FI112943B - Pyrimidinylderivat och deras användning för framställning av ett läkemedel för inhibering av interleukin proteasaktivitet - Google Patents

Pyrimidinylderivat och deras användning för framställning av ett läkemedel för inhibering av interleukin proteasaktivitet Download PDF

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Publication number
FI112943B
FI112943B FI963897A FI963897A FI112943B FI 112943 B FI112943 B FI 112943B FI 963897 A FI963897 A FI 963897A FI 963897 A FI963897 A FI 963897A FI 112943 B FI112943 B FI 112943B
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Finland
Prior art keywords
phenyl
oxo
aspartic acid
dihydro
acetoyl
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FI963897A
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English (en)
Finnish (fi)
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FI963897A0 (sv
FI963897A (sv
Inventor
Roland E Dolle
Stanley J Schmidt
Catherine P Prouty
Prasad V C Chaturvedula
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Vertex Pharma
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    • 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
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • 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]
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Claims (9)

1. Förening enligt formel (I) eller dess farma-ceutiskt godtagbara salt 5 o Nf o Λ IIx /v Ri N γ' N fi O H H I vari Y är h^Y^r6 H^7k^R7 eller 10 o &A o R7 eller OH Rs är OR8, väri R8 är H eller alkyl;
15 R2 är Ci-C6-alkyl; fenyl, tienyl eller pyridinyl, I varvid fenyl, tienyl eller pyridinyl har eventuellt sub- stituerats med halogen; R? är H, CH20 (CO) o-i-fenyl, varvid fenylgruppen eventuellt har substituerats med halogen, CH2OP (0) Ri4Ri5, \ 20 o ; h cf3 Κΐ4γΥ : // \ Λ Λ -ch2° YY ; -CH20 xn A. JL I H H * R16 , H 35 r 4: väri R14 är fenyl; R15 är fenyl; Rie är fenyl eller pyridinyl, varvid fenyl eller 5 pyridinyl eventuellt har substituerats med halogen; Rx är Cx-Cg-alkoxi, Ci-C6-alkoxi fenyl eller fenyl, som eventuellt har substituerats med Ci-C6-alkyltio.
2. Förening enligt patentkrav 1, känneteck-nad av att R2 är fenyl, pyridinyl eller tienyl. 10
3. Förening enligt patentkrav 1, känneteck- nad av att den har valts frän följande grupp: N- [2-(5-bensyloxikarbonylamino-6-oxo-2-(4-fluorfenyl)-1,6-dihydro-1-pyrimidinyl)acetoyl-L-asparaginsyra-2,6-diklorbensoyl-oximetylketon, N-[2-(5-tiometylbensoylamino-6-oxo-2-(4- 15 fluorfenyl)-1,6-dihydro-1-pyrimidinyl)acetoyl]-L-asparaginsyra-2 ,6-diklorbensoyloximetylketon, N- [2-(5-bensyloxi-karbonylamino-6-oxo-2-(4 -fluorfenyl)-1,6-dihydro-1-pyrimi -dinyl)acetoyl]-L-asparaginsyradifenylfosfinoximetylketon, N-[2-(5-bensyloxikarbonylamino-6-oxo-2-(4-fluorfenyl)-1,6-20 dihydro-1-pyrimidinyl)acetoyl]-L-asparaginsyra-5-(1-(4- klorfenyl)-3-trifluormetyl)pyrazoloximetylketon, N-[2-(5-” bensyloxikarbonylamino-6-oxo-2-(4 -fluorfenyl)-1,6-dihydro- • 1-pyrimidinyl)acetoyl]-L-asparaginsyra-5-(3-fenyl)kumari- • nyloximetylketon, N- [2-(5-bensyloxikarbonylamino-6-oxo-2- : 25 (4-fluorfenyl)-1,6-dihydro-1-pyrimidinyl)acetoyl]-L-aspa- raginsyra-5-(1-fenyl-3-trifluormetyl)pyrazoloximetylketon, N- [2-(5-isopropyloxikarbonylamino-6-oxo-2-fenyl-1,6-dihydro -1-pyrimidinyl)acetoyl]-L-asparaginsyra-5-(l-fenyl-3-trifluormetyl)pyrazoloximetylketon, N-[2-(5-bensyloxikar-! 30 bonylamino-6-oxo-2-(3-pyridinyl)-1,6-dihydro-1-pyrimidi nyl) acetoyl]-L-asparaginsyra-5-(1-fenyl-3-trifluormetyl)- • pyrazoloximetylketon, N-[2-(5-bensyloxikarbonylamino-6- : oxo-2-(2-tienyl)-1,6-dihydro-1-pyrimidinyl)acetoyl]-L-as- paraginsyra-5 -(l-fenyl-3-trifluormetyl)pyrazoloximetyl-35 keton, N-[2 -(5-bensyloxikarbonylamino-6-oxo-2-metyl-1,6-dihydro-1-pyrimidinyl)acetoyl]-L-asparaginsyra-5-(1-fenyl- 36 1 'k. >43 3 -trifluormetyl)pyrazo1oximetyIketon, N-[2-(5-bensyloxi-karbonylamino-6-oxo-2-(2 -tienyl)-1,6-dihydro-1-pyrimidi -nyl)acetoyl]-L-asparaginsyra-5-(1-(2-pyridinyl)-3-tri-fluormetyl)pyrazoloximetylketon, N-[2-(5-bensyloxikarbo-5 nylamino-6-oxo-2-(2-tienyl)]-L-asparaginsyra-5-(1-(4-klor-fenyl)-3-trifluormetyl)pyrazoloximetylketon, N-[2-(5- bensyloxikarbonylamino-6-oxo-2-(2-tienyl)]-L-asparaginsy-ra-2,6-diklorbensoyloximetylketon, N-[2 -(5-bensyloxikarbo-nylamino-6-oxo-2-(2-tienyl)-1,6-dihydro-1-pyrimidinyl) ace- 10 toyl]-L-asparaginsyraaldehyd.
4. Farmaceutisk komposition, kännetecknad av att den omfattar en förening enligt nägot av patentkra-ven 1-3 eller dess farmaceutiskt godtagbara salt och en farmaceutisk godtagbar bärare.
5. Användning av en förening enligt nägot av pa- tentkraven 1-3 eller dess farmaceutiskt godtagbara sait vid framställning av ett läkemedel, vilket läkemedel är avsett för inhibering av interleukin-ip-proteasaktivitet hos ett däggdjur som är i behov av dylik värd. 2 0
6. Användning av en förening enligt nägot av pa- tentkraven 1-3 eller dess farmaceutiskt godtagbara sait · vid framställning av ett läkemedel, som är avsett för värd • eller förebyggande av sjukdomar eller störningar, som : väljs bland smittosamma sjukdomar, luftvägssjukdomar, in- 25 flammationstillständ, immunhärstammande sjukdomar, autoim- munsjukdomar, bensjukdomar, tumörer och leukemier, hos ett ·. däggdjur som är i behov av dylik värd.
7. Användning av en förening enligt nägot av pa-, tentkraven 1-3 eller dess farmaceutiskt godtagbara sait ; 30 vid framställning av ett läkemedel, som är avsett för värd och förebyggande av sjukdomar eller störningar, som väljs ; bland hjärnhinneinflammation, örontrumpetinflammation, • septisk chock, ledinflammation, gallgängsinflammation, tjocktarmsinflammation, hjärninflammation, endokerolit, 35 hepatit, bukspottkörtelinflammation, reperfusionskador, överkänslighet, MS-sjukdom, reumatoid artrit, artros, in- 37 11η; 43 flammatorisk tarmsjukdom, blodförgiftning, akut myeloge-nisk leukemi, kronisk myelogenisk leukemi, osteoporos och ulcerös kölit, hos ett däggdjur som är i behov av dylik värd.
8. Användning enligt patentkrav 7, känneteck- nad av att sjukdomen eller störningen är septisk chock, reumatoid artrit, artros, inflammatorisk tarmsjukdom, buk-spottkörtelinflammation eller ulcerös kölit.
9. Förening enligt formel (I) för användning som 10 ett terapeutiskt medel. • · • · » ( * I ♦ * » > t , • I 3 « · I * · I •
FI963897A 1994-03-31 1996-09-27 Pyrimidinylderivat och deras användning för framställning av ett läkemedel för inhibering av interleukin proteasaktivitet FI112943B (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US22171294A 1994-03-31 1994-03-31
US22171294 1994-03-31
PCT/US1995/003909 WO1995026958A1 (en) 1994-03-31 1995-03-29 Pyrimidinyl derivatives as interleukin inhibitors
US9503909 1995-03-29

Publications (3)

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FI963897A0 FI963897A0 (sv) 1996-09-27
FI963897A FI963897A (sv) 1996-09-27
FI112943B true FI112943B (sv) 2004-02-13

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US (3) US5670494A (sv)
EP (1) EP0752987B1 (sv)
JP (1) JP3703836B2 (sv)
CN (2) CN1118458C (sv)
AT (1) ATE254111T1 (sv)
AU (1) AU703451B2 (sv)
CA (1) CA2186511C (sv)
DE (1) DE69532113T2 (sv)
DK (1) DK0752987T3 (sv)
ES (1) ES2210289T3 (sv)
FI (1) FI112943B (sv)
HK (1) HK1012623A1 (sv)
HU (1) HU224731B1 (sv)
MX (1) MX9604420A (sv)
NO (1) NO308603B1 (sv)
NZ (1) NZ283876A (sv)
PT (1) PT752987E (sv)
WO (1) WO1995026958A1 (sv)

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AU703451B2 (en) 1999-03-25
FI963897A0 (sv) 1996-09-27
FI963897A (sv) 1996-09-27
DE69532113T2 (de) 2004-07-29
DK0752987T3 (da) 2004-03-15
CN1118458C (zh) 2003-08-20
CA2186511A1 (en) 1995-10-12
WO1995026958A1 (en) 1995-10-12
JPH09511249A (ja) 1997-11-11
HUT75715A (en) 1997-05-28
HK1012623A1 (en) 1999-08-06
CN1504462A (zh) 2004-06-16
EP0752987B1 (en) 2003-11-12
US20010003750A1 (en) 2001-06-14
NO964058L (no) 1996-09-26
US6407080B2 (en) 2002-06-18
NZ283876A (en) 2001-03-30
DE69532113D1 (de) 2003-12-18
CA2186511C (en) 2009-02-10
AU2232395A (en) 1995-10-23
NO964058D0 (no) 1996-09-26
ATE254111T1 (de) 2003-11-15
MX9604420A (es) 1997-12-31
EP0752987A1 (en) 1997-01-15
EP0752987A4 (en) 1997-04-09
US6162800A (en) 2000-12-19
JP3703836B2 (ja) 2005-10-05
ES2210289T3 (es) 2004-07-01
US5670494A (en) 1997-09-23
HU224731B1 (en) 2006-01-30
HU9602664D0 (en) 1996-11-28
CN1149292A (zh) 1997-05-07
NO308603B1 (no) 2000-10-02
PT752987E (pt) 2004-03-31

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