NO317424B1 - HIV-inhiberende pyrimidinderivater - Google Patents

HIV-inhiberende pyrimidinderivater Download PDF

Info

Publication number: NO317424B1
Authority: NO; Norway
Prior art keywords: amine; pyrimidinyl; benzonitrile; methyl; formula
Prior art date: 1998-03-27

Application number

NO20004810A

Other languages

English (en)

Norwegian (no)

Other versions

NO20004810D0 (no

NO20004810L (no

Inventor

Jan Heeres

Michael Joseph Kukla

Paul Adriaan Jan Janssen

Marcel August Constant Janssen

Bart De Corte

Marc Rene De Jonge

Chih Yung Ho

Lucien Maria Henricus Koymans

Donald William Ludovici

Koenraad Jozef Lodewij Andries

Koen Jeanne Alfons Van Aken

Original Assignee

Janssen Pharmaceutica Nv

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.)

1998-03-27

Filing date

2000-09-26

Publication date

2004-10-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27239326&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO317424(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-05-14 Priority claimed from EP98201587A external-priority patent/EP0945442A1/en

2000-09-26 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2000-09-26 Publication of NO20004810D0 publication Critical patent/NO20004810D0/no

2000-09-26 Publication of NO20004810L publication Critical patent/NO20004810L/no

2004-10-25 Publication of NO317424B1 publication Critical patent/NO317424B1/no

Links

150000003230 pyrimidines Chemical class 0.000 title description 7
230000002401 inhibitory effect Effects 0.000 title description 2
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 273
-1 C1_6alkyl Chemical group 0.000 claims description 226
150000001412 amines Chemical class 0.000 claims description 174
150000001875 compounds Chemical class 0.000 claims description 145
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
239000002904 solvent Substances 0.000 claims description 47
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 33
125000004093 cyano group Chemical group *C#N 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 21
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
241000725303 Human immunodeficiency virus Species 0.000 claims description 19
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
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238000002360 preparation method Methods 0.000 claims description 15
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125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
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239000002585 base Substances 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
230000000798 anti-retroviral effect Effects 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
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125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 2
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SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 claims description 2
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150000001204 N-oxides Chemical class 0.000 claims 2
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239000012458 free base Substances 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
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Classifications

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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic 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
- C07D239/28—Heterocyclic 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic 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
- C07D239/28—Heterocyclic 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic 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
- C07D239/28—Heterocyclic 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic 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
- C07D239/28—Heterocyclic 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic 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
- C07D239/28—Heterocyclic 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic 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
- C07D239/28—Heterocyclic 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Virology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Tropical Medicine & Parasitology (AREA)
AIDS & HIV (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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NO20004810A 1998-03-27 2000-09-26 HIV-inhiberende pyrimidinderivater NO317424B1 (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US7963298P	1998-03-27	1998-03-27
EP98201587A EP0945442A1 (en)	1998-03-27	1998-05-14	Trisubstituted pyrimidine derivatives
EP98203948		1998-11-25
PCT/EP1999/002043 WO1999050250A1 (en)	1998-03-27	1999-03-24	Hiv inhibiting pyrimidine derivatives

Publications (3)

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NO20004810D0 NO20004810D0 (no)	2000-09-26
NO20004810L NO20004810L (no)	2000-09-26
NO317424B1 true NO317424B1 (no)	2004-10-25

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NO20004810A NO317424B1 (no)	1998-03-27	2000-09-26	HIV-inhiberende pyrimidinderivater

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JP (1)	JP3507917B2 (et)
KR (1)	KR100699514B1 (et)
CN (1)	CN1214014C (et)
AP (1)	AP1468A (et)
AT (1)	ATE232521T1 (et)
AU (1)	AU751573C (et)
BG (1)	BG64702B1 (et)
CA (1)	CA2324919C (et)
CZ (1)	CZ299380B6 (et)
DE (1)	DE69905306T2 (et)
DK (1)	DK0945443T3 (et)
EA (1)	EA002973B1 (et)
EE (1)	EE04850B1 (et)
ES (1)	ES2193660T3 (et)
HK (1)	HK1035901A1 (et)
HR (1)	HRP20000620B1 (et)
HU (1)	HU230522B1 (et)
ID (1)	ID26291A (et)
IL (1)	IL138669A0 (et)
MY (1)	MY126493A (et)
NO (1)	NO317424B1 (et)
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OA (1)	OA11492A (et)
PL (1)	PL202675B1 (et)
PT (1)	PT945443E (et)
SI (1)	SI0945443T1 (et)
SK (1)	SK287996B6 (et)
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TW (1)	TW531534B (et)
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NO20004810D0 (no)	2000-09-26
TR200002760T2 (tr)	2000-12-21
NO20004810L (no)	2000-09-26
DE69905306D1 (de)	2003-03-20
JP3507917B2 (ja)	2004-03-15
WO1999050250A1 (en)	1999-10-07
PT945443E (pt)	2003-06-30
EP1245567A1 (en)	2002-10-02
IL138669A0 (en)	2001-10-31
DK0945443T3 (da)	2003-06-02
EE04850B1 (et)	2007-06-15
CN1295564A (zh)	2001-05-16
HUP0101204A2 (hu)	2001-10-28
CA2324919C (en)	2006-10-17
CA2324919A1 (en)	1999-10-07
PL202675B1 (pl)	2009-07-31
KR100699514B1 (ko)	2007-03-26
DE69905306T2 (de)	2003-11-27
AP2000001912A0 (en)	2000-09-30
TW531534B (en)	2003-05-11
EP0945443A1 (en)	1999-09-29
EP1245567B1 (en)	2011-03-02
HK1035901A1 (en)	2001-12-14
BG104738A (en)	2001-04-30
MY126493A (en)	2006-10-31
SI0945443T1 (en)	2003-08-31
UA72458C2 (uk)	2005-03-15
HUP0101204A3 (en)	2002-08-28
JP2002509920A (ja)	2002-04-02
BG64702B1 (bg)	2005-12-30
KR20060083440A (ko)	2006-07-20
CN1214014C (zh)	2005-08-10
EE200000532A (et)	2002-02-15
AP1468A (en)	2005-09-23
AU751573C (en)	2003-10-09
ATE232521T1 (de)	2003-02-15
HRP20000620A2 (en)	2001-06-30
SK287996B6 (sk)	2012-09-03
EP0945443B9 (en)	2003-08-13
HU230522B1 (hu)	2016-10-28
EA002973B1 (ru)	2002-12-26
ES2193660T3 (es)	2003-11-01
EP0945443B1 (en)	2003-02-12
NZ506679A (en)	2002-11-26
PL343196A1 (en)	2001-07-30
AU751573B2 (en)	2002-08-22
SK14062000A3 (sk)	2001-06-11
EA200000990A1 (ru)	2001-02-26
CZ20003425A3 (cs)	2001-02-14
CZ299380B6 (cs)	2008-07-09
ID26291A (id)	2000-12-14
HRP20000620B1 (en)	2009-07-31
AU3599699A (en)	1999-10-18
OA11492A (en)	2004-05-06

Publication	Publication Date	Title
NO317424B1 (no)	2004-10-25	HIV-inhiberende pyrimidinderivater
US6197779B1 (en)	2001-03-06	HIV inhibiting pyrimidine derivative
AU782948B2 (en)	2005-09-15	Prodrugs of HIV replication inhibiting pyrimidines
NO317425B1 (no)	2004-10-25	Trisubstituerte 1,3,5-triazinderivater for behandling av HIV-infeksjoner
ZA200006044B (en)	2001-10-26	HIV inhibiting pyrimidine derivatives.
MXPA00009435A (en)	2001-07-09	Hiv inhibiting pyrimidine derivatives

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