IL136357A - Processes for preparing the history of the N-converted heterocyclic compounds - Google Patents

Processes for preparing the history of the N-converted heterocyclic compounds

Info

Publication number: IL136357A
Authority: IL; Israel
Prior art keywords: organic solvent; butyl; formula; diazaspiro; methyl
Prior art date: 1998-01-30

Application number

IL13635799A

Other languages

English (en)

Hebrew (he)

Original Assignee

Bristol Myers Squibb Co

Priority date (The priority date 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 date listed.)

1998-01-30

Filing date

1999-01-20

Publication date

2004-07-25

1999-01-20 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2004-07-25 Publication of IL136357A publication Critical patent/IL136357A/en

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)
Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL13635799A 1998-01-30 1999-01-20 Processes for preparing the history of the N-converted heterocyclic compounds IL136357A (en)

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 (en)	2004-07-25

Family

ID=22111745

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13635799A IL136357A (en)	1998-01-30	1999-01-20	Processes for preparing the history of the N-converted heterocyclic compounds

Country Status (15)

Country	Link
US (1)	US6162922A (fr)
EP (1)	EP1060165B1 (fr)
JP (2)	JP4441114B2 (fr)
KR (1)	KR100546530B1 (fr)
AT (1)	ATE275135T1 (fr)
AU (1)	AU743018B2 (fr)
CA (1)	CA2318791A1 (fr)
DE (1)	DE69919849T2 (fr)
DK (1)	DK1060165T3 (fr)
ES (1)	ES2228006T3 (fr)
HU (1)	HU226770B1 (fr)
IL (1)	IL136357A (fr)
PT (1)	PT1060165E (fr)
TW (1)	TWI229076B (fr)
WO (1)	WO1999038847A1 (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
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 (fr) *	2003-11-28	2005-06-09	Ranbaxy Laboratories Limited	Procédés de préparation d'irbesartan très pur
EP1751123A4 (fr) *	2004-05-20	2010-06-30	Reddys Lab Ltd Dr	Processus pour préparer de l'irbésartan
DE602005025755D1 (de)	2004-06-04	2011-02-17	Teva Pharma	Irbesartan enthaltende pharmazeutische zusammensetzung
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.
WO2007013101A1 (fr) *	2005-07-27	2007-02-01	Jubilant Organosys Limited	Procédé de production de 2-(n-butyl)-3-[[2'-(tétrazol-5-yl)biphényl- 4-yl]méthyl]-l,3-diazaspiro[4.4] non-1-en-4-one
EP1764365A1 (fr)	2005-09-20	2007-03-21	KRKA, D.D., Novo Mesto	Méthode de préparation de dérivés de sartan et des intermédiaires servant à un tel procédé
ES2371910T3 (es)	2006-04-07	2012-01-11	Lek Pharmaceuticals D.D.	Procedimiento para la preparación de irbesartán puro.
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 (fr) *	2007-01-18	2008-07-24	Rainbow Engineering Services	Nouveaux composés
US7671273B2 (en)	2007-10-09	2010-03-02	International Business Machines Corporation	Method and apparatus for facilitating signal transmission using differential transmission lines
EP2417110B1 (fr) *	2009-04-08	2014-05-07	CTX Life Sciences Pvt. Ltd.	Procédé monotope de préparation de la 2-butyl-3-[[2'-(1h-tétrazol-5-yl)[1,1'-biphényl]-4-yl]méthyl]-1,3-diazaspiro[4,4]non-1-én-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
CN110487931B (zh) *	2019-08-21	2024-10-01	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 (fr)	2020-10-30	2022-05-05	Encodia, Inc.	Réactifs de conjugaison et méthodes utilisant des 1,2-cyclohexanediones

Family Cites Families (10)

* Cited by examiner, † Cited by third party
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
TW201738B (fr) *	1990-03-20	1993-03-11	Sanofi Co
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.
WO1993004045A1 (fr) *	1991-08-19	1993-03-04	E.I. Du Pont De Nemours And Company	Derives d'imidazolinone d'inhibition de l'action de l'angiotensine ii sur ses recepteurs
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 EP EP99904158A patent/EP1060165B1/fr not_active Expired - Lifetime
- 1999-01-20 JP JP2000530084A patent/JP4441114B2/ja not_active Expired - Lifetime
- 1999-01-20 HU HU0100898A patent/HU226770B1/hu unknown
- 1999-01-20 DK DK99904158T patent/DK1060165T3/da active
- 1999-01-20 AU AU24615/99A patent/AU743018B2/en not_active Expired
- 1999-01-20 KR KR1020007008302A patent/KR100546530B1/ko not_active Expired - Lifetime
- 1999-01-20 IL IL13635799A patent/IL136357A/en not_active IP Right Cessation
- 1999-01-20 WO PCT/US1999/001201 patent/WO1999038847A1/fr not_active Ceased
- 1999-01-20 DE DE69919849T patent/DE69919849T2/de not_active Expired - Lifetime
- 1999-01-20 ES ES99904158T patent/ES2228006T3/es not_active Expired - Lifetime
- 1999-01-20 PT PT99904158T patent/PT1060165E/pt unknown
- 1999-01-20 CA CA002318791A patent/CA2318791A1/fr not_active Abandoned
- 1999-01-20 AT AT99904158T patent/ATE275135T1/de active
- 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
ATE275135T1 (de)	2004-09-15
KR20010034477A (ko)	2001-04-25
TWI229076B (en)	2005-03-11
EP1060165A1 (fr)	2000-12-20
HU226770B1 (en)	2009-09-28
HUP0100898A3 (en)	2002-03-28
JP2010018638A (ja)	2010-01-28
JP2002501946A (ja)	2002-01-22
HUP0100898A2 (hu)	2002-02-28
WO1999038847A1 (fr)	1999-08-05
KR100546530B1 (ko)	2006-01-26
AU743018B2 (en)	2002-01-17
US6162922A (en)	2000-12-19
AU2461599A (en)	1999-08-16
EP1060165B1 (fr)	2004-09-01
PT1060165E (pt)	2004-12-31
DK1060165T3 (da)	2004-11-22
ES2228006T3 (es)	2005-04-01
DE69919849T2 (de)	2005-09-22
CA2318791A1 (fr)	1999-08-05
DE69919849D1 (de)	2004-10-07
EP1060165A4 (fr)	2002-07-31
JP4441114B2 (ja)	2010-03-31

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2019-08-29	EXP	Patent expired

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WO2005122699A2 (fr)	2005-12-29	Procede ameliore de preparation de derives heterocycliques n-substitues
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