OA10639A - C-4' modified adenosine kinase inhibitors - Google Patents

C-4' modified adenosine kinase inhibitors Download PDF

Info

Publication number: OA10639A
Authority: OA; OAPI
Prior art keywords: compound; phenyl; amino; guanidino; optionally
Prior art date: 1995-06-07

Application number

OA70150A

Other languages

English (en)

Inventor

Serg H Boyer

Mark D Erion

Bheemarao G Ugarkar

Original Assignee

Gensia Sicor

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.)

1995-06-07

Filing date

1997-12-03

Publication date

2002-09-17

1997-12-03 Application filed by Gensia Sicor filed Critical Gensia Sicor

2002-09-17 Publication of OA10639A publication Critical patent/OA10639A/en

Links

239000003121 adenosine kinase inhibitor Substances 0.000 title abstract description 13
OOXNYFKPOPJIOT-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-amine;dihydrochloride Chemical class Cl.Cl.C=12C(N)=NC=NC2=NC(C=2C=NC(=CC=2)N2CCOCC2)=CC=1C1=CC=CC(Br)=C1 OOXNYFKPOPJIOT-UHFFFAOYSA-N 0.000 title description 16
QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 341
-1 aralkylami.no Chemical group 0.000 claims description 292
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 104
125000000217 alkyl group Chemical group 0.000 claims description 69
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 68
229910052739 hydrogen Inorganic materials 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 49
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
229910052757 nitrogen Chemical group 0.000 claims description 40
125000003118 aryl group Chemical group 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
229910052736 halogen Chemical group 0.000 claims description 31
150000002367 halogens Chemical group 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 27
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
229910052720 vanadium Inorganic materials 0.000 claims description 22
125000005518 carboxamido group Chemical group 0.000 claims description 20
125000004430 oxygen atom Chemical group O* 0.000 claims description 20
125000005842 heteroatom Chemical group 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000001769 aryl amino group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
125000004122 cyclic group Chemical group 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
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239000011593 sulfur Chemical group 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 4
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125000001188 haloalkyl group Chemical group 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 8
150000002431 hydrogen Chemical class 0.000 claims 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 4
125000004663 dialkyl amino group Chemical group 0.000 claims 3
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 2
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OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 abstract description 55
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 29
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 28
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
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229960003010 sodium sulfate Drugs 0.000 description 20
229910052938 sodium sulfate Inorganic materials 0.000 description 20
235000011152 sodium sulphate Nutrition 0.000 description 20
241000700159 Rattus Species 0.000 description 19
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
108010076278 Adenosine kinase Proteins 0.000 description 15
102100032534 Adenosine kinase Human genes 0.000 description 15
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206010010904 Convulsion Diseases 0.000 description 12
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150000001412 amines Chemical class 0.000 description 10
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WHSIXKUPQCKWBY-IOSLPCCCSA-N 5-iodotubercidin Chemical compound C1=C(I)C=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O WHSIXKUPQCKWBY-IOSLPCCCSA-N 0.000 description 9
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HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Dermatology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Saccharide Compounds (AREA)
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OA70150A 1995-06-07 1997-12-03 C-4' modified adenosine kinase inhibitors OA10639A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/486,161 US5674998A (en)	1989-09-15	1995-06-07	C-4' modified adenosine kinase inhibitors

Publications (1)

Publication Number	Publication Date
OA10639A true OA10639A (en)	2002-09-17

Family

ID=23930844

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA70150A OA10639A (en)	1995-06-07	1997-12-03	C-4' modified adenosine kinase inhibitors

Country Status (24)

Country	Link
US (1)	US5674998A (is)
EP (1)	EP0832091B1 (is)
JP (1)	JPH11507387A (is)
KR (1)	KR19990022740A (is)
CN (1)	CN1190401A (is)
AP (1)	AP9701165A0 (is)
AT (1)	ATE257841T1 (is)
AU (1)	AU6178396A (is)
BG (1)	BG102163A (is)
BR (1)	BR9609013A (is)
CA (1)	CA2220642A1 (is)
CZ (1)	CZ392797A3 (is)
DE (1)	DE69631330T2 (is)
EA (1)	EA199800009A1 (is)
HU (1)	HUP9802193A3 (is)
IL (1)	IL122335A0 (is)
IS (1)	IS4621A (is)
MX (1)	MX9709859A (is)
NO (1)	NO975585L (is)
OA (1)	OA10639A (is)
PL (1)	PL323904A1 (is)
SK (1)	SK166097A3 (is)
TR (1)	TR199701539T1 (is)
WO (1)	WO1996040705A1 (is)

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DE59500788D1 (de) *	1994-05-03	1997-11-20	Ciba Geigy Ag	Pyrrolopyrimidinderivate mit antiproliferativer Wirkung
SI9620103A (sl) *	1995-07-06	1998-10-31	Novartis Ag	Pirolopirimidini in postopki za njihovo pripravo
US6051578A (en) *	1996-02-12	2000-04-18	Pfizer Inc.	Pyrazolopyrimidines for treatment of CNS disorders
US7863444B2 (en)	1997-03-19	2011-01-04	Abbott Laboratories	4-aminopyrrolopyrimidines as kinase inhibitors
US6713474B2 (en)	1998-09-18	2004-03-30	Abbott Gmbh & Co. Kg	Pyrrolopyrimidines as therapeutic agents
YU25500A (sh)	1999-05-11	2003-08-29	Pfizer Products Inc.	Postupak za sintezu analoga nukleozida
US6831069B2 (en)	1999-08-27	2004-12-14	Ribapharm Inc.	Pyrrolo[2,3-d]pyrimidine nucleoside analogs
AU769578B2 (en) *	1999-08-27	2004-01-29	Icn Pharmaceuticals, Inc.	Pyrrolo(2,3-d)pyrimidine nucleoside analogs
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Also Published As

Publication number	Publication date
EP0832091A1 (en)	1998-04-01
CZ392797A3 (cs)	1999-04-14
HUP9802193A3 (en)	1999-10-28
MX9709859A (es)	1998-08-30
AP9701165A0 (en)	1998-01-31
DE69631330D1 (de)	2004-02-19
CN1190401A (zh)	1998-08-12
EA199800009A1 (ru)	1998-06-25
NO975585D0 (no)	1997-12-03
HUP9802193A2 (hu)	1999-05-28
US5674998A (en)	1997-10-07
WO1996040705A1 (en)	1996-12-19
NO975585L (no)	1998-02-05
TR199701539T1 (xx)	1998-04-21
IS4621A (is)	1997-11-26
AU6178396A (en)	1996-12-30
PL323904A1 (en)	1998-04-27
CA2220642A1 (en)	1996-12-19
BG102163A (en)	1998-10-30
BR9609013A (pt)	1999-12-14
DE69631330T2 (de)	2004-10-28
ATE257841T1 (de)	2004-01-15
EP0832091B1 (en)	2004-01-14
JPH11507387A (ja)	1999-06-29
SK166097A3 (en)	1999-06-11
KR19990022740A (ko)	1999-03-25
IL122335A0 (en)	1998-04-05

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