JP2014527997A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014527997A5 JP2014527997A5 JP2014532500A JP2014532500A JP2014527997A5 JP 2014527997 A5 JP2014527997 A5 JP 2014527997A5 JP 2014532500 A JP2014532500 A JP 2014532500A JP 2014532500 A JP2014532500 A JP 2014532500A JP 2014527997 A5 JP2014527997 A5 JP 2014527997A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- bis
- amino
- cyclopropylmethyl
- trifluoromethyl
- 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
- -1 1H-pyrazol-3-yl Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 20
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 16
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims description 12
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 102000015779 HDL Lipoproteins Human genes 0.000 claims description 8
- 108010010234 HDL Lipoproteins Proteins 0.000 claims description 8
- 102000007330 LDL Lipoproteins Human genes 0.000 claims description 8
- 108010007622 LDL Lipoproteins Proteins 0.000 claims description 8
- 235000012000 cholesterol Nutrition 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- UGJOSZKALSQWAA-UHFFFAOYSA-N 1-[2-[[6-[bis(cyclopropylmethyl)amino]-1,3-dimethylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]ethanone Chemical compound N1=CC(C(=O)C)=CN=C1N(CC=1C(=NC=2N(C)N=C(C)C=2C=1)N(CC1CC1)CC1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UGJOSZKALSQWAA-UHFFFAOYSA-N 0.000 claims description 2
- JJJVBMWJSLUPPC-UHFFFAOYSA-N 1-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]ethanone Chemical compound N1=CC(C(=O)C)=CN=C1N(CC=1C(=NC=2N(N=C(C)C=2C=1)C(C)(C)C)N(CC1CC1)CC1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JJJVBMWJSLUPPC-UHFFFAOYSA-N 0.000 claims description 2
- ZLFJEQSWPOUTQE-UHFFFAOYSA-N 1-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]pyrrolidin-2-one Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)N1C(CCC1)=O)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 ZLFJEQSWPOUTQE-UHFFFAOYSA-N 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 2
- QWIUVXSCUCYBRI-UHFFFAOYSA-N 3-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]-1,3-oxazolidin-2-one Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)N1C(OCC1)=O)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 QWIUVXSCUCYBRI-UHFFFAOYSA-N 0.000 claims description 2
- YSGNECRJOZOTJS-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-morpholin-4-ylpyrimidin-2-yl)amino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)N1CCOCC1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 YSGNECRJOZOTJS-UHFFFAOYSA-N 0.000 claims description 2
- OZJFYIOMAVRCBY-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-morpholin-4-ylpyrimidin-2-yl)amino]methyl]-n,n-bis(cyclopropylmethyl)-1,3-dimethylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)N1CCOCC1)CC=1C=C2C(C)=NN(C)C2=NC=1N(CC1CC1)CC1CC1 OZJFYIOMAVRCBY-UHFFFAOYSA-N 0.000 claims description 2
- DNQNMROHXBGNDH-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-[5-(1-methylpyrazol-3-yl)pyrimidin-2-yl]amino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)C1=NN(C)C=C1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 DNQNMROHXBGNDH-UHFFFAOYSA-N 0.000 claims description 2
- MQHAGAOYVLUYIK-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-[5-(1h-pyrazol-5-yl)pyrimidin-2-yl]amino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)C1=NNC=C1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 MQHAGAOYVLUYIK-UHFFFAOYSA-N 0.000 claims description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 2
- MJBWDEQAUQTVKK-IAGOWNOFSA-N aflatoxin M1 Chemical compound C=1([C@]2(O)C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O MJBWDEQAUQTVKK-IAGOWNOFSA-N 0.000 claims description 2
- VKKOLUVFLBZUIU-UHFFFAOYSA-N ethyl 2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-4-methylpyrimidine-5-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CN=C1N(CC=1C(=NC=2N(N=C(C)C=2C=1)C(C)(C)C)N(CC1CC1)CC1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VKKOLUVFLBZUIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- SUIVDHPMVHDPTR-UHFFFAOYSA-N n-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]-2-methylpropanamide Chemical compound N1=CC(NC(=O)C(C)C)=CN=C1N(CC=1C(=NC=2N(N=C(C)C=2C=1)C(C)(C)C)N(CC1CC1)CC1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SUIVDHPMVHDPTR-UHFFFAOYSA-N 0.000 claims description 2
- DIQWGVJRNIEHKI-UHFFFAOYSA-N n-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]cyclopropanecarboxamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(NC(=O)C2CC2)=CN=1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 DIQWGVJRNIEHKI-UHFFFAOYSA-N 0.000 claims description 2
- XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 claims description 2
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 2
- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 24
- 238000002560 therapeutic procedure Methods 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- WNSQSFXJJUQBBA-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-[5-(1,2-oxazol-3-yl)pyrimidin-2-yl]amino]methyl]-n,n-bis(cyclopropylmethyl)-1,3-dimethylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)C1=NOC=C1)CC=1C=C2C(C)=NN(C)C2=NC=1N(CC1CC1)CC1CC1 WNSQSFXJJUQBBA-UHFFFAOYSA-N 0.000 claims 1
- MZGWSZLPJKOQOK-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methylamino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CNCC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 MZGWSZLPJKOQOK-UHFFFAOYSA-N 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000000034 method Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- NNHRTHSVDJBLSL-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-bromopyrimidin-2-yl)amino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(Br)=CN=1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 NNHRTHSVDJBLSL-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)Cc1ccc(CN(*)Cc2cc(c(*)n[n]3O*)c3nc2N(*)*)cc1 Chemical compound CC(C)Cc1ccc(CN(*)Cc2cc(c(*)n[n]3O*)c3nc2N(*)*)cc1 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3337/CHE/2011 | 2011-09-27 | ||
| IN3337CH2011 | 2011-09-27 | ||
| US201161558262P | 2011-11-10 | 2011-11-10 | |
| US61/558,262 | 2011-11-10 | ||
| PCT/IB2012/002435 WO2013046045A1 (en) | 2011-09-27 | 2012-09-27 | 5 - benzylaminomethyl - 6 - aminopyrazolo [3, 4 -b] pyridine derivatives as cholesteryl ester -transfer protein (cetp) inhibitors useful for the treatment of atherosclerosis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014527997A JP2014527997A (ja) | 2014-10-23 |
| JP2014527997A5 true JP2014527997A5 (https=) | 2015-10-29 |
| JP6140168B2 JP6140168B2 (ja) | 2017-05-31 |
Family
ID=47994351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014532500A Expired - Fee Related JP6140168B2 (ja) | 2011-09-27 | 2012-09-27 | アテローム性動脈硬化症の処置のために有用なコレステリルエステル転送タンパク質（ｃｅｔｐ）インヒビターとしての５−ベンジルアミノメチル−６−アミノピラゾロ［３，４−ｂ］ピリジン誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9000007B2 (https=) |
| EP (1) | EP2760864B1 (https=) |
| JP (1) | JP6140168B2 (https=) |
| KR (1) | KR101803866B1 (https=) |
| CN (1) | CN103958511A (https=) |
| AU (1) | AU2012313971B2 (https=) |
| CA (1) | CA2850022C (https=) |
| HK (1) | HK1197238A1 (https=) |
| IN (1) | IN2014CN02290A (https=) |
| MX (1) | MX352074B (https=) |
| WO (1) | WO2013046045A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3081864B2 (ja) | 1996-01-08 | 2000-08-28 | 三井化学株式会社 | 金属製接続部材付き合成樹脂製管継手及びその製造方法 |
| JPWO2014017569A1 (ja) * | 2012-07-26 | 2016-07-11 | 興和株式会社 | 血中ｌｄｌを低下させるための医薬 |
| JP2015054838A (ja) * | 2013-09-12 | 2015-03-23 | 興和株式会社 | 血中ｌｄｌコレステロールを低下させる医薬 |
| EP3081566B1 (en) * | 2013-12-13 | 2018-03-07 | Daiichi Sankyo Company, Limited | 5-hydroxy-4-(trifluoromethyl)pyrazolopyridine derivative |
| CN109956940A (zh) * | 2019-05-14 | 2019-07-02 | 上海贤鼎生物科技有限公司 | 一种帕博昔布中间体氰基化反应制备杂芳基氰化物的方法 |
Family Cites Families (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965643A (en) | 1960-12-20 | Derivatives of pyrazolo | ||
| US2858309A (en) | 1956-05-07 | 1958-10-28 | Ciba Pharm Prod Inc | New aminobenzene sulfonamide |
| US3546295A (en) | 1968-08-01 | 1970-12-08 | Exxon Research Engineering Co | N-cycloalkyl anilines |
| DE3143016A1 (de) | 1980-10-29 | 1982-05-27 | Nippon Kayaku K.K., Tokyo | 5,6,7,8-tetrahydro-1,6-naphthyridinderivate und verfahren zu ihrer herstellung |
| JPH01104052A (ja) | 1987-06-12 | 1989-04-21 | Yoshitomi Pharmaceut Ind Ltd | ピリジン誘導体 |
| ATE92752T1 (de) | 1987-07-08 | 1993-08-15 | American Home Prod | Spruehgetrocknete ibuprofen-zusammensetzungen. |
| US5474989A (en) | 1988-11-11 | 1995-12-12 | Kurita Water Industries, Ltd. | Drug composition |
| US5260331A (en) | 1989-01-02 | 1993-11-09 | John Wyeth & Brother Limited | Composition for treating depression with (S- or O-heteroaryl)alkyl amines |
| US5422355A (en) | 1989-06-02 | 1995-06-06 | John Wyeth & Brother, Limited | Composition for treating depression with (N-heteroaryl)alkylamines |
| AU641394B2 (en) | 1989-06-02 | 1993-09-23 | John Wyeth & Brother Limited | Amines |
| KR0182801B1 (ko) | 1991-04-16 | 1999-05-01 | 아만 히데아키 | 고체 분산체의 제조방법 |
| US5348953A (en) | 1991-06-25 | 1994-09-20 | Merck & Co., Inc. | Substituted azetidinones as anti-inflammatory and antidegenerative agents |
| WO1993000332A1 (en) | 1991-06-25 | 1993-01-07 | Merck & Co., Inc. | Substituted azetidinones as anti-inflammatory and antidegenerative agents |
| TW225469B (https=) | 1991-11-12 | 1994-06-21 | Nissan Kagakl Kogyo | |
| FR2686339B1 (fr) | 1992-01-22 | 1994-03-11 | Adir Cie | Nouveaux amides et sulfonamides naphtaleniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| EP0585500A1 (en) | 1992-09-04 | 1994-03-09 | Merrell Dow Pharmaceuticals Inc. | Diaryl piperazineacetamides as antimuscarinic agents |
| EP0585913B1 (en) | 1992-09-04 | 1997-12-29 | Takeda Chemical Industries, Ltd. | Condensed heterocyclic compounds, their production and use |
| MY131441A (en) | 1992-12-29 | 2007-08-30 | American Cyanamid Co | Amidrazones and their use as insecticidal and acaricidal agents |
| WO1995005363A1 (en) | 1993-08-12 | 1995-02-23 | Astra Aktiebolag | Amidine derivatives with nitric oxide synthetase activities |
| US5491152A (en) | 1994-03-23 | 1996-02-13 | The Du Pont Merck Pharmaceutical Company | Derivatives of cyclic ethers and sulfides for the treatment of atherosclerosis |
| JPH07285962A (ja) | 1994-04-20 | 1995-10-31 | Nissan Chem Ind Ltd | ピリジンカルボン酸アミド誘導体 |
| IT1270615B (it) | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
| JPH0892224A (ja) | 1994-09-16 | 1996-04-09 | Kumiai Chem Ind Co Ltd | ３，５−置換フェニルトリアゾール誘導体および殺虫、殺ダニ剤 |
| JPH0892225A (ja) | 1994-09-29 | 1996-04-09 | Nissan Chem Ind Ltd | トリアゾールグリコール酸アミド誘導体 |
| AU689972B2 (en) | 1994-11-29 | 1998-04-09 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/or salt thereof |
| GB9511220D0 (en) | 1995-06-02 | 1995-07-26 | Glaxo Group Ltd | Solid dispersions |
| US6730679B1 (en) | 1996-03-22 | 2004-05-04 | Smithkline Beecham Corporation | Pharmaceutical formulations |
| DE19615262A1 (de) | 1996-04-18 | 1997-10-23 | Bayer Ag | Heteroverknüpfte Phenylglycinolamide |
| ATE255883T1 (de) | 1996-05-20 | 2003-12-15 | Janssen Pharmaceutica Nv | Fungizide mittel mit verbesserter bioverfügbarkeit |
| AR008789A1 (es) | 1996-07-31 | 2000-02-23 | Bayer Corp | Piridinas y bifenilos substituidos |
| DE19636150A1 (de) | 1996-09-06 | 1998-03-12 | Asta Medica Ag | N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung |
| TW523506B (en) | 1996-12-18 | 2003-03-11 | Ono Pharmaceutical Co | Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients |
| WO1998057927A1 (en) | 1997-06-16 | 1998-12-23 | American Home Products Corporation | Elevation of hdl cholesterol by 4-[(aminothioxomethyl)hydrazono]-4-arylbutyl carbamates |
| US5977170A (en) | 1997-06-16 | 1999-11-02 | American Home Products Corporation | Elevation of HDL cholesterol by 4-[(aminothioxomethyl)hydrazono]-4-arylbutyl carbamates |
| WO1998057925A1 (en) | 1997-06-16 | 1998-12-23 | American Home Products Corporation | Elevation of hdl cholesterol by 2-[(aminothioxomethyl)-hydrazono]-2-arylethyl carbamates |
| WO1998057928A1 (en) | 1997-06-16 | 1998-12-23 | American Home Products Corporation | Elevation of hdl cholesterol by 2-(4-chloro -1-aryl-butylidene) -hydrazinecarbothioamides |
| US6008362A (en) | 1997-06-16 | 1999-12-28 | Commons; Thomas Joseph | Elevation of HDL cholesterol by 2-(-4-chlorol-1-aryl-butylidene)-hydrazinecarbothioamides |
| EP1741424B1 (en) | 1997-08-11 | 2018-10-03 | Pfizer Products Inc. | Solid pharmaceutical dispersions with enhanced bioavailabilty |
| UA67754C2 (uk) | 1997-10-10 | 2004-07-15 | Пфайзер, Інк. | Агоністи простагландину, фармацевтична композиція на їх основі (варіанти), спосіб нарощення та збереження кісткової маси у хребетних та спосіб лікування (варіанти) |
| JPH11209366A (ja) | 1998-01-23 | 1999-08-03 | Nissan Chem Ind Ltd | クロマン誘導体及び心不全治療薬 |
| DE19814838C2 (de) | 1998-04-02 | 2001-01-18 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
| US6121271A (en) | 1998-05-12 | 2000-09-19 | American Home Products Corporation | Naphtho[2,3-B]heteroar-4-yl derivatives |
| GT199900147A (es) | 1998-09-17 | 1999-09-06 | 1, 2, 3, 4- tetrahidroquinolinas 2-sustituidas 4-amino sustituidas. | |
| US6350786B1 (en) | 1998-09-22 | 2002-02-26 | Hoffmann-La Roche Inc. | Stable complexes of poorly soluble compounds in ionic polymers |
| DE19845202A1 (de) | 1998-10-01 | 2000-04-06 | Wella Ag | Haarwuchsmittel |
| CN1236813C (zh) | 1998-12-11 | 2006-01-18 | 药品处理公司 | 水难溶性药物的自乳化组合物 |
| ES2306646T3 (es) | 1999-02-09 | 2008-11-16 | Pfizer Products Inc. | Composiciones de farmacos basicos con biodisponibilidad incrementada. |
| HRP20010603A2 (en) | 1999-02-24 | 2002-08-31 | Hoffmann La Roche | Phenyl-and pyridinyl derivatives |
| KR100644739B1 (ko) | 1999-06-23 | 2006-11-13 | 신젠타 파티서페이션즈 아게 | 니트로구아니딘 및 니트로엔아민 유도체의 제조방법 |
| DE19930075A1 (de) | 1999-06-30 | 2001-01-04 | Bayer Ag | Neue Amino- und Amidosulfonamide als antivirale Mittel |
| US6586433B2 (en) | 1999-09-23 | 2003-07-01 | Pharmacia Corporation | Substituted N-heteroaryl-N-phenyl aminoalcohol compounds useful for inhibiting cholesteryl ester transfer protein activity |
| TWI269654B (en) | 1999-09-28 | 2007-01-01 | Baxter Healthcare Sa | N-substituted indole-3-glyoxylamide compounds having anti-tumor action |
| EP1108426A3 (en) | 1999-12-02 | 2002-10-02 | Pfizer Products Inc. | Use of prostaglandin agonists to treat erectile dysfunction or impotence |
| MXPA02006079A (es) | 1999-12-20 | 2004-08-23 | Nicholas J Kerkhof | Proceso para producir particulas de nanometro mediante secado por aspersion de lecho fluido. |
| DE19962300A1 (de) | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| US6306911B1 (en) | 2000-02-07 | 2001-10-23 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted amino acids as neutral sphingomyelinase inhibitors |
| AU2001243158A1 (en) | 2000-02-18 | 2001-08-27 | Merck And Co., Inc. | Inhibitors of prenyl-protein transferase |
| WO2001060458A2 (en) | 2000-02-18 | 2001-08-23 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| DE10023484A1 (de) | 2000-05-09 | 2001-11-22 | Schering Ag | Anthranylamide und deren Verwendung als Arzneimittel |
| AU7105501A (en) | 2000-07-17 | 2002-01-30 | Yamanouchi Pharma Co Ltd | Pharmaceutical composition improved in peroral absorbability |
| US7115279B2 (en) | 2000-08-03 | 2006-10-03 | Curatolo William J | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
| US6576644B2 (en) | 2000-09-06 | 2003-06-10 | Bristol-Myers Squibb Co. | Quinoline inhibitors of cGMP phosphodiesterase |
| AU2001294557A1 (en) | 2000-09-11 | 2002-03-26 | Merck And Co., Inc. | Thrombin inhibitors |
| US6642252B2 (en) | 2000-11-07 | 2003-11-04 | Bristol-Myers Squibb Company | Acid derivatives useful as serine protease inhibitors |
| US6869617B2 (en) | 2000-12-22 | 2005-03-22 | Baxter International Inc. | Microprecipitation method for preparing submicron suspensions |
| CN1853630A (zh) | 2001-02-21 | 2006-11-01 | Nps制药公司 | 杂多环化合物及其在亲代谢的谷氨酸受体拮抗剂中的应用 |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| US7034013B2 (en) | 2001-03-20 | 2006-04-25 | Cydex, Inc. | Formulations containing propofol and a sulfoalkyl ether cyclodextrin |
| US7459470B2 (en) | 2001-05-08 | 2008-12-02 | Schering Ag | N-oxide anthranylamide derivatives and their use as medicaments |
| WO2003000295A2 (en) | 2001-06-21 | 2003-01-03 | Pfizer Products Inc. | Self-emulsifying formulations of cholesteryl ester transfer protein inhibitors |
| EP1269994A3 (en) | 2001-06-22 | 2003-02-12 | Pfizer Products Inc. | Pharmaceutical compositions comprising drug and concentration-enhancing polymers |
| AU2002309172A1 (en) | 2001-06-22 | 2003-01-08 | Pfizer Products Inc. | Pharmaceutical compositions containing polymer and drug assemblies |
| ES2284871T3 (es) | 2001-06-22 | 2007-11-16 | Pfizer Products Inc. | Composiciones farmaceuticas que contienen una dispersion solida de farmaco poco soluble y un polimero potenciador de la solubilidad. |
| EE200400034A (et) | 2001-06-22 | 2004-06-15 | Pfizer Products Inc. | Amorfse ravimaine adsorbaatide farmatseutilised kompositsioonid |
| WO2003030909A1 (en) | 2001-09-25 | 2003-04-17 | Bayer Pharmaceuticals Corporation | 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer |
| US6713499B2 (en) | 2001-12-12 | 2004-03-30 | Hoffman-La Roche Inc. | 7-Amino-benzothiazole derivatives |
| AR038375A1 (es) | 2002-02-01 | 2005-01-12 | Pfizer Prod Inc | Composiciones farmaceuticas de inhibidores de la proteina de transferencia de esteres de colesterilo |
| DE60322665D1 (de) | 2002-02-01 | 2008-09-18 | Pfizer Prod Inc | Pharmazeutische darreichungsform mit gesteuerter freigabe eines cholesterylester-transferproteininhibitors |
| GB0208280D0 (en) | 2002-04-10 | 2002-05-22 | Glaxo Group Ltd | Novel compounds |
| US20040053842A1 (en) | 2002-07-02 | 2004-03-18 | Pfizer Inc. | Methods of treatment with CETP inhibitors and antihypertensive agents |
| US7071210B2 (en) | 2002-07-02 | 2006-07-04 | Pfizer Inc. | CETP inhibitors in combination with antihypertensive agents and uses thereof |
| BR0306208A (pt) | 2002-08-30 | 2004-10-13 | Japan Tobacco Inc | Compostos de dibenzilamina e seu uso farmacêutico |
| EP1961419B1 (en) | 2002-12-20 | 2010-03-24 | Pfizer Products Inc. | Dosage forms comprising a CETP inhibitor and an HMG-CoA reductase inhibitor |
| GB0303683D0 (en) | 2003-02-18 | 2003-03-19 | Prolysis Ltd | Antimicrobial agents |
| EP1603879A2 (en) | 2003-02-28 | 2005-12-14 | Bayer Pharmaceuticals Corporation | Substituted pyridine derivatives useful in the treatment of cancer and other disorders |
| NZ541828A (en) | 2003-03-04 | 2008-06-30 | Pfizer Prod Inc | Use of EP2 selective receptor agonists in medical treatment |
| US7619096B2 (en) | 2003-06-11 | 2009-11-17 | Eli Lilly And Company | 3-Aminopyrrolidines as inhibitors of monoamine uptake |
| EP1653926A1 (en) | 2003-08-04 | 2006-05-10 | Pfizer Products Inc. | Dosage forms providing controlled release of cholesteryl ester transfer protein inhibitors and immediate release of hmg-coa reductase inhibitors |
| WO2005021525A1 (en) | 2003-08-27 | 2005-03-10 | Janssen Pharmaceutica, N.V. | Aryl piperidine amides |
| WO2005030185A2 (en) | 2003-09-26 | 2005-04-07 | Japan Tobacco Inc. | Method of inhibiting remnant lipoprotein production |
| WO2005097805A1 (en) | 2004-03-26 | 2005-10-20 | Eli Lilly And Company | Compounds and methods for treating dyslipidemia |
| UA90269C2 (ru) | 2004-04-02 | 2010-04-26 | Мицубиси Танабе Фарма Корпорейшн | Тетрагидрохинолиновые производные и способ их получения |
| TWI345568B (en) | 2004-04-02 | 2011-07-21 | Mitsubishi Tanabe Pharma Corp | Tetrahydronaphthyridine derivatives and a process for preparing the same |
| CN1942428A (zh) | 2004-04-13 | 2007-04-04 | 默克公司 | Cetp抑制剂 |
| PE20061124A1 (es) | 2004-11-23 | 2006-10-13 | Pfizer Prod Inc | Compuestos y derivados de dibencil amina |
| WO2006073973A2 (en) * | 2004-12-31 | 2006-07-13 | Reddy Us Therapeutics, Inc. | Novel benzylamine derivatives as cetp inhibitors |
| US8604055B2 (en) * | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| US8828438B2 (en) | 2005-05-31 | 2014-09-09 | Bend Research, Inc. | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors and HMG-CoA reductase |
| JP4981814B2 (ja) * | 2005-12-28 | 2012-07-25 | ドクター・レディーズ・ラボラトリーズ・リミテッド | 選択的なベンジルアミン誘導体およびコレステロールエステル転写タンパク質抑制剤としてのその有用性 |
| PE20071025A1 (es) * | 2006-01-31 | 2007-10-17 | Mitsubishi Tanabe Pharma Corp | Compuesto amina trisustituido |
| JP5773560B2 (ja) | 2006-02-09 | 2015-09-02 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | Ｃｅｔｐ阻害剤のポリマー製剤 |
| WO2007128568A1 (en) | 2006-05-10 | 2007-11-15 | Novartis Ag | Bicyclic derivatives as cetp inhibitors |
| US7790737B2 (en) * | 2007-03-13 | 2010-09-07 | Kowa Company, Ltd. | Substituted pyrimidine compounds and their utility as CETP inhibitors |
| JP4834699B2 (ja) * | 2007-07-30 | 2011-12-14 | 田辺三菱製薬株式会社 | 医薬組成物 |
| CN101418397A (zh) * | 2008-12-02 | 2009-04-29 | 西北有色金属研究院 | 一种TiB2强化的MgAlB14超硬材料的制备方法 |
-
2012
- 2012-09-27 MX MX2014003660A patent/MX352074B/es active IP Right Grant
- 2012-09-27 CA CA2850022A patent/CA2850022C/en not_active Expired - Fee Related
- 2012-09-27 AU AU2012313971A patent/AU2012313971B2/en not_active Ceased
- 2012-09-27 JP JP2014532500A patent/JP6140168B2/ja not_active Expired - Fee Related
- 2012-09-27 HK HK14110754.9A patent/HK1197238A1/xx unknown
- 2012-09-27 US US14/347,519 patent/US9000007B2/en not_active Expired - Fee Related
- 2012-09-27 CN CN201280057987.XA patent/CN103958511A/zh active Pending
- 2012-09-27 EP EP12816102.3A patent/EP2760864B1/en not_active Not-in-force
- 2012-09-27 KR KR1020147009133A patent/KR101803866B1/ko not_active Expired - Fee Related
- 2012-09-27 IN IN2290CHN2014 patent/IN2014CN02290A/en unknown
- 2012-09-27 WO PCT/IB2012/002435 patent/WO2013046045A1/en not_active Ceased