JP2004504385A5 - - Google Patents
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- Publication number
- JP2004504385A5 JP2004504385A5 JP2002514106A JP2002514106A JP2004504385A5 JP 2004504385 A5 JP2004504385 A5 JP 2004504385A5 JP 2002514106 A JP2002514106 A JP 2002514106A JP 2002514106 A JP2002514106 A JP 2002514106A JP 2004504385 A5 JP2004504385 A5 JP 2004504385A5
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- pyrimidin
- phenyl
- compound
- ethoxy
- 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
- 150000001875 compounds Chemical class 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- 125000003282 alkyl amino group Chemical group 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- -1 hydroxy, hydroxy Chemical group 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 102000002045 Endothelin Human genes 0.000 description 3
- 108050009340 Endothelin Proteins 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 208000002249 Diabetes Complications Diseases 0.000 description 2
- 206010012655 Diabetic complications Diseases 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- MRXLOJWYKVIJFZ-UHFFFAOYSA-N 6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)-2-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CC=CC=C1OC1=C(N)N=C(C=2C=CN=CC=2)N=C1OCCOC1=NC=C(Br)C=N1 MRXLOJWYKVIJFZ-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 125000004468 heterocyclylthio group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- VOKXISGERQFNIR-UHFFFAOYSA-N n-[5-(2-methoxyphenoxy)-2-morpholin-4-yl-6-[2-[5-(trifluoromethyl)pyrimidin-2-yl]oxyethoxy]pyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)N2CCOCC2)OCCOC=2N=CC(=CN=2)C(F)(F)F)=C1NS(=O)(=O)C=CC1=CC=CC=C1 VOKXISGERQFNIR-UHFFFAOYSA-N 0.000 description 1
- UDBIGWXUPISPSU-UHFFFAOYSA-N n-[6-[2-(4-bromophenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound C1=CC(C)=CC=C1C(C(=NC=N1)OCCOC=2C=CC(Br)=CC=2)=C1NS(=O)(=O)C=CC1=CC=CC=C1 UDBIGWXUPISPSU-UHFFFAOYSA-N 0.000 description 1
- ATKBAZHAPWPPDN-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-chloro-5-methoxyphenoxy)pyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound COC1=CC=C(Cl)C(OC=2C(=NC=NC=2NS(=O)(=O)C=CC=2C=CC=CC=2)OCCOC=2N=CC(Br)=CN=2)=C1 ATKBAZHAPWPPDN-UHFFFAOYSA-N 0.000 description 1
- PSXBTEJFWAROQI-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)-2-morpholin-4-ylpyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)N2CCOCC2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)C=CC1=CC=CC=C1 PSXBTEJFWAROQI-UHFFFAOYSA-N 0.000 description 1
- YFMYLPBYYDBNLK-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)-2-pyrazin-2-ylpyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=NC=2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)C=CC1=CC=CC=C1 YFMYLPBYYDBNLK-UHFFFAOYSA-N 0.000 description 1
- DDILETXOYFQDGJ-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)pyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)C=CC1=CC=CC=C1 DDILETXOYFQDGJ-UHFFFAOYSA-N 0.000 description 1
- HISPNRSQDRCNSY-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(3-methoxyphenoxy)pyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound COC1=CC=CC(OC=2C(=NC=NC=2NS(=O)(=O)C=CC=2C=CC=CC=2)OCCOC=2N=CC(Br)=CN=2)=C1 HISPNRSQDRCNSY-UHFFFAOYSA-N 0.000 description 1
- IWCSITMDGRHZDA-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)pyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound C1=CC(Cl)=CC=C1C(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)C=CC1=CC=CC=C1 IWCSITMDGRHZDA-UHFFFAOYSA-N 0.000 description 1
- QPKOFLLZUQZFNW-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-methylphenyl)-2-pyridin-4-ylpyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound C1=CC(C)=CC=C1C(C(=NC(=N1)C=2C=CN=CC=2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)C=CC1=CC=CC=C1 QPKOFLLZUQZFNW-UHFFFAOYSA-N 0.000 description 1
- RPBOIJRVAJKCSF-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-methylphenyl)pyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound C1=CC(C)=CC=C1C(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)C=CC1=CC=CC=C1 RPBOIJRVAJKCSF-UHFFFAOYSA-N 0.000 description 1
- AWCUTSLFDTUMOV-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-methylphenyl)pyrimidin-4-yl]-2-thiophen-2-ylethenesulfonamide Chemical compound C1=CC(C)=CC=C1C(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)C=CC1=CC=CS1 AWCUTSLFDTUMOV-UHFFFAOYSA-N 0.000 description 1
- PEEIDSYARNRPRX-UHFFFAOYSA-N n-[6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-methylphenyl)pyrimidin-4-yl]-2-thiophen-3-ylethenesulfonamide Chemical compound C1=CC(C)=CC=C1C(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)C=CC1=CSC=C1 PEEIDSYARNRPRX-UHFFFAOYSA-N 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP00/07006 | 2000-07-21 | ||
| EP0007006 | 2000-07-21 | ||
| PCT/EP2001/007922 WO2002008200A2 (en) | 2000-07-21 | 2001-07-10 | Arylethene-sulfonamides, their preparation and their use as endothelin antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004504385A JP2004504385A (ja) | 2004-02-12 |
| JP2004504385A5 true JP2004504385A5 (enExample) | 2008-08-14 |
| JP4832706B2 JP4832706B2 (ja) | 2011-12-07 |
Family
ID=8164031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002514106A Expired - Fee Related JP4832706B2 (ja) | 2000-07-21 | 2001-07-10 | 新規なアリールエテン−スルフォンアミド類 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6951856B2 (enExample) |
| EP (1) | EP1309564B1 (enExample) |
| JP (1) | JP4832706B2 (enExample) |
| KR (1) | KR100826332B1 (enExample) |
| CN (1) | CN100562518C (enExample) |
| AR (1) | AR030247A1 (enExample) |
| AT (1) | ATE329908T1 (enExample) |
| AU (2) | AU8197001A (enExample) |
| BR (1) | BR0112614A (enExample) |
| CA (1) | CA2416785C (enExample) |
| DE (1) | DE60120711T2 (enExample) |
| ES (1) | ES2266233T3 (enExample) |
| HU (1) | HUP0300965A3 (enExample) |
| IL (2) | IL153471A0 (enExample) |
| MX (1) | MXPA03000430A (enExample) |
| MY (1) | MY140724A (enExample) |
| NO (1) | NO324771B1 (enExample) |
| NZ (1) | NZ523304A (enExample) |
| TW (1) | TWI289553B (enExample) |
| WO (1) | WO2002008200A2 (enExample) |
| ZA (1) | ZA200300137B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2422441C2 (ru) | 2004-03-05 | 2011-06-27 | Ф.Хоффманн-Ля Рош Аг | Диаминопиримидины в качестве антагонистов рецепторов р2х3 |
| ES2612890T3 (es) | 2005-09-01 | 2017-05-19 | F. Hoffmann-La Roche Ag | Diaminopirimidinas como moduladores de P2X3 y P2X2/3 |
| EP1924565B1 (en) | 2005-09-01 | 2016-09-14 | F.Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p3x2/3 modulators |
| EP1924566B1 (en) | 2005-09-01 | 2016-01-13 | F.Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| TWI331523B (en) * | 2005-12-08 | 2010-10-11 | Nat Health Research Institutes | Vinylsulfonate compounds |
| CA2695864A1 (en) * | 2007-08-07 | 2009-02-12 | Schering Corporation | Gamma secretase modulators |
| WO2009104152A1 (en) * | 2008-02-20 | 2009-08-27 | Actelion Pharmaceuticals Ltd | Combination treatment for ovarian cancer |
| IT1393136B1 (it) * | 2009-03-11 | 2012-04-11 | Sifa Vitor S R L | Procedimento per la preparazione del bosentan |
| US20100256371A1 (en) * | 2009-04-02 | 2010-10-07 | Glenmark | Processes for the preparation of bosentan and its intermediates thereof |
| SG11202002267UA (en) | 2017-09-12 | 2020-04-29 | Agency Science Tech & Res | Compounds useful as inhibitors of isoprenylcysteine carboxyl methyltransferase |
| CN110885328B (zh) * | 2018-09-10 | 2022-08-12 | 成都康弘药业集团股份有限公司 | 作为钠通道阻滞剂的磺酰胺类化合物及其用途 |
| WO2023078463A1 (zh) * | 2021-11-08 | 2023-05-11 | 正大天晴药业集团股份有限公司 | 氮杂联苯类化合物及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2086544C1 (ru) | 1991-06-13 | 1997-08-10 | Хоффманн-Ля Рош АГ | Бензолсульфонамидные производные пиримидина или их соли, фармацевтическая композиция для лечения заболеваний, связанных с активностью эндотелина |
| TW287160B (enExample) * | 1992-12-10 | 1996-10-01 | Hoffmann La Roche | |
| TW394761B (en) | 1993-06-28 | 2000-06-21 | Hoffmann La Roche | Novel Sulfonylamino Pyrimidines |
| JP2790065B2 (ja) * | 1993-12-17 | 1998-08-27 | 田辺製薬株式会社 | ベンゼンスルホンアミド誘導体及びその製法 |
| IL111959A (en) * | 1993-12-17 | 2000-07-16 | Tanabe Seiyaku Co | N-(polysubstituted pyrimidin-4-yl) benzenesulfonamide derivatives their preparation and pharmaceutical compositions containing them |
| US5739333A (en) | 1995-05-16 | 1998-04-14 | Tanabe Seiyaku Co., Ltd. | Sulfonamide derivative and process for preparing the same |
| RU2172735C2 (ru) | 1995-12-20 | 2001-08-27 | Яманоути Фармасьютикал Ко., Лтд. | Арилэтенсульфонамидные производные и фармацевтическая композиция |
| TWI284642B (en) | 1999-01-18 | 2007-08-01 | Hoffmann La Roche | Novel heterocyclic sulfonamides |
| US6417360B1 (en) | 1999-03-03 | 2002-07-09 | Hoffmann-La Roche Inc. | Heterocyclic sulfonamides |
-
2001
- 2001-07-09 MY MYPI20013244A patent/MY140724A/en unknown
- 2001-07-10 AU AU8197001A patent/AU8197001A/xx active Pending
- 2001-07-10 HU HU0300965A patent/HUP0300965A3/hu unknown
- 2001-07-10 CA CA002416785A patent/CA2416785C/en not_active Expired - Fee Related
- 2001-07-10 KR KR1020037000256A patent/KR100826332B1/ko not_active Expired - Fee Related
- 2001-07-10 US US10/332,247 patent/US6951856B2/en not_active Expired - Fee Related
- 2001-07-10 EP EP01960485A patent/EP1309564B1/en not_active Expired - Lifetime
- 2001-07-10 MX MXPA03000430A patent/MXPA03000430A/es active IP Right Grant
- 2001-07-10 CN CNB018126693A patent/CN100562518C/zh not_active Expired - Fee Related
- 2001-07-10 NZ NZ523304A patent/NZ523304A/en unknown
- 2001-07-10 DE DE60120711T patent/DE60120711T2/de not_active Expired - Lifetime
- 2001-07-10 IL IL15347101A patent/IL153471A0/xx active IP Right Grant
- 2001-07-10 BR BR0112614-8A patent/BR0112614A/pt not_active Application Discontinuation
- 2001-07-10 JP JP2002514106A patent/JP4832706B2/ja not_active Expired - Fee Related
- 2001-07-10 ES ES01960485T patent/ES2266233T3/es not_active Expired - Lifetime
- 2001-07-10 AU AU2001281970A patent/AU2001281970B2/en not_active Ceased
- 2001-07-10 WO PCT/EP2001/007922 patent/WO2002008200A2/en not_active Ceased
- 2001-07-10 AT AT01960485T patent/ATE329908T1/de active
- 2001-07-16 AR ARP010103391A patent/AR030247A1/es active IP Right Grant
- 2001-07-23 TW TW090117915A patent/TWI289553B/zh not_active IP Right Cessation
-
2002
- 2002-12-16 IL IL153471A patent/IL153471A/en not_active IP Right Cessation
-
2003
- 2003-01-06 ZA ZA200300137A patent/ZA200300137B/en unknown
- 2003-01-20 NO NO20030274A patent/NO324771B1/no not_active IP Right Cessation
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