NO323779B1 - Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 - Google Patents
Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 Download PDFInfo
- Publication number
- NO323779B1 NO323779B1 NO20025587A NO20025587A NO323779B1 NO 323779 B1 NO323779 B1 NO 323779B1 NO 20025587 A NO20025587 A NO 20025587A NO 20025587 A NO20025587 A NO 20025587A NO 323779 B1 NO323779 B1 NO 323779B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- thiazol
- chloro
- acetyl
- ethyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 9
- 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 title 1
- 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 81
- 238000000034 method Methods 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 34
- 150000002431 hydrogen Chemical group 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- -1 4-bromo-5-chloro-2-thienyl Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 10
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 9
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 9
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 9
- 208000008589 Obesity Diseases 0.000 claims description 8
- 208000001132 Osteoporosis Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- PPXUHEORWJQRHJ-UHFFFAOYSA-N isovaleric acid ethyl ester Natural products CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
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- 230000009467 reduction Effects 0.000 claims description 7
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- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 4
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- XXOYUNQCBYNWNL-UHFFFAOYSA-N 4-chloro-n-(4-methyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 XXOYUNQCBYNWNL-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
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- AQRONHMIKZUPDV-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-(4-pentyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CCCCCC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 AQRONHMIKZUPDV-UHFFFAOYSA-N 0.000 claims description 3
- YONLSQQDISIPRX-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-methyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YONLSQQDISIPRX-UHFFFAOYSA-N 0.000 claims description 3
- ZMOURMHOEOISKY-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-propan-2-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC(C)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 ZMOURMHOEOISKY-UHFFFAOYSA-N 0.000 claims description 3
- ZLIJGGLRZJYQFO-UHFFFAOYSA-N 3-chloro-n-(4-ethyl-1,3-thiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 ZLIJGGLRZJYQFO-UHFFFAOYSA-N 0.000 claims description 3
- 208000028698 Cognitive impairment Diseases 0.000 claims description 3
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 3
- 206010024229 Leprosy Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 3
- 201000008980 hyperinsulinism Diseases 0.000 claims description 3
- 230000008102 immune modulation Effects 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- XBFJEUAGXOUBKK-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2,6-dichlorobenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 XBFJEUAGXOUBKK-UHFFFAOYSA-N 0.000 claims description 3
- ACRDEWAKELMRBD-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-chlorobenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 ACRDEWAKELMRBD-UHFFFAOYSA-N 0.000 claims description 3
- YMROFWINSIVBQO-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-phenylbenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 YMROFWINSIVBQO-UHFFFAOYSA-N 0.000 claims description 3
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- 150000003585 thioureas Chemical class 0.000 claims description 3
- 201000008827 tuberculosis Diseases 0.000 claims description 3
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- JVFCCRJSBNUDDU-UHFFFAOYSA-N 4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 JVFCCRJSBNUDDU-UHFFFAOYSA-N 0.000 claims description 2
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- 201000001421 hyperglycemia Diseases 0.000 claims description 2
- RBZGUHWMMJOALQ-UHFFFAOYSA-N n-(4-butyl-1,3-thiazol-2-yl)-3-chloro-2-methylbenzenesulfonamide Chemical compound CCCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 RBZGUHWMMJOALQ-UHFFFAOYSA-N 0.000 claims description 2
- UHHBLIGTCQFIQL-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2,4-dichloro-6-methylbenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 UHHBLIGTCQFIQL-UHFFFAOYSA-N 0.000 claims description 2
- LHALODNUSDEBTM-UHFFFAOYSA-N n-(5-bromo-4-tert-butyl-1,3-thiazol-2-yl)-4-chlorobenzenesulfonamide Chemical compound S1C(Br)=C(C(C)(C)C)N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 LHALODNUSDEBTM-UHFFFAOYSA-N 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
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- 230000003612 virological effect Effects 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 8
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- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- FKBBDKZYXDJBGC-UHFFFAOYSA-N 3-chloro-n-(4-ethenyl-1,3-thiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=C)=CS1 FKBBDKZYXDJBGC-UHFFFAOYSA-N 0.000 claims 1
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
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- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
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Landscapes
- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0001899A SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | New compounds |
PCT/SE2001/001156 WO2001090091A1 (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20025587D0 NO20025587D0 (no) | 2002-11-21 |
NO20025587L NO20025587L (no) | 2003-01-21 |
NO323779B1 true NO323779B1 (no) | 2007-07-02 |
Family
ID=20279781
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20025588A NO20025588L (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
NO20025586A NO323832B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
NO20025587A NO323779B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
NO20025585A NO323831B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20025588A NO20025588L (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
NO20025586A NO323832B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20025585A NO323831B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
Country Status (24)
Country | Link |
---|---|
US (7) | US7618961B2 (ko) |
EP (4) | EP1283833A1 (ko) |
JP (4) | JP2003534339A (ko) |
KR (4) | KR20030016271A (ko) |
CN (4) | CN1188403C (ko) |
AR (1) | AR033534A1 (ko) |
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Families Citing this family (185)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE0001899D0 (sv) * | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
JP2004502432A (ja) * | 2000-07-05 | 2004-01-29 | バイエル アクチェンゲゼルシャフト | ヒト11β−ヒドロキシステロイドデヒドロゲナーゼ1様酵素の調節 |
GB0107383D0 (en) * | 2001-03-23 | 2001-05-16 | Univ Edinburgh | Lipid profile modulation |
EP1461325B1 (en) * | 2001-11-22 | 2010-05-26 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
EA200400709A1 (ru) * | 2001-11-22 | 2004-12-30 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
AU2007205749B2 (en) * | 2001-11-22 | 2009-04-23 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
EA200400708A1 (ru) * | 2001-11-22 | 2004-10-28 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
EA200400707A1 (ru) * | 2001-11-22 | 2004-10-28 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
BR0214342A (pt) * | 2001-11-22 | 2004-09-14 | Biovitrum Ab | Inibidores de 11 - beta - hidroxi esteróide desidrogenase tipo 1 |
JP2005529846A (ja) | 2002-01-16 | 2005-10-06 | ユニバーシティ オブ バージニア パテント ファウンデーション | A1アデノシン受容体の2−アミノチアゾールアロステリックエンハンサ |
DE60317631T2 (de) * | 2002-02-01 | 2008-09-25 | Merck & Co., Inc. | 11-beta-hydroxysteroid-dehydrogenase-1-hemmer zur behandlung von diabetes, adipositas und dyslipidämie |
US7338969B2 (en) * | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
CA2480481A1 (en) * | 2002-03-29 | 2003-10-16 | Schering Corporation | Stereoselective alkylation of chiral 2-methyl-4-protected piperazines |
US20030198965A1 (en) | 2002-04-19 | 2003-10-23 | Isis Pharmaceuticals Inc. | Antisense modulation of hydroxysteroid 11-beta dehydrogenase 1 expression |
SE0201194D0 (sv) * | 2002-04-19 | 2002-04-19 | Astrazeneca Ab | New compounds |
AR040241A1 (es) * | 2002-06-10 | 2005-03-23 | Merck & Co Inc | Inhibidores de la 11-beta-hidroxiesteroide deshidrogrenasa 1 para el tratamiento de la diabetes obesidad y dislipidemia |
US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
WO2004027047A2 (en) * | 2002-09-18 | 2004-04-01 | Hanauske-Abel Hartmut M | INHIBITORS OF 11β-HYDROXYSTEROID DEHYDROGENASE AND USES THEREFOR |
BR0315166A (pt) * | 2002-10-11 | 2005-08-16 | Astrazeneca Ab | Uso de um composto ou de um sal farmaceuticamente aceitável do mesmo, composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, método para produzir um efeito inibidor de 11betahsd1 em um animal de sangue quente, tal como o homem, que necessita de tratamento |
MXPA05004434A (es) * | 2002-10-24 | 2005-07-26 | Sterix Ltd | Inhibidores de 11-beta-hidroxi esteroide deshidrogenasa tipo 1 y tipo 2. |
GB0224830D0 (en) | 2002-10-24 | 2002-12-04 | Sterix Ltd | Compound |
JP2006514102A (ja) * | 2002-11-07 | 2006-04-27 | アストラゼネカ アクチボラグ | 2−オキソ−エタンスルホンアミド誘導体 |
GB0226602D0 (en) * | 2002-11-14 | 2002-12-24 | Novartis Ag | Organic compounds |
PE20040693A1 (es) * | 2002-11-14 | 2004-11-23 | Novartis Ag | N-sulfonilaminotiazol como mediadores de la sulfatasa de esteroides |
JO2397B1 (en) * | 2002-12-20 | 2007-06-17 | ميرك شارب اند دوم كوربوريشن | Terazol derivatives as beta-hydroxy steroid dihydrogenase-1 inhibitors |
WO2004056744A1 (en) * | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
FR2849598B1 (fr) * | 2003-01-07 | 2006-09-22 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete, par augmentation du nombre de cellules des ilots de langerhans |
FR2849599B1 (fr) * | 2003-01-07 | 2006-12-29 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete |
TW200503994A (en) * | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
WO2004089470A2 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | New amide derivatives and pharmaceutical use thereof |
DE10314610A1 (de) | 2003-04-01 | 2004-11-04 | Aventis Pharma Deutschland Gmbh | Neues Diphenylazetidinon mit verbesserten physiologischen Eigenschaften, Verfahren zu dessen Herstellung, diese Verbindungen enthaltende Arzneimittel und dessen Verwendung |
DE602004025220D1 (de) | 2003-04-11 | 2010-03-11 | High Point Pharmaceuticals Llc | Pharmazeutische verwendungen von kondensierten 1,2,4-triazolen |
US7700583B2 (en) | 2003-04-11 | 2010-04-20 | High Point Pharmaceuticals, Llc | 11β-hydroxysteroid dehydrogenase type 1 active compounds |
US7501405B2 (en) | 2003-04-11 | 2009-03-10 | High Point Pharmaceuticals, Llc | Combination therapy using an 11β-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent for the treatment of metabolic syndrome and related diseases and disorders |
EP1785424A3 (en) * | 2003-04-11 | 2009-12-23 | High Point Pharmaceuticals, LLC | Fused 1,2,4-triazoles and pharmaceutical uses thereof |
WO2004103980A1 (en) * | 2003-05-21 | 2004-12-02 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type i |
US7173030B2 (en) | 2003-05-21 | 2007-02-06 | Biovitrum Ab | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 |
WO2004106294A2 (en) * | 2003-05-29 | 2004-12-09 | Merck & Co., Inc. | Triazole derivatives as inhibitors of 11-beta hydroxysteroid dehydrogenase-1 |
SE0301885D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use IV |
WO2004113310A1 (en) * | 2003-06-25 | 2004-12-29 | Biovitrum Ab | Use of an inhibitor of 11-b-hydroxysteroid dehydrogenase type 1 compounds for promoting wound healing |
SE0301884D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use III |
SE0301882D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use I |
SE0301883D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use II |
AU2004274309B2 (en) | 2003-09-22 | 2010-04-08 | Msd K.K. | Novel piperidine derivative |
GB0324792D0 (en) | 2003-10-23 | 2003-11-26 | Sterix Ltd | Compound |
GB0325745D0 (en) * | 2003-11-05 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
JP2007514731A (ja) * | 2003-12-19 | 2007-06-07 | ファイザー インコーポレイテッド | 糖尿病及び肥満症の治療のための11−ベータ−ヒドロキシステロイドデヒドロゲナーゼ1型(11−β−hsd−1)の阻害剤としてのベンゼンスルホニルアミノ−ピリジン−2−イル誘導体及び関連化合物 |
EP1703908A4 (en) | 2003-12-22 | 2009-07-08 | Amgen Inc | ARYLSULFONAMIDE COMPOUNDS AND RELATED APPLICATIONS |
WO2005073200A1 (en) | 2004-01-26 | 2005-08-11 | Merck & Co., Inc. | Novel crystalline forms of an inhibitor of 11-beta-hydroxysteroid dehydrogenase type 1 |
EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
JP2007261945A (ja) * | 2004-04-07 | 2007-10-11 | Taisho Pharmaceut Co Ltd | チアゾール誘導体 |
US7402704B2 (en) | 2004-04-14 | 2008-07-22 | Amgen Inc. | Arylsulfones and uses related thereto |
GB0408771D0 (en) * | 2004-04-20 | 2004-05-26 | Sterix Ltd | Compound |
ES2390057T3 (es) | 2004-04-20 | 2012-11-06 | Amgen Inc. | Arilsulfonilamidas y usos como hidroxiesteroide deshidrogenasa |
KR101192861B1 (ko) | 2004-05-07 | 2012-10-19 | 얀센 파마슈티카 엔.브이. | 11-베타 하이드록시스테로이드 탈수소효소 저해제로서의피롤리딘-2-온 및 피페리딘-2-온 유도체 |
US8686011B2 (en) | 2004-05-24 | 2014-04-01 | Amgen Inc. | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 |
TWI352700B (en) | 2004-05-24 | 2011-11-21 | Amgen Inc | Inhibitors of 11-beta-hydroxy steroid dehydrogenas |
CN1972918B (zh) * | 2004-06-28 | 2010-10-13 | 霍夫曼-拉罗奇有限公司 | 嘧啶衍生物 |
MX2007001271A (es) * | 2004-08-05 | 2007-03-21 | Hoffmann La Roche | N-acil-2-aminotiazoles sustituidos. |
AU2005279209B2 (en) | 2004-08-30 | 2011-03-24 | Janssen Pharmaceutica N.V. | Tricyclic lactam derivatives as 11-BETA hydroxysteroid dehydrogenase inhibitors |
DE602005017159D1 (de) | 2004-08-30 | 2009-11-26 | Janssen Pharmaceutica Nv | Oxysteroid-dehydrogenase-inhibitoren |
JP5208505B2 (ja) | 2004-08-30 | 2013-06-12 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 11−ベータヒドロキシステロイドデヒドロゲナーゼ阻害剤としてのn−2アダマンタニル−2−フェノキシ−アセトアミド誘導体 |
RU2392272C2 (ru) * | 2004-09-29 | 2010-06-20 | Ф.Хоффманн-Ля Рош Аг | Производные индазолона в качестве ингибиторов 11b-hsd1 |
MX2007003913A (es) * | 2004-10-04 | 2007-05-21 | Hoffmann La Roche | Alquil-piridinas como inhibidores de 11 beta para diabetes. |
WO2006040178A1 (en) * | 2004-10-14 | 2006-04-20 | Abbott Gmbh & Co.Kg | Arylsulfonylmethyl or arylsulfonamide substituted aromatic compounds suitable for treating disorders that respond to madulation of the dopamine d3 receptor |
WO2006047302A1 (en) | 2004-10-21 | 2006-05-04 | Transtech Pharma, Inc. | Bissulfonamide compounds as agonists of galr1, compositions, and methods of use |
EP1666467A1 (en) * | 2004-11-08 | 2006-06-07 | Evotec AG | 11Beta-HSD1 Inhibitors |
EP1659113A1 (en) * | 2004-11-08 | 2006-05-24 | Evotec AG | Inhibitors of 11beta-hydroxy steroid dehydrogenase type 1 (11beta-HSD1) |
WO2006051662A1 (ja) * | 2004-11-09 | 2006-05-18 | Taisho Pharmaceutical Co., Ltd. | チアゾール誘導体 |
WO2006059507A1 (ja) * | 2004-11-30 | 2006-06-08 | Sankyo Company, Limited | 11β-HSD1アンチセンス化合物 |
WO2006066109A2 (en) * | 2004-12-17 | 2006-06-22 | Takeda San Diego, Inc. | Hydroxysteroid dehydrogenase inhibitors |
GB0506133D0 (en) * | 2005-03-24 | 2005-05-04 | Sterix Ltd | Compound |
WO2006105127A2 (en) * | 2005-03-31 | 2006-10-05 | Takeda San Diego, Inc. | Hydroxysteroid dehydrogenase inhibitors |
AU2006232660B2 (en) | 2005-04-05 | 2010-03-25 | F. Hoffmann-La Roche Ag | 1H-Pyrazole 4-Carboxylamides, their preparation and their use as 11Beta-hydroxysteroid dehydrogenase |
US8138206B2 (en) | 2005-05-30 | 2012-03-20 | Msd. K.K. | Piperidine derivative |
DE602006010546D1 (de) * | 2005-06-16 | 2009-12-31 | Pfizer | N-(pyridin-2-yl)sulfonamidderivate |
WO2006134481A1 (en) * | 2005-06-16 | 2006-12-21 | Pfizer Inc. | Inhibitors of 11-beta hydroxysteroid dehydrogenase type 1 |
US20100216758A1 (en) | 2005-08-10 | 2010-08-26 | Makoto Ando | Pyridone Compounds |
DE602006017712D1 (de) | 2005-08-24 | 2010-12-02 | Banyu Pharma Co Ltd | Phenylpyridonderivat |
US7622492B2 (en) | 2005-08-31 | 2009-11-24 | Hoffmann-La Roche Inc. | Pyrazolones as inhibitors of 11β-hydroxysteroid dehydrogenase |
WO2007029847A1 (ja) | 2005-09-07 | 2007-03-15 | Banyu Pharmaceutical Co., Ltd. | 二環性芳香族置換ピリドン誘導体 |
BRPI0616463A2 (pt) | 2005-09-29 | 2011-06-21 | Merck & Co Inc | composto, composição farmacêutica, e, uso de um composto |
JP2007099659A (ja) * | 2005-10-03 | 2007-04-19 | Toray Fine Chemicals Co Ltd | ピペラジンカルボン酸エステルの製造法 |
US7683083B2 (en) * | 2005-10-12 | 2010-03-23 | Vertex Pharmaceuticals Incorporated | Biphenyl derivatives as modulators of voltage gated ion channels |
BRPI0617621A2 (pt) | 2005-10-21 | 2011-08-02 | Novartis Ag | combinação de compostos orgánicos |
JPWO2007049798A1 (ja) | 2005-10-27 | 2009-04-30 | 萬有製薬株式会社 | 新規ベンゾオキサチイン誘導体 |
KR101318127B1 (ko) | 2005-11-10 | 2013-10-16 | 엠에스디 가부시키가이샤 | 아자 치환된 스피로 유도체 |
US20070110802A1 (en) * | 2005-11-15 | 2007-05-17 | Janan Jona | Wet granulation process |
EP1951696A2 (en) | 2005-11-22 | 2008-08-06 | Amgen Inc. | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
KR20080081178A (ko) * | 2005-12-21 | 2008-09-08 | 버텍스 파마슈티칼스 인코포레이티드 | 이온 채널 조절인자로서의 헤테로사이클릭 유도체 |
WO2007076875A2 (en) * | 2006-01-06 | 2007-07-12 | Aarhus Universitet | Compounds acting on the serotonin transporter |
KR101081293B1 (ko) | 2006-01-18 | 2011-11-08 | 에프. 호프만-라 로슈 아게 | 11 베타-에이치에스디1 억제제로서 티아졸 |
BRPI0710468A2 (pt) * | 2006-04-24 | 2011-08-16 | Lilly Co Eli | composto, e, composição farmacêutica |
MX2008013644A (es) * | 2006-04-24 | 2009-03-06 | Lilly Co Eli | Pirrolidinonas sustituidas como inhibidores de 11-beta-hidroxiesteroide deshidrogenasa 1. |
PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
CN101096363B (zh) * | 2006-06-27 | 2011-05-11 | 中国人民解放军军事医学科学院毒物药物研究所 | 2,4,5-三取代噻唑类化合物、其制备方法、药物组合物及其制药用途 |
CA2666193A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, process for preparing them, medicaments comprising these compounds, and their use |
WO2008039327A2 (en) | 2006-09-22 | 2008-04-03 | Merck & Co., Inc. | Method of treatment using fatty acid synthesis inhibitors |
US20090247560A1 (en) | 2006-09-28 | 2009-10-01 | Banyu Pharmaceutical Co., Ltd. | Diaryl ketimine derivative |
DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
CN101668524B (zh) * | 2007-02-12 | 2012-10-24 | 阿斯利康(瑞典)有限公司 | 作为11-β-HSD1抑制剂的吡唑衍生物 |
US20110003852A1 (en) | 2007-02-23 | 2011-01-06 | Soren Ebdrup | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
WO2008101886A1 (en) | 2007-02-23 | 2008-08-28 | High Point Pharmaceuticals, Llc | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
CA2675669C (en) | 2007-02-23 | 2015-05-26 | High Point Pharmaceuticals, Llc | Novel compounds |
JP5361857B2 (ja) | 2007-03-23 | 2013-12-04 | ファイザー・リミテッド | イオンチャネルの阻害剤 |
CA2682727C (en) | 2007-04-02 | 2016-03-22 | Banyu Pharmaceutical Co., Ltd. | Indoledione derivative |
EP2152081B1 (en) * | 2007-04-11 | 2012-10-24 | High Point Pharmaceuticals, LLC | Novel compounds |
US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
JP5223864B2 (ja) | 2007-06-27 | 2013-06-26 | 大正製薬株式会社 | 11β−HSD1阻害活性を有する化合物 |
EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
US20110015181A1 (en) | 2008-03-06 | 2011-01-20 | Makoto Ando | Alkylaminopyridine derivative |
WO2009119726A1 (ja) | 2008-03-28 | 2009-10-01 | 萬有製薬株式会社 | メラニン凝集ホルモン受容体拮抗作用を有するジアリールメチルアミド誘導体 |
ES2627848T3 (es) | 2008-06-04 | 2017-07-31 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
AU2009261248A1 (en) | 2008-06-19 | 2009-12-23 | Banyu Pharmaceutical Co., Ltd. | Spirodiamine-diarylketoxime derivative |
AR072707A1 (es) | 2008-07-09 | 2010-09-15 | Sanofi Aventis | Compuestos heterociclicos, procesos para su preparacion, medicamentos que comprenden estos compuestos y el uso de los mismos |
ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
EP2319841A1 (en) | 2008-07-30 | 2011-05-11 | Msd K.K. | (5-membered)-(5-membered) or (5-membered)-(6-membered) fused ring cycloalkylamine derivative |
WO2010047982A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
PE20110852A1 (es) | 2008-10-30 | 2011-11-25 | Merck Sharp & Dohme | Antagonistas del receptor de orexina de isonicotinamida |
AU2009309037A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
KR200452117Y1 (ko) * | 2008-11-10 | 2011-02-08 | 대성공업주식회사 | 휠체어용 브레이크 와이어 케이블 지지 브래킷 |
CN102223797A (zh) | 2008-11-21 | 2011-10-19 | 高点制药有限责任公司 | 金刚烷基苯甲酰胺化合物 |
WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
ES2350077B1 (es) | 2009-06-04 | 2011-11-04 | Laboratorios Salvat, S.A. | Compuestos inhibidores de 11beta-hidroxiesteroide deshidrogenasa de tipo 1. |
DK2470552T3 (en) | 2009-08-26 | 2014-02-17 | Sanofi Sa | NOVEL, CRYSTALLINE, heteroaromatic FLUORGLYCOSIDHYDRATER, MEDICINES COVERING THESE COMPOUNDS AND THEIR USE |
CA2786314A1 (en) | 2010-02-25 | 2011-09-01 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
WO2012015715A1 (en) * | 2010-07-27 | 2012-02-02 | High Point Pharmaceuticals, Llc | Substituted thiazol-2-ylamine derivatives, pharmaceutical compositions, and methods of use as 11-beta hsd1 modulators |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
MY159058A (en) | 2011-02-25 | 2016-12-15 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agent |
CN103764672A (zh) | 2011-03-01 | 2014-04-30 | 辛纳吉制药公司 | 制备鸟苷酸环化酶c激动剂的方法 |
WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
WO2012120050A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
AR088352A1 (es) | 2011-10-19 | 2014-05-28 | Merck Sharp & Dohme | Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina |
CN103204824B (zh) * | 2012-01-12 | 2015-04-08 | 清华大学深圳研究生院 | 2-氨基噻唑-4-酰胺类衍生物及其制备方法与应用 |
RU2015106909A (ru) | 2012-08-02 | 2016-09-27 | Мерк Шарп И Доум Корп. | Антидиабетические трициклические соединения |
US9840512B2 (en) | 2013-02-22 | 2017-12-12 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
KR102272746B1 (ko) | 2013-06-05 | 2021-07-08 | 보슈 헬스 아일랜드 리미티드 | 구아닐레이트 사이클라제 c의 초순수 작용제, 및 이의 제조 및 사용 방법 |
WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
CA2959208C (en) | 2014-08-29 | 2023-09-19 | Tes Pharma S.R.L. | Pyrimidine derivatives and their use as inhibitors of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase |
CN105001152A (zh) * | 2015-07-19 | 2015-10-28 | 佛山市赛维斯医药科技有限公司 | 一类二甲胺基二吡啶叔醇结构的11β-HSD1抑制剂及其用途 |
CN105017135A (zh) * | 2015-07-19 | 2015-11-04 | 佛山市赛维斯医药科技有限公司 | 一类二吡啶叔醇结构的11β-HSD1抑制剂、制备方法及其用途 |
EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
MX2019004321A (es) | 2016-10-14 | 2019-06-12 | Tes Pharma S R L | Inhibidores de la acido alfa-amino-beta-carboximuconico semialdehido descarboxilasa. |
CN107663204A (zh) * | 2016-10-19 | 2018-02-06 | 首都医科大学附属北京世纪坛医院 | 一种化合物的抗结核应用 |
US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
EP3558298A4 (en) | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | ANTIDIABETIC SPIROCHROMAN COMPOUNDS |
US11655246B2 (en) * | 2017-11-30 | 2023-05-23 | Step Pharma S.A.S. | Aminothiazole compounds as inhibitors of CTPS1 |
WO2019106146A1 (en) | 2017-11-30 | 2019-06-06 | Step Pharma S.A.S. | Compounds |
MA51828B1 (fr) | 2018-02-15 | 2022-11-30 | Vertex Pharma | Macrocycles utilisés en tant que modulateurs du régulateur de la conductance transmembranaire de fibrose kystique, compositions pharmaceutiques de ceux-ci, leur utilisation dans le traitement de la fibrose kystique et procédé de fabrication associé |
CN108358869B (zh) * | 2018-03-27 | 2019-09-10 | 河北师范大学 | 一种n-苯并噻唑基苯磺酰胺类衍生物、制备方法及用途 |
CN108659219B (zh) * | 2018-06-08 | 2021-02-09 | 扬州大学 | 一种聚苯胺的制备方法 |
CN113302189A (zh) | 2018-11-20 | 2021-08-24 | Tes制药有限责任公司 | α-氨基-β-羧基己二烯二酸半醛去羧酶的抑制剂 |
CN109748831A (zh) * | 2018-12-17 | 2019-05-14 | 南通正达农化有限公司 | 一种三氟甲磺酸三氟乙酯的制备方法 |
EP3924058A1 (en) | 2019-02-13 | 2021-12-22 | Merck Sharp & Dohme Corp. | 5-alkyl pyrrolidine orexin receptor agonists |
WO2021026047A1 (en) | 2019-08-08 | 2021-02-11 | Merck Sharp & Dohme Corp. | Heteroaryl pyrrolidine and piperidine orexin receptor agonists |
TW202115092A (zh) | 2019-08-14 | 2021-04-16 | 美商維泰克斯製藥公司 | 囊腫纖維化跨膜傳導調節蛋白之調節劑 |
TW202120517A (zh) | 2019-08-14 | 2021-06-01 | 美商維泰克斯製藥公司 | 製備cftr調節劑之方法 |
US11873300B2 (en) | 2019-08-14 | 2024-01-16 | Vertex Pharmaceuticals Incorporated | Crystalline forms of CFTR modulators |
CN111620837B (zh) * | 2020-06-29 | 2022-02-15 | 郑州大学 | 香柏酮噻唑酰胺类化合物、及其制备方法和应用 |
CN116249697A (zh) | 2020-08-18 | 2023-06-09 | 默沙东有限责任公司 | 二环庚烷吡咯烷食欲素受体激动剂 |
EP4225750A1 (en) * | 2020-10-07 | 2023-08-16 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
CN112451514A (zh) * | 2020-11-26 | 2021-03-09 | 江西农业大学 | 二氢杨梅素纳米硒及其制备方法和应用 |
CN113461635A (zh) * | 2021-07-07 | 2021-10-01 | 上海毕得医药科技股份有限公司 | 4-(2-氯乙基)噻唑-2-羧酸乙酯及其制备方法和应用 |
AU2022330020A1 (en) * | 2021-08-20 | 2024-03-07 | Enanta Pharmaceuticals, Inc. | 17-beta-hydroxysteroid dehydrogenase type 13 inhibitors and methods of use thereof |
Family Cites Families (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB517272A (en) * | 1938-06-03 | 1940-01-25 | May & Baker Ltd | The preparation of new therapeutically useful heterocyclic compounds |
GB620654A (en) | 1939-10-03 | 1949-03-29 | Chinoin Gyogyszer Es Vegyeszet | A process for the preparation of sulphonamide derivatives of 2-amino-thiazole |
US2611770A (en) | 1949-04-16 | 1952-09-23 | American Cyanamid Co | N-(2-thiazolyl)-2-hydroxypyridine-5-sulfonamides |
GB822947A (en) | 1957-01-25 | 1959-11-04 | Smith & Nephew | Improvements in and relating to sulphonamides |
DE1620508A1 (de) | 1965-07-23 | 1969-09-18 | Thomae Gmbh Dr K | Verfahren zur Herstellung neuer 4,5,6,7-Tetrahydrothiazolo-[5,4-c]-pyridine |
CA1088049A (en) | 1975-06-03 | 1980-10-21 | Takashi Masugi | 3-substituted-7-substituted alkanamido-3-cephem-4- carboxylic acid compounds and processes for preparation thereof |
FR2384498A1 (fr) | 1975-11-26 | 1978-10-20 | Parcor | Nouveaux derives sulfonylamino thiazoliques et leurs applications en medecine humaine et veterinaire |
EP0246749A3 (en) * | 1986-05-17 | 1988-08-31 | AgrEvo UK Limited | Triazole herbicides |
US5591761A (en) | 1993-05-20 | 1997-01-07 | Texas Biotechnology Corporation | Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
US5594021A (en) | 1993-05-20 | 1997-01-14 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl sulfonamides and derivatives thereof that modulate the activity of endothelin |
US5962490A (en) * | 1987-09-25 | 1999-10-05 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
JPH021483A (ja) | 1988-03-10 | 1990-01-05 | Nippon Tokushu Noyaku Seizo Kk | 農業用殺菌剤 |
JPH078863B2 (ja) | 1989-09-21 | 1995-02-01 | 久光製薬株式会社 | 新規なジフェニルチアゾール誘導体 |
EP0532239B1 (en) | 1991-09-10 | 1995-12-13 | Zeneca Limited | Benzenesulphonamide derivatives as 5-lipoxygenase inhibitors |
JPH0670024B2 (ja) | 1993-04-13 | 1994-09-07 | 塩野義製薬株式会社 | グルタコン酸エステル誘導体の製法 |
US6030991A (en) | 1993-05-20 | 2000-02-29 | Texas Biotechnology Corp. | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
JPH07149746A (ja) * | 1993-11-30 | 1995-06-13 | Hisamitsu Pharmaceut Co Inc | 新規な2−置換アミノチアゾール誘導体 |
JPH07149745A (ja) * | 1993-11-30 | 1995-06-13 | Hisamitsu Pharmaceut Co Inc | 新規な2−アミノチアゾール誘導体 |
JPH07309757A (ja) * | 1994-05-18 | 1995-11-28 | Asahi Chem Ind Co Ltd | βアミロイド蛋白神経細胞毒性低減剤 |
WO1996004912A1 (en) | 1994-08-09 | 1996-02-22 | Metabolic Syndrome I Gbg Ab | Use of ketoconazole and related substances in medicaments for treatment of type ii diabetes |
AU689972B2 (en) * | 1994-11-29 | 1998-04-09 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/or salt thereof |
SE505391C2 (sv) | 1995-05-30 | 1997-08-18 | Cortendo Ab | Användning av kortisol-agonister för framställning av ett system för diagnostisering av det metabola syndromet |
GB9512697D0 (en) | 1995-06-22 | 1995-08-23 | Zeneca Ltd | Heterocyclic compounds |
GB9517622D0 (en) | 1995-08-29 | 1995-11-01 | Univ Edinburgh | Regulation of intracellular glucocorticoid concentrations |
WO1997047299A1 (en) * | 1996-06-12 | 1997-12-18 | 3-Dimensional Pharmaceuticals, Inc. | Amidino and guanidino heterocyclic protease inhibitors |
US5877193A (en) | 1996-07-19 | 1999-03-02 | Hoffmann-La Roche Inc. | Use of N-(4-aryl-thiazol-2-yl)-sulfonamides |
AU743898B2 (en) | 1996-10-16 | 2002-02-07 | American Cyanamid Company | The preparation and use of ortho-sulfonamido heteroaryl hydroxamic acids as matrix metalloproteinase and tace inhibitors |
DZ2376A1 (fr) | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
SE9700642D0 (sv) | 1997-02-24 | 1997-02-24 | Kronvall Stefan Med Ab | Medel och sätt för förebyggande och behandling av det metabola syndromet |
US5783597A (en) * | 1997-03-04 | 1998-07-21 | Ortho Pharmaceutical Corporation | 2,5-disubstituted thiophenes: inhibitors of 5-lipoxygenase and inducible cyclooxygenase (COX-2) enzymes, composition and use |
EP0994862B1 (en) | 1997-07-11 | 2005-06-01 | SmithKline Beecham plc | Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation |
GB9725141D0 (en) * | 1997-11-27 | 1998-01-28 | Pharmacia & Upjohn Spa | Benzenesulfonamide compounds |
AU768751B2 (en) | 1998-06-18 | 2004-01-08 | Bristol-Myers Squibb Company | Carbon substituted aminothiazole inhibitors of cyclin dependent kinases |
CN1332943C (zh) | 1998-07-08 | 2007-08-22 | 萨诺费-阿文蒂斯德国有限公司 | 硫取代的磺酰基氨基羧酸n-芳基酰胺,其制备方法、用途以及含有该化合物的药物制剂 |
GB9915625D0 (en) | 1999-07-02 | 1999-09-01 | Cortendo Ab | Method |
GB0001449D0 (en) | 2000-01-21 | 2000-03-08 | Cortendo Ab | Compositions |
IT1317735B1 (it) | 2000-01-26 | 2003-07-15 | Nicox Sa | Sali di agenti antimicrobici. |
SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
WO2002028353A2 (en) | 2000-10-05 | 2002-04-11 | Smithkline Beecham Corporation | Phosphate transport inhibitors |
GB0118300D0 (en) | 2001-07-26 | 2001-09-19 | Cortendo Ab | Formulations |
EA200400709A1 (ru) | 2001-11-22 | 2004-12-30 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
EA200400707A1 (ru) | 2001-11-22 | 2004-10-28 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
EP1461325B1 (en) | 2001-11-22 | 2010-05-26 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
EA200400708A1 (ru) | 2001-11-22 | 2004-10-28 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
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