SK284417B6 - Spôsob konverzie derivátov treo-(2R,3R)-2-hydroxy-3-(2- aminofenyltio)-3-(4-metoxyfenyl)propiónovej kyseliny - Google Patents

Spôsob konverzie derivátov treo-(2R,3R)-2-hydroxy-3-(2- aminofenyltio)-3-(4-metoxyfenyl)propiónovej kyseliny Download PDF

Info

Publication number: SK284417B6
Authority: SK; Slovakia
Prior art keywords: acid; iii; formula; compound; methoxyphenyl
Prior art date: 1997-10-22

Application number

SK560-2000A

Other languages

English (en)

Slovak (sk)

Other versions

SK5602000A3 (en

Inventor

Pietro Allegrini

Gaetano Marchioro

Giuseppe Barreca

Marco Villa

Laura Russo

Original Assignee

Zambon Group S. P. A.

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.)

1997-10-22

Filing date

1998-10-12

Publication date

2005-03-04

1998-10-12 Application filed by Zambon Group S. P. A. filed Critical Zambon Group S. P. A.

2000-09-12 Publication of SK5602000A3 publication Critical patent/SK5602000A3/sk

2005-03-04 Publication of SK284417B6 publication Critical patent/SK284417B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 39
238000006243 chemical reaction Methods 0.000 title claims abstract description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
150000001875 compounds Chemical class 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 17
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
229940098779 methanesulfonic acid Drugs 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
150000003460 sulfonic acids Chemical class 0.000 claims description 5
238000007142 ring opening reaction Methods 0.000 claims description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
239000003125 aqueous solvent Substances 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
238000006798 ring closing metathesis reaction Methods 0.000 claims 1
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 abstract description 17
229960004166 diltiazem Drugs 0.000 abstract description 17
238000003786 synthesis reaction Methods 0.000 abstract description 12
230000015572 biosynthetic process Effects 0.000 abstract description 11
239000000543 intermediate Substances 0.000 abstract description 8
239000002699 waste material Substances 0.000 abstract description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000000926 separation method Methods 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
150000004702 methyl esters Chemical class 0.000 description 6
238000007363 ring formation reaction Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
YRWWWPMLATUJOI-UHFFFAOYSA-N [2-(4-methoxyphenyl)-4-oxo-5h-1,5-benzothiazepin-3-yl] acetate Chemical compound C1=CC(OC)=CC=C1C1=C(OC(C)=O)C(=O)NC2=CC=CC=C2S1 YRWWWPMLATUJOI-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
238000004064 recycling Methods 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
-1 sulfonic acids Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XWCIXXXLOAAWPU-IHWYPQMZSA-N [(z)-prop-1-enyl]phosphonic acid Chemical compound C\C=C/P(O)(O)=O XWCIXXXLOAAWPU-IHWYPQMZSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
LHBHZALHFIQJGJ-LSDHHAIUSA-N (2r,3r)-3-hydroxy-2-(4-methoxyphenyl)-3,5-dihydro-2h-1,5-benzothiazepin-4-one Chemical compound C1=CC(OC)=CC=C1[C@@H]1[C@H](O)C(=O)NC2=CC=CC=C2S1 LHBHZALHFIQJGJ-LSDHHAIUSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
LGFTULJJDDFVFE-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5h-1,5-benzothiazepine-3,4-dione Chemical compound C1=CC(OC)=CC=C1C1C(=O)C(=O)NC2=CC=CC=C2S1 LGFTULJJDDFVFE-UHFFFAOYSA-N 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
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 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
239000004367 Lipase Substances 0.000 description 1
102000004882 Lipase Human genes 0.000 description 1
108090001060 Lipase Proteins 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
229950002475 mesilate Drugs 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
XWCIXXXLOAAWPU-UHFFFAOYSA-N prop-1-enylphosphonic acid Chemical compound CC=CP(O)(O)=O XWCIXXXLOAAWPU-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Compounds Of Unknown Constitution (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK560-2000A 1997-10-22 1998-10-12 Spôsob konverzie derivátov treo-(2R,3R)-2-hydroxy-3-(2- aminofenyltio)-3-(4-metoxyfenyl)propiónovej kyseliny SK284417B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT97MI002374A IT1295376B1 (it)	1997-10-22	1997-10-22	Processo per il riciclo di un sottoprodotto della sintesi del diltiazem
PCT/EP1998/006467 WO1999020603A1 (en)	1997-10-22	1998-10-12	Process for the recycle of a waste product of diltiazem synthesis

Publications (2)

Publication Number	Publication Date
SK5602000A3 SK5602000A3 (en)	2000-09-12
SK284417B6 true SK284417B6 (sk)	2005-03-04

Family

ID=11378079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK560-2000A SK284417B6 (sk)	1997-10-22	1998-10-12	Spôsob konverzie derivátov treo-(2R,3R)-2-hydroxy-3-(2- aminofenyltio)-3-(4-metoxyfenyl)propiónovej kyseliny

Country Status (17)

Country	Link
US (1)	US6114523A (de)
EP (1)	EP1025080B1 (de)
JP (1)	JP2001520219A (de)
KR (1)	KR20010031267A (de)
CN (1)	CN1121383C (de)
AT (1)	ATE230724T1 (de)
AU (1)	AU743612B2 (de)
CA (1)	CA2304371A1 (de)
DE (1)	DE69810653T2 (de)
ES (1)	ES2189263T3 (de)
HU (1)	HU225099B1 (de)
IL (1)	IL134534A0 (de)
IT (1)	IT1295376B1 (de)
PL (1)	PL194251B1 (de)
SK (1)	SK284417B6 (de)
WO (1)	WO1999020603A1 (de)
ZA (1)	ZA989559B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003241747A1 (en) *	2002-06-11	2003-12-22	Kaneka Corporation	PROCESS FOR PRODUCING OPTICALLY ACTIVE ss-AMINO ALCOHOL
CN103755663B (zh) *	2014-01-26	2016-02-24	武汉工程大学	地尔硫卓中间体副产物L-cis-内酰胺的回收工艺
CN110284181A (zh) *	2019-08-07	2019-09-27	山东新华制药股份有限公司	地尔硫卓ab异构体的单晶制备方法
CN112279820B (zh) *	2020-12-18	2021-04-02	苏州开元民生科技股份有限公司	2-(4-甲氧苯基)-3-羟基-2,3-二氢-1,5-苯并硫氮杂卓酮的制备方法
CN118684635B (zh) *	2024-08-22	2024-11-05	苏州开元民生科技股份有限公司	一种地尔硫卓手性中间体的制备方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1236467A (en) *	1967-10-28	1971-06-23	Tanabe Seiyaku Co	Benzothiazepine derivatives
EP0059335B1 (de) *	1981-02-27	1985-05-15	Tanabe Seiyaku Co., Ltd.	Verfahren zur Herstellung von threo-2-Hydroxy-3-(-methoxyphenyl)-3-(2-nitrophenylthio)-propionsäureestern
SE449611B (sv) *	1982-07-09	1987-05-11	Tanabe Seiyaku Co	Sett att framstella 1,5-bensotiazepinderivat
IT1152721B (it) *	1982-10-15	1987-01-07	Luso Farmaco Inst	Risoluzione ottica dell'acido dl-alfa-2-idrossi-3-(4-metossifenil)-3-(2-amminofeniltio)propionico
IT1230057B (it) *	1989-04-13	1991-09-27	Zambon Spa	Processo di risoluzione di intermedi utili per la preparazione di 1,5-benzotiazepine
JPH0798813B2 (ja) *	1989-04-28	1995-10-25	田辺製薬株式会社	１，５―ベンゾチアゼピン誘導体の製法
IT1232306B (it) *	1989-07-27	1992-01-28	Zambon Spa	Processo di risoluzione di intermedi utili per la preparazione del diltiazem
IT1237526B (it) *	1989-12-06	1993-06-08	Zambon Spa	Processo di preparazione di un intermedio per il diltiazem
JPH085869B2 (ja) *	1990-03-08	1996-01-24	田辺製薬株式会社	１，５−ベンゾチアゼピン誘導体の製法
NL9000763A (nl) *	1990-03-31	1991-10-16	Stamicarbon	Werkwijze voor het bereiden van 1,5-benzothiazepine-derivaten.
IT1249318B (it) *	1991-05-23	1995-02-22	Zambon Spa	Processo per la preparazione di benzotiazepine per ciclizzazione con acidi fosfonici
FI93741C (fi) *	1993-03-24	1995-05-26	Orion Yhtymae Oy	Menetelmä optisesti puhtaitten (2S,3S)- ja (2R,3R)-threo-alkyyli-2-hydroksi-3-(4-metoksifenyyli)-3-(2-X-fenyylitio)propionaattien tai vastaavien asyloitujen yhdisteiden valmistamiseksi
JPH07108982A (ja) *	1993-10-13	1995-04-25	Nippon Shokubai Co Ltd	浮き桟橋

1997
- 1997-10-22 IT IT97MI002374A patent/IT1295376B1/it active IP Right Grant
1998
- 1998-10-12 EP EP98954403A patent/EP1025080B1/de not_active Expired - Lifetime
- 1998-10-12 ES ES98954403T patent/ES2189263T3/es not_active Expired - Lifetime
- 1998-10-12 AU AU11531/99A patent/AU743612B2/en not_active Ceased
- 1998-10-12 DE DE69810653T patent/DE69810653T2/de not_active Expired - Lifetime
- 1998-10-12 CN CN98809527A patent/CN1121383C/zh not_active Expired - Fee Related
- 1998-10-12 CA CA002304371A patent/CA2304371A1/en not_active Abandoned
- 1998-10-12 IL IL13453498A patent/IL134534A0/xx not_active IP Right Cessation
- 1998-10-12 PL PL98339054A patent/PL194251B1/pl not_active IP Right Cessation
- 1998-10-12 HU HU0100997A patent/HU225099B1/hu not_active IP Right Cessation
- 1998-10-12 AT AT98954403T patent/ATE230724T1/de active
- 1998-10-12 WO PCT/EP1998/006467 patent/WO1999020603A1/en not_active Ceased
- 1998-10-12 KR KR1020007004254A patent/KR20010031267A/ko not_active Ceased
- 1998-10-12 SK SK560-2000A patent/SK284417B6/sk unknown
- 1998-10-12 JP JP2000516945A patent/JP2001520219A/ja active Pending
- 1998-10-20 ZA ZA989559A patent/ZA989559B/xx unknown
- 1998-10-21 US US09/176,189 patent/US6114523A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1271340A (zh)	2000-10-25
HUP0100997A2 (hu)	2001-08-28
JP2001520219A (ja)	2001-10-30
ITMI972374A1 (it)	1999-04-22
PL339054A1 (en)	2000-12-04
IL134534A0 (en)	2001-04-30
ES2189263T3 (es)	2003-07-01
WO1999020603A1 (en)	1999-04-29
AU1153199A (en)	1999-05-10
CN1121383C (zh)	2003-09-17
US6114523A (en)	2000-09-05
SK5602000A3 (en)	2000-09-12
KR20010031267A (ko)	2001-04-16
EP1025080B1 (de)	2003-01-08
EP1025080A1 (de)	2000-08-09
ZA989559B (en)	1999-04-22
CA2304371A1 (en)	1999-04-29
AU743612B2 (en)	2002-01-31
DE69810653D1 (de)	2003-02-13
ATE230724T1 (de)	2003-01-15
DE69810653T2 (de)	2003-11-13
PL194251B1 (pl)	2007-05-31
IT1295376B1 (it)	1999-05-12
HU225099B1 (en)	2006-06-28
HUP0100997A3 (en)	2002-11-28

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SK284417B6 (sk)	2005-03-04	Spôsob konverzie derivátov treo-(2R,3R)-2-hydroxy-3-(2- aminofenyltio)-3-(4-metoxyfenyl)propiónovej kyseliny
EP0939135A1 (de)	1999-09-01	Wesentlich saubere hetero-bicyclische Alkohol-Enantiomeren
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EP1140842B1 (de)	2005-11-02	Ester von 3-(3,4-dihalogenophenyl)-2,6-dioxopiperidine-3-propionsäure als zwischenprodukte
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KR20030083732A (ko)	2003-10-30	비시클로카르복실산 유도체의 제조 방법
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FI107605B (fi)	2001-09-14	Optisesti aktiivinen 2-[1-(4-t-butyylifenyyli)-2-pyrrolidoni-4-yyli]metoksikarbonyylibentsoehapon alfa-fenyylietyyliamidi, välituote ja menetelmä sen valmistamiseksi
FR2633622A1 (fr)	1990-01-05	Derives de sulfonyl indolizine, leur procede de preparation et leur utilisation comme intermediaires de synthese
EP0370366A2 (de)	1990-05-30	Verfahren zur Racematspaltung von Benzazepinzwischenprodukten
HU213569B (en)	1997-08-28	Enzymatic process for the stereoselective preparation of a heterobicyclic alcohol enantiomer
CZ2005431A3 (cs)	2007-02-07	Zpusob prípravy mykofenolátu mofetilu
FR2798127A1 (fr)	2001-03-09	Nouveau procede de preparation d'amidines derivees de l'acide 6-hydroxy-2,5,7,8-tetramethylchrommane-2-carboxy- lique