NO313962B1 - Pyrrolo[2,3]pyrimidiner, deres fremstilling og anvendelse og farmasöytiskepreparater inneholdende dem - Google Patents

Pyrrolo[2,3]pyrimidiner, deres fremstilling og anvendelse og farmasöytiskepreparater inneholdende dem Download PDF

Info

Publication number: NO313962B1
Authority: NO; Norway
Prior art keywords: phenyl; pyrrolo; pyrimidin; amino; formula
Prior art date: 1997-03-19

Application number

NO19994509A

Other languages

English (en)

Norwegian (no)

Other versions

NO994509D0 (no

NO994509L (no

Inventor

David John Calderwood

David Norman Johnston

Paul Rafferty

Helen Louise Twigger

Rainer Munschauer

Lee Daniel Arnold

Original Assignee

Basf 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.)

1997-03-19

Filing date

1999-09-17

Publication date

2003-01-06

1999-09-17 Application filed by Basf Ag filed Critical Basf Ag

1999-09-17 Publication of NO994509D0 publication Critical patent/NO994509D0/no

1999-09-17 Publication of NO994509L publication Critical patent/NO994509L/no

2003-01-06 Publication of NO313962B1 publication Critical patent/NO313962B1/no

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title description 22
KCTZOTUQSGYWLV-UHFFFAOYSA-N N1C=NC=C2N=CC=C21 Chemical class N1C=NC=C2N=CC=C21 KCTZOTUQSGYWLV-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 172
-1 2-phenyl-1,3-dioxan-5-yl Chemical group 0.000 claims abstract description 139
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 84
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 84
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
125000000217 alkyl group Chemical group 0.000 claims abstract description 37
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
239000001257 hydrogen Substances 0.000 claims abstract description 33
238000000034 method Methods 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 25
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 23
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 18
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 17
229910052799 carbon Inorganic materials 0.000 claims abstract description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims abstract description 9
230000002062 proliferating effect Effects 0.000 claims abstract description 8
210000000987 immune system Anatomy 0.000 claims abstract description 6
230000008569 process Effects 0.000 claims abstract description 6
208000037765 diseases and disorders Diseases 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 33
229910052736 halogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 17
229910021529 ammonia Inorganic materials 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 9
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 7
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 4
NFSWHYRUVWRUDN-UHFFFAOYSA-N 5-(4-phenoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2NC=C1C(C=C1)=CC=C1OC1=CC=CC=C1 NFSWHYRUVWRUDN-UHFFFAOYSA-N 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
230000001613 neoplastic effect Effects 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
ZCBPGURKZDCEFP-UHFFFAOYSA-N 2-[4-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidin-5-yl)phenoxy]-5-nitrobenzoic acid Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(C=C1)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1C(O)=O ZCBPGURKZDCEFP-UHFFFAOYSA-N 0.000 claims description 3
VPDWAEBGKFDQTQ-UHFFFAOYSA-N 5-[4-(benzenesulfonyl)phenyl]-7-tert-butylpyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C12=C(N)N=CN=C2N(C(C)(C)C)C=C1C(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 VPDWAEBGKFDQTQ-UHFFFAOYSA-N 0.000 claims description 3
PAHKLGUKLSFIBQ-UHFFFAOYSA-N 7-cyclopentyl-5-(2-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2N(C2CCCC2)C=C1C1=CC=CC=C1OC1=CC=CC=C1 PAHKLGUKLSFIBQ-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
DAGSDOGBZLLVLH-UHFFFAOYSA-N n-[4-(4-amino-7-cyclopentylpyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-4-tert-butylbenzenesulfonamide Chemical compound COC1=CC(C=2C3=C(N)N=CN=C3N(C3CCCC3)C=2)=CC=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 DAGSDOGBZLLVLH-UHFFFAOYSA-N 0.000 claims description 3
ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 claims description 2
GQMYAXSHDAEFGH-UHFFFAOYSA-N C(C)(C)(C)N1C=C(C2=C1N=CN=C2N)C2=CC=C(C=C2)S(=O)C2=CC=CC=C2.C(C)(C)(C)N2C=C(C1=C2N=CN=C1N)C1=CC=C(C=C1)OC1=CC=C(C=C1)OC Chemical compound C(C)(C)(C)N1C=C(C2=C1N=CN=C2N)C2=CC=C(C=C2)S(=O)C2=CC=CC=C2.C(C)(C)(C)N2C=C(C1=C2N=CN=C1N)C1=CC=C(C=C1)OC1=CC=C(C=C1)OC GQMYAXSHDAEFGH-UHFFFAOYSA-N 0.000 claims description 2
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125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
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IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims 1
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WNYKZALHSGWGLX-UHFFFAOYSA-N NC1=C(OC2=CC=C(C=C2)C2=CN(C=3N=CN=C(C32)N)C(C)C)C=CC=C1.NC=1C=C(OC3=CC=C(C=C3)C3=CN(C=2N=CN=C(C23)N)C(C)(C)C)C=CC1 Chemical compound NC1=C(OC2=CC=C(C=C2)C2=CN(C=3N=CN=C(C32)N)C(C)C)C=CC=C1.NC=1C=C(OC3=CC=C(C=C3)C3=CN(C=2N=CN=C(C23)N)C(C)(C)C)C=CC1 WNYKZALHSGWGLX-UHFFFAOYSA-N 0.000 claims 1
IZZRYPGIYWRQCJ-UHFFFAOYSA-N n-[4-(4-amino-7-cyclopentylpyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxyphenyl]benzenesulfonamide Chemical compound C1=2C(N)=NC=NC=2N(C2CCCC2)C=C1C(C=C1O)=CC=C1NS(=O)(=O)C1=CC=CC=C1 IZZRYPGIYWRQCJ-UHFFFAOYSA-N 0.000 claims 1
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Classifications

- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

NO19994509A 1997-03-19 1999-09-17 Pyrrolo[2,3]pyrimidiner, deres fremstilling og anvendelse og farmasöytiskepreparater inneholdende dem NO313962B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US4083697P	1997-03-19	1997-03-19
PCT/EP1998/001357 WO1998041525A1 (fr)	1997-03-19	1998-03-09	Pyrrolo [2,3] pyrimidines et leur utilisation comme inhibiteurs de la tyrosine kinase

Publications (3)

Publication Number	Publication Date
NO994509D0 NO994509D0 (no)	1999-09-17
NO994509L NO994509L (no)	1999-09-17
NO313962B1 true NO313962B1 (no)	2003-01-06

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NO19994509A NO313962B1 (no)	1997-03-19	1999-09-17	Pyrrolo[2,3]pyrimidiner, deres fremstilling og anvendelse og farmasöytiskepreparater inneholdende dem

Country Status (23)

Country	Link
US (1)	US6001839A (fr)
EP (1)	EP0970084B1 (fr)
JP (1)	JP2001516353A (fr)
KR (1)	KR20000076426A (fr)
CN (1)	CN1134439C (fr)
AT (1)	ATE242245T1 (fr)
AU (1)	AU748884B2 (fr)
BG (1)	BG64282B1 (fr)
BR (1)	BR9808281A (fr)
CA (1)	CA2283961A1 (fr)
DE (1)	DE69815317T2 (fr)
DK (1)	DK0970084T3 (fr)
ES (1)	ES2202827T3 (fr)
HU (1)	HUP0001507A3 (fr)
ID (1)	ID24653A (fr)
IL (1)	IL131582A0 (fr)
NO (1)	NO313962B1 (fr)
NZ (1)	NZ337529A (fr)
PL (1)	PL335685A1 (fr)
PT (1)	PT970084E (fr)
SK (1)	SK125999A3 (fr)
TR (1)	TR199902301T2 (fr)
WO (1)	WO1998041525A1 (fr)

Families Citing this family (117)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7863444B2 (en)	1997-03-19	2011-01-04	Abbott Laboratories	4-aminopyrrolopyrimidines as kinase inhibitors
CA2341409A1 (fr) *	1998-08-31	2000-03-09	Merck And Co., Inc.	Nouveaux inhibiteurs d'angiogenese
BR9913887A (pt) *	1998-09-18	2001-10-23	Basf Ag	Composto, e, métodos de inibir a atividade de proteìna quinase, de tratar um paciente que tenha uma condição que seja mediada pela atividade da proteìna quinase e de diminuir a fertilidade em um paciente
US6713474B2 (en)	1998-09-18	2004-03-30	Abbott Gmbh & Co. Kg	Pyrrolopyrimidines as therapeutic agents
US6265403B1 (en) *	1999-01-20	2001-07-24	Merck & Co., Inc.	Angiogenesis inhibitors
US6432979B1 (en)	1999-08-12	2002-08-13	American Cyanamid Company	Method of treating or inhibiting colonic polyps and colorectal cancer
TR200201506T2 (tr) *	1999-09-17	2002-10-21	Abbott Gmbh & Co. Kg	Terapötik maddeler olarak kinaz inhibitörleri
EP1212327B8 (fr)	1999-09-17	2004-02-25	Abbott GmbH & Co. KG	Pyrazolopyrimidines en tant qu'agents therapeutiques
US7071199B1 (en)	1999-09-17	2006-07-04	Abbott Gmbh & Cco. Kg	Kinase inhibitors as therapeutic agents
US7101869B2 (en)	1999-11-30	2006-09-05	Pfizer Inc.	2,4-diaminopyrimidine compounds useful as immunosuppressants
AU2000240570A1 (en) *	2000-03-29	2001-10-08	Knoll Gesellschaft Mit Beschraenkter Haftung	Pyrrolopyrimidines as tyrosine kinase inhibitors
US7369946B2 (en)	2000-03-29	2008-05-06	Abbott Gmbh & Co. Kg	Method of identifying inhibitors of Tie-2
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NO994509D0 (no)	1999-09-17
EP0970084B1 (fr)	2003-06-04
IL131582A0 (en)	2001-01-28
AU748884B2 (en)	2002-06-13
JP2001516353A (ja)	2001-09-25
US6001839A (en)	1999-12-14
ID24653A (id)	2000-07-27
WO1998041525A1 (fr)	1998-09-24
EP0970084A1 (fr)	2000-01-12
BG103785A (en)	2000-06-30
DE69815317D1 (de)	2003-07-10
AU6829398A (en)	1998-10-12
PT970084E (pt)	2003-10-31
SK125999A3 (en)	2000-05-16
ATE242245T1 (de)	2003-06-15
DK0970084T3 (da)	2003-09-29
BG64282B1 (bg)	2004-08-31
PL335685A1 (en)	2000-05-08
HUP0001507A2 (hu)	2000-10-28
CA2283961A1 (fr)	1998-09-24
KR20000076426A (ko)	2000-12-26
CN1134439C (zh)	2004-01-14
ES2202827T3 (es)	2004-04-01
HUP0001507A3 (en)	2002-01-28
TR199902301T2 (xx)	1999-12-21
NO994509L (no)	1999-09-17
CN1259950A (zh)	2000-07-12
DE69815317T2 (de)	2005-04-07
NZ337529A (en)	2000-10-27
BR9808281A (pt)	2000-05-16

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Publication	Publication Date	Title
NO313962B1 (no)	2003-01-06	Pyrrolo[2,3]pyrimidiner, deres fremstilling og anvendelse og farmasöytiskepreparater inneholdende dem
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JP2002527359A (ja)	2002-08-27	キナーゼインヒビターとしての４−アミノピロリピリミジン
WO2001072751A1 (fr)	2001-10-04	Pyrrolopyrimidines utilisees comme inhibiteurs de tyrosine kinases
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