SK7352003A3 - Use of thienopyrimidines - Google Patents

Use of thienopyrimidines Download PDF

Info

Publication number: SK7352003A3
Authority: SK; Slovakia
Prior art keywords: pyrimidin; chloro; benzothieno; methoxybenzylamino; methyl
Prior art date: 2000-11-25

Application number

SK735-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Hans-Michael Eggenweiler

Volker Eiermann

Original Assignee

Merck Patent Gmbh

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.)

2000-11-25

Filing date

2001-10-29

Publication date

2003-11-04

2001-10-29 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2003-11-04 Publication of SK7352003A3 publication Critical patent/SK7352003A3/sk

Links

150000003839 salts Chemical class 0.000 claims abstract description 26
239000003814 drug Substances 0.000 claims abstract description 16
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206010002383 Angina Pectoris Diseases 0.000 claims abstract description 5
206010020772 Hypertension Diseases 0.000 claims abstract description 5
208000018262 Peripheral vascular disease Diseases 0.000 claims abstract description 5
208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 5
201000009961 allergic asthma Diseases 0.000 claims abstract description 5
208000006673 asthma Diseases 0.000 claims abstract description 5
206010006451 bronchitis Diseases 0.000 claims abstract description 5
208000023819 chronic asthma Diseases 0.000 claims abstract description 5
208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 5
201000006370 kidney failure Diseases 0.000 claims abstract description 5
206010019280 Heart failures Diseases 0.000 claims abstract description 4
206010028980 Neoplasm Diseases 0.000 claims abstract description 4
208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 4
208000012201 sexual and gender identity disease Diseases 0.000 claims abstract description 3
208000015891 sexual disease Diseases 0.000 claims abstract description 3
206010016654 Fibrosis Diseases 0.000 claims abstract 2
230000007882 cirrhosis Effects 0.000 claims abstract 2
210000004185 liver Anatomy 0.000 claims abstract 2
-1 3-chloro-4-methoxybenzylamino Chemical group 0.000 claims description 128
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 81
150000001875 compounds Chemical class 0.000 claims description 50
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 15
150000002169 ethanolamines Chemical class 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 13
125000002947 alkylene group Chemical group 0.000 claims description 12
239000012453 solvate Substances 0.000 claims description 12
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
235000019260 propionic acid Nutrition 0.000 claims description 10
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
230000002685 pulmonary effect Effects 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 4
210000000748 cardiovascular system Anatomy 0.000 claims description 4
PYHXQKPRNCIMHW-UHFFFAOYSA-N 5-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]pentanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCCCC(O)=O)=NC2=C1C(CCCC1)=C1S2 PYHXQKPRNCIMHW-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
230000000747 cardiac effect Effects 0.000 claims description 2
RFVAZPMINKWODA-UHFFFAOYSA-N 7-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]heptanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCCCCCC(O)=O)=NC2=C1C(CCCC1)=C1S2 RFVAZPMINKWODA-UHFFFAOYSA-N 0.000 claims 2
230000000172 allergic effect Effects 0.000 claims 2
208000010668 atopic eczema Diseases 0.000 claims 2
239000002085 irritant Substances 0.000 claims 2
231100000021 irritant Toxicity 0.000 claims 2
LYUPWDYILLXCBH-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]butanoic acid Chemical compound C1CCCC2=C1C1=C(NCC=3C=C4OCOC4=CC=3)N=C(CCCC(=O)O)N=C1S2 LYUPWDYILLXCBH-UHFFFAOYSA-N 0.000 claims 1
MWRPZZKSUQYFQF-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-6-methylthieno[2,3-d]pyrimidin-2-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(CNC2=C3C=C(SC3=NC(CCCC(O)=O)=N2)C)=C1 MWRPZZKSUQYFQF-UHFFFAOYSA-N 0.000 claims 1
IAYPBSUFZUDVCB-UHFFFAOYSA-N 4-[4-[(3-chloro-4-methoxyphenyl)methylamino]-6-methylthieno[2,3-d]pyrimidin-2-yl]butanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCCC(O)=O)=NC2=C1C=C(C)S2 IAYPBSUFZUDVCB-UHFFFAOYSA-N 0.000 claims 1
OGJAHBNONYXIQS-UHFFFAOYSA-N 5-[4-(1,3-benzodioxol-5-ylmethylamino)-6-methylthieno[2,3-d]pyrimidin-2-yl]pentanoic acid Chemical compound C1=C2OCOC2=CC(CNC2=C3C=C(SC3=NC(CCCCC(O)=O)=N2)C)=C1 OGJAHBNONYXIQS-UHFFFAOYSA-N 0.000 claims 1
IVKAATVWGBPOCV-UHFFFAOYSA-N 5-[4-[(3-chloro-4-methoxyphenyl)methylamino]-6-methylthieno[2,3-d]pyrimidin-2-yl]pentanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCCCC(O)=O)=NC2=C1C=C(C)S2 IVKAATVWGBPOCV-UHFFFAOYSA-N 0.000 claims 1
CQPWMZYGLYAPAX-UHFFFAOYSA-N 7-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]heptanoic acid Chemical compound C1CCCC2=C1C1=C(NCC=3C=C4OCOC4=CC=3)N=C(CCCCCCC(=O)O)N=C1S2 CQPWMZYGLYAPAX-UHFFFAOYSA-N 0.000 claims 1
VLMMGZBWBOJMQR-UHFFFAOYSA-M COC(C=CC(CNC1=NC(CCCCC([O-])=O)=NC2=C1C(CCCC1)=C1S2)=C1)=C1Cl.[Na+] Chemical compound COC(C=CC(CNC1=NC(CCCCC([O-])=O)=NC2=C1C(CCCC1)=C1S2)=C1)=C1Cl.[Na+] VLMMGZBWBOJMQR-UHFFFAOYSA-M 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
206010039085 Rhinitis allergic Diseases 0.000 abstract description 3
201000010105 allergic rhinitis Diseases 0.000 abstract description 3
206010003210 Arteriosclerosis Diseases 0.000 abstract 1
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206010008190 Cerebrovascular accident Diseases 0.000 abstract 1
208000006011 Stroke Diseases 0.000 abstract 1
208000011775 arteriosclerosis disease Diseases 0.000 abstract 1
208000002815 pulmonary hypertension Diseases 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 112
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 20
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 20
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 16
239000002253 acid Substances 0.000 description 14
229940070710 valerate Drugs 0.000 description 14
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
238000000034 method Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
239000003826 tablet Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 5
201000010099 disease Diseases 0.000 description 5
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
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125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
201000001881 impotence Diseases 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
XCCLUBXUFWORLI-UHFFFAOYSA-N methyl 3-(4-chloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)propanoate Chemical compound C1CCCC2=C1C1=C(Cl)N=C(CCC(=O)OC)N=C1S2 XCCLUBXUFWORLI-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
239000002590 phosphodiesterase V inhibitor Substances 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
229940005605 valeric acid Drugs 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
IUEZNVXQJJMXHB-UHFFFAOYSA-N 3-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]propanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCC(O)=O)=NC2=C1C(CCCC1)=C1S2 IUEZNVXQJJMXHB-UHFFFAOYSA-N 0.000 description 2
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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239000003086 colorant Substances 0.000 description 2
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230000008025 crystallization Effects 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
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238000001704 evaporation Methods 0.000 description 2
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238000010265 fast atom bombardment Methods 0.000 description 2
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PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
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235000019359 magnesium stearate Nutrition 0.000 description 2
LROMJHRXOSOPCW-UHFFFAOYSA-N methyl 3-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]propanoate Chemical compound C=12C=3CCCCC=3SC2=NC(CCC(=O)OC)=NC=1NCC1=CC=C(OC)C(Cl)=C1 LROMJHRXOSOPCW-UHFFFAOYSA-N 0.000 description 2
CXGOXWWHIFQDJI-UHFFFAOYSA-N methyl 7-(4-chloro-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=NC(Cl)=C2C(C)=C(C)SC2=N1 CXGOXWWHIFQDJI-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
230000012191 relaxation of muscle Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
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 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
150000003577 thiophenes Chemical group 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- 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
- A61P27/06—Antiglaucoma agents or miotics
- 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
- A61P37/08—Antiallergic 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
- 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
- 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
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Endocrinology (AREA)
Ophthalmology & Optometry (AREA)
Urology & Nephrology (AREA)
Reproductive Health (AREA)
Epidemiology (AREA)
Vascular Medicine (AREA)
Immunology (AREA)
Gastroenterology & Hepatology (AREA)
Gynecology & Obstetrics (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK735-2003A 2000-11-25 2001-10-29 Use of thienopyrimidines SK7352003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10058663A DE10058663A1 (de)	2000-11-25	2000-11-25	Verwendung von Thienopyrimidinen
PCT/EP2001/012494 WO2002041896A2 (de)	2000-11-25	2001-10-29	Verwendung von thienopyrimidinen

Publications (1)

Publication Number	Publication Date
SK7352003A3 true SK7352003A3 (en)	2003-11-04

Family

ID=7664711

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK735-2003A SK7352003A3 (en)	2000-11-25	2001-10-29	Use of thienopyrimidines

Country Status (18)

Country	Link
US (1)	US20040034040A1 (pt)
EP (1)	EP1337256A2 (pt)
JP (1)	JP2004513966A (pt)
KR (1)	KR20030051867A (pt)
CN (1)	CN1474693A (pt)
AR (1)	AR032482A1 (pt)
AU (1)	AU2002224808A1 (pt)
BR (1)	BR0115247A (pt)
CA (1)	CA2429647A1 (pt)
CZ (1)	CZ20031618A3 (pt)
DE (1)	DE10058663A1 (pt)
HU (1)	HUP0400818A2 (pt)
MX (1)	MXPA03004582A (pt)
PL (1)	PL361277A1 (pt)
RU (1)	RU2003117478A (pt)
SK (1)	SK7352003A3 (pt)
WO (1)	WO2002041896A2 (pt)
ZA (1)	ZA200304909B (pt)

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US7238701B2 (en) *	2003-07-24	2007-07-03	Bayer Pharmaceuticals Corporation	Substituted tetrahydrobenzothienopyrimidinamine compounds useful for treating hyper-proliferative disorders
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TW200845978A (en)	2007-03-07	2008-12-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives
TW200900065A (en)	2007-03-07	2009-01-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives
US8252937B2 (en)	2007-09-14	2012-08-28	Janssen Pharmaceuticals, Inc.	1,3-disubstituted 4-(aryl-X-phenyl)-1H-pyridin-2-ones
PL2203439T3 (pl)	2007-09-14	2011-06-30	Addex Pharmaceuticals Sa	1',3'-dipodstawione-4-fenylo-3,4,5,6-tetrahydro-2H, 1'H-[1, 4']bipirydynylo-2'-ketony
US8722894B2 (en)	2007-09-14	2014-05-13	Janssen Pharmaceuticals, Inc.	1,3-disubstituted-4-phenyl-1H-pyridin-2-ones
RU2492170C9 (ru)	2007-11-14	2013-12-27	Орто-Макнейл-Янссен Фармасьютикалз, Инк.	Имидазо[1,2-а]пиридиновые производные и их применение в качестве положительных аллостерических модуляторов рецепторов mglur2
JP5547194B2 (ja)	2008-09-02	2014-07-09	ジャンセンファーマシューティカルズ，インコーポレイテッド．	代謝型グルタミン酸受容体の調節因子としての３−アザビシクロ［３．１．０］ヘキシル誘導体
RU2517181C2 (ru)	2008-10-16	2014-05-27	Орто-Макнейл-Янссен Фармасьютикалз, Инк.	Производные индола и бензоморфолина в качестве модулятора метаботропных глутаматных рецепторов
WO2010060589A1 (en)	2008-11-28	2010-06-03	Ortho-Mcneil-Janssen Pharmaceuticals, Inc.	Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors
MY153912A (en)	2009-05-12	2015-04-15	Janssen Pharmaceuticals Inc	1, 2, 4,-triazolo[4,3-a[pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
MY153913A (en)	2009-05-12	2015-04-15	Janssen Pharmaceuticals Inc	7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
CN102439008B (zh)	2009-05-12	2015-04-29	杨森制药有限公司	1,2,4-三唑并[4,3-a]吡啶衍生物及其用于治疗或预防神经和精神病症的用途
CN103261195B (zh)	2010-11-08	2015-09-02	杨森制药公司	1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途
EP2661435B1 (en)	2010-11-08	2015-08-19	Janssen Pharmaceuticals, Inc.	1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
PL2649069T3 (pl)	2010-11-08	2016-01-29	Janssen Pharmaceuticals Inc	Pochodne 1,2,4-triazolo[4,3-a]pirydyny i ich zastosowanie jako dodatnich allosterycznych modulatorów receptorów mGluR2
MX2014000648A (es)	2011-07-19	2014-09-25	Infinity Pharmaceuticals Inc	Compuestos heterociclicos y sus usos.
JO3368B1 (ar)	2013-06-04	2019-03-13	Janssen Pharmaceutica Nv	مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2
JO3367B1 (ar)	2013-09-06	2019-03-13	Janssen Pharmaceutica Nv	مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2
KR20220049612A (ko)	2014-01-21	2022-04-21	얀센 파마슈티카 엔.브이.	대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도
HUE053734T2 (hu)	2014-01-21	2021-07-28	Janssen Pharmaceutica Nv	2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait tartalmazó kombinációk és alkalmazásuk
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2000
- 2000-11-25 DE DE10058663A patent/DE10058663A1/de not_active Withdrawn
2001
- 2001-10-29 US US10/432,778 patent/US20040034040A1/en not_active Abandoned
- 2001-10-29 WO PCT/EP2001/012494 patent/WO2002041896A2/de not_active Ceased
- 2001-10-29 CA CA002429647A patent/CA2429647A1/en not_active Abandoned
- 2001-10-29 HU HU0400818A patent/HUP0400818A2/hu unknown
- 2001-10-29 JP JP2002544074A patent/JP2004513966A/ja active Pending
- 2001-10-29 MX MXPA03004582A patent/MXPA03004582A/es unknown
- 2001-10-29 SK SK735-2003A patent/SK7352003A3/sk unknown
- 2001-10-29 RU RU2003117478/15A patent/RU2003117478A/ru not_active Application Discontinuation
- 2001-10-29 EP EP01994626A patent/EP1337256A2/de not_active Withdrawn
- 2001-10-29 CZ CZ20031618A patent/CZ20031618A3/cs unknown
- 2001-10-29 BR BR0115247-5A patent/BR0115247A/pt not_active Application Discontinuation
- 2001-10-29 AU AU2002224808A patent/AU2002224808A1/en not_active Abandoned
- 2001-10-29 PL PL01361277A patent/PL361277A1/xx unknown
- 2001-10-29 KR KR10-2003-7006921A patent/KR20030051867A/ko not_active Withdrawn
- 2001-10-29 CN CNA018191800A patent/CN1474693A/zh active Pending
- 2001-11-23 AR ARP010105462A patent/AR032482A1/es unknown
2003
- 2003-06-24 ZA ZA200304909A patent/ZA200304909B/en unknown

Also Published As

Publication number	Publication date
WO2002041896A2 (de)	2002-05-30
MXPA03004582A (es)	2003-09-04
AU2002224808A1 (en)	2002-06-03
KR20030051867A (ko)	2003-06-25
PL361277A1 (en)	2004-10-04
ZA200304909B (en)	2004-08-25
EP1337256A2 (de)	2003-08-27
CZ20031618A3 (cs)	2003-10-15
JP2004513966A (ja)	2004-05-13
WO2002041896A3 (de)	2002-10-31
DE10058663A1 (de)	2002-05-29
CA2429647A1 (en)	2002-05-30
CN1474693A (zh)	2004-02-11
BR0115247A (pt)	2003-08-12
HUP0400818A2 (hu)	2004-07-28
RU2003117478A (ru)	2004-11-27
US20040034040A1 (en)	2004-02-19
AR032482A1 (es)	2003-11-12

Publication	Publication Date	Title
SK7352003A3 (en)	2003-11-04	Use of thienopyrimidines
US6495554B2 (en)	2002-12-17	Thienopyrimidines
AU767273B2 (en)	2003-11-06	Thienopyrimidines as phosphodiesterase inhibitors
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