DK2805940T3 - Pyrazincarboxamidforbindelse - Google Patents

Pyrazincarboxamidforbindelse Download PDF

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Publication number
DK2805940T3
DK2805940T3 DK13738947.4T DK13738947T DK2805940T3 DK 2805940 T3 DK2805940 T3 DK 2805940T3 DK 13738947 T DK13738947 T DK 13738947T DK 2805940 T3 DK2805940 T3 DK 2805940T3
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amino
carboxamide
phenyl
pyrazine
methylpiperazin
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DK13738947.4T
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Takahiro Matsuya
Yutaka Kondoh
Itsuro Shimada
Shigetoshi Kikuchi
Maiko Iida
Kenichi Onda
Hiroki Fukudome
Yukihiro Takemoto
Nobuaki Shindou
Hideki Sakagami
Hisao Hamaguchi
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Astellas Pharma Inc
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
    • 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
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
    • C07D241/28—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms in which said hetero-bound carbon atoms have double bonds to oxygen, sulfur or nitrogen atoms
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    • 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
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    • 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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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

Claims (13)

1. Forbindelse med formlen (I) eller et salt deraf: [Chcm. 16]
(hvor R1 betegner piperazinyl der er substitueret med Ci-6 alkyl, piperidinyl der er substitueret med Ci-e alkyl, eller piperidyl substitueret med piperazinyl der kan være substitueret med Ci-6 alkyl, Ring A betegner benzen der kan være substitueret med én eller flere substituenter valgt fra gruppen bestående af halogen, Ci-e alkyl der kan være substitueret med ét eller flere halogenatomer, og -O-Ci-6 alkyl, pyrazol der kan være substitueret med Ci-6 alkyl, imidazol der kan være substitueret med Ci-6 alkyl eller pyrimidin der kan være substitueret med Ci-6 alkyl, L1 betegner NH-, R2 betegner H eller Ci-e alkyl, L2 betegner -O- eller en binding, Y betegner Ring X, Ring X betegner en aromatisk heterocykel, en ikke-aromatisk heterocykel, cycloalkan, eller benzen der kan være substitueret med én eller flere substituenter valgt fra gruppen bestående af halogen, -O- Ci-e alkyl, -CN, cycloalkyl, aryl, aromatisk heterocyklisk gruppe, ikke-aromatisk heterocyklisk gruppe der kan være substitueret med Ci-e alkyl, oxo, og Ci-6 alkyl der kan være substitueret med ét eller flere halogenatomer, L3 betegner -NH-, -N(Ci-e alkyl)- eller en binding, M betegner -C(0), R3 betegner H, R4 betegner H.)
2. Forbindelsen eller et salt deraf ifølge krav 1, hvor L2 er -O-, Ring X er benzen der kan være substitueret med Ci-e alkyl, og L3 er -NH-.
3. Forbindelsen eller et salt deraf ifølge krav 1, hvor L2 er -O-, Ring X er en ikke-aromatisk heterocykel, og L3 er en binding.
4. Forbindelsen eller et salt deraf ifølge krav 1, hvor L2 er en binding, Ring X er en ikke-aromatisk heterocykel, og L3 er en binding.
5. Forbindelsen eller et salt deraf ifølge krav 3, hvor Ring X er pyrrolidin eller piperidin.
6. Forbindelsen eller et salt deraf ifølge krav 4, hvor Ring X er piperidin eller tetrahydropyridin.
7. Forbindelsen eller et salt deraf ifølge krav 1, som er 5-[3-(acryloylamino)phenoxy]-6-ethyl-3-{[4-(4-methylpiperazin-l- yl)phenyl]amino}pyrazin-2-carboxamid, 5-[3-(acryloylamino)-2-methylphenoxy]-6-ethyl-3-{[4-(4-methylpiperazin- l-yl)phenyl]amino}pyrazin-2-carboxamid, 5-[3-(acryloylamino)phenoxy]-6-isopropyl-3-{[4-(4-methylpiperazin-l- yl)phenyl]amino}pyrazin-2-carboxamid, 5-(l-acryloylpiperidin-4-yl)-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin- l-yl)piperidin-l-yl]phenyl}amino)pyrazin-2-carboxamid, 5-[3-(acryloylamino)phenoxy]-3-{[4-(4-methylpiperazin-l- yl)phenyl]amino}pyrazin-2-carboxamid, 5-[3-(acryloylamino)phenoxy]-6-ethyl-3-{[4-methoxy-3-(4- methylpiperazin-l-yl)phenyl]amino}pyrazin-2-carboxamid, 5-[3-(acryloylamino)phenoxy]-6-ethyl-3-{[4-(4-ethylpiperazin-l- yl)phenyl]amino}pyrazin-2-carboxamid, 5-{[(3R)-l-acryloylpyrrolidin-3-yl]oxy}-6-ethyl-3-({4-[4-(4- methylpiperazin-l-yl)piperidin-l-yl]phenyl}amino)pyrazin-2-carboxamid, 5-[3-(acryloylamino)phenoxy]-6-isopropyl-3-{[l-(l-rnethylpiperidin-4-yl)- lH-pyrazol-4-yl]amino}pyrazin-2-carboxamid, 5-[3-(acryloylamino)phenoxy]-3-({4-[(3S)-3,4-dimethylpiperazin-l- yl]phenyl>amino)-6-ethylpyrazin-2-carboxamid, 5-[3-(acryloylamino)phenoxy]-3-({4-[(3R)-3,4-dimethylpiperazin-l- yl]phenyl}amino)-6-ethylpyrazin-2-carboxamid, 5-(l-acryloylpiperidin-4-yl)-6-ethyl-3-({4-[4-(4-methylpiperazin-l- yl)piperidin-l-yl]phenyl}amino)pyrazin-2-carboxamid, 5-{[(3R)-l-acryloylpyrrolidin-3-yl]oxy>-6-ethyl-3--C[4-(4-methylpiperazin- l-yl)phenyl]amino}pyrazin-2-carboxamid, 5-{[(3R)-l-acryloylpiperidin-3-yl]oxy>-6-ethyl-3-({4-[4-(4- methylpiperazin-l-yl)piperidin-l-yl]phenyl}amino)pyrazin-2-carboxamid, 5-{[(3R)-l-acryloylpiperidin-3-yl]oxy}-6-ethyl-3-({3-methyl-4-[4-(4- methylpiperazin-l-yl)piperidin-l-yl]phenyl}amino)pyrazin-2-carboxamid, eller 5-[5-(acryloylamino)-2-fluorophenoxy]-6-ethyl-3-{[4-(4-methylpiperazin-l-yl)phenyl]amino}pyrazin-2-carboxamid, eller et salt deraf.
8. Farmaceutisk sammensætning omfattende forbindelsen eller et salt deraf ifølge krav 7, og en farmaceutisk acceptabel excipiens.
9. Anvendelse af forbindelsen eller et salt deraf ifølge krav 7, til fremstillingen af en farmaceutisk sammensætning til forebyggelse og/eller behandling af EGFR T790M mutation positiv cancer.
10. Forbindelsen eller et salt deraf ifølge krav 7 til anvendelse i behandlingen af EGFRT790M mutation positiv cancer.
11. Forbindelsen eller et salt deraf ifølge krav 7, som er 5-[3-(acryloyl-amino)phenoxy]-6-isopropyl-3-{[4-(4-methylpiperazin-l-yl)phenyl]amino}-pyrazin-2-carboxamid eller et salt deraf.
12. Forbindelsen eller et salt deraf ifølge krav 7, som er 5-(l-acryloylpiperidin-4-yl)-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-l-yl)piperidin-l-yl]phenyl}amino)pyrazin-2-carboxamid eller et salt deraf.
13. Forbindelsen eller et salt deraf ifølge krav 7, som er 5-{[(3R)-l-acryloyl-pyrrolidin-3-yl]oxy}-6-ethyl-3-({4-[4-(4-methylpiperazin-l-yl)piperidin-l-yl]phenyl}amino)pyrazin-2-carboxamid eller et salt deraf.
DK13738947.4T 2012-01-17 2013-01-15 Pyrazincarboxamidforbindelse DK2805940T3 (da)

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JP2012007525 2012-01-17
PCT/JP2013/050579 WO2013108754A1 (ja) 2012-01-17 2013-01-15 ピラジンカルボキサミド化合物

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KR (1) KR101985050B1 (da)
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