FI106461B - Förfarande för framställning av terapeutiskt användbara enantiomeriska föreningar samt vid förfarandet användbar mellanprodukt - Google Patents

Förfarande för framställning av terapeutiskt användbara enantiomeriska föreningar samt vid förfarandet användbar mellanprodukt Download PDF

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FI106461B
FI106461B FI906367A FI906367A FI106461B FI 106461 B FI106461 B FI 106461B FI 906367 A FI906367 A FI 906367A FI 906367 A FI906367 A FI 906367A FI 106461 B FI106461 B FI 106461B
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formula
methanol
compound
salt
amino
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FI906367A
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Finnish (fi)
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FI906367A (fi
FI906367A0 (fi
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Susan Mary Daluge
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Wellcome Found
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Priority to FI970666A priority Critical patent/FI105813B/sv
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Virology (AREA)
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  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (5)

1. Förfarande för framställning av terapeutiskt an-vändbara enantiomeriska föreningar med den allmänna formeln 5 Jy\
10 H2N^N (i) A väri R är en cyklopropylamino- eller N-cyklopropyl-N-15 metylaminogrupp och A är en 2-cyklopenten-l-metanol-4-ylgrupp i (IS,4R)-konfiguration, samt deras salter eller estrar, eller salter av estrar, varvid nämnda föreningar och deras salter eller estrar, eller salter av estrar, en-var förligger i form av en enantiomer, väsentligen fri frän 20 motenantiomer, kännetecknat av att A) en enantiomerförening med formeln £ : .· 25 k JL / • · · Δ I ::: a • · • » s'·'·' där A är en i det föregäende definierad grupp och Z är en • · · prekursorgrupp tili den i samband med formeln I definierade 30 gruppen R, eller ett sait eller en ester, eller ett sait av • · *···1 en ester, av densamma, behandlas med ett ämne eller vid be- • · · ...1 tingelser, vilka ästadkommer att prekursorgruppen Z omvand- ·;··· las tili en önskad grupp R; eller • · • · · « · « • · · « · t • · » 61 106461 B) en enantiomer förening med formeln R N ,-
5 JL (HI) R3Nlf^N ^NH A där A och R är i det föregäende definierade grupper, R2 är väte eller en formylgrupp och R3 är en aminoskyddsgrupp, 10 ett salt eller ester, eller ett salt av en ester, av den-samma, omsätts med ett ämne, som ästadkommer att en imidat-soliring bildas i den önskade föreningen med formeln I och att aminoskyddsgruppen R3 avlägsnas; eller C) enantiomerförening med formeln 15 1. ii / (IV) r3nh'^n'^^ 20 a där A och R är i det föregäende definierade grupper och R3 : är en aminos kyddsgrupp, eller ett salt eller en ester, el- < : ler ett salt av en ester, av densamma, omsätts med ett ämne 1 ' ; 25 som ästadkommer att skyddsgruppen R3 avlägsnas, och möjli- • ♦ j j*j gen utförs den ena eller bägge av följande omvandlingar i • I» .···, vilken som heist önskad följd: I·· i) när en förening med formeln I har bildats, om-vandlas den nämnda föreningen till ett salt eller en ester, 30 eller ett salt av en ester; eller ♦ · *···* ii) när ett salt eller en ester, eller ett salt av • · · • · ···* en ester av föreningar med formeln I har bildats, omvandlas ·;··· detta respektive denna till en utgängsförening med formeln ....: I eller till ett salt eller en ester, eller ett salt av en • 35 ester. « · 4 4 4 ♦ 4 ♦ 1 φ 4 4 4 • 4 4 4 4 62 106461
2. Förfarande enligt patentkrav 1, kanne-tecknat av att man framställer (IS,4R)-cis-4- [2-amino-6-(cyklopropylamino)-9H-purin-9-yl]-2-cyklopenten-l-metanol, i form som är väsentligen fri frän motsvarande 5 (1R, 4S)-enantiomer.
3. Förfarande enligt patentkrav 1, känne- t e c k n a t, av att man framställer (IS, 4R) -cis-4-[2-amino-6-(N-cyklopropyl-N-metylamino)-9H-purin-9-yl]-2-cyklopenten-l-metanol, i form som är väsentligen fri frän 10 motsvarande (1R,4S)-enantiomer.
4. Förfarande enligt patentkrav 1 för framställning av farmaceutiskt godtagbara salter, estrar och salter av estrar, av (IS,4R)-enantiomera föreningar.
5. Förening som är användbar säsom mellanprodukt vid 15 framställning av föreningar med formeln I medelst förfarande C i patentkrav 1 och som har formeln N^Sr/\ | I x) (IV) 20 ,¾ A» A ; där A är 2-cyklopenten-l-metanol-4-yl i (1S,4R)~ * konfiguration, R3 är en Ci-g-alkanoylgrupp och R är en cyk- . 25 lopropylamino- eller N-cyklopropyl-N-metylaminogrupp. • · • · « « · · • · · • · · • · • · · * · · • · · « · · • · · : : j • · · • · · • ♦ ♦ · ♦ t « « · < < i t • M M • ·
FI906367A 1989-12-22 1990-12-21 Förfarande för framställning av terapeutiskt användbara enantiomeriska föreningar samt vid förfarandet användbar mellanprodukt FI106461B (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI970666A FI105813B (sv) 1989-12-22 1997-02-17 Enantiomeriska mellanprodukter

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45520189 1989-12-22
US07/455,201 US5034394A (en) 1988-06-27 1989-12-22 Therapeutic nucleosides

Publications (3)

Publication Number Publication Date
FI906367A0 FI906367A0 (fi) 1990-12-21
FI906367A FI906367A (fi) 1991-06-23
FI106461B true FI106461B (sv) 2001-02-15

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Family Applications (2)

Application Number Title Priority Date Filing Date
FI906367A FI106461B (sv) 1989-12-22 1990-12-21 Förfarande för framställning av terapeutiskt användbara enantiomeriska föreningar samt vid förfarandet användbar mellanprodukt
FI20001175A FI20001175A (sv) 1989-12-22 2000-05-16 Enantiomeriska föreningar som är väsentligen fria från motverkande enentiomerer

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FI20001175A FI20001175A (sv) 1989-12-22 2000-05-16 Enantiomeriska föreningar som är väsentligen fria från motverkande enentiomerer

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CA2033044C (en) 1999-07-13
FI20001175A (sv) 2000-05-16
CN1028106C (zh) 1995-04-05
EP0434450A2 (en) 1991-06-26
DE69033197D1 (de) 1999-08-12
EP0921114A1 (en) 1999-06-09
HU219454B (hu) 2001-04-28
IE990826A1 (en) 2000-12-13
FI906367A (fi) 1991-06-23
RU2091386C1 (ru) 1997-09-27
AU633672B2 (en) 1993-02-04
ZA9010365B (en) 1992-08-26
DE19975058I1 (de) 2007-01-25
CN1054981A (zh) 1991-10-02
HU220630B1 (hu) 2002-03-28
JPH11158160A (ja) 1999-06-15
ES2133138T3 (es) 1999-09-01
SK658390A3 (en) 1999-10-08
CZ283481B6 (cs) 1998-04-15
HU220067B (hu) 2001-10-28
EP0434450A3 (en) 1992-07-08
JPH11343292A (ja) 1999-12-14
IE904652A1 (en) 1991-07-17
SK280000B6 (sk) 1999-06-11
TW371660B (en) 1999-10-11
SG49685A1 (en) 1998-06-15
NL990028I2 (nl) 2000-02-01
IL96748A (en) 1995-07-31
PT96321A (pt) 1991-09-30
HU9902543D0 (en) 1999-10-28
IE990825A1 (en) 2000-12-13
EP0434450B1 (en) 1999-07-07
DE69033197T2 (de) 1999-10-28
NZ236593A (en) 1994-01-26
CA2033044A1 (en) 1991-06-23
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HU9008407D0 (en) 1991-07-29
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AP196A (en) 1992-06-30
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LU90426I2 (fr) 1999-10-06
RU2068849C1 (ru) 1996-11-10
IL96748A0 (en) 1991-09-16
HU9902539D0 (en) 1999-10-28
AU6841990A (en) 1991-06-27
PT96321B (pt) 1998-06-30
PL288403A1 (en) 1992-06-26
ATE181917T1 (de) 1999-07-15
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