IL136357A - תהליכים להכנת תולדות תרכובות הטרוציקליות המותמרות ב- n - Google Patents
תהליכים להכנת תולדות תרכובות הטרוציקליות המותמרות ב- nInfo
- Publication number
- IL136357A IL136357A IL13635799A IL13635799A IL136357A IL 136357 A IL136357 A IL 136357A IL 13635799 A IL13635799 A IL 13635799A IL 13635799 A IL13635799 A IL 13635799A IL 136357 A IL136357 A IL 136357A
- Authority
- IL
- Israel
- Prior art keywords
- organic solvent
- butyl
- formula
- diazaspiro
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 125000000623 heterocyclic group Chemical class 0.000 title description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 31
- TYBCSQFBSWACAA-UHFFFAOYSA-N Nonan-4-one Chemical compound CCCCCC(=O)CCC TYBCSQFBSWACAA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 238000001704 evaporation Methods 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000004970 halomethyl group Chemical group 0.000 claims abstract 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 29
- 239000004305 biphenyl Substances 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 11
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical group [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 4
- -1 methoxy, ethoxy Chemical group 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000029936 alkylation Effects 0.000 description 9
- 238000005804 alkylation reaction Methods 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 7
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 7
- 229960002198 irbesartan Drugs 0.000 description 7
- 238000003408 phase transfer catalysis Methods 0.000 description 7
- 108010064733 Angiotensins Proteins 0.000 description 6
- 102000015427 Angiotensins Human genes 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052987 metal hydride Inorganic materials 0.000 description 3
- 150000004681 metal hydrides Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 239000000813 peptide hormone Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000734 Angiotensin-1 Proteins 0.000 description 1
- 102400000344 Angiotensin-1 Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- 102000004881 Angiotensinogen Human genes 0.000 description 1
- 108090001067 Angiotensinogen Proteins 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 230000010740 Hormone Receptor Interactions Effects 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
- 102100028255 Renin Human genes 0.000 description 1
- 108090000783 Renin Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940124572 antihypotensive agent Drugs 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000036454 renin-angiotensin system Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7310398P | 1998-01-30 | 1998-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL136357A true IL136357A (he) | 2004-07-25 |
Family
ID=22111745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13635799A IL136357A (he) | 1998-01-30 | 1999-01-20 | תהליכים להכנת תולדות תרכובות הטרוציקליות המותמרות ב- n |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6162922A (he) |
| EP (1) | EP1060165B1 (he) |
| JP (2) | JP4441114B2 (he) |
| KR (1) | KR100546530B1 (he) |
| AT (1) | ATE275135T1 (he) |
| AU (1) | AU743018B2 (he) |
| CA (1) | CA2318791A1 (he) |
| DE (1) | DE69919849T2 (he) |
| DK (1) | DK1060165T3 (he) |
| ES (1) | ES2228006T3 (he) |
| HU (1) | HU226770B1 (he) |
| IL (1) | IL136357A (he) |
| PT (1) | PT1060165E (he) |
| TW (1) | TWI229076B (he) |
| WO (1) | WO1999038847A1 (he) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU218680B (hu) * | 1997-07-25 | 2000-10-30 | Sanofi-Synthelabo | Eljárás 1,3-diaza-spiro[4,4]non-1-én-4-on-származékok előállítására és 1-ciano-1-(acil-amino)-ciklopentán intermedierek |
| CN1668612A (zh) * | 2002-07-16 | 2005-09-14 | 特瓦制药工业有限公司 | 厄贝沙坦的新合成方法 |
| WO2005051943A1 (en) * | 2003-11-28 | 2005-06-09 | Ranbaxy Laboratories Limited | Processes for the preparation of highly pure irbesartan |
| WO2005113518A1 (en) * | 2004-05-20 | 2005-12-01 | Dr. Reddy's Laboratories Ltd. | Process for preparing irbesartan |
| CA2568640C (en) | 2004-06-04 | 2011-08-09 | Teva Pharmaceutical Industries Ltd. | Pharmaceutical composition containing irbesartan |
| SI21848A (sl) * | 2004-07-29 | 2006-02-28 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Priprava seskvihidratne hidrokloridne soli tetrazolskega derivata |
| TWI346108B (en) * | 2004-08-23 | 2011-08-01 | Bristol Myers Squibb Co | A method for preparing irbesartan and intermediates thereof |
| GB2419592A (en) * | 2004-10-26 | 2006-05-03 | Cipla Ltd | Process for the preparation of irbesartan hydrochloride |
| ES2259909B1 (es) * | 2005-02-28 | 2007-06-16 | Inke, S.A. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo y de su intermedio de sintesis. |
| EP1951714A1 (en) | 2005-07-27 | 2008-08-06 | Jubilant Organosys Limited | Process for producing 2-(n-butyl)-3-[[2'-(tetrazol-5-yl)biphenyl- 4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one |
| EP1764365A1 (en) * | 2005-09-20 | 2007-03-21 | KRKA, D.D., Novo Mesto | A process for the preparation of sartan derivates and intermediates useful in such process |
| WO2007115990A1 (en) * | 2006-04-07 | 2007-10-18 | Lek Pharmaceuticals D.D. | Process for the preparation of pure irbesartan |
| CN100413853C (zh) * | 2006-09-21 | 2008-08-27 | 浙江海正药业股份有限公司 | 厄贝沙坦的合成中间体及其制备方法和制备药物的用途 |
| WO2008087401A1 (en) * | 2007-01-18 | 2008-07-24 | Rainbow Engineering Services | Sulfate salts of irbesartan and their preparation and pharmaceutical compositions |
| US7671273B2 (en) | 2007-10-09 | 2010-03-02 | International Business Machines Corporation | Method and apparatus for facilitating signal transmission using differential transmission lines |
| EP2417110B1 (en) * | 2009-04-08 | 2014-05-07 | CTX Life Sciences Pvt. Ltd. | A one pot process for preparing 2-butyl-3-[[2'-(1h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1,3-diazaspiro [4, 4]non-1-en-4-one (irbesartan) |
| CN101781287B (zh) * | 2010-03-26 | 2013-03-20 | 天津大学 | 一种厄贝沙坦氢溴酸盐及其制备方法 |
| CN110487931A (zh) * | 2019-08-21 | 2019-11-22 | 浙江华海药业股份有限公司 | 一种(e)-4-苯基-4-氧代-2-丁烯酸乙酯的分析方法 |
| WO2022094148A1 (en) * | 2020-10-30 | 2022-05-05 | Encodia, Inc. | Conjugation reagents and methods using 1,2-cyclohexanediones |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5270317A (en) * | 1990-03-20 | 1993-12-14 | Elf Sanofi | N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions in which they are present |
| NZ237476A (en) * | 1990-03-20 | 1994-01-26 | Sanofi Sa | N-substituted heterocyclic compounds and pharmaceutical compositions. |
| IL99372A0 (en) * | 1990-09-10 | 1992-08-18 | Ciba Geigy Ag | Azacyclic compounds |
| US5126342A (en) * | 1990-10-01 | 1992-06-30 | Merck & Co., Inc. | Imidazole angiotensin ii antagonists incorporating acidic functional groups |
| FR2673427B1 (fr) * | 1991-03-01 | 1993-06-18 | Sanofi Elf | Derives heterocycliques diazotes n-substitues par un groupement biphenylmethyle, leur preparation, les compositions pharmaceutiques en contenant. |
| JPH06510762A (ja) * | 1991-08-19 | 1994-12-01 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | アンジオテンシン２受容体遮断イミダゾリノン誘導体 |
| FR2688781B1 (fr) * | 1992-03-23 | 1994-07-01 | Sanofi Elf | Imidazolines n-substituees par un groupement biphenylmethyle, leur preparation, les compositions pharmaceutiques en contenant. |
| FR2689887B1 (fr) * | 1992-04-13 | 1995-06-23 | Sanofi Elf | Procede de preparation d'un derive de biphenyle. |
| JP2707390B2 (ja) * | 1992-05-22 | 1998-01-28 | 壽製薬株式会社 | シクロヘプトイミダゾ−ル誘導体及びその製造方法並びにこれを含有する薬剤 |
| US5612363A (en) * | 1995-06-02 | 1997-03-18 | Berlex Laboratories, Inc. | N,N-di(aryl) cyclic urea derivatives as anti-coagulants |
-
1999
- 1999-01-19 US US09/233,238 patent/US6162922A/en not_active Expired - Lifetime
- 1999-01-20 AU AU24615/99A patent/AU743018B2/en not_active Expired
- 1999-01-20 KR KR1020007008302A patent/KR100546530B1/ko not_active IP Right Cessation
- 1999-01-20 HU HU0100898A patent/HU226770B1/hu unknown
- 1999-01-20 CA CA002318791A patent/CA2318791A1/en not_active Abandoned
- 1999-01-20 DE DE69919849T patent/DE69919849T2/de not_active Expired - Lifetime
- 1999-01-20 DK DK99904158T patent/DK1060165T3/da active
- 1999-01-20 JP JP2000530084A patent/JP4441114B2/ja not_active Expired - Lifetime
- 1999-01-20 AT AT99904158T patent/ATE275135T1/de active
- 1999-01-20 IL IL13635799A patent/IL136357A/he not_active IP Right Cessation
- 1999-01-20 ES ES99904158T patent/ES2228006T3/es not_active Expired - Lifetime
- 1999-01-20 PT PT99904158T patent/PT1060165E/pt unknown
- 1999-01-20 EP EP99904158A patent/EP1060165B1/en not_active Expired - Lifetime
- 1999-01-20 WO PCT/US1999/001201 patent/WO1999038847A1/en active IP Right Grant
- 1999-01-26 TW TW088101130A patent/TWI229076B/zh not_active IP Right Cessation
-
2009
- 2009-10-28 JP JP2009247745A patent/JP2010018638A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES2228006T3 (es) | 2005-04-01 |
| PT1060165E (pt) | 2004-12-31 |
| AU2461599A (en) | 1999-08-16 |
| EP1060165A1 (en) | 2000-12-20 |
| EP1060165A4 (en) | 2002-07-31 |
| CA2318791A1 (en) | 1999-08-05 |
| JP4441114B2 (ja) | 2010-03-31 |
| KR20010034477A (ko) | 2001-04-25 |
| WO1999038847A1 (en) | 1999-08-05 |
| EP1060165B1 (en) | 2004-09-01 |
| TWI229076B (en) | 2005-03-11 |
| HU226770B1 (en) | 2009-09-28 |
| JP2002501946A (ja) | 2002-01-22 |
| AU743018B2 (en) | 2002-01-17 |
| HUP0100898A2 (hu) | 2002-02-28 |
| KR100546530B1 (ko) | 2006-01-26 |
| HUP0100898A3 (en) | 2002-03-28 |
| DE69919849T2 (de) | 2005-09-22 |
| ATE275135T1 (de) | 2004-09-15 |
| JP2010018638A (ja) | 2010-01-28 |
| DK1060165T3 (da) | 2004-11-22 |
| DE69919849D1 (de) | 2004-10-07 |
| US6162922A (en) | 2000-12-19 |
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