GB1449388A - Hydrocinnamic acid nitriles - Google Patents

Hydrocinnamic acid nitriles

Info

Publication number
GB1449388A
GB1449388A GB539776A GB539776A GB1449388A GB 1449388 A GB1449388 A GB 1449388A GB 539776 A GB539776 A GB 539776A GB 539776 A GB539776 A GB 539776A GB 1449388 A GB1449388 A GB 1449388A
Authority
GB
United Kingdom
Prior art keywords
acid
dimethoxy
methylsulphonylmethyl
chloro
reaction
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.)
Expired
Application number
GB539776A
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
Priority claimed from CH1568073A external-priority patent/CH591457A5/de
Priority claimed from CH1424374A external-priority patent/CH605827A5/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1449388A publication Critical patent/GB1449388A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms 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 the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • 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
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oncology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1449388 Hydrocinnamic acid nitriles F HOFFMAN-LA ROCHE & CO AG 8 Nov 1974 [8 Nov 1973 (2)] 05397/76 Divided out of 1449387 Heading C2C Novel compounds of Formula I wherein R<SP>1</SP> and R<SP>2</SP> are C 1-3 alkyl, R<SP>3</SP> is halogen and R<SP>5</SP> is an ether group a thioether group or an amino group derived from a primary or secondary amine are prepared by reaction of an appropriate benzaldehyde with a suitable propionitrile or by reaction of an α-(methylsulphonylmethyl)-benzyl alcohol with a suitable propionitrile. 4 - Chloro 3, - 5 - dimethoxy - α - (methylsulphonylmethyl) - benzyl alcohol is prepared by reduction od 41 - chloro - 3<SP>1</SP>,5<SP>1</SP> - dimethoxy- 2-methyl sulphonyl acetophenone which is obtained by reaction of dimethylsulphone and ethyl 4 - chloro - 3,5 - dimethyoxybenzoate obtained by esterification of the acid. The benzaldehydes intermediates and obtained either from the corresponding acid chlorides or α - (methylsulphonylmethyl) benzyl alcohols. Intermediates prepared in preparation of above starting materials are the acid chlorides 3 - hydroxy - 5 - keto - 4 - phenylazo - 3 - cyclohexene carboxylic acid and its methyl ester, 3,5- dihydroxy - 4 - phenylazobenzoic acid, 3,5 - dimethoxy - 4 - phenylazobenzoic acid methyl ester, 4 - amino - 3,5 - dimethoxybenzoic acid methyl ester, 4<SP>1</SP> - amino - 3<SP>1</SP>,5<SP>1</SP> - dimethoxy- 2 - methylsulphonylacetophenone and 3,5- dimethoxy-4-iodobenzaldehyde.
GB539776A 1973-11-08 1974-11-08 Hydrocinnamic acid nitriles Expired GB1449388A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US41403073A 1973-11-08 1973-11-08
CH1568073A CH591457A5 (en) 1973-11-08 1973-11-08
CH1424374A CH605827A5 (en) 1973-11-08 1974-10-24 2,4-diamino-5-(3,5-dialkoxy-4-halo-benzyl)-pyrimidines

Publications (1)

Publication Number Publication Date
GB1449388A true GB1449388A (en) 1976-09-15

Family

ID=27177143

Family Applications (2)

Application Number Title Priority Date Filing Date
GB539776A Expired GB1449388A (en) 1973-11-08 1974-11-08 Hydrocinnamic acid nitriles
GB4842574A Expired GB1449387A (en) 1973-11-08 1974-11-08 Benzylpyrimidine derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB4842574A Expired GB1449387A (en) 1973-11-08 1974-11-08 Benzylpyrimidine derivatives

Country Status (9)

Country Link
JP (1) JPS6119628B2 (en)
AT (1) AT342597B (en)
CA (1) CA1017743A (en)
DE (1) DE2452889C2 (en)
DK (1) DK136470B (en)
FR (1) FR2250533B1 (en)
GB (2) GB1449388A (en)
NL (1) NL184619C (en)
SE (1) SE419444B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2360299B (en) * 2000-03-01 2004-09-29 Portakabin Ltd Prefabricated building unit with fascia system

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR71725B (en) * 1977-11-10 1983-06-22 Hoffmann La Roche
DE2910510A1 (en) * 1979-03-16 1980-09-25 Heumann Ludwig & Co Gmbh 2,4-Di:amino-5-benzyl pyrimidine derivs. - are antibacterial cpds., prepd. by acylation of a 2,4-di:amino-5-(4'-hydroxy-benzyl) -pyrimidine cpd.
ZW10681A1 (en) * 1980-06-26 1982-02-24 Hoffmann La Roche Antibacterial agents
CH651473A5 (en) * 1982-07-29 1985-09-30 Joachim Karl Prof Dr Seydel PHARMACEUTICAL PREPARATION.
HU188588B (en) * 1982-08-13 1986-04-28 Egyt Gyogyszervegyeszeti Gyar Process for the production of 2,4-diamino-5-benzyl-pyrimidine-derivatives
IT1212907B (en) * 1983-12-21 1989-11-30 Romeo Aurelio PREPARATION OF HALOGENATED PHENOLS

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1103931B (en) * 1957-02-21 1961-04-06 Wellcome Found Process for the preparation of 2,4-diamino-5-benzylpyrimidine derivatives
US3485840A (en) * 1964-11-12 1969-12-23 Hoffmann La Roche 2,4-diamino - 5 - (2',4',5'-substituted benzyl) pyrimidines,intermediates and processes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2360299B (en) * 2000-03-01 2004-09-29 Portakabin Ltd Prefabricated building unit with fascia system

Also Published As

Publication number Publication date
AU7510574A (en) 1976-05-13
JPS6119628B2 (en) 1986-05-17
CA1017743A (en) 1977-09-20
FR2250533A1 (en) 1975-06-06
DE2452889A1 (en) 1975-05-15
SE7413958L (en) 1975-05-09
DE2452889C2 (en) 1985-09-19
NL7414528A (en) 1975-05-12
DK579374A (en) 1975-07-07
NL184619C (en) 1989-09-18
AT342597B (en) 1978-04-10
DK136470C (en) 1978-03-20
JPS5077378A (en) 1975-06-24
SE419444B (en) 1981-08-03
FR2250533B1 (en) 1978-07-21
DK136470B (en) 1977-10-17
NL184619B (en) 1989-04-17
GB1449387A (en) 1976-09-15
ATA892374A (en) 1977-08-15

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Legal Events

Date Code Title Description
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
PS Patent sealed [section 19, patents act 1949]
SP Amendment (slips) printed
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19941107