SE8107017L - PROCEDURE FOR THE PREPARATION OF NEW BENZODIAZEPINES AND INTERMEDIATES - Google Patents

PROCEDURE FOR THE PREPARATION OF NEW BENZODIAZEPINES AND INTERMEDIATES

Info

Publication number
SE8107017L
SE8107017L SE8107017A SE8107017A SE8107017L SE 8107017 L SE8107017 L SE 8107017L SE 8107017 A SE8107017 A SE 8107017A SE 8107017 A SE8107017 A SE 8107017A SE 8107017 L SE8107017 L SE 8107017L
Authority
SE
Sweden
Prior art keywords
denotes
alkyl
preparation
compound
formula
Prior art date
Application number
SE8107017A
Other languages
Swedish (sv)
Other versions
SE435285B (en
Inventor
M Gall
Jr J B Hester
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of SE8107017L publication Critical patent/SE8107017L/en
Publication of SE435285B publication Critical patent/SE435285B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1454684 Benzophenones UPJOHN CO 7 Feb 1974 [14 Feb 1973] 23402/76 Divided out of 1454682 Heading C2C Benzophenones are prepared by the following route CR 1 = H, C 1-3 alkyl, Ph, PhCH 2 , C 2-4 alkoxycarbonyl; R 2-5 =H, halogen, CF 3 , CN, NO 2 , di(C 1-3 alkyl)amino, C 1-3 alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkanoylamino; X = activating atom or group; Ac= acetyl).

Claims (1)

PatentkravPatent claims 1. Forfarande fbr framstEllning av 6-feny1-4H-s-triacolon,3-a7C1,47benzodiazepin med formeln III dEr R, betecknar vdte, alkyl med 1-3 kolatcmer, fenyl, benzyl eller -COOR dEr R' betecknar 4101 med 1-3 koillomer och ddr R2, R3, R4 och R betecknar vdte,med 1-3 kolur, halogen, nitro, cyano, trifluormetyl, och alkcxi, alkyltio, alkylsulfinyl, alkylsulfonyl neb alkanoylamino eller dialkylamino dEr alkylgruppen rinnehAller 1-3 kolatomer,kInnetecknat me att en for ening med formeln I ddr Ri, 12, R3, R4 och 1 tidigare definierats, behandlas med en blandning av ftalimid och trifenylfosfin i ett inert vattenfritt organiskt losningsmedel med dietylazodikarboxylat mellan en temperatur av 0 och 100°C under en tidsperiod av 2-36 timmar, varefter blandningen extraheras och den pd sA Ott erhAllna ftalimidofbr- eningen med formeln IIN 11, ft 64 04aA, 0 R3 R2 I' dEr Ri, 12, R3, 14 och 1 tidigare definierats Och dEr A betecknar 0 utvinnes vareftlippreningen mellillmeln II behandlas i en alkanol med 1-3 kolatomed hydrazinhyvid en temperatur mellan 25- 100°C, varvid erhAlles en forening med formeln III.A process for the preparation of 6-phenyl-4H-s-triacolone, 3-α7C1,47benzodiazepine of formula III dEr, denotes hydrogen, alkyl of 1-3 carbon atoms, phenyl, benzyl or -COOR dEr R 'denotes 4101 of 1 -3 carbon isomers and ddr R2, R3, R4 and R represent hydrogen, having 1-3 carbons, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkanoylamino or dialkylamino. The alkyl group contains 1-3 carbon atoms, A compound of formula I wherein R 1, 12, R 3, R 4 and 1 are previously defined, treated with a mixture of phthalimide and triphenylphosphine in an inert anhydrous organic solvent with diethyl azodicarboxylate between a temperature of 0 and 100 ° C for a period of time of 2-36 hours, after which the mixture is extracted and the phthalimido compound obtained with the formula IIN 11, ft 64 04aA, 0 R3 R2 I 'where R 1, 12, R3, 14 and 1 are previously defined and where A denotes 0 is recovered. the intermediate II is treated in an alkanol with 1-3 k olatomed with hydrazine at a temperature between 25-100 ° C, whereby a compound of formula III is obtained.
SE8107017A 1973-02-14 1981-11-25 PROCEDURE FOR PREPARING 6-PHENYL-4H-S-TRIAZOLO (4,3-A) (1,4) BENZODIAZEPINES SE435285B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US33237773A 1973-02-14 1973-02-14

Publications (2)

Publication Number Publication Date
SE8107017L true SE8107017L (en) 1981-11-25
SE435285B SE435285B (en) 1984-09-17

Family

ID=23297958

Family Applications (2)

Application Number Title Priority Date Filing Date
SE7401858A SE423546B (en) 1973-02-14 1974-02-12 PROCEDURE FOR PREPARING 6-PHENYL-4H-S-TRIAZOLO (4,3-A) (1,4) BENZODIAZEPINES
SE8107017A SE435285B (en) 1973-02-14 1981-11-25 PROCEDURE FOR PREPARING 6-PHENYL-4H-S-TRIAZOLO (4,3-A) (1,4) BENZODIAZEPINES

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SE7401858A SE423546B (en) 1973-02-14 1974-02-12 PROCEDURE FOR PREPARING 6-PHENYL-4H-S-TRIAZOLO (4,3-A) (1,4) BENZODIAZEPINES

Country Status (16)

Country Link
JP (1) JPS49110699A (en)
AU (1) AU471038B2 (en)
BE (1) BE811025A (en)
CA (1) CA999000A (en)
CH (2) CH586704A5 (en)
DE (1) DE2402363A1 (en)
DK (1) DK140803B (en)
ES (2) ES422941A1 (en)
FR (1) FR2217335B1 (en)
GB (3) GB1454683A (en)
HU (1) HU168136B (en)
IL (3) IL49503A (en)
NL (1) NL7400958A (en)
PH (2) PH10784A (en)
SE (2) SE423546B (en)
ZA (1) ZA74466B (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3709898A (en) * 1971-02-09 1973-01-09 Upjohn Co Process for the production of triazolobenzodiazepines and intermediates

Also Published As

Publication number Publication date
CA999000A (en) 1976-10-26
ES422941A1 (en) 1976-09-16
AU6478674A (en) 1975-07-24
DK140803C (en) 1980-04-21
IL49503A0 (en) 1976-06-30
PH10784A (en) 1977-09-06
HU168136B (en) 1976-02-28
CH586704A5 (en) 1977-04-15
AU471038B2 (en) 1976-04-08
CH587263A5 (en) 1977-04-29
SE435285B (en) 1984-09-17
GB1454684A (en) 1976-11-03
GB1454682A (en) 1976-11-03
BE811025A (en) 1974-08-14
JPS49110699A (en) 1974-10-22
SE423546B (en) 1982-05-10
IL44068A (en) 1977-05-31
FR2217335A1 (en) 1974-09-06
DK140803B (en) 1979-11-19
DE2402363A1 (en) 1974-08-22
ZA74466B (en) 1974-12-24
IL49503A (en) 1977-05-31
IL44068A0 (en) 1974-05-16
ES445860A1 (en) 1977-05-01
NL7400958A (en) 1974-08-16
FR2217335B1 (en) 1977-06-10
PH11789A (en) 1978-07-05
GB1454683A (en) 1976-11-03

Similar Documents

Publication Publication Date Title
US5567844A (en) Process for preparing 1-phenyl-2-amino-3-fluoro-1-propanols
US4743700A (en) Process for fluorinating 1-phenyl-2-amino-1,3-propanediol compounds
DK599385D0 (en) PROCEDURE FOR THE PREPARATION OF AMID DERIVATIVES
US5508439A (en) Perfluoroalkanoyl aminonitriles
Krook et al. The direct cyclization of. alpha.-acylamino-substituted hydroxamates to. beta.-lactams
US5659046A (en) Method for the preparation of 2-perfluoroalkyl-3-oxazolin-5-one
CA1247626A (en) 2-(3,5-dialkyl-4-hydroxyphenyl)indole derivatives
SE8107017L (en) PROCEDURE FOR THE PREPARATION OF NEW BENZODIAZEPINES AND INTERMEDIATES
Smith N-DIENYL AMIDES AND LACTAMS: PREPARATION AND DIELS-ALDER REACTIVITY
AU612838B2 (en) Substituted-1-amino-2-cyano-3-phenyl-4-nitro-but-1-ene- derivatives as intermediates in herbicidal manufacture
Dandia et al. Montmorillonite catalysed synthesis of novel spiro [3H-indole-3, 3′-[3H-1, 2, 4] triazol]-2 (1H) ones in dry media under microwave irradiation
EA200100391A1 (en) NEW DERIVATIVES OF 6- (4-PHENYLBUTOXY) HEXYLAMINE AND METHOD OF OBTAINING SALMETEROL
US5243056A (en) Intermediates for the preparation of 1-(phenyl)-1-hydroxy-2-amino-3-fluoro propane derivatives
US4363918A (en) Method of preparing 1-alkyl-3-carboxy-1H pyrrole-2-acetic acids
Stevenson et al. Unprecedented regio and stereocontrol in Povarov reaction of benzylidene-(3-nitrophenyl) amine
JP3848382B2 (en) Process for the preparation of 2-perfluoroalkyl-3-oxazolin-5-one
CA1050556A (en) Aminopyrrole derivatives
Busson et al. Circular dichroism of monocyclic. beta.-lactams
CA1055036A (en) 3-amino-4-carbamyl-pyrrol derivatives and methods for their preparation
US5290947A (en) Process for the preparation of pyrrole derivates
Burlow Formal [4+ 2] Cycloadditions of Anhydrides and⍺, β-Unsaturated N-Tosyl Ketimines
US4075221A (en) Process for preparing triazolobenzodiazepines
Barnes et al. Synthesis of 2‐aryl‐3‐trifluoromethylsulfonylpyrroles
US4973696A (en) Stereoselective process for preparing optically active alpha, beta-disubstituted carbonyl compounds
Fuentes et al. Synthesis of heterocyclic compounds. XIII. 2‐amino‐3‐benzyl‐3, 5‐dieyano‐6‐methoxy‐4‐phenyl‐3, 4‐dihydropyridines

Legal Events

Date Code Title Description
NUG Patent has lapsed

Ref document number: 8107017-9

Effective date: 19930912

Format of ref document f/p: F