CA2310714A1 - Process for preparing neuraminidase inhibitor ro-64-0796 - Google Patents

Process for preparing neuraminidase inhibitor ro-64-0796 Download PDF

Info

Publication number
CA2310714A1
CA2310714A1 CA002310714A CA2310714A CA2310714A1 CA 2310714 A1 CA2310714 A1 CA 2310714A1 CA 002310714 A CA002310714 A CA 002310714A CA 2310714 A CA2310714 A CA 2310714A CA 2310714 A1 CA2310714 A1 CA 2310714A1
Authority
CA
Canada
Prior art keywords
neuraminidase inhibitor
formula
preparing
preparing neuraminidase
meaning given
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002310714A
Other languages
French (fr)
Other versions
CA2310714C (en
Inventor
Martin Karpf
Rene Trussardi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of CA2310714A1 publication Critical patent/CA2310714A1/en
Application granted granted Critical
Publication of CA2310714C publication Critical patent/CA2310714C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • 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
    • C07C233/45—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 carboxyl groups
    • C07C233/52—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C317/50—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Abstract

The invention provides a multistep process for preparing 1,2-diamino compounds of formula (SEE FORMULA I) wherein R1, R1', R2, R2', R3 and R4 have the meaning given in the specification and pharmaceutically acceptable addition salts thereof, from 1,2-epoxides of formula (SEE FORMULA II) wherein R1, R1', R2 and R2' have the meaning given in the specification.
CA002310714A 1999-06-11 2000-06-06 Process for preparing neuraminidase inhibitor ro-64-0796 Expired - Lifetime CA2310714C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP99111418.2 1999-06-11
EP99111418 1999-06-11
EP00103588.0 2000-02-21
EP00103588 2000-02-21

Publications (2)

Publication Number Publication Date
CA2310714A1 true CA2310714A1 (en) 2000-12-11
CA2310714C CA2310714C (en) 2008-08-19

Family

ID=26070572

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002310714A Expired - Lifetime CA2310714C (en) 1999-06-11 2000-06-06 Process for preparing neuraminidase inhibitor ro-64-0796

Country Status (10)

Country Link
US (2) US6437171B1 (en)
EP (1) EP1059283B1 (en)
JP (1) JP4656696B2 (en)
KR (1) KR100679780B1 (en)
CN (1) CN1191230C (en)
AT (1) ATE241589T1 (en)
CA (1) CA2310714C (en)
DE (1) DE60002949T2 (en)
DK (1) DK1059283T3 (en)
ES (1) ES2198244T3 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2198244T3 (en) * 1999-06-11 2004-02-01 F. Hoffmann-La Roche Ag PROCEDURE FOR PREPARATION OF RO-64-0796 INHIBITOR OF NEURAMINIDASA.
JP2001131144A (en) * 1999-11-02 2001-05-15 Sagami Chem Res Center Method for producing 7-azabicyclo[4.1.0]hept-3-ene-3- carboxylate compounds
US6518048B2 (en) * 2000-04-10 2003-02-11 Hoffmann-La Roche Inc. Stereo-specific synthesis of shimikic acid derivatives with improved efficiency
GB0202563D0 (en) * 2002-02-04 2002-03-20 Glaxo Group Ltd Process
US7122684B2 (en) 2003-03-13 2006-10-17 Roche Colorado Corporation Process for preparing 1,2-diamino compounds
US7875730B2 (en) 2004-02-23 2011-01-25 Cadila Healthcare Ltd. Process for manufacture of racemic Carvedilol
ATE473960T1 (en) * 2004-09-02 2010-07-15 Hoffmann La Roche METHOD FOR PRODUCING 4,5-DIAMINO-SHIKIMIC ACID
KR100819759B1 (en) * 2005-12-01 2008-04-07 (주)파인켐 Synthetic process of 1,2-diamino compounds without any explosion of azide compounds
WO2008028057A2 (en) * 2006-08-30 2008-03-06 President And Fellows Of Harvard College Shikimic acid-derived compounds for inhibition and detection of aurora a-associated tumors
JP5698128B2 (en) * 2009-06-09 2015-04-08 国立大学法人 岡山大学 Dihydroxyhexenoic acid ester and method for producing the same
JP4496351B1 (en) * 2009-09-01 2010-07-07 国立大学法人 岡山大学 1,3-dioxolane compound and method for producing the same
CN113024396B (en) * 2019-12-25 2024-01-30 上海奥博生物医药股份有限公司 Preparation method of oseltamivir and intermediate thereof
CN111153818B (en) * 2020-03-13 2023-03-28 遂成药业股份有限公司 Method for preparing antiviral drug Tamiflu intermediate tert-butylamine derivative I
CN111499536B (en) * 2020-05-06 2022-10-18 湖南欧亚药业有限公司 Preparation method of oseltamivir

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1593775A1 (en) * 1967-04-13 1971-03-25 Basf Ag Process for the production of 1,2-diamines
JPS57144247A (en) * 1981-03-02 1982-09-06 Lion Corp Preparation of n-substituted amino-alcohol compound
JPH04368356A (en) * 1991-06-12 1992-12-21 Nitto Denko Corp Production of n,n-dimethyl-3-amino-2-methyl-2-propanol
US5866601A (en) 1995-02-27 1999-02-02 Gilead Sciences, Inc. Carbocyclic compounds
DK0759917T3 (en) 1995-02-27 2000-07-31 Gilead Sciences Inc Novel selective inhibitors of viral or bacterial neuraminidases
US5763483A (en) 1995-12-29 1998-06-09 Gilead Sciences, Inc. Carbocyclic compounds
US6518438B2 (en) * 1996-08-23 2003-02-11 Gilead Sciences, Inc. Preparation of cyclohexene carboxylate derivatives
DE69711395T2 (en) * 1996-08-23 2002-11-07 Gilead Sciences Inc METHOD FOR PRODUCING CYCLOHEXEN-CARBOXYLATE DERIVATIVES
US5859284A (en) 1996-08-23 1999-01-12 Gilead Sciences, Inc. Preparation of carbocyclic compounds
US5994377A (en) 1996-10-21 1999-11-30 Gilead Sciences, Inc. Piperidine compounds
JPH10251190A (en) * 1997-03-11 1998-09-22 Sumitomo Chem Co Ltd Aromatic ketone compound, its production and intermediate thereof
US5886213A (en) 1997-08-22 1999-03-23 Gilead Sciences, Inc. Preparation of carbocyclic compounds
IL134691A0 (en) * 1997-09-17 2001-04-30 Gilead Sciences Inc Compounds containing six-membered rings, processes for their preparation, and their use as medicaments
JP3075558B2 (en) * 1998-01-16 2000-08-14 日本たばこ産業株式会社 Method for producing optically active amino alcohols
ES2198244T3 (en) * 1999-06-11 2004-02-01 F. Hoffmann-La Roche Ag PROCEDURE FOR PREPARATION OF RO-64-0796 INHIBITOR OF NEURAMINIDASA.

Also Published As

Publication number Publication date
US6437171B1 (en) 2002-08-20
CN1277957A (en) 2000-12-27
ES2198244T3 (en) 2004-02-01
CA2310714C (en) 2008-08-19
JP2001031631A (en) 2001-02-06
JP4656696B2 (en) 2011-03-23
DE60002949D1 (en) 2003-07-03
EP1059283B1 (en) 2003-05-28
EP1059283A1 (en) 2000-12-13
ATE241589T1 (en) 2003-06-15
DE60002949T2 (en) 2004-05-19
CN1191230C (en) 2005-03-02
KR100679780B1 (en) 2007-02-07
DK1059283T3 (en) 2003-09-15
US6939986B2 (en) 2005-09-06
KR20010049507A (en) 2001-06-15
US20020095040A1 (en) 2002-07-18

Similar Documents

Publication Publication Date Title
MXPA05009668A (en) Azide free process for preparing 1,2-diamino compounds.
CA2445306A1 (en) Process for preparing 4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives
DE69831868D1 (en) Antithrombosemittel
CA2310714A1 (en) Process for preparing neuraminidase inhibitor ro-64-0796
HU9602466D0 (en) Naphthalene derivatives as prostaglandin i2 agonits
WO2003082808A1 (en) Benzamide derivatives
IL133623A0 (en) Antithrombotic agents
CA2373117A1 (en) 13-methyl-erythromycin derivatives
GEP20074045B (en) (4-phenyl) piperidin-3-yl-phenylcarboxylate derivatives and related compounds as beta-secretase inhibitors for the treatment of alzheimer's disease
WO2003053971A8 (en) Pyridoquinoxaline antivirals
WO2001010860A3 (en) Quinazolinone and azaquinazolinone derivatives
WO2001030782A3 (en) Novel herbicides
EP1043311A4 (en) Biphenylamidine derivatives
EP1026162A4 (en) Antirheumatic
HRP20010885B1 (en) Ethanesulfonyl-piperidine derivatives
WO2001017959A3 (en) Vitronectin receptor antagonists
WO2004048381A3 (en) Pyrazoloazepine compounds as pharmaceutical agents
EP1074539A3 (en) Process for producing optically active 3,3,3,-trifluoro-2-hydroxy-2-methylpropionic acid, and salt thereof
SE9704770D0 (en) New use
JO2301B1 (en) Process for preparing Neuraminidase inhibitor RO-64-0796
EP0900796A4 (en) Preventives and remedies for ischemic intestinal lesion and ileus
AU2356501A (en) Bis-basic compounds for use as tryptase inhibitors, method for producing the same and their use as medicaments
CA2245484A1 (en) Novel urea derivatives
CA2340343A1 (en) Enantioselective synthesis
BG105999A (en) Treatment of osteoarthritis

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20200606