UA80175C2 - Thienopyridazinones, process for their preparation and their use in the modulation of autoimmune disease - Google Patents

Thienopyridazinones, process for their preparation and their use in the modulation of autoimmune disease Download PDF

Info

Publication number: UA80175C2
Authority: UA; Ukraine
Prior art keywords: methyl; formula; pyrazol; dimethyl; hydroxy
Prior art date: 2003-01-17

Application number

UAA200506375A

Other languages

English (en)

Ukrainian (uk)

Inventor

Martin Edward Cooper

Simon David Guile

Anthony Howard Ingall

Rukhsana Tasneem Rasul

Original Assignee

Astrazeneca Ab

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.)

2003-01-17

Filing date

2004-01-15

Publication date

2007-08-27

2004-01-15 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2007-08-27 Publication of UA80175C2 publication Critical patent/UA80175C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 60
208000023275 Autoimmune disease Diseases 0.000 title abstract description 6
238000002360 preparation method Methods 0.000 title abstract description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 68
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 43
150000003839 salts Chemical class 0.000 claims abstract description 32
125000005842 heteroatom Chemical group 0.000 claims abstract description 14
125000003118 aryl group Chemical group 0.000 claims abstract description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
239000001301 oxygen Substances 0.000 claims abstract description 11
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
238000002560 therapeutic procedure Methods 0.000 claims abstract description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
239000012453 solvate Substances 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 120
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
-1 3,5-dimethyl-1H-pyrazol-4-yl Chemical group 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
201000010099 disease Diseases 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 12
229910052717 sulfur Chemical group 0.000 claims description 12
239000011593 sulfur Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
125000006413 ring segment Chemical group 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000000464 thioxo group Chemical group S=* 0.000 claims description 4
206010062016 Immunosuppression Diseases 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
239000007822 coupling agent Substances 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
230000001506 immunosuppresive effect Effects 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
208000018569 Respiratory Tract disease Diseases 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
239000005864 Sulphur Chemical group 0.000 abstract 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
239000007787 solid Substances 0.000 description 78
239000000047 product Substances 0.000 description 76
238000004949 mass spectrometry Methods 0.000 description 51
239000000243 solution Substances 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 45
239000000126 substance Substances 0.000 description 45
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 37
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
239000000284 extract Substances 0.000 description 19
239000000377 silicon dioxide Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
238000004440 column chromatography Methods 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 11
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
206010039083 rhinitis Diseases 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
102100033891 Arylsulfatase I Human genes 0.000 description 8
101000925544 Homo sapiens Arylsulfatase I Proteins 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 8
238000010992 reflux Methods 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
239000003480 eluent Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000001569 carbon dioxide Substances 0.000 description 6
229910002092 carbon dioxide Inorganic materials 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
208000010668 atopic eczema Diseases 0.000 description 4
238000009835 boiling Methods 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
201000004624 Dermatitis Diseases 0.000 description 3
239000007818 Grignard reagent Substances 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
150000004795 grignard reagents Chemical class 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
210000004072 lung Anatomy 0.000 description 3
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230000000144 pharmacologic effect Effects 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
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230000035755 proliferation Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
210000002345 respiratory system Anatomy 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 2
NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical group C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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229910019142 PO4 Inorganic materials 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
241000721454 Pemphigus Species 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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210000001744 T-lymphocyte Anatomy 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
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230000000172 allergic effect Effects 0.000 description 2
150000008064 anhydrides Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
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150000007529 inorganic bases Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 2
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UAA200506375A 2003-01-17 2004-01-15 Thienopyridazinones, process for their preparation and their use in the modulation of autoimmune disease UA80175C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE0300120A SE0300120D0 (sv)	2003-01-17	2003-01-17	Novel compounds
PCT/SE2004/000051 WO2004065393A1 (en)	2003-01-17	2004-01-15	Novel compounds

Publications (1)

Publication Number	Publication Date
UA80175C2 true UA80175C2 (en)	2007-08-27

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Application Number	Title	Priority Date	Filing Date
UAA200506375A UA80175C2 (en)	2003-01-17	2004-01-15	Thienopyridazinones, process for their preparation and their use in the modulation of autoimmune disease

Country Status (22)

Country	Link
US (2)	US7064126B2 (de)
EP (1)	EP1587809B1 (de)
JP (1)	JP4589298B2 (de)
KR (1)	KR20050092759A (de)
CN (1)	CN100358900C (de)
AT (1)	ATE375352T1 (de)
AU (1)	AU2004205617B2 (de)
BR (1)	BRPI0406780A (de)
CA (1)	CA2512736A1 (de)
DE (1)	DE602004009407T2 (de)
ES (1)	ES2293208T3 (de)
IL (1)	IL169363A (de)
IS (1)	IS2503B (de)
MX (1)	MXPA05007494A (de)
NO (1)	NO20053827L (de)
NZ (1)	NZ541216A (de)
PL (1)	PL378223A1 (de)
RU (1)	RU2331646C2 (de)
SE (1)	SE0300120D0 (de)
UA (1)	UA80175C2 (de)
WO (1)	WO2004065393A1 (de)
ZA (1)	ZA200505273B (de)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0117583D0 (en)	2001-07-19	2001-09-12	Astrazeneca Ab	Novel compounds
GB0118479D0 (en) *	2001-07-28	2001-09-19	Astrazeneca Ab	Novel compounds
SE0300120D0 (sv) *	2003-01-17	2003-01-17	Astrazeneca Ab	Novel compounds
MXPA05007495A (es) *	2003-01-17	2005-09-21	Astrazeneca Ab	Tienopiridazinonas y su uso en la modulacion de enfermedades autoinmunes.
SE0300119D0 (sv)	2003-01-17	2003-01-17	Astrazeneca Ab	Novel compounds
CN1925855B (zh)	2003-12-19	2010-06-16	普莱希科公司	开发Ret调节剂的化合物和方法
US7498342B2 (en)	2004-06-17	2009-03-03	Plexxikon, Inc.	Compounds modulating c-kit activity
US7846941B2 (en)	2005-05-17	2010-12-07	Plexxikon, Inc.	Compounds modulating c-kit and c-fms activity and uses therefor
UA95244C2 (ru)	2005-06-22	2011-07-25	Плексикон, Инк.	Соединения и способ модулирования активности киназ, и показания для их применения
ES2559521T3 (es) *	2006-10-16	2016-02-12	Thesan Pharmaceuticals, Inc.	Pirazolil tienopiridinas terapéuticas
WO2008063888A2 (en)	2006-11-22	2008-05-29	Plexxikon, Inc.	Compounds modulating c-fms and/or c-kit activity and uses therefor
WO2008079909A1 (en)	2006-12-21	2008-07-03	Plexxikon, Inc.	Pyrrolo [2,3-b] pyridines as kinase modulators
PE20121126A1 (es)	2006-12-21	2012-08-24	Plexxikon Inc	Compuestos pirrolo [2,3-b] piridinas como moduladores de quinasa
JP2010514695A (ja)	2006-12-21	2010-05-06	プレキシコン，インコーポレーテッド	キナーゼ調節のための化合物および方法およびそのための適応症
WO2009012283A1 (en)	2007-07-17	2009-01-22	Plexxikon Inc.	Compounds and methods for kinase modulation, and indications therefor
MY172424A (en)	2009-04-03	2019-11-25	Hoffmann La Roche	Propane- i-sulfonic acid {3- (4-chloro-phenyl)-1h-pyrrolo [2, 3-b] pyridine-3-carconyl] -2, 4-difluoro-phenyl} -amide compositions and uses thereof
US8329724B2 (en)	2009-08-03	2012-12-11	Hoffmann-La Roche Inc.	Process for the manufacture of pharmaceutically active compounds
CN106220623A (zh)	2009-11-06	2016-12-14	普莱希科公司	用于激酶调节的化合物和方法及其适应症
US9624213B2 (en)	2011-02-07	2017-04-18	Plexxikon Inc.	Compounds and methods for kinase modulation, and indications therefor
AR085279A1 (es)	2011-02-21	2013-09-18	Plexxikon Inc	Formas solidas de {3-[5-(4-cloro-fenil)-1h-pirrolo[2,3-b]piridina-3-carbonil]-2,4-difluor-fenil}-amida del acido propano-1-sulfonico
JO3407B1 (ar)	2012-05-31	2019-10-20	Eisai R&D Man Co Ltd	مركبات رباعي هيدرو بيرازولو بيريميدين
US9150570B2 (en)	2012-05-31	2015-10-06	Plexxikon Inc.	Synthesis of heterocyclic compounds
US9200005B2 (en) *	2013-03-13	2015-12-01	AbbVie Deutschland GmbH & Co. KG	Inhibitor compounds of phosphodiesterase type 10A
PL3060562T3 (pl) *	2013-10-21	2022-01-10	Genosco	Podstawione związki pirymidynowe i ich zastosowanie jako inhibitory syk

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3620860A1 (de) *	1986-06-21	1987-12-23	Basf Ag	Substituierte acrylsaeureester und fungizide, die diese verbindungen enthalten
WO1999029695A1 (en) *	1997-12-05	1999-06-17	Astrazeneca Uk Limited	Novel compounds
US6469014B1 (en) *	1997-05-28	2002-10-22	Astrazeneca Ab	Thieno[2,3-d] pyrimidinediones, their preparation and use in therapy
SE9702001D0 (sv) *	1997-05-28	1997-05-28	Astra Pharma Prod	Novel compounds
US6232320B1 (en) *	1998-06-04	2001-05-15	Abbott Laboratories	Cell adhesion-inhibiting antiinflammatory compounds
DE69912618T2 (de) *	1998-08-28	2004-10-28	Astrazeneca Ab	NEUE THIENO[2,3-d]PYRIMIDINDIONE, VERFAHREN FÜR IHRE HERSTELLUNG UND IHRE VERWENDUNG IN DER THERAPIE
GB0117583D0 (en)	2001-07-19	2001-09-12	Astrazeneca Ab	Novel compounds
GB0118479D0 (en) *	2001-07-28	2001-09-19	Astrazeneca Ab	Novel compounds
MXPA05007495A (es) *	2003-01-17	2005-09-21	Astrazeneca Ab	Tienopiridazinonas y su uso en la modulacion de enfermedades autoinmunes.
SE0300120D0 (sv) *	2003-01-17	2003-01-17	Astrazeneca Ab	Novel compounds
SE0300119D0 (sv) *	2003-01-17	2003-01-17	Astrazeneca Ab	Novel compounds

2003
- 2003-01-17 SE SE0300120A patent/SE0300120D0/xx unknown
2004
- 2004-01-15 CN CNB2004800071016A patent/CN100358900C/zh not_active Expired - Fee Related
- 2004-01-15 US US10/542,194 patent/US7064126B2/en not_active Expired - Fee Related
- 2004-01-15 PL PL378223A patent/PL378223A1/pl unknown
- 2004-01-15 MX MXPA05007494A patent/MXPA05007494A/es active IP Right Grant
- 2004-01-15 DE DE602004009407T patent/DE602004009407T2/de not_active Expired - Lifetime
- 2004-01-15 JP JP2006500749A patent/JP4589298B2/ja not_active Expired - Fee Related
- 2004-01-15 AU AU2004205617A patent/AU2004205617B2/en not_active Ceased
- 2004-01-15 RU RU2005121493/04A patent/RU2331646C2/ru not_active IP Right Cessation
- 2004-01-15 AT AT04702471T patent/ATE375352T1/de not_active IP Right Cessation
- 2004-01-15 UA UAA200506375A patent/UA80175C2/uk unknown
- 2004-01-15 KR KR1020057013124A patent/KR20050092759A/ko not_active Abandoned
- 2004-01-15 EP EP04702471A patent/EP1587809B1/de not_active Expired - Lifetime
- 2004-01-15 NZ NZ541216A patent/NZ541216A/en not_active IP Right Cessation
- 2004-01-15 WO PCT/SE2004/000051 patent/WO2004065393A1/en not_active Ceased
- 2004-01-15 ES ES04702471T patent/ES2293208T3/es not_active Expired - Lifetime
- 2004-01-15 BR BR0406780-0A patent/BRPI0406780A/pt not_active IP Right Cessation
- 2004-01-15 CA CA002512736A patent/CA2512736A1/en not_active Abandoned
2005
- 2005-06-23 IL IL169363A patent/IL169363A/en not_active IP Right Cessation
- 2005-06-29 ZA ZA200505273A patent/ZA200505273B/xx unknown
- 2005-08-15 IS IS7982A patent/IS2503B/is unknown
- 2005-08-15 NO NO20053827A patent/NO20053827L/no not_active Application Discontinuation
2006
- 2006-06-06 US US11/447,343 patent/US20060223809A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CN100358900C (zh)	2008-01-02
WO2004065393A1 (en)	2004-08-05
JP4589298B2 (ja)	2010-12-01
IS7982A (is)	2005-08-15
IL169363A0 (en)	2007-07-04
IS2503B (is)	2009-04-15
ATE375352T1 (de)	2007-10-15
ZA200505273B (en)	2006-04-26
US20060052380A1 (en)	2006-03-09
DE602004009407T2 (de)	2008-07-24
JP2006515373A (ja)	2006-05-25
SE0300120D0 (sv)	2003-01-17
MXPA05007494A (es)	2005-09-21
IL169363A (en)	2011-02-28
NO20053827D0 (no)	2005-08-15
BRPI0406780A (pt)	2006-01-17
DE602004009407D1 (de)	2007-11-22
NO20053827L (no)	2005-10-17
US7064126B2 (en)	2006-06-20
KR20050092759A (ko)	2005-09-22
ES2293208T3 (es)	2008-03-16
RU2005121493A (ru)	2006-02-20
HK1081958A1 (en)	2006-05-26
RU2331646C2 (ru)	2008-08-20
EP1587809B1 (de)	2007-10-10
EP1587809A1 (de)	2005-10-26
AU2004205617A1 (en)	2004-08-05
PL378223A1 (pl)	2006-03-20
CN1761670A (zh)	2006-04-19
NZ541216A (en)	2008-05-30
AU2004205617B2 (en)	2007-03-08
US20060223809A1 (en)	2006-10-05
CA2512736A1 (en)	2004-08-05

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UA80175C2 (en)	2007-08-27	Thienopyridazinones, process for their preparation and their use in the modulation of autoimmune disease
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DE69807741T2 (de)	2004-07-15	Neuartige verbindungen
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BR112016028845B1 (pt)	2023-04-04	Composto, composição farmacêutica e uso de um composto
JP2024500841A (ja)	2024-01-10	ｃＧＡＳと関連する病態の処置に有用なピロロ［３．２－ｂ］ピリジン誘導体
US20080221131A1 (en)	2008-09-11	Thienopyrimidinediones and their use in modulation of autoimmune disease
AU2001235985A1 (en)	2001-09-12	Thienopyridine derivatives and their use as anti-inflammatory agents
JP6770962B2 (ja)	2020-10-21	チアゾール誘導体の製造方法
JP2002255971A (ja)	2002-09-11	縮合複素環誘導体、その製造法および用途
CZ20002039A3 (cs)	2000-10-11	Nové pyridazinonové sloučeniny, způsob jejich přípravy a farmaceutický prostředek, který je obsahuje
HK1081958B (en)	2008-01-25	Thienopyridazinone derivative as modulators of autoimmune diseases