OA10025A - Crystallization of optical isomers of leukotriene antagonists - Google Patents

Crystallization of optical isomers of leukotriene antagonists Download PDF

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Publication number
OA10025A
OA10025A OA60521A OA60521A OA10025A OA 10025 A OA10025 A OA 10025A OA 60521 A OA60521 A OA 60521A OA 60521 A OA60521 A OA 60521A OA 10025 A OA10025 A OA 10025A
Authority
OA
OAPI
Prior art keywords
alkyl
alkoxy
phenyl
formula
acid
Prior art date
Application number
OA60521A
Other languages
English (en)
Inventor
Robert John Mills
Original Assignee
Smithkline Beecham Corp
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 Smithkline Beecham Corp filed Critical Smithkline Beecham Corp
Publication of OA10025A publication Critical patent/OA10025A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (10)

  1. Claims:
    1. A sait of formula 1 1 0025 R Z
    (A)
    (χ) (i) where: A is 1 and X is 1 or 2; Rl is Ce to C13 alkyl, C7 to C12 alkoxy, C7 to C12 alkylthio, Cio to Cio 1-alkynyl,10-undecynyloxy, 11-dodecynyl, phenyl-C4 to Cio alkyl, phenyl-C3 to C9 alkoxy,phcnylthio-C3 to C9 alkyl with the phenyl optionally mono substituted with bromo, chloro,trifluoromethyl, Ci to C4 alkoxy, methylthio or trifluoromethylthio, furyl-Gj to Cio alkyl,trifluoromethyl-07 to C12 alkyl or cyclohexyI-C4 to Cio alkyl; q is 0,1 or 2, with the proviso that Rj is not alkylthio or phenylthioalkyl when q is 1 or 2; Y is (CH2)mCOR3, or (CH2)m-tetrazol-5-yl; R3 is O', amino, or Ci to Cg alkoxy,m is 0, 1, or 2; R is (CH2)nCOR6;n is 0 to 6; Rg is O-, amino, or Ci to Cô-alkoxy; with the proviso that at least one of Y or R must hâve an R3 or R^ group respectivelywhich is O*.
  2. 2. A sait of.claim 1 represented by formula (IA).
    (A) w (IA) where Ri is phenylalkyl.
  3. 3. A sait of claim 2 where R is (CH2) 1-3 CORô- 7 1 0025
  4. 4. A sait of claim 3 rcpresented by the 3-arylpropionate of formula (IB) wherc X is 2 z(CH2)2C(O)O· CH2C(O)O- (1)
    J w (IB)
  5. 5. A sait of claim 4 where Ri is phenyl-C4 to Cio alkyl.
  6. 6. A sait of claim 5 which is the bis-(S)-a-rnethylbenzenemethanamine sait of (S)-b-[(2-carboxyethyl)thio]-2-(8-phenyloctyl)benzenepropanoic acid.
  7. 7. A process for separating a single isomer from a racemic mixture of acompound of formula Π
    where: 1 5 Ri is C8 to C13 alkyl, C7 to C12 alkoxy, C7 to C12 alkylthio, Cio to C12 1-alkynyl, 10-undecynyloxy, 11-dodecynyl, phenyl-C4 to Cio alkyl, phenyl-Cs to C9 alkoxy,phenylthio-C3 to C9 alkyl with the phenyl optionally mono substituted with bromo, chloro,trifluoromethyl, Ci to C4 alkoxy, methylthio or trifluoromethylthio, furyl-C4 to Cio alkyl,trifluoromethyl-C7 to C12 alkyl or cyclohexyl-Gj to Cio alkyl; 2 0 q is 0,1 or 2, with the proviso that Ri is not alkylthio or phenylthioalkyl when q is 1 or 2; Y is (CH2)mCOR3-, or (CH2)m-tetrazol-5-yl; R3' is OH, amino, or Ci to Cé alkoxy,m is 0, 1, or 2; 2 5 R is (CH2)nCOR6'; n is 0 to 6; R<5' is OH, amino, or Ci to Cg-alkoxy; with the proviso that at least one of R3- or Rtf is -OH or a sait thereof, which processcomprises: 1 0025 (i) . treating a racemic mixture of formula II with between about 0.5 to 1.5équivalents, relative to the number of carboxylic acid groups in formula (Π), of (S)-a-methylbenzenemethanamine; (ii) . recovering a crystalline sait; and (iii) . converting the sait to an acid or a pharmaceutically acceptable sait.
  8. 8. The process of claim 7 where the separated isomer is a compound of formuk:
    10
  9. 9. The process of claim 8 where Ri is a phenyl-C4 to Cio-alkyl.
  10. 10. The process of claim 9 wherein the isomer is (S)-b-[(2-carboxyethyl)thio]-2-(l-dodecyl)benzenepropanoic acid, or (S)-b-[(2-carboxyethyl)thio]-2-(8-phenyloctyl)benzenepropanoic acid.
OA60521A 1991-12-12 1994-06-07 Crystallization of optical isomers of leukotriene antagonists OA10025A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/806,031 US5214201A (en) 1991-12-12 1991-12-12 Crystallization of optical isomers of leukotriene antagonists

Publications (1)

Publication Number Publication Date
OA10025A true OA10025A (en) 1996-10-14

Family

ID=25193150

Family Applications (1)

Application Number Title Priority Date Filing Date
OA60521A OA10025A (en) 1991-12-12 1994-06-07 Crystallization of optical isomers of leukotriene antagonists

Country Status (21)

Country Link
US (1) US5214201A (fr)
EP (1) EP0638055A1 (fr)
JP (1) JPH07501823A (fr)
CN (1) CN1074212A (fr)
AP (1) AP371A (fr)
AU (1) AU3243993A (fr)
BG (1) BG98842A (fr)
BR (1) BR9207022A (fr)
CA (1) CA2125495A1 (fr)
CZ (1) CZ141294A3 (fr)
FI (1) FI942746A0 (fr)
HU (1) HUT70850A (fr)
IL (1) IL104077A0 (fr)
MA (1) MA22742A1 (fr)
MX (1) MX9207252A (fr)
NO (1) NO942187D0 (fr)
OA (1) OA10025A (fr)
SI (1) SI9200386A (fr)
SK (1) SK69094A3 (fr)
WO (1) WO1993012054A1 (fr)
ZA (1) ZA929677B (fr)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4845272A (en) * 1987-07-10 1989-07-04 Kuraray Co., Ltd. Process for the optical resolution of (±)-cis or (±)-trans-permethric acid
IT1217988B (it) * 1988-01-28 1990-03-30 Ind Chimica Profarmaco Spa Procedimento per la risoluzione ottica di un pacemo
US4904822A (en) * 1988-02-19 1990-02-27 Kuraray Co., Ltd. Process for the optical resolution of (+)-2-hydroxy-4-phenylbutanoic acid
IT1226300B (it) * 1988-07-26 1990-12-27 Zambon Spa Processo per la preparazione di intermedi per la sintesi del diltiazem.
CA2018437A1 (fr) * 1989-06-14 1990-12-14 James Simpson Frazee Antagonistes des leukotrienes

Also Published As

Publication number Publication date
JPH07501823A (ja) 1995-02-23
CA2125495A1 (fr) 1993-06-24
NO942187L (fr) 1994-06-10
HUT70850A (en) 1995-11-28
FI942746L (fi) 1994-06-10
WO1993012054A1 (fr) 1993-06-24
MA22742A1 (fr) 1993-07-01
AP9200462A0 (en) 1993-01-31
CN1074212A (zh) 1993-07-14
HU9401744D0 (en) 1994-09-28
US5214201A (en) 1993-05-25
BR9207022A (pt) 1995-12-12
BG98842A (bg) 1995-05-31
CZ141294A3 (en) 1995-01-18
IL104077A0 (en) 1993-05-13
EP0638055A4 (fr) 1994-10-19
SI9200386A (en) 1993-06-30
FI942746A7 (fi) 1994-06-10
AP371A (en) 1994-11-10
FI942746A0 (fi) 1994-06-10
MX9207252A (es) 1993-07-01
EP0638055A1 (fr) 1995-02-15
ZA929677B (en) 1993-10-13
SK69094A3 (en) 1995-03-08
NO942187D0 (no) 1994-06-10
AU3243993A (en) 1993-07-19

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