CA2377087A1 - Indanyl-substituted benzole carbonamide, method for the production of the same, use thereof as a medicament and pharmaceutical preparations containing the same - Google Patents
Indanyl-substituted benzole carbonamide, method for the production of the same, use thereof as a medicament and pharmaceutical preparations containing the same Download PDFInfo
- Publication number
- CA2377087A1 CA2377087A1 CA002377087A CA2377087A CA2377087A1 CA 2377087 A1 CA2377087 A1 CA 2377087A1 CA 002377087 A CA002377087 A CA 002377087A CA 2377087 A CA2377087 A CA 2377087A CA 2377087 A1 CA2377087 A1 CA 2377087A1
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- hydrogen
- alkyl
- methyl
- formula
- 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.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 206010003658 Atrial Fibrillation Diseases 0.000 claims abstract description 13
- 239000003416 antiarrhythmic agent Substances 0.000 claims abstract description 12
- 238000011321 prophylaxis Methods 0.000 claims abstract description 11
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 230000003213 activating effect Effects 0.000 claims abstract description 7
- 230000003111 delayed effect Effects 0.000 claims abstract description 7
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims abstract description 6
- 206010003662 Atrial flutter Diseases 0.000 claims abstract description 6
- 210000002837 heart atrium Anatomy 0.000 claims abstract description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 5
- 239000011591 potassium Substances 0.000 claims abstract description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 147
- -1 1-indanyl radical Chemical class 0.000 claims description 135
- 229910052739 hydrogen Inorganic materials 0.000 claims description 121
- 239000001257 hydrogen Substances 0.000 claims description 121
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 83
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 12
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- 125000002541 furyl group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 8
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 8
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- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 8
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
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- 150000003254 radicals Chemical class 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- 206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 3
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- 238000007112 amidation reaction Methods 0.000 claims description 2
- 239000002876 beta blocker Substances 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims 6
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- 239000004480 active ingredient Substances 0.000 abstract description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
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- 108091006146 Channels Proteins 0.000 description 9
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000007429 general method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229940124530 sulfonamide Drugs 0.000 description 8
- 150000003456 sulfonamides Chemical class 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
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- LMRKXSDOAFUINK-UHFFFAOYSA-N 3-chlorosulfonylbenzoic acid Chemical class OC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 LMRKXSDOAFUINK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
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- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 3
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical compound C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 102000004257 Potassium Channel Human genes 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- FPQVGDGSRVMNMR-JCTPKUEWSA-N [[(z)-(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy-(dimethylamino)methylidene]-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCOC(=O)C(\C#N)=N/OC(N(C)C)=[N+](C)C FPQVGDGSRVMNMR-JCTPKUEWSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 108020001213 potassium channel Proteins 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
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- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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- 230000000903 blocking effect Effects 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
- C07C311/26—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19929076A DE19929076A1 (de) | 1999-06-25 | 1999-06-25 | Indanylsubstituierte Benzolcarbonamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| DE19929076.8 | 1999-06-25 | ||
| PCT/EP2000/005370 WO2001000573A1 (de) | 1999-06-25 | 2000-06-10 | Indanylsubstituierte benzolcarbonamide, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltende pharmazeutische zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2377087A1 true CA2377087A1 (en) | 2001-01-04 |
Family
ID=7912468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002377087A Abandoned CA2377087A1 (en) | 1999-06-25 | 2000-06-10 | Indanyl-substituted benzole carbonamide, method for the production of the same, use thereof as a medicament and pharmaceutical preparations containing the same |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6221866B1 (enExample) |
| EP (1) | EP1194403B1 (enExample) |
| JP (1) | JP4527918B2 (enExample) |
| KR (1) | KR20020023962A (enExample) |
| CN (1) | CN1157372C (enExample) |
| AR (1) | AR024443A1 (enExample) |
| AT (1) | ATE248811T1 (enExample) |
| AU (1) | AU771601B2 (enExample) |
| BR (1) | BR0011938A (enExample) |
| CA (1) | CA2377087A1 (enExample) |
| CZ (1) | CZ20014523A3 (enExample) |
| DE (2) | DE19929076A1 (enExample) |
| DK (1) | DK1194403T3 (enExample) |
| EE (1) | EE04464B1 (enExample) |
| ES (1) | ES2200886T3 (enExample) |
| HK (1) | HK1047575B (enExample) |
| HU (1) | HUP0201711A3 (enExample) |
| IL (1) | IL147220A0 (enExample) |
| MX (1) | MXPA01012281A (enExample) |
| NO (1) | NO20015816D0 (enExample) |
| NZ (1) | NZ516347A (enExample) |
| PL (1) | PL352985A1 (enExample) |
| PT (1) | PT1194403E (enExample) |
| RU (1) | RU2238934C2 (enExample) |
| SI (1) | SI1194403T1 (enExample) |
| SK (1) | SK19092001A3 (enExample) |
| TR (1) | TR200103701T2 (enExample) |
| TW (1) | TWI256950B (enExample) |
| WO (1) | WO2001000573A1 (enExample) |
| YU (1) | YU88801A (enExample) |
| ZA (1) | ZA200109732B (enExample) |
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|---|---|---|---|---|
| US6970362B1 (en) | 2000-07-31 | 2005-11-29 | Intel Corporation | Electronic assemblies and systems comprising interposer with embedded capacitors |
| US6775150B1 (en) | 2000-08-30 | 2004-08-10 | Intel Corporation | Electronic assembly comprising ceramic/organic hybrid substrate with embedded capacitors and methods of manufacture |
| US6586421B2 (en) | 2000-09-20 | 2003-07-01 | Pharmacia & Upjohn Company | Substituted azepino[4,5b]indoline derivatives |
| DE10121002A1 (de) * | 2001-04-28 | 2002-11-14 | Aventis Pharma Gmbh | Verwendung von Anthranilsäureamiden als Medikament zur Behandlung von Arrhythmien sowie sie enthaltende pharmazeutische Zubereitungen |
| DE10121003A1 (de) | 2001-04-28 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide, Verfahren zur Herstellung, ihrer Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| US7119112B2 (en) * | 2002-02-28 | 2006-10-10 | Icagen, Inc. | Sulfonamides as potassium channel blockers |
| ATE524452T1 (de) | 2003-03-27 | 2011-09-15 | Cytokinetics Inc | Sulfonamide zur behandlung von kongestivem herzversagen, deren zusammensetzungen und verwendungen. |
| GB0315950D0 (en) | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
| US7368582B2 (en) | 2003-10-17 | 2008-05-06 | Solvay Pharmaceuticals Gmbh | Amidomethyl-substituted 2-(4-sulfonylamino)-3-hydroxy-3,4-dihydro-2H-chromen-6-yl compounds, a process and intermediates for their production, and pharmaceutical compositions containing them |
| GB0412986D0 (en) | 2004-06-10 | 2004-07-14 | Xention Discovery Ltd | Compounds |
| US7569589B2 (en) | 2004-07-29 | 2009-08-04 | Merck & Co., Inc. | Potassium channel inhibitors |
| US7576212B2 (en) | 2004-12-09 | 2009-08-18 | Xention Limited | Thieno[2,3-B] pyridines as potassium channel inhibitors |
| DE102005028845A1 (de) * | 2005-06-22 | 2006-12-28 | Sanofi-Aventis Deutschland Gmbh | Substituierte Heterocyclen, ihre Verwendung als Medikament sowie enthaltende pharmazeutische Zubereitungen |
| EP1917979A4 (en) * | 2005-08-23 | 2009-06-03 | Astellas Pharma Inc | THERAPEUTICS FOR PREVIOUS LIVING ROOMS |
| GB0525164D0 (en) | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| NZ572231A (en) * | 2006-04-27 | 2010-12-24 | Sanofi Aventis Deutschland | Inhibitors of the task-1 and task-3 ion channel |
| US7935715B2 (en) | 2006-07-28 | 2011-05-03 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
| EA200900403A1 (ru) | 2006-09-25 | 2009-10-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Соединения, которые модулируют рецептор св2 |
| WO2008098025A1 (en) * | 2007-02-08 | 2008-08-14 | Boehringer Ingelheim International Gmbh | Arylsulfonamide compounds which modulate the cb2 receptor |
| JP4891111B2 (ja) * | 2007-02-16 | 2012-03-07 | 富士フイルム株式会社 | ズームレンズ |
| CA2681572C (en) | 2007-03-23 | 2014-02-11 | Icagen, Inc. | Inhibitors of ion channels |
| WO2009061652A1 (en) * | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| WO2010005782A1 (en) * | 2008-07-10 | 2010-01-14 | Boehringer Ingelheim International Gmbh | Sulfone compounds which modulate the cb2 receptor |
| GB0815782D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815781D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815784D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| KR20110063438A (ko) | 2008-09-25 | 2011-06-10 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｃｂ2 수용체를 선택적으로 조절하는 설포닐 화합물 |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| WO2010147791A1 (en) | 2009-06-16 | 2010-12-23 | Boehringer Ingelheim International Gmbh | Azetidine 2 -carboxamide derivatives which modulate the cb2 receptor |
| US8383651B2 (en) * | 2009-09-22 | 2013-02-26 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| JP2013517271A (ja) | 2010-01-15 | 2013-05-16 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体を調節する化合物 |
| WO2011109324A1 (en) | 2010-03-05 | 2011-09-09 | Boehringer Ingelheim International Gmbh | Tetrazole compounds which selectively modulate the cb2 receptor |
| JP5746764B2 (ja) | 2010-07-22 | 2015-07-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体を調節する化合物 |
| GB201105659D0 (en) | 2011-04-01 | 2011-05-18 | Xention Ltd | Compounds |
| NO3175985T3 (enExample) | 2011-07-01 | 2018-04-28 | ||
| HK1201455A1 (en) | 2012-01-27 | 2015-09-04 | Gilead Sciences Inc | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| EP3366683A1 (en) * | 2017-02-28 | 2018-08-29 | Acousia Therapeutics GmbH | Cyclic amides, acteamides and ureas useful as potassium channel openers |
| EP4446314A3 (en) * | 2019-05-03 | 2025-03-12 | Praxis Precision Medicines, Inc. | Kcnt1 inhibitors and methods of use |
| US11773088B2 (en) | 2020-11-02 | 2023-10-03 | Praxis Precision Medicines, Inc. | KCNT1 inhibitors and methods of use |
| WO2023211855A1 (en) * | 2022-04-25 | 2023-11-02 | Praxis Precision Medicines, Inc. | Kcnt1 inhibitors comprising a thiophene core and methods of use |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5234944A (en) | 1986-08-21 | 1993-08-10 | Roussel Uclaf | Novel indanes |
| ES2052593T3 (es) | 1986-08-21 | 1994-07-16 | Roussel Uclaf | Procedimiento para preparar derivados del indano. |
| DK626889A (da) | 1988-12-16 | 1990-06-17 | Roussel Uclaf | Indanderivater, deres fremstilling samt laegemidler med indhold deraf |
| US5348971A (en) | 1988-12-16 | 1994-09-20 | Roussel Uclaf | Indanes useful as analgesics |
| RU2043337C1 (ru) * | 1990-07-20 | 1995-09-10 | Институт биохимии Литовской АН | Способ получения 5-аргиниламинонафталин-1-сульфамидов |
| FR2708608B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés de N-sulfonylbenzimidazolone, leur préparation, les compositions pharmaceutiques en contenant. |
| AU1867095A (en) * | 1994-01-10 | 1995-08-01 | Technion Research & Development Foundation Ltd. | 1-aminoindan derivatives and compositions thereof |
| US5877218A (en) | 1994-01-10 | 1999-03-02 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using 1-aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
| US6083986A (en) * | 1996-07-26 | 2000-07-04 | Icagen, Inc. | Potassium channel inhibitors |
| DE19707656A1 (de) * | 1997-02-26 | 1998-08-27 | Hoechst Ag | Sulfonamid-substituierte anellierte 7-Ring-Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
| CN1273579A (zh) * | 1997-08-05 | 2000-11-15 | 美国家用产品公司 | 氨茴酸类似物 |
| DE19749453A1 (de) * | 1997-11-10 | 1999-05-12 | Hoechst Marion Roussel De Gmbh | Sulfonamid-substituierte anellierte 5-Ring-Verbindungen, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
-
1999
- 1999-06-25 DE DE19929076A patent/DE19929076A1/de not_active Withdrawn
-
2000
- 2000-06-10 PT PT00940359T patent/PT1194403E/pt unknown
- 2000-06-10 BR BR0011938-5A patent/BR0011938A/pt not_active IP Right Cessation
- 2000-06-10 TR TR2001/03701T patent/TR200103701T2/xx unknown
- 2000-06-10 CA CA002377087A patent/CA2377087A1/en not_active Abandoned
- 2000-06-10 ES ES00940359T patent/ES2200886T3/es not_active Expired - Lifetime
- 2000-06-10 NZ NZ516347A patent/NZ516347A/xx unknown
- 2000-06-10 IL IL14722000A patent/IL147220A0/xx unknown
- 2000-06-10 AU AU55318/00A patent/AU771601B2/en not_active Ceased
- 2000-06-10 HK HK02108652.0A patent/HK1047575B/zh not_active IP Right Cessation
- 2000-06-10 DK DK00940359T patent/DK1194403T3/da active
- 2000-06-10 MX MXPA01012281A patent/MXPA01012281A/es unknown
- 2000-06-10 CN CNB008094500A patent/CN1157372C/zh not_active Expired - Fee Related
- 2000-06-10 HU HU0201711A patent/HUP0201711A3/hu unknown
- 2000-06-10 YU YU88801A patent/YU88801A/sh unknown
- 2000-06-10 PL PL00352985A patent/PL352985A1/xx not_active Application Discontinuation
- 2000-06-10 CZ CZ20014523A patent/CZ20014523A3/cs unknown
- 2000-06-10 JP JP2001506984A patent/JP4527918B2/ja not_active Expired - Fee Related
- 2000-06-10 DE DE50003555T patent/DE50003555D1/de not_active Expired - Lifetime
- 2000-06-10 EE EEP200100684A patent/EE04464B1/xx not_active IP Right Cessation
- 2000-06-10 RU RU2002101723/04A patent/RU2238934C2/ru not_active IP Right Cessation
- 2000-06-10 WO PCT/EP2000/005370 patent/WO2001000573A1/de not_active Ceased
- 2000-06-10 KR KR1020017016458A patent/KR20020023962A/ko not_active Ceased
- 2000-06-10 SI SI200030224T patent/SI1194403T1/xx unknown
- 2000-06-10 EP EP00940359A patent/EP1194403B1/de not_active Expired - Lifetime
- 2000-06-10 SK SK1909-2001A patent/SK19092001A3/sk unknown
- 2000-06-10 AT AT00940359T patent/ATE248811T1/de not_active IP Right Cessation
- 2000-06-22 AR ARP000103128A patent/AR024443A1/es unknown
- 2000-06-22 TW TW089112238A patent/TWI256950B/zh not_active IP Right Cessation
- 2000-06-23 US US09/603,436 patent/US6221866B1/en not_active Expired - Fee Related
-
2001
- 2001-11-27 ZA ZA200109732A patent/ZA200109732B/en unknown
- 2001-11-29 NO NO20015816A patent/NO20015816D0/no not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |