AU2003276125B2 - Chemical process - Google Patents

Chemical process Download PDF

Info

Publication number: AU2003276125B2
Authority: AU; Australia
Prior art keywords: formula; compound; alkyl; hydrogen; methyl
Prior art date: 2002-06-17
Legal status (The legal status 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 status listed.): Ceased

Application number

AU2003276125A

Other languages

English (en)

Other versions

AU2003276125A1 (en

Inventor

Amogh Boloor

Mui Cheung

Jeffrey Alan Stafford

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SmithKline Beecham Corp

Original Assignee

SmithKline Beecham Corp

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.)

2002-06-17

Filing date

2003-06-17

Publication date

2007-05-17

2003-06-17 Application filed by SmithKline Beecham Corp filed Critical SmithKline Beecham Corp

2003-12-31 Publication of AU2003276125A1 publication Critical patent/AU2003276125A1/en

2007-05-17 Application granted granted Critical

2007-05-17 Publication of AU2003276125B2 publication Critical patent/AU2003276125B2/en

2023-06-17 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

238000001311 chemical methods and process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 142
238000000034 method Methods 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 58
-1 aralkoxy Chemical group 0.000 claims description 50
229910052739 hydrogen Inorganic materials 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
125000001072 heteroaryl group Chemical group 0.000 claims description 18
230000008569 process Effects 0.000 claims description 18
229940100198 alkylating agent Drugs 0.000 claims description 15
239000002168 alkylating agent Substances 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 11
JHGRUPGVUMAQQU-UHFFFAOYSA-N 2,3-dimethyl-6-nitroindazole Chemical compound C1=C([N+]([O-])=O)C=CC2=C(C)N(C)N=C21 JHGRUPGVUMAQQU-UHFFFAOYSA-N 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 10
125000001769 aryl amino group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
KTPBKMYOIFHJMI-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(N)C=C1S(N)(=O)=O KTPBKMYOIFHJMI-UHFFFAOYSA-N 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
239000000203 mixture Substances 0.000 description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 42
150000003839 salts Chemical class 0.000 description 38
235000002639 sodium chloride Nutrition 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000007787 solid Substances 0.000 description 36
238000001819 mass spectrum Methods 0.000 description 33
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238000006243 chemical reaction Methods 0.000 description 30
239000000047 product Substances 0.000 description 29
239000012453 solvate Substances 0.000 description 29
239000002904 solvent Substances 0.000 description 29
235000019439 ethyl acetate Nutrition 0.000 description 28
239000000543 intermediate Substances 0.000 description 28
230000000694 effects Effects 0.000 description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 23
230000002829 reductive effect Effects 0.000 description 23
239000008194 pharmaceutical composition Substances 0.000 description 22
238000011282 treatment Methods 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
206010028980 Neoplasm Diseases 0.000 description 20
208000035475 disorder Diseases 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
238000002360 preparation method Methods 0.000 description 18
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
229910001868 water Inorganic materials 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000033115 angiogenesis Effects 0.000 description 15
239000010410 layer Substances 0.000 description 15
239000003112 inhibitor Substances 0.000 description 14
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
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238000009472 formulation Methods 0.000 description 13
239000000843 powder Substances 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
238000001914 filtration Methods 0.000 description 12
239000000725 suspension Substances 0.000 description 12
241000124008 Mammalia Species 0.000 description 11
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 11
238000004128 high performance liquid chromatography Methods 0.000 description 11
239000002002 slurry Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
239000003814 drug Substances 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
238000010992 reflux Methods 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
108091008605 VEGF receptors Proteins 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
230000002491 angiogenic effect Effects 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
238000000132 electrospray ionisation Methods 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000006467 substitution reaction Methods 0.000 description 9
239000003826 tablet Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
230000002159 abnormal effect Effects 0.000 description 8
125000002947 alkylene group Chemical group 0.000 description 8
239000002246 antineoplastic agent Substances 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
238000000746 purification Methods 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 6
125000004647 alkyl sulfenyl group Chemical group 0.000 description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
125000004414 alkyl thio group Chemical group 0.000 description 6
230000029936 alkylation Effects 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
229940034982 antineoplastic agent Drugs 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
230000006870 function Effects 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 6
229940124676 vascular endothelial growth factor receptor Drugs 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
XJQWZUJNHLGBQG-UHFFFAOYSA-N 1-(methylsulfonylmethyl)-4-nitrobenzene Chemical compound CS(=O)(=O)CC1=CC=C([N+]([O-])=O)C=C1 XJQWZUJNHLGBQG-UHFFFAOYSA-N 0.000 description 5
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 5
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
102000009465 Growth Factor Receptors Human genes 0.000 description 5
108010009202 Growth Factor Receptors Proteins 0.000 description 5
108091000080 Phosphotransferase Proteins 0.000 description 5
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125000004043 oxo group Chemical group O=* 0.000 description 5
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102000020233 phosphotransferase Human genes 0.000 description 5
230000009467 reduction Effects 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
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PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
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UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
229960004355 vindesine Drugs 0.000 description 1
GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
229960002066 vinorelbine Drugs 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
229930195724 β-lactose Natural products 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
- A61P35/00—Antineoplastic agents
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Rheumatology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Urology & Nephrology (AREA)
Ophthalmology & Optometry (AREA)
Dermatology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

AU2003276125A 2002-06-17 2003-06-17 Chemical process Ceased AU2003276125B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US38934902P	2002-06-17	2002-06-17
US60/389,349		2002-06-17
PCT/US2003/019211 WO2003106416A2 (en)	2002-06-17	2003-06-17	Chemical process

Publications (2)

Publication Number	Publication Date
AU2003276125A1 AU2003276125A1 (en)	2003-12-31
AU2003276125B2 true AU2003276125B2 (en)	2007-05-17

Family

ID=29736629

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2003276125A Ceased AU2003276125B2 (en)	2002-06-17	2003-06-17	Chemical process

Country Status (10)

Country	Link
US (1)	US20060252943A1 (2)
EP (1)	EP1515955A4 (2)
JP (1)	JP2005529954A (2)
CN (1)	CN1688553A (2)
AU (1)	AU2003276125B2 (2)
CA (1)	CA2489648A1 (2)
IL (1)	IL165286A0 (2)
MX (1)	MXPA04012860A (2)
PL (1)	PL374963A1 (2)
WO (1)	WO2003106416A2 (2)

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CN103232443B (zh) *	2013-02-01	2014-12-10	天津药物研究院	一种吲唑衍生物的晶型及其制备和用途
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- 2003-06-17 IL IL16528603A patent/IL165286A0/xx unknown
- 2003-06-17 AU AU2003276125A patent/AU2003276125B2/en not_active Ceased
- 2003-06-17 PL PL03374963A patent/PL374963A1/xx not_active Application Discontinuation
- 2003-06-17 JP JP2004513249A patent/JP2005529954A/ja active Pending
- 2003-06-17 MX MXPA04012860A patent/MXPA04012860A/es unknown
- 2003-06-17 WO PCT/US2003/019211 patent/WO2003106416A2/en not_active Ceased
- 2003-06-17 EP EP03742050A patent/EP1515955A4/en not_active Withdrawn
- 2003-06-17 CN CNA038141698A patent/CN1688553A/zh active Pending
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Also Published As

Publication number	Publication date
CN1688553A (zh)	2005-10-26
PL374963A1 (en)	2005-11-14
IL165286A0 (en)	2005-12-18
JP2005529954A (ja)	2005-10-06
MXPA04012860A (es)	2005-09-20
EP1515955A2 (en)	2005-03-23
CA2489648A1 (en)	2003-12-24
US20060252943A1 (en)	2006-11-09
EP1515955A4 (en)	2006-05-03
WO2003106416A2 (en)	2003-12-24
WO2003106416A3 (en)	2004-05-06
AU2003276125A1 (en)	2003-12-31

Legal Events

Date	Code	Title	Description
2005-02-03	DA3	Amendments made section 104	Free format text: THE NATURE OF THE AMENDMENT IS: ADD THE NAME OF THE INVENTOR STAFFORD, JEFFREY ALAN
2007-09-13	FGA	Letters patent sealed or granted (standard patent)
2010-01-14	MK14	Patent ceased section 143(a) (annual fees not paid) or expired

Publication	Publication Date	Title
AU2003276125B2 (en)	2007-05-17	Chemical process
EP1343782B1 (en)	2009-05-06	Pyrimidineamines as angiogenesis modulators
US7459455B2 (en)	2008-12-02	Pyrimidine compounds
AU2002246723A1 (en)	2003-02-06	Pyrimidineamines as angiogenesis modulators
EP1487824A1 (en)	2004-12-22	Diamino-pyrimidines and their use as angiogenesis inhibitors
EP1341771A2 (en)	2003-09-10	Benzimidazole derivatives useful as tie-2 and/or vegfr-2 inhibitors
WO2004112714A2 (en)	2004-12-29	Chemical compounds
HK1059926B (en)	2009-12-24	Pyrimidineamines as angiogenesis modulators
HK1149930B (en)	2016-04-29	Pyrimidineamines as angiogenesis modulators