GB2043636B - Pyrimido benzazepine derivatives - Google Patents

Pyrimido benzazepine derivatives

Info

Publication number
GB2043636B
GB2043636B GB8003910A GB8003910A GB2043636B GB 2043636 B GB2043636 B GB 2043636B GB 8003910 A GB8003910 A GB 8003910A GB 8003910 A GB8003910 A GB 8003910A GB 2043636 B GB2043636 B GB 2043636B
Authority
GB
United Kingdom
Prior art keywords
hydrogen
lower alkyl
hydroxy
group
pyrimido
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
GB8003910A
Other versions
GB2043636A (en
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 GB2043636A publication Critical patent/GB2043636A/en
Application granted granted Critical
Publication of GB2043636B publication Critical patent/GB2043636B/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • C07C309/64Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66Methanesulfonates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/63Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/67Preparation 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 isomerisation; by change of size of the carbon skeleton
    • C07C45/68Preparation 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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70Preparation 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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71Preparation 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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/34Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D223/00Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16Benzazepines; Hydrogenated benzazepines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/16Radicals substituted by halogen atoms or nitro radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Indole Compounds (AREA)

Abstract

Pyrimido-2-benzazepines of the formula <IMAGE> wherein A is one of the groups <IMAGE> R<1> is hydrogen, chlorine, bromine, lower alkyl, the group NR<4>R<5>, the group -CH2-CO-R<7>, the group -NH(CH2)mNR<8>R<9>, hydroxy, lower alkoxy, mercapto or lower alkyl mercapto, R<2> is hydrogen, amino or di-lower alkyl amino, R<3> is hydrogen, lower acyloxy or hydroxy, X is hydrogen, halogen, trifluoromethyl, ethyl alpha -hydroxy ethyl or acetyl, Y is hydrogen or halogen, R<4> and R<5> each are hydrogen or lower alkyl or, together complete a five to seven membered heterocyclic ring, R<7> is hydroxy, lower alkoxy or NR<8>R<9>, R<8> and R<9> each are hydrogen or lower alkyl, n is 0 or 1 and m is 1 to 7, with certain provisos, and pharmaceutically acceptable acid addition salts thereof, exhibit pharmacological utility as anxiolytics and sedatives.
GB8003910A 1979-02-07 1980-02-06 Pyrimido benzazepine derivatives Expired GB2043636B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US1011879A 1979-02-07 1979-02-07
US1670979A 1979-03-01 1979-03-01
CH51080 1980-01-22

Publications (2)

Publication Number Publication Date
GB2043636A GB2043636A (en) 1980-10-08
GB2043636B true GB2043636B (en) 1983-05-11

Family

ID=27172162

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8003910A Expired GB2043636B (en) 1979-02-07 1980-02-06 Pyrimido benzazepine derivatives

Country Status (26)

Country Link
EP (1) EP0014470B1 (en)
AT (1) ATE14225T1 (en)
AU (1) AU535233B2 (en)
CA (1) CA1138863A (en)
DD (1) DD149066A5 (en)
DE (2) DE3070847D1 (en)
ES (1) ES488311A0 (en)
FI (1) FI68832C (en)
FR (1) FR2450833A1 (en)
GB (1) GB2043636B (en)
HU (1) HU182662B (en)
IE (1) IE49630B1 (en)
IL (1) IL59316A (en)
IN (1) IN151574B (en)
IT (1) IT1140535B (en)
LU (1) LU82143A1 (en)
MC (1) MC1314A1 (en)
MT (1) MTP864B (en)
NL (1) NL8000715A (en)
NO (1) NO153138C (en)
NZ (1) NZ192803A (en)
PT (1) PT70794B (en)
RO (1) RO79168A (en)
SE (1) SE8000964L (en)
SU (1) SU1181547A3 (en)
YU (1) YU32380A (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK347781A (en) * 1980-08-05 1982-02-06 Hoffmann La Roche PROCEDURE FOR PREPARING PYRIMIDO- (4,5-D) (2) -BENZEZEPINS OR PHARMACEUTICAL ACCEPTABLE SALTS THEREOF
EP0273697A3 (en) * 1986-12-30 1989-11-29 Merck & Co. Inc. 2-benzazepines with 5- and 6- membered heterocyclic rings
US5013333A (en) * 1990-04-13 1991-05-07 Tennant Company Unattended air cleaning system for surface maintenance machine
JP5097539B2 (en) 2004-05-07 2012-12-12 アムジエン・インコーポレーテツド Protein kinase modulators and methods of use
JP4467616B2 (en) 2004-05-14 2010-05-26 ミレニアム・ファーマシューティカルズ・インコーポレイテッド Compounds and methods for blocking mitotic progression by inhibition of Aurora kinase
US7718648B2 (en) 2006-08-09 2010-05-18 Millennium Pharmaceuticals, Inc. Pyridobenzazepine compounds and methods for inhibiting mitotic progression
CL2007003244A1 (en) 2006-11-16 2008-04-04 Millennium Pharm Inc COMPOUNDS DERIVED FROM PIRIMIDO [5,4-D] [2] BENZAZEPINA; PHARMACEUTICAL COMPOSITION THAT INCLUDES SUCH COMPOUND; AND USE OF THE COMPOUND FOR THE TREATMENT OF CANCER.
RU2535032C2 (en) 2008-12-22 2014-12-10 Милленниум Фармасьютикалз, Инк. Combination of aurora kinase inhibitors and anti-cd20 antibodies
JO3635B1 (en) 2009-05-18 2020-08-27 Millennium Pharm Inc Solid pharmaceutical compositions and processes for their production
JP2013520424A (en) 2010-02-19 2013-06-06 ミレニアム ファーマシューティカルズ, インコーポレイテッド Sodium 4-{[9-chloro-7- (2-fluoro-6-methoxyphenyl) -5H-pyrimido [5,4-d] [2] benzoazepin-2-yl] amino} -2-methoxybenzoate Crystal form
US20130303519A1 (en) 2012-03-20 2013-11-14 Millennium Pharmaceuticals, Inc. Methods of treating cancer using aurora kinase inhibitors
CN105209042B (en) 2013-03-22 2019-03-08 米伦纽姆医药公司 The combination of 1/2 inhibitor of catalytic MTORC and selective aurora A kinase inhibitor

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947585A (en) * 1974-06-03 1976-03-30 Ciba-Geigy Corporation Pyrazolobenzazepines

Also Published As

Publication number Publication date
IE800227L (en) 1980-08-07
SU1181547A3 (en) 1985-09-23
IL59316A (en) 1983-07-31
FR2450833A1 (en) 1980-10-03
IE49630B1 (en) 1985-11-13
CA1138863A (en) 1983-01-04
RO79168A (en) 1982-06-25
DE3004381A1 (en) 1980-09-04
IN151574B (en) 1983-05-28
IL59316A0 (en) 1980-05-30
SE8000964L (en) 1980-08-08
NO800316L (en) 1980-08-08
ES8101590A1 (en) 1980-12-16
AU535233B2 (en) 1984-03-08
DD149066A5 (en) 1981-06-24
NO153138C (en) 1986-01-22
EP0014470A3 (en) 1982-02-10
PT70794B (en) 1981-06-11
DE3070847D1 (en) 1985-08-14
FR2450833B1 (en) 1983-06-10
GB2043636A (en) 1980-10-08
HU182662B (en) 1984-02-28
EP0014470B1 (en) 1985-07-10
IT1140535B (en) 1986-10-01
MC1314A1 (en) 1981-03-10
ES488311A0 (en) 1980-12-16
FI800367A (en) 1980-08-08
NO153138B (en) 1985-10-14
NZ192803A (en) 1984-08-24
FI68832C (en) 1985-11-11
PT70794A (en) 1980-03-01
EP0014470A2 (en) 1980-08-20
YU32380A (en) 1983-12-31
LU82143A1 (en) 1981-09-10
AU5529680A (en) 1980-08-14
ATE14225T1 (en) 1985-07-15
MTP864B (en) 1981-04-29
FI68832B (en) 1985-07-31
NL8000715A (en) 1980-08-11
IT8019740A0 (en) 1980-02-06

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Legal Events

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PCNP Patent ceased through non-payment of renewal fee