JP2006502120A5 - - Google Patents
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- JP2006502120A5 JP2006502120A5 JP2004523221A JP2004523221A JP2006502120A5 JP 2006502120 A5 JP2006502120 A5 JP 2006502120A5 JP 2004523221 A JP2004523221 A JP 2004523221A JP 2004523221 A JP2004523221 A JP 2004523221A JP 2006502120 A5 JP2006502120 A5 JP 2006502120A5
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- JP
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- Prior art keywords
- compound
- formula
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- pharmaceutical composition
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 18
- 238000000034 method Methods 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 4
- 239000002841 Lewis acid Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 150000007517 lewis acids Chemical class 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- 102000009465 Growth Factor Receptors Human genes 0.000 claims 3
- 108010009202 Growth Factor Receptors Proteins 0.000 claims 3
- 229940125898 compound 5 Drugs 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 150000002978 peroxides Chemical class 0.000 claims 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- 229940125904 compound 1 Drugs 0.000 claims 2
- 229940125782 compound 2 Drugs 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- 238000006722 reduction reaction Methods 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- -1 alkoxy anion Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000001772 anti-angiogenic effect Effects 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229940125773 compound 10 Drugs 0.000 claims 1
- 229940125797 compound 12 Drugs 0.000 claims 1
- 229940126543 compound 14 Drugs 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 231100000599 cytotoxic agent Toxicity 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 239000000852 hydrogen donor Substances 0.000 claims 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical group [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 108060006633 protein kinase Proteins 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- 229960001922 sodium perborate Drugs 0.000 claims 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 0 Cc(c(*)c1)c2[n]1ncnc2O* Chemical compound Cc(c(*)c1)c2[n]1ncnc2O* 0.000 description 1
- AHFYXDBDJPEHBC-UHFFFAOYSA-N Cc(c(C)c12)c[n]1ncnc2Oc(ccc1c2cc(C)[nH]1)c2F Chemical compound Cc(c(C)c12)c[n]1ncnc2Oc(ccc1c2cc(C)[nH]1)c2F AHFYXDBDJPEHBC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39725602P | 2002-07-19 | 2002-07-19 | |
| US44721303P | 2003-02-13 | 2003-02-13 | |
| US10/622,280 US6933386B2 (en) | 2002-07-19 | 2003-07-18 | Process for preparing certain pyrrolotriazine compounds |
| PCT/US2003/022755 WO2004009542A2 (en) | 2002-07-19 | 2003-07-21 | Process for preparing certain pyrrolotriazine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006502120A JP2006502120A (ja) | 2006-01-19 |
| JP2006502120A5 true JP2006502120A5 (https=) | 2006-03-30 |
Family
ID=30773518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004523221A Withdrawn JP2006502120A (ja) | 2002-07-19 | 2003-07-21 | ピロロトリアジン化合物の製造法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6933386B2 (https=) |
| EP (1) | EP1554281A4 (https=) |
| JP (1) | JP2006502120A (https=) |
| CN (1) | CN1665817A (https=) |
| AU (1) | AU2003256645A1 (https=) |
| BR (1) | BR0312648A (https=) |
| CA (1) | CA2492861A1 (https=) |
| IL (1) | IL165985A0 (https=) |
| MX (1) | MXPA05000344A (https=) |
| PL (1) | PL375316A1 (https=) |
| TW (1) | TWI272271B (https=) |
| WO (1) | WO2004009542A2 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6867300B2 (en) * | 2000-11-17 | 2005-03-15 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
| KR101025675B1 (ko) * | 2002-04-23 | 2011-03-30 | 브리스톨-마이어스 스큅 컴퍼니 | 키나제 억제제로서 유용한 피롤로-트리아진 아닐린 화합물 |
| JP2005529890A (ja) | 2002-04-23 | 2005-10-06 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼ阻害剤として有用なアリールケトンピロロトリアジン化合物 |
| TWI329112B (en) * | 2002-07-19 | 2010-08-21 | Bristol Myers Squibb Co | Novel inhibitors of kinases |
| BRPI0407282A (pt) | 2003-02-05 | 2006-01-31 | Bristol Myers Squibb Co | Processo para preparação de inibidores de pirrolotriazina cinase |
| US7102001B2 (en) * | 2003-12-12 | 2006-09-05 | Bristol-Myers Squibb Company | Process for preparing pyrrolotriazine |
| US20060014741A1 (en) * | 2003-12-12 | 2006-01-19 | Dimarco John D | Synthetic process, and crystalline forms of a pyrrolotriazine compound |
| US7064203B2 (en) | 2003-12-29 | 2006-06-20 | Bristol Myers Squibb Company | Di-substituted pyrrolotriazine compounds |
| MY145634A (en) * | 2003-12-29 | 2012-03-15 | Bristol Myers Squibb Co | Pyrrolotriazine compounds as kinase inhibitors |
| US7102002B2 (en) * | 2004-06-16 | 2006-09-05 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7173031B2 (en) | 2004-06-28 | 2007-02-06 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7432373B2 (en) * | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
| US7253167B2 (en) * | 2004-06-30 | 2007-08-07 | Bristol-Myers Squibb Company | Tricyclic-heteroaryl compounds useful as kinase inhibitors |
| TW200600513A (en) * | 2004-06-30 | 2006-01-01 | Bristol Myers Squibb Co | A method for preparing pyrrolotriazine compounds |
| US7102003B2 (en) * | 2004-07-01 | 2006-09-05 | Bristol-Myers Squibb Company | Pyrrolotriazine compounds |
| US7419972B2 (en) * | 2004-07-02 | 2008-09-02 | Schering Ag | 2-substituted estra-1,3,5(10)-trien-17-ones as inhibitors of 17β-hydroxy steroid dehydrogenase type 1 |
| US7504521B2 (en) * | 2004-08-05 | 2009-03-17 | Bristol-Myers Squibb Co. | Methods for the preparation of pyrrolotriazine compounds |
| US7148348B2 (en) | 2004-08-12 | 2006-12-12 | Bristol-Myers Squibb Company | Process for preparing pyrrolotriazine aniline compounds useful as kinase inhibitors |
| US7151176B2 (en) * | 2004-10-21 | 2006-12-19 | Bristol-Myers Squibb Company | Pyrrolotriazine compounds |
| US7514435B2 (en) * | 2005-11-18 | 2009-04-07 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| KR101461680B1 (ko) | 2005-12-02 | 2014-11-19 | 바이엘 헬스케어 엘엘씨 | 과다-증식성 장애 및 맥관형성과 관련된 질환의 치료에유용한 치환된 4-아미노-피롤로트리아진 유도체 |
| PE20070855A1 (es) | 2005-12-02 | 2007-10-14 | Bayer Pharmaceuticals Corp | Derivados de 4-amino-pirrolotriazina sustituida como inhibidores de quinasas |
| US8063208B2 (en) | 2006-02-16 | 2011-11-22 | Bristol-Myers Squibb Company | Crystalline forms of (3R,4R)-4-amino-1-[[4-[(3-methoxyphenyl)amino]pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol |
| AU2007240453B2 (en) * | 2006-04-21 | 2012-04-12 | Bristol-Myers Squibb Company | Process for the preparation of [(1R), 2S]-2-aminopropionic acid 2-[4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy]-1-methylethyl ester |
| US20080112888A1 (en) | 2006-06-30 | 2008-05-15 | Schering Corporation | Igfbp2 biomarker |
| CL2007003158A1 (es) | 2006-11-02 | 2008-05-16 | Astrazeneca Ab | Procedimiento de preparacion de compuestos derivados de quinazolina o sus sales farmaceuticamente aceptables; compuestos intermediarios; procedimiento de preparacion. |
| CN101627116B (zh) * | 2007-02-08 | 2013-07-10 | 科德克希思公司 | 酮还原酶及其用途 |
| RU2010120674A (ru) | 2007-10-22 | 2011-11-27 | Шеринг Корпорейшн (US) | Полностью человеческие анти-vegf-антитела и способы их применения |
| ES2539620T3 (es) | 2008-12-19 | 2015-07-02 | Cephalon, Inc. | Pirrolotriazina como inhibidor de ALK y de JAK2 |
| US8691981B2 (en) * | 2010-02-03 | 2014-04-08 | Bristol-Myers Squibb Company | Crystalline forms of (S)-1-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrrolo[1,2-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide |
| CN102603718B (zh) * | 2012-02-08 | 2014-01-29 | 武汉凯斯瑞科技有限公司 | 西地尼布的合成方法 |
| CN103420892A (zh) * | 2012-05-18 | 2013-12-04 | 苏州爱斯鹏药物研发有限责任公司 | 一种4-氟吲哚的制备方法 |
| US9458137B2 (en) | 2012-11-05 | 2016-10-04 | Nantbioscience, Inc. | Substituted indol-5-ol derivatives and their therapeutical applications |
| US9550760B2 (en) | 2013-03-15 | 2017-01-24 | Nantbioscience, Inc. | Substituted indol-5-ol derivatives and their therapeutic applications |
| WO2015081783A1 (zh) * | 2013-12-06 | 2015-06-11 | 江苏奥赛康药业股份有限公司 | 吡咯并[2,1-f][1,2,4]三嗪类衍生物及其制备方法和用途 |
| US9388239B2 (en) | 2014-05-01 | 2016-07-12 | Consejo Nacional De Investigation Cientifica | Anti-human VEGF antibodies with unusually strong binding affinity to human VEGF-A and cross reactivity to human VEGF-B |
| DK3356345T3 (da) | 2015-09-30 | 2024-02-12 | Max Planck Gesellschaft | Heteroaryl-derivater som sepiapterin-reduktase-inhibitorer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60026297T2 (de) | 1999-05-21 | 2006-11-02 | Bristol-Myers Squibb Co. | Pyrrolotriazin kinasehemmer |
| CA2416525A1 (en) * | 2000-08-09 | 2002-02-14 | Astrazeneca Ab | Indole, azaindole and indazole derivatives having vegf inhibiting activity |
| US6670357B2 (en) | 2000-11-17 | 2003-12-30 | Bristol-Myers Squibb Company | Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors |
| YU37903A (sh) | 2000-11-17 | 2006-05-25 | Bristol-Myers Squibb Company | POSTUPCI LEČENJA STANJA POVEZANIH SA p38 KINAZOM I JEDINJENJA PIROLOTRIAZINA KOJA SE KORISTE KAO INHIBITORI KINAZE |
-
2003
- 2003-07-18 TW TW092119890A patent/TWI272271B/zh not_active IP Right Cessation
- 2003-07-18 US US10/622,280 patent/US6933386B2/en not_active Expired - Lifetime
- 2003-07-21 WO PCT/US2003/022755 patent/WO2004009542A2/en not_active Ceased
- 2003-07-21 EP EP03765846A patent/EP1554281A4/en not_active Withdrawn
- 2003-07-21 IL IL16598503A patent/IL165985A0/xx unknown
- 2003-07-21 AU AU2003256645A patent/AU2003256645A1/en not_active Abandoned
- 2003-07-21 MX MXPA05000344A patent/MXPA05000344A/es active IP Right Grant
- 2003-07-21 PL PL03375316A patent/PL375316A1/xx not_active Application Discontinuation
- 2003-07-21 CN CN038162016A patent/CN1665817A/zh active Pending
- 2003-07-21 JP JP2004523221A patent/JP2006502120A/ja not_active Withdrawn
- 2003-07-21 CA CA002492861A patent/CA2492861A1/en not_active Abandoned
- 2003-07-21 BR BR0312648-0A patent/BR0312648A/pt not_active IP Right Cessation
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