CA2072836A1 - Pyrrolopyrazine derivatives - Google Patents

Pyrrolopyrazine derivatives

Info

Publication number
CA2072836A1
CA2072836A1 CA002072836A CA2072836A CA2072836A1 CA 2072836 A1 CA2072836 A1 CA 2072836A1 CA 002072836 A CA002072836 A CA 002072836A CA 2072836 A CA2072836 A CA 2072836A CA 2072836 A1 CA2072836 A1 CA 2072836A1
Authority
CA
Canada
Prior art keywords
solution
mixture
treated
methylene chloride
formula
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
CA002072836A
Other languages
English (en)
French (fr)
Inventor
Stephan Rover
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2072836A1 publication Critical patent/CA2072836A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
    • 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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA002072836A 1991-07-02 1992-06-30 Pyrrolopyrazine derivatives Abandoned CA2072836A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH1950/91 1991-07-02
CH195091 1991-07-02
CH166792 1992-05-22
CH1667/92 1992-05-22

Publications (1)

Publication Number Publication Date
CA2072836A1 true CA2072836A1 (en) 1993-01-03

Family

ID=25688329

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002072836A Abandoned CA2072836A1 (en) 1991-07-02 1992-06-30 Pyrrolopyrazine derivatives

Country Status (14)

Country Link
US (1) US5292732A (OSRAM)
EP (1) EP0521368A1 (OSRAM)
JP (1) JPH0774217B2 (OSRAM)
CN (1) CN1030986C (OSRAM)
AU (1) AU654362B2 (OSRAM)
CA (1) CA2072836A1 (OSRAM)
CS (1) CS202292A3 (OSRAM)
FI (1) FI100242B (OSRAM)
HU (1) HUT70163A (OSRAM)
IE (1) IE922152A1 (OSRAM)
IL (1) IL102337A (OSRAM)
NO (1) NO922604L (OSRAM)
NZ (1) NZ243310A (OSRAM)
TW (1) TW224974B (OSRAM)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0572863A1 (de) * 1992-06-05 1993-12-08 F. Hoffmann-La Roche Ag ZNS Pyrazinoindole
US5378846A (en) * 1993-06-11 1995-01-03 Russian-American Institute For New Drug Development 1,2,3,4-tetrahydropyrrolo-[1,2-a]-pyrazine derivatives
US5352096A (en) * 1993-09-27 1994-10-04 Chi Wen Chen Air compressor for automobiles
TW334423B (en) * 1993-10-22 1998-06-21 Hoffmann La Roche Tricyclic 1-aminoethylpyrrole-derivatives
UA66370C2 (en) * 1997-12-16 2004-05-17 Lilly Co Eli Arylpiperazines having activity to setotonin 1 receptors
TR200101886T2 (tr) 1998-12-25 2001-12-21 Shionogi & Co., Ltd. HIV integrazını önleme aktivitesi olan aromatik heterosikl bileşimleri.
ATE426605T1 (de) * 2003-06-12 2009-04-15 Merck & Co Inc Inhibitoren von mitotischem kinesin
EP1741709A1 (en) * 2005-06-28 2007-01-10 Sanofi-Aventis Deutschland GmbH Heteroaryl-substituted amides comprising a saturated linker group, and their use as pharmaceuticals
DE102006049452A1 (de) * 2006-10-17 2008-05-08 Grünenthal GmbH Substituierte Tetrahydropyrolopiperazin-Verbindungen und deren Verwendung in Arzneimitteln
AU2011263797B2 (en) 2010-06-09 2014-06-05 Janssen Pharmaceutica Nv 5,6-dihydro-2H-[1,4]oxazin-3-yl-amine derivatives useful as inhibitors of beta-secretase (BACE)
WO2012085038A1 (en) 2010-12-22 2012-06-28 Janssen Pharmaceutica Nv 5,6-DIHYDRO-IMIDAZO[1,2-a]PYRAZIN-8-YLAMINE DERIVATIVES USEFUL AS INHIBITORS OF BETA-SECRETASE (BACE)
HUE026338T2 (en) 2011-03-01 2016-05-30 Janssen Pharmaceutica Nv 6,7-dihydro-pyrazolo[1,5-a]pyrazin-4-ylamine derivatives useful as inhibitors of beta-secretase (bace)
MY163346A (en) 2011-03-09 2017-09-15 Janssen Pharmaceutica Nv 3,4-dihydro-pyrrolo[1,2-a]pyrazin-1-ylamine derivatives useful as inhibitors of beta-secretase (base)
US9303035B2 (en) * 2012-12-19 2016-04-05 Novartis Ag Substituted pyrazino[1′,2′:1,2]pyrrolo[3,4-d]pyrimidines, pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]oxazines and pyrimido[4′,5′:3,4]pyrrolo[1,2-d][1,4]oxazepines for inhibiting the CFTR channel
MX366063B (es) 2013-06-12 2019-06-26 Janssen Pharmaceutica Nv Derivados de 4-amino-6-fenil-6,7-dihidro[1,2,3]triazolo[1,5-a]pira zina como inhibidores de beta-secretasa (bace).
WO2014198853A1 (en) 2013-06-12 2014-12-18 Janssen Pharmaceutica Nv 4-amino-6-phenyl-5,6-dihydroimidazo[1,5-a]pyrazine derivatives as inhibitors of beta-secretase (bace)
WO2014198851A1 (en) 2013-06-12 2014-12-18 Janssen Pharmaceutica Nv 4-amino-6-phenyl-5,6-dihydroimidazo[1,5-a]pyrazin-3(2h)-one derivatives as inhibitors of beta-secretase (bace)
JP2017538753A (ja) 2014-12-18 2017-12-28 ヤンセン ファーマシューティカ エヌ．ベー． ２，３，４，５−テトラヒドロピリジン−６−アミンおよび３，４−ジヒドロ−２Ｈ−ピロール−５−アミンの化合物のβセクレターゼ阻害剤
KR102495650B1 (ko) * 2017-04-12 2023-02-02 에프. 호프만-라 로슈 아게 알데히드 함유 표적 분자의 라벨링 방법

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1185080A (en) * 1967-12-07 1970-03-18 Beecham Group Ltd Pyrrolidines
US3906010A (en) * 1974-06-17 1975-09-16 Morton Norwich Products Inc Series of 5-aryl-2-furamidines
US3931247A (en) * 1974-12-11 1976-01-06 Morton-Norwich Products, Inc. 5-(Substituted)phenylfurfuryl alcohols
JPS5811878B2 (ja) * 1974-12-19 1983-03-04 大正製薬株式会社 フロ （ ３ ２−ｂ ） インド−ルルイノ セイホウ
US4188389A (en) * 1978-11-03 1980-02-12 Ayerst Mckenna & Harrison, Inc. 1,2,3,4-Tetrahydropyrrolo(1,2-A)pyrazines
JPS5852995B2 (ja) * 1981-09-28 1983-11-26 武田薬品工業株式会社 フルフラ−ル誘導体の製造法
US4882354A (en) * 1987-12-16 1989-11-21 Norwich Eaton Pharmaceuticals, Inc. N-hydroxy-5-phenyl-2-furancarboximidamides useful as cardiotonic agents

Also Published As

Publication number Publication date
JPH0774217B2 (ja) 1995-08-09
CN1068328A (zh) 1993-01-27
IE922152A1 (en) 1993-01-13
IL102337A (en) 1996-01-31
IL102337A0 (en) 1993-01-14
AU654362B2 (en) 1994-11-03
CS202292A3 (en) 1993-01-13
FI923073A7 (fi) 1993-01-03
NZ243310A (en) 1994-11-25
AU1930992A (en) 1993-01-07
EP0521368A1 (de) 1993-01-07
TW224974B (OSRAM) 1994-06-11
JPH06239865A (ja) 1994-08-30
NO922604D0 (no) 1992-07-01
NO922604L (no) 1993-01-04
FI923073A0 (fi) 1992-07-02
CN1030986C (zh) 1996-02-14
HU9202139D0 (en) 1992-10-28
HUT70163A (en) 1995-09-28
US5292732A (en) 1994-03-08
FI100242B (fi) 1997-10-31

Similar Documents

Publication Publication Date Title
CA2072836A1 (en) Pyrrolopyrazine derivatives
EP1192165B1 (en) Substituted heterocycle fused gamma-carbolines
CA1242193A (en) 1-benzyl-aminoalkyl-pyrrolidinones and the acid addition salts thereof, processes for preparing them and pharmaceutical compositions
USRE39679E1 (en) Substituted heterocycle fused gamma-carbolines
US7592454B2 (en) Substituted hexahydro-pyridoindole derivatives as serotonin receptor agonists and antagonists
CA1291484C (en) 6-substituted-4-dialkylaminotetrahydrobenz¬c,d|indoles
Allen et al. Entry into 6-methoxy-D (+)-tryptophans. Stereospecific synthesis of 1-benzenesulfonyl-6-methoxy-D (+)-tryptophan ethyl ester
CZ293628B6 (cs) Benzyl(iden)laktamové deriváty a jejich použití a farmaceutické kompozice na jejich bázi
Duan et al. Rhodium (II)‐catalyzed [4+ 3] cyclization of triazoles with indole derivatives and its application in the total synthesis of (±)‐aurantioclavine
CA1244414A (en) Dibenzodiazepin derivatives, a process for their preparation and their use as medicaments
Jones et al. Direct synthesis of 2-acylindoles
Kulagowski et al. Generation and rearrangement of 4a H-carbazoles
US3514462A (en) 1 and 2 ethoxy 3,4,5,10 - tetrahydroazepino(3,4-b) and (2,3-b)indoles and corresponding amino derivatives thereof
JP2003064081A (ja) 新規なオクタヒドロ−２Ｈ−ピリド〔１，２−ａ〕ピラジン化合物、それらの製造方法およびそれらを含む医薬組成物
US5030636A (en) Octahydrobenzo(f)quinoline derivatives
US20020068748A1 (en) Diazabicyclooctane derivatives and therapeutic uses thereof
Whitehead et al. Reactions of Orthoesters with Aryl Isocyanates
CA1324607C (en) Dipyrazoles useful as bronchodilators
US4245095A (en) Indolo isoquinoline compounds
Moody et al. Ring cleavage of a 3-azidothiophene: novel extrusion of acetylene
Bajwa et al. Fischer indole synthesis. The reaction of N′-alkyl-2, 6-dialkylphenylhydrazines with cyclohexanone
JPS62240685A (ja) 置換ピリミドインド−ル
CZ202292A3 (cs) Způsob zpracování slupek plodu ostropestřce mariánského
US3291807A (en) Process for production of 5-(indol-3-yl)-2-pyrrolidinones
US4379932A (en) Process for preparing spiro[indoline-3,4'-piperidine]s

Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued