JP2007518683A5 - - Google Patents
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- JP2007518683A5 JP2007518683A5 JP2006519251A JP2006519251A JP2007518683A5 JP 2007518683 A5 JP2007518683 A5 JP 2007518683A5 JP 2006519251 A JP2006519251 A JP 2006519251A JP 2006519251 A JP2006519251 A JP 2006519251A JP 2007518683 A5 JP2007518683 A5 JP 2007518683A5
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- Prior art keywords
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- lower alkyl
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- 125000005843 halogen group Chemical group 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 10
- 239000011780 sodium chloride Substances 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- -1 methylenedioxy group Chemical group 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- XTNGUQKDFGDXSJ-ZXGKGEBGSA-N canagliflozin Chemical compound CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=C(F)C=C1 XTNGUQKDFGDXSJ-ZXGKGEBGSA-N 0.000 claims 2
- MCGHXGVCRJMDGV-RQXATKFSSA-N (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-[4-methyl-3-[(5-pyrimidin-2-ylthiophen-2-yl)methyl]phenyl]oxane-3,4,5-triol Chemical compound CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=NC=CC=N1 MCGHXGVCRJMDGV-RQXATKFSSA-N 0.000 claims 1
- KVGGOLXDOKXGAG-PHNZBSFLSA-N (2S,3R,4R,5S,6R)-2-[3-[[5-(6-fluoropyridin-2-yl)thiophen-2-yl]methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=CC(F)=N1 KVGGOLXDOKXGAG-PHNZBSFLSA-N 0.000 claims 1
- YISFGYUZHWGMKL-ZXGKGEBGSA-N (2S,3R,4R,5S,6R)-2-[3-[[5-[3-(difluoromethyl)phenyl]thiophen-2-yl]methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=CC(C(F)F)=C1 YISFGYUZHWGMKL-ZXGKGEBGSA-N 0.000 claims 1
- IQSVDTSKWALKNG-IFPLKCGESA-N (2S,3R,4R,5S,6R)-2-[4-chloro-3-[(5-phenylthiophen-2-yl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2SC(=CC=2)C=2C=CC=CC=2)=C1 IQSVDTSKWALKNG-IFPLKCGESA-N 0.000 claims 1
- IQUCKCHHTGLTSD-PKOFMYQESA-N (2S,3R,4R,5S,6R)-2-[4-chloro-3-[(5-pyrimidin-2-ylthiophen-2-yl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2SC(=CC=2)C=2N=CC=CN=2)=C1 IQUCKCHHTGLTSD-PKOFMYQESA-N 0.000 claims 1
- MKVKQJLSYHSXQR-QSWMPLQWSA-N (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[5-(1,3-thiazol-5-yl)thiophen-2-yl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2SC(=CC=2)C=2SC=NC=2)=C1 MKVKQJLSYHSXQR-QSWMPLQWSA-N 0.000 claims 1
- OWXVLYMIZSXRHK-OSKXVONFSA-N (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[5-(6-fluoropyridin-2-yl)thiophen-2-yl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2SC(=CC=2)C=2N=C(F)C=CC=2)=C1 OWXVLYMIZSXRHK-OSKXVONFSA-N 0.000 claims 1
- WQWNUPFPUXHKAQ-OSKXVONFSA-N (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[5-(6-fluoropyridin-3-yl)thiophen-2-yl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2SC(=CC=2)C=2C=NC(F)=CC=2)=C1 WQWNUPFPUXHKAQ-OSKXVONFSA-N 0.000 claims 1
- AHTWRVCJARAYAD-ZXGKGEBGSA-N 3-[5-[[2-chloro-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]thiophen-2-yl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2SC(=CC=2)C=2C=C(C=CC=2)C#N)=C1 AHTWRVCJARAYAD-ZXGKGEBGSA-N 0.000 claims 1
- UGTXWVQQXOWOIZ-ZXGKGEBGSA-N 4-[5-[[2-chloro-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]thiophen-2-yl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2SC(=CC=2)C=2C=CC(=CC=2)C#N)=C1 UGTXWVQQXOWOIZ-ZXGKGEBGSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 230000000887 hydrating Effects 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N iodine atom Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 1
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 0 B*(C(*)(CCCCCC1)C*1[C@@]([C@@]([C@]1O)O)OC(CO)[C@@]1O)C1=CC=CC=CC=CC=C1 Chemical compound B*(C(*)(CCCCCC1)C*1[C@@]([C@@]([C@]1O)O)OC(CO)[C@@]1O)C1=CC=CC=CC=CC=C1 0.000 description 2
Claims (13)
- 式I:
(式中、環Aは、
であり、ここでR1a、R2a、R3a、R1b、R2b、およびR3bは、それぞれ独立して、水素原子、ハロゲン原子、低級アルキル基、ハロ低級アルキル基、低級アルコキシ基、またはフェニル基であり;
環Bは、
であり、ここでR4aは、ハロゲン原子、シアノ基、低級アルキル基、ハロ低級アルキル基、低級アルコキシ基、ハロ低級アルコキシ基、メチレンジオキシ基、エチレンオキシ基、またはモノ−もしくはジ−低級アルキルアミノ基で置換されたフェニル基;またはハロゲン原子、シアノ基、低級アルキル基、もしくは低級アルコキシ基で置換されたヘテロシクリル基であり、R5aは水素原子であり;
Xは炭素原子であり;
Yは、−(CH2)n−(ここで、nは1または2である)である)
で示される化合物、またはその医薬的に許容しうる塩。 - R4aが、ハロゲン原子、シアノ基、低級アルキル基、ハロ低級アルキル基、低級アルコキシ基、もしくはハロ低級アルコキシ基で置換されたフェニル基;または、ハロゲン原子、シアノ基、低級アルキル基、もしくは低級アルコキシ基で置換されたヘテロシクリル基である、請求項2記載の化合物、またはその医薬的に許容しうる塩。
- ヘテロシクリル基が窒素原子、酸素原子および硫黄原子からなる群より独立して選ばれるヘテロ原子を1または2個含む5または6員のヘテロシクリル基である、請求項1、2、3、または4記載の化合物、またはその医薬的に許容しうる塩。
- ヘテロシクリル基がチエニル基、ピリジル基、ピリミジニル基、ピラジニル基、ピラゾリル基、チアゾリル基、キノリル基またはテトラゾリル基である、請求項1、2、3、または4記載の化合物、またはその医薬的に許容しうる塩。
- 化合物が、
1−(β−D−グルコピラノシル)−4−クロロ−3−[5-(5−チアゾリル)−2−チエニルメチル]ベンゼン;
1−(β−D−グルコピラノシル)−4−クロロ−3−(5−フェニル−2−チエニルメチル)ベンゼン;
1−(β−D−グルコピラノシル)−4−メチル−3−[5-(4−フルオロフェニル)−2−チエニルメチル]ベンゼン;
1−(β−D−グルコピラノシル)−4−クロロ−3−[5-(2−ピリミジニル)−2−チエニルメチル]ベンゼン;
1−(β−D−グルコピラノシル)−4−メチル−3−[5-(2−ピリミジニル)−2−チエニルメチル]ベンゼン;
1−(β−D−グルコピラノシル)−4−クロロ−3−[5-(3−シアノフェニル)−2−チエニルメチル]ベンゼン;
1−(β−D−グルコピラノシル)−4−クロロ−3−[5-(4−シアノフェニル)−2−チエニルメチル]ベンゼン;
1−(β−D−グルコピラノシル)−4−メチル−3−[5-(6−フルオロ−2−ピリジル)−2−チエニルメチル]ベンゼン;
1−(β−D−グルコピラノシル)−4−クロロ−3−[5-(6−フルオロ−2−ピリジル)−2−チエニルメチル]ベンゼン;及び
1−(β−D−グルコピラノシル)−4−メチル−3−[5-(3−ジフルオロメチルフェニル)−2−チエニルメチル]ベンゼン;
からなる群より選ばれる請求項1記載の化合物、またはその医薬的に許容しうる塩。 - 1−(β−D−グルコピラノシル)−4−メチル−3−[5-(4−フルオロフェニル)−2−チエニルメチル]ベンゼン、またはその医薬的に許容しうる塩。
- 1−(β−D−グルコピラノシル)−4−クロロ−3−[5-(6−フルオロ−3−ピリジル)−2−チエニルメチル]ベンゼン、またはその医薬的に許容しうる塩。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US49153403P | 2003-08-01 | 2003-08-01 | |
PCT/JP2004/011312 WO2005012326A1 (en) | 2003-08-01 | 2004-07-30 | Novel compounds having inhibitory activity against sodium-dependant transporter |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008100074A Division JP5065135B2 (ja) | 2003-08-01 | 2008-04-08 | 新規化合物 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2007518683A JP2007518683A (ja) | 2007-07-12 |
JP2007518683A5 true JP2007518683A5 (ja) | 2008-05-29 |
JP4130466B2 JP4130466B2 (ja) | 2008-08-06 |
Family
ID=34115515
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006519251A Active JP4130466B2 (ja) | 2003-08-01 | 2004-07-30 | 新規化合物 |
JP2008100074A Expired - Fee Related JP5065135B2 (ja) | 2003-08-01 | 2008-04-08 | 新規化合物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008100074A Expired - Fee Related JP5065135B2 (ja) | 2003-08-01 | 2008-04-08 | 新規化合物 |
Country Status (37)
Country | Link |
---|---|
US (3) | US7943788B2 (ja) |
EP (4) | EP3251679B1 (ja) |
JP (2) | JP4130466B2 (ja) |
KR (2) | KR100942622B1 (ja) |
CN (4) | CN103214471B (ja) |
AR (1) | AR045173A1 (ja) |
AU (1) | AU2004260761B2 (ja) |
BE (1) | BE2014C027I2 (ja) |
BR (1) | BRPI0413232B8 (ja) |
CA (1) | CA2534024C (ja) |
CR (2) | CR8188A (ja) |
CY (3) | CY1113813T1 (ja) |
DK (2) | DK1651658T4 (ja) |
EA (2) | EA010299B1 (ja) |
ES (4) | ES2649737T5 (ja) |
FR (1) | FR14C0034I2 (ja) |
HK (1) | HK1086277A1 (ja) |
HR (2) | HRP20130124T4 (ja) |
HU (2) | HUE037320T2 (ja) |
IL (2) | IL173050A (ja) |
LT (1) | LT2896397T (ja) |
LU (1) | LU92426I2 (ja) |
ME (1) | ME00411B (ja) |
MX (1) | MXPA06001274A (ja) |
MY (1) | MY143203A (ja) |
NL (1) | NL300670I2 (ja) |
NO (3) | NO333933B1 (ja) |
NZ (2) | NZ545304A (ja) |
PL (2) | PL1651658T5 (ja) |
PT (2) | PT1651658E (ja) |
RS (1) | RS53365B (ja) |
SG (1) | SG145694A1 (ja) |
SI (2) | SI1651658T2 (ja) |
TW (2) | TWI385177B (ja) |
UA (1) | UA83243C2 (ja) |
WO (1) | WO2005012326A1 (ja) |
ZA (5) | ZA200601685B (ja) |
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- 2011-01-13 US US13/005,757 patent/US8202984B2/en active Active
- 2011-07-01 US US13/174,814 patent/US8222219B2/en active Active
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2012
- 2012-05-18 NO NO20120585A patent/NO334706B1/no not_active IP Right Cessation
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2013
- 2013-02-12 HR HRP20130124TT patent/HRP20130124T4/hr unknown
- 2013-03-14 CY CY20131100223T patent/CY1113813T1/el unknown
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2014
- 2014-04-09 LU LU92426C patent/LU92426I2/fr unknown
- 2014-04-09 HU HUS1400021C patent/HUS1400021I1/hu unknown
- 2014-04-18 FR FR14C0034C patent/FR14C0034I2/fr active Active
- 2014-04-24 CY CY2014016C patent/CY2014016I2/el unknown
- 2014-04-25 NO NO2014009C patent/NO2014009I2/no not_active Application Discontinuation
- 2014-04-29 BE BE2014C027C patent/BE2014C027I2/nl unknown
- 2014-05-14 NL NL300670C patent/NL300670I2/nl unknown
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2017
- 2017-11-24 HR HRP20171838TT patent/HRP20171838T4/hr unknown
- 2017-12-06 CY CY20171101284T patent/CY1119814T1/el unknown
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