DK3053916T3 - Forbindelse med somatostatin-receptoragonistaktivitet og farmaceutisk anvendelse deraf - Google Patents

Forbindelse med somatostatin-receptoragonistaktivitet og farmaceutisk anvendelse deraf Download PDF

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DK3053916T3
DK3053916T3 DK14847684.9T DK14847684T DK3053916T3 DK 3053916 T3 DK3053916 T3 DK 3053916T3 DK 14847684 T DK14847684 T DK 14847684T DK 3053916 T3 DK3053916 T3 DK 3053916T3
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pyridinyl
dichlorophenyl
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phenyl
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Akiharu Ishida
Takeshi Matsushita
Tetsuya Sekiguchi
Yasuyuki Okabe
Tatsuya Komagata
Takuya Nishio
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Ono Pharmaceutical Co
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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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
    • A61P5/08—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH for decreasing, blocking or antagonising the activity of the anterior pituitary hormones
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

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Claims (13)

  1. FORBINDELSE MED SOMATOSTATIN-RECEPTORAGONISTAKTIVITET OG FARMACEUTISK ANVENDELSE DERAF
    1. Forbindelse repræsenteret ved den almene formel (I):
    hvor R1 repræsenterer (1) et halogenatom, (2) en cyanogruppe, (3) en Cl-4-alkyl, (4) en Cl-4-alkoxy eller (5) en C3-8-cycloalkyl, hvor Cl-4-alkylen, Cl-4-alkoxyen og C3-8-cycloalkylen kan være henholdsvis og uafhængigt substitueret med 1 til 3 halogenatomer og/eller cyanogrupper; p repræsenterer et heltal på 0 til 2; når p er 2, kan en flerhed af R1 være ens eller forskellige; R2 og R3 henholdsvis og uafhængigt repræsenterer et hydrogenatom eller en Cl-4-alkyl; R4 repræsenterer et hydrogenatom; eller R2 og R4 sammen med et atom, hvortil R2 og R4 er bundet, kan danne en 5- til 8-leddet nitrogenholdig mættet heterocyklus; L repræsenterer (1) en binding, (2) -CRA=CRB—> eller (3) -C(=O)-NRD—> (hvor i hver gruppe pilen indikerer stedet for binding til pyridinringen); RA, RB og RD henholdsvis og uafhængigt repræsenterer et hydrogenatom eller en Cl-4-alkyl; X1 og X2 henholdsvis og uafhængigt repræsenterer et halogenatom; et salt deraf, et N-oxid deraf eller et solvat deraf.
  2. 2. Forbindelse ifølge krav 1, repræsenteret ved den almene formel (1-1):
    hvor L1 repræsenterer (1) -CRA=CRB—> eller (2) -C(=O)-NRD—> (hvor i hver gruppe pilen indikerer stedet for binding til pyridinringen); og andre symboler har de samme betydninger som beskrevet i krav 1, et salt deraf, et N-oxid deraf eller et solvat deraf.
  3. 3. Forbindelse ifølge krav 1, repræsenteret ved den almene formel (1-4):
    hvor R24 repræsenterer et hydrogenatom eller en Cl-4-alkyl; og andre symboler har de samme betydninger som beskrevet i krav 1, et salt deraf, et N-oxid deraf eller et solvat deraf.
  4. 4. Forbindelse ifølge krav 1, der er valgt fra gruppen bestående af følgende forbindelser: (1) N-[4-(4-amino- l-piperidinyl)-5-(3-chlor-5-fhiorphenyl)-3-pyridinyl]-3-chlorbenzamid; (2) l-{3-(3-chlor-5-fluorphenyl)-5-[(E)-2-(3-chlorphenyl)vinyl]-4-pyridinyl}-4-piperidinamin; (3) 3-{(E)-2-[4-(4-amino-l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl] vinyl {benzonitril; (4) (4aS,8aS)-6-{3-(3,5-dichlorphenyl)-5-[(E)-2-(3-fluorphenyl)vinyl]-4-pyridinyl}octahydro-lH-pyrido[3,4-b][l,4]oxazin; (5) l-{3-(3,5-dichlorphenyl)-5-[(lE)-2-(3-fluorphenyl)-l-propen-l-yl]-4-pyridinyl}-4-piperidinamin; (6) 3-[(E)-2-{5-(3,5-dichlorphenyl)-4-[4-(ethylamino)-l-piperidinyl]-3-pyridinyl} vinyl] benzonitril; (7) l-{3-(3,5-dichlorphenyl)-5-[(lE)-2-(3-fluorphenyl)-l-propen-l-yl]-4-pyridinyl}-N-ethyl-4-piperidinamin; (8) 3-{(lE)-l-[4-(4-amino-l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl]-l-propen-2-yl}benzonitril; (9) 3-[(lE)-l-{5-(3,5-dichlorphenyl)-4-[4-(ethylamino)-l-piperidinyl]-3-pyridinyl}-l-propen-2-yl] benzonitril; (10) N-[4-(4-amino-l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl]-5-fluor-2-methoxybenzamid; (11) l-(4-{5-(3,5-dichlorphenyl)-4-[(4aS,8aS)-octahydro-6H-pyrido[3,4-b][l,4]oxazin-6-yl]-3-pyridinyl} phenyl)cyclopropancarbonitril; (12) l-{3-(3-chlor-5-fluorphenyl)-5-[4-(trifluormethyl)phenyl]-4-pyridinyl}-4-piperidinamin; (13) l-{3-(3,5-dichlorphenyl)-5-[4-(trifluormethyl)phenyl]-4-pyridinyl}-4-piperidinamin; (14) l-{3-(3-chlor-5-fluorphenyl)-5-[4-(difhiormethoxy)phenyl]-4-pyridinyl}-4-piperidinamin; (15) l-{4-[4-(4-amino-l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl] phenyl} cyclopropancarbonitril; (16) l-{3-(3,5-dichlorphenyl)-5-[4-(difluormethoxy)phenyl]-4-pyridinyl}-4-piperidinamin;
    (17) 1-(4-(5-(3,5-dichlorphenyl)-4-[4-(ethylamino)-l-piperidinyl]-3-pyridinyl} phenyl)cyclopropancarbonitril; (18) 2- (4-[4-(4-amino- l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl] phenyl }-2-methylpropannitril; (19) 2-(4- (5-(3,5-dichlorphenyl)-4-[4-(ethylamino)-l-piperidinyl]-3-pyTidinyl}phenyl)-2-methylpropannitril; (20) 1-( 3-(3,5-dichlorphenyl)-5-[4-(trifluormethyl)phenyl]-4-pyTidinyl}-N-ethyl-4-piperidinamin; og (21) 1-( 3-(3,5-dichlorphenyl)-5-[4-(difluormethoxy)phenyl]-4-pyridinyl}-N-ethyl-4-piperidinamin, et salt deraf, et N-oxid deraf eller et solvat deraf.
  5. 5. Forbindelse ifølge krav 2, der er valgt fra gruppen bestående af følgende forbindelser: (1) N-[4-(4-amino- l-piperidinyl)-5-(3-chlor-5-fluorphenyl)-3-pyridinyl]-3-chlorbenzamid; (2) l-(3-(3-chlor-5-fluorphenyl)-5-[(E)-2-(3-chlorphenyl)vinyl]-4-pyridinyl}-4-piperidinamin; (3) 3-{(E)-2-[4-(4-amino-l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl]vinyl(benzonitril; (4) (4aS,8aS)-6-{3-(3,5-dichlorphenyl)-5-[(E)-2-(3-fluorphenyl)vinyl]-4-pyridinyl}octahydro-lH-pyrido[3,4-b][l,4]oxazin; (5) l-{3-(3,5-dichlorphenyl)-5-[(lE)-2-(3-fluorphenyl)-l-propen-l-yl]-4-pyridinyI}-4-piperidinamin; (6) 3-[(E)-2-(5-(3,5-dichlorphenyl)-4-[4-(ethylamino)-l-piperidinyl]-3-pyridinyl} vinyl] benzonitril; (7) l-{3-(3,5-dichlorphenyl)-5-[(lE)-2-(3-fluorphenyl)-l-propen-l-yl]-4-pyridinyl}-N-ethyl-4-piperidinamin; (8) 3-{(IE)-1-(4-(4- amino- l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl]-l-propen-2-yl}benzonitril; (9) 3-[(lE)-l-{5-(3,5-dichlorphenyl)-4-[4-(ethylamino)-l-piperidinyl]-3-pyridinyl}-l-propen-2-yl] benzonitril og (10) N-[4-(4-amino-l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl]-5-fluor-2-methoxybenzamid, et salt deraf, et N-oxid deraf eller et solvat deraf.
  6. 6. Forbindelse ifølge krav 3, der er valgt fra gruppen bestående af følgende forbindelser: (1) l-{3-(3-chlor-5-fluorphenyl)-5-[4-(trifluormethyl)phenyl]-4-pyridinyl}-4-piperidinamin; (2) l-{3-(3,5-dichlorphenyl)-5-[4-(trifluormethyl)phenyl]-4-pyridinyl}-4-piperidinamin; (3) l-{3-(3-chlor-5-fluorphenyl)-5-[4-(difluormethoxy)phenyl]-4-pyridinyl}-4-piperidinamin; (4) l-(4-[4-(4-amino-l-piperidinyl)-5-(3,5-dichlorphenyl)-3-pyridinyl] phenyl} cyclopropancarbonitril; (5) l-{3-(3,5-dichlorphenyl)-5-[4-(difluormethoxy)phenyl]-4-pyridinyl}-4-piperidinamin; (6) 1-(4-(5-(3,5-dichlorphenyl)-4-[4-(ethylamino)-l-piperidinyl]-3-pyridinyl} phenyl)cyclopropancarbonitril; (7) 2-{4-[4-(4-amino-1-piperi din yl)-5-(3,5-dichlorphenyl)-3-pyridinyl] phenyl }-2-methylpropannitril; (8) 2-(4-{5-(3,5-dichlorphenyl)-4-[4-(ethylamino)-l-piperidinyl]-3-pyridinyl}phenyl)-2-methylpropannitril; (9) l-{3-(3,5-dichlorphenyl)-5-[4-(trifluormethyl)phenyl]-4-pyridinyl}-N-ethyl-4-piperidinamin; og (10) l-{3-(3,5-dichlorphenyl)-5-[4-(difluormethoxy)phenyl]-4-pyridinyl}-N-ethyl-4-piperidinamin, et salt deraf, et N-oxid deraf eller et solvat deraf eller en af ovenstående.
  7. 7. Farmaceutisk sammensætning, der omfatter forbindelsen ifølge krav 1, et salt deraf, et N-oxid deraf eller et solvat deraf, eller en af ovenstående og en farmaceutisk acceptabel bærer.
  8. 8. Farmaceutisk sammensætning ifølge krav 7, der er et profylaktisk og/eller terapeutisk middel mod en somatostatin-relateret sygdom.
  9. 9. Farmaceutisk sammensætning ifølge krav 8, hvor den somatostatin-relaterede sygdom er akromegali eller et gastrointestinalt symptom, der ledsager gastrointestinal obstruktion.
  10. 10. Lægemiddel, der omfatter forbindelsen ifølge krav 1, et salt deraf, et N-oxid deraf eller et solvat deraf i kombination med mindst ét lægemiddel valgt fra gruppen bestående af pegvisomant, bromocriptin og cabergolin.
  11. 11. Lægemiddel, der omfatter forbindelsen ifølge krav 1, et salt deraf, et N-oxid deraf eller et sol vat deraf i kombination med mindst ét lægemiddel valgt fra gruppen bestående af prochlorperazin, levomepromazin, risperidon, metoclopramid, domperidon, diphenhydramin, chlorpheniramin, dimenhydrinat, promethazin, diprophyllin, famotidin, cimetidin, scopolamin, tropisetron, granisetron, ondansetron, azasetron, ramosetron, indisetron, palonosetron, cisaprid, mosaprid, dexamethason, betamethason, prednisolon, olanzapin, quetiapin, perospiron, methylnaltrexon og morphin.
  12. 12. Forbindelse ifølge krav 1 til anvendelse i en fremgangsmåde til profylakse af og/eller terapi ved en somatostatin-relateret sygdom, hvilken fremgangsmåde omfatter administration til et pattedyr af en virksom mængde af forbindelsen, et salt deraf, et N-oxid deraf eller et solvat deraf.
  13. 13. Forbindelse ifølge krav 1, et salt deraf, et N-oxid deraf eller et solvat deraf til anvendelse i en fremgangsmåde til profylakse af og/eller terapi ved en somatostatin-relateret sygdom.
DK14847684.9T 2013-09-30 2014-09-29 Forbindelse med somatostatin-receptoragonistaktivitet og farmaceutisk anvendelse deraf DK3053916T3 (da)

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PCT/JP2014/075794 WO2015046482A1 (ja) 2013-09-30 2014-09-29 ソマトスタチン受容体作動活性を有する化合物およびその医薬用途

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EP3053916A4 (en) 2017-03-08
AU2014325078B2 (en) 2018-10-25
CN105593221B (zh) 2017-09-22
JP6380402B2 (ja) 2018-08-29
HK1223356A1 (zh) 2017-07-28
CA2925651A1 (en) 2015-04-02
US9643951B2 (en) 2017-05-09
TW201602092A (zh) 2016-01-16
PT3053916T (pt) 2019-03-26
SG11201602477YA (en) 2016-05-30
RU2016111659A3 (da) 2018-03-20
HUE043374T2 (hu) 2019-08-28
EP3053916B1 (en) 2019-01-30
ES2716151T3 (es) 2019-06-10
KR20160062023A (ko) 2016-06-01
MX2016004088A (es) 2016-06-06
US20160311794A1 (en) 2016-10-27
PH12016500573B1 (en) 2016-07-04
PH12016500573A1 (en) 2016-07-04
IL244813A0 (en) 2016-05-31
BR112016007078A2 (pt) 2017-12-12
TWI628175B (zh) 2018-07-01
CN105593221A (zh) 2016-05-18
RU2016111659A (ru) 2017-11-13
WO2015046482A1 (ja) 2015-04-02
AU2014325078A1 (en) 2016-04-21

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