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FI117755B - Förfarande för framställning av ett terapeutiskt aktivt, optiskt rent natrium- eller magnesiumsalt av pyridinylmetylsulfinyl-1H-bensimidazolförening - Google Patents

Förfarande för framställning av ett terapeutiskt aktivt, optiskt rent natrium- eller magnesiumsalt av pyridinylmetylsulfinyl-1H-bensimidazolförening Download PDF

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Publication number
FI117755B
FI117755B FI950377A FI950377A FI117755B FI 117755 B FI117755 B FI 117755B FI 950377 A FI950377 A FI 950377A FI 950377 A FI950377 A FI 950377A FI 117755 B FI117755 B FI 117755B
Authority
FI
Finland
Prior art keywords
methoxy
dimethyl
methyl
pyridinyl
benzimidazole
Prior art date
Application number
FI950377A
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English (en)
Finnish (fi)
Other versions
FI950377A0 (sv
FI950377L (sv
Inventor
Per Lennart Lindberg
Unge Sverker Von
Original Assignee
Astrazeneca Ab
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.)
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Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20390088&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FI117755(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of FI950377A0 publication Critical patent/FI950377A0/sv
Publication of FI950377L publication Critical patent/FI950377L/sv
Application granted granted Critical
Publication of FI117755B publication Critical patent/FI117755B/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)

Claims (12)

1. Förfarande för framställning av en terapeutiskt aktiv förening som utgörs av ett optiskt rent Na+- eller Mg2+-salt av (-)-5-metoxi-2-[[(4-metoxi-3,5-dimetyl-2-py-10 ridinyl)metyl]sulfmyl]-lH-bensimidazol i fast tillständ, kännetecknat av att a) en diastereomer blandning av en ester med formeln IV ?CH3 H3C\/^^CH3 S_ N CH2-S-^ ~j-OCH3 N" CH2—OAcyl (IV) ·*· • «· ♦ · * · • ·· jv< 15 väri Acyl betecknar en kiral acylgrupp med antingen R- eller S-konfiguration, sepä-• · reras för erhällande av separerade diastereomerer, varefter diastereomeren som /”* omfattar acyloximetylderivatet av (-)-5-metoxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridi- • « · · nyl)metyl]sulfinyl]-lH-bensimidazol upplöses i en basisk lösning väri acylioxime- * tylgruppen avhydrolyseras för erhällande av (-)-5-metoxi-2-[[(4-metoxi-3,5-dimetyl- 20 2-pyridinyl)metyl]sulfinyl]-lH-bensimidazol som överförs tili det önskade optiskt :.:,ϊ rena natrium-eller magnesiumsaltet, eller t · · • · • · b) (-)-enantiomeren av 5-metoxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)mctyl]sulfi- *·· * nyl]-lH-bensimidazol behandlas med en bas innehällande katjonen Na+ eller Mg2+ • * * för erhällande av det önskade optiskt rena natrium- eller magnesiumsaltet av (-)-5-25 metoxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfinyl]-lH-bensimidazol. • · * « · • · • · • · · 19 1 1 7755
2. Förfarande enligt patentkrav 1, kännetecknat av att Na+- eller Mg2+-saltet av (-)-5-metoxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfInyl]-1 H-bensimi-dazol framställs.
3. Förfarande enligt patentkrav 1, kännetecknat av att Mg2+-saltet av (-)-5-me-5 toxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfmyl]-lH-bensimidazol framställs.
4. Förfarande enligt patentkrav 1, kännetecknat av att Na+-saltet av (-)-5-me- toxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfinyl]-lH-bensimidazol framställs. 10 5. Förfarande enligt patentkrav 1, kännetecknat av att den kirala acylgruppen i förfarande a) är mandeloyl.
6. Förfarande enligt patentkrav 1, kännetecknat av att diastereomerema i förfarande a) separeras genom kromatografi eller fraktionerad kristallisation.
7. Förfarande enligt patentkrav 1, kännetecknat av att solvolysen i förfarande a) 15 utförs i en basisk lösning innehällande en bas i ett protiskt lösningsmedel, säsom en eller flera alkoholer eller vatten, eller en bas i ett aprotiskt lösningsmedel, säsom dimetylsulfoxid eller dimetylformamid.
8. Förfarande enligt patentkrav 1, kännetecknat av att efter solvolysen i förfa- t rande a) neutraliseras produkten med ett neutraliserande reagens som kan vara en # 20 syra eller en ester, säsom metylformiat, foljt av behandling med en bas i en icke-]··*, vattenhaltig lösning för erhällande av det önskade optiskt rena saltet i kristallin form. • · · ♦ · ♦ ··# · • · · : 9. Förfarande enligt patentkrav 8 för framställning av natriumsaltet av (-)-5-me- toxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfinyl]-lH-bensimidazol i kris- : ·*; 25 tallin form, kännetecknat av att en ra natriumsaltprodukt erhälls efter solvolysen, • · · vilken produkt neutraliseras, följt av behandling med NaOH i ett icke-vattenhaltigt • ♦ * medium. ··· • - -
10. Förfarande enligt patentkrav 1, kännetecknat av att i förfarande a) erhälls natriumsaltet av (-)-5-metoxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfinyl]-30 lH-bensimidazol som ytterligare behandlas med en vattenlösning av ett oorganiskt * · **··* magnesiumsalt för erhällande av optiskt rent magnesiumsalt av (-)-5-metoxi-2-[[(4- metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfmyl]-lH-bensimidazol. 117755 (-)-5-metoxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfinyl]- ΙΗ-bensimi-dazol.
12. Förfarande enligt patentkrav 1, kännetecknat av att i forfarande b) behandlas (-)-5-metoxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfinyl]-lH-bensimi-5 dazol med en bas innehällande Na for erhällande av optiskt rent natriumsalt av .: (-)-5-metoxi-2-[[(4-metoxi-3,5-dimetyl-2-pyridinyl)metyl]sulfinyyl]-lH-bensimi-dazol. •t • » ·· ♦ · • ·· ·· · ♦ 1 1 « 1 * · ·♦· » · • · ··· . • 1 • 1 » « · « * « · ·#· • · · ··· • » · • · · ··· • « • · * « · ··· • · · • · · Ϊ • : ··· • · • · · · · ·♦· • · • · · • · *#·' * ♦ ♦
FI950377A 1993-05-28 1995-01-27 Förfarande för framställning av ett terapeutiskt aktivt, optiskt rent natrium- eller magnesiumsalt av pyridinylmetylsulfinyl-1H-bensimidazolförening FI117755B (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
SE19939301830A SE9301830D0 (sv) 1993-05-28 1993-05-28 New compounds
SE9301830 1993-05-28
PCT/SE1994/000509 WO1994027988A1 (en) 1993-05-28 1994-05-27 Optically pure salts of pyridinylmethyl sulfinyl-ih-benzimidazole compounds
SE9400509 1994-05-27

Publications (3)

Publication Number Publication Date
FI950377A0 FI950377A0 (sv) 1995-01-27
FI950377L FI950377L (sv) 1995-01-27
FI117755B true FI117755B (sv) 2007-02-15

Family

ID=20390088

Family Applications (2)

Application Number Title Priority Date Filing Date
FI950377A FI117755B (sv) 1993-05-28 1995-01-27 Förfarande för framställning av ett terapeutiskt aktivt, optiskt rent natrium- eller magnesiumsalt av pyridinylmetylsulfinyl-1H-bensimidazolförening
FI20070002A FI20070002L (sv) 1993-05-28 2007-01-02 Optiskt rena salter av pyridinylmetylsulfinyl-1H-bensimidazolföreningar

Family Applications After (1)

Application Number Title Priority Date Filing Date
FI20070002A FI20070002L (sv) 1993-05-28 2007-01-02 Optiskt rena salter av pyridinylmetylsulfinyl-1H-bensimidazolföreningar

Country Status (43)

Country Link
US (5) US5693818A (sv)
EP (3) EP0652872B1 (sv)
JP (3) JP3549111B2 (sv)
KR (1) KR100337274B1 (sv)
CN (2) CN1055469C (sv)
AT (1) ATE197452T1 (sv)
CA (2) CA2139653C (sv)
CL (1) CL2009000805A1 (sv)
CY (1) CY2224B1 (sv)
CZ (1) CZ287876B6 (sv)
DE (4) DE69426254T2 (sv)
DK (3) DK1020461T4 (sv)
DZ (1) DZ1785A1 (sv)
EE (1) EE03157B1 (sv)
ES (3) ES2099047T3 (sv)
FI (2) FI117755B (sv)
GR (2) GR970300012T1 (sv)
HK (3) HK1008330A1 (sv)
HR (1) HRP940307B1 (sv)
HU (1) HU226824B1 (sv)
IL (1) IL109684A (sv)
IS (1) IS1854B (sv)
LT (1) LT3287B (sv)
LU (1) LU91870I2 (sv)
LV (1) LV11034B (sv)
MA (1) MA23210A1 (sv)
MY (1) MY121192A (sv)
NO (2) NO307378B1 (sv)
NZ (1) NZ266915A (sv)
PL (1) PL178994B1 (sv)
PT (3) PT652872E (sv)
RU (1) RU2137766C1 (sv)
SA (2) SA94140756B1 (sv)
SE (1) SE9301830D0 (sv)
SG (1) SG49283A1 (sv)
SI (2) SI9420002B (sv)
SK (1) SK282524B6 (sv)
TN (1) TNSN94058A1 (sv)
TW (1) TW389761B (sv)
UA (1) UA60289C2 (sv)
WO (1) WO1994027988A1 (sv)
YU (1) YU49065B (sv)
ZA (1) ZA943557B (sv)

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