JP2002528460A5 - - Google Patents
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- Publication number
- JP2002528460A5 JP2002528460A5 JP2000578331A JP2000578331A JP2002528460A5 JP 2002528460 A5 JP2002528460 A5 JP 2002528460A5 JP 2000578331 A JP2000578331 A JP 2000578331A JP 2000578331 A JP2000578331 A JP 2000578331A JP 2002528460 A5 JP2002528460 A5 JP 2002528460A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- phenyl
- substituted
- benzyl
- 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
- 239000001257 hydrogen Substances 0.000 description 34
- 229910052739 hydrogen Inorganic materials 0.000 description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 description 3
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 0 *C(C(N=C(N)N)=O)=C Chemical compound *C(C(N=C(N)N)=O)=C 0.000 description 1
- OCODJNASCDFXSR-UHFFFAOYSA-N 1-bromo-2-fluoro-4-iodobenzene Chemical compound FC1=CC(I)=CC=C1Br OCODJNASCDFXSR-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- KXAFBSGUPWDXCS-UHFFFAOYSA-N butyl 3-(4-bromo-3-fluorophenyl)-2-methylprop-2-enoate Chemical compound CCCCOC(=O)C(C)=CC1=CC=C(Br)C(F)=C1 KXAFBSGUPWDXCS-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 201000001883 cholelithiasis Diseases 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- -1 di-o-tolylphosphino Chemical group 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 208000001130 gallstones Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19849722A DE19849722A1 (de) | 1998-10-28 | 1998-10-28 | Substituierte Phenyl-alkenoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19849722.9 | 1998-10-28 | ||
| PCT/EP1999/007828 WO2000024761A1 (de) | 1998-10-28 | 1999-10-15 | Gallensauer substituierte phenyl-alkenoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikamente oder diagnostika sowie sie enthaltendes medikament |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002528460A JP2002528460A (ja) | 2002-09-03 |
| JP2002528460A5 true JP2002528460A5 (https=) | 2006-11-16 |
| JP4616479B2 JP4616479B2 (ja) | 2011-01-19 |
Family
ID=7885948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000578331A Expired - Fee Related JP4616479B2 (ja) | 1998-10-28 | 1999-10-15 | 胆汁酸で置換されたフェニルアルケノイルグアニジン類、その製造方法、その薬剤または診断薬としての使用、およびそれらを含有する薬剤 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6166002A (https=) |
| EP (1) | EP1124841B1 (https=) |
| JP (1) | JP4616479B2 (https=) |
| KR (1) | KR20010085973A (https=) |
| CN (1) | CN1325403A (https=) |
| AT (1) | ATE236191T1 (https=) |
| AU (1) | AU757365B2 (https=) |
| BR (1) | BR9914929A (https=) |
| CA (1) | CA2349523A1 (https=) |
| CZ (1) | CZ20011429A3 (https=) |
| DE (2) | DE19849722A1 (https=) |
| DK (1) | DK1124841T3 (https=) |
| ES (1) | ES2191466T3 (https=) |
| HK (1) | HK1041271A1 (https=) |
| HU (1) | HUP0103751A3 (https=) |
| ID (1) | ID29025A (https=) |
| PL (1) | PL348108A1 (https=) |
| PT (1) | PT1124841E (https=) |
| RU (1) | RU2232769C2 (https=) |
| TR (1) | TR200101163T2 (https=) |
| WO (1) | WO2000024761A1 (https=) |
| ZA (1) | ZA200103106B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP2617709B8 (en) | 2003-06-26 | 2022-12-21 | Biotron Limited | Guanidine derivatives as antiviral agents |
| DE10338554A1 (de) * | 2003-08-22 | 2005-03-31 | Aventis Pharma Deutschland Gmbh | Pentafluorosulfanylphenyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US20050171215A1 (en) * | 2004-01-30 | 2005-08-04 | Ethicon, Inc. | Germicidal compositions containing halogenated phthalaldehyes, and methods of using such compositions for disinfection or sterilization |
| US6891069B1 (en) | 2004-01-30 | 2005-05-10 | Ethicon, Inc. | Synthesis of 4-substituted phthalaldehyde |
| US7476767B2 (en) | 2004-01-30 | 2009-01-13 | Ethicon, Inc. | Alpha-hydroxy sulfonate aldehydes, germicidal compositions containing the alpha-hydroxy sulfonate aldehydes, or mixtures of alpha-hydroxy sulfonate aldehydes and phthalaldehydes, and methods of using the compounds or compositions for disinfection or sterilization |
| US7390837B2 (en) | 2004-01-30 | 2008-06-24 | Ethicon, Inc. | Germicidal compositions containing phenylmalonaldehyde-type compounds, or mixtures of phenylmalonaldehyde-type compounds and phthalaldehydes, and methods of using such compositions for disinfection or sterilization |
| US7291649B2 (en) | 2005-06-29 | 2007-11-06 | Ethicon, Inc. | Forming germicidal aromatic dialdehydes with acetals |
| CZ301037B6 (cs) * | 2007-09-06 | 2009-10-21 | Vysoká škola chemicko-technologická v Praze | Amidové konjugáty steroidních a žlucových kyselin s D-glukosaminem a zpusob jejich prípravy |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | 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 |
| SI2384318T1 (en) | 2008-12-31 | 2018-03-30 | Ardelyx, Inc. | MEASURES AND PROCEDURES FOR THE INHIBITION OF ANTIPORT INHIBITED BY NHE IN THE TREATMENT OF DISEASES RELATED TO STRENGTH OF FLAMMABILITY OR TRADEMARITY WITH SOLO, AND THE EMISSION OF GASTROINTESTINAL TREATMENT |
| LT2983667T (lt) | 2013-04-12 | 2019-07-10 | Ardelyx, Inc. | Nhe3 rišantys junginiai ir fosfato pernešimo slopinimo būdai |
| EA201991676A1 (ru) | 2017-01-09 | 2020-01-30 | Арделикс, Инк. | Ингибиторы nhe-опосредованного антипорта |
| CA3049678A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds useful for treating gastrointestinal tract disorders |
| US12186329B2 (en) | 2018-08-23 | 2025-01-07 | President And Fellows Of Harvard College | Compositions and methods related to cholic acid 7-sulfate as a treatment for diabetes |
| WO2020117945A1 (en) | 2018-12-04 | 2020-06-11 | President And Fellows Of Harvard College | Synthetic derivatives of cholic acid 7-sulfate and uses thereof |
| AU2020274319B2 (en) | 2019-05-10 | 2026-02-12 | President And Fellows Of Harvard College | Small molecule modulators of gut bacterial bile acid metabolism |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW289021B (https=) * | 1993-05-08 | 1996-10-21 | Hoechst Ag | |
| US5792635A (en) * | 1995-06-07 | 1998-08-11 | Magainin Pharmaceuticals, Inc. | Method of inhibiting the sodium/proton exchanger NHE3 and method of inhibiting growth by administering squalamine |
| JPH0959162A (ja) * | 1995-08-28 | 1997-03-04 | Makoto Takahashi | 胆石溶解剤 |
| 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 |
-
1998
- 1998-10-28 DE DE19849722A patent/DE19849722A1/de not_active Withdrawn
-
1999
- 1999-10-15 ID IDW00200100935A patent/ID29025A/id unknown
- 1999-10-15 BR BR9914929-0A patent/BR9914929A/pt not_active IP Right Cessation
- 1999-10-15 AT AT99949001T patent/ATE236191T1/de not_active IP Right Cessation
- 1999-10-15 HK HK02102812.0A patent/HK1041271A1/zh unknown
- 1999-10-15 WO PCT/EP1999/007828 patent/WO2000024761A1/de not_active Ceased
- 1999-10-15 DE DE59904875T patent/DE59904875D1/de not_active Expired - Lifetime
- 1999-10-15 PT PT99949001T patent/PT1124841E/pt unknown
- 1999-10-15 TR TR2001/01163T patent/TR200101163T2/xx unknown
- 1999-10-15 KR KR1020017005343A patent/KR20010085973A/ko not_active Abandoned
- 1999-10-15 AU AU62032/99A patent/AU757365B2/en not_active Ceased
- 1999-10-15 DK DK99949001T patent/DK1124841T3/da active
- 1999-10-15 PL PL99348108A patent/PL348108A1/xx unknown
- 1999-10-15 RU RU2001114207/04A patent/RU2232769C2/ru not_active IP Right Cessation
- 1999-10-15 CN CN99812751A patent/CN1325403A/zh active Pending
- 1999-10-15 EP EP99949001A patent/EP1124841B1/de not_active Expired - Lifetime
- 1999-10-15 CA CA002349523A patent/CA2349523A1/en not_active Abandoned
- 1999-10-15 JP JP2000578331A patent/JP4616479B2/ja not_active Expired - Fee Related
- 1999-10-15 CZ CZ20011429A patent/CZ20011429A3/cs unknown
- 1999-10-15 HU HU0103751A patent/HUP0103751A3/hu unknown
- 1999-10-15 ES ES99949001T patent/ES2191466T3/es not_active Expired - Lifetime
- 1999-10-20 US US09/422,146 patent/US6166002A/en not_active Expired - Lifetime
-
2001
- 2001-04-17 ZA ZA200103106A patent/ZA200103106B/xx unknown
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