HRP20120833T1 - Derivati benzilpiperazina, korisni u lijeäśenju gastrointestinalnih poremeä†aja - Google Patents

Derivati benzilpiperazina, korisni u lijeäśenju gastrointestinalnih poremeä†aja Download PDF

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HRP20120833T1
HRP20120833T1 HRP20120833TT HRP20120833T HRP20120833T1 HR P20120833 T1 HRP20120833 T1 HR P20120833T1 HR P20120833T T HRP20120833T T HR P20120833TT HR P20120833 T HRP20120833 T HR P20120833T HR P20120833 T1 HRP20120833 T1 HR P20120833T1
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methyl
phenyl
piperazinyl
piperidinamine
fluorophenyl
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HRP20120833TT
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Christopher Norbert Johnson
David Timothy Macpherson
Steven James Stanway
Geoffrey Stemp
Mervyn Thompson
Susan Marie Westaway
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Glaxo Group Limited
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Priority claimed from GB0515381A external-priority patent/GB0515381D0/en
Priority claimed from GB0611469A external-priority patent/GB0611469D0/en
Application filed by Glaxo Group Limited filed Critical Glaxo Group Limited
Publication of HRP20120833T1 publication Critical patent/HRP20120833T1/hr

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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
    • C07D401/10—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 carbon chain containing aromatic rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A61P1/10—Laxatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
    • 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
    • C07D401/14—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 three or more hetero rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Diabetes (AREA)
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  • Hospice & Palliative Care (AREA)
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  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (14)

1. Spoj formule (I), ili njegova farmaceutski prihvatljiva sol: [image] naznačen time što: A je fenil ili 6-eročlani heteroarilni prsten, izborno supstituiran s halogenom, C(1-4) alkilom ili C(1-4) alkoksi; R1 i R2 su neovisno H ili C(1-4) alkil; R3 je fenil ili je izborno supstituiran s jednim do dva supstituenta koje se bira između fluora, cijano, trifluormetila i metoksi; X je (CR4R5)n; n je 1 ili 2; Y je NH, O ili CH2; R4 i R5 se neovisno bira između vodika i C(1-4) alkila.
2. Spoj formule (I) ili njegova farmaceutski prihvatljiva sol, naznačen time što: A je fenil ili piridil; R1 je vodik ili metil; R2 je vodik ili metil; R3 je izborno supstituirani fenil; Y je NH ili O; X je (CR4R5)n; n je 1 ili 2; i R4 i R5 su neovisno vodik ili metil.
3. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 2, naznačen time što (piperazinil)metilenski supstituent i X su međusobno u para-položaju na prstenu A.
4. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što R1 i R2 nisu vodici, a piperazinski ugljici C* imaju konfiguraciju 3R,5S.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira između: 1-[(4-{[(3R,5S)-3,5-dimetil-1-piperazinil]metil}fenil)acetil]-N-(4-fluorfenil)-4-piperidinamina N-(4-fluorfenil)-1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinamina 3-({1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinil}amino)benzonitrila 4-({1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinil}amino)benzonitrila N-(3,4-difluorfenil)-1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinamina N-[4-fluor-3-(metiloksi)fenil]-1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinamina (3S)-1-{[4-(2-{4-[(4-fluorfenil)oksi]-1-piperidinil}-2-oksoetil)fenil]metil}-3-metilpiperazina (3S)-1-{[4-(2-{4-[(3-fluorfenil)oksi]-1-piperidinil}-2-oksoetil)fenil]metil}-3-metilpiperazina 1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-N-[3-(trifluormetil)fenil]-4-piperidinamina 1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-N-[4-(trifluormetil)fenil]-4-piperidinamina N-(3-fluorfenil)-1-{[4-(1-piperazinilmetil)fenil]acetil}-4-piperidinamina N-(3-fluorfenil)-1-[(4-{[(3R)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinamina N-(3,4-difluorfenil)-1-[(4-{[(3R)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinamina (3R)-1-{[4-(2-{4-[(4-fluorfenil)oksi]-1-piperidinil}-2-oksoetil)fenil]metil}-3-metilpiperazina (3R)-1-{[4-(2-{4-[(3-fluorfenil)oksi]-1-piperidinil}-2-oksoetil)fenil]metil}-3-metilpiperazina 4-({1-[(4-{[(3R)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinil}oksi)benzonitrila 4-({1-[(4-{[(3R)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinil}amino)benzonitrila 3-({1-[(4-{[(3R)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinil}amino)benzonitrila 1-[(4-{[(3R)-3-metil-1-piperazinil]metil}fenil)acetil]-N-[3-(trifluormetil)fenil]-4-piperidinamina N-(3-fluorfenil)-1-[(3-(metiloksi)-4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinamina 2-fluor-5-({1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinil}amino)benzonitrila 1-[3-(4-{[(3R,5S)-3,5-dimetil-1-piperazinil]metil}fenil)propanoil]-N-(4-fluorfenil)-4-piperidinamina 1-[3-(4-{[(3R,5S)-3,5-dimetil-1-piperazinil]metil}fenil)propanoil]-N-(3-fluorfenil)-4-piperidinamina N-(4-fluorfenil)-1-[3-(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)propanoil]-4-piperidinamina N-(3-fluorfenil)-1-[3-(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)propanoil]-4-piperidinamina 1-[2-(4-{[(3R,5S)-3,5-dimetil-1-piperazinil]metil}fenil)propanoil]-N-(4-fluorfenil)-4-piperidinamina 1-[2-(4-{[(3R,5S)-3,5-dimetil-1-piperazinil]metil}fenil)propanoil]-N-(3-fluorfenil)-4-piperidinamina 1-[2-(4-{[(3R,5S)-3,5-dimetil-1-piperazinil]metil}fenil)-2-metilpropanoil]-N-(4-fluorfenil)-4-piperidinamina 1-[2-(4-{[(3R,5S)-3,5-dimetil-1-piperazinil]metil}fenil)-2-metilpropanoil]-N-(3-fluorfenil)-4-piperidinamina (3R,5S)-1-{[4-(2-{4-[(4-fluorfenil)oksi]-1-piperidinil}-1,1-dimetil-2-oksoetil)fenil]metil}-3,5-dimetilpiperazina N-(3-fluorfenil)-1-[3-(5-{[(3S)-3-metil-1-piperazinil]metil}-2-piridinil)propanoil]-4-piperidinamina 1-[(3-klor-4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-N-(3-fluorfenil)-4-piperidinamina N-(2-fluorfenil)-1-[(4-{[(3R)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinamina N-(3-fluorfenil)-1-[(5-{[(3S)-3-metil-1-piperazinil]metil}-2-piridinil)acetil]-4-piperidinamina 2-({1-[(4-{[(3R)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinil}amino)benzonitrila 2-fluor-4-({1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinil}amino)benzonitril-hidroklorida.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je N-(3-fluorfenil)-1-[(4-{[(3S)-3-metil-1-piperazinil]metil}fenil)acetil]-4-piperidinamin.
7. Upotreba spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 6 u proizvodnji medikamenta namijenjenog upotrebi in the liječenje stanja ili poremećaja povezanih s receptorima GPR38, naznačena time što stanja ili poremećaji su poremećaji gastroesofagealnog refluksa, funkcionalna dispepsija, sindrom iritabilnih crijeva, konstipacija, pseudoopstrukcija crijeva, paralitički ileus nakon kirurškog zahvata ili koje druge manipulacije, povraćanje, želučana staza ili hipomotilitet kojeg uzrokuju različite bolesti, poput dijabetesa i/ili primjena drugih lijekova, Crohnova bolest, kolitis, kaheksija povezana s uznapredovalim bolestima, poput raka i/ili njegovog liječenja, kaheksija povezana s apetitom/metabolizmom, te drugi poremećaji, poput inkontinencije.
8. Postupak dobivanja spoja, ili njegove farmaceutski prihvatljive soli, u skladu s bilo kojim od patentnih zahtjeva 1 do 6 kada A je fenil, a X je CH2, naznačen time što se sastoji u a) reakciji spoja formule (II) [image] , gdje su R1 i R3 definirani kao za formulu (I), a Q je vodik ili pogodna zaštitna skupina za dušik, sa spojem formule (III) [image] , gdje su Y i R3 definirani kao za formulu (I), u reakcijskim uvjetima pogodnim za reduktivno alkiliranje, u pogodnom otapalu; i b) nakon toga izbornom provođenju jedne ili više naknadnih reakcija: 1) prevođenja jednog spoja formule (I) u drugi spoj formule (I); 2) uklanjanja svih zaštitnih skupina; 3) dobivanja pogodne farmaceutski prihvatljive soli ili solvata tako dobivenog spoja.
9. Postupak dobivanja spoja formule (III), naznačen time što se navedeni postupak sastoji u reakciji spoja formule (IV) [image] , gdje su R3 i Y definirani kao za formulu (I) u patentnom zahtjevu 1, sa spojem formule (V) [image] , u prisutnosti pogodnog kondenzacijskog reagensa.
10. Postupak dobivanja spoja, ili njegove farmaceutski prihvatljive soli, u skladu s bilo kojim od patentnih zahtjeva 1 do 6 kada A je fenil, a X je CH2, naznačen time što se sastoji u a) reakciji spoja formule (VI), [image] , gdje su R1 i R2 definirani kao za formulu (I), a Q je vodik ili pogodna zaštitna skupina za dušik, sa spojem formule (IV) u prisutnosti pogodnog kondenzacijskog reagensa, u pogodnom otapalu; i b) nakon toga izbornom provođenju jedne ili više naknadnih reakcija: 1) prevođenja jednog spoja formule (I) u drugi spoj formule (I); 2) uklanjanja svih zaštitnih skupina; ili 3) dobivanja pogodne farmaceutski prihvatljive soli ili solvata tako dobivenog spoja.
11. Postupak dobivanja spoja formule (VI), naznačen time što se sastoji u hidrolizi i dekarboksiliranju spoja formule (VII) [image] , gdje su R1, R3 i Q definirani kao u patentnom zahtjevu 12, a P je pogodna alkilna skupina.
12. Spoj formule (III), (VI) ili (VII), naznačen time što su R1, R2, R3 i Y definirani kao za formulu (I) u patentnom zahtjevu 1, Q je vodik ili pogodna zaštitna skupina za dušik, a P je pogodna alkilna skupina [image] [image] [image] .
13. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6.
14. Postupak priprave farmaceutskog pripravka, naznačen time što se pripravlja farmaceutski pripravak u skladu s patentnim zahtjevom 13.
HRP20120833TT 2005-07-26 2012-10-15 Derivati benzilpiperazina, korisni u lijeäśenju gastrointestinalnih poremeä†aja HRP20120833T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0515381A GB0515381D0 (en) 2005-07-26 2005-07-26 Compounds
GB0611469A GB0611469D0 (en) 2006-06-09 2006-06-09 Compounds
PCT/EP2006/007390 WO2007012479A2 (en) 2005-07-26 2006-07-24 Benzylpiperazine derivates and their medical use

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HRP20120833T1 true HRP20120833T1 (hr) 2012-11-30

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