SK282108B6 - Substituované dihydropyranopyridíny, spôsob a medziprodukty na ich výrobu a farmaceutické prostriedky na ich báze - Google Patents
Substituované dihydropyranopyridíny, spôsob a medziprodukty na ich výrobu a farmaceutické prostriedky na ich báze Download PDFInfo
- Publication number
- SK282108B6 SK282108B6 SK194-96A SK19496A SK282108B6 SK 282108 B6 SK282108 B6 SK 282108B6 SK 19496 A SK19496 A SK 19496A SK 282108 B6 SK282108 B6 SK 282108B6
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- hydrogen
- amino
- formula
- mono
- Prior art date
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- 239000000543 intermediate Substances 0.000 title claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title abstract description 15
- -1 cyano, aminocarbonyl Chemical group 0.000 claims abstract description 71
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 206010027599 migraine Diseases 0.000 claims abstract description 10
- 230000024883 vasodilation Effects 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 208000035475 disorder Diseases 0.000 claims abstract description 5
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 4
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 150000003254 radicals Chemical class 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 125000005936 piperidyl group Chemical group 0.000 claims description 16
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 5
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
- XNARZJQXBMWIQU-UHFFFAOYSA-N 3,4-dihydro-2h-pyrano[3,2-b]pyridine Chemical class C1=CN=C2CCCOC2=C1 XNARZJQXBMWIQU-UHFFFAOYSA-N 0.000 claims 1
- 101000927265 Hyas araneus Arasin 2 Proteins 0.000 claims 1
- YHZMDZKWJAYURC-UHFFFAOYSA-N N-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-ylmethyl)-N'-(2-methylsulfanylpyrimidin-4-yl)propane-1,3-diamine Chemical compound CSC1=NC=CC(NCCCNCC2OC3=NC=CC=C3CC2)=N1 YHZMDZKWJAYURC-UHFFFAOYSA-N 0.000 claims 1
- SZABWKUQLZVMNW-UHFFFAOYSA-N ON(CCCNC1=NC=CC=N1)CC1OC2=NC=CC=C2CC1 Chemical compound ON(CCCNC1=NC=CC=N1)CC1OC2=NC=CC=C2CC1 SZABWKUQLZVMNW-UHFFFAOYSA-N 0.000 claims 1
- 206010047141 Vasodilatation Diseases 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- JOGDPPWFEHUNIH-UHFFFAOYSA-N n-(3,4-dihydro-2h-pyrano[2,3-b]pyridin-2-ylmethyl)-n'-pyridin-2-ylpropane-1,3-diamine Chemical compound C1CC2=CC=CN=C2OC1CNCCCNC1=CC=CC=N1 JOGDPPWFEHUNIH-UHFFFAOYSA-N 0.000 claims 1
- XVWDKUASLUMSAX-UHFFFAOYSA-N n-(3,4-dihydro-2h-pyrano[3,2-c]pyridin-2-ylmethyl)-n'-pyrimidin-2-ylpropane-1,3-diamine Chemical compound C1CC2=CN=CC=C2OC1CNCCCNC1=NC=CC=N1 XVWDKUASLUMSAX-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 52
- 239000000203 mixture Substances 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 35
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- 239000004480 active ingredient Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 239000003826 tablet Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
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- 238000002360 preparation method Methods 0.000 description 7
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- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
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- 239000002552 dosage form Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 206010019233 Headaches Diseases 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 235000014655 lactic acid Nutrition 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
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- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 3
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 2
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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- FHYDQGOVTLQZSZ-UHFFFAOYSA-N n'-pyrimidin-2-ylpropane-1,3-diamine Chemical compound NCCCNC1=NC=CC=N1 FHYDQGOVTLQZSZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/08—Vasodilators for multiple indications
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93202440 | 1993-08-19 | ||
| PCT/EP1994/002700 WO1995005381A1 (en) | 1993-08-19 | 1994-08-12 | Vasoconstrictive substituted dihydropyranopyridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK19496A3 SK19496A3 (en) | 1997-02-05 |
| SK282108B6 true SK282108B6 (sk) | 2001-11-06 |
Family
ID=8214053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK194-96A SK282108B6 (sk) | 1993-08-19 | 1994-08-12 | Substituované dihydropyranopyridíny, spôsob a medziprodukty na ich výrobu a farmaceutické prostriedky na ich báze |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5691344A (cs) |
| EP (1) | EP0714395B1 (cs) |
| JP (1) | JP3650398B2 (cs) |
| KR (1) | KR100330697B1 (cs) |
| CN (1) | CN1051085C (cs) |
| AT (1) | ATE178330T1 (cs) |
| AU (1) | AU684819B2 (cs) |
| BR (1) | BR9407298A (cs) |
| CA (1) | CA2168022C (cs) |
| CZ (1) | CZ286645B6 (cs) |
| DE (1) | DE69417560T2 (cs) |
| DK (1) | DK0714395T3 (cs) |
| ES (1) | ES2132424T3 (cs) |
| FI (1) | FI113773B (cs) |
| GR (1) | GR3029924T3 (cs) |
| HU (1) | HU228673B1 (cs) |
| IL (1) | IL110688A (cs) |
| MY (1) | MY111419A (cs) |
| NO (1) | NO315001B1 (cs) |
| NZ (1) | NZ271383A (cs) |
| PL (1) | PL177516B1 (cs) |
| RO (1) | RO116729B1 (cs) |
| RU (1) | RU2135501C1 (cs) |
| SI (1) | SI0714395T1 (cs) |
| SK (1) | SK282108B6 (cs) |
| WO (1) | WO1995005381A1 (cs) |
| ZA (1) | ZA946268B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| DE19950647A1 (de) * | 1999-10-21 | 2001-04-26 | Merck Patent Gmbh | Imidazolderivate als Phosphodiesterase VII-Hemmer |
| US6818659B2 (en) | 2001-11-06 | 2004-11-16 | Bristol-Myers Squibb Pharma, Inc. | (2S)-2-amino-4-(2-amino-(3,4,5,6-tetrahydropyrimidin-4-yl) butanoyl and its use in cyclic and acyclic peptides |
| CN109476675B (zh) * | 2016-07-01 | 2022-12-09 | 爱尔兰詹森科学公司 | 用于治疗病毒性感染的二氢吡喃并嘧啶衍生物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU403673A1 (ru) * | 1971-10-05 | 1973-10-26 | Авторы изобретени витель | Способ получения 2-амино-4н-пирано |
| SU466228A1 (ru) * | 1973-02-28 | 1975-04-05 | Дальневосточный государственный университет | Способ получени 2,4-дифенил-7,7диметилтетрагидропирано(4,3-в)пиперидина |
| SU943240A1 (ru) * | 1980-05-28 | 1982-07-15 | Пермский государственный фармацевтический институт | Способ получени производных 10-окси-10н-пиридо [2,3- @ ХРОМЕНОВ |
| US4405622A (en) * | 1980-10-16 | 1983-09-20 | Syntex (U.S.A.) Inc. | [1-(1,4-Benzodioxan-2-yl)-4-(4-aminopyrimidin-2-yl]piperazines useful as anti-depressants |
| AU576868B2 (en) * | 1984-06-11 | 1988-09-08 | E.I. Du Pont De Nemours And Company | Thiophene and pyridine sulfonamides |
| FR2615191B1 (fr) * | 1987-05-16 | 1991-01-11 | Sandoz Sa | Nouveaux benzo(b)pyrannes et pyrannopyridines, leur preparation et leur utilisation comme medicaments |
| DE3901814A1 (de) * | 1988-07-28 | 1990-02-01 | Bayer Ag | Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga |
| US5140031A (en) * | 1989-05-31 | 1992-08-18 | E. R. Squibb & Sons, Inc. | Pyranyl cyanoguanidine derivatives |
| US5250450A (en) * | 1991-04-08 | 1993-10-05 | Micron Technology, Inc. | Insulated-gate vertical field-effect transistor with high current drive and minimum overlap capacitance |
| DE4120322A1 (de) * | 1991-06-20 | 1992-12-24 | Bayer Ag | Aminomethyl-substituierte 2,3-dihydropyrano(2,3-b)pyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| SI9300097B (en) * | 1992-02-27 | 2001-12-31 | Janssen Pharmaceutica Nv | (benzodioxan, benzofuran or benzopyran) alkylamino) alkyl substituted guanidines |
-
1994
- 1994-08-12 DE DE69417560T patent/DE69417560T2/de not_active Expired - Lifetime
- 1994-08-12 AU AU74995/94A patent/AU684819B2/en not_active Expired
- 1994-08-12 CN CN94193178A patent/CN1051085C/zh not_active Expired - Lifetime
- 1994-08-12 PL PL94313080A patent/PL177516B1/pl unknown
- 1994-08-12 JP JP50675095A patent/JP3650398B2/ja not_active Expired - Lifetime
- 1994-08-12 CA CA002168022A patent/CA2168022C/en not_active Expired - Lifetime
- 1994-08-12 CZ CZ1996373A patent/CZ286645B6/cs not_active IP Right Cessation
- 1994-08-12 HU HU9600374A patent/HU228673B1/hu unknown
- 1994-08-12 AT AT94924873T patent/ATE178330T1/de active
- 1994-08-12 DK DK94924873T patent/DK0714395T3/da active
- 1994-08-12 US US08/586,851 patent/US5691344A/en not_active Expired - Lifetime
- 1994-08-12 KR KR1019960700633A patent/KR100330697B1/ko not_active Expired - Lifetime
- 1994-08-12 SI SI9430252T patent/SI0714395T1/xx unknown
- 1994-08-12 BR BR9407298A patent/BR9407298A/pt not_active Application Discontinuation
- 1994-08-12 WO PCT/EP1994/002700 patent/WO1995005381A1/en active IP Right Grant
- 1994-08-12 RU RU96105947A patent/RU2135501C1/ru active
- 1994-08-12 NZ NZ271383A patent/NZ271383A/en not_active IP Right Cessation
- 1994-08-12 EP EP94924873A patent/EP0714395B1/en not_active Expired - Lifetime
- 1994-08-12 ES ES94924873T patent/ES2132424T3/es not_active Expired - Lifetime
- 1994-08-12 RO RO96-00283A patent/RO116729B1/ro unknown
- 1994-08-12 SK SK194-96A patent/SK282108B6/sk not_active IP Right Cessation
- 1994-08-17 MY MYPI94002159A patent/MY111419A/en unknown
- 1994-08-17 IL IL11068894A patent/IL110688A/en not_active IP Right Cessation
- 1994-08-18 ZA ZA946268A patent/ZA946268B/xx unknown
-
1996
- 1996-02-16 FI FI960721A patent/FI113773B/fi not_active IP Right Cessation
- 1996-02-19 NO NO19960647A patent/NO315001B1/no not_active IP Right Cessation
-
1999
- 1999-04-07 GR GR990401017T patent/GR3029924T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20140812 |