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AR058800A1 - Heterociclos condensados con anillos bencenicos como inhibidores de comt, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento del mal de parkinson - Google Patents

Heterociclos condensados con anillos bencenicos como inhibidores de comt, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento del mal de parkinson

Info

Publication number
AR058800A1
AR058800A1 ARP060103074A ARP060103074A AR058800A1 AR 058800 A1 AR058800 A1 AR 058800A1 AR P060103074 A ARP060103074 A AR P060103074A AR P060103074 A ARP060103074 A AR P060103074A AR 058800 A1 AR058800 A1 AR 058800A1
Authority
AR
Argentina
Prior art keywords
alkyl
alkoxy
hydroxy
independently
ring
Prior art date
Application number
ARP060103074A
Other languages
English (en)
Inventor
Anne Luiro
Reijo Backstrom
Marko Ahlmark
Jarmo Pystynen
Elija Tiainen
Original Assignee
Orion Corp
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.)
Filing date
Publication date
Application filed by Orion Corp filed Critical Orion Corp
Publication of AR058800A1 publication Critical patent/AR058800A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • A61K31/403—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 carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/84—Naphthothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Compuestos con actividad inhibidora de la enzima COMT y son por consiguiente utiles como inhibidores de COMT y para la elaboracion de medicamentos para el tratamiento de la enfermedad de Parkinson. Reivindicacion 1: Un compuesto de Formula (1), en donde R2 está en una posicion orto a R3 y R1 está en una posicion orto a R2 o R1 está en una posicion orto a R3 y R4 está en una posicion orto a R1; R1 es cuano o nitro; R2 es hidroxi; R3 es hidroxi; R4 es H, (alquilo de C1-6, halo alquilo de C1-6, ciano, formilo, alquilo de C1-6-(C=O)-, halogeno o nitro; la línea punteada representa un enlace simple o uno doble; dos de X, Y o Z son independientemente CR5(R6)m, N(R7)n, O o S y uno de X, Y o Z es N(R7)n, o S; m es independientemente en cada ocurrencia, 0 o 1; n es independientemente en cada ocurrencia 0, 1 o 2; R5 es, independientemente en cada ocurrencia, H, alquilo de C1-6, alqunilo de C2-6, halogeno, hidroxi, alcoxi de C1-6, halo-alquilo de C1-6, hidroxi-alquilo de C1-6, alquilo de C1-6-(C=O)-, alcoxi de C1-8-(C=O)-, ciano, formilo, alquilo de C1-6-(C=S)-, (R8)2N-(C=S)-, R8-(C=NR8)-, carboxi, cicloalquilo de C3-7, heterociclilo, arilo, heteroarilo, heterociclilo-(C=O)-, aril-alquilo de C1-6, (R8)2N-, (R8)2N-alquilo de C1-6-S-, R9-(S=O)-, R9-(O=S=O)-, alcoxi de C1-6-alquilo de C1-6, alcoxi de C1-6-(C=O)-alquilo de C1-6, alquilo de C1-6-(=O)-O-, alquilo de C1-6-(C=O)-O-alquilo de C1-6, hidroxi-alcoxi de C1-6-alquilo de C1-6, alquilo de C1-6-S-alquilo de C1-6, alquilo de C1- 6-S-(C=O)-, cicloalquilo de C3-7-alquilo de C1-6, ariloxi, ariloxi-alquilo de C1-6, aril-alcoxi de C1-6, aril-alcoxi de C1-6-alquilo de C1-6 o heterociclil-(C=S)-, en donde dicho cicloalquilo de C3-7, heterociclilo, arilo o heteroarilo como tales o como parte de otro grupo son no substituidos o substituidos con 1, 2 o 3 substituyentes cada uno que es independientemente alquilo de C1-6, halogeno, hidroxi, carboxi, alcoxi de C1-6 o (R8)2N-; R6 es, independientemente en cada ocurrencia, H, (alquilo de C1-6, halogeno, hidroxi, hidroxi-alquilo de C1-6 o alcoxi de C1-6 o R5 y R6, ambos fijados al mismo átomo de carbono del anillo forman, junto con el átomo de carbono del anillo al cual están fijados, un grupo -(C=O)-; o R5 y R6, ambos fijados al mismo átomo de carbono del anillo, forman con el átomo de carbono del anillo al cual están fijados, C=C(R8)2; o R5 y R6 ambos fijados al mismo átomo de carbono del anillo forman, junto con el átomo de carbono del anillo al cual están fijados, un anillo carbocíclico insaturado o saturado de 5, 6 o 7 elementos, en donde dicho anillo es no substituido o substituido con 1 o 2 substituyentes, siendo cada uno independientemente alquilo de C1-6, halogeno, hidroxi, alcoxi o carboxi de C1-6; R7 es, independientemente de cada ocurrencia, H, alquilo de C1-6, cicloalquilo de C3-7, alcoxi de C1-6, arilo u O-, en donde dicho cicloalquilo C3-7 o arilo es substituido o no substituido con 1, 2 o 3 substituyentes siendo cada uno independientemente alquilo de C1-6, halogeno, hidroxi, alcoxi o carboxi de C1-6; o R5 y R5, R5 y R7, o R7 y R7 fijados al átomo adyacente del anillo forman, junto con los átomos anillo al cual están fijados un anillo carbocíclico saturado o insaturado de 5, 6, o 7 elementos condensado o un anillo heterocíclico saturado o insaturado de 5, 6, o 7 elementos, condensado que contiene 1 o 2 heteroátomos seleccionados de N, O y S, en donde el anillo carbo- o heterocíclico es substituido o no substituido con 1 o 2 sustituyentes siendo cada uno independientemente, alquilo de C1-6, halogeno, hidroxi, alcoxi de C1-6, carboxi u oxo; R8 es independientemente en cada ocurrencia, H, alquilo de C1-6, alcoxi de C1-6, arilo o aril-alquilo de C1-6, en donde dicho arilo como tal o como parte de otro grupo es no substituido o substituido con 1 o 2 substituido con 1 o 2 substituyentes, siendo cada uno independientemente, alquilo de C1-6, halogeno, hidroxi, carboxi o alcoxi de C1-6; R9 es independientemente en cada ocurrencia, alquilo de C1-6, (R8)2N-, hidroxi o alcoxi de C1-6; o una sal o éter de los mismos aceptables farmacéuticamente; con la condicion de que el compuesto no sea 2-bencil-7-bromo-6-nitro-benzofuran-4, 5-diol.
ARP060103074A 2005-07-18 2006-07-18 Heterociclos condensados con anillos bencenicos como inhibidores de comt, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento del mal de parkinson AR058800A1 (es)

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US (1) US8318785B2 (es)
EP (1) EP1910325B1 (es)
JP (1) JP5015152B2 (es)
KR (1) KR20080035571A (es)
CN (1) CN101282957B (es)
AR (1) AR058800A1 (es)
AT (1) ATE483702T1 (es)
AU (1) AU2006271631B2 (es)
BR (1) BRPI0613778A2 (es)
CA (1) CA2615466C (es)
DE (1) DE602006017378D1 (es)
DK (1) DK1910325T3 (es)
EA (1) EA017329B1 (es)
EC (1) ECSP088156A (es)
ES (1) ES2354114T3 (es)
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IL (1) IL188438A (es)
MX (1) MX2008000875A (es)
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UA (1) UA98608C2 (es)
WO (1) WO2007010085A2 (es)
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KR20130059390A (ko) * 2010-07-27 2013-06-05 에프. 호프만-라 로슈 아게 카테콜 ｏ―메틸트랜스퍼라아제 조절제의 확인 방법
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TWI638802B (zh) 2012-05-24 2018-10-21 芬蘭商奧利安公司 兒茶酚ｏ－甲基轉移酶活性抑制化合物
KR101551313B1 (ko) * 2014-07-28 2015-09-09 충남대학교산학협력단 신규한 인덴 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 망막 질환의 예방 또는 치료용 약학적 조성물
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CN111253335B (zh) * 2020-03-12 2023-06-06 浙江扬帆新材料股份有限公司 一种n-取代苯并异噻唑啉-3-酮衍生物的新合成方法
CN113121472B (zh) * 2021-03-05 2022-12-16 上海应用技术大学 一种利用金配合物制备n-磺酰基四氢吡咯类化合物的方法
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EA017329B1 (ru) 2012-11-30
CA2615466A1 (en) 2007-01-25
WO2007010085A2 (en) 2007-01-25
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ATE483702T1 (de) 2010-10-15
GEP20115222B (en) 2011-05-25
NZ565112A (en) 2010-09-30
EP1910325A2 (en) 2008-04-16
CN101282957B (zh) 2013-07-10
IL188438A0 (en) 2008-11-03
DE602006017378D1 (de) 2010-11-18
MX2008000875A (es) 2008-03-26
DK1910325T3 (da) 2011-01-24
IL188438A (en) 2013-07-31
CA2615466C (en) 2013-10-01
UA98608C2 (en) 2012-06-11
EP1910325B1 (en) 2010-10-06
EA200800357A1 (ru) 2008-06-30
WO2007010085A3 (en) 2007-03-29
BRPI0613778A2 (pt) 2011-02-01
PE20070206A1 (es) 2007-05-06
ES2354114T3 (es) 2011-03-10
CN101282957A (zh) 2008-10-08
MY148644A (en) 2013-05-15
ECSP088156A (es) 2008-02-20
TW200745074A (en) 2007-12-16
US20110086852A2 (en) 2011-04-14
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US8318785B2 (en) 2012-11-27
JP5015152B2 (ja) 2012-08-29
US20090209532A1 (en) 2009-08-20
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AU2006271631A1 (en) 2007-01-25
NO20080779L (no) 2008-02-13

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