HRP980318A2 - 3-SUBSTITUTED PYRIDO /3', 4' : 4,5/THIENO/2,3-d/ PYRIMIDINE DERIVATIVES, AND PREPARATION AND USE THEREOF - Google Patents
3-SUBSTITUTED PYRIDO /3', 4' : 4,5/THIENO/2,3-d/ PYRIMIDINE DERIVATIVES, AND PREPARATION AND USE THEREOFInfo
- Publication number
- HRP980318A2 HRP980318A2 HR19724979.5A HRP980318A HRP980318A2 HR P980318 A2 HRP980318 A2 HR P980318A2 HR P980318 A HRP980318 A HR P980318A HR P980318 A2 HRP980318 A2 HR P980318A2
- Authority
- HR
- Croatia
- Prior art keywords
- ethyl
- thieno
- substituted
- pyrido
- naphthyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
- -1 trifluoromethoxy, hydroxy Chemical group 0.000 claims description 42
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229940076279 serotonin Drugs 0.000 claims description 12
- 102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 101710138639 5-hydroxytryptamine receptor 1B Proteins 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 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
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
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- 230000000697 serotonin reuptake Effects 0.000 claims description 2
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000008485 antagonism Effects 0.000 claims 1
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- 238000002844 melting Methods 0.000 description 13
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- 239000000047 product Substances 0.000 description 12
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- 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
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 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
- 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 210000000063 presynaptic terminal Anatomy 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
- 210000001609 raphe nuclei Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 150000003335 secondary amines Chemical class 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
- 230000011664 signaling Effects 0.000 description 1
- 208000019116 sleep 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
- 239000000829 suppository Substances 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
- 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
- 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
- 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
- C07D495/12—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 three hetero rings
- C07D495/14—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19724979A DE19724979A1 (de) | 1997-06-13 | 1997-06-13 | 3-substituierte Pyrido [3,4,5]thieno[2,3-d]pyrimidin-Derivate, ihre Herstellung und Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980318A2 true HRP980318A2 (en) | 1999-04-30 |
Family
ID=7832351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR19724979.5A HRP980318A2 (en) | 1997-06-13 | 1998-06-12 | 3-SUBSTITUTED PYRIDO /3', 4' : 4,5/THIENO/2,3-d/ PYRIMIDINE DERIVATIVES, AND PREPARATION AND USE THEREOF |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6159981A (ko) |
| EP (1) | EP1023296B1 (ko) |
| JP (1) | JP2002504104A (ko) |
| KR (1) | KR20010013698A (ko) |
| CN (1) | CN1259954A (ko) |
| AR (1) | AR014354A1 (ko) |
| AT (1) | ATE256686T1 (ko) |
| AU (1) | AU748697B2 (ko) |
| BG (1) | BG103921A (ko) |
| BR (1) | BR9810008A (ko) |
| CA (1) | CA2293440A1 (ko) |
| CO (1) | CO4940481A1 (ko) |
| DE (2) | DE19724979A1 (ko) |
| ES (1) | ES2215312T3 (ko) |
| HR (1) | HRP980318A2 (ko) |
| HU (1) | HUP0002736A3 (ko) |
| ID (1) | ID24045A (ko) |
| IL (1) | IL132985A0 (ko) |
| MY (1) | MY132993A (ko) |
| NO (1) | NO996045L (ko) |
| NZ (1) | NZ502237A (ko) |
| PL (1) | PL337454A1 (ko) |
| SK (1) | SK174399A3 (ko) |
| TR (1) | TR199903061T2 (ko) |
| TW (1) | TW479059B (ko) |
| WO (1) | WO1998056793A1 (ko) |
| ZA (1) | ZA985120B (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19900673A1 (de) * | 1999-01-11 | 2000-07-13 | Basf Ag | Verwendung von Bindungspartnern für 5-HT5-Rezeptoren zur Behandlung neurodegenerativer und neuropsychiatrischer Störungen |
| DE19900545A1 (de) | 1999-01-11 | 2000-07-13 | Basf Ag | Verwendung von Pyrimidinderivaten zur Prophylaxe und Therapie der zerebralen Ischämie |
| 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 |
| US8877316B2 (en) * | 2002-12-20 | 2014-11-04 | The Procter & Gamble Company | Cloth-like personal care articles |
| MX2009008507A (es) | 2007-02-07 | 2009-08-20 | Astellas Pharma Inc | Derivado de acilguanidina. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 DE19724979A patent/DE19724979A1/de not_active Withdrawn
-
1998
- 1998-05-29 JP JP50145999A patent/JP2002504104A/ja active Pending
- 1998-05-29 SK SK1743-99A patent/SK174399A3/sk unknown
- 1998-05-29 PL PL98337454A patent/PL337454A1/xx not_active Application Discontinuation
- 1998-05-29 NZ NZ502237A patent/NZ502237A/en unknown
- 1998-05-29 EP EP98936299A patent/EP1023296B1/de not_active Expired - Lifetime
- 1998-05-29 ES ES98936299T patent/ES2215312T3/es not_active Expired - Lifetime
- 1998-05-29 HU HU0002736A patent/HUP0002736A3/hu unknown
- 1998-05-29 WO PCT/EP1998/003231 patent/WO1998056793A1/de not_active Application Discontinuation
- 1998-05-29 BR BR9810008-4A patent/BR9810008A/pt not_active IP Right Cessation
- 1998-05-29 DE DE59810485T patent/DE59810485D1/de not_active Expired - Fee Related
- 1998-05-29 TR TR1999/03061T patent/TR199903061T2/xx unknown
- 1998-05-29 US US09/445,178 patent/US6159981A/en not_active Expired - Lifetime
- 1998-05-29 AU AU85357/98A patent/AU748697B2/en not_active Ceased
- 1998-05-29 IL IL13298598A patent/IL132985A0/xx unknown
- 1998-05-29 CA CA002293440A patent/CA2293440A1/en not_active Abandoned
- 1998-05-29 ID IDW991495A patent/ID24045A/id unknown
- 1998-05-29 CN CN98806104A patent/CN1259954A/zh active Pending
- 1998-05-29 AT AT98936299T patent/ATE256686T1/de not_active IP Right Cessation
- 1998-05-29 KR KR1019997011713A patent/KR20010013698A/ko not_active Application Discontinuation
- 1998-06-03 TW TW087108721A patent/TW479059B/zh not_active IP Right Cessation
- 1998-06-11 AR ARP980102768A patent/AR014354A1/es not_active Application Discontinuation
- 1998-06-11 CO CO98033543A patent/CO4940481A1/es unknown
- 1998-06-12 ZA ZA9805120A patent/ZA985120B/xx unknown
- 1998-06-12 HR HR19724979.5A patent/HRP980318A2/hr not_active Application Discontinuation
- 1998-06-13 MY MYPI98002644A patent/MY132993A/en unknown
-
1999
- 1999-11-24 BG BG103921A patent/BG103921A/xx unknown
- 1999-12-08 NO NO996045A patent/NO996045L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TR199903061T2 (xx) | 2000-07-21 |
| CO4940481A1 (es) | 2000-07-24 |
| IL132985A0 (en) | 2001-03-19 |
| NZ502237A (en) | 2001-08-31 |
| BG103921A (en) | 2000-07-31 |
| PL337454A1 (en) | 2000-08-14 |
| EP1023296B1 (de) | 2003-12-17 |
| MY132993A (en) | 2007-10-31 |
| DE19724979A1 (de) | 1998-12-17 |
| CA2293440A1 (en) | 1998-12-17 |
| ATE256686T1 (de) | 2004-01-15 |
| CN1259954A (zh) | 2000-07-12 |
| ZA985120B (en) | 1999-12-13 |
| BR9810008A (pt) | 2000-09-19 |
| HUP0002736A2 (hu) | 2001-02-28 |
| AU748697B2 (en) | 2002-06-13 |
| KR20010013698A (ko) | 2001-02-26 |
| SK174399A3 (en) | 2000-05-16 |
| WO1998056793A1 (de) | 1998-12-17 |
| AR014354A1 (es) | 2001-02-28 |
| EP1023296A1 (de) | 2000-08-02 |
| JP2002504104A (ja) | 2002-02-05 |
| US6159981A (en) | 2000-12-12 |
| NO996045D0 (no) | 1999-12-08 |
| AU8535798A (en) | 1998-12-30 |
| TW479059B (en) | 2002-03-11 |
| NO996045L (no) | 1999-12-08 |
| ID24045A (id) | 2000-07-06 |
| DE59810485D1 (de) | 2004-01-29 |
| ES2215312T3 (es) | 2004-10-01 |
| HUP0002736A3 (en) | 2001-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODBC | Application rejected |