ZA200602440B - HIV replication inhibiting purine derivatives - Google Patents

HIV replication inhibiting purine derivatives Download PDF

Info

Publication number: ZA200602440B
Authority: ZA; South Africa
Prior art keywords: aminocarbonyl; cyano; mono; formula; optionally substituted
Prior art date: 2003-09-25

Application number

ZA200602440A

Other languages

English (en)

Inventor

Lewi Paulus Joannes

Koymans Lucien Maria Henricus

Heeres Jan

Leenders Ruben Gerardus George

De Jonge Marc Rene

Daeyaert Frederik Frans Desire

Vinkers Hendrik Maarten

Vandenput Dirk Alfons Leo

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.)

2003-09-25

Filing date

2006-03-24

Publication date

2007-09-26

2006-03-24 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2007-09-26 Publication of ZA200602440B publication Critical patent/ZA200602440B/en

Links

229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 5
230000010076 replication Effects 0.000 title description 5
230000002401 inhibitory effect Effects 0.000 title description 3
125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 2
-1 cyano, aminocarbonyl Chemical group 0.000 claims description 189
150000001875 compounds Chemical class 0.000 claims description 171
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 144
125000004093 cyano group Chemical group *C#N 0.000 claims description 139
125000000217 alkyl group Chemical group 0.000 claims description 116
125000001424 substituent group Chemical group 0.000 claims description 110
125000002619 bicyclic group Chemical group 0.000 claims description 80
125000002950 monocyclic group Chemical group 0.000 claims description 80
125000003118 aryl group Chemical group 0.000 claims description 64
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
229910052739 hydrogen Inorganic materials 0.000 claims description 50
239000001257 hydrogen Substances 0.000 claims description 50
229920006395 saturated elastomer Polymers 0.000 claims description 42
150000003839 salts Chemical class 0.000 claims description 41
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 38
125000000623 heterocyclic group Chemical group 0.000 claims description 38
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
150000001204 N-oxides Chemical class 0.000 claims description 27
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238000000034 method Methods 0.000 claims description 18
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239000000126 substance Substances 0.000 claims description 13
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208000031886 HIV Infections Diseases 0.000 claims description 9
208000037357 HIV infectious disease Diseases 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 9
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238000004519 manufacturing process Methods 0.000 claims description 9
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125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
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125000004448 alkyl carbonyl group Chemical group 0.000 description 2
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239000003638 chemical reducing agent Substances 0.000 description 2
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125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
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150000004677 hydrates Chemical class 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
125000004113 cyclononanyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 description 1
125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
125000005879 dioxolanyl group Chemical group 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
125000005883 dithianyl group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
125000005945 imidazopyridyl group Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000007813 immunodeficiency Effects 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000005990 isobenzothienyl group Chemical group 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000003965 isoxazolidinyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000004972 metal peroxides Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
125000005963 oxadiazolidinyl group Chemical group 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
150000004965 peroxy acids Chemical group 0.000 description 1
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
238000000053 physical method Methods 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical group 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
125000005996 thiadiazolopyrimidinyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000005310 triazolidinyl group Chemical group N1(NNCC1)* 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
125000005455 trithianyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- 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
- A61K31/33—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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- 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
- A61K31/33—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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Virology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Tropical Medicine & Parasitology (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
AIDS & HIV (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

ZA200602440A 2003-09-25 2006-03-24 HIV replication inhibiting purine derivatives ZA200602440B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP0350659		2003-09-25

Publications (1)

Publication Number	Publication Date
ZA200602440B true ZA200602440B (en)	2007-09-26

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ID=34354400

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Application Number	Title	Priority Date	Filing Date
ZA200602440A ZA200602440B (en)	2003-09-25	2006-03-24	HIV replication inhibiting purine derivatives

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Country	Link
US (1)	US8026245B2 (fr)
EP (1)	EP1668011B1 (fr)
JP (1)	JP5506751B2 (fr)
KR (1)	KR20060121878A (fr)
CN (1)	CN100475815C (fr)
AP (1)	AP2006003517A0 (fr)
AT (1)	ATE500254T1 (fr)
AU (1)	AU2004274185B2 (fr)
BR (1)	BRPI0414791A (fr)
CA (1)	CA2535313C (fr)
DE (1)	DE602004031641D1 (fr)
EA (1)	EA009734B1 (fr)
ES (1)	ES2361835T3 (fr)
IL (1)	IL174467A0 (fr)
MX (1)	MXPA06002069A (fr)
NO (1)	NO20061788L (fr)
TW (1)	TW200518758A (fr)
WO (1)	WO2005028479A2 (fr)
ZA (1)	ZA200602440B (fr)

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2004
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Publication number	Publication date
CA2535313C (fr)	2012-07-17
IL174467A0 (en)	2006-08-01
CA2535313A1 (fr)	2005-03-31
AU2004274185B2 (en)	2009-12-10
JP2012006945A (ja)	2012-01-12
JP5506751B2 (ja)	2014-05-28
EA009734B1 (ru)	2008-02-28
MXPA06002069A (es)	2006-05-19
US8026245B2 (en)	2011-09-27
WO2005028479A2 (fr)	2005-03-31
KR20060121878A (ko)	2006-11-29
US20060293330A1 (en)	2006-12-28
AU2004274185A1 (en)	2005-03-31
CN100475815C (zh)	2009-04-08
CN1856496A (zh)	2006-11-01
NO20061788L (no)	2006-04-24
EA200600648A1 (ru)	2006-08-25
TW200518758A (en)	2005-06-16
ATE500254T1 (de)	2011-03-15
JP2007506707A (ja)	2007-03-22
BRPI0414791A (pt)	2006-11-21
ES2361835T3 (es)	2011-06-22
EP1668011A2 (fr)	2006-06-14
JP4825672B2 (ja)	2011-11-30
AP2006003517A0 (en)	2006-02-28
DE602004031641D1 (de)	2011-04-14
EP1668011B1 (fr)	2011-03-02
WO2005028479A3 (fr)	2005-06-16

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FI88300C (fi)	1993-04-26	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara diazinylpiperidinderivat av cykliska amider och imider
WO2005118578A1 (fr)	2005-12-15	Mercaptoimidazoles en tant qu'antagonistes du récepteur ccr2
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