LV10770B - Process for preparation of formoterol - Google Patents

Process for preparation of formoterol Download PDF

Info

Publication number
LV10770B
LV10770B LVP-93-1025A LV931025A LV10770B LV 10770 B LV10770 B LV 10770B LV 931025 A LV931025 A LV 931025A LV 10770 B LV10770 B LV 10770B
Authority
LV
Latvia
Prior art keywords
compound
branched
linear
alkyl
fumarate
Prior art date
Application number
LVP-93-1025A
Other languages
English (en)
Other versions
LV10770A (lv
Inventor
Trofast Jan William
Jakupovic Edib
Mansson Lena Katarina
Original Assignee
Astra Ab
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 Astra Ab filed Critical Astra Ab
Publication of LV10770A publication Critical patent/LV10770A/lv
Publication of LV10770B publication Critical patent/LV10770B/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
  • Steroid Compounds (AREA)

Claims (10)

  1. LV 10770 PATENTA FORMULA 1. Paņēmiens savienojuma ar formulu (I) 10
    NH CHO O -OCH 3 I kurā: R1 ir H vai lineāra vai sazarota C^-alkilgrupa; R 15 I A ir vai nu -N+-, kur R ir H vai lineāra vai sazarota C^-alkilgrupa un 20 R2 ir H vai lineāra vai sazarota C^-alkilgrupa; vai -NR-, kur R ir jau minētā nozīme; vai šī savienojuma farmaceitiski pieņemama fumarāta un/vai solvāta iegūšanai tīru racemātu vai četru izomēru maisījuma veidā, kas atšķiras ar to, ka: 25 a) savieno (II) ar (III)
    NO II III iegūstot (IV) 2 30 5 2 10
    b) reducē un pēc tam formilē savienojumu (IV), iegūstot savienojumu (V) 15
    20 v c) iegūst savienojuma (V) fumarātu un sadala racemātus, kristalizējot tos, 25 d) izdala savienojuma (V) vajadzīgā racemāta bāzi, e) hidrogenolizē savienojuma (V) minētās bāzes aizsargājošās benzilgrupas, iegūstot savienojumu (I), kurā A ir -NH- un R1 ir H, un neobligāti 30 f) iegūst savienojuma (I) fumarātu un/vai solvātu, un neobligāti R I g) kad A ir vai nu -N+-, kur R ir H vai lineāra vai sazarota C, 5-alkil- I R2 35 3 LV 10770 grupa un R2 ir H vai lineāra vai sazarota C^-alkilgrupa; vai -NR-, kur R lineāra vai sazarota C^-alkilgrupa un R1 nozīme ir jau minētā, alkilē stadijā e) vai f) iegūto produktu.
  2. 2. Paņēmiens pēc 1. punkta, kas atšķiras ar to, ka stadiju a) veic šķīdinātājā, tādā, kā zemākie spirti, pie atteces temperatūras vai bez šķīdinātāja vēlams pie temperatūras 80-120 °C.
  3. 3. Paņēmiens pēc 1. vai 2. punkta, kas atšķiras ar to, ka stadija b) ir 10 vienpakāpes reakcija ar Reneja niķeli un skudrskābi vai divpakāpju reakcija, kas ietver nitrogrupas katalītisku reducēšanu un tai sekojošu formilēšanu skudrskābes pārākumā.
  4. 4. Paņēmiens pēc jebkura no 1. līdz 3. punktiem, kas atšķiras ar to, ka 15 racemātu sadalīšana ar kristalizāciju stadijā c) tiek veikta šķīdinātāju sistēmā, kas sastāv no etilacetāta, izopropilacetāta un/vai metil-izobutilketona.
  5. 5. Paņēmiens pēc 4. punkta, kas atšķiras ar to, ka šķīdinātāju sistēma 20 papildus satur nelielus daudzumus šķīdinātāju, kas ir polārāki par 4. punktā minētajiem, piemēram, dimetilformamīds, dimetiisulfoksīds un/vai metanols.
  6. 6. Paņēmiens pēc 5. punkta, kas atšķiras ar to, ka polārākā šķīdinātāja daudzums ir vēlams mazāks par 15 %. 25
  7. 7. Paņēmiens pēc jebkura no 1. līdz 6. punktiem, kas atšķiras ar to, ka R ir ūdeņradis un R1 ir ūdeņradis.
  8. 8. Paņēmiens pēc jebkura no 1. līdz 6. punktiem, kas atšķiras ar to, ka R 30 un/vai R2 ir lineāras vai sazarotas C^-alkilgrupas.
  9. 9. Savienojums ar kopējo formulu (I) 35 5
    OH . VJ.„- (ļH3
    OCH. I kura: R1 ir H vai lineāra vai sazarota C15-alkilgrupa; R
  10. 10 I A ir vai nu -N+-, kur R ir H vai lineārā vai sazarota C^-alkilgrupa un R2 R2 ir H vai lineāra vai sazarota C^-alkilgrupa; vai -NR-, kur R ir jau minētā nozīme; vai šī savienojuma farmaceitiski pieņemams fumarāts un/vai solvāts tīru racemātu vai četru izomēru maisījuma veidā. 15
LVP-93-1025A 1990-09-26 1993-08-10 Process for preparation of formoterol LV10770B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9003057A SE9003057D0 (sv) 1990-09-26 1990-09-26 New process
PCT/SE1991/000643 WO1992005147A1 (en) 1990-09-26 1991-09-25 New process for preparing formoterol and related compounds

Publications (2)

Publication Number Publication Date
LV10770A LV10770A (lv) 1995-08-20
LV10770B true LV10770B (en) 1996-04-20

Family

ID=20380456

Family Applications (1)

Application Number Title Priority Date Filing Date
LVP-93-1025A LV10770B (en) 1990-09-26 1993-08-10 Process for preparation of formoterol

Country Status (28)

Country Link
EP (1) EP0550612B1 (lv)
JP (1) JP2801401B2 (lv)
KR (1) KR0179639B1 (lv)
AT (1) ATE134990T1 (lv)
AU (1) AU652386B2 (lv)
BG (1) BG61605B1 (lv)
CA (1) CA2091343C (lv)
CZ (1) CZ284256B6 (lv)
DE (1) DE69117768T2 (lv)
DK (1) DK0550612T3 (lv)
EE (1) EE02979B1 (lv)
ES (1) ES2084831T3 (lv)
FI (1) FI111714B (lv)
GR (1) GR3020134T3 (lv)
HK (1) HK52297A (lv)
HU (1) HU214054B (lv)
IE (1) IE74387B1 (lv)
IS (1) IS1684B (lv)
LT (1) LT3813B (lv)
LV (1) LV10770B (lv)
NO (1) NO301709B1 (lv)
PL (1) PL166434B1 (lv)
PT (1) PT99051B (lv)
RU (1) RU2079486C1 (lv)
SE (1) SE9003057D0 (lv)
SG (1) SG43150A1 (lv)
SK (1) SK22793A3 (lv)
WO (1) WO1992005147A1 (lv)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6299863B1 (en) 1992-04-03 2001-10-09 Sepracor Inc. Aerosol formulations containing micronized optically pure (R,R) formoterol for bronchodilating therapy
US6866839B2 (en) 1991-04-05 2005-03-15 Sepracor Inc. Methods and compositions for treating pulmonary disorders using optically pure (R,R)-formoterol
US5795564A (en) * 1991-04-05 1998-08-18 Sepracor, Inc. Methods and compositions for treating pulmonary disorders using optically pure (R,R)-formoterol
US5629200A (en) * 1993-11-18 1997-05-13 Daicel Chemical Industries, Ltd. Production of optically active 2-amino-1-phenylethanol derivatives by asymetrical assimilation
SE9404080L (sv) * 1993-12-28 1995-06-29 Ciba Geigy Ag Förfarande för framställning av en optiskt ren enantiomer av formoterol
AU722859B2 (en) * 1996-11-11 2000-08-10 Sepracor, Inc. Process for the preparation of optically pure isomers of formoterol
US6040344A (en) 1996-11-11 2000-03-21 Sepracor Inc. Formoterol process
US6303145B2 (en) 1999-05-10 2001-10-16 Sepracor Inc. (S,R) formoterol methods and compositions
AR028948A1 (es) 2000-06-20 2003-05-28 Astrazeneca Ab Compuestos novedosos
AU2002252950A1 (en) * 2001-02-22 2002-09-04 Universitatsklinikum Charite Medizinische Fakultat Der Humboldt-Universitat Zu Berlin Protein kinase d inhibitors and protein kinase 2 inhibitors as agents for inhibiting tumour cells and for stimulating angiogenesis
US6472563B1 (en) 2001-11-09 2002-10-29 Sepracor Inc. Formoterol tartrate process and polymorph
TWI359675B (en) 2003-07-10 2012-03-11 Dey L P Bronchodilating β-agonist compositions
TW200738634A (en) 2005-08-02 2007-10-16 Astrazeneca Ab New salt
WO2008035380A2 (en) * 2006-09-19 2008-03-27 Natco Pharma Limited An improved process for the preparation of high purity formoterol and its pharmaceutically acceptable salts
TW200825084A (en) 2006-11-14 2008-06-16 Astrazeneca Ab New compounds 521
JP2011501204A (ja) * 2007-10-29 2011-01-06 ジェネリクス・（ユーケー）・リミテッド 新規なクロマトグラフィー方法
EA017627B1 (ru) 2008-05-13 2013-01-30 Астразенека Аб Хинуклидиновые производные в качестве антагонистов мускаринового м3 рецептора
CN101921200B (zh) * 2009-06-16 2014-01-15 上海医药工业研究院 一种n-苄基-1-(4-甲氧基苯基)-2-丙胺的制备方法
WO2011061527A1 (en) 2009-11-17 2011-05-26 Astrazeneca Ab Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases
CN115368250B (zh) * 2022-09-02 2024-07-26 博诺康源(北京)药业科技有限公司 拆分福莫特罗手性中间体的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2366625C2 (lv) * 1972-02-05 1988-06-09 Yamanouchi Pharmaceutical Co., Ltd., Tokio/Tokyo, Jp
GB1468156A (en) * 1973-07-19 1977-03-23 Ici Ltd Phenylethylamine derivatives
ES2005492A6 (es) 1987-12-23 1989-03-01 Lasa Lab Procedimiento de obtencion de n-(2-hidroxi-5-(1-hidroxi-2((2- (4-metoxifenil)-1metiletil)amino)etil)fenil)foramida (i).

Also Published As

Publication number Publication date
IS1684B (is) 1998-02-24
CA2091343A1 (en) 1992-03-27
NO931058D0 (no) 1993-03-23
FI931333A0 (fi) 1993-03-25
CZ44293A3 (en) 1994-01-19
BG97576A (bg) 1994-03-31
HU9300867D0 (en) 1993-06-28
LT3813B (en) 1996-03-25
WO1992005147A1 (en) 1992-04-02
BG61605B1 (bg) 1998-01-30
IS3756A7 (is) 1992-03-27
GR3020134T3 (en) 1996-08-31
IE913373A1 (en) 1992-04-08
ATE134990T1 (de) 1996-03-15
ES2084831T3 (es) 1996-05-16
JP2801401B2 (ja) 1998-09-21
AU8652091A (en) 1992-04-15
LTIP1715A (en) 1995-07-25
LV10770A (lv) 1995-08-20
DE69117768T2 (de) 1996-08-29
SG43150A1 (en) 1997-10-17
DE69117768D1 (de) 1996-04-11
SK22793A3 (en) 1993-07-07
PT99051A (pt) 1992-08-31
AU652386B2 (en) 1994-08-25
EE02979B1 (et) 1997-04-15
PL166434B1 (pl) 1995-05-31
FI111714B (fi) 2003-09-15
KR0179639B1 (ko) 1999-05-15
JPH06501262A (ja) 1994-02-10
HK52297A (en) 1997-05-02
IE74387B1 (en) 1997-07-30
EP0550612B1 (en) 1996-03-06
SE9003057D0 (sv) 1990-09-26
HU214054B (en) 1997-12-29
FI931333A (fi) 1993-04-22
CA2091343C (en) 2002-07-09
DK0550612T3 (da) 1996-07-22
RU2079486C1 (ru) 1997-05-20
PT99051B (pt) 1999-02-26
CZ284256B6 (cs) 1998-10-14
EP0550612A1 (en) 1993-07-14
NO301709B1 (no) 1997-12-01
HUT65912A (en) 1994-07-28
NO931058L (no) 1993-03-23

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