SK168499A3 - 3-substituted 3,4 dihydro-thieno[2,3-d]pyrimidine derivatives and production and use of the same - Google Patents

3-substituted 3,4 dihydro-thieno[2,3-d]pyrimidine derivatives and production and use of the same Download PDF

Info

Publication number: SK168499A3
Authority: SK; Slovakia
Prior art keywords: methyl; dihydro; thieno; pyrimidin; ethyl
Prior art date: 1997-06-13

Application number

SK1684-99A

Other languages

English (en)

Slovak (sk)

Inventor

Gerd Steiner

Uta Dullweber

Dorothea Starck

Alfred Bach

Karsten Wicke

Hans-Jurgen Teschendorf

Francisco Javier Garcia-Ladona

Franz Emling

Original Assignee

Basf Ag

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.)

1997-06-13

Filing date

1998-05-29

Publication date

2000-05-16

1998-05-29 Application filed by Basf Ag filed Critical Basf Ag

2000-05-16 Publication of SK168499A3 publication Critical patent/SK168499A3/sk

Links

-1 3-substituted 3,4 dihydro-thieno[2,3-d]pyrimidine Chemical class 0.000 title claims abstract description 35
238000004519 manufacturing process Methods 0.000 title claims description 3
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 7
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 19
229940076279 serotonin Drugs 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
230000009103 reabsorption Effects 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
208000020401 Depressive disease Diseases 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
230000005764 inhibitory process Effects 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000003727 serotonin 1A antagonist Substances 0.000 claims description 2
230000008485 antagonism Effects 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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238000003756 stirring Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000000935 antidepressant agent Substances 0.000 description 4
229940005513 antidepressants Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
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239000003960 organic solvent Substances 0.000 description 4
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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235000011152 sodium sulphate Nutrition 0.000 description 3
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239000007858 starting material Substances 0.000 description 3
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WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
HJBJQQHJMBEFNA-UHFFFAOYSA-N 3-(2-chloroethyl)-n,n,5-trimethyl-4-oxothieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=CN(CCCl)C(=O)C2=C1SC(C(=O)N(C)C)=C2C HJBJQQHJMBEFNA-UHFFFAOYSA-N 0.000 description 2
RLGSCQDEXRFBNS-UHFFFAOYSA-N 3-(2-hydroxyethyl)-n,n,5-trimethyl-4-oxothieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=CN(CCO)C(=O)C2=C1SC(C(=O)N(C)C)=C2C RLGSCQDEXRFBNS-UHFFFAOYSA-N 0.000 description 2
JEDVKUHCDPPWNR-UHFFFAOYSA-N 3h-thieno[2,3-d]pyrimidin-4-one Chemical compound O=C1NC=NC2=C1C=CS2 JEDVKUHCDPPWNR-UHFFFAOYSA-N 0.000 description 2
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230000037396 body weight Effects 0.000 description 2
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TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
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239000006071 cream Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
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125000004185 ester group Chemical group 0.000 description 1
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VOFMVGKEJXTNCQ-UHFFFAOYSA-N ethyl 2-amino-5-(dimethylcarbamoyl)-4-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC(C(=O)N(C)C)=C1C VOFMVGKEJXTNCQ-UHFFFAOYSA-N 0.000 description 1
NQZDSKAMKJVOMW-UHFFFAOYSA-N ethyl 2-amino-5-(dimethylcarbamoyl)-5-methyl-2h-thiophene-3-carboxylate Chemical compound CCOC(=O)C1=CC(C)(C(=O)N(C)C)SC1N NQZDSKAMKJVOMW-UHFFFAOYSA-N 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
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150000005826 halohydrocarbons Chemical class 0.000 description 1
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230000002401 inhibitory effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
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230000006984 memory degeneration Effects 0.000 description 1
208000023060 memory loss Diseases 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
KFOPKOFKGJJEBW-ZSSYTAEJSA-N methyl 2-[(1s,7r,8s,9s,10r,13r,14s,17r)-1,7-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]acetate Chemical compound C([C@H]1O)C2=CC(=O)C[C@H](O)[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC(=O)OC)[C@@]1(C)CC2 KFOPKOFKGJJEBW-ZSSYTAEJSA-N 0.000 description 1
230000004899 motility Effects 0.000 description 1
UWEPBKQSRBGRKA-UHFFFAOYSA-N n,n,5-trimethyl-3-[2-(4-naphthalen-1-ylpiperazin-1-yl)ethyl]-4-oxothieno[2,3-d]pyrimidine-6-carboxamide Chemical compound C1=CC=C2C(N3CCN(CC3)CCN3C=NC=4SC(=C(C=4C3=O)C)C(=O)N(C)C)=CC=CC2=C1 UWEPBKQSRBGRKA-UHFFFAOYSA-N 0.000 description 1
FASHPBRQNGGLFP-UHFFFAOYSA-N n,n,5-trimethyl-3-[2-(4-naphthalen-1-ylpiperidin-1-yl)ethyl]-4-oxothieno[2,3-d]pyrimidine-6-carboxamide Chemical compound C1=CC=C2C(C3CCN(CC3)CCN3C=NC=4SC(=C(C=4C3=O)C)C(=O)N(C)C)=CC=CC2=C1 FASHPBRQNGGLFP-UHFFFAOYSA-N 0.000 description 1
NPKKGWGXXOOTNH-UHFFFAOYSA-N n,n,5-trimethyl-3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-4-oxothieno[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1C=2C(C)=C(C(=O)N(C)C)SC=2N=CN1CCN(CC1)CCN1C1=CC=CC=C1C NPKKGWGXXOOTNH-UHFFFAOYSA-N 0.000 description 1
PIQWXARZZCBWFP-UHFFFAOYSA-N n,n,5-trimethyl-4-oxo-3-[2-(4-pyridin-2-ylpiperazin-1-yl)ethyl]thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1C=2C(C)=C(C(=O)N(C)C)SC=2N=CN1CCN(CC1)CCN1C1=CC=CC=N1 PIQWXARZZCBWFP-UHFFFAOYSA-N 0.000 description 1
ONVXSSZJXDPWNC-UHFFFAOYSA-N n,n,5-trimethyl-4-oxo-3-[2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1C=2C(C)=C(C(=O)N(C)C)SC=2N=CN1CCN(CC1)CCN1C1=NC=CC=N1 ONVXSSZJXDPWNC-UHFFFAOYSA-N 0.000 description 1
FIIJBVBIBLPBDU-UHFFFAOYSA-N n,n,5-trimethyl-4-oxo-3-[2-(4-quinazolin-4-ylpiperazin-1-yl)ethyl]thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound C1=CC=C2C(N3CCN(CC3)CCN3C=NC=4SC(=C(C=4C3=O)C)C(=O)N(C)C)=NC=NC2=C1 FIIJBVBIBLPBDU-UHFFFAOYSA-N 0.000 description 1
QWOKFGQGYWLWRP-UHFFFAOYSA-N n,n,5-trimethyl-4-oxo-3-[2-[4-(5,6,7,8-tetrahydronaphthalen-1-yl)piperazin-1-yl]ethyl]thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound C1CCCC2=C1C=CC=C2N(CC1)CCN1CCN1C=NC(SC(=C2C)C(=O)N(C)C)=C2C1=O QWOKFGQGYWLWRP-UHFFFAOYSA-N 0.000 description 1
PLSWKLWKNFLBFC-UHFFFAOYSA-N n,n,5-trimethyl-4-oxo-3-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1C=2C(C)=C(C(=O)N(C)C)SC=2N=CN1CCN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 PLSWKLWKNFLBFC-UHFFFAOYSA-N 0.000 description 1
BFQYVGOYWUGPAJ-UHFFFAOYSA-N n,n-diethyl-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-5-methyl-4-oxothieno[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1C=2C(C)=C(C(=O)N(CC)CC)SC=2N=CN1CCN(CC1)CCN1C1=CC=CC=C1OC BFQYVGOYWUGPAJ-UHFFFAOYSA-N 0.000 description 1
SWBLQWYHCNJGMH-UHFFFAOYSA-N n,n-diethyl-5-methyl-3-[2-(4-naphthalen-1-ylpiperazin-1-yl)ethyl]-4-oxothieno[2,3-d]pyrimidine-6-carboxamide Chemical compound C1=CC=C2C(N3CCN(CC3)CCN3C=NC=4SC(=C(C=4C3=O)C)C(=O)N(CC)CC)=CC=CC2=C1 SWBLQWYHCNJGMH-UHFFFAOYSA-N 0.000 description 1
IURUXISVEIKINP-UHFFFAOYSA-N n,n-diethyl-5-methyl-4-oxo-3-[2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1C=2C(C)=C(C(=O)N(CC)CC)SC=2N=CN1CCN(CC1)CCN1C1=NC=CC=N1 IURUXISVEIKINP-UHFFFAOYSA-N 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960002296 paroxetine Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
210000000063 presynaptic terminal Anatomy 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000003380 propellant Substances 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
230000001107 psychogenic effect Effects 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
230000001932 seasonal effect Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
208000012201 sexual and gender identity disease Diseases 0.000 description 1
208000015891 sexual disease Diseases 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK1684-99A 1997-06-13 1998-05-29 3-substituted 3,4 dihydro-thieno[2,3-d]pyrimidine derivatives and production and use of the same SK168499A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19724980A DE19724980A1 (de)	1997-06-13	1997-06-13	3-Substituierte 3,4-Dihydro-thieno[2,3-d]pyrimidin-Derivate, ihre Herstellung und Verwendung
PCT/EP1998/003230 WO1998056792A1 (fr)	1997-06-13	1998-05-29	Derives de 3,4-dihydro-thieno[2,3-d]pyrimidine 3-substitues, leur preparation et leur utilisation

Publications (1)

Publication Number	Publication Date
SK168499A3 true SK168499A3 (en)	2000-05-16

Family

ID=7832352

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1684-99A SK168499A3 (en)	1997-06-13	1998-05-29	3-substituted 3,4 dihydro-thieno[2,3-d]pyrimidine derivatives and production and use of the same

Country Status (25)

Country	Link
US (1)	US6159962A (fr)
EP (1)	EP0988306B1 (fr)
JP (1)	JP2002504103A (fr)
KR (1)	KR20010013696A (fr)
CN (1)	CN1260797A (fr)
AR (1)	AR015712A1 (fr)
AT (1)	ATE244720T1 (fr)
AU (1)	AU749320B2 (fr)
BG (1)	BG103900A (fr)
BR (1)	BR9810017A (fr)
CA (1)	CA2293816A1 (fr)
CO (1)	CO4940507A1 (fr)
CZ (1)	CZ290464B6 (fr)
DE (2)	DE19724980A1 (fr)
HR (1)	HRP980319A2 (fr)
HU (1)	HUP0002902A3 (fr)
ID (1)	ID23421A (fr)
IL (1)	IL132967A0 (fr)
NO (1)	NO996043L (fr)
NZ (1)	NZ502238A (fr)
PL (1)	PL337453A1 (fr)
SK (1)	SK168499A3 (fr)
TR (1)	TR199903062T2 (fr)
WO (1)	WO1998056792A1 (fr)
ZA (1)	ZA985121B (fr)

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DE69842058D1 (de) *	1997-10-27	2011-01-27	Neurosearch As	Heteroaryl Diazacycloalkane als cholinergische Ligande für Nikotin-Acetylcholin-Rezeptoren
DE19900545A1 (de) *	1999-01-11	2000-07-13	Basf Ag	Verwendung von Pyrimidinderivaten zur Prophylaxe und Therapie der zerebralen Ischämie
AU2001234188A1 (en) *	2000-02-29	2001-09-12	Takeda Chemical Industries Ltd.	Processes for the production of thienopyrimidine derivatives
DE10031389A1 (de) *	2000-07-03	2002-01-17	Knoll Ag	Pyrimidinderivate und ihre Verwendung zur Prophylaxe und Therapie der zerebralen Ischämie
DE10259382A1 (de) *	2002-12-18	2004-07-01	Abbott Gmbh & Co. Kg	3-Substituierte 3,4-Dihydro-thieno[2,3-d]pyrimidin-4-on-Derivate, ihre Herstellung und Verwendung
EP1622914B1 (fr) *	2003-03-31	2011-06-01	Trovis Pharmaceuticals LLC	Nouveaux composes de piperidinylamino-thieno[2,3-d] pyrimidine
US7612078B2 (en) *	2003-03-31	2009-11-03	Epix Delaware, Inc.	Piperidinylamino-thieno[2,3-D] pyrimidine compounds
US20050222175A1 (en) *	2004-03-31	2005-10-06	Dhanoa Dale S	New piperidinylamino-thieno[2,3-D] pyrimidine compounds
US7488736B2 (en) *	2004-05-17	2009-02-10	Epix Delaware, Inc.	Thienopyridinone compounds and methods of treatment
US7407966B2 (en) *	2004-10-07	2008-08-05	Epix Delaware, Inc.	Thienopyridinone compounds and methods of treatment
US7576211B2 (en) *	2004-09-30	2009-08-18	Epix Delaware, Inc.	Synthesis of thienopyridinone compounds and related intermediates
US7598265B2 (en) *	2004-09-30	2009-10-06	Epix Delaware, Inc.	Compositions and methods for treating CNS disorders
CA2914168C (fr)	2006-03-28	2018-05-08	Atir Holding S.A.	Derives de pyrido[1,2-a]pyrimidin-4-one et leur utilisation pour le traitement de troubles sexuels
WO2008117269A2 (fr) *	2007-03-28	2008-10-02	Atir Holding S.A.	Composés hétérocycliques comme agents sérotoninergiques et dopaminergiques et leurs utilisations
CA2685753A1 (fr) *	2007-05-09	2008-11-20	Neuromed Pharmaceuticals Ltd.	Derives bicycliques de pyrimidine en tant que bloqueurs des canaux calciques
EP2445877B1 (fr) *	2008-12-03	2014-07-23	Nanotherapeutics, Inc.	Composés bicycliques et leurs procédés de fabrication et d'utilisation
EP2471791B1 (fr) *	2009-08-26	2014-11-12	Takeda Pharmaceutical Company Limited	Dérivé d'hétérocycle condensé et son utilisation
WO2012140642A1 (fr)	2011-04-10	2012-10-18	Atir Holding S.A.	Composés hétérocycliques et leurs utilisations dans le traitement de troubles sexuels
US9671052B2 (en)	2015-10-27	2017-06-06	Whirlpool Corporation	Collet securing device for joining two fluid lines and providing lateral support at the connection of the two fluid lines
US10557469B2 (en)	2016-03-22	2020-02-11	Whirlpool Corporation	Multi-outlet fluid flow system for an appliance incorporating a bi-directional motor
US10655266B2 (en)	2016-11-30	2020-05-19	Whirlpool Corporation	Lint processing fluid pump for a laundry appliance
US10662574B2 (en)	2017-02-27	2020-05-26	Whirlpool Corporation	Self cleaning heater exchanger plate
US10480117B2 (en)	2017-02-27	2019-11-19	Whirlpool Corporation	Self cleaning sump cover
US10619289B2 (en)	2017-02-27	2020-04-14	Whirlpool Corporation	Self cleaning diverter valve
US10634412B2 (en)	2017-04-10	2020-04-28	Whirlpool Corporation	Concealed upstream air tower guide vanes
WO2020183011A1 (fr)	2019-03-14	2020-09-17	Institut Curie	Inhibiteurs de htr1d et leurs utilisations dans le traitement du cancer

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US5001130A (en) *	1988-02-18	1991-03-19	Bristol-Myers Company	Psychotropic heterobicycloalkylpiperazine derivatives
US4835157A (en) *	1988-03-15	1989-05-30	Ortho Pharmaceutical Corporation	Thieno- and furopyrimidine-2,4-dione piperidine derivatives as serotonin antagonists and alpha adrenergic blocking agents
DE19636769A1 (de) *	1996-09-10	1998-03-12	Basf Ag	3-Substituierte Pyrido [4',3':4,5]thieno[2,3-d]pyrimidin-Derivate, ihre Herstellung und Verwendung

1997
- 1997-06-13 DE DE19724980A patent/DE19724980A1/de not_active Withdrawn
1998
- 1998-05-28 ID IDW991496A patent/ID23421A/id unknown
- 1998-05-29 DE DE59808992T patent/DE59808992D1/de not_active Expired - Fee Related
- 1998-05-29 SK SK1684-99A patent/SK168499A3/sk unknown
- 1998-05-29 WO PCT/EP1998/003230 patent/WO1998056792A1/fr not_active Ceased
- 1998-05-29 AU AU79176/98A patent/AU749320B2/en not_active Ceased
- 1998-05-29 PL PL98337453A patent/PL337453A1/xx not_active Application Discontinuation
- 1998-05-29 AT AT98929405T patent/ATE244720T1/de not_active IP Right Cessation
- 1998-05-29 CN CN98806146A patent/CN1260797A/zh active Pending
- 1998-05-29 HU HU0002902A patent/HUP0002902A3/hu unknown
- 1998-05-29 JP JP50145899A patent/JP2002504103A/ja active Pending
- 1998-05-29 CZ CZ19994431A patent/CZ290464B6/cs not_active IP Right Cessation
- 1998-05-29 BR BR9810017-3A patent/BR9810017A/pt not_active IP Right Cessation
- 1998-05-29 TR TR1999/03062T patent/TR199903062T2/xx unknown
- 1998-05-29 IL IL13296798A patent/IL132967A0/xx unknown
- 1998-05-29 KR KR1019997011711A patent/KR20010013696A/ko not_active Withdrawn
- 1998-05-29 CA CA002293816A patent/CA2293816A1/fr not_active Abandoned
- 1998-05-29 EP EP98929405A patent/EP0988306B1/fr not_active Expired - Lifetime
- 1998-05-29 NZ NZ502238A patent/NZ502238A/xx unknown
- 1998-05-29 US US09/445,222 patent/US6159962A/en not_active Expired - Lifetime
- 1998-06-11 AR ARP980102769A patent/AR015712A1/es not_active Application Discontinuation
- 1998-06-11 CO CO98033545A patent/CO4940507A1/es unknown
- 1998-06-12 ZA ZA9805121A patent/ZA985121B/xx unknown
- 1998-06-12 HR HR19724980.9A patent/HRP980319A2/hr not_active Application Discontinuation
1999
- 1999-11-17 BG BG103900A patent/BG103900A/xx unknown
- 1999-12-08 NO NO996043A patent/NO996043L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CO4940507A1 (es)	2000-07-24
NO996043D0 (no)	1999-12-08
KR20010013696A (ko)	2001-02-26
NZ502238A (en)	2001-02-23
TR199903062T2 (xx)	2000-06-21
BG103900A (en)	2000-06-30
ID23421A (id)	2000-04-20
DE19724980A1 (de)	1998-12-17
AU749320B2 (en)	2002-06-20
AU7917698A (en)	1998-12-30
HUP0002902A2 (hu)	2001-02-28
US6159962A (en)	2000-12-12
CA2293816A1 (fr)	1998-12-17
ATE244720T1 (de)	2003-07-15
ZA985121B (en)	1999-12-13
PL337453A1 (en)	2000-08-14
HUP0002902A3 (en)	2002-09-30
EP0988306A1 (fr)	2000-03-29
BR9810017A (pt)	2000-09-19
CZ290464B6 (cs)	2002-07-17
JP2002504103A (ja)	2002-02-05
CN1260797A (zh)	2000-07-19
WO1998056792A1 (fr)	1998-12-17
HRP980319A2 (en)	1999-04-30
EP0988306B1 (fr)	2003-07-09
NO996043L (no)	1999-12-08
AR015712A1 (es)	2001-05-16
CZ443199A3 (cs)	2000-06-14
DE59808992D1 (de)	2003-08-14
IL132967A0 (en)	2001-03-19

Publication	Publication Date	Title
US6159962A (en)	2000-12-12	3-substituted 3,4-dihydro-thieno[2,3-D]pyrimidine derivatives and production and use of the same
SK283039B6 (sk)	2003-02-04	3-Substituované 3,4,5,6,7,8-hexahydropyrido [4',3':4,5] tieno [2,3-d]-pyrimidínové deriváty a ich použitie
US6355647B1 (en)	2002-03-12	3-substituted 3,4,5,7-tetrahedropyrrolo[3′,4′:4,5]thieno-[2,3-d]pyrimidine derivatives, their preparation and use
NZ503486A (en)	2001-04-27	Serotonin antagonists 3-substituted tetrahydropyridopyrimidinone derivatives for treating 5HT, depression and related disorders
US6159981A (en)	2000-12-12	3-substituted pyrido [3',4':4,5] Thieno [2,3-d] pyrimidine derivatives, and production and use of the same
MXPA99010622A (en)	2000-09-04	3-substituted 3,4 dihydro-thieno[2, 3-d]pyrimidine derivatives and production and use of the same
MXPA99010621A (en)	2000-09-04	3-substituted pyrido [3',4':4,5]thieno [2,3-d]pyrimidine derivatives, and production and use of the same
MXPA00001119A (en)	2001-05-07	3-substituted 3,4,5,7-tetrahydro-pyrrolo3',4':4,5 thieno2,3-dpyrimidine derivatives, their preparation and use as 5ht antagonists
CZ448399A3 (cs)	2000-04-12	3-substituované deriváty pyrido[3',4':4,5] thieno[2,3-d] pyrimidinu, jejich výroba a použití