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FI94420B - Förfarande för framställning av terapeutiskt användbara pentafluoretyl-substituerade valin- eller fenylalaninderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara pentafluoretyl-substituerade valin- eller fenylalaninderivat Download PDF

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Publication number
FI94420B
FI94420B FI903737A FI903737A FI94420B FI 94420 B FI94420 B FI 94420B FI 903737 A FI903737 A FI 903737A FI 903737 A FI903737 A FI 903737A FI 94420 B FI94420 B FI 94420B
Authority
FI
Finland
Prior art keywords
formula
compound
val
cf2cf3
boc
Prior art date
Application number
FI903737A
Other languages
English (en)
Finnish (fi)
Other versions
FI94420C (sv
FI903737A0 (sv
Inventor
Philippe Bey
Norton Paul Peet
Michael Richard Angelastro
Shujaath Mehdi
Original Assignee
Merrell Dow Pharma
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 Merrell Dow Pharma filed Critical Merrell Dow Pharma
Publication of FI903737A0 publication Critical patent/FI903737A0/sv
Publication of FI94420B publication Critical patent/FI94420B/sv
Application granted granted Critical
Publication of FI94420C publication Critical patent/FI94420C/sv

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Rheumatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (5)

1. I 3 R2 CH3 94420 i vilken R1' betyder detsanuna som Rx, bringas att reagera med förenlngen LiCF2CF3, eller c) en förening med formeln
5 O II NH„-CH-C-CF«,CF0 (5)
1. Förfarande för framställning av terapeutiskt an-vändbara pentafluoretyl-substituerade valin- eller fenyl-5 alaninderivat med formeln O II R-NH-CH-C-CF0CF0 (1) 1 | 2 3 R2 10 i vilken Rx Mr en aminoskyddande grupp, vilken är karboben-syloxi (Cbz), t-butyloxikarbonyl (Boc), bensoyl (Bz), me-toxibensoyl (MeOBz) eller en acylsulfonamido (Sac), tili 15 exempel 4-[(4-klorfenyl)sulfonylaminokarbonyl]fenylkarbo-nyl (C14>SacBz), 4- [ (4-bromf enyl) sulf onylaminokarbonyl ] f e-nylkarbonyl (Br4SacBz) eller 4-[fenylsulfonylaminokarbonyl] f enylkarbonyl (4>SacBz), eller Val-aminosyran eller Vai-Pro- eller Lys(Boc)-Pro-dipeptiden, vardera av vilka 20 eventuellt har en aminoskyddande grupp, vilken är Cbz, Boc, Bz, MeOBz eller Sac; R2 är en sidkedja av Vai- eller Phe-aminosyran; eller för framställning av hydrat eller farmaceutiskt god-tagbara salter därav, kännetecknat av att :-25 a) en förening med formeln OH Rx ' NH-CH-C-CF2CF3 (4 ) R2 i vilken R1' betyder detsamma som Rlr oxideras, b) en förening med formeln
2. Förfarande enligt patentkrav 1, känne- 15 tecknat av att föreningen Cbz-Val-CF2CF3 framställs.
2 I 2 3 R2 bringas att reagera med en syra med formeln 10 r1co2h i vilken Rx är ovan definierad.
3. Förfarande enligt patentkrav 1, känne-tecknat av att föreningen Boc-Val-CF2CF3 framställs.
4. Förfarande enligt patentkrav 1, känne-tecknat av att föreningen Cbz-Phe-CF2CF3 framställs. 20
5. Förfarande enligt patentkrav 1, känne- tecknat av att föreningen Boc-Val-Pro-Val-CF2CF3 framställs. t · 6
FI903737A 1989-07-26 1990-07-26 Förfarande för framställning av terapeutiskt användbara pentafluoretyl-substituerade valin- eller fenylalaninderivat FI94420C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US38562489A 1989-07-26 1989-07-26
US38562489 1989-07-26

Publications (3)

Publication Number Publication Date
FI903737A0 FI903737A0 (sv) 1990-07-26
FI94420B true FI94420B (sv) 1995-05-31
FI94420C FI94420C (sv) 1995-09-11

Family

ID=23522200

Family Applications (1)

Application Number Title Priority Date Filing Date
FI903737A FI94420C (sv) 1989-07-26 1990-07-26 Förfarande för framställning av terapeutiskt användbara pentafluoretyl-substituerade valin- eller fenylalaninderivat

Country Status (14)

Country Link
EP (1) EP0410411A3 (sv)
JP (1) JPH0386852A (sv)
KR (1) KR910002896A (sv)
CN (1) CN1049016A (sv)
AR (1) AR248143A1 (sv)
AU (1) AU632836B2 (sv)
CA (1) CA2021660A1 (sv)
FI (1) FI94420C (sv)
HU (1) HU209931B (sv)
IE (1) IE902700A1 (sv)
IL (1) IL95168A (sv)
NO (1) NO903314L (sv)
PT (1) PT94811A (sv)
ZA (1) ZA905737B (sv)

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Also Published As

Publication number Publication date
JPH0386852A (ja) 1991-04-11
NO903314D0 (no) 1990-07-25
HU904585D0 (en) 1990-12-28
PT94811A (pt) 1991-03-20
CN1049016A (zh) 1991-02-06
HU209931B (en) 1994-12-28
AU632836B2 (en) 1993-01-14
EP0410411A2 (en) 1991-01-30
ZA905737B (en) 1991-05-29
EP0410411A3 (en) 1991-12-27
FI94420C (sv) 1995-09-11
IL95168A (en) 1995-10-31
FI903737A0 (sv) 1990-07-26
IE902700A1 (en) 1991-02-27
AU5974290A (en) 1991-01-31
AR248143A1 (es) 1995-06-30
KR910002896A (ko) 1991-02-26
NO903314L (no) 1991-01-28
HUT54177A (en) 1991-01-28
CA2021660A1 (en) 1991-01-27

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Owner name: MERRELL DOW PHARMACEUTICALS INC.