FI81578B - Foerfarande foer framstaellning av nya fosfodiesterasinhibierande 1,2,3,5-tetrahydroimidazo/2,1-b/ kinazolinderivat. - Google Patents

Foerfarande foer framstaellning av nya fosfodiesterasinhibierande 1,2,3,5-tetrahydroimidazo/2,1-b/ kinazolinderivat. Download PDF

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Publication number
FI81578B
FI81578B FI850618A FI850618A FI81578B FI 81578 B FI81578 B FI 81578B FI 850618 A FI850618 A FI 850618A FI 850618 A FI850618 A FI 850618A FI 81578 B FI81578 B FI 81578B
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FI
Finland
Prior art keywords
formula
acid
tetrahydroimidazo
compound
compounds
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Application number
FI850618A
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English (en)
Finnish (fi)
Other versions
FI850618A0 (fi
FI81578C (sv
FI850618L (fi
Inventor
John Hans Fried
Michael Charles Venuti
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Syntex Inc
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Publication date
Application filed by Syntex Inc filed Critical Syntex Inc
Publication of FI850618A0 publication Critical patent/FI850618A0/fi
Publication of FI850618L publication Critical patent/FI850618L/fi
Application granted granted Critical
Publication of FI81578B publication Critical patent/FI81578B/fi
Publication of FI81578C publication Critical patent/FI81578C/sv

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton

Claims (4)

1. Förfarande för framställning av nya fosfodies-terasinhibierande 1,2,3,5-tetrahydroimidazo[2,1-b]kina- 5 zollnderlvat med formeln I och farmaceutlskt godtagbara salter därav, (CH,)COZ i m
10 R5-NCO(CH2)nO H il (I) Y A 15 i vilken formal m och n är hei tai 1-6, R5 är cykloalkyl med 3-8 kolatomer, Y är väte, alkyl med 1-4 kolatomer, halogen eller lägre alkoxi och Z är -OR, eller -NR7R8, varvid R7 och Rb betecknar oberoende av varandra väte eller lägre alkyl, 20 kännetecknat därav, att a) en förenlng med formeln (CH0) COZ | z m
25 R5-NCO(CH2)nO Rl* - H (IV) Nir xoor6 y 2 30 där m, n, R5 och Y betecknar samma som ovan, Z är -0R7, där R7 är lägre alkyl, eller -NR,Re, där R7 och Re betecknar väte eller lägre alkyl, och R6 är alkyl med 1-6 kolatomer, behandlas i följd med en cyanhalogenid och en bas, eller 35 b) en förenlng med formeln 34 81 578 HOOC(CH2) O „ H H P-A>° Y i H 10 där m och Y betecknar sanuna som ovan, behandlas med ett amidbildande reagens med formeln HNiR^CHj^COZ, där m, R5 och Z betecknar sanuna som ovan; och, om sä önskas, c) behandlas en förening med formeln 15 (ch2)jbcoz -'"'igi®- .....
20. I H där m, n, R5 och Y betecknar samma som ovan och Z är -0R7, där R7 är lägre alkyl, med en bas, varvld erhälls en före- 25 nlng med formeln I, där Z är OH, eller d) omvandlas en fri syra med formeln I tili mot-svarande amid, eller e) omvandlas en fri syra med formeln I tili ett farmaseutiskt godtagbart sait, eller 30 f) omvandlas ett sait av en förening med formeln I tili motsvarande fria syra, eller g) omvandlas en fri bas med formeln I tili ett farmaseutiskt godtagbart syraadditionssalt, eller h) omvandlas ett sait av en förening med formeln 1 35 tili motsvarande fria bas. li 35 81 578
2. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att man framställer metyl-2-[N-cyk-lohexyl-4- (2-oxo-1,2,3,5-tetrahydroimidazo [2,1 -b] kinazo-lin-7-yl)oxibutyramidyl]acetat eller ett farmaceutiskt 5 godtagbart sait därav.
3. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer 2-[N-cyklohexyl- 4-(2-oxo-l,2,3,5-tetrahydrolmidazo[2,l-b]klnazolln-7-yl)-oxibutyramidyl]ättiksyra eller ett farmaceutiskt godtag- 10 bart sait därav.
4. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer 2-[N-cyklohexyl-4-(2-oxo-l,2,3,5-tetrahydroimidazo[2,l-b]kinazolin-7-yl )-oxibutyramidyl)acetamid eller ett farmaceutiskt godtagbart 15 sait därav.
FI850618A 1984-02-15 1985-02-14 Förfarande för framställning av nya fosfodiesterasinhibierande 1,2,3,5 -tetrahydroimidazo/2,1-b/kinazolinderivat FI81578C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58040984A 1984-02-15 1984-02-15
US58040984 1984-02-15

Publications (4)

Publication Number Publication Date
FI850618A0 FI850618A0 (fi) 1985-02-14
FI850618L FI850618L (fi) 1985-08-16
FI81578B true FI81578B (fi) 1990-07-31
FI81578C FI81578C (sv) 1990-11-12

Family

ID=24320992

Family Applications (1)

Application Number Title Priority Date Filing Date
FI850618A FI81578C (sv) 1984-02-15 1985-02-14 Förfarande för framställning av nya fosfodiesterasinhibierande 1,2,3,5 -tetrahydroimidazo/2,1-b/kinazolinderivat

Country Status (13)

Country Link
US (1) US4690925A (sv)
EP (1) EP0153152A3 (sv)
JP (1) JPS60193991A (sv)
AU (1) AU581205B2 (sv)
CA (1) CA1254557A (sv)
DK (1) DK69285A (sv)
ES (2) ES8607299A1 (sv)
FI (1) FI81578C (sv)
HU (2) HU191316B (sv)
IL (1) IL74349A (sv)
NO (1) NO164654C (sv)
NZ (1) NZ211117A (sv)
ZA (1) ZA851131B (sv)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4490371A (en) * 1983-02-16 1984-12-25 Syntex (U.S.A.) Inc. N,N-Disubstituted-(2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-B]quinazolinyl)oxyalkylamides
ZA851131B (en) * 1984-02-15 1986-09-24 Syntex Inc (2-oxo-1,2,3,5-tetrahydroimidazo-(2,1-b)quinazolinyl)oxyalkylamides
US4837239A (en) * 1985-08-23 1989-06-06 Syntex (U.S.A.) Inc. Cardiotonic phosphodiesterase inhibitors complexed with water soluble vitamins
US4775674A (en) * 1986-05-23 1988-10-04 Bristol-Myers Company Imidazoquinolinylether derivatives useful as phosphodiesterase and blood aggregation inhibitors
US4701459A (en) * 1986-07-08 1987-10-20 Bristol-Myers Company 7-amino-1,3-dihydro-2H-imidazo[4,5-b]quinolin 2-ones and method for inhibiting phosphodiesterase and blood platelet aggregation
US4943573A (en) * 1989-11-01 1990-07-24 Bristol-Myers Squibb Company Imidazo[4,5-b]quinolinyloxyalkanoic acid amides with enhanced water solubility
ATE141791T1 (de) 1991-07-05 1996-09-15 Byk Gulden Lomberg Chem Fab Verwendung substituierter pyridazine gegen dermatosen
AU665207B2 (en) * 1991-07-29 1995-12-21 Warner-Lambert Company Quinazoline derivatives as acetylcholinesterase inhibitors
US5196428A (en) * 1992-04-03 1993-03-23 Bristol-Myers Squibb Company Imidazo[4,5-b]qinolinyl oxy alkyl ureas
US5348960A (en) * 1992-04-03 1994-09-20 Bristol-Myers Squibb Company Imidazo[4,5-b]quinolinyl oxy alkyl tetrazolyl piperidine derivatives
US5208237A (en) * 1992-04-03 1993-05-04 Bristol-Meyers Squibb Company 7-oxypropylsulfonamido-imidazo[4,5-b]quinolin-2-ones
US5158958A (en) * 1992-04-03 1992-10-27 Bristol-Myers Squibb Company Imidazo[4,5-b]quinolinyl oxy alkyl sulfonyl piperidine derivatives
US7700608B2 (en) 2004-08-04 2010-04-20 Shire Holdings Ag Quinazoline derivatives and their use in the treatment of thrombocythemia
US8304420B2 (en) 2006-11-28 2012-11-06 Shire Llc Substituted quinazolines for reducing platelet count
US7910597B2 (en) 2006-11-28 2011-03-22 Shire Llc Substituted quinazolines

Family Cites Families (16)

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Publication number Priority date Publication date Assignee Title
US31617A (en) * 1861-03-05 photo-uthcqfupheh
USRE31617E (en) 1972-02-04 1984-06-26 Bristol-Myers Company Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones
US3932407A (en) * 1973-11-19 1976-01-13 Bristol-Myers Company Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones
US4313947A (en) * 1974-06-24 1982-02-02 Otsuka Pharmaceutical Co., Ltd. Platelet aggregation inhibiting 2-oxyindoles, their compositions and method of use
US4070470A (en) * 1974-06-24 1978-01-24 Otsuka Pharmaceutical Co., Ltd. Platelet aggregation inhibiting carbostyrils, their compositions and method of use
US3983119A (en) * 1974-11-06 1976-09-28 Bristol-Myers Company Process for the preparation of optionally substituted 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-ones
US3983120A (en) * 1974-11-06 1976-09-28 Bristol-Myers Company Process for the preparation of optionally substituted 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-ones
US3988340A (en) * 1975-01-23 1976-10-26 Bristol-Myers Company 6-Alkoxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-ones and 7-alkoxymethyl-6-[H]-1,2,3,4-tetrahydropyrimido[2,1-b]quinazolin-2-ones
NZ187452A (en) * 1977-06-10 1980-05-27 Otsuka Pharma Co Ltd N- substituted-aminocarbonylpropoxy-carbostyrils and their preparation
NL7807507A (nl) * 1977-07-25 1979-01-29 Hoffmann La Roche Tricyclische verbindingen.
JPS54163825A (en) * 1978-06-15 1979-12-26 Otsuka Pharma Co Ltd Phosphoesterase inhibitor
US4208521A (en) * 1978-07-31 1980-06-17 Bristol-Myers Company Process for the preparation of imidazo[2,1-b]quinazolinones
US4490371A (en) * 1983-02-16 1984-12-25 Syntex (U.S.A.) Inc. N,N-Disubstituted-(2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-B]quinazolinyl)oxyalkylamides
US4551459A (en) * 1983-02-16 1985-11-05 Syntex (U.S.A.) Inc. Method of treating heart failure using (2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-b]quinazolinyl)oxyalkylamides
JPS604186A (ja) * 1983-06-21 1985-01-10 Dai Ichi Seiyaku Co Ltd イミダゾキナゾリン化合物
ZA851131B (en) * 1984-02-15 1986-09-24 Syntex Inc (2-oxo-1,2,3,5-tetrahydroimidazo-(2,1-b)quinazolinyl)oxyalkylamides

Also Published As

Publication number Publication date
NO164654B (no) 1990-07-23
NZ211117A (en) 1987-10-30
JPS60193991A (ja) 1985-10-02
NO850564L (no) 1985-08-16
EP0153152A2 (en) 1985-08-28
DK69285A (da) 1985-08-16
FI850618A0 (fi) 1985-02-14
IL74349A0 (en) 1985-05-31
ES549920A0 (es) 1986-04-16
HU193409B (en) 1987-10-28
HU191316B (en) 1987-02-27
ES540403A0 (es) 1986-06-01
ES8606297A1 (es) 1986-04-16
ZA851131B (en) 1986-09-24
DK69285D0 (da) 1985-02-14
AU3875485A (en) 1985-08-22
NO164654C (no) 1990-10-31
ES8607299A1 (es) 1986-06-01
HUT36122A (en) 1985-08-28
IL74349A (en) 1988-07-31
FI81578C (sv) 1990-11-12
CA1254557A (en) 1989-05-23
AU581205B2 (en) 1989-02-16
EP0153152A3 (en) 1987-07-15
FI850618L (fi) 1985-08-16
US4690925A (en) 1987-09-01

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Owner name: SYNTEX (U.S.A.) INC.