HRP20160096T1 - Supstituirani derivati izokinolina - Google Patents

Supstituirani derivati izokinolina Download PDF

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HRP20160096T1
HRP20160096T1 HRP20160096TT HRP20160096T HRP20160096T1 HR P20160096 T1 HRP20160096 T1 HR P20160096T1 HR P20160096T T HRP20160096T T HR P20160096TT HR P20160096 T HRP20160096 T HR P20160096T HR P20160096 T1 HRP20160096 T1 HR P20160096T1
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isoquinoline
ylsulfonyl
methyl
diazepan
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HRP20160096TT
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Hiroyushi Hidaka
Kouichi Takahashi
Yoshihiro Inoue
Kengo Sumi
Ryohei Nakamura
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D. Western Therapeutics Institute, Inc.
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    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic 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
    • A61K31/535—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
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • 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
    • 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

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Claims (9)

1. Derivat izokinolin-6-sulfonamida predstavljen Formulom (1), njegova sol ili solvat derivata ili soli: [image] naznačen time, da X i Y su svaki neovisno predstavljeni direktnom vezom, NH, CH=CH, O ili S; R1 i R2 svaki neovisno predstavljaju atom vodika, atom halogena, cijano skupinu, alkilnu skupinu, halogenoalkilnu skupinu, alkenilnu skupinu, alkoksi skupinu, alkiltio skupinu, hidroksilnu skupinu, merkapto skupinu, nitro skupinu, arilnu skupinu, amino skupinu ili aminoalkiltio skupinu; R3 i R4 svaki neovisno predstavljaju atom vodika, alkilnu skupinu, alkenilnu skupinu, amino skupinu, alkilamino skupinu, dialkilamino skupinu, aminoalkulnu skupinu, halogenoalkilnu skupinu, alkanoilnu skupinu, aminoalkanoilnu skupinu, alkilaminoalkanoilnu skupinu, alkoksikarbonilnu skupinu, hidroksilnu skupinu ili merkapto skupinu ili R3 i R4 zajedno tvore alkilensku skupinu ili alkenilensku skupinu, koja može biti premoštena između dva ugljikova atoma na proizvoljnom položaju; a 1, m i n predstavljaju cijeli broj od 1 do 4.
2. Derivat izokinolin-6-sulfonamida u skladu s patentnim zahtjevom 1, njegova sol ili solvat derivata ili soli, naznačen time, da u Formuli (1), X i Y su svaki neovisno direktna veza, NH, CH=CH, O ili S; R1 i R2su svaki neovisno atom vodika, atom halogena, cijano skupina, C1-8 alkilna skupina, halogeno C1-8 alkilna skupina, C2-8 alkenilna skupina, C1-8 alkoksi skupina, C1-8 alkiltio skupina, hidroksilna skupina, merkapto skupina, nitro skupina, fenilna skupina, amino skupina ili amino C1-8 alkiltio skupina; R3 i R4 su svaka neovisno atom vodika, C1-8 alkilna skupina, C2-8 alkenilna skupina, amino skupina, amino C1-8 alkilna skupina, halogeno C1-8 alkilna skupina, C1-8 alkilamino skupina, di-C1-8 alkilamino skupina, C2-8 alkanoilna skupina, amino C2-8 alkanoilna skupina, C1-8 alkoksikarbonilna skupina, hidroksilna skupina ili merkapto skupina ili R3 i R4 zajedno tvore premoštenu C1-3 alkilensku skupinu ili alkenilensku skupinu; 1 i m su svaki neovisno 1 do 3; a n je 2 ili 3.
3. Derivat izokinolin-6-sulfonamida u skladu s patentnim zahtjevom 1 ili 2, njegova sol ili solvat derivata ili soli, naznačen time, da u Formuli (1), X je direktna veza ili NH; Y je direktna veza, NH, CH=CH ili O; R1 i R2 su svaki neovisno atom vodika, atom halogena, C1-8 alkilna skupina, nitro skupina, cijano skupina, hidroksilna skupina, halogeno C1-8 alkilna skupina, fenilna skupina ili amino C1-8 alkiltio skupina; R3 i R4 su atom vodika, C1-8 alkilna skupina, amino skupina, C1-8 alkilamino skupina, amino C1-8 alkilna skupina, halogeno C1-8 alkilna skupina, amino C1-8 alkanoilna skupina, C1-8 alkilamino skupina ili C1-8 alkanoilna skupina ili R3 i R4 zajedno tvore premoštenu C1-3 alkilensku skupinu; 1 i m su svaki neovisno 1 do 3; i n je 2 ili 3.
4. Derivat izokinolin-6-sulfonamida u skladu s bilo kojim patentnim zahtjevom 1 do 3, njegova sol ili solvat derivata ili soli, naznačen time, da u Formuli (1), X je direktna veza ili NH; Y je direktna veza, NH, CH=CH ili O; R1 i R2 su svaki neovisno atom vodika, atom halogena, nitro skupina, aminoalkiltio skupina, C1-6 alkilna skupina ili halogeno C1-6 alkilna skupina; R3 i R4 su atom vodika, C1-6 alkilna skupina, halogeno C1-6 alkilna skupina, amino skupina, C1-8 alkilamino skupina ili amino C1-8 alkanoilna skupina ili R3 i R4 zajedno tvore premoštenu C1-3 alkilensku skupinu; 1 i m su svaki neovisno 1 do 3; i n je 2 ili 3.
5. Derivat izokinolin-6-sulfonamida u skladu s bilo kojim patentnim zahtjevom 1 do 4, njegova sol ili solvat derivata ili soli, naznačen time, da u Formuli (1), X je direktna veza ili NH; Y je direktna veza, CH=CH ili O; R1 i R2 su svaki neovisno atom vodika, atom halogena, aminoalkiltio skupina ili C1-6 alkilna skupina; R3 i R4 su atom vodika, C1-6 alkilna skupina, halogeno C1-6 alkilna skupina ili amino skupina ili R3 i R4 zajedno tvore premoštenu C1-3 alkilensku skupinu; 1 i m su svaki neovisno 1 do 3; i n je 2 ili 3.
6. Spoj odabran iz skupine koja se sastoji od sljedećeg, njihovih soli ili njihovih solvata: 6-(piperazin-1-ilsulfonil)izokinolina, (R)-6-(3-aminopirolidin-1-ilsulfonil)izokinolina, 6-(1,4-diazepan-1-ilsulfonil)izokinolina, 6-(4-aminopiperidin-1-ilsulfonil)izokinolina, 5-brom-6-(1,4-diazepan-1-ilsulfonil)izokinolina, 6-(1,4-diazepan-1-ilsulfonil)-8-fluoroizokinolina, 6-{(1S,4S)-2,5-diazabiciklo[2.2.1]heptan-2-ilsulfonil}izokinolina, (R,Z)-6-(2-metil-2,3,4,5-tetrahidro-1,4-diazocin-1(8H)-ilsulfonil)izokinolina, 6-(morfolin-1 -ilsulfonil)izokinolina, (S)-6-{3-(N-metilamino)pirolidin-1-ilsulfonil}izokinolina, (S)-6-{3-(N-butilamino)pirolidin-1-ilsulfonil}izokinolina, (S)-6-(2-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (S)-6-(2-metilpiperazin-1-ilsulfonil)izokinolina, (R)-6-(2-metil-1,4-diazocan-1-ilsulfonil)izokinolina, (S)-5-brom-6-(2-metil-1,4-diazepan-1-ilsulfonil)izokinolina, 6-(3-metil- 1,4-diazepan-1-ilsulfonil)izokinolina, 6-(7-metil- 1,4-diazepan-1-ilsulfonil)izokinolina, (R)-6-(2-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-6-(2-etil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-6-(2-etil-1,4-diazocan-1-ilsulfonil)izokinolina, 6-(1,4-diazocan-1-ilsulfonil)izokinolina, 6-(2,2-dimetil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-5-bromo-6-(2-metil-1,4-diazocan-1-ilsulfonil)izokinolina, (S)-6-(2-metil-1,4-diazocan-1-ilsulfonil)izokinolina, (R)-6-(2-metil-1,4-diazepan-1-ilsulfonil)-7-fluoroizokinolina, (S)-6-(2-fluorometil-1,4-diazepan-1-ilsulfonil)izokinolina, (S)-6-(2-fluorometil-1,4-diazocan-1-ilsulfonil)izokinolina, (S)-6-(2-metil-1,4-diazonan-1-ilsulfonil)izokinolina, (R)-5-bromo-6-(2-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-6-(6-metil-1,4-diazocan-1-ilsulfonil)izokinolina, (R)-6-(7-metil-1,4-diazocan-1-ilsulfonil)izokinolina, (S)-6-(7-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-6-(2-metil-1,4-diazonan-1-ilsulfonil)izokinolina, (R)-6-(7-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (2R,7R)-6-(2,7-dimetil-1,4-diazepan-1-ilsulfonil)izokinolina, (2S,7R)-6-(2,7-dimetil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-6-(8-metil-1,4-diazocan-1-ilsulfonil)izokinolina, (R)-6-(2-metil-1,5-diazocan-1-ilsulfonil)izokinolina, (R)-6-(2-metil-1,4-diazocan-1-ilsulfonil)-5-nitroizokinolina, (2R,6R)-6-(2,6-dimetilpiperazin-1-ilsulfonil)izokinolina, (2S,7S)-6-(2,7-dimetil-1,4-diazepan-1-ilsulfonil)izokinolina, (S)-6-(2-metil-1,5-diazocan-1-ilsulfonil)izokinolina, (R)-6-(5 -metil-1,4,7-oksadiazonan-4-ilsulfonil)izokinolina, (R)-6-(2-metil-1,4,7-triazonan-1-ilsulfonil)izokinolina, 6-(4-glicil-1,4-diazepan-1-ilsulfonil)izokinolina, (S)-6-(4-glicil-2-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-6-(4-glicil-2-metil-1,4-diazocan-1-ilsulfonil)izokinolina, (R)-6-(4-sarkosil-2-metil-1,4-diazocan-1-ilsulfonil)izokinolina, (S)-5-metil-6-(2-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (S)-1-(2-aminoetiltio)-6-(2-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-1-(2-aminoetiltio)-6-(7-metil-1,4-diazepan-1-ilsulfonil)izokinolina, (R)-1-(2-aminoetiltio)-6-(2-metil-1,4-diazocan-1-ilsulfonil)izokinolina, 6-(1,4-diazepan-1 -ilsulfonil)izokinolin-1(2H)-ona, 1-amino-6-(1,4-diazepan-1-ilsulfonil)izokinolina, 1-nitrile-6-(1,4-diazepan-1-ilsulfonil)izokinolina, (S)-6-(2-(4-aminobutyl)-1,4-diazepin-1-ilsulfonil)izokinolina, 6-(4-metoksikarbonilpiperidin-1-ilsulfonil)izokinolina, (S)-6-(3-hidroksipirolidin-1-ilsulfonil)izokinolina, i 5-fenil-6-(1,4-diazepan-1-ilsulfonil)izokinolina.
7. Farmaceutski pripravak, naznačen time, da sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6.
8. Farmaceutski pripravak u skladu s patentnim zahtjevom 7, naznačen time, da farmaceutski pripravak služi kao preventivni ili terapijski lijek protiv glaukoma, srčanožilnih bolesti ili bolesti ili poremećaja uzrokovanih neurodegeneracijom ili ozljedom živca.
9. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time, da se koristi za prevenciju ili liječenje glaukoma, srčanožilnih bolesti ili bolesti ili poremećaja uzrokovanih neorodegeneracijom ili ozljedom živca.
HRP20160096TT 2009-06-19 2016-01-28 Supstituirani derivati izokinolina HRP20160096T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2009146040 2009-06-19
PCT/JP2010/004101 WO2010146881A1 (ja) 2009-06-19 2010-06-18 置換されたイソキノリン誘導体
EP10789260.6A EP2444395B1 (en) 2009-06-19 2010-06-18 Substituted isoquinoline derivative

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KR (1) KR101732907B1 (hr)
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AU (1) AU2010261206B2 (hr)
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CA2929545C (en) 2009-05-01 2019-04-09 Aerie Pharmaceuticals, Inc. Dual mechanism inhibitors for the treatment of disease
AU2011345969B2 (en) 2010-12-22 2016-04-21 D. Western Therapeutics Institute, Inc. Novel substituted isoquinoline derivative
JP2013035802A (ja) * 2011-08-10 2013-02-21 D Western Therapeutics Institute Inc 緑内障又は高眼圧症の予防又は治療剤
PL3811943T3 (pl) 2013-03-15 2023-06-12 Aerie Pharmaceuticals, Inc. Związek do stosowania w leczeniu zaburzeń oczu
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CN105085478B (zh) * 2014-04-28 2019-04-12 南京明德新药研发股份有限公司 异喹啉磺胺衍生物及其药物组合物和制药用途
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