LV11459B - New substituted azetidinones as anti-inflammatory and antidegenerative agents - Google Patents

New substituted azetidinones as anti-inflammatory and antidegenerative agents Download PDF

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Publication number
LV11459B
LV11459B LVP-96-24A LV960024A LV11459B LV 11459 B LV11459 B LV 11459B LV 960024 A LV960024 A LV 960024A LV 11459 B LV11459 B LV 11459B
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LV
Latvia
Prior art keywords
alkyl
compound
substituted
carboxyl
ethyl
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LVP-96-24A
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English (en)
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LV11459A (lv
Inventor
Shrenik K Shah
Paul E Finke
James B Doherty
Peter L Barker
Hagmann William
Conrad P Dorn
Raymond A Firestone
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Merck & Co Inc
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Publication of LV11459A publication Critical patent/LV11459A/lv
Publication of LV11459B publication Critical patent/LV11459B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (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)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Reinforced Plastic Materials (AREA)

Claims (10)

  1. LV 11459 Izgudrojuma formula 1. Savienojums ar formulu (I)
    (i) kurā: R un R1 neatkarīgi viens no otra ir Ci-ealkilgrupa vai Ci^alkoksi-Ci^al-kilgrupa; M ir (1) ūdeņraža atoms, (2) Cļ^alkilgrupa, (3) C2^alkenilgrupa, (4) Ci-ealkoksi-C^alkilgrupa; X5 ir (1) ūdeņraža atoms, (2) C^alkilgrupa, (3) halogēnaizvietota Ci.6alkilgrupa, (4) C2-6alkenilgrupa, (5) C2^alkinilgrupa, (6) karboksilgrupa, (7) karboksilaizvietota Ci^alkilgrupa, (8) karboksilaizvietota Cļ-ealkilkarbonilgrupa, (9) karboksilaizvietota Ci^alkilkarbonilaminogrupa, (10) karboksilaizvietota C2-6alkenilgrupa, 1 I (11) hidroksilaizvietota C^alkilgrupa, (12) Ci^alkilkarbonilgrupa, (13) Ci^alkilkarbonilaminogrupa, (14) di(Ci ^alkil)amino-Ci^alkilgrupa; Xe ir (1) ūdeņraža atoms, (2) Ci^alkilgrupa, (3) halogēna atoms, (4) karboksilgrupa, (5) Cļ^alkoksigrupa, (6) fenilgrupa, (7) Ci-ealkilkarbonilgrupa, (8) di(Ci^alkil)aminogrupa, (9) fenoksigrupa, (10) metilēndioksigrupa, (11) 2- vai 3-furanilgrupa, (12) 2- vai 3-tienilgrupa, kā arī šī savienojuma farmaceitiski pieņemamās sēlis.
  2. 2. Savienojums pēc 1. punkta, kas atšķiras ar to, ka tajā: R un R1 neatkarīgi viens no otra ir Cļ^alkilgrupa, X5 ir karboksilgrupa vai karboksilaizvietota Ci^alkilgrupa.
  3. 3. Savienojums pēc 2. punkta, kas atšķiras ar to, ka tajā: M ir Ci.3alkilgrupa vai allilgrupa, Χβ ir ūdeņraža atoms, Ci^alkilgrupa, 3,4-metilēndioksigrupa vai fenil grupa.
  4. 4. Savienojums pēc 3. punkta, kas atšķiras ar to, ka tajā: R ir etilgrupa, R1 ir metilgrupa vai etilgrupa.
  5. 5. Savienojums pēc 4. punkta, kas atšķiras ar to, ka tajā: R un R1 ir etilgrupas, M ir n-propilgrupa, X5 ir 4-karboksimetilgrupa, X6 ir 4-metilgrupa vai 3,4-metilēndioksigrupa.
  6. 6. Farmaceitiskā kompozīcija cilvēka leikocītu elastāzes inhibēšanai, kas ietver netoksisku terapeitiski efektīvu daudzumu savienojuma pēc 1. punkta un farmaceitiski pieņemamu nesēju.
  7. 7. Kompozīcija pēc 6. punkta, kas atšķiras ar to, ka tajā: R ir etilgrupa, 2 LV 11459 R1 ir metilgrupa vai etilgrupa, M ir Ci-3alkilgrupa vai allilgrupa, X5 ir karboksilgrupa vai karboksilaizvietota Ci^alkilgrupa, X6 ir ūdeņraža atoms vai Ci^alkilgrupa, 3,4-metilēndioksigrupa vai fenilgrupa.
  8. 8. Kompozīcija pēc 7. punkta, kas atšķiras ar to, ka tajā: R1 ir etilgrupa, M ir n-propilgrupa, Xs ir 4-karboksimetilgrupa, Xe ir 4-metilgrupa vai 3,4-metilēndioksigrupa.
  9. 9. Paņēmiens savienojumu pēc 1. punkta iegūšanai, kas atšķiras ar to, ka tajā: (1) savienojumu ar formulu (B)
    O ή-NH (B) apstrādā ar savienojumu (C)
    kur: X5’ ir: (1) ūdeņraža atoms, (2) Ci^alkilgrupa, (3) halogēnaizvietota Cļ^alkilgrupa, (4) C2-6alkenilgrupa, (5) C^alkinilgrupa, (6) Ci^alkoksikarbonilgrupa, (7) ar Ci^alkoksikarbonilgrupu aizvietota Ci^alkilgrupa, (8) ar Ci^alkoksikarbonilgrupu aizvietota Ci^alkilkarbonil-grupa, (9) ar Ci.6alkoksikarbonilgrupu aizvietota Ci^alkilkarbonil-aminogrupa, (10) ar Ci^alkoksikarbonilgrupu aizvietota C2_ 6alkenilgrupa, (11) hidroksialkilgrupa, 3 (12) Ci^alkilkarbonilgrupa, (13) Cļ^alkilkarbonilaminogrupa, (14) di(Ci.6alkil)amino-Ci-6alkilgrupa bāzes klātbūtnē, iegūstot savienojumu ar formulu (D)
    CD) un tālāk (E) (2) iegūto savienojumu (D) apstrādā ar savienojumu (E) 0=C=N—CH— bāzes klātbūtnē, pēc tam neobligāti pārvērš X5’ par X5, galarezultātā iegūstot savienojumu ar formulu (A).
    CA).
  10. 10. Paņēmiens pēc 9. punkta, kas atšķiras ar to, ka: posmu (1) veic sārma metāla hidroksīda klātbūtnē, posmu (2) veic tri(Ci^alkil)amīna klātbūtnē un X5’ pārvērš par Χ5 stipras skābes klātbūtnē. 4
LVP-96-24A 1988-04-11 1996-02-01 New substituted azetidinones as anti-inflammatory and antidegenerative agents LV11459B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US17968888A 1988-04-11 1988-04-11

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LV11459A LV11459A (lv) 1996-08-20
LV11459B true LV11459B (en) 1996-12-20

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EP (1) EP0337549B1 (lv)
JP (1) JP2736113B2 (lv)
KR (1) KR930008223B1 (lv)
CN (1) CN1037144A (lv)
AT (1) ATE128704T1 (lv)
AU (1) AU621865B2 (lv)
CA (1) CA1337990C (lv)
DE (1) DE68924439T2 (lv)
DK (1) DK169329B1 (lv)
ES (1) ES2079373T3 (lv)
FI (1) FI891689A (lv)
GR (1) GR3017656T3 (lv)
HU (1) HUT50761A (lv)
IE (1) IE891140L (lv)
IL (1) IL89835A0 (lv)
LV (1) LV11459B (lv)
NO (1) NO891470L (lv)
NZ (1) NZ228600A (lv)
PT (1) PT90222B (lv)
YU (1) YU71489A (lv)
ZA (1) ZA892549B (lv)

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IL89835A0 (en) 1989-12-15
LV11459A (lv) 1996-08-20
NO891470L (no) 1989-10-12
EP0337549A1 (en) 1989-10-18
ATE128704T1 (de) 1995-10-15
CN1037144A (zh) 1989-11-15
DK170589A (da) 1989-10-12
FI891689A (fi) 1989-10-12
IE891140L (en) 1989-10-11
JPH026471A (ja) 1990-01-10
FI891689A0 (fi) 1989-04-10
AU621865B2 (en) 1992-03-26
ZA892549B (en) 1989-11-29
KR900016121A (ko) 1990-11-12
DE68924439D1 (de) 1995-11-09
GR3017656T3 (en) 1996-01-31
NO891470D0 (no) 1989-04-10
DE68924439T2 (de) 1996-05-09
EP0337549B1 (en) 1995-10-04
ES2079373T3 (es) 1996-01-16
DK169329B1 (da) 1994-10-10
NZ228600A (en) 1992-02-25
PT90222B (pt) 1994-07-29
PT90222A (pt) 1989-11-10
HUT50761A (en) 1990-03-28
DK170589D0 (da) 1989-04-10
JP2736113B2 (ja) 1998-04-02
CA1337990C (en) 1996-01-23
YU71489A (en) 1991-10-31
AU3263089A (en) 1989-10-12
KR930008223B1 (ko) 1993-08-27

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