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 |
| JP5030587B2 (ja) | 2003-06-26 | 2012-09-19 | バイオトロン・リミテッド | 抗ウイルスアシルグアニジン化合物および方法 |
| 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 |
| 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 |
| US6891069B1 (en) | 2004-01-30 | 2005-05-10 | Ethicon, Inc. | Synthesis of 4-substituted phthalaldehyde |
| 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 |
| 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 |
| MX381407B (es) | 2008-12-31 | 2025-03-12 | Ardelyx Inc | Compuestos y métodos para inhibir el antiporte mediado por intercambiador de iones de sodio/iones de hidrógeno (nhe) en el tratamiento de trastornos asociados con retención de fluido o sobrecarga de sal y trastornos del tracto gastrointestinal. |
| 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 |
| HRP20191000T1 (hr) | 2013-04-12 | 2019-09-20 | Ardelyx, Inc. | Spojevi za vezanje nhe3 i metode inhibiranja transporta fosfata |
| MX395405B (es) | 2017-01-09 | 2025-03-25 | Ardelyx Inc | Compuestos útiles para tratar trastornos del tracto gastrointestinal. |
| MX2019008171A (es) | 2017-01-09 | 2020-02-05 | Ardelyx Inc | Inhibidores del antiporte mediado por nhe. |
| 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 |
| EP3890745B1 (en) | 2018-12-04 | 2025-11-19 | President and Fellows of Harvard College | Synthetic derivatives of cholic acid 7-sulfate and uses thereof |
| KR20250171471A (ko) | 2019-05-10 | 2025-12-08 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 장 박테리아 담즙산 대사의 소분자 조정제 |
| EP4706758A3 (en) | 2019-05-21 | 2026-05-06 | Ardelyx, Inc. | Methods for inhibiting phosphate transport |
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 CN CN99812751A patent/CN1325403A/zh active Pending
- 1999-10-15 RU RU2001114207/04A patent/RU2232769C2/ru not_active IP Right Cessation
- 1999-10-15 ES ES99949001T patent/ES2191466T3/es not_active Expired - Lifetime
- 1999-10-15 PT PT99949001T patent/PT1124841E/pt unknown
- 1999-10-15 EP EP99949001A patent/EP1124841B1/de not_active Expired - Lifetime
- 1999-10-15 BR BR9914929-0A patent/BR9914929A/pt not_active IP Right Cessation
- 1999-10-15 ID IDW00200100935A patent/ID29025A/id unknown
- 1999-10-15 AT AT99949001T patent/ATE236191T1/de not_active IP Right Cessation
- 1999-10-15 DK DK99949001T patent/DK1124841T3/da active
- 1999-10-15 CZ CZ20011429A patent/CZ20011429A3/cs unknown
- 1999-10-15 CA CA002349523A patent/CA2349523A1/en not_active Abandoned
- 1999-10-15 HU HU0103751A patent/HUP0103751A3/hu unknown
- 1999-10-15 TR TR2001/01163T patent/TR200101163T2/xx unknown
- 1999-10-15 HK HK02102812.0A patent/HK1041271A1/zh unknown
- 1999-10-15 DE DE59904875T patent/DE59904875D1/de not_active Expired - Lifetime
- 1999-10-15 AU AU62032/99A patent/AU757365B2/en not_active Ceased
- 1999-10-15 WO PCT/EP1999/007828 patent/WO2000024761A1/de not_active Ceased
- 1999-10-15 PL PL99348108A patent/PL348108A1/xx unknown
- 1999-10-15 KR KR1020017005343A patent/KR20010085973A/ko not_active Abandoned
- 1999-10-15 JP JP2000578331A patent/JP4616479B2/ja not_active Expired - Fee Related
- 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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