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FI73677B - Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 3-metylflavon-8-karboxylsyraestrar. - Google Patents

Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 3-metylflavon-8-karboxylsyraestrar. Download PDF

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Publication number
FI73677B
FI73677B FI822493A FI822493A FI73677B FI 73677 B FI73677 B FI 73677B FI 822493 A FI822493 A FI 822493A FI 822493 A FI822493 A FI 822493A FI 73677 B FI73677 B FI 73677B
Authority
FI
Finland
Prior art keywords
general formula
methylflavone
hydrogen atom
carbon atoms
group
Prior art date
Application number
FI822493A
Other languages
English (en)
Finnish (fi)
Other versions
FI822493L (fi
FI73677C (sv
FI822493A0 (fi
Inventor
Renzo Pennini
Pietro Cazzulani
Dante Nardi
Alberto Tajana
Gabriele Graziani
Silvano Casadio
Original Assignee
Recordati Chem Pharm
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 Recordati Chem Pharm filed Critical Recordati Chem Pharm
Publication of FI822493A0 publication Critical patent/FI822493A0/fi
Publication of FI822493L publication Critical patent/FI822493L/fi
Publication of FI73677B publication Critical patent/FI73677B/fi
Application granted granted Critical
Publication of FI73677C publication Critical patent/FI73677C/sv

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02Muscle relaxants, e.g. for tetanus or cramps
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00Anaesthetics
    • A61P23/02Local anaesthetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/12Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D451/00Heterocyclic 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
    • C07D451/02Heterocyclic 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
    • C07D451/04Heterocyclic 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
    • C07D451/06Oxygen atoms
    • C07D451/12Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D453/00Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Obesity (AREA)
  • Anesthesiology (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Neurosurgery (AREA)
  • Endocrinology (AREA)
  • Biomedical Technology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (4)

1. Förfarande för framställning av nya, terapeu-tiskt användbara 3-metylflavon-8-karbonsyraestrar med 5 den allmänna formeln (I) QÖT. · cooz väri Z betecknar N-metylpiperidyl, tropyl eller kinukli-dyl eller en grupp med den allmänna formeln (II) 15 f ? /-\ - C - C - (CH,) -N > (II) i ( 2 n v / R·, R, \_/ R3^ 20 väri n är 0 eller 1, R betecknar en väteatom, en alkyl-grupp med 1-4 kolatomer eller en fenylgrupp, R^ betecknar en väteatom eller en alkylgrupp med 1-4 kolatomer, R^ betecknar en väteatom eller en hydroxigrupp eller R, R^ och R^ tillsammans med de kolatomerna, vid vilka de 25 är bundna, bildar en cyklohexylgrupp, och R^ betecknar en väteatom eller en alkylgrupp med 1-4 kolatomer, under förutsättning, att R, R1, R2 och R3 inte alla samtidigt betecknar väte, samt farmaceutiskt godtagbara salter därav, kännetecknat därav, att man 30 a) kondenserar en 3-metylflavon-8-karbonsyrahalo- genid med den allmänna formeln (III) O CH 35 ij Ϊ 3 (III) co-x 18 7 3 6 7 7 väri X betecknar en haiogenatom, företrädesvis en klor-atom, raed en aminoalkohol mdd den allmänna forineln ZOH, varvid Σ betecknar samir.a som ovan, eller b) för fram.ställning av föreningar med den all-5 manna forineln (I), väri Z betecknar en grupp med den allmänna formeln (II1) - C - C - CH - N \ (II')
10. OH \_/ R3^ väri betecknar en väteatom eller en alkylgrupp med 1-4 ko.latomer, omsätter en förening med den allmänna 15 formeln (IV) n I (IV) ^ R-
20. J väri betecknar sar;r.a som ovan, med 2,3-epoxipropyl- 3-metylflavon-3-karboxyla 1 i närvaro av en katalysatorn, företrädesvis trietylamin, och 25 ifall önskvärt, omvandlar den erhällna produktcn tili ett syraadditionssalt.
2. Fbrfaranäe enligt punkten a) av patentkravet 1, k ä n n e t e o k n a t därav, att man uppvärmer aminoalkoholen med ett överskott av flavonderivatet vid 30 140-200°C i fränvaro av ett lösningsmedel.
3. Förfarande enligt punkten a) av patentkravet 1, känneteckna t därav, att man omsätter aminoalkoholen med en ekvimoiar mängd av flavonderivatet i närvaro av ett lösningsmedel vid en temperatur av 0°C 35 tili äterflödestemperaturen hos lösningsmedlet, even-tuellt i närvaro av ett syrabindande niedol. Il
FI822493A 1981-07-17 1982-07-13 Förfarande för framställning av nya, terapeutiskt användbara 3-metylf lavon-8-karboxylsyraestrar. FI73677C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8122158 1981-07-17
GB8122158 1981-07-17

Publications (4)

Publication Number Publication Date
FI822493A0 FI822493A0 (fi) 1982-07-13
FI822493L FI822493L (fi) 1983-01-18
FI73677B true FI73677B (fi) 1987-07-31
FI73677C FI73677C (sv) 1987-11-09

Family

ID=10523330

Family Applications (1)

Application Number Title Priority Date Filing Date
FI822493A FI73677C (sv) 1981-07-17 1982-07-13 Förfarande för framställning av nya, terapeutiskt användbara 3-metylf lavon-8-karboxylsyraestrar.

Country Status (25)

Country Link
US (1) US4550115A (sv)
EP (1) EP0072620B1 (sv)
JP (1) JPS5835185A (sv)
KR (1) KR870000275B1 (sv)
AR (1) AR231543A1 (sv)
AT (1) ATE16806T1 (sv)
AU (1) AU553322B2 (sv)
CA (1) CA1221969A (sv)
DE (1) DE3267782D1 (sv)
DK (1) DK160498C (sv)
ES (1) ES513993A0 (sv)
FI (1) FI73677C (sv)
GB (1) GB2104507B (sv)
GR (1) GR81300B (sv)
HU (1) HU189601B (sv)
IE (1) IE53525B1 (sv)
IL (1) IL66187A0 (sv)
IT (1) IT1198389B (sv)
NO (1) NO157330C (sv)
NZ (1) NZ200981A (sv)
PH (1) PH18001A (sv)
PT (1) PT75230B (sv)
SG (1) SG77784G (sv)
YU (2) YU136682A (sv)
ZA (1) ZA824335B (sv)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58225083A (ja) * 1982-06-23 1983-12-27 Nippon Shinyaku Co Ltd メチルフラボン誘導体
FR2531083B1 (fr) * 1982-06-29 1986-11-28 Sandoz Sa Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments
IT1229856B (it) * 1989-04-20 1991-09-13 Recordati Chem Pharm Compresse a rilascio controllato contenenti flavossato.
US5605896A (en) * 1992-02-25 1997-02-25 Recordati S.A., Chemical And Pharmaceutical Company Bicyclic heterocyclic derivatives having α1 adrenergic and 5HT1A activities
US5474994A (en) * 1992-05-26 1995-12-12 Recordati S.A., Chemical And Pharmaceutical Company Bicyclic heterocyclic derivatives having α1 -adrenergic and 5HT1A
IT1254469B (it) * 1992-02-25 1995-09-25 Recordati Chem Pharm Derivati benzopiranici e benzotiopiranici
SG65570A1 (en) 1992-02-25 1999-06-22 Recordati Chem Pharm Heterobicyclic compounds
IT1258315B (it) * 1992-04-10 1996-02-22 Recordati Chem Pharm Derivati del flavone
US6087366A (en) * 1996-03-07 2000-07-11 The Trustees Of Columbia University In The City Of New York Use of flavopiridol or a pharmaceutically acceptable salt thereof for inhibiting cell damage or cell death
US7501443B2 (en) 2002-12-23 2009-03-10 Ranbaxy Laboratories Limited Flavaxate derivatives as muscarinic receptor antagonists

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2921070A (en) * 1957-11-05 1960-01-12 Recordati Lab Farmacologico S Basic esters of 3-methylflavone-8-carboxylic acid
US4217351A (en) * 1976-08-04 1980-08-12 Abbott Laboratories Benzopyrano quinuclidines useful as antiglaucoma agents

Also Published As

Publication number Publication date
PT75230A (fr) 1982-08-01
IE821678L (en) 1983-01-17
YU136682A (en) 1985-06-30
IT1198389B (it) 1988-12-21
IE53525B1 (en) 1988-12-07
IL66187A0 (en) 1982-11-30
AU8609882A (en) 1983-01-20
SG77784G (en) 1985-04-26
ES8400109A1 (es) 1983-10-16
PT75230B (fr) 1984-07-23
PH18001A (en) 1985-02-28
GR81300B (sv) 1984-12-11
ES513993A0 (es) 1983-10-16
GB2104507A (en) 1983-03-09
FI822493L (fi) 1983-01-18
HU189601B (en) 1986-07-28
AU553322B2 (en) 1986-07-10
NO157330C (no) 1988-03-02
IT8222274A0 (it) 1982-07-07
ZA824335B (en) 1983-05-25
GB2104507B (en) 1984-09-19
YU125184A (en) 1985-04-30
JPH0251914B2 (sv) 1990-11-08
FI73677C (sv) 1987-11-09
NZ200981A (en) 1984-10-19
ATE16806T1 (de) 1985-12-15
KR870000275B1 (ko) 1987-02-23
DK301982A (da) 1983-01-18
KR840000521A (ko) 1984-02-25
CA1221969A (en) 1987-05-19
AR231543A1 (es) 1984-12-28
EP0072620B1 (en) 1985-12-04
US4550115A (en) 1985-10-29
EP0072620A1 (en) 1983-02-23
FI822493A0 (fi) 1982-07-13
NO822127L (no) 1983-01-18
DK160498C (da) 1991-08-26
DE3267782D1 (en) 1986-01-16
JPS5835185A (ja) 1983-03-01
DK160498B (da) 1991-03-18
NO157330B (no) 1987-11-23

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Owner name: RECORDATI S.A., CHEMICAL AND