LV11324B - Method for the preparation of 3-hydroxy-5-£2-(dimethylamino)-ethyl|-2,3-dihydro-2-(4-methoxyphenyl)-1,5- benzothiazepin-4(5h)-one and use of the product for making pharmaceutically active compounds - Google Patents

Method for the preparation of 3-hydroxy-5-£2-(dimethylamino)-ethyl|-2,3-dihydro-2-(4-methoxyphenyl)-1,5- benzothiazepin-4(5h)-one and use of the product for making pharmaceutically active compounds Download PDF

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Publication number
LV11324B
LV11324B LVP-95-283A LV950283A LV11324B LV 11324 B LV11324 B LV 11324B LV 950283 A LV950283 A LV 950283A LV 11324 B LV11324 B LV 11324B
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LV
Latvia
Prior art keywords
salt
butanone
formula
dimethylamino
benzothiazepine
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Application number
LVP-95-283A
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English (en)
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LV11324A (lv
Inventor
Martti Hytoenen
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Orion Corp Fermion
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Publication date
Application filed by Orion Corp Fermion filed Critical Orion Corp Fermion
Publication of LV11324A publication Critical patent/LV11324A/lv
Publication of LV11324B publication Critical patent/LV11324B/en

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • General Health & Medical Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (11)

  1. LV 11324 Izgudrojuma formula 1. Paņēmiens cis-(+)-3-hidroksi-5-[2-(dimetilamino)etil]-2,3-dihidro-2-(4-metoksifenil)-1,5-benzotiazepīn-4(5H)-ona ar formulu (I) OCHj
    vai tā sāls iegūšanai, alkilējot benzotiazepīna atvasinājumu ar formulu (II), vai tā sāli:
    1 ar 2-(dimetilamino)etilhalogenidu, vai tā sāli kālija karbonāta vai kālija hidroksīda klātienē, kas atšķiras ar to, ka alkilēšanu veic vidē, kura satur 2-butanonu un ūdeni.
  2. 2. Paņēmiens pēc 1. punkta, kas atšķiras ar to, ka ūdens ņemts vismaz 0,4 moli uz molu 2-butanona.
  3. 3. Paņēmiens pēc 1. punkta, kas atšķiras ar to, ka ūdens ņemts vismaz 0,6 moli uz molu 2-butanona.
  4. 4. Paņēmiens pēc 1. punkta, kas atšķiras ar to, ka ūdens ņemts no 0,7 līdz 0,9 moliem uz molu 2-butanona.
  5. 5. Paņēmiens pēc jebkura no iepriekšējiem punktiem, kas atšķiras ar to, ka kālija karbonāts vai kālija hidroksīds ņemts no 3 līdz 3,5 moliem uz molu benzotiazepīna atvasinājuma ar formulu (III) vai tā sāls.
  6. 6. Paņēmiens pēc jebkura no iepriekšējiem punktiem, kas atšķiras ar to, ka 2-butanons ņemts no 1,3 līdz 1,9 moli uz moliem benzotiazepīna atvasinājuma ar formulu (III) vai tā sāls.
  7. 7. Paņēmiens pēc jebkura no iepriekšējiem punktiem, kas atšķiras ar to, ka 2-(dimetilamino)etilhalogenīds vai tā sāls ņemts no 1,05 līdz 1,18 moliem uz molu benzotiazepīna atvasinājuma ar formulu (III) vai tā sāls.
  8. 8. Paņēmiens pēc jebkura no iepriekšējiem punktiem, kas atšķiras ar to, ka 2-(dimetilamino)etilhalogenīds vai tā sāls ir 2-(dimetilamino)etilhlorīds vai tā sāls.
  9. 9. Paņēmiens pēc jebkura no iepriekšējiem punktiem, kas atšķiras ar to, ka procesu veic laikā no 50 minūtēm līdz 2,5 stundām, pēc tam reakcijas maisījumam pievieno ūdeni, izveidojušos ūdens fāzi atdala no produktu saturošās organiskās fāzes un no organiskās produktu saturošās fāzes aizvāc 2-butanonu.
  10. 10. Paņēmiens benzotiazepīna atvasinājumu ar formulu (la1) vai to farmaceitiski pieņemamas sāls iegūšanai
    LV 11324 kas atšķiras ar to, ka pēc jebkura no 1 .-9. punktiem iegūtais benzotiazepīns ar formulu (I) tiek tālāk acilēts stāvoklī 3 ar aktīvu reaģentu, piemēram, karbonskābes hlorīdu, karbonskābes anhidrīdu, aktivētā estera tipa atvasinājumu vai savienojumu ar formulu R2 -Y-COOH (III) vai tā sāli, kur R2 ir cikloalkilgrupa, zemākā alkoksikarbonilgrupa, COOH, zemākā alkanoilgrupa, heterociklisks aizvietotājs, halogēna atoms, zemākā alkilgrupa, zemākā alkoksigrupa, aralkoksigrupa, mono-, di- vai trihalogēn-alkilgrupa, hidroksilgrupa, ariloksigrupa, aminogrupa, acilaminogrupa, zemākā aliltiogrupa, zemākā alkilsulfinilgrupa, zemākā alkilsulfonilgrupa, di(zemākā alkilgrupa)aminosulfonilgrupa, arilkarbonilgrupa, zemākā alkoksikarbonilgrupa, vai fenilgrupa, kas neobligāti aizvietota ar 1-3 aizvietotājiem, un Y ir saite, zemākā alkilēngrupa vai zemākā alkilēnoksigrupa, ar zināmu paņēmienu, kas atšķiras ar to, ka acilēšanas reakciju veic neizdalot starpproduktu, tieši pēc alkilēšanas reakcijas, un ūdens un 2-butanona aizvākšanas no reakcijas maisījuma, bez. starpprodukta attīrīšanas vai pārkristalizēšanas posma pirms acilēšanas reakcijas posma un, neobligāti pārvēršot acilēto produktu (la’) par tā farmaceitiski pieņemamu sāli.
  11. 11. Paņēmiens cis-(+)-3-acetoksi-5-[2-(dimetilamino)etil]-2,3-dihidro-2-(4-metoksifenil)-1,5-benzotiazepīn-4(5H)-ona ar formulu (la) vai tā farmaceitiski pieņemamas sāls
    iegūšanai pēc 10. punkta, kurā pēc jebkura no 1.-9. punktiem iegūtais benzotiazepīns ar formulu (I) tiek tālāk acetilēts stāvoklī 3 ar zināmu paņēmienu, kas atšķiras ar to, ka acetilēšanas reakciju veic neizdalot starpproduktu, tieši pēc alkilēšanas reakcijas, un ūdens un 2-butanona aizvākšanas no reakcijas maisījuma, bez starpprodukta attīrīšanas vai pārkristalizēšanas posma pirms acetilēšanas reakcijas posma un, neobligāti pārvēršot acilēto produktu (la) par tā farmaceitiski pieņemamu sāli. 3
LVP-95-283A 1994-09-16 1995-09-15 Method for the preparation of 3-hydroxy-5-£2-(dimethylamino)-ethyl|-2,3-dihydro-2-(4-methoxyphenyl)-1,5- benzothiazepin-4(5h)-one and use of the product for making pharmaceutically active compounds LV11324B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP94114643A EP0702009B1 (en) 1994-09-16 1994-09-16 Method for the preparation of pharmaceutically active benzothiazepine derivatives

Publications (2)

Publication Number Publication Date
LV11324A LV11324A (lv) 1996-06-20
LV11324B true LV11324B (en) 1996-10-20

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Country Status (20)

Country Link
US (1) US5663332A (lv)
EP (1) EP0702009B1 (lv)
JP (1) JPH08269026A (lv)
AT (1) ATE167858T1 (lv)
BA (1) BA95040A (lv)
CA (1) CA2158223A1 (lv)
CZ (1) CZ290970B6 (lv)
DE (1) DE69411387T2 (lv)
DK (1) DK0702009T3 (lv)
EE (1) EE03565B1 (lv)
ES (1) ES2118292T3 (lv)
HR (1) HRP950478B1 (lv)
HU (1) HU220610B1 (lv)
IL (1) IL115275A (lv)
LV (1) LV11324B (lv)
PL (1) PL310495A1 (lv)
RU (1) RU2141957C1 (lv)
SK (1) SK281219B6 (lv)
YU (1) YU60395A (lv)
ZA (1) ZA957703B (lv)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996038429A1 (en) * 1995-06-01 1996-12-05 Acic (Canada) Inc. Method for the manufacture of benzothiazepine derivatives
IL123352A0 (en) 1997-02-27 1998-09-24 Tanabe Seiyaku Co Process for preparing an optically active trans-3-substituted glycidic acid ester
DE102004010830A1 (de) * 2004-02-27 2005-09-15 Bioagency Ag Neue 1,4-Benzooxazepane oder 1,4-Benzothiazepane und Derivate
CN103304514B (zh) * 2013-06-28 2014-09-17 天津梅花医药有限公司 一种稳定性好的盐酸地尔硫卓化合物及药物组合物

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3562257A (en) * 1967-10-28 1971-02-09 Tanabe Seiyaku Co Benzothiazepine derivatives
JPS5899471A (ja) * 1981-12-07 1983-06-13 Tanabe Seiyaku Co Ltd ベンゾチアゼピン誘導体の新規製造法
IT1175814B (it) * 1984-03-09 1987-07-15 Luso Farmaco Inst Resine solfoniche ad attivita' terapeutica,loro preparazione e composizioni farmaceutiche che le contengono
JPS63275572A (ja) * 1987-05-01 1988-11-14 Tanabe Seiyaku Co Ltd １，５−ベンゾチアゼピン誘導体
FR2624117B1 (fr) * 1987-12-08 1991-02-22 Synthelabo Derives de hydroxy-3 (methoxy-4 phenyl)-2 (methylamino-2 ethyl)-5 dihydro-2,3 5h-benzothiazepine-1,5 one-4, leur preparation et leur application en therapeutique
FR2630109B1 (fr) * 1988-04-19 1991-11-29 Synthelabo Derives de ((n-(amino-2 oxo-2 ethyl)methylamino)-2 ethyl)-5 hydroxy-3 (methoxy-4 phenyl)-2 dihydro-2,3 5h-benzothiazepine-1,5 one-4, leur preparation et leur application en therapeutique
US5002942A (en) * 1988-07-25 1991-03-26 Sankyo Company, Limited 1,5-benzothiazepine derivatives, their preparation and their use in the treatment of cardiovascular disorders
FR2653122B1 (fr) * 1989-10-17 1994-04-15 Synthelabo Derives de 5-[2-[[2-amino-2-oxoethyl]methylamino]ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5(5h)-benzothiazepine-4-one, leur preparation et leur application en therapeutique.
IT1240686B (it) * 1990-04-27 1993-12-17 Luso Farmaco Inst Derivati 1,5-benzotiazepinonici, loro preparazione e uso farmaceutico
IT1244878B (it) * 1990-12-11 1994-09-12 Lusochimica Spa Processo per la preparazione del (+)-cis-3-(acetossi)-5-!2-( dimetilammino)etil!-2,3-diidro-2-(4-metossifenil)-1,5-benzotiazepin- 4-(5h)-one cloridrato

Also Published As

Publication number Publication date
SK281219B6 (sk) 2001-01-18
SK114195A3 (en) 1996-06-05
HUT76924A (hu) 1998-01-28
EP0702009A1 (en) 1996-03-20
HU220610B1 (hu) 2002-03-28
DK0702009T3 (da) 1999-02-01
HRP950478A2 (en) 1997-06-30
CZ290970B6 (cs) 2002-11-13
HRP950478B1 (en) 1999-10-31
DE69411387D1 (de) 1998-08-06
RU2141957C1 (ru) 1999-11-27
DE69411387T2 (de) 1999-02-25
EE9500050A (et) 1996-04-15
JPH08269026A (ja) 1996-10-15
CA2158223A1 (en) 1996-03-17
EE03565B1 (et) 2001-12-17
ATE167858T1 (de) 1998-07-15
EP0702009B1 (en) 1998-07-01
HU9502710D0 (en) 1995-11-28
ZA957703B (en) 1996-04-24
CZ237295A3 (en) 1996-04-17
IL115275A0 (en) 1995-12-31
LV11324A (lv) 1996-06-20
IL115275A (en) 2000-06-01
YU60395A (sh) 1998-09-18
BA95040A (bs) 1998-12-28
PL310495A1 (en) 1996-03-18
US5663332A (en) 1997-09-02
ES2118292T3 (es) 1998-09-16

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