FI109995B - Förfarande för framställning av (2R)-metyl-4,4,4-trifluorbutylamin och (R)-4-[5-(N-[4,4,4-trifluor-2-metylbutyl]karbamoyl)-1-metylindol-3-ylmetyl]-3-metoxi-N-o-tolylsulfonylbentsamid - Google Patents

Förfarande för framställning av (2R)-metyl-4,4,4-trifluorbutylamin och (R)-4-[5-(N-[4,4,4-trifluor-2-metylbutyl]karbamoyl)-1-metylindol-3-ylmetyl]-3-metoxi-N-o-tolylsulfonylbentsamid Download PDF

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Publication number
FI109995B
FI109995B FI915721A FI915721A FI109995B FI 109995 B FI109995 B FI 109995B FI 915721 A FI915721 A FI 915721A FI 915721 A FI915721 A FI 915721A FI 109995 B FI109995 B FI 109995B
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FI
Finland
Prior art keywords
methyl
butyramide
trifluorobutylamine
diastereomeric
acid
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FI915721A
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English (en)
Finnish (fi)
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FI915721A (fi
FI915721A0 (fi
Inventor
Peter Robert Bernstein
Andrew George Brewster
Ying Kwong Yee
Robert Toms Jacobs
George Joseph Sependa
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Astrazeneca Ab
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Publication date
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Publication of FI915721A0 publication Critical patent/FI915721A0/fi
Publication of FI915721A publication Critical patent/FI915721A/fi
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Publication of FI109995B publication Critical patent/FI109995B/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/50—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of carboxylic acid amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • 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
    • A61P37/08—Antiallergic agents
    • 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
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/15—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom

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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)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pulmonology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Glass Compositions (AREA)
  • Iron Core Of Rotating Electric Machines (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (5)

1. Förfarande för framställning av (2R)-metyl-4,4,4-trifluorbutylamin eller dess syraadditionssalt, 5 kännetecknat därav, att a) man acylerar en optiskt aktiv amin, som är a-C-^ 6-alkylbensylamin, med 2-metyl-4,4,4-trifluorbutansyra eller ett reaktivt derivat därav, varvid man erhäller mot-svarande butyramid; 10 b) man separerar den (R)-diastereomera butyramiden frän den (S)-diastereomera butyramiden; och c) man omvandlar den (R)-diastereomera butyramiden tili den önskade (2R)-metyl-4,4,4-trifluorbutylaminen eller dess syraadditionssalt genom att reducera den tili 15 motsvarande amin, med formeln R1 20 F CH3 väri R1 är C^g-alkyl, varefter man utför hydrogenolys för :d25 att avlägsna a-C^.g-alkylbensylgruppen, varvid man erhäller (2R) -metyl-4,4,4-trifluorbutylamin. : 2. Förfarande enligt patentkrav 1, känne tecknat därav, att man behandlar den i steg b) er-hälinä (S)-diastereomera butyramiden med en stark bas och ."•30 den bildade butyramiden recykleras tillbaka tili steg b) .
3. Förfarande enligt patentkrav 2, kanne-tecknat därav, att den starka basen är en alkalime-tallalkoxid. ·;·· 4. Förfarande enligt nägot av patentkraven 1-3, .’.35 kännetecknat därav, att man separerar den (R) - 33 inoook diastereomera butyramiden frän den (S)-diastereomera bu-tyramiden genom kristallisering.
5. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man reducerar den (R)-diastere-5 omera butyramiden genom användning av boran. 6. 4,4,4-trifluor-2-metyl-N-[(S)-1-fenyletyl]butyr- amid. 7. (2R)-metyl-4,4,4-trifluorbutyl-[(S)-fenyletyl]- amin. 10 8. Förfarande för framställning av (R)-4-[5-(N- [4,4,4-trifluor-2-metylbutyl]karbamoyl)-l-metylindol-3-yl-metyl]-3-metoxi-N-o-tolylsulfonylbensamid med formeln CK /
15. CH3 OMe °
20. CH3 >t>; kännetecknat därav, att . . a) man acylerar en optiskt aktiv amin, som är α-Οχ_ ' 6-alkylbensylamin, med 2-metyl-4,4,4-trifluorbutansyra el- ler ett reaktivt derivat därav, varvid man erhäller mot- 4 t · !··25 svarande butyramid; • · b) man separerar den (R)-diastereomera butyramiden V : frän den (S)-diastereomera butyramiden; c) man omvandlar den (R)-diastereomera butyramiden :’\i tili den önskade (2R)-metyl-4,4,4-trifluorbutylaminen el- .’“30 ler dess syraadditionssalt genom att reducers den tili motsvarande amin, med formeln 34 1G999 b R1 5 fV'V'It^-O F CH3 10 väri R1 är C^g-alkyl, varefter man utför hydrogenolys för att avlägsna a-C^g-alkylbensylgruppen, varvid man erhäller (2R)-metyl-4,4,4-trifluorbutylamin; och d) man acylerar (2R)-metyl-4,4,4-trifluorbutylamin eller dess syraadditionssalt med en karboxylsyra, med for-15 meln CHa / OMe :° ipx JQ :··: s02 T . . O CH3 t 1 1 4 · ’·· väri U är karboxi, eller med ett reaktivt derivat därav. • 4
FI915721A 1990-12-05 1991-12-04 Förfarande för framställning av (2R)-metyl-4,4,4-trifluorbutylamin och (R)-4-[5-(N-[4,4,4-trifluor-2-metylbutyl]karbamoyl)-1-metylindol-3-ylmetyl]-3-metoxi-N-o-tolylsulfonylbentsamid FI109995B (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9026425 1990-12-05
GB909026425A GB9026425D0 (en) 1990-12-05 1990-12-05 Process

Publications (3)

Publication Number Publication Date
FI915721A0 FI915721A0 (fi) 1991-12-04
FI915721A FI915721A (fi) 1992-06-06
FI109995B true FI109995B (sv) 2002-11-15

Family

ID=10686507

Family Applications (1)

Application Number Title Priority Date Filing Date
FI915721A FI109995B (sv) 1990-12-05 1991-12-04 Förfarande för framställning av (2R)-metyl-4,4,4-trifluorbutylamin och (R)-4-[5-(N-[4,4,4-trifluor-2-metylbutyl]karbamoyl)-1-metylindol-3-ylmetyl]-3-metoxi-N-o-tolylsulfonylbentsamid

Country Status (20)

Country Link
US (1) US5274118A (sv)
EP (1) EP0489548B1 (sv)
JP (1) JP3160041B2 (sv)
AT (1) ATE115543T1 (sv)
AU (1) AU649498B2 (sv)
CA (1) CA2056068C (sv)
CZ (1) CZ281659B6 (sv)
DE (1) DE69105931T2 (sv)
DK (1) DK0489548T3 (sv)
ES (1) ES2066373T3 (sv)
FI (1) FI109995B (sv)
GB (1) GB9026425D0 (sv)
HU (1) HU212936B (sv)
IE (1) IE65663B1 (sv)
IL (1) IL100092A (sv)
NO (1) NO176516C (sv)
NZ (1) NZ240857A (sv)
PT (1) PT99684B (sv)
SK (1) SK280473B6 (sv)
ZA (1) ZA919572B (sv)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8927981D0 (en) * 1989-12-11 1990-02-14 Ici Plc Carbamoyl derivative
GB9026427D0 (en) * 1990-12-05 1991-01-23 Ici Plc Chemical process
GB9119001D0 (en) * 1991-09-05 1991-10-23 Ici Plc Pharmaceutical agents
JPWO2005005648A1 (ja) * 2003-07-11 2007-09-20 三菱ウェルファーマ株式会社 新規な光学活性カルボン酸の製造法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2243977A (en) * 1938-07-18 1941-06-03 Sandoz Ltd Process for the preparation of amino-alcohols
GB8927981D0 (en) * 1989-12-11 1990-02-14 Ici Plc Carbamoyl derivative
US5105014A (en) * 1991-08-06 1992-04-14 Mallinckrodt Medical, Inc. Synthesis of vicinal diamines

Also Published As

Publication number Publication date
CS368791A3 (en) 1992-09-16
DE69105931D1 (de) 1995-01-26
IL100092A (en) 1996-10-16
HU913758D0 (en) 1992-02-28
NO176516C (no) 1995-04-19
AU8838591A (en) 1992-06-11
ES2066373T3 (es) 1995-03-01
PT99684B (pt) 1999-05-31
DK0489548T3 (da) 1995-05-08
GB9026425D0 (en) 1991-01-23
FI915721A (fi) 1992-06-06
ZA919572B (en) 1992-10-28
AU649498B2 (en) 1994-05-26
PT99684A (pt) 1992-10-30
US5274118A (en) 1993-12-28
NO914776D0 (no) 1991-12-04
IE914219A1 (en) 1992-06-17
IL100092A0 (en) 1992-08-18
CZ281659B6 (cs) 1996-12-11
NZ240857A (en) 1994-05-26
CA2056068A1 (en) 1992-06-06
CA2056068C (en) 2003-05-06
IE65663B1 (en) 1995-11-15
JPH04290870A (ja) 1992-10-15
NO176516B (no) 1995-01-09
EP0489548A1 (en) 1992-06-10
ATE115543T1 (de) 1994-12-15
NO914776L (no) 1992-06-09
HU212936B (en) 1996-12-30
SK280473B6 (sk) 2000-02-14
EP0489548B1 (en) 1994-12-14
FI915721A0 (fi) 1991-12-04
JP3160041B2 (ja) 2001-04-23
DE69105931T2 (de) 1995-05-04
HUT61964A (en) 1993-03-29

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