC1=CC(=C2C[C@@H]([C@H](C2=C1)OC1=CC=C(C=C1)S(=O)(=O)N)N1CCNCC1)C#N MMCSOJGCSIIZFZ-PMACEKPBSA-N 0.000 claims description 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 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 3
- IQHXABCGSFAKPN-UHFFFAOYSA-N pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCNC1 IQHXABCGSFAKPN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- HOAIIKMYWZFQAN-PMACEKPBSA-N (1S,2S)-6-chloro-1-phenoxy-2-piperazin-1-yl-2,3-dihydro-1H-indene-4-carbonitrile Chemical compound ClC1=CC(=C2C[C@@H]([C@H](C2=C1)OC1=CC=CC=C1)N1CCNCC1)C#N HOAIIKMYWZFQAN-PMACEKPBSA-N 0.000 claims description 2
- UDAUYRKMSQRJDG-BMUFGRPASA-N 1-[4-[6-[[(1S,2S)-6-chloro-4-cyano-2-piperazin-1-yl-2,3-dihydro-1H-inden-1-yl]oxy]-3,4-dihydro-1H-isoquinolin-2-yl]-4-oxobutyl]-3-[4-[[4-[6-[[(1S,2S)-6-chloro-4-cyano-2-piperazin-1-yl-2,3-dihydro-1H-inden-1-yl]oxy]-3,4-dihydro-1H-isoquinolin-2-yl]-4-oxobutyl]carbamoylamino]butyl]urea Chemical compound C(CCCNC(=O)NCCCC(N1CC2=CC=C(C=C2CC1)O[C@@H]1[C@H](CC2=C(C=C(C=C12)Cl)C#N)N1CCNCC1)=O)NC(=O)NCCCC(=O)N1CC2=CC=C(C=C2CC1)O[C@@H]1[C@H](CC2=C(C=C(C=C12)Cl)C#N)N1CCNCC1 UDAUYRKMSQRJDG-BMUFGRPASA-N 0.000 claims description 2
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 2
- STRWNSXHTGIOQH-SFTDATJTSA-N CC1=CC(C#N)=C(C[C@@H]([C@H]2OC(C=C3)=CC=C3S(N)(=O)=O)N3CCNCC3)C2=C1 Chemical compound CC1=CC(C#N)=C(C[C@@H]([C@H]2OC(C=C3)=CC=C3S(N)(=O)=O)N3CCNCC3)C2=C1 STRWNSXHTGIOQH-SFTDATJTSA-N 0.000 claims description 2
- RPLHIDLAYRDZBE-CZAAIQMYSA-N N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)C#N)Cl)OC1=CC=CC=C1 Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)C#N)Cl)OC1=CC=CC=C1 RPLHIDLAYRDZBE-CZAAIQMYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000005991 hyperphosphatemia Diseases 0.000 claims 1
- 239000002694 phosphate binding agent Substances 0.000 claims 1
- 206010010774 Constipation Diseases 0.000 description 29
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- 150000001345 alkine derivatives Chemical class 0.000 description 15
- PEDPVHYNSCOTLR-UAOJZALGSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-phenoxy-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=CC=CC=C1 PEDPVHYNSCOTLR-UAOJZALGSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 208000011580 syndromic disease Diseases 0.000 description 11
- 230000001684 chronic effect Effects 0.000 description 10
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 208000020832 chronic kidney disease Diseases 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 7
- WNWOGOMGWXFMIZ-WMZOPIPTSA-N (1S,2S)-4,6-dichloro-N,N-dimethyl-1-(2-methylphenoxy)-2,3-dihydro-1H-inden-2-amine Chemical compound ClC1=C2C[C@@H]([C@H](C2=CC(=C1)Cl)OC1=C(C=CC=C1)C)N(C)C WNWOGOMGWXFMIZ-WMZOPIPTSA-N 0.000 description 6
- 201000003883 Cystic fibrosis Diseases 0.000 description 6
- 208000007530 Essential hypertension Diseases 0.000 description 6
- 208000018522 Gastrointestinal disease Diseases 0.000 description 6
- 206010019280 Heart failures Diseases 0.000 description 6
- 206010020772 Hypertension Diseases 0.000 description 6
- 208000024780 Urticaria Diseases 0.000 description 6
- 210000001072 colon Anatomy 0.000 description 6
- 208000030159 metabolic disease Diseases 0.000 description 6
- 208000015943 Coeliac disease Diseases 0.000 description 5
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 208000008589 Obesity Diseases 0.000 description 4
- 108091006649 SLC9A3 Proteins 0.000 description 4
- 102100030375 Sodium/hydrogen exchanger 3 Human genes 0.000 description 4
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 4
- 208000038016 acute inflammation Diseases 0.000 description 4
- 230000006022 acute inflammation Effects 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 208000037976 chronic inflammation Diseases 0.000 description 4
- 230000006020 chronic inflammation Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000016097 disease of metabolism Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- 208000006454 hepatitis Diseases 0.000 description 4
- 231100000283 hepatitis Toxicity 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 208000019423 liver disease Diseases 0.000 description 4
- 235000020824 obesity Nutrition 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 206010001605 Alcohol poisoning Diseases 0.000 description 3
- 201000004384 Alopecia Diseases 0.000 description 3
- 206010003645 Atopy Diseases 0.000 description 3
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 3
- 206010007559 Cardiac failure congestive Diseases 0.000 description 3
- 206010008609 Cholangitis sclerosing Diseases 0.000 description 3
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 3
- 206010009900 Colitis ulcerative Diseases 0.000 description 3
- 208000011231 Crohn disease Diseases 0.000 description 3
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 3
- 206010012742 Diarrhoea infectious Diseases 0.000 description 3
- 208000004232 Enteritis Diseases 0.000 description 3
- 208000001640 Fibromyalgia Diseases 0.000 description 3
- 206010016654 Fibrosis Diseases 0.000 description 3
- 208000004262 Food Hypersensitivity Diseases 0.000 description 3
- 206010016946 Food allergy Diseases 0.000 description 3
- 208000017228 Gastrointestinal motility disease Diseases 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 208000030053 Opioid-Induced Constipation Diseases 0.000 description 3
- 208000012868 Overgrowth Diseases 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- 208000012654 Primary biliary cholangitis Diseases 0.000 description 3
- 208000025747 Rheumatic disease Diseases 0.000 description 3
- 102100022897 Sodium/hydrogen exchanger 10 Human genes 0.000 description 3
- 201000002661 Spondylitis Diseases 0.000 description 3
- 208000007107 Stomach Ulcer Diseases 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 description 3
- 206010047115 Vasculitis Diseases 0.000 description 3
- 231100000360 alopecia Toxicity 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 230000002337 anti-port Effects 0.000 description 3
- 208000029560 autism spectrum disease Diseases 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 208000014797 chronic intestinal pseudoobstruction Diseases 0.000 description 3
- 230000007882 cirrhosis Effects 0.000 description 3
- 208000019425 cirrhosis of liver Diseases 0.000 description 3
- 208000010643 digestive system disease Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 208000001848 dysentery Diseases 0.000 description 3
- 235000020932 food allergy Nutrition 0.000 description 3
- 201000005917 gastric ulcer Diseases 0.000 description 3
- 208000018685 gastrointestinal system disease Diseases 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 208000007386 hepatic encephalopathy Diseases 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 208000017169 kidney disease Diseases 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 201000006417 multiple sclerosis Diseases 0.000 description 3
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 3
- 230000002956 necrotizing effect Effects 0.000 description 3
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 3
- 208000007232 portal hypertension Diseases 0.000 description 3
- 201000000742 primary sclerosing cholangitis Diseases 0.000 description 3
- 230000000552 rheumatic effect Effects 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 201000000980 schizophrenia Diseases 0.000 description 3
- 208000010157 sclerosing cholangitis Diseases 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 230000007863 steatosis Effects 0.000 description 3
- 231100000240 steatosis hepatitis Toxicity 0.000 description 3
- 206010043778 thyroiditis Diseases 0.000 description 3
- 230000001256 tonic effect Effects 0.000 description 3
- VGTHQGYGDALBKQ-BUVFEPMLSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(2,5-dimethylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=CC(=CC=C1C)C VGTHQGYGDALBKQ-BUVFEPMLSA-N 0.000 description 2
- BSHPELRGWWZVIK-RFVSGWPVSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(2-fluoro-5-methylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=CC(=CC=C1F)C BSHPELRGWWZVIK-RFVSGWPVSA-N 0.000 description 2
- ZBPKKTZQHQNRHT-RFVSGWPVSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(2-fluoro-6-methylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=C(C=CC=C1C)F ZBPKKTZQHQNRHT-RFVSGWPVSA-N 0.000 description 2
- MSTLXKIZWUDOOH-JJXUHFIVSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(5-fluoro-2-methylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=CC(=CC=C1C)F MSTLXKIZWUDOOH-JJXUHFIVSA-N 0.000 description 2
- VFWPQDLLPSTMCF-JJXUHFIVSA-N (3R)-1-[(1S,2S)-6-chloro-1-(2-fluorophenoxy)-4-methyl-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)C)Cl)OC1=C(C=CC=C1)F VFWPQDLLPSTMCF-JJXUHFIVSA-N 0.000 description 2
- WBFZYKVELUVTAO-CZAAIQMYSA-N CC1=C(C[C@@H]([C@H]2OC3=CC(F)=CC=C3)N(CCC3)C[C@@H]3N)C2=CC(Cl)=C1 Chemical compound CC1=C(C[C@@H]([C@H]2OC3=CC(F)=CC=C3)N(CCC3)C[C@@H]3N)C2=CC(Cl)=C1 WBFZYKVELUVTAO-CZAAIQMYSA-N 0.000 description 2
- WXCMSJCTGDSYJX-ROUUACIJSA-N CC1=CC(=CC=C1)O[C@@H]2[C@H](CC3=C2C=C(C=C3Cl)Cl)N(C)C Chemical compound CC1=CC(=CC=C1)O[C@@H]2[C@H](CC3=C2C=C(C=C3Cl)Cl)N(C)C WXCMSJCTGDSYJX-ROUUACIJSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 208000017701 Endocrine disease Diseases 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 208000034486 Multi-organ failure Diseases 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 206010068620 Post procedural constipation Diseases 0.000 description 2
- 206010054048 Postoperative ileus Diseases 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- 208000034189 Sclerosis Diseases 0.000 description 2
- 208000005770 Secondary Hyperparathyroidism Diseases 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940069978 calcium supplement Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 208000008275 microscopic colitis Diseases 0.000 description 2
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 2
- 230000002981 neuropathic effect Effects 0.000 description 2
- 201000001119 neuropathy Diseases 0.000 description 2
- 230000007823 neuropathy Effects 0.000 description 2
- 208000033808 peripheral neuropathy Diseases 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- ZRQJSWOPZOITNN-UHFFFAOYSA-N urea;dihydrochloride Chemical compound Cl.Cl.NC(N)=O ZRQJSWOPZOITNN-UHFFFAOYSA-N 0.000 description 2
- KYVINBMBHZGKHZ-AGHHOFFYSA-N (1S,2S)-2-[(3R)-3-aminopiperidin-1-yl]-6-chloro-1-(2-methylphenoxy)-2,3-dihydro-1H-indene-4-carbonitrile Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)C#N)Cl)OC1=C(C=CC=C1)C KYVINBMBHZGKHZ-AGHHOFFYSA-N 0.000 description 1
- LIDYAZKCGFCTGE-IRXDYDNUSA-N (1S,2S)-4,6-dichloro-N,N-dimethyl-1-phenoxy-2,3-dihydro-1H-inden-2-amine Chemical compound ClC1=C2C[C@@H]([C@H](C2=CC(=C1)Cl)OC1=CC=CC=C1)N(C)C LIDYAZKCGFCTGE-IRXDYDNUSA-N 0.000 description 1
- FMKSUUOPKFEKFK-WMZOPIPTSA-N (1S,2S)-6-chloro-4-methoxy-N,N-dimethyl-1-phenoxy-2,3-dihydro-1H-inden-2-amine Chemical compound ClC1=CC(=C2C[C@@H]([C@H](C2=C1)OC1=CC=CC=C1)N(C)C)OC FMKSUUOPKFEKFK-WMZOPIPTSA-N 0.000 description 1
- MTBJVERQKQVBQM-ROUUACIJSA-N (1S,2S)-6-chloro-N,N,4-trimethyl-1-phenoxy-2,3-dihydro-1H-inden-2-amine Chemical compound ClC1=CC(=C2C[C@@H]([C@H](C2=C1)OC1=CC=CC=C1)N(C)C)C MTBJVERQKQVBQM-ROUUACIJSA-N 0.000 description 1
- MEDBWSYQNRHALF-OREJSRFESA-N (2R)-1-[(1S,2S)-4,6-dichloro-1-phenoxy-2,3-dihydro-1H-inden-2-yl]-2-methylpiperidine Chemical compound ClC1=C2C[C@@H]([C@H](C2=CC(=C1)Cl)OC1=CC=CC=C1)N1[C@@H](CCCC1)C MEDBWSYQNRHALF-OREJSRFESA-N 0.000 description 1
- MEDBWSYQNRHALF-WVFSVQOHSA-N (2S)-1-[(1S,2S)-4,6-dichloro-1-phenoxy-2,3-dihydro-1H-inden-2-yl]-2-methylpiperidine Chemical compound ClC1=C2C[C@@H]([C@H](C2=CC(=C1)Cl)OC1=CC=CC=C1)N1[C@H](CCCC1)C MEDBWSYQNRHALF-WVFSVQOHSA-N 0.000 description 1
- BVFNXPIOAFINAP-HQOQDVMHSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(2,6-difluorophenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=C(C=CC=C1F)F BVFNXPIOAFINAP-HQOQDVMHSA-N 0.000 description 1
- MGUAZMMAMOSAPL-BUVFEPMLSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(2,6-dimethylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=C(C=CC=C1C)C MGUAZMMAMOSAPL-BUVFEPMLSA-N 0.000 description 1
- SIGHIWHZULHJDG-MJWYBRSISA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(2-fluorophenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=C(C=CC=C1)F SIGHIWHZULHJDG-MJWYBRSISA-N 0.000 description 1
- VYYMSFMSMYDCOM-JJXUHFIVSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(2-methylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=C(C=CC=C1)C VYYMSFMSMYDCOM-JJXUHFIVSA-N 0.000 description 1
- WNGRBRAQFYPUKD-UAOJZALGSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(3-fluorophenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=CC(=CC=C1)F WNGRBRAQFYPUKD-UAOJZALGSA-N 0.000 description 1
- KLFDNFBKULUHSP-OREJSRFESA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(3-methoxyphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=CC(=CC=C1)OC KLFDNFBKULUHSP-OREJSRFESA-N 0.000 description 1
- NKFZGJALYZPWIZ-NQERJWCQSA-N (3R)-1-[(1S,2S)-4,6-dichloro-1-(3-methylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)Cl)Cl)OC1=CC(=CC=C1)C NKFZGJALYZPWIZ-NQERJWCQSA-N 0.000 description 1
- SEORSPRXTZOAEW-JJXUHFIVSA-N (3R)-1-[(1S,2S)-6-chloro-4-fluoro-1-(2-methylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)F)Cl)OC1=C(C=CC=C1)C SEORSPRXTZOAEW-JJXUHFIVSA-N 0.000 description 1
- YDJNOHQXAKCURE-WVBUVRCRSA-N (3R)-1-[(1S,2S)-6-chloro-4-methoxy-1-(2-methylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)OC)Cl)OC1=C(C=CC=C1)C YDJNOHQXAKCURE-WVBUVRCRSA-N 0.000 description 1
- KFDAHSYXDAQRAX-JJXUHFIVSA-N (3R)-1-[(1S,2S)-6-chloro-4-methoxy-1-phenoxy-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)OC)Cl)OC1=CC=CC=C1 KFDAHSYXDAQRAX-JJXUHFIVSA-N 0.000 description 1
- JJOLDSNPRHXANB-AGHHOFFYSA-N (3R)-1-[(1S,2S)-6-chloro-4-methyl-1-(2-methylphenoxy)-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)C)Cl)OC1=C(C=CC=C1)C JJOLDSNPRHXANB-AGHHOFFYSA-N 0.000 description 1
- KTDFTGSLEJNRMB-CZAAIQMYSA-N (3R)-1-[(1S,2S)-6-chloro-4-methyl-1-phenoxy-2,3-dihydro-1H-inden-2-yl]piperidin-3-amine Chemical compound N[C@H]1CN(CCC1)[C@@H]1[C@H](C2=CC(=CC(=C2C1)C)Cl)OC1=CC=CC=C1 KTDFTGSLEJNRMB-CZAAIQMYSA-N 0.000 description 1
- GTSVLAYDWOCJJK-PMACEKPBSA-N 1-[(1S,2S)-6-chloro-4-methyl-1-phenoxy-2,3-dihydro-1H-inden-2-yl]piperazine Chemical compound ClC1=CC(=C2C[C@@H]([C@H](C2=C1)OC1=CC=CC=C1)N1CCNCC1)C GTSVLAYDWOCJJK-PMACEKPBSA-N 0.000 description 1
- JJJHHKWBIXYOKT-SFTDATJTSA-N 4-[(1S,2S)-4,6-dichloro-1-phenoxy-2,3-dihydro-1H-inden-2-yl]-N,N-dimethylpiperazine-1-carboxamide Chemical compound ClC1=C2C[C@@H]([C@H](C2=CC(=C1)Cl)OC1=CC=CC=C1)N1CCN(CC1)C(N(C)C)=O JJJHHKWBIXYOKT-SFTDATJTSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- HDHCJFMJOFPIST-XGRCMKMKSA-N CC1=CC(O[C@H]2C3=CC(Cl)=CC(Cl)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=CC(C)=C1 Chemical compound CC1=CC(O[C@H]2C3=CC(Cl)=CC(Cl)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=CC(C)=C1 HDHCJFMJOFPIST-XGRCMKMKSA-N 0.000 description 1
- AIQXNWJTECYHJN-WTNAPCKOSA-N CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(C#N)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=C1 Chemical compound CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(C#N)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=C1 AIQXNWJTECYHJN-WTNAPCKOSA-N 0.000 description 1
- YUIVUGRTCCXFGT-WTNAPCKOSA-N CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(C)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=C1 Chemical compound CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(C)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=C1 YUIVUGRTCCXFGT-WTNAPCKOSA-N 0.000 description 1
- GJOVQWRVILWUKW-VXKWHMMOSA-N CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(Cl)=C3C[C@@H]2N(CC2)CCN2C(N(C)C)=O)=C1 Chemical compound CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(Cl)=C3C[C@@H]2N(CC2)CCN2C(N(C)C)=O)=C1 GJOVQWRVILWUKW-VXKWHMMOSA-N 0.000 description 1
- URBNETVZUYECQV-NQERJWCQSA-N CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(F)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=C1 Chemical compound CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(F)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=C1 URBNETVZUYECQV-NQERJWCQSA-N 0.000 description 1
- UJXDADDHOOLMIC-BUVFEPMLSA-N CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(OC)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=C1 Chemical compound CC1=CC=CC(O[C@H]2C3=CC(Cl)=CC(OC)=C3C[C@@H]2N(CCC2)C[C@@H]2N)=C1 UJXDADDHOOLMIC-BUVFEPMLSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010016807 Fluid retention Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 208000010718 Multiple Organ Failure Diseases 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- BWCAHALIOMUTEG-UAOJZALGSA-N N[C@H](CCC1)CN1[C@@H](CC(C1=CC(Cl)=C2)=C2Cl)[C@H]1OC1=CC(F)=CC(F)=C1 Chemical compound N[C@H](CCC1)CN1[C@@H](CC(C1=CC(Cl)=C2)=C2Cl)[C@H]1OC1=CC(F)=CC(F)=C1 BWCAHALIOMUTEG-UAOJZALGSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 208000028208 end stage renal disease Diseases 0.000 description 1
- 201000000523 end stage renal failure Diseases 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000007154 intracellular accumulation Effects 0.000 description 1
- 208000002741 leukoplakia Diseases 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000001578 tight junction Anatomy 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023000316A JP2023052205A (ja) | 2017-01-09 | 2023-01-04 | 消化管障害を処置するために有用な化合物 |
| JP2025000028A JP2025060986A (ja) | 2017-01-09 | 2025-01-05 | 消化管障害を処置するために有用な化合物 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762444335P | 2017-01-09 | 2017-01-09 | |
| US62/444,335 | 2017-01-09 | ||
| US201762541097P | 2017-08-04 | 2017-08-04 | |
| US62/541,097 | 2017-08-04 | ||
| PCT/US2018/013020 WO2018129552A1 (en) | 2017-01-09 | 2018-01-09 | Compounds useful for treating gastrointestinal tract disorders |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023000316A Division JP2023052205A (ja) | 2017-01-09 | 2023-01-04 | 消化管障害を処置するために有用な化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020515516A JP2020515516A (ja) | 2020-05-28 |
| JP2020515516A5 true JP2020515516A5 (enExample) | 2021-02-25 |
| JP7292207B2 JP7292207B2 (ja) | 2023-06-16 |
Family
ID=61168155
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019537185A Active JP7292207B2 (ja) | 2017-01-09 | 2018-01-09 | 消化管障害を処置するために有用な化合物 |
| JP2023000316A Withdrawn JP2023052205A (ja) | 2017-01-09 | 2023-01-04 | 消化管障害を処置するために有用な化合物 |
| JP2025000028A Pending JP2025060986A (ja) | 2017-01-09 | 2025-01-05 | 消化管障害を処置するために有用な化合物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023000316A Withdrawn JP2023052205A (ja) | 2017-01-09 | 2023-01-04 | 消化管障害を処置するために有用な化合物 |
| JP2025000028A Pending JP2025060986A (ja) | 2017-01-09 | 2025-01-05 | 消化管障害を処置するために有用な化合物 |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US11242337B2 (enExample) |
| EP (1) | EP3565808B1 (enExample) |
| JP (3) | JP7292207B2 (enExample) |
| KR (2) | KR102669987B1 (enExample) |
| CN (2) | CN110267944B (enExample) |
| AU (2) | AU2018205400C1 (enExample) |
| CA (1) | CA3049678A1 (enExample) |
| IL (1) | IL267805B (enExample) |
| MA (1) | MA47207A (enExample) |
| MX (1) | MX395405B (enExample) |
| NZ (1) | NZ754992A (enExample) |
| UA (1) | UA126283C2 (enExample) |
| WO (1) | WO2018129552A1 (enExample) |
| ZA (1) | ZA201904297B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA201991676A1 (ru) * | 2017-01-09 | 2020-01-30 | Арделикс, Инк. | Ингибиторы nhe-опосредованного антипорта |
| JP7292207B2 (ja) * | 2017-01-09 | 2023-06-16 | アルデリックス， インコーポレイテッド | 消化管障害を処置するために有用な化合物 |
| WO2020051014A1 (en) * | 2018-09-04 | 2020-03-12 | Teva Pharmaceuticals International Gmbh | Processes for the preparation of tenapanor and intermediates thereof |
| GB201815018D0 (en) * | 2018-09-14 | 2018-10-31 | Univ Oxford Innovation Ltd | Enantiomeric compounds |
| CN111954669B (zh) * | 2019-03-14 | 2023-04-07 | 深圳仁泰医药科技有限公司 | Nhe3抑制剂的晶型a及其制备方法和应用 |
| KR102681183B1 (ko) * | 2019-05-16 | 2024-07-04 | 일라이 릴리 앤드 캄파니 | 나트륨-수소 교환기 3 억제제 화합물 |
| CN113636960A (zh) * | 2021-08-24 | 2021-11-12 | 上海皓元医药股份有限公司 | 一种2-(氯磺酰基)环己烷-1-烯甲酸乙酯衍生物的制备方法 |
| CN117462525B (zh) * | 2023-09-06 | 2024-11-15 | 广州市第一人民医院（广州消化疾病中心、广州医科大学附属市一人民医院、华南理工大学附属第二医院） | 衣康酸在治疗坏死性小肠结肠炎患者中的应用 |
| CN119613318A (zh) * | 2024-11-29 | 2025-03-14 | 滁州市庆云医药有限公司 | 一种西洛多辛中间体及其制备方法 |
Family Cites Families (127)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3926891A (en) | 1974-03-13 | 1975-12-16 | Dow Chemical Co | Method for making a crosslinkable aqueous solution which is useful to form soft, water-swellable polyacrylate articles |
| US3935099A (en) | 1974-04-03 | 1976-01-27 | The United States Of America As Represented By The Secretary Of Agriculture | Method of reducing water content of emulsions, suspensions, and dispersions with highly absorbent starch-containing polymeric compositions |
| US3997484A (en) | 1974-04-03 | 1976-12-14 | The United States Of America As Represented By The Secretary Of Agriculture | Highly-absorbent starch-containing polymeric compositions |
| US4090013A (en) | 1975-03-07 | 1978-05-16 | National Starch And Chemical Corp. | Absorbent composition of matter |
| JPS51125468A (en) | 1975-03-27 | 1976-11-01 | Sanyo Chem Ind Ltd | Method of preparing resins of high water absorbency |
| JPS5346389A (en) | 1976-10-07 | 1978-04-25 | Kao Corp | Preparation of self-crosslinking polymer of acrylic alkali metal salt |
| US4190562A (en) | 1977-04-04 | 1980-02-26 | The B. F. Goodrich Company | Improved water absorbent copolymers of copolymerizable carboxylic acids and acrylic or methacrylic esters |
| US4470975A (en) | 1977-10-21 | 1984-09-11 | The Johns Hopkins University | Method and composition for the elimination of water from an animal body |
| US4286082A (en) | 1979-04-06 | 1981-08-25 | Nippon Shokubai Kagaku Kogyo & Co., Ltd. | Absorbent resin composition and process for producing same |
| JPS6025045B2 (ja) | 1980-03-19 | 1985-06-15 | 製鉄化学工業株式会社 | 塩水吸収能のすぐれたアクリル酸重合体の製造方法 |
| JPS57158209A (en) | 1981-03-25 | 1982-09-30 | Kao Corp | Production of bead-form highly water-absorbing polymer |
| JPS5832607A (ja) | 1981-08-20 | 1983-02-25 | Kao Corp | 吸水性に優れた吸水材料の製造法 |
| US4985518A (en) | 1981-10-26 | 1991-01-15 | American Colloid Company | Process for preparing water-absorbing resins |
| JPS6187702A (ja) | 1984-10-05 | 1986-05-06 | Seitetsu Kagaku Co Ltd | 吸水性樹脂の製造方法 |
| US4708997A (en) | 1985-07-22 | 1987-11-24 | The Dow Chemical Company | Suspending agent for the suspension polymerization of water-soluble monomers |
| US4806532A (en) | 1985-10-08 | 1989-02-21 | Mayo Foundation For Medical Education And Research | Inhibition of epithelial phosphate transport |
| DE3544770A1 (de) | 1985-12-18 | 1987-06-19 | Stockhausen Chem Fab Gmbh | Verfahren und vorrichtung zum kontinuierlichen herstellen von polymerisaten und copolymerisaten der acrylsaeure und/oder methacrylsaeure |
| US4766004A (en) | 1986-12-19 | 1988-08-23 | Warner-Lambert Company | Crunchy, highly palatable, bulk-increasing, dietary fiber supplement composition |
| IT1217123B (it) | 1987-02-05 | 1990-03-14 | Rotta Research Lab | Derivati otticamente attivi dell acido 5 pentilammino 5 oxo pentanoico r ad attivita antagonista della colecistochinina e procedimento per la loro preparazione |
| US4999200A (en) | 1987-12-09 | 1991-03-12 | Marion Laboratories | Psyllium tablet composition, method of manufacture and method of use |
| US5149541A (en) | 1988-10-03 | 1992-09-22 | The Procter & Gamble Company | Psyllium-containing produces with a distribution of particle size |
| US5145906A (en) | 1989-09-28 | 1992-09-08 | Hoechst Celanese Corporation | Super-absorbent polymer having improved absorbency properties |
| US5126150A (en) | 1990-10-01 | 1992-06-30 | The Procter & Gamble Company | Compositions containing psyllium |
| HUT64023A (en) | 1991-03-22 | 1993-11-29 | Sandoz Ag | Process for producing aminoguanidine derivatives and pharmaceutical compositions comprising such compounds |
| FR2674849B1 (fr) | 1991-04-02 | 1994-12-23 | Logeais Labor Jacques | Nouveaux derives de n-cyclohexyl benzamides ou thiobenzamides, leurs preparations et leurs applications en therapeutique. |
| US5140102A (en) | 1991-09-23 | 1992-08-18 | Monsanto Company | Pentadecapeptide, guanylin, which stimulates intestinal guanylate cyclase |
| SG50624A1 (en) | 1991-12-30 | 1998-07-20 | Neurex Corp | Methods of producing analgesia and enhancing opiate analgesia |
| US5824645A (en) | 1991-12-30 | 1998-10-20 | Neurex Corporation | Method of treating inflammation |
| US5969097A (en) | 1992-06-23 | 1999-10-19 | G. D. Searle & Co. | Human guanylin |
| DK0612723T3 (da) | 1993-02-20 | 1998-03-30 | Hoechst Ag | Substituerede benzoylguanidiner, fremgangsmåde til fremstilling, deres anvendelse som lægemiddel, som inhibitor af den cellulære Na+/H+-udbytning eller som diagnostikum samt lægemiddel med indhold deraf |
| US5629377A (en) | 1993-03-10 | 1997-05-13 | The Dow Chemical Company | Water absorbent resin particles of crosslinked carboxyl containing polymers and method of preparation |
| IL109570A0 (en) | 1993-05-17 | 1994-08-26 | Fujisawa Pharmaceutical Co | Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof |
| US5489670A (en) | 1993-10-29 | 1996-02-06 | G. D. Searle & Co. | Human uroguanylin |
| US5610145A (en) | 1994-04-15 | 1997-03-11 | Warner-Lambert Company | Tachykinin antagonists |
| US5650222A (en) | 1995-01-10 | 1997-07-22 | The Procter & Gamble Company | Absorbent foam materials for aqueous fluids made from high internal phase emulsions having very high water-to-oil ratios |
| DE19518796A1 (de) | 1995-05-22 | 1996-11-28 | Hoechst Ag | Fluorphenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DK0835126T3 (da) | 1995-06-27 | 2003-07-14 | Elan Pharm Inc | Sammensætninger og formuleringer til fremstilling af analgesimidler og til hamning af fremadskridende neuropatiske amertelidelser |
| US5795864A (en) | 1995-06-27 | 1998-08-18 | Neurex Corporation | Stable omega conopetide formulations |
| US6054429A (en) | 1996-03-08 | 2000-04-25 | Elan Pharmaceuticals, Inc. | Epidural method of producing analgesia |
| US5550167A (en) | 1995-08-30 | 1996-08-27 | The Procter & Gamble Company | Absorbent foams made from high internal phase emulsions useful for acquiring aqueous fluids |
| ATE289994T1 (de) | 1995-11-24 | 2005-03-15 | Glaxosmithkline Spa | Chinolin-derivate |
| GB9524104D0 (en) | 1995-11-24 | 1996-01-24 | Smithkline Beecham Spa | Novel compounds |
| DE19548812A1 (de) | 1995-12-27 | 1997-07-03 | Hoechst Ag | Verwendung von Inhibitoren des zellulären Na·+·/H·+·-Exchangers (NHE) zur Herstellung eines Medikaments zur Atemstimulation |
| EP0837055A1 (en) | 1996-07-30 | 1998-04-22 | Hoechst Aktiengesellschaft | Substituted Indanylidineacetylguanidines, process for their preparation, their use as medicaments or diagnostic and medicaments containing them |
| DE19633966A1 (de) | 1996-08-22 | 1998-02-26 | Hoechst Ag | Phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| AU4176997A (en) | 1996-09-16 | 1998-04-02 | Warner-Lambert Company | 3-alkyl-3-phenyl-piperidines |
| DK0975347T3 (da) | 1997-02-28 | 2008-06-16 | Nycomed Gmbh | Synergistisk kombination af PDE-inhibitorer og adenylatcyclase-agonister eller guanylcyclyseagonister |
| NZ329807A (en) | 1997-04-23 | 2000-07-28 | Pfizer | NK-1 receptor antagonists and P receptor antagonists 2-Diarylmethyl-3-amino-1-azabicyclo[2.2.2]octane derivatives and amino substituted N-containing rings as agents for treating irritable bowel syndrome |
| KR100219918B1 (ko) | 1997-07-03 | 1999-09-01 | 김윤 | 대장선택적 약물전달용 조성물 |
| US20010006972A1 (en) | 1998-04-21 | 2001-07-05 | Stephen A. Williams | Nk-1 receptor antagonists for the treatment of symptoms of irritable bowel syndrome |
| KR20000011247A (ko) | 1998-07-23 | 2000-02-25 | 김윤 | 다당류를이용한대장선택성약물전달조성물및약학제제 |
| DE19849722A1 (de) | 1998-10-28 | 2000-05-04 | Aventis Pharma Gmbh | Substituierte Phenyl-alkenoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| HK1041703A1 (zh) | 1999-01-21 | 2002-07-19 | Board Of Regents The University Of Texas System | 肠道顶膜钠/磷酸盐共同传送的抑制剂 |
| FR2789493B1 (fr) | 1999-02-09 | 2001-03-09 | Gemplus Card Int | Procede de detection d'objets portables et systeme de mise en oeuvre |
| US6624150B2 (en) | 1999-02-26 | 2003-09-23 | Inspire Pharmaceuticals, Inc. | Method of treating gastrointestinal tract disease with purinergic receptor agonists |
| US6287609B1 (en) | 1999-06-09 | 2001-09-11 | Wisconsin Alumni Research Foundation | Unfermented gel fraction from psyllium seed husks |
| DE60038449T2 (de) | 1999-07-19 | 2009-04-09 | University Of North Carolina At Chapel Hill | Arzneimittelwirkstoffe mit zwei kovalent verknüpften wirkstoffgruppen (natriumkanalblocker/p2y2 rezeptor agonist) zur behandlung von schleimhäuten |
| CO5190714A1 (es) | 1999-07-20 | 2002-08-29 | Smithkline Beecham Corp | Inhibidores del transporte de fosfato |
| US6107356A (en) | 1999-08-23 | 2000-08-22 | The Procter & Gamble Company | High suction polymeric foam materials |
| DE19941764A1 (de) | 1999-09-02 | 2001-03-15 | Aventis Pharma Gmbh | Substituierte Acylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikamente oder Diagnostika sowie sie enthaltende Medikamente |
| SE9903291D0 (sv) | 1999-09-15 | 1999-09-15 | Astra Ab | New process |
| DE19945302A1 (de) | 1999-09-22 | 2001-03-29 | Merck Patent Gmbh | Biphenylderivate als NHE-3-Inhibitoren |
| US6887870B1 (en) | 1999-10-12 | 2005-05-03 | Bristol-Myers Squibb Company | Heterocyclic sodium/proton exchange inhibitors and method |
| WO2001032180A2 (en) | 1999-11-01 | 2001-05-10 | Rodeva Limited | Composition for treatment of constipation and irritable bowel syndrome |
| AUPQ514600A0 (en) | 2000-01-18 | 2000-02-10 | James Cook University | Brain injury treatment |
| WO2001064212A1 (en) | 2000-03-01 | 2001-09-07 | University College London | Modulators of the endocannabinoid uptake and of the vallinoid receptors |
| DE10015248A1 (de) | 2000-03-28 | 2001-10-04 | Merck Patent Gmbh | Bisamidino-Verbindungen als NHE-3 Inhibitoren |
| DE10019062A1 (de) | 2000-04-18 | 2001-10-25 | Merck Patent Gmbh | 2-Guanidino-4-aryl-chinazoline als NHE-3 Inhibitoren |
| WO2001082924A1 (en) | 2000-05-02 | 2001-11-08 | Smithkline Beecham Corporation | Phosphate transport inhibitors |
| PL359931A1 (en) | 2000-05-12 | 2004-09-06 | Smithkline Beecham Corporation | Phosphate transport inhibitors |
| DE10043667A1 (de) | 2000-09-05 | 2002-03-14 | Merck Patent Gmbh | 2-Guanidino-4-aryl-chinazoline |
| US6414016B1 (en) | 2000-09-05 | 2002-07-02 | Sucampo, A.G. | Anti-constipation composition |
| DE10046993A1 (de) | 2000-09-22 | 2002-04-11 | Aventis Pharma Gmbh | Substituierte Zimtsäureguanidide, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltendes Medikament |
| WO2002028353A2 (en) | 2000-10-05 | 2002-04-11 | Smithkline Beecham Corporation | Phosphate transport inhibitors |
| DE60132256T2 (de) | 2000-11-20 | 2008-12-24 | Sorbent Therapeutics, Inc., Vernon Hills | Wasserabsorbierende polymere und deren verwendung |
| DE10063294A1 (de) | 2000-12-19 | 2002-07-04 | Aventis Pharma Gmbh | Substituierte Heterocyclo-Norbornylamino-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE60233040D1 (de) | 2001-03-29 | 2009-09-03 | Synergy Pharmaceuticals Inc | Guanylat-cyclase-rezeptor-agonisten zur behandlung von gewebeentzündung und karzinogenese |
| US6736705B2 (en) | 2001-04-27 | 2004-05-18 | Hitachi Global Storage Technologies | Polishing process for glass or ceramic disks used in disk drive data storage devices |
| US20030216449A1 (en) | 2001-05-11 | 2003-11-20 | Joseph Weinstock | Phosphate transport inhibitors |
| MY134211A (en) | 2001-05-18 | 2007-11-30 | Smithkline Beecham Corp | Novel use |
| JP2007131532A (ja) | 2001-09-28 | 2007-05-31 | Kirin Brewery Co Ltd | 生体内リン輸送を阻害する化合物およびそれを含んでなる医薬 |
| FR2830451B1 (fr) | 2001-10-09 | 2004-04-30 | Inst Nat Sante Rech Med | Utilisation de peptides analogues de la thymuline(pat)pour la fabrication de medicaments contre la douleur |
| ATE425968T1 (de) | 2001-12-05 | 2009-04-15 | Sanofi Aventis Deutschland | Substituierte 4-phenyltetrahydroisochinoline, verfahren zu ihrer herstellung, ihre verwendung als medikament, sowie sie enthaltendes medikament |
| US6911453B2 (en) | 2001-12-05 | 2005-06-28 | Aventis Pharma Deutschland Gmbh | Substituted 4-phenyltetrahydroisoquinolinium, process for their preparation, their use as a medicament, and medicament containing them |
| WO2003048134A1 (en) | 2001-12-05 | 2003-06-12 | Japan Tobacco Inc. | Triazole compound and medicinal use thereof |
| DE10161767A1 (de) | 2001-12-15 | 2003-06-26 | Merck Patent Gmbh | 2-Guanidino-4-heterocyclyl-chinazoline |
| EP1321142A1 (en) | 2001-12-21 | 2003-06-25 | Novartis AG | Solid pharmaceutical composition for oral administration of Tegaserod |
| US6703405B2 (en) | 2001-12-22 | 2004-03-09 | Aventis Pharma Deutschland Gmbh | Substituted 4-phenyltetrahydroisoquinolinium salts, process for their preparation, their use as a medicament, and medicament containing them |
| DE10163992A1 (de) | 2001-12-24 | 2003-07-03 | Merck Patent Gmbh | 4-Aryl-chinazoline |
| US7119120B2 (en) | 2001-12-26 | 2006-10-10 | Genzyme Corporation | Phosphate transport inhibitors |
| JP2005526079A (ja) | 2002-03-15 | 2005-09-02 | サイプレス バイオサイエンス， インコーポレイテッド | 内蔵痛症候群を処置するためのｎｅおよび５−ｈｔ再取り込み阻害剤 |
| AU2003218270A1 (en) | 2002-03-19 | 2003-10-08 | Genzyme Corporation | Phosphate transport inhibitors |
| CN101310723A (zh) | 2002-05-17 | 2008-11-26 | 迪欧加药品公司 | 有效的选择性阿片受体调制剂化合物的用途 |
| US7014862B2 (en) | 2002-05-20 | 2006-03-21 | The Procter & Gamble Company | Chewable compositions containing a gel-forming extract of psyllium |
| US6923466B2 (en) | 2002-12-17 | 2005-08-02 | James Tsai | Collapsible handcart capable of extending the area of carrier by operating handle |
| US7304036B2 (en) | 2003-01-28 | 2007-12-04 | Microbia, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US20050054705A1 (en) | 2003-02-04 | 2005-03-10 | Aventis Pharma Deutschland Gmbh | N-substituted (benzoimidazol-2-yl) phenylamines, process for their preparation, their use as medicament or diagnostic aid, and medicament comprising them |
| US7026303B2 (en) | 2003-02-18 | 2006-04-11 | The Procter & Gamble Company | Compositions comprising a polysaccharide component and one or more coating layers |
| WO2004085448A2 (en) | 2003-03-19 | 2004-10-07 | Genzyme Corporation | Unsaturated phosphinyl-phosphonate phosphate transport inhibitors |
| US7241775B2 (en) | 2003-03-24 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Composition, process of making, and medical use of substituted 4-phenyltetrahydroisoquinolines |
| DE10312963A1 (de) | 2003-03-24 | 2004-10-07 | Aventis Pharma Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| EP1614676A4 (en) | 2003-03-27 | 2009-03-25 | Kirin Pharma Kk | CONNECTION TO INHIBITING IN VIVO PHOSPHORUS TRANSPORT AND MEDICAMENT CONTAINING THEREOF |
| WO2005020612A1 (en) | 2003-08-20 | 2005-03-03 | Musky Communications (Proprietary) Limited | Telephonic communication |
| US20050244367A1 (en) | 2004-05-03 | 2005-11-03 | Ilypsa, Inc. | Phospholipase inhibitors localized in the gastrointestinal lumen |
| US8173596B2 (en) | 2004-05-14 | 2012-05-08 | The University Of North Carolina At Chapel Hill | Prouroguanylin, and synthetic analogs or proteolytic cleavage products derived from it, as therapeutic and diagnostic agents for diseases involving salt and/or fluid homeostasis |
| DE102004046492A1 (de) | 2004-09-23 | 2006-03-30 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| DE102004054847A1 (de) | 2004-11-13 | 2006-05-24 | Sanofi-Aventis Deutschland Gmbh | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE102005001411A1 (de) | 2005-01-12 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| DE102005044817A1 (de) | 2005-09-20 | 2007-03-22 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| DE102005044815A1 (de) | 2005-09-20 | 2007-03-22 | Sanofi-Aventis Deutschland Gmbh | Verwendung von Inhibitoren des Na+/H+ Austauschers, Subtyp 5 (NHE5) zur Gedächtnisverbesserung |
| AU2006311765A1 (en) | 2005-11-03 | 2007-05-18 | Ilypsa, Inc. | Phospholipase inhibitors, including multi-valent phospholipase inhibitors, and use thereof, including as lumen-localized phospholipase inhibitors |
| JP2009514893A (ja) | 2005-11-03 | 2009-04-09 | イリプサ， インコーポレイテッド | 多価インドール化合物およびホスホリパーゼａ２インヒビターとしてのその使用 |
| WO2008002971A2 (en) | 2006-06-29 | 2008-01-03 | Microbia, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US8779090B2 (en) | 2007-02-26 | 2014-07-15 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of heart failure and other disorders |
| MX2009011898A (es) | 2007-05-04 | 2009-11-18 | Ironwood Pharmaceuticals Inc | Composiciones y metodos para tratar trastornos asociados con retencion de sal o fluido. |
| CN103396402A (zh) | 2008-09-02 | 2013-11-20 | 赛诺菲-安万特 | 取代的氨基茚满及其类似物以及其医药用途 |
| US10543207B2 (en) | 2008-12-31 | 2020-01-28 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| CA2748607A1 (en) | 2008-12-31 | 2010-07-08 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| EP2590656B1 (en) | 2010-07-07 | 2017-11-15 | Ardelyx, Inc. | Compounds and methods for inhibiting phosphate transport |
| JP5827328B2 (ja) | 2010-07-07 | 2015-12-02 | アーデリクス，インコーポレーテッド | リン酸輸送を阻害する化合物及び方法 |
| WO2012006475A1 (en) | 2010-07-07 | 2012-01-12 | Ardelyx, Inc. | Compounds and methods for inhibiting phosphate transport |
| JP5827326B2 (ja) | 2010-07-07 | 2015-12-02 | アーデリクス，インコーポレーテッド | リン酸輸送を阻害する化合物及び方法 |
| WO2014029983A1 (en) * | 2012-08-21 | 2014-02-27 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US10376481B2 (en) * | 2012-08-21 | 2019-08-13 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2014029984A1 (en) | 2012-08-21 | 2014-02-27 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| ES2735992T3 (es) * | 2013-04-12 | 2019-12-23 | Ardelyx Inc | Compuestos de unión a NHE3 y procedimientos para inhibir el transporte de fosfatos |
| JP7292207B2 (ja) | 2017-01-09 | 2023-06-16 | アルデリックス， インコーポレイテッド | 消化管障害を処置するために有用な化合物 |
-
2018
- 2018-01-09 JP JP2019537185A patent/JP7292207B2/ja active Active
- 2018-01-09 CN CN201880009820.3A patent/CN110267944B/zh active Active
- 2018-01-09 US US16/476,836 patent/US11242337B2/en active Active
- 2018-01-09 NZ NZ754992A patent/NZ754992A/en unknown
- 2018-01-09 EP EP18703655.3A patent/EP3565808B1/en active Active
- 2018-01-09 AU AU2018205400A patent/AU2018205400C1/en active Active
- 2018-01-09 CN CN202410183141.5A patent/CN118221656A/zh active Pending
- 2018-01-09 UA UAA201908567A patent/UA126283C2/uk unknown
- 2018-01-09 KR KR1020197023352A patent/KR102669987B1/ko active Active
- 2018-01-09 CA CA3049678A patent/CA3049678A1/en active Pending
- 2018-01-09 KR KR1020247017226A patent/KR20240090875A/ko active Pending
- 2018-01-09 MX MX2019008170A patent/MX395405B/es unknown
- 2018-01-09 WO PCT/US2018/013020 patent/WO2018129552A1/en not_active Ceased
- 2018-01-09 MA MA047207A patent/MA47207A/fr unknown
-
2019
- 2019-06-28 ZA ZA2019/04297A patent/ZA201904297B/en unknown
- 2019-07-02 IL IL267805A patent/IL267805B/en unknown
-
2021
- 2021-12-21 US US17/558,227 patent/US20220306610A1/en not_active Abandoned
-
2022
- 2022-08-02 AU AU2022211830A patent/AU2022211830A1/en not_active Abandoned
-
2023
- 2023-01-04 JP JP2023000316A patent/JP2023052205A/ja not_active Withdrawn
- 2023-12-27 US US18/397,454 patent/US12281103B2/en active Active
-
2025
- 2025-01-05 JP JP2025000028A patent/JP2025060986A/ja active Pending
- 2025-03-04 US US19/070,289 patent/US20250263401A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2020515516A5 (enExample) | ||
| EP1833799B1 (en) | 3-PHENYL-PYRAZOLE DERIVATIVES AS MODULATORS OF THE 5-HT-2a SEROTONIN RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO | |
| RU2451015C2 (ru) | Производные 1,2,4-триазола в качестве ингибиторов сигма рецептора | |
| CA2620280C (en) | Novel triazole derivatives as ghrelin analogue ligands of growth hormone secretagogue receptors | |
| JP2020172503A (ja) | 疾患の治療のためのｋｄｍ１ａ阻害剤 | |
| JPH08505862A (ja) | アミノ酸誘導体、これらの化合物を含む医薬組成物及びそれらの調製方法 | |
| HUP0600810A2 (en) | New sulfonamide derivatives as bradykinin antagonists, process and intermediates for their preparation and pharmaceutical compositions containing them | |
| JP2020505333A5 (enExample) | ||
| JP5274470B2 (ja) | ブラジキニン拮抗剤としての新規ベンズアミド誘導体 | |
| CN101479261A (zh) | 3-吡唑基-苯甲酰胺-4-醚、其仲胺及其衍生物作为5-ht2a血清素受体的调节剂用于治疗与其相关的病症 | |
| SK20052000A3 (sk) | Nepeptidové inhibítory VLA-4 dependentnej bunkovej väzby použiteľné pri liečení zápalových, autoimunitných a respiračných chorôb | |
| JP2010515770A (ja) | ニコチン性アセチルコリン受容体モジュレーター | |
| CA2527159A1 (en) | 3-aminomethyl-pyrrolidines as n-type calcium channel blockers | |
| AU2019253831B2 (en) | Compositions and methods for treating neurodegenerative diseases | |
| WO2008057282A1 (en) | Calcium receptor modulating agents | |
| TW200922582A (en) | N-benzyl, N'-arylcarbonylpiperazine derivatives | |
| JP2016505550A (ja) | 置換トリアゾール及びイミダゾール化合物 | |
| JP5666468B2 (ja) | システインプロテアーゼ阻害剤 | |
| JP2009528319A5 (enExample) | ||
| CA2530310A1 (en) | Substituted diketopiperazines and their use as oxytocin antagonists | |
| JP2008538357A (ja) | 薬学的に活性なジアゼパン | |
| EP1904442B1 (en) | Histamine h3 receptor agents, preparation and therapeutic uses | |
| EA015419B1 (ru) | Новые производные фенантридина в качестве антагонистов брадикинина | |
| BG108332A (bg) | 4-(фенил-(пиперидин-4-ил)-амино)-бензамидни производни и тяхното използване за лечение на болка, потиснатост или стомашно-чревни разстройства | |
| US20190177284A1 (en) | Tetrazolyl-containing cyclopropanecarboxamides |